Eucalyptus The Genus Eucalyptus PDF

Eucalyptus
The Genus Eucalyptus
Edited by
John J.W. Coppen
London and New York
Copyright 2002 Taylor and Francis

First published 2002
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Contents
List of contributors
Preface to the series
Preface
PART 1
General aspects
1 Botany of the eucalypts
IAN BROOKER
2 Eucalyptus, water and the environment

IAN R. CALDER
3 Eucalypts in cultivation: an overview

JOHN W. TURNBULL AND TREVOR H. BOOTH
4 Genetic improvement of eucalypts: with special reference to

oil-bearing species
JOHN C. DORAN
5 Eucalyptus chemistry
JOSEPH J. BROPHY AND IAN A. SOUTHWELL
6 Distillation of eucalyptus leaf oils: theory and practice

E.F.K. DENNY
PART 2
Cultivation and production of eucalypts around the world:
with special reference to the leaf oils 1
7 Cultivation and production of eucalypts in Australia:
with special reference to the leaf oils
G E O FFR EY R . DAV I S
8 Cultivation and production of eucalypts in the Peoples

Republic of China: with special reference to the leaf oils
SHAOXIONG CHEN

9 Cultivation and production of eucalypts in Africa:
PAUL A. JACOVELLI
10 Cultivation and production of eucalypts in South America:

LARCIO COUTO
11 Cultivation and production of eucalypts in India:

S.S. HANDA, R.K. THAPPA AND S.G. AGARWAL
PART 3
Biological and end-use aspects
12 Chemistry and bioactivity of the non-volatile constituents
of eucalyptus
TAKAO KONOSHIMA AND MIDORI TAKASAKI
13 Antimicrobial activity of eucalyptus oils

STANLEY G. DEANS
14 Eucalyptus in insect and plant pest control: use as a mosquito

repellent and protectant of stored food products; allelopathy
PETER GOLOB, HIROYUKI NISHIMURA AND ATSUSHI SATOH
15 Chemical ecology of herbivory in eucalyptus: interactions

between insect and mammalian herbivores and plant essential oils
IVAN R. LAWLER AND WILLIAM J. FOLEY
16 Eucalyptus oil products: formulations and legislation

JUDI BEERLING, STEVE MEAKINS AND LES SMALL
17 Production, trade and markets for eucalyptus oils

JOHN J.W. COPPEN
18 Research trends and future prospects

ERICH V. LASSAK
Appendices
1 Sources of eucalyptus seed
2 Estimates of eucalypt plantations worldwide
3 Advice to a prospective new producer of eucalyptus oil
or other leaf extractive
4 Composition of some commercially distilled eucalyptus oils
5 Quality criteria and specifications of eucalyptus oils
6 Packaging and labelling requirements for the handling
and transportation of eucalyptus oils
7 Useful addresses

Contributors
S.G. Agarwal, Regional Research Laboratory, Jammu-Tawi 180 001, India.

Judi Beerling, Quest International, Kennington Road, Ashford, Kent TN24 0LT, UK.
Trevor H. Booth, CSIRO Forestry and Forest Products, PO Box E4008, Kingston ACT 2604,
Australia.
Ian Brooker, Centre for Plant Biodiversity Research, CSIRO Plant Industry, GPO Box 1600,
Canberra ACT 2601, Australia.
Joseph J. Brophy, Department of Chemistry, University of New South Wales, Kensington,
NSW 2033, Australia.
Ian R. Calder, Centre for Land Use and Water Resources Research, Porter Building, University of
Newcastle, Newcastle-upon-Tyne NE1 7RU, UK.
Shaoxiong Chen, China Eucalypt Research Centre, Renmin Dadao Zhong 30, Zhanjiang,
Guangdong 524022, P.R. China.
John J.W. Coppen, 12 Devon Close, Rainham, Kent ME8 7LG, UK.
Larcio Couto, Departamento de Engenharia Florestal, Universidade Federal de Viosa,
36571 Viosa, MG, Brazil.
Geoffrey R. Davis, G.R. Davis Pty Ltd, PO Box 123, 29-31 Princes Street, Riverstone NSW
2765, Australia.
Stanley G. Deans, Aromatic & Medicinal Plant Group, Food Systems Division, SAC
Auchincruive, South Ayrshire KA6 5HW, UK.
E.F.K. Denny, Denny, McKenzie Associates, PO Box 42, Lilydale, Tasmania 7268, Australia.
John C. Doran, CSIRO Forestry and Forest Products, PO Box E4008, Kingston ACT 2604,
Australia.
William J. Foley, Division of Botany and Zoology, Australian National University,
Canberra 0200, Australia.
Peter Golob, Food Security Department, Natural Resources Institute, University of Greenwich,
Chatham Maritime, Kent ME4 4TB, UK.
S.S. Handa, Regional Research Laboratory, Jammu-Tawi 180 001, India.
Paul A. Jacovelli, 6 Clive Road, Preston, Lancs PR1 0AT, UK.

Takao Konoshima, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607,
Japan.
Erich V. Lassak, Phytochemical Services, 254 Quarter Sessions Road, Westleigh, NSW 2120,
Australia.
Ivan R. Lawler, School of Tropical Environment Studies and Geography, James Cook
University of Queensland, Douglas Q 4811, Australia.
Steve Meakins, Quest International, Kennington Road, Ashford, Kent TN24 0LT, UK.
Hiroyuki Nishimura, Department of Bioscience and Technology, School of Engineering,
Hokkaido Tokai University, Sapporo 005-8601, Japan.
Atsushi Satoh, Department of Bioscience and Technology, School of Engineering,
Hokkaido Tokai University, Sapporo 005-8601, Japan.
Les Small, Quest International, Kennington Road, Ashford, Kent TN24 0LT, UK.
Ian A. Southwell, NSW Agriculture, Wollongbar Agricultural Institute, Wollongbar, NSW
2477, Australia.
Midori Takasaki, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607,
Japan.
R.K. Thappa, Regional Research Laboratory, Jammu-Tawi 180 001, India.
John W. Turnbull, CSIRO Forestry and Forest Products, PO Box E4008, Kingston
ACT 2604, Australia.

Preface to the series
There is increasing interest in industry, academia and the health sciences in medicinal and aromatic
plants. In passing from plant production to the eventual product used by the public, many
sciences are involved. This series brings together information which is currently scattered
through an ever increasing number of journals. Each volume gives an in-depth look at one plant
genus, about which an area specialist has assembled information ranging from the production of
the plant to market trends and quality control.
Many industries are involved such as forestry, agriculture, chemical, food, flavour, beverage,
pharmaceutical, cosmetic and fragrance. The plant raw materials are roots, rhizomes, bulbs,
leaves, stems, barks, wood, flowers, fruits and seeds. These yield gums, resins, essential (volatile)
oils, fixed oils, waxes, juices, extracts and spices for medicinal and aromatic purposes. All these
commodities are traded worldwide. A dealers market report for an item may say Drought in the
country of origin has forced up prices.
Natural products do not mean safe products and account of this has to be taken by the above
industries; which are subject to regulation. For example, a number of plants which are approved
for use in medicine must not be used in cosmetic products.
The assessment of safe to use starts with the harvested plant material which has to comply
with an official monograph. This may require absence of, or prescribed limits of, radioactive
material, heavy metals, aflatoxin, pesticide residue, as well as the required level of active princi-
ple. This analytical control is costly and tends to exclude small batches of plant material. Large
scale contracted mechanised cultivation with designated seed or plantlets is now preferable.
Today, plant selection is not only for the yield of active principle, but for the plants ability to
overcome disease, climatic stress and the hazards caused by mankind. Such methods as in vitro
fertilization, meristem cultures and somatic embryogenesis are used. The transfer of sections of
DNA is giving rise to controversy in the case of some end-uses of the plant material.
Some suppliers of plant raw material are now able to certify that they are supplying organi-
cally-farmed medicinal plants, herbs and spices. The European Union directive (CVO/EU
No. 2092/91) details the specifications for the obligatory quality controls to be carried out at all
stages of production and processing of organic products.
Fascinating plant folklore and ethnopharmacology leads to medicinal potential. Examples are
the muscle relaxants based on the arrow poison, curare, from species of Chondrodendron, and the
anti-malarials derived from species of Cinchona and Artemisia. The methods of detection of phar-
macological activity have become increasingly reliable and specific, frequently involving
enzymes in bioassays and avoiding the use of laboratory animals. By using bioassay linked
fractionation of crude plant juices or extracts, compounds can be specifically targeted which,
for example, inhibit blood platelet aggregation, or have anti-tumour, or anti-viral, or any

other required activity. With the assistance of robotic devices, all the members of a genus may be
readily screened. However, the plant material must be fully authenticated by a specialist.
The medicinal traditions of ancient civilisations such as those of China and India have a large
armamentaria of plants in their pharmacopoeias which are used throughout South-East Asia. A
similar situation exists in Africa and South America. Thus, a very high percentage of the Worlds
population relies on medicinal and aromatic plants for their medicine. Western medicine is also
responding. Already in Germany all medical practitioners have to pass an examination in phy-
totherapy before being allowed to practise. It is noticeable that throughout Europe and the USA,
medical, pharmacy and health related schools are increasingly offering training in phytotherapy.
Multinational pharmaceutical companies have become less enamoured of the single com-
pound magic bullet cure. The high costs of such ventures and the endless competition from me
too compounds from rival companies often discourage the attempt. Independent phytomedicine
companies have been very strong in Germany. However, by the end of 1995, eleven (almost all)
had been acquired by the multinational pharmaceutical firms, acknowledging the lay publics
growing demand for phytomedicines in the Western World.
The business of dietary supplements in the Western World has expanded from the health
store to the pharmacy. Alternative medicine includes plant-based products. Appropriate mea-
sures to ensure the quality, safety and efficacy of these either already exist or are being answered
by greater legislative control by such bodies as the Food and Drug Administration of the USA
and the recently created European Agency for the Evaluation of Medicinal Products, based in
London.
In the USA, the Dietary Supplement and Health Education Act of 1994 recognised the class
of phytotherapeutic agents derived from medicinal and aromatic plants. Furthermore, under
public pressure, the US Congress set up an Office of Alternative Medicine and this office in 1994
assisted the filing of several Investigational New Drug (IND) applications, required for clinical
trials of some Chinese herbal preparations. The significance of these applications was that each
Chinese preparation involved several plants and yet was handled as a single IND. A demonstra-
tion of the contribution to efficacy, of each ingredient of each plant, was not required. This was a
major step forward towards more sensible regulations in regard to phytomedicines.
My thanks are due to the staffs of Harwood Academic Publishers and Taylor & Francis who
have made this series possible and especially to the volume editors and their chapter contributors
for the authoritative information.
Roland Hardman

Preface
The eucalypt, or gum tree, is such an established feature of the Australian landscape that it has
left its mark in that most well-loved of Australian institutions, Waltzing Matilda, penned by
Banjo Patterson towards the end of the nineteenth century:
Once a jolly swagman camped by a billabong,
Under the shade of a coolibah tree1
For those for whom the association between coolibah tree and eucalyptus goes unrecognised
the latter word may, instead, conjure up pictures of koala bears munching contentedly on the
leaves of gum trees. And for yet others, eucalyptus may have medicinal connotations whether
through the use of eucalyptus-flavoured throat lozenges or chest rubs or through eucalyptus oil
and the increasingly popular practice of aromatherapy. In truth, all these associations are genuine
but the single, simple word eucalyptus does not convey the complexity and diversity of all that
it embraces, whether measured in terms of the uses to which it is put or the number of species to
which it refers. Nor does it convey to the man or woman in the street the international nature of
eucalyptus. Australia may be its natural home but its progeny have spread far and wide and the
industries associated with it now span the globe. Whether cultivated as narrow tracts alongside
roads, railways and canals in China and India, or as vast blocks of monoculture in Brazil and else-
where, no continent, outside of Antarctica, has failed to be smitten by the lure of eucalyptus.
The genus Eucalyptus, which is native to Australia and some islands to the north of it, consists
of over 800 species of trees.2 This number continues to grow as new taxa are described. The trees
grow under a wide range of climatic and edaphic conditions in their natural habitat and the very
large and varied gene pool which can be drawn upon for planting purposes is one reason for the
successful introduction of Eucalyptus into so many other countries in the world. Another
reason is the fast-growing nature of eucalypts which makes them ideally suited to obtaining an
economic return within a relatively short period of time. With the advantages have come some
perceived disadvantages, however, and a fair measure of controversy. Not least the effects of euca-
lypts on the soil in terms of water and nutrient abstraction. Calder (Chapter 2) demonstrates that
proper scientific research is now distinguishing between myth and reality and dispelling some of
the misconceptions surrounding eucalyptus and the environment.
1 Eucalyptus coolabah or E. microtheca.

2 Corymbia, previously a sub-genus of Eucalyptus, has been elevated to the rank of a separate genus by Hill and Johnson.
However, since at least one well-known species (Corymbia citriodora) is the source of a commercially important oil,
which will continue to be traded under the name Eucalyptus citriodora, the original classification is retained in this
book to facilitate the discussion.

The multipurpose nature of Eucalyptus and its cultivation for such end-uses as timber, pulp
and fuelwood is generally well described and documented. Information on the medicinal and
aromatic properties of eucalyptus, however, although well known, generally resides in the
primary research literature or is scattered, much of it superficially, in a number of different media
forms. This is particularly true of the commercial and practical aspects of production, both of the
trees themselves and of the pharmaceutical and perfumery products which reach the marketplace
(either the primary extractives, such as eucalyptus oil, or end-use products). It is these aspects,
embracing everything from the land preparation and fertiliser prescriptions used in Africa and
China for the cultivation of oil-bearing species to the chemistry and composition of eucalyptus
oils, from an examination of world trade and prices for the oils and the increasingly burdensome
demands being placed on producers and exporters by legislation and quality specifications to for-
mulations used to make bath foams and hair conditioners, that are described and discussed in this
book. Everything, in short, which should constitute an industrial profile. Some things, such as
distillation, are taken for granted by their practitioners but, as Denny shows (Chapter 6), com-
mercial practice is not always best practice and there is ample scope for improvement. Koalas (and
possums) are not left out and what we learn about their eating habits and preferences (Chapter 15)
may enable us to determine the role of essential oils and related compounds in conferring
resistance to herbivores with considerable economic consequences.
The use of eucalyptus as a commercial source of volatile oil forms the basis for much of the
content of the book, but not all of it. The relative ease with which plant essential oils are dis-
tilled and analysed made them primary targets for early investigation and exploitation. It
remains the case today that they are by far the largest group of eucalyptus extractives to be
exploited for medicinal and fragrance or flavour purposes. However, research in recent years has
uncovered a large number of pharmacologically active non-volatile compounds unique to euca-
lyptus, many of which such as the euglobals and macrocarpals form groups of structurally
similar compounds. Their potential for use in the treatment of AIDS and cancer, amongst other
things, ensures that they will be the subject of much more research in the years to come. Results
to date, and an indication of the species of Eucalyptus which contain the most promising groups
of compounds, are described in some detail.
The native Australian aborigines had long used eucalyptus. Not only its wood and bark for
the fabrication of canoes, spears and boomerangs, and domestic items such as bowls and dishes,
but its leaves, roots and other parts for medicinal purposes. The crushed leaves would inevitably
have disclosed the presence of fragrant oils but it was not until 1788, the year of white settle-
ment in Australia, that the first recorded distillation of eucalyptus oil was made. In 1852 a still
was set up for its commercial production. Joseph Bosisto, who had emigrated from England four
years earlier, established his still on Dandenong Creek, about 40 km southeast of Melbourne,
with the encouragement of Ferdinand von Mueller, then Government Botanist in Victoria. The
rest, as they say, is history.
Today, of the hundreds of species of Eucalyptus that have been shown to contain volatile oil in
their leaves, only about a dozen are utilised, of which six account for the greater part of world oil
production: E. globulus, E. exserta, E. polybractea, E. smithii, E. citriodora and E. dives. Australia
is no longer the main producer of eucalyptus oil this distinction belongs to China, by a long
way but it has maintained a highly efficient industry in the face of competition from more
than a dozen countries. Medicinal-type eucalyptus oil or its main constituent, 1,8-cineole
(eucalyptol) is an ingredient of many hundreds of pharmaceutical products and used for
the treatment of ailments ranging from colds, coughs and congestion to sports injuries and
muscle and joint pain, from insect bites to skin disorders. It is also used in an array of personal
care products such as shampoos, bath foams, soaps and body lotions, not to mention cleaning

agents. All this in addition to use of the neat oil, again in many and varied ways, around the
home. Complementary to the medicinal oils are the perfumery eucalyptus oils, exemplified by
the familiar lemon-scented oil of E. citriodora, used directly for fragrance purposes or as a source
of citronellal.
The existence of chemical variants within the same species of Eucalyptus creates potential pit-
falls for the analyst and producer alike but it also offers prospective benefits arising from plant
selection and breeding. Continued screening of Eucalyptus species, together with research into
aspects such as optimum species and provenance selection for locations outside their natural dis-
tribution, vegetative propagation, improved farm management practices and new applications,
indicates that eucalyptus oil will continue to be an essential oil of major importance in world
trade and usage and to the economy of many countries and communities in both the developed
and developing world. Together with new avenues of research opened up by the discovery of
pharmacologically active non-volatile constituents, and the prospect of treating or preventing a
variety of important human diseases and ailments, eucalyptus may not yet have exhausted its
capacity for surprising us at its multifarious nature.
Finally, I should like to thank all the contributors to this volume for their efforts and exper-
tise, Dr Roland Hardman, Series Editor, for his support and encouragement throughout, and,
not least, my family, particularly Eve, for their patience and understanding.
John J.W. Coppen

Part 1
General aspects

1 Botany of the eucalypts
Ian Brooker
Introduction
There are probably few tree genera that have had as much written about them as the eucalypts.
Indigenous to the Australasian region, they are now among the most widely cultivated of all
plants, particularly in tropical and subtropical parts of the world. The multiple uses to which
eucalypts are put, from construction timber to fuel and pulp, and from oils to amenity planting,
make this plant genus one of the most valuable and widely used in the world.
To the average Australian they are a natural feature of the environment, where vast forests
have been exploited for commercial purposes, often in the expectation that natural regeneration
will sustain an industry more or less permanently. In the last thirty years, however, an awareness
of the need to preserve the forests has become as much a political as a silvicultural necessity.
The perspective in many other countries, where the eucalypt is known as an alien plant, is
different. But after generations of planting the eucalypt may be seen as almost part of the land-
scape, providing fuel, timber and ornamentation in places where the original forests have been
razed beyond the possibility of natural regeneration. In a few countries the eucalypt is the dom-
inant tree in plantations where vast numbers of even-aged trees of more or less identical habit
and size occupy great areas. Their uniformity is often due to the surprisingly small choice of
species, many subsequently cloned or produced by manipulated crossing to package the most
desired characters for site adaptation and specific end use.
When it is considered that relatively few species of eucalypt form the basis of plantation
industries, it may be questioned to what extent this large and greatly variable genus has been
tested. It occurs in a vast assortment of forms and in sites which range from rainforest to alpine
to desert. There is no doubt that among the 800 species of eucalypt which have now been
described, species as yet untried will prove to be successful for a multitude of reasons, whether
for their fuel, timber, fibre, oils or other chemicals, or merely for shelter and amenity.
The discovery of the eucalypts

The popular conception of the discovery of Eucalyptus relates to the voyages of Captain
James Cook in the Endeavour in the 1770s. Following the naming and exploration of
New Zealand on his first voyage, the party arrived on the eastern coast of Australia. From their
first principal landfall which Cook named Botany Bay, they sailed northwards, making plant
collections under the guidance of Sir Joseph Banks. There are several extant eucalypt specimens
from this first voyage, one of which from Botany Bay was described, but not recognised as a
new genus, and was placed in the established genus Metrosideros by the botanist Joseph Gaertner
in 1788.

On Cooks third voyage to the south seas, the botanist of the party, David Nelson, collected a
specimen on Bruny Island to the south of the Tasmanian landmass. Taken back to England it was
studied by the French botanist, Charles Louis LHritier de Brutelle, working at the British
Museum, Natural History, where the specimen remains. He published it in 1788 as the single
species of a new genus which he named Eucalyptus, from the Greek, eu, well, and calyptos, cov-
ered, alluding to the cap (operculum) that covered the stamens in the bud before anthesis. In the
fifty years following Cooks voyages many more eucalypt species were discovered. These were
found by settlers radiating from the new settlements on Port Jackson (Sydney), Hobart,
Melbourne and Adelaide, and by naturalists on exploration trips around the continent, of which
the best known are those of Labillardire in 1792, Robert Brown in 18011803, and that of the
surveyor Allan Cunningham (18171822).
By 1867, when the first substantial classification of the genus Eucalyptus was published by
George Bentham, 135 species were known. Since then hundreds more have been discovered,
with periods of activity coinciding with the efforts of the principal eucalypt botanists operating
at the various times. Notable eras of Eucalyptus publication have been the latter half of the nine-
teenth century (Ferdinand von Mueller), 19031933 (Joseph Henry Maiden) and 1934 (William
Faris Blakely). An indication of the accumulation of named eucalypts is given in Figure 1.1,
where periods of intensive activity can be seen. Considering that eucalypts are now recognised to
number about 800, it appears that, on average, for every species published a synonym has also
been published.
While eucalypts were largely brought to public awareness from the early nineteenth century
onwards, there can be no doubt that eucalypts were known to Europeans well before that time.
In 1699, the English navigator William Dampier landed on the west coast of Australia and
made plant collections which are extant and held at Cambridge, England. There are no eucalypts
among them (A.S. George pers. comm.) but it is unlikely that Dampier or his party could not
have come across them, even though they landed in a very arid part of the continent. The earli-
est collected eucalypt is believed to have come from Ceram, an island of eastern Indonesia. It was
probably Eucalyptus deglupta Blume, one of the few Eucalyptus species not indigenous to the
Australian landmass but occurring in New Guinea, Indonesia and the southern Philippines. The
1800
1600
Number of species published
1400
1200
1000
800
600
400
200
0
1789 1801 1825 1855 1885 1915 1945 1975 1993
Figure 1.1 Numbers of Eucalyptus species published by year.

specimen was not described and published at the time and its history remains a curiosity. The
species was, however, formally described in 1849 by Carl Blume from a sterile specimen earlier
given the manuscript name Populus deglubata.
There is a possibility that a eucalypt species was reasonably well known before the Ceram
specimen. E. alba Reinw. and E. urophylla Blake, the latter only described in 1977, are indige-
nous to Timor and some Indonesian islands and it is likely that these species were encountered
and used by the colonising Portuguese, as well as the local people. Seed may also have been taken
to Brazil, another colony of the Portuguese, from the early 1600s.
The origins of Eucalyptus

Australia is the most arid of continents. Nevertheless, there are significant regions of very high
rainfall along the eastern coast and in southwestern Tasmania. These areas support the remaining
rainforests which, floristically, are in great contrast to the far more widely distributed typical
Australian landscapes dominated by Eucalyptus and Acacia. It was once assumed that the sclero-
phyll vegetation of most of the land surface was the autochthonous flora and that the rainforest
was a later invader, probably from the north, across land bridges which were manifest at times of
low sea level. The more recent theories of plate tectonics, supported by fossil evidence, show that
the present landmass was once part of a single super-continent, Gondwana (Barlow 1981) com-
prising what is now known as New Guinea, Antarctica, India, Arabia, Africa, Madagascar and
South America.
As Gondwana broke up in the Tertiary period, the Australian landmass drifted northwards
from Antarctica. It is believed that in the early part of this drift the continent experienced high
rainfall and was characterised by a relatively uniform rainforest vegetation. The landmass gradu-
ally became drier and the ancient soils lost their fertility. The new land environments became
totally unsuited to rainforest and it contracted, largely to the eastern seaboard. However, by the
evolution of new adaptable forms some plant families were able to occupy the areas of less certain
rainfall and soils of diminishing fertility. Notable examples are Myrtaceae, which spawned the
eucalypts, and Mimosaceae, the distinctive phyllodinous acacias. Both plant groups required mor-
phological and physiological modifications to enable them to thrive. This may be seen in Acacia
in the dominance among the hundreds of dryland species of the phyllode, a modification of the
soft divided leaves of the probable rainforest precursors.
In the case of the eucalypts, the most conspicuous change for the survival of plants in the
harsher environments of the open forests and shrublands can be seen in the leaves and inflores-
cences. In the closed forests there would have been far more competition for sunlight and the
leaves are necessarily dorsiventral, held more or less horizontally, with the photosynthetic tissues
facing upwards and stomata on the underside. For the most successful reproduction of primarily
entomophilous plants, it is likely that the inflorescences should be presented as conspicuously as
possible. This requires that the inflorescence be large and terminal on the crown (e.g. E. calophylla
R. Br. ex Lindley, Figure 1.2). We cannot know what the precursor or precursors of Eucalyptus were,
but from an analysis of the present rainforest and of the sclerophyllous vegetation of
the majority of the Australian environment, Protoeucalyptus may have had the characters given
in Table 1.1.
The contrast between the shadowy environment beneath the crowns of the rainforest and the
intense light of the open forests and shrublands is immense in terms of available sunlight. An
essential adaptation was the development of the isobilateral leaf which, in addition, tended to be
held vertically, often presenting an edge to the sun with the stomata on both sides, a style of leaf
that minimises the effects of direct sunlight and protects the stomata as much as possible.

Figure 1.2 Terminal inflorescences (E. calophylla).
Table 1.1 Suggested characters in Protoeucalyptus
Character Protoeucalyptus
Habit Tree
Bark Rough
Cotyledons Reniform
Juvenile leaf phase Short
Adult leaves Dorsiventral
Leaf oil glands Few and small
Inflorescences Terminal
Sepals Present
Petals Present
Anthers Versatile
Fruit Slightly fleshy
Seeds Hemitropous
It is interesting to observe in leaf characters, however, the present day relationships between
the current species of the more humid forests and their related taxa in the more arid lands. In the
emergence of Eucalyptus and its development of a hierarchy of infra-generic forms, many taxo-
nomic series have present-day species in the humid forests, with unmistakably related species
that have been modified to adapt to the drier environments. This is notable in the bloodwoods,
which have radiated over most of the continent. All the bloodwood species currently in the
humid east and far southwest have dorsiventral leaves. None of the numerous species of the arid
lands in this group has dorsiventral leaves. The situation of the northern tropics, with their
short, very wet season and long dry one, is somewhat different, with predominantly dorsiventral
species and some isobilateral ones. Examples of humid-climate, dorsiventrally-leaved species and
dry-climate, isobilaterally-leaved species of the same taxonomic groups are shown in Table 1.2.
The situation with the inflorescence is somewhat different. While there has been an apparent
retreat of the inflorescence from the outside of the crown to the leaf axils in most taxonomic
groups (e.g. E. pyrocarpa L. Johnson & Blaxell, Figure 1.3), the bloodwood species in particular
have retained the terminal inflorescence in all arid zone species. All bloodwood species, whether

Table 1.2 Examples of related pairs of Eucalyptus species showing advance from
the primitive dorsiventral leaf to the isobilateral leaf
Taxonomic group Dorsiventral leaves Isobilateral leaves

(humid regions) (dry regions)
Red bloodwoods E. polycarpa E. terminalis

Yellow bloodwoods E. leptoloma E. eximia
Swamp gums E. brookeriana E. ovata
Apple boxes E. angophoroides E. bridgesiana
Boxes E. rummeryi E. microtheca
Ironbarks E. paniculata E. beyeri
White mahoganies E. acmenoides E. apothalassica
Stringybarks E. muelleriana E. macrorhyncha
Figure 1.3 Axillary inflorescences (E. pyrocarpa).
of the humid forests or of the inland arid regions, have the primitive terminal inflorescence
(Figure 1.2). However, several hundred species of the other taxonomic groups which have radi-
ated across the continent, and which occur in myriad environments, have the derived axillary
inflorescence.
The bark of Protoeucalyptus was probably rough. This has been retained without exception in
the eastern bloodwood species occupying humid regions. Desert species provide a contrast and
the rough bark may vary from nil to rough over part or most of the trunk. The adaptive nature
of rough bark is open to much speculation. It may appear to be protective but is scarcely a neces-
sity as rough and smooth-barked species grow in association in many varying environments. The
form of the bark, whether rough or smooth, remains a powerful aid in identifying taxonomic
groups within the genus, although experience is required to distinguish the different types.
Classification in the genus Eucalyptus

The genus Eucalyptus, which began in formal botanical terms as a single species, E. obliqua
LHrit., in 1788, has now been recognised to comprise about 800 species, in numbers second

only in Australia to Acacia. By 1800 only a few species had been described. These were, as
expected, all from around the new colony at Port Jackson (Sydney). Most were named by Joseph
Smith working at the British Museum. They include many of the most valuable timber species
which, then as now, must have been the most important in a pioneer settlement for construction
and fuel, namely, E. saligna Smith, E. resinifera Smith, E. pilularis Smith, E. capitellata Smith and
E. paniculata Smith.
In the first half of the nineteenth century, land and sea-based expeditions resulted in the dis-
covery of many more new eucalypts. Groups of related species soon became evident, e.g. the
stringybarks and the ironbarks. Consequently, a comprehensive classification of the 135 known
species into these recognisable categories, as formal series and subseries, was published in 1867 by
George Bentham of the Royal Botanic Gardens, Kew, England. He did not visit Australia but was
greatly assisted by the endeavours of the great scientist Ferdinand von Mueller, working from
Melbourne, who sent Bentham plant material on which to base his studies.
Bentham devised a system that divided the eucalypts into five taxonomic series based on sta-
men characters. For each group he further discussed other characters such as bark, habit, etc.,
although these latter appear not to be essentially diagnostic. His largest series was divided into
subseries based on the structure of the inflorescence and, to a lesser extent, the leaves. Overall,
Benthams system of classification was a brave attempt to order the eucalypts but his groupings
have little relevance today.
The sixty years following Bentham saw the major researches in Eucalyptus of Joseph Henry
Maiden and William Faris Blakely working at the Royal Botanic Gardens, Sydney. Their collab-
oration culminated in the monumental A Critical Revision of the genus Eucalyptus by Maiden
(19031933) which was a descriptive and historical treatment of all eucalypt species known to
the time, together with detailed analyses of certain organs, e.g. the anthers, cotyledons and
seeds. Maiden produced no comprehensive classification but this was remedied by his
co-worker, Blakely, who published in 1934 his Key to the Eucalypts an intricately
constructed system treating 606 species and varieties, bearing some resemblance to Benthams
classification but improved by the reference to many more characters, such as ontogenic devel-
opment of the leaves, the inflorescences, buds, fruits and habit.
Blakelys work marks the high point of the discipline of purely comparative morphology,
although his stated aim was to place species in the most natural position to each other and
kindred genera. With no instruction as to his methodology, it is not possible to determine if
his estimations of similarities were unquestionable and intentional expressions of homology
to indicate natural affinities. There has been no formal, comprehensive classification since
Blakelys Key.
Few new eucalypt species were published immediately following Blakely and in the twenty-five
years after World War II, and a period of stability in numbers appeared to have set in. It was
about this time that a new, but not formalised, classification was published by Lindsay Pryor of
the Australian National University, Canberra, and Lawrie Johnson of the Royal Botanic
Gardens, Sydney (Pryor and Johnson 1971). Pryor was a strong advocate of the importance of
breeding barriers in assessing natural affinities. The authors stated that there are several com-
pletely reproductively isolated groups within Eucalyptus and these conform to the subgenera of
our system. Pryor and Johnsons system is explicitly phylogenetic and divided the genus into
seven subgenera (Table 1.3). Their taxonomic sections, series, subseries and superspecies were
not qualified by diagnostic data but the classification became the benchmark for a host of subse-
quent eucalypt studies.
Pryor and Johnsons classification was deliberately extracodical (informal and outside the Code
of Botanical Nomenclature). The system was hierarchical (sections, series, etc.) and contrasts with

Table 1.3 The classification of Pryor and Johnson (1971) with examples of
well-known species in the taxa
Subgenera (Pryor and Johnson 1971) Well-known species and species groups
Blakella Ghost gums (e.g. E. tessellaris)

Corymbia Bloodwoods (e.g. E. citriodora)
Eudesmia Includes E. miniata and E. baileyana
Gaubaea Comprises E. curtisii and E. tenuipes
Idiogenes E. cloeziana only
Monocalyptus White mahoganies (e.g. E. acmenoides),
stringybarks (e.g. E. globoidea),
blackbutts (e.g. E. pilularis),
ashes (e.g. E. obliqua),
peppermints (e.g. E. dives, E. radiata)
Symphyomyrtus Red mahoganies (e.g. E. robusta),
red gums (e.g. E. camaldulensis),
mallees (e.g. E. polybractea),
gums (e.g. E. globulus),
boxes (e.g. E. polybractea),
ironbarks (e.g. E. staigeriana)
Table 1.4 Proposed new classification of the genus Eucalyptus (Brooker unpubl.)
Subgenus Angophora
Subgenus Corymbia sensu Pryor and Johnson 1971
Subgenus Blakella sensu Pryor and Johnson 1971
Subgenus (E. curtisii)
Subgenus (E. guilfoylei)
Subgenus Eudesmia sensu Pryor and Johnson 1971
Subgenus Symphyomyrtus sensu Pryor and Johnson 1971
Subgenus (E. raveretiana, E. brachyandra, E. howittiana, E. deglupta)
Subgenus (E. microcorys)
Subgenus (E. tenuipes)
Subgenus Idiogenes sensu Pryor and Johnson 1971 (E. cloeziana)
Subgenus (E. rubiginosa)
Subgenus Eucalyptus (!Monocalyptus in Pryor and Johnson 1971)
the formal classification used by Chippendale (1988), where only one infra-generic rank (series)
was used. This latter work, however, made possible the formal reference of all species published
up to 1988 to taxonomic series, which is generally required in systematic papers.
The most recent major contribution to classification in the genus Eucalyptus was made by Hill
and Johnson (1995) who formally published a new genus, Corymbia, comprising two of the
subgenera of the Pryor and Johnson classification (1971), namely, Corymbia and Blakella. The
rationale for this step was based on cladistic analyses of all the traditional eucalypt components
at the general subgenus level and is corroborated by molecular studies of Udovicic et al. (1995).
Some ambiguity, however, remains over the relationship of the closely related genus Angophora
Cav. A recent study on the relationships within Eucalyptus concluded that Angophora, Corymbia
and Blakella form a monophyletic group (Sale et al. 1996). Perhaps all these recent studies
should be considered merely as hypotheses that will contribute ultimately to an optimum system
with further researches. My current preference is for a single genus consisting of thirteen subgenera
(Table 1.4), namely, the five major subgenera of Pryor and Johnson (1971), the genus Angophora, a

subgenus comprising the four tropical species with the small fruit, and six single-species
subgenera a system embracing demonstrable morphological distinctions.
While comparative morphology is the basis for estimating natural affinities and resulting
classification, the value of characters used varies greatly. Features such as bark in eucalypts have
been traditionally used in keys and descriptions, but bark as a character is only of medium relia-
bility as its constant exposure to the elements results in attrition and change of colour. Internal
characters protected from outside influences are of higher reliability. In this respect, essential oils
have been considered as possible aids to testing natural affinities. Little success has been
achieved and it may be concluded that the developmental pathways for morphology and for
essential oils are not closely associated within the eucalypt plant.
In contrast, essential oils have been useful in distinguishing related species. This is easily
demonstrated in the distinctive lemon-scented E. citriodora Hook. when compared with the
closely related E. maculata Hook. The latter species does not contain citronellal and so lacks the
lemon fragrance. Another instance is the distinction between E. ovata Labill., which has a very low
oil content, and the related E. brookeriana A. Gray, which is rich in oil, particularly 1,8-cineole
(Brooker and Lassak 1981).
Complicating the situation is the well known phenomenon in eucalypts of the variation in
essential oil composition between individual trees and races of trees. In the 1920s, Penfold and
Morrison reported the existence of several races in the broad-leaved peppermint which they
named E. dives Schau. Type, E. dives var. A, var. B and var. C, according to their broad chem-
ical groupings (e.g. Penfold and Morrison 1929; see also Penfold and Willis 1961). The latter
variety was of greatest commercial importance since it was particularly high in 1,8-cineole.
Today, these different types are regarded simply as examples of what may be a wide range of
possible chemical variants or chemotypes and not given formal names, although the old nomen-
clature sometimes still persists.
The eucalypt plant
Habit
The plantation eucalypt is notably a fast-growing tree of good form (e.g. E. maculata, Figure 1.4),
suitable for modern harvesting practices and intended ultimately for use as pole timber or a
source of fibre. The species used for these purposes are remarkably few in number. They mostly
originate in the wetter forests of the eastern seaboard of the Australian continent, e.g. E. grandis
W. Hill ex Maiden, E. saligna, E. globulus Labill., E. tereticornis Smith, E. nitens (Deane & Maiden)
Maiden, E. dunnii Maiden and E. smithii R. Baker. These species are tall trees from the natural
forested areas and altogether number about fifty, and include some from the far southwest of
Western Australia, namely, E. marginata Donn ex Smith and E. diversicolor F. Muell.
In drier regions, and often on less fertile soils, smaller trees of woodland habit and habitat
dominate (e.g. E. kumarlensis Brooker, Figure 1.5). There are about 250 species of predominantly
woodland form and they occupy the hills, slopes, plateaus and mountains, and the heavier soils of
the plains. Notable among these is the widespread river red gum, E. camaldulensis Dehnh., which
is a large spreading tree of freshwater streams across most of the continent. Its adaptability to
many differing habitats has made it one of the most widely planted trees in other countries,
where it is chosen for its fast growth, hard timber and excellent fuel.
Most of the interior of Australia is arid, and Acacia is the dominant genus, but eucalypt
species are usually to be found in these regions along the seasonal streams and in the rocky hills.
In the south, particularly, there are extensive sandplains of low fertility. These support the very

Figure 1.4 Forest tree with long bole and small terminal crown (E. maculata).
Figure 1.5 Woodland tree with short bole and large spreading crown (E. kumarlensis).
numerous mallee species (about 180 in all) although a few occur in eastern uplands, e.g.
E. approximans Maiden and E. gregsoniana L. Johnson & Blaxell. The mallee is the dominant form
over wide areas of tall shrubland. As a mature plant it is easily recognised by the multi-stemmed
habit (e.g. E. livida Brooker & Hopper, Figure 1.6) and the presence of a lignotuber which is
either buried just below the soil surface or is exposed through weathering of the soil.

Figure 1.6 Mallee with multiple stems (E. livida).
Figure 1.7 Seedling of E. dwyeri showing small lignotubers which have formed in the axils of fallen
cotyledons.
The lignotuber
Most Eucalyptus species develop lignotubers. They begin as swellings in the axils of the cotyle-
dons (e.g. E. dwyeri Maiden & Blakely, Figure 1.7). As the seedling gets older the swellings form
in the axils of several of the lower leaf pairs. They are usually conspicuous on the young stem as
they necessarily form decussately. The swellings coalesce and often engulf the upper part of the
root. The whole bulbous mass becomes lignified and is a store of dormant shoots which develop
and produce new stem structures when the upper part of the plant is lost through cutting, fire,
grazing, etc. In very old eucalypts the lignotuber may be massive.

The lignotuber is a vital organ in the regeneration of trees or mallees and its evolution may be
a particular response to ancient and constant fire regimes. Not all eucalypts form lignotubers
and the regenerative capacity of the plant is an important factor in the choice of species for plan-
tations in which repeated harvests for oil-bearing foliage are the requirement. Species best suited
to a plantation and harvesting programme are those which are lignotuberous and guarantee cop-
pice regeneration. Because of the large number of Eucalyptus species and the task required to
detect lignotubers in all taxa and provenances, there is no comprehensive list of species which
form lignotubers.
Most eucalypts form lignotubers, yet many of the best known commercial species are non-
lignotuberous, e.g. E. regnans F. Muell., E. delegatensis Smith, E. pilularis, E. grandis and E. nitens
(Jacobs 1955). These are species of wet forests of southeastern Australia which regenerate prolif-
ically from seed, especially after site disturbance. In these species the base of the stem or trunk
becomes swollen and is a store of dormant buds which respond much like the true lignotuber
and result in coppice regrowth from a felled tree base. E. diversicolor, also non-lignotuberous,
occupies high rainfall country of southwestern Australia, but the same regenerative process
occurs in species of the much drier country of Western Australia, e.g. E. astringens (Maiden)
Maiden. This species is one of several that are both non-lignotuberous and of distinctive mallett
habit, in which the trunk branches low and produces a characteristic crown of steep branches
(Brooker and Kleinig 1990).
E. camaldulensis, which has the widest natural distribution of all eucalypt species, is variable in
lignotuber formation. Populations in the northern half of the Australian continent are reported
to be lignotuberous while southern populations are non-lignotuberous (Pryor and Byrne 1969),
although recent seedling studies (CSIRO unpubl.) indicate that stress on the young plant is as
important a stimulus for lignotuber formation as genetic predisposition.
Bark
The bark character in Eucalyptus is one of the most difficult to assess and describe. It has long
been recognised that many species shed their outer bark each year and that others retain the dead
bark. The eucalypt tree puts on an annual increment of bark tissue. Regular decortication results
in smooth bark, while retention of dead bark results in rough bark, but the colour, form and
thickness of the bark types varies conspicuously with the taxonomic grouping and with the age
of the tree, its health, the season, etc. Recognition of the various bark types can only be achieved
by regular field experience but, when learnt, it provides the botanist, naturalist and forester with
a powerful tool in the recognition of species and taxonomic categories.
It is also important to bear in mind that most of the bark descriptions in texts have been made
from trees growing in their natural environments, and that different conditions, particularly in
other countries where eucalypts are planted, may result in different responses of colour and texture.
Smooth bark
The outer dead bark of some species and species groups sheds in slabs at a particular time of
the year. This results in the sudden exposure of the underbark which is a different colour and
soon changes with weathering until the trunk is an even grey or pale pink (e.g. E. citriodora,
Figure 1.8). Such a trunk contrasts strongly with a rough-barked species (e.g. E. macrorhyncha
F. Muell., Figure 1.9).
In the red gums (e.g. E. camaldulensis, Figure 1.10), and the grey gums, the outer bark sheds
in irregular patches at different times during the year. The freshly-exposed underbark is usually

Figure 1.8 Bark completely shed leaving a smooth bole (E. citriodora).
Figure 1.9 Bark retained forming a rough bole (E. macrorhyncha).

Figure 1.10 Mottled smooth bark (E. camaldulensis).
brightly coloured yellow or coppery, which fades to light grey and then weathers to dark grey.
The trunks can be spectacular immediately after decortication, and even over a whole year
a mottled effect of three colours can be seen. Other species shed their bark in ribbons, e.g.
E. viminalis Labill. and E. globulus, and some of these species hold the partly shed ribbons
hanging in the crown, where they accumulate season after season and give rise to the name
ribbon gums (Figure 1.11).
Rough bark
When the dead bark accumulates year by year it dries by the loss of soft tissue and the fibres
remain. The resulting rough bark has many forms. The outer layers usually weather to grey over-
lying the red-brown unexposed inner rough bark, which will be exposed later by the attrition of
the outer fibres. The fibres may form long strings that can be pulled off, as in the stringybarks
(e.g. E. macrorhyncha, Figure 1.9). The rough bark may break into flakes or squares so charac-
teristic of the bloodwoods (e.g. E. calophylla, Figure 1.12). In a large group of species the rough
bark becomes infused with kino, a natural exudate, resulting in extremely hard bark that is usu-
ally deeply furrowed, as in the ironbarks (e.g. E. cullenii Cambage, Figure 1.13). A few species
have hardened rough bark but, unlike the ironbarks, lack the characteristic deep furrowing over
the whole trunk. These are the compact bark species, e.g. E. fraxinoides Deane & Maiden.
It is not possible to summarise adequately the rough bark types in Eucalyptus in so short a
space, as it is too difficult to treat each form for which the conventional terms do not apply, e.g.
in the many mallee species with some rough bark, and the red gums, swamp gums and moun-
tain gums which are mostly smooth-barked but which have varying amounts of rough bark
which has accumulated at the base of the trunk or stems.

Figure 1.11 Ribbons of bark (E. globulus).
Figure 1.12 Tessellated bark (E. calophylla).

Figure 1.13 Ironbark (E. cullenii).
Figure 1.14 Minniritchi bark (E. caesia).
A small group of species has probably the most beautiful rough bark of all. These are the min-
niritchi group in which the thin, outer, dark red-brown bark only partly sheds longitudinally
(e.g. E. caesia Benth., Figure 1.14). The edges curl and expose fresh green bark, providing partly
rough, partly smooth bark on the green and rich red-coloured stems.
Seeds and germination

The seed morphology of eucalypts is extremely variable. Shape, size, colour and surface orna-
mentation are strongly inherited traits and indicative of taxonomic groups (Boland et al. 1991).
Perhaps the most distinctive seed is that of most of the bloodwoods in which the body of the
seed is basal and subtends a terminal wing. The seed of most species is flattened-ellipsoidal with

a ventral hilum although in some large groups the seed has a terminal hilum. This occurs in
all subgenus Eucalyptus, e.g. E. obliqua, and parts of subgenus Symphyomyrtus, namely, series
Annulares, e.g. E. pellita, series Fimbriatae-lepidotae, e.g. E. propinqua, and series Exsertae, e.g.
E. tereticornis.
There is no endosperm and the bulk of the seed is the embryo, dominated by the cotyledons,
which are flat and appressed in ghost gums (Blakella, Pryor and Johnson 1971) but in all other
species are variously folded across each other. The germinant consists of a radical, root collar,
hypocotyl, cotyledons, epicotyl and terminal growth meristem. Germination is epigeal.
Seedlings and leaf ontogeny

The primitive cotyledon shape is reniform and this form of cotyledon occurs widely in the genus
(Maiden 1933). The extreme modification is the bisected cotyledon formed by emargination,
resulting in a Y-shaped structure. A large number of species have cotyledons shaped between
these extremes and are usually described as bilobed, although the distinction between the
bilobed and the reniform is often blurred.
The normal pattern throughout the life of a eucalypt is to form leaves decussately and this
arrangement is seen most characteristically in the seedling. The leaves are formed in pairs on
opposite sides of the four-sided stem. Successive pairs, as assessed by the axes from the leaf tips
of a pair through the stem, are at right angles to each other. Exceptions are the trigonous stems
and resultant simple spiral leaf pattern in E. lehmannii (Schauer) Benth. and related species (Carr
and Carr 1980) and the spirally-leaved seedlings, based on a five-sided stem, of several mallee
species, e.g. E. oleosa F. Muell. ex Miq. (Brooker 1968).
While opposite leaf pairs continue to be formed at the growth tips of the adult plant, the leaf
arrangement is modified in all species which develop adult leaves, apart from the exceptions
above. The leaf-bearing axis elongates unequally on opposite sides such that the leaf pairs
become separated and the arrangement appears to be alternate (Jacobs 1955). The leaves are usu-
ally petiolate and pendulous and therefore able to become positioned for optimum use of light.
This false alternation may be a simpler way of producing the same effect as a true spiral.
The eucalypt plant is notably heterophyllous and the seedling leaves usually contrast with the
adult leaves in terms of shape, petiolation, disposition in relation to the axis, colour, etc. Blake
(1953) suggested a somewhat arbitrary set of categories to describe the progression of the leaf
forms through the life cycle of the plant, namely, seedling, juvenile, intermediate and adult
leaves. Some species seldom progress beyond the juvenile phase and are reproductively mature
without advancing to the adult phase. Hence the flower buds, flowers and fruit form in the axils
of juvenile leaves which exclusively make up the crown of a mature tree (e.g. E. cinerea F. Muell.
ex Benth.). Most species in this category may form intermediate and adult leaves. A few species
have never been seen in the adult phase, e.g. E. crenulata Blakely ex Beuzev. and E. kruseana
F. Muell., although both of these rare and isolated species hybridise with co-occurring species,
E. ovata DC. and E. loxophleba Benth., respectively, and produce offspring with leaves advanced
from the juvenile state.
The adult leaves
Leaf form and coloredness

The mature crown of most eucalypts consists of adult leaves. These are usually petiolate, pendu-
lous and lanceolate. Those of most species are concolorous (isobilateral). The truly pendulous leaf

is frequently asymmetrical, being oblique at the base on the underside of the vertically hanging
blade. Discolorous (dorsiventral) leaves occur in about fifty species and tend to be held more hor-
izontally. The discolorous leaf is seen most prominently in the bloodwood species of humid
regions, e.g. E. polycarpa F. Muell., and all of the eastern blue gums, e.g. E. grandis, red mahoga-
nies, e.g. E. pellita F. Muell., and the grey gums, e.g. E. propinqua Deane & Maiden. An anom-
alous species of obscure affinity, but widely planted, is E. cladocalyx F. Muell. It occurs in
relatively dry regions of South Australia and is strongly discolorous in the leaf. The fact that no
species with dorsiventral leaves has formed the basis of an essential oil industry indicates that the
increase in oil content and the changes in oil composition have proceeded in the evolutionary
advance of the genus.
The distinction between the two leaf types is a strong diagnostic feature, but a few species
may be difficult to categorise in this respect, e.g. most stringybarks are slightly discolorous.
E. muelleriana A. Howitt., which grows in mesic areas, is the most distinctive of them.
Leaf venation
Leaf venation can be a strong character for the identification of eucalypts. Basically, the midrib
subtends the side veins, between which varying densities of further reticulation occur, i.e. in the
form of tertiary and quaternary veining. The primitive pattern appears to be the strongly pin-
nate form in which the side veins leave the midrib at a wide angle. This is seen in all bloodwoods
(e.g. E. calophylla, Figure 1.15). The most modified form of venation is that seen in snow gums,
e.g. E. pauciflora Sieber ex Spreng. and one or two peppermint species, e.g. E. willisii Ladiges,
Figure 1.15 Bloodwood leaf (E. calophylla) showing wide-angled side veins and oil glands, mostly one
per areole.

Figure 1.16 Leaf of peppermint (E. willisii) showing parallel side veins.
Humphries & Brooker (Figure 1.16). A great variety of patterns occurs between these extremes.
In a very few species, particularly narrow-leaved species, the side veins cannot be seen at all
(e.g. E. approximans).
Oil glands
Eucalyptus leaves are well known for their aromatic oils. Most texts refer to the invariable pres-
ence of oil glands in the leaves although some species are reported as having obscure glands. In
fact many species have no visible glands at all. This situation occurs most commonly in the dry-
land and desert bloodwood species, e.g. E. terminalis F. Muell., and ghost gums, e.g. E. tessellaris
F. Muell. Bloodwood species in more humid regions have oil glands, which are usually small and
appear discretely situated in the middle of the very small areoles. Only one bloodwood of high
rainfall areas, E. ficifolia F. Muell. of far southwestern Western Australia, appears to lack glands.
It can occur sympatrically with E. calophylla, which is always glandular, making the presence or
absence of glands a useful key character for these species, which are often held to be difficult to
distinguish when not in flower. Outside the bloodwood and ghost gum groups, very few species
in wetter areas consistently lack visible leaf glands, although E. fasciculosa F. Muell. (Figure 1.17)
is an exception. The great majority of eucalypt species have conspicuous oil glands in the leaves.
The formation and development of oil glands in the eucalypt leaf has been discussed by
Boland et al. (1991) on the basis of the studies of Carr and Carr (1970) on the formation of
glands in the cotyledon or hypocotyl of the embryo. The process of gland formation begins from
an epidermal cell which, on division, forms casing and epithelial cells for the gland. The cavity
that becomes the oil gland itself derives from the development of an intercellular space that

Figure 1.17 Part of a leaf of E. fasciculosa showing dense reticulation without visible oil glands.
Figure 1.18 Section of a leaf of E. kochii showing oil glands close under both epidermises.
increases in volume and matures as an ovoid or globular cavity (e.g. E. kochii Maiden & Blakely,
Figure 1.18). The epidermal origin of the glands is reflected in the mature leaf, and in a leaf
cross-section the glands are seen to occupy a zone just under the current epidermal layer of one
or both surfaces.

Figure 1.19 Part of a leaf of E. kochii showing dense reticulation and intersectional oil glands.
In the mature adult leaf of most species the oil glands are very conspicuous. Their size, shape
and colour, and their apparent spatial association with veinlets, result in a multitude of patterns
which are useful in the identification of species. The glands may appear to be at the intersections
of veinlets (e.g. E. kochii, Figure 1.19), situated singly in the areoles (e.g. E. calophylla,
Figure 1.15) or few to many within the areoles (e.g. E. microcorys F. Muell., Figure 1.20), or a
combination of both. In a few species they are so numerous and dense that they obscure the
leaf venation completely (e.g. E. mimica Brooker & Hopper unpubl., Figure 1.21). Within a
species, while the leaf venation pattern remains unaltered and is the more fundamental diagnostic
feature, gland presence and density can vary. For the purposes of field estimation, oil gland
density estimated by visual inspection is no certain indicator of total oil content.
The eucalyptus oil industry in Australia

The English began a settlement at Port Jackson in 1788. Among the settlers first objectives
would have been the need to provide shelter and fuel. For these purposes trees of the native
forests were felled in great numbers for their timber. It would not have taken long for the
aromatic nature of the leaves to be noticed. The oil was loosely referred to as peppermint because
of the supposed resemblance to that of the English peppermint, but the two oils are now known
to be quite different chemically.
In 1789 a sample of oil was sent to England. It is believed to have been steam-distilled from
the Sydney Peppermint, Eucalyptus piperita Smith, and there was obviously a presumed associa-
tion of the effective medicinal properties of the E. piperita oil with those of the peppermint herb

Figure 1.20 Part of a leaf of E. microcorys showing moderate to sparse reticulation and numerous island
oil glands.
Figure 1.21 Leaf of E. mimica showing very numerous oil glands obscuring side veins.
of England. A naval surgeon of the First Fleet, Denis Considen, considered that eucalyptus oil
was much more efficacious in removing all cholicky complaints (Boland et al. 1991).
As European occupation of the new colony extended further north, west and south, numerous
new eucalypts were found, many of which were much richer in oils than the Sydney Peppermint.

Taxonomically the name peppermint became traditionally used for a different group of species,
also in subgenus Eucalyptus, and it was on these that the first eucalyptus oil industry was
founded.
Around 1852 or 1854, a distillation plant was established near Dandenong, east of
Melbourne, using the narrow-leaved peppermint, E. radiata Sieber ex Spreng. (Boland et al.
1991). This species is one of a small group of eucalypts noted for their oils and which have been
exploited for commercial purposes. They still form the basis of small industries in tableland and
mountain country of southeastern Australia. For optimum exploitation of the various species it
was recognised that provenance was important in the choice of leaf material for distillation. This
is now known to be due to the existence of different chemotypes within a species. There are
notable phellandrene and cineole-rich forms of E. radiata, and piperitone and cineole-rich forms
of E. dives. Despite the early successful use of these peppermint species, the industry is now
largely based on entirely unrelated species.
Settlement progressed beyond the mountains and tablelands of southeastern Australia in the
early nineteenth century and onto the inland plains, now mostly cleared and used for agricul-
ture. Pockets of these new lands were unsuitable for cropping because of their infertility or stony
soils but large areas of mallee species were available for exploitation. One in particular, blue
mallee, E. polybractea R. Baker, was found to be rich in cineole and eucalyptus oil industries were
founded on this species over 100 years ago in New South Wales and Victoria.
The mallee plant is peculiarly suited for agricultural practice. It is small, becoming mature
after a few years growth at about 12 m height, although old uncut or unburnt specimens
can exceed 10 m. Its size and precocious maturity makes it ideally suited to mechanical har-
vesting. The propensity for regeneration from the lignotuber allows the virtual perpetual
regrowth of the same biotype and it is harvested at approximately eighteen-month intervals. The
ideal species will have a dense crown for high biomass, high cineole yield, strong regeneration
capacity and fast growth. Selection and cloning will maximise these advantages for plantation
industries.
A new and interesting development in oil mallee farming is being tested in southern Western
Australia. There, vast areas of wheatland have become unproductive through salination, follow-
ing extensive clearing of the natural vegetation. A few eucalypt species are being tested for
growth on affected sites as a means of lowering the water table and, hence, reducing salinity. As
a bonus, it is hoped to harvest the plants at suitable intervals and extract the essential oils. The
species in question, E. kochii, E. horistes L. Johnson & K. Hill, E. polybractea and E. loxophleba
Benth. subsp. lissophloia L. Johnson & K. Hill, have been chosen for their high oil content and
expected adaptation to saline soils (Bartle 1997).
Mallee species seldom grow naturally in pure stands. They usually occur in association with
one or more other eucalypt species of similar habit, but quite unrelated. Where natural stands
were harvested, as in the early years of the industry, the value of these was enhanced by the
culling of the less useful species. The most successful oil-producing centres are now going over
to plantations, particularly of E. polybractea, established either from seed or from vegetatively
reproduced high-yielding individuals.
Few species have been tested for the heritability of eucalyptus oil composition and yield.
A trial of a high-yielding species from Western Australia, E. kochii, had a family heritability
index of 0.83 based on 21x-year-old progeny (Barton et al. 1991). Another trial on the commer-
cially valuable and widely planted E. camaldulensis from Petford in northern Queensland had a
family heritability of 0.62 (Doran and Matheson 1994), indicating that for these two species of
widely differing affinities, growth habits and environments, heritability for essential oil factors
is high.

In contrast to the Australian experience, eucalyptus oil industries in other countries have often
begun as byproducts of eucalypt plantations established for other purposes, e.g. timber or pulp pro-
duction, where large volumes of oil-bearing leaf material are available which would otherwise go to
waste. This is the case in Spain and Portugal. Mallees have received little attention as commercial
trees outside Australia because of their unpromising size and unsuitability for pole timber.
Eucalyptus species used in oil production

In the following digests, arranged alphabetically, Eucalyptus species that are currently exploited
for oil production are described. The first group comprises those species of modest or major
current commercial significance, while the second group are those of lesser economic importance
or those which have significant potential but which are, as yet, not fully exploited.
A number of other species have been used for oil production in the past but are not
described in detail here. Neither are those few which are still very occasionally distilled. None
are likely to assume greater importance in the future. Such species include the following:
1 E. cneorifolia DC., a mallee of Kangaroo Island off South Australia, which is still used for
local cottage industries in the production of 1,8-cineole.
2 E. elata Dehnh., a peppermint common along streams in high rainfall country from west of
Sydney, southwards in the subcoastal ranges to eastern Victoria, which contains high but
variable amounts of piperitone.
3 E. leucoxylon F. Muell., a taxon with several subspecies which occurs in southern South
Australia and western and central parts of Victoria and usually contains 1,8-cineole.
4 E. macarthurii Deane & Maiden, a tree of the Southern Tablelands of New South Wales which
was once harvested for geranyl acetate.
5 E. nicholii Maiden & Blakely, a favourite ornamental tree of the Northern Tablelands of
New South Wales harvested for 1,8-cineole.
6 E. salmonophloia F. Muell., a handsome tree of relatively dry country of southern Western
Australia also harvested for 1,8-cineole.
7 E. sideroxylon Cunn. ex Woolls, an ironbark widespread on the drier slopes and plains associ-
ated with the Great Dividing Range in southeast Queensland and New South Wales which
contains a cineole-rich oil. A distinctive form of E. sideroxylon from coastal New South Wales
and eastern Victoria, once regarded as subsp. tricarpa, is now recognised as a separate species,
E. tricarpa (L. Johnson) L. Johnson & Hill.
8 E. viridis R. Baker, a mallee of the wheatlands of western New South Wales and northern
Victoria which grows with or near E. polybractea, and which contains a similar oil and is often
harvested indiscriminately with it (Weiss 1997).
Remarkably few species are used worldwide as a commercial source of eucalyptus oil.
Boland et al. (1991) state that of the more than 600 species of Eucalyptus probably fewer than
twenty have ever been exploited commercially. Coppen and Hone (1992) state that about a
dozen species are utilised in different parts of the world, of which six account for the greater part
of world production of eucalyptus oils. Inventory surveys in the last fifteen years, however, have
revealed several untried species that could be exploited. It is likely that a compromise may be
sought between industries relying on high biomass availability in relatively low-yield tree
species and those based on species with higher biomass per plant, high yield of desired oils and
ease of mechanical harvesting. Spontaneous regeneration from lignotubers will be an important
property of a desirable species.

Species of commercial significance in essential oil production
E. citriodora Hook. Lemon-scented Gum

This species is one of the best known eucalypts, widely planted in Australia and elsewhere. It is
unusual among eucalypts of subtropical origin in that it thrives in southern Australia among
winter rainfall regimes. The trees are notably tall and erect with completely smooth bark of uni-
form colour, which contrasts with the closely related E. maculata, with its spotted, smooth bark
and southern distribution. The juvenile leaves are typical of the bloodwood group in being large,
alternate, peltate and hairy. The adult leaves of lemon-scented gum are narrowly lanceolate and
on crushing reveal their most conspicuous character, the lemon scent.
E. citriodora belongs to a large taxonomic group, the bloodwoods (subgenus Corymbia), which
are notable for the comparatively large, thick-walled, urceolate fruits. Within this group it is
closely related to only two other species, E. maculata and E. henryi Blake, and together they are
distinguished by the axillary, elongated, compound inflorescences, usually confined to the axils
of the upper leaves, and by the flattened-ellipsoidal, red-black seeds with a cracked seedcoat and
ventral hilum. This smooth-barked group is closest to the yellow bloodwoods, e.g. E. peltata
Benth., which differ by the completely rough bark and the early loss of the outer operculum of
the flower bud.
The leaves of bloodwood species are distinguished by the great number of secondary (side)
veins and their wide angle to the midrib, which approaches 85 degrees. The side veins terminate
at the intramarginal vein beyond which, as is typical in narrow-leaved bloodwoods, there is a
single line of areoles parallel to the leaf margin. In E. citriodora the next degree of veining
between the side veins occurs in about 24 rows, making a very clear, densely reticulate pattern.
The oil glands occur spatially isolated within the areoles, usually single.
The main constituent of the oil of E. citriodora is citronellal, which gives the characteristic
lemon scent. Although the oil has recently found commercial application as the active ingredi-
ent of some mosquito repellents (J. Coppen pers. comm.), it is used mainly for perfumery pur-
poses. It is produced mainly in China, India and Brazil. Only one other Eucalyptus species has a
lemon-scented oil, the citral-rich E. staigeriana F. Muell. ex Bailey (Lemon-scented Ironbark).
This is unrelated to the Lemon-scented Gum and is easily distinguished from it by the
completely coarse rough bark.
E. dives Schau. Broad-leaved Peppermint

This species is a small to medium-sized tree of relatively dry sites for peppermints, often occur-
ring on sunny, northern slopes of hills with shallow, often stony soils. Its natural distribution is
on the tablelands and lower mountains of southeastern Australia. The bark is typical pepper-
mint, i.e. finely fibrous, not coarse and stringy, and is indistinguishable from that of E. radiata.
The juvenile leaves are the most conspicuous element of the species. E. dives regrows readily on
roadsides from lignotubers and the young plants produce many pairs of opposite, ovate, glau-
cous, juvenile leaves. The adult leaves are the broadest for the peppermint group and are lanceo-
late to broadly lanceolate, glossy green.
E. dives belongs to the monocalypts (subgenus Eucalyptus), a large subgenus distinguished by
the axillary inflorescences, buds with a single operculum and seeds that are cuboid, pyramidal or
elongate with a terminal hilum. The peppermints are characterised in the monocalypts by the
many pairs of opposite leaves of the seedling. The buds and fruit are probably the largest for the
peppermints of mainland Australia. The non-glaucous E. nitida J.D. Hook. of Tasmania has
larger buds and fruit.

The secondary venation of the leaves of E. dives is conspicuous and terminates at a distinct
intramarginal vein which is well removed from the edge. A minor, less distinct, intramarginal
vein runs between the principal intramarginal vein and the edge. The reticulation is sparsely to
only moderately dense through lack of tertiary and further veining, the areoles in the broader leaf
being correspondingly larger than those in E. radiata. The oil glands are numerous per areole and
do not appear to be associated with veinlets when the leaf is viewed fresh with transmitted light.
They are approximately circular in outline and mostly green with some white in colour.
Several chemotypes occur in E. dives and there are 1,8-cineole, phellandrene and piperitone
variants. In South Africa, around 150180 t of the piperitone-rich oil was produced annually in
the late 1980s (Coppen and Hone 1992) and although it is no longer used for the production of
menthol, as it once was, it continues to be distilled for flavour and fragrance applications
(J. Coppen pers. comm.).
E. exserta F. Muell. Queensland Peppermint

This is a small to medium-sized tree or mallee belonging to the red gum group. It is notable for
the linear juvenile leaves and hard rough bark. The fruit of the entire red gum group are recog-
nised by the hemispherical base and very prominent raised disc and exserted valves. The seeds of
E. exserta are typical of most of the red gums, e.g. E. tereticornis, in being elongated, black,
toothed around the edges and with a terminal hilum. They contrast strongly with those of the
widely planted red gum, E. camaldulensis, which are yellow and double-coated.
E. exserta is widespread in eastern Queensland, particularly on low stony rises. The red gums
divide into four taxonomic groups distinguished by seed, juvenile leaf, fruit and bark characters.
To the north of its natural distribution the related E. brassiana Blake occurs as far as
New Guinea, while to the south another related species, E. morrisii R. Baker, is endemic to low
rocky hills of western New South Wales.
The leaves of E. exserta are slightly glossy, green to greyish green, and have the typical red
gum pattern of moderately dense reticulation. Tertiary venation is fine with fairly large areoles
and numerous oil glands per areole. Most glands appear round and green when the leaf is viewed
fresh with transmitted light.
E. exserta has been planted in China for many years for its timber and leaf oils.
E. globulus Labill. (four subspecies) Southern Blue Gums

This is one of the most widely cultivated species around the world. Typically, it is a tall, erect
forest tree with mostly smooth bark. The characteristic prolonged juvenile leaf phase is one of its
most notable features, making it one of the easiest eucalypts to identify. In this phase the leaf
pairs remain opposite and sessile to the sapling stage and are conspicuously broad and glaucous.
The adult leaves are strikingly different in being long, falcate, glossy green. The juvenile leaves
are often seen in clear contrast to the adult leaves when they appear as new growth on old
branches within the crown.
E. globulus sens. lat. occurs disjunctly over a wide area of relatively high rainfall parts of south-
eastern Australia. It has created considerable confusion taxonomically, having been variably split
into four or five species. It belongs to the large section Maidenaria, which may be diagnosed by
the concolorous leaves, axillary inflorescences, juvenile leaves sessile and opposite for many pairs,
and seeds prominently lacunose with a ventral hilum. Currently, E. globulus is regarded as four
subspecies, one of which, subsp. globulus from Tasmania and southern, coastal Victoria, is the
principal form grown in other countries.

Tasmanian Blue Gum (subsp. globulus) is one of the few eucalypt species with a single bud to
the inflorescence. The buds are large, sessile, warty and glaucous. The other subspecies are subsp.
bicostata (Maiden, Blakely and J. Simm.) Kirkpatr., which has three buds to the inflorescence and
is distributed in high country from northern New South Wales to southern Victoria, subsp.
pseudoglobulus (Naudin ex Maiden) Kirkpatr., which has three buds to the inflorescence and
occurs in east coastal Victoria and possibly the northern end of Flinders Island in Bass Strait, and
subsp. maidenii (F. Muell.) Kirkpatr., which has seven buds and occurs in coastal hills of eastern
Victoria and far southeastern New South Wales.
The leaves have a moderately dense, fairly distinct reticulation formed by the tertiary and fine
quaternary veinlets between the side veins. The oil glands occur singly or in twos and threes
within the areoles and can be seen with transmitted light through a fresh leaf. The glands are
roughly circular in outline and are mostly green with some white. Some glands touch veinlets or
appear to terminate ultimate veinlets within an areole.
E. globulus is the principal source of eucalyptus oil in the world. It is utilised for such purposes
in China, Spain, Portugal, India, Argentina, Brazil and Chile. The major constituent of the oil is
1,8-cineole.
E. polybractea R. Baker (syn. E. fruticetorum (F. Muell. ex Miq.) R. Baker)

Blue-leaved Mallee
This is the principal species used in Australia for essential oil production. It is a mallee, natu-
rally adapted to relatively low rainfall and infertile soils on plains and low hills inland from the
Great Dividing Range in Victoria and New South Wales. As a mallee it matures as a tall, multi-
stemmed shrub. It has fibrous rough bark over the lower part of the stems and the leaves are
bluish or greyish green. The juvenile leaves are opposite for a few pairs, then alternate, shortly
petiolate, lanceolate to linear, green or greyish green in colour. Adult leaves are notably bluish.
The inflorescences are terminal panicles.
E. polybractea belongs to the box group of eucalypts, most of which are characteristically
rough-barked and have terminal inflorescences. The boxes divide into tree forms and mallees.
Among the latter, E. polybractea is closest to Green Mallee, E. viridis, which occurs over a similar
distributional range. Green Mallee is distinguished by the green, glossy leaves, which are linear
and held erect.
The leaf venation of Blue-leaved Mallee is common to many box species and quite different
from monocalypts and Maidenaria species. The side veins are very acute, particularly towards the
base of the leaf. Intramarginal veins are present while tertiary veining is dense, somewhat
obscure and erose, resulting in elongated, oblique areoles which accommodate many discrete oil
glands (Figure 1.22). There is no clear reticulation outside the intramarginal veins. The glands
are large and very irregular in outline.
Australia is the only country which utilises E. polybractea for oil production, relying as it does
mainly on cleaned areas of natural stands, supplemented by modest areas of plantations. The
centres of production are at West Wyalong in western New South Wales and near Inglewood in
northern Victoria.
E. radiata Sieber ex Spreng. (syn. E. australiana Baker & Smith, E. phellandra Baker & Smith)
Narrow-leaved Peppermint
This species is typically a small to medium-sized tree of relatively dry forests and woodlands.
The bark is rough over the whole trunk, fibrous and interlaced, though not as coarse as in the

Figure 1.22 Leaf of E. polybractea showing dense, obscure reticulation and numerous, very irregular oil
glands, both features typical of the mallee boxes.
stringybarks. The juvenile leaves remain opposite for many pairs, are sessile, lanceolate and
green. In morphology the young plants resemble E. viminalis, which may grow naturally in the
vicinity, but the two species can be distinguished by the stronger fragrance, emanating from
the more abundant oil glands, and by the reduced amount of leaf reticulation in E. radiata. The
mature crown is usually dense and attractive with small, narrow leaves which are green to dark
green and glossy.
Narrow-leaved Peppermint is a monocalypt (subgenus Eucalyptus) and belongs to one of the
taxonomically most difficult groups in this subgenus. Most peppermints are relatively narrow-
leaved and the common name mainly has relevance to the contrasting, broader-leaved, E. dives.
Baker and Smith (1915) published a new species, E. australiana, which they considered was a
mainland form of the otherwise Tasmanian endemic, E. amygdalina Labill. They were apparently
unaware that the long established name, E. radiata, accounted for their new species in conven-
tional morphological terms. Blakely (1934) stated that E. australiana yields an excellent phar-
maceutical oil far superior to that of E. radiata, due mainly to the presence of a large amount of
cineole. This nomenclatural anomaly illustrates the problem of trying to establish taxa from dif-
ferences in their chemistry alone. While the chemical species may be disregarded from the
purely taxonomic point of view, it emphasises that provenance is an important aspect in assess-
ing the value of a species for oil production. E. phellandra, another mainland taxon, is similarly
regarded now as a high-phellandrene form of E. radiata.
One other accepted taxon has been conventionally associated with E. radiata, namely, E. robertsonii
Blakely. Over the relatively wide natural distribution of E. radiata, populations extend from the
typical tableland regions to the mountains of far southeastern New South Wales. Here, the
species takes on a taller habit, the leaves are somewhat bluish and the buds are slightly glaucous.
This form was reduced to a subspecies of E. radiata ( Johnson and Blaxell 1973) but later rein-
stated as a species in its own right ( Johnson and Hill 1990). In the latter paper Johnson and Hill
split typical E. radiata and erected the northern form as E. radiata subsp. sejuncta. The new taxon

differs from subsp. radiata by the broader juvenile leaves and appears to be richer in "-pinene
than 1,8-cineole (Brophy unpubl.).
The inflorescences of the peppermints invariably have more, often many more, than seven
buds. These are pedicellate, clavate, and minutely warty. The fruits usually have a thick rim and
a conspicuous reddish brown disc. A peppermint species with which E. radiata may be confused
is E. elata, the River Peppermint, which has only the basal part of the trunk rough and has very
numerous buds such that the flowers are a characteristic ball of white. A peppermint species
with notably narrower leaves, and a favoured ornamental, is E. pulchella Desf., which is a
Tasmanian endemic and mostly smooth-barked.
The leaf reticulation in E. radiata is sparse with the side veins at a prominently acute angle
(#30 to the midrib). There is usually an inner strong and outer weak intramarginal vein. This
overall pattern is typical of the peppermints, although E. willisii from southern, coastal Victoria can
have side veins parallel to the midrib, as seen in snow gums, e.g. E. pauciflora. The oil glands occur
many to an areole without obvious association with the veinlets. The glands are roughly circular in
outline and a mixture of green and white in colour when viewed fresh with transmitted light.
E. radiata was once exploited in Australia for oil production, and still is to a small extent.
It is also grown for this purpose in a small way in South Africa and has shown promise in
other parts of Africa such as Tanzania ( J. Coppen pers. comm.). There are several recognised
chemotypes. Boland et al. (1991) cite two, one being rich in 1,8-cineole and the other in
phellandrene/piperitone. Recent commercial interest has focused on the cineole-rich form.
E. smithii R. Baker Gully Gum

This is a medium-sized to tall, erect forest tree of southeastern Australia, where it occurs on the
coastal plains and in valleys of the eastern fall of the Southern Tablelands of New South Wales.
Small mallee forms are found on very rocky crags of mountain country of far eastern Victoria. In
habit and bark the trees are easily confused with the unrelated E. badjensis Beuzev. & Welch and
E. elata in that all three are tall trees with basal, compacted, brown-black rough bark. Juvenile
leaves are also similar, being sessile, opposite, lanceolate and green for many pairs. However,
inflorescences clearly differentiate the three: E. smithii is 7-flowered, E. badjensis is 3-flowered
and E. elata has many more than 7 flowers.
E. smithii is classified in the section Maidenaria which divides into two large groups, one
3-flowered and the other 7-flowered. It is difficult to associate it taxonomically with any other
species to establish natural affinity, although it has superficial similarities to the two mentioned
above.
The leaves of Gully Gum are usually long and narrow. Side veins are clear with lesser side
veins running more or less between. The intra-veinal zone is broken by relatively weak tertiary
veinlets and some even less distinct quaternary veinlets. Oil glands are fairly numerous, one to
few per areole, without giving the immediate impression that the leaves are highly glandular.
The glands are green and yellowish.
E. smithii is widely grown in South Africa for timber purposes and in the eastern Transvaal it
is harvested for cineole-rich leaf oil (Coppen and Hone 1992).
E. staigeriana F. Muell. ex Bailey Lemon-scented Ironbark

This is a small to medium-sized tree, usually of poor form in its natural habitat which is granite
or sandstone hills of Cape York Peninsula in far northern Queensland. The bark is typical

ironbark, i.e. hard, black and furrowed. The crown is conspicuously bluish due to the blue-green
to glaucous, usually broad, adult leaves. The inflorescences are terminal panicles. Buds and fruit
are small and inconspicuous.
The numerous ironbark species belong to three taxonomic groups. E. staigeriana is in the
largest group which is distinguished by the early loss of the outer operculum and stamens which
are all fertile. Both of these characters contrast with the buds of the better known ironbark
species, E. sideroxylon.
The adult leaves are relatively small with very dense reticulation formed by the tertiary and
quaternary veining. The oil glands are of two types, either small, green and single in the areoles
(some areoles lacking glands) or fewer, larger and whitish, occurring at the intersections of
quaternary veinlets.
E. staigeriana is one of two eucalypt species that are notable for their lemon-scented oils (see
E. citriodora above) and is cultivated for the production of citral-rich oil, chiefly in Brazil. Weiss
(1997) states that it is also grown for such purposes in Guatemala, the Seychelles and the former
Zaire (now the Democratic Republic of the Congo).
Species of lesser importance or with potential for essential oil production
E. camaldulensis Dehnh. River Red Gum

This is the most widespread species in Australia and one that is cultivated throughout the world
in tropical and subtropical regions. It is notably a species of freshwater stream banks, whether of
the major rivers or the inland rivers which only flow after heavy rain. It frequently has a heavy
butt and widely spreading crown. Basically a smooth-barked species, it usually has an accumu-
lation of unshed or imperfectly shed rough slab bark on the bottom 1 m of the trunk. As with all
the red gums, the juvenile leaves are petiolate and only the first 4 or 5 pairs remain opposite. In
River Red Gum the juvenile leaves are lanceolate, which contrast with the ovate leaves of most
of the related species. The adult leaves are mid-green, slightly bluish green or yellowish green
and vary from dull to slightly glossy.
E. camaldulensis belongs to the large series Exsertae and, as might be expected in a species
of such widespread natural distribution, there is considerable variation in morphological
characters. This has been recognised in the taxonomic treatment which has resulted in
many named varieties. The principal split, which is recognised today more for convenience
than any fixed morphological distinction, is into two varieties, var. camaldulensis, which is the
form of the Murray-Darling river systems of southeastern Australia, most easily distinguished
by the strongly beaked operculum, and var. obtusa Blakely, which is the name loosely
applied to all other provenances, the name referring to the obtuse operculum. The seeds are
distinctive in being yellow to yellow-brown, cuboid and having a double seedcoat and terminal
hilum.
The leaf reticulation in River Red Gum is moderately dense in southern Australian occur-
rences while the northern River Red Gums have a denser, more closed pattern. The quaternary
veining is relatively weak and ultimate fine veinlets may appear to end within an areole, such
that the overall pattern is not finite. Oil glands are usually numerous and conspicuous and may
be several per areole in leaves of southern provenances, becoming fewer per areole in northern
specimens. The glands are approximately circular in outline and are usually a mixture of green,
yellow and white when viewed fresh with transmitted light (Figure 1.23). Very rarely do the
leaves appear glandless.

Figure 1.23 Leaf of E. camaldulensis showing dense reticulation and island oil glands, both features
typical of the red gums.
It is likely that there are many chemotypes. One well-known provenance, Petford in northern
Queensland, for example, has two forms, one rich in 1,8-cineole and the other in sesquiterpenes.
Because of its widespread cultivation it may well become a future source of eucalyptus oil.
E. cinerea F. Muell. ex Benth. Argyle Apple

This is one of the most widely planted ornamental eucalypts in southern Australia. It is consid-
ered highly attractive for its mature crown of glaucous, ovate juvenile leaves, and is also much
favoured in dried flower arrangements. It is only one of several species, however, that are repro-
ductively mature in the juvenile leaf phase. It is one of the mostly easily recognised eucalypt
species by the combination of the grey crown and thick, reddish brown, completely rough bark.
It is further distinguished by its 3-flowered inflorescences and funnel-shaped fruits.
Argyle Apple belongs to the large section Maidenaria, many species of which are 3-flowered.
From a distance it could only be confused among species of southern Australia with E. risdonii
J.D. Hook., one of the completely unrelated monocalypts (subgenus Eucalyptus) which is easily
distinguished on closer inspection by the connate leaf pairs. Species of northern Australia may

have similar crowns to E. cinerea, e.g. E. melanophloia F. Muell., which is an ironbark with an
entirely different hard, furrowed, rough bark, and E. pruinosa Schauer, which has much larger
leaves and terminal inflorescences.
The side veins of the leaves of E. cinerea meet the intramarginal vein at indentations, the intra-
marginal vein itself being well removed from the leaf edge. With the side veins the tertiary vein-
ing makes distinctive polygons which are themselves divided within by fine quaternary veining
to form the ultimate areoles. Within the areoles the oil glands are one to few, small, whitish and
mostly discrete, with some contiguous to the veinlets.
The leaves of E. cinerea contain a cineole-rich oil and it was once used for oil production in
Australia. It has recently been cultivated for such purposes in Zimbabwe (Boland et al. 1991)
although production has only amounted to a few tonnes annually (Coppen and Hone 1992).
E. kochii Maiden & Blakely subsp. kochii (Maiden & Blakely) Brooker Oil Mallee
This is a small to medium-sized mallee found only in the northern wheatbelt of Western
Australia where it occurs largely as roadside remnants of once dense mallee scrub. The bark is
rough. The dull, bluish grey, lanceolate juvenile leaves contrast with the glossy green, linear to
narrowly lanceolate adult leaves which make up a dense crown of shining foliage.
E. kochii belongs to a large taxonomic series that occurs widely in southern Australia in relatively
dry country, although most of the species are concentrated in the west of the continent. E. kochii
consists of two subspecies in the Western Australian wheatbelt and adjacent arid country: subsp.
kochii, which is the typical, western form, rich in 1,8-cineole, and subsp. plenissima, the eastern form,
which extends into desert areas and has a much lower oil content despite the subspecific name.
The tertiary veining of E. kochii forms a dense, finite reticulum. The oil glands are very
numerous and large, are irregular in shape and appear at the intersections of the veinlets
(Figure 1.19).
Oil Mallee is currently being tested as a producer of 1,8-cineole by the CSIRO and the New
South Wales Department of Agriculture at Condobolin in mid-western New South Wales. Early
results show that E. kochii maintains a high production of 1,8-cineole per unit weight of leaf, but
it is likely that the species will only produce sufficient biomass on soils which are lighter than
those where the trial is being conducted (Milthorpe et al. 1998).
E. olida Johnson & Hill

This is a small to medium-sized tree, recently discovered and rare, known only from two natural
populations on the Northern Tablelands of New South Wales. It is rough-barked, has prominently
petiolate, broadly ovate, pendulous, dull blue-green juvenile leaves. The adult leaves are dull to
slightly glossy, green to grey-green. There are usually many clavate flower buds per inflorescence.
E. olida belongs to the blue ash group of species (in subgenus Eucalyptus), so named from the
colour of the juvenile leaves, which contrasts with the bright green juvenile leaves of the green
ash species, e.g. E. obliqua. It shares the tight, grey, fibrous bark of E. andrewsii Maiden, the blue
ash species common in the same part of New South Wales.
The leaves are sparsely to moderately reticulate with very acute side veins typical of the ash
group. The areoles are often indistinct due to the indeterminate tertiary veining. Oil glands are
numerous per areole.
The discovery of E. olida aroused considerable interest when it was found to contain a high
proportion of E-methyl cinnamate in the leaves, and the species is now exploited commercially
as a source of the chemical in Australia.

Acknowledgements
I am grateful to Garry Brown for production of the Figures and Kirsten Cowley for preparing
the data for Figure 1.1.
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2 Eucalyptus, water and
the environment
Ian R. Calder
Environmental concerns about eucalyptus

Traditionally, foresters have always believed their forests to be a benign influence on the
environment. Sure in this belief, forestry programmes have been advocated, even where there are
little or no commercial returns from the forests, solely for their environmental benefits.
Yet not everybody shares the foresters sanguine views, especially when forestry plantations
contain fast growing trees such as eucalypts. In many parts of the world concerns have been
expressed over the environmental and social effects of large scale planting of eucalypts for indus-
trial and social forestry applications. One of the key issues in this controversy concerns the hydro-
logical effects of the afforestation. Essentially these fears are, as expressed in India by Vandana
Shiva et al. (1982) and Vandana Shiva and Bandyopadhyay (1983, 1985), that eucalypts are vora-
cious consumers of water and are likely to deplete water resources. When one considers that there
are many well documented reports that eucalypts have been used to drain marshes near Rome in
the eighteenth or nineteenth century (Ghosh et al. 1978), and in Uganda (see Nshubemuki and
Somi 1979) and in Israel (Saltiel 1965) in the twentieth century and that eucalypt plantations
are currently being used as water pumps to deliberately lower water tables in parts of Australia
that are experiencing salinity problems (Greenwood 1992), it is easy to understand how these
fears have arisen.
In the absence of hard evidence to the contrary, speculation by the press and by some local
environmental groups raised the controversy to such a pitch that in parts of Karnataka state in
southern India farmers ripped out eucalyptus seedlings from government nurseries and planta-
tions. Yet other farmers in Karnataka saw eucalypts as beneficial they viewed them as a valu-
able source of income and were keen to plant them on their fields. And eucalyptus trees can have
other environmental and economic benefits. As providers of a fast-growing source of timber,
firewood and pulp they can help to reduce the pressure on the few remaining indigenous forests
as wood sources and thus aid conservation efforts. Through saving foreign exchange on the
importation of pulp they have obvious economic benefits. On a very much smaller scale, bene-
fits, welcome nonetheless, accrue to the pharmaceutical and fragrance industries in India (and
elsewhere) from the production of eucalyptus oil. However, an article in a popular weekly science
magazine in 1988, The tree that caused a riot ( Joyce 1988), illustrates clearly the uncertainty
and the worries that existed at that time.
To some extent the publication of recent research findings on the environmental impact of
eucalyptus plantations in India has defused the conflict situation between foresters and environ-
mentalists. Yet although some of the worries of the environmental groups may have been without
substance it is clear now that the foresters conceptions of the benefits of these plantations were
also often flawed.

In South Africa, eucalyptus plantations have also been the centre of a controversy which has
revolved around the question of water use. Here, eucalypts are generally planted on the wetter
hills and the concern is that less water is then available for supply to industries and mines, farm-
ers downstream who want water for irrigation, and, often further downstream, the game parks
and nature reserves which require minimum flows in the rivers to sustain wildlife and the local
ecology. South Africa has carried out some of the most detailed and definitive studies of water
use from forests and commercial eucalypt plantations of any country in the world. The results
have not suffered obfuscation through water interests and forestry interests residing in
different government ministries since, in South Africa, both reside within the Department of
Water Affairs and Forestry. This has led to an innovative approach to land and water manage-
ment and proposals that land uses with a high water requirement such as forests and sugar cane
plantations should be subject to an interception levy in compensation for the water that would
otherwise be available under different land uses.
In both India and South Africa, and also in other countries with a high proportion of eucalypt
plantations, the pressing question is not so much What are the environmental impacts? but
How can these plantations and other land uses be managed in an integrated and sustainable
manner to the benefit of economics, socio-economics, the ecology and the water resources of the
basin and basin inhabitants?.
This chapter reviews some of the myths that are still being propagated in relation to the
impacts of forests on the environment and the research that has been carried out in India and
South Africa on the impacts of eucalypt plantations. It also outlines the new approach that is
being developed worldwide to manage land and water resources in an integrated way. Although
little of the research has been directed specifically at eucalypts being grown for medicinal or per-
fumery oils (or any other extractive), all of what is discussed here has relevance to such situations.
In many cases the species used for oil production are similar, or identical, to those used for timber
and pulp and the research findings would be expected to be equally applicable. Where waste leaf
from eucalypts felled for pulp is distilled then this will certainly be true. Where oil production is
achieved through harvesting of trees which are still growing, however, this will result in a
decrease in leaf area of the living trees, and it would be expected that growth rates, transpiration
rates and interception losses would all be decreased. Water use from these plantations would then
be expected to be significantly less than those from plantations grown for timber or pulp, which
would have more extensive canopies. Although the author is not aware of any studies which have
quantified this effect they would, in principle, be easy to carry out through the application of
modern measurement technologies and modelling methods.
Forest hydrology myths

There still remains much folklore, and many myths, about the role of forests and their relation-
ship with the environment and hydrology which hinders rational land use decision-making.
Foresters have sometimes been suspected of deliberately propagating some of these forest hydrol-
ogy myths. Pereira (1989) states:
The worldwide evidence that high hills and mountains usually have more rainfall and more
natural forests than do the adjacent lowlands has, historically, led to confusion of cause and
effect. Although the physical explanations have been known for more than 50 years, the
idea that forests cause or attract rainfall has persisted. The myth was created more than a
century ago by foresters in defence of their trees The myth was written into the text-
books and became an article of faith for early generations of foresters.

The overwhelming hydrological evidence supports Pereiras view that forests are not generators
of rainfall yet this myth, like many others in forest hydrology, may contain a modicum of truth
that prevents it from being totally laid to rest. The oft propagated views that forests increase rain-
fall and that forests increase runoff, regulate flows, reduce erosion, reduce floods, sterilise water
supplies and improve water quality, when scrutinised (Calder 1996, 1998, 1999), are mostly seen
to be either exaggerated or untenable. For some we still require research to understand the full
picture.
In relation to eucalyptus plantations, the principal concerns have been about their effects on
total runoff and low flows and on erosion. Some of the research that has been carried out to inves-
tigate these relationships, which is now providing the scientific evidence which can replace the
former folklore and beliefs which have for so long bedevilled rational land use decisions, is
reviewed below. The review focuses mainly on studies in Australia, India and South Africa which
have used both detailed process-based measurements carried out at the plot scale and measurements
at the scale of whole catchments.
Eucalytpus, evaporation and runoff
Evaporative processes
It is convenient to differentiate the total evaporative loss from vegetation into its two principal
components, interception and transpiration. This is because the processes involved are essen-
tially different. Interception, the evaporation of water from the wet outer surfaces of leaves dur-
ing and after rainfall, is simply a physical process, whereas transpiration, which involves the
uptake of water by plant roots and transfer through the leaves, involves physiological processes,
and is thus subject to much more complex control mechanisms.
Rainfall interception by eucalypts

Evaporative losses of intercepted water occur both during the rainfall event itself and afterwards,
from water stored on the leaves, branches and trunks of trees, when they are then constrained by
the water storage capacity of the vegetation.
The average evaporation rates from wet trees tend to be much higher, say 25 times, than those
from wet, shorter vegetation (Calder 1979, 1990) because they present a relatively rough surface
to the wind and are more efficient in generating the forced eddy convection which, under the
majority of meteorological conditions, is the dominant mechanism responsible for the vertical
transport of water vapour from the leaves into the atmosphere. Little information is available on
differences between species with respect to evaporation rates under wet conditions and it is usually
assumed that evaporation rates from wet vegetation of the same height are similar, irrespective
of species.
The leaf interception storage capacity, however, a function of the leaf surface area and its
water-holding capacity, does vary widely between tree species. The highest storage capacities
have been reported for tropical rainforest trees (Herwitz 1985), although it is believed that
these high storages are largely caused by storage on the woody parts (trunks and branches) of
these tall trees. Eucalyptus spp. are likely to fall into the lower end of the range of tree storage
capacities.
In regions with relatively high intensity, short duration storms (i.e. tropical monsoon or con-
vective storms, as opposed to relatively low intensity, long duration storms typically associated
with frontal rainstorms) it is expected that the proportion of intercepted water lost during

Table 2.1 Comparative interception ratios from Eucalyptus and other tree speciesa
Location Species Average annual Interception Reference

rainfall (mm) (% of rainfall)
India (Dehra Dun) E. hybrid 1670 12 George 1978

Pinus roxburghii 1670 27 Dabral and Subba
Rao 1968
India (Nilgiris) E. globulus 1150 22 Samraj et al. 1982
Acacia mearnsii 1150 25 Samraj et al. 1982
Shola forest 1150 34 Samraj et al. 1982
Israel E. camaldulensis 700 15 Karschon and Heth 1967
Australia E. regnans 810 11 Smith 1974
(Lidsdale, NSW) Pinus radiata 810 19 Smith 1974
Australia E. obliqua 1200 15 Feller 1981
(Maroonda, NSW) Pinus radiata 1200 25 Feller 1981
E. regnans 1660 19 Feller 1981
a Brookes and Turner (1964), Duncan et al. (1978), Prebble and Stirk (1980), Dunin et al. (1988) and Westman (1978)
have reported interception ratios from eucalypts in Australia in the range 1123 per cent but they did not give values
from other tree species to allow comparisons to be made under the same climatic regimes.
rainfall is small compared with that lost from storage after the cessation of rainfall. Interception
losses will therefore be primarily determined by canopy capacities and it is reasonable to expect
that they will, under these circumstances, be lower from Eucalyptus spp. than from other tree
species. This conclusion is supported by the results of many interception studies carried out in
India and Australia (Table 2.1).
Rain drop size is important since it affects the wetting response of, and interception losses
from, vegetation (Calder et al. 1986). Up to ten times as much rain may be required to achieve the
same degree of canopy wetting for tropical convective storms, with large drop sizes, than would
be necessary for the range of smaller drop sizes usually encountered for frontal rain (in, say, the
UK). Vegetation type is also important in determining the wetting response since large-leafed
vegetation would be expected to generate larger drop sizes than smaller leafed, and these large
drops would be relatively inefficient in wetting up lower layers in the canopy. Results from stud-
ies using rainfall simulators also show that the final degree of canopy saturation varies with drop
size, being greater for drops of smaller size. Eucalyptus species, with average sized leaves, are also
about average in terms of their wetting up response and canopy storage, and also in terms of their
effects on splash-induced erosion (see later).
Transpiration from eucalypts

Transpiration losses from Eucalyptus spp., as for most other vegetation types, are determined
principally by
1 Climatic demand which is related to the prevailing radiation, atmospheric humidity

deficit, temperature and wind speed.
2 Physiological response mechanisms which control stomatal apertures the small pores in the
leaf surface in response to environmental conditions (both past and present). Of particular
importance are the mechanisms which close stomata in response to increasing soil water
stress and increasing atmospheric humidity deficits. These mechanisms have been shown to

operate on a number of plant and tree species, both on leaf scale (e.g. Lange et al. 1971) and
on tree and forest scale (e.g. Jarvis 1976, Stewart and de Bruin 1983).
3 Canopy structure, particularly leaf area index.
4 Availability of soil water to the roots.
A knowledge of the stomatal response mechanisms, together with a knowledge of rooting

patterns and soil water availability, is therefore crucial to the understanding of water use and
water use efficiency in any particular environment.
Research findings from Portugal and Western Australia
Physiological controls
Pereira et al. (1986, 1987) carried out studies of the water relations and water use efficiency of
Eucalyptus globulus trees growing at a site in Portugal. This species is widely grown in Portugal for
pulp and waste leaf from the felled trees is sometimes distilled for oil. They found that both photo-
synthetic carbon assimilation and leaf water use efficiency were highest in the spring, reduced
in winter and lowest by mid-summer when severe drought conditions prevailed. The maximum
rates of net photosynthesis were higher than most values reported for temperate zone woody
plants (Korner and Cochrane 1985), slightly higher than those reported for E. pauciflora in its nat-
ural habitat in southern Australia (Slatyer and Morrow 1977), but broadly similar to those for
E. microcarpa in New South Wales (Attiwill and Clayton-Greene 1984). Pereira et al. (1986) also
found that E. globulus was effective in controlling water loss when the evaporative demand of
the air was greatest. Maximum diurnal transpiration occurred at the time of maximum vapour
pressure deficit in winter, but before maximum vapour pressure deficits were reached in summer.
Physiological and water use studies

The water use and physiological studies of Eucalyptus spp. carried out in Western Australia are
among the most detailed and comprehensive process studies carried out on any group of tree
species. This is also a region where large scale planting of oil-bearing eucalypts is currently being
undertaken with a view to controlling salinity, while at the same time producing an economic
return through oil production (Bartle 1994). The results of these studies are therefore very relevant
to such operations although they are not always easy to interpret. What is certain is that not only
do different Eucalyptus spp. show very different stomatal response mechanisms, but rooting pat-
terns may also vary widely between species and between sites. Furthermore, at sites where roots are
able to extract water directly from shallow water tables, very high transpiration rates may result.
Colquhoun et al. (1984) carried out detailed studies on the daily and seasonal variation of
stomatal resistance and xylem pressure potential in E. marginata and E. calophylla, the two major
tree species of natural jarrah forest, and four other Eucalyptus species which were being used for
reforestation. They found that the physiological responses exhibited by these different species,
which all experienced the same meteorological conditions and were growing in close proximity,
could be classified into three types:
1 E. marginata and E. calophylla showed little stomatal control of water loss and leaf resis-
tances remained low throughout the study period. There was no evidence that stomatal
resistance was correlated with atmospheric vapour pressure deficit.

2 E. maculata, E. resinifera and E. saligna all showed some stomatal control. For a typical
summer day, stomatal resistances were low in the morning but increased through the day,
broadly in line with increasing vapour pressure deficit (and atmospheric demand).
However, no causal relationship was established and the stomatal regulation may have been
caused by other factors.
3 E. wandoo exhibited stomatal control (as in 2 above) but also developed xylem pressure
potentials far lower than all other species studied. The authors inferred that this species,
which originated from the lower rainfall and shallower soil regions of the Darling range in
Western Australia, may have been able to impose higher root suctions and extract more
water from the soil than the other species studied.
Carbon et al. (1981), in a study of water stress and transpiration rates from natural jarrah for-
est growing in five different catchments in the Darling range, found little difference between
E. marginata and E. calophylla in their transpiration responses (subsequently confirmed by
Colquhoun et al. 1984) and little difference between sites, except in late summer when transpi-
ration rates were generally higher from sites with permanent water tables. In another study,
Carbon et al. (1982) found that on the Swan coastal plain, Western Australia, Pinus pinaster plan-
tations consumed the most water, water use by the perennial pasture and native jarrah forest was
similar but less than that of the pines, and annual pasture used the least.
Greenwood and Beresford (1979) investigated the transpiration rates from individual juvenile
trees of different Eucalyptus spp. planted at three different sites in different rainfall regimes in the
Hotham valley, southeast of Perth, Western Australia. They found considerable variation in rates
between species at different sites and the species with the highest rate was different at each site:
E. globulus was highest at Bannister, the 850 mm (annual rainfall) site, E. cladocalyx at Dryandra,
the 500 mm site, and E. wandoo at Popanyinning, the 420 mm site. Interestingly, they also inferred
that, because at Popanyinning the average transpiration per unit leaf area over all species had
increased three-fold between early and late summer, the roots of the two-year-old trees had reached
the water table which was at a depth of between 3 m and 5 m.
On the other hand, Greenwood et al. (1982) reported results of evaporation studies on a regen-
erating forest of E. wandoo on land which had formerly been cleared for agriculture (at the
Bingham river site near Collie in southwest Australia) and found that the uptake of water by the
trees was limited mainly to the unsaturated zone and that the trees did not extract a substantial
quantity of water from the phreatic aquifer. The water table was located at a depth of approxi-
mately 9 m at this site and subsequent excavations showed that no large roots penetrated deeper
than 1.2 m. They concluded that neither the regrowth rooting system nor that of the original
forest could have penetrated far enough to draw water from the aquifer.
Greenwood et al. (1985) have reported further studies on what were then seven-year-old trees,
at Bannister, the high rainfall site in the Hotham valley. The studies were made on two planta-
tions, one upslope of, and the other immediately above, a saline seep. Annual evaporation
from pasture in that area was 390 mm regardless of the position on slope. Annual evaporation
(interception plus transpiration) from trees at the upslope site was 2300 mm for E. maculata
and 2700 mm for both E. globulus and E. cladocalyx; at midslope the values were 1600 mm for
E. wandoo, 1800 mm for E. leucoxylon and 2200 mm for E. globulus. They concluded that to
support these high rates, which exceeded the annual rainfall of 680 mm by about a factor of four,
the trees must be extracting water directly from groundwater. Soil coring studies which revealed
roots at 6 m, 1 m below the water table, supported this hypothesis. (N.B. evaporation rates of
this magnitude exceed the rate that can be supported by the input of solar radiation alone and

imply considerable advection of heat from the air mass moving over the forest; this is indeed
possible and has been verified for wet forests, see Calder 1985.)
Research findings from India
Water use studies

To answer the questions raised about the environmental impacts of fast growing tree plantations,
and to devise ways in which some of the adverse effects could be minimised, studies of the
hydrology of eucalyptus plantations, indigenous forest and an annual agricultural crop have been
carried out in Karnataka (see Calder 1994 for a summary of the findings). Measurements were
made at four main sites of the meteorology, the plant physiology, soil water status, rainfall inter-
ception and the direct water uptake of individual trees using tracing measurements.
Measurements were also made of the growth rates of the trees. A deuterium tracing method,
developed during the project, proved to be a very effective and powerful method for determining
transpiration rates of whole trees and revealed a surprisingly tight and simple relationship
between the individual tree transpiration rates for young eucalypts and the cross-sectional areas
of their trunks. This in turn led to a simple water use and growth (WAG) model (Calder 1992)
that is applicable in India and other water-limited parts of the semi-arid tropics. The WAG
model provides a framework for the estimation of the water use from eucalyptus plantations in
relation to age, spacing and growth rate.
The model also provides a framework for investigating the mechanisms that control the
growth rates of the plantations in relation to water use, what is termed the water use efficiency.
Through assignment of values, based on marginal costs, of the water consumed and the value per
unit volume of the timber produced it is possible to assess the economic returns of the plantation
set against the real costs of the water consumed. These water use calculations need also to build in
interception losses and any other losses from the understorey or bare soil beneath the tree canopy.
One feature of eucalyptus plantations is that although water consumption is high, transpirational
water use efficiency is also high, so that for a given amount of water transpired the volume of tim-
ber produced is probably as high as that from any tree species. Bearing in mind that interception
losses and understorey losses are essentially a fixed overhead loss per year, not usefully employed,
the high growth rates of eucalyptus species mean that these overheads are a small proportion of
the total water consumed. On a plot basis the water use efficiency is probably as high, if not
higher, than that of any other tree species.
The recognition that water is a valuable resource in its own right, and that forests generally
evaporate more water than other crops, provides a powerful incentive for trying to improve the
water use efficiency of plantation forests. Both growth rates and water use efficiency of eucalyp-
tus plantations in the dry zone in India are low by world standards. To some extent climatic
factors, which are not amenable to manipulation, are responsible for the low water use efficien-
cies. Nevertheless, it is believed that there is still great potential for improvements through,
for example, species selection, removing nutrient and water stress, and improved silvicultural
practices such as optimal spacing and weeding.
In experiments carried out within a Controlled Environment Facility at Hosakote, near
Bangalore, Eucalyptus camaldulensis, E. grandis and an indigenous species, Dalbergia sissoo, were
grown under different conditions of water and nutrient stress. Results from the first two years of
the experiment showed up to five-fold increases in growth rates on plots which received both
water and fertiliser treatments compared with the control plots. Although water applications

alone lead to large increases in growth rate there was no evidence to show that purely transpira-
tional water use efficiency was improved (Calder et al. 1993).
Water resource implications

The hydrological studies carried out in southern India on plantations of exotic tree species,
indigenous forest, and an agricultural crop showed a varied and complex pattern of hydrological
impacts. The results can be summarised as follows:
1 At two of the dry zone sites, the water use of young Eucalyptus plantation on medium depth
soil (3 m) was no greater than that of the indigenous dry deciduous forest.
2 At these sites, the annual water use of eucalyptus and indigenous forest was equal to the
annual rainfall (within the experimental measurement uncertainty of about 10 per cent).
3 At all sites, the annual water use of forest was higher than that of annual agricultural crops
(about two times higher than finger millet).
4 At the dry zone site which had deep soil (!8 m), the water use, over the three (dry) years of
measurement, was greater than the rainfall. A later experiment showed that Eucalyptus
camaldulensis roots can penetrate the soil at a rate exceeding 2.5 m per year and are able to
extract and evaporate an extra 400450 mm of water in addition to the annual input of
rainfall (Calder et al. 1997). Observations in South Africa (Dye 1996) also confirm deep
rooting behaviour in E. grandis.
5 Unlike the Australian studies referred to earlier (Greenwood et al. 1985) there was no evi-
dence of root abstraction from the water table at any of the sites.
6 Although the water use of eucalyptus plantations is much higher than that of other tree
species, the water use efficiency, expressed on a plot basis, is also much higher. For the same
amount of water consumed, on a plot basis, a greater return in terms of useful biomass will
be achieved from the eucalyptus plantations.
Sustainable management systems

From the research experience outlined earlier, it is suggested that the potentially adverse aspects
of plantation forest practices can be curtailed through adoption of the following:
1 Rotation Where soil water mining occurs (i.e. where the roots penetrate successively
deeper layers in the soil from the day of planting) one strategy which might prove advanta-
geous, particularly on deep soils, would be to rotate Eucalyptus plantation with agricultural
crops. A five-year period under an agricultural crop should allow the soil water reserves,
depleted by say ten years of forestry, to be replenished. From studies in other arid zones of
the world, there is evidence that deep-rooted trees bring nutrients from deep soil layers to
the surface. If this is true of eucalyptus species in India, then there would be dual benefits
from rotation: the trees would replace nutrients the agricultural crops remove, whilst the
agricultural crops would replace water that the trees have removed.
2 Patchwork forestry The forest water use results indicate that recharge to the groundwater
under large areas of either plantation or indigenous forest in the dry zone in India is likely to
be small and will not, on average, be more than 10 per cent of the rainfall. However, if plan-
tation forests were grown as a patchwork, interspersed with annual agricultural crops, many
of the adverse effects on the water table would be alleviated as up to half the annual rainfall
should be available for recharge under the agricultural crops.

3 Irrigation In theory it would be possible to optimise a patchwork design with irrigated
areas of forestry. It should be possible to grow the same volume of timber, using irrigation,
on one-fifth to one-tenth of the usual land area, leaving the rest for rainfed agriculture. There
may also be economic advantages of this type of scheme. If eucalypts grown for pulp were
located close to the pulp mills transport costs would be minimised and this should substan-
tially reduce production costs.
Catchment studies in South Africa

In South Africa, commercial forests consist almost entirely of exotic species, principally pines
and eucalypts, and form a large and important industry with plantations occupying around
1.2 m ha (Bands et al. 1987). However, the forests require at least 800 mm of rain to grow at eco-
nomic rates but only 20 per cent of the country receives this amount and most of this is in
mountainous areas. These mountainous areas are therefore under pressure both for afforestation
and for water gathering. For such a water-short country as South Africa, with an average annual
rainfall over the whole country of only 400 mm, the provision of water from the uplands, maxi-
mal in quantity and quality, is of vital concern. Nowhere are the conflicts between forestry and
water interests more extreme than in South Africa.
Understanding of the interrelationships between land use, hydrology and the environment is
essential for the sustainable and multi-use management of South Africas mountainous areas and a
hydrological research programme centred at Jonkershoek is providing that understanding.
Catchment studies have provided unequivocal evidence for the reductions in streamflow that will
occur as a result of afforestation with commercial eucalyptus and pine species (Bands et al. 1987).
The studies also destroy the foresters myth of forests attracting rain. Quoting from Bands
et al. (1987):
Forests are associated with high rainfall, cool slopes or moist areas. There is some evidence
that, on a continental scale, forests may form part of a hydrological feedback loop with
evaporation contributing to further rainfall. On the Southern African subcontinent, the
moisture content of air masses is dominated by marine sources, and afforestation will have
negligible influence on rainfall and macroclimates. The distribution of forests is a conse-
quence of climate and soil conditions not the reverse.
In addition to the South African catchment studies of water use from Eucalyptus complemen-
tary studies have been carried out in Australia (e.g. Williamson and Bettenay 1979, Lima 1984)
and India (Mathur et al. 1976). Although these may be sufficient to allow comparisons to be
drawn concerning relative water use of Eucalyptus spp. in the regions where the studies were car-
ried out, extrapolation of the results to other areas is difficult because the mechanisms responsi-
ble for enhanced losses can seldom be determined from catchment studies alone.
However, the general pattern shown by these studies is similar to that found in the majority
of catchment studies which have compared runoff from forested and unforested catchments
worldwide, namely, that the runoff is usually less from the forested catchment (Hibbert 1967,
Bosch and Hewlett 1982).
Water use summary

A new understanding has been gained in recent years of the evaporation from forests in both the
dry and wet regions of the world based on process studies. These studies, which have used a wide

variety of techniques, indicate decreased runoff from areas under forests as compared with areas
under shorter crops. They also indicate that in wet conditions interception losses will be higher
from forests than shorter crops, primarily because of increased atmospheric transport of water
vapour from their aerodynamically rough surfaces. In dry (drought) conditions transpiration
from forests is likely to be greater because of the generally increased rooting depth of trees as
compared with shorter crops and their consequent greater access to soil water.
The new understanding indicates that in both very wet and very dry climates evaporation
from forests is likely to be higher than that from shorter crops and that consequently runoff will
be decreased from forested areas. Occasional exceptions to this rule exist but can generally be
explained by unusual circumstances (e.g. Greenwood 1992).
Eucalyptus and seasonal flow

Although it is possible, with only a few exceptions, to draw general conclusions with respect to the
impacts of forests, including those of eucalypts, on annual flow, the same cannot be claimed for the
impacts of forests on the seasonal flow regime. Different, site-specific (often competing) processes
may be operating and the direction, let alone the magnitude of the impact, may be difficult to pre-
dict for a particular site.
Theoretical considerations and observations

From theoretical considerations it would be expected that
1 Increased transpiration and increased dry period transpiration will increase soil moisture
deficits and reduce dry season flows.
2 Increased infiltration under (natural) forest will lead to higher soil water recharge and
increased dry season flows.
3 For cloud forests, increased cloud water deposition may augment dry season flows.
Observations from South Africa indicate that increased dry period transpiration is reducing
dry season flows, in line with expectations. Van Lill et al. (1980), reporting studies at
Mokobulaan in the Transvaal, showed that afforestation of grassland with Eucalyptus grandis
reduced annual flows by 300380 mm, with most of the reduction occurring during the wet
summer season. More recently, Scott and Smith (1997), analysing results from five of the South
African catchment studies, concluded that percentage reductions in low (dry season) flow as a
result of afforestation were actually greater than the reduction in annual flow. Scott and Lesch
(1997) also report that on the Mokobulaan research catchments under E. grandis the streamflow
completely dried up by the ninth year after planting; the eucalypts were clearfelled at age
sixteen years but perennial streamflow did not return for another five years. They attribute this large
lag time to very deep soil moisture deficits generated by the eucalypts which require many years
of rainfall before field capacity conditions can be established and recharge of the groundwater
aquifer and perennial flows can take place.
Other reports from South Africa relate to the impacts on flow of self-seeded trees (invaders)
originating from plantations of exotic species. It has been standard forestry practice in South
Africa to avoid the deliberate planting of trees in the riparian zones of afforested catchments, to
reduce the risk of soil erosion close to the stream channel and to avoid any increase in water use
by riparian vegetation. Invaders are no respecters of forestry practice and often spread rapidly
into these riparian areas. It has been demonstrated that removal of infestations of self established

riparian trees can have huge effects on streamflow. Dye and Poulter (1995) have shown that
removal of a strip of self-sown Pinus patula and Acacia mearnsii along a 500 m riparian zone at
Kalmoesfontein increased streamflow by 120 per cent. Even more dramatic are reports (DWAF
1996) of a stream in Mpumalanga that, before the clearing of a 500 m strip of riparian Eucalyptus
grandis, disappeared within 50 m of entering the stand. About three weeks after clearing the
eucalypts the stream was visible for 200 m in the stand and after one month it was running
through the stand. It was postulated that it had taken about a month for the stream and rainfall
to recharge the water table, restoring a perennial stream from a dry streambed.
The hydrological dangers from invading trees are not just local in their impact. It has been
calculated (Le Maitre et al. 1996) that, unless curtailed, invaders will eventually reduce the water
supply to Cape Town by 30 per cent. It has also been shown that the cost of water from the best
dam option is several-fold more expensive than the cost of water yielded through clearing the
invading aliens (DWAF 1996).
Summary
The observations from South Africa on the impacts of eucalypt plantations on seasonal flows
demonstrate the potential severity of the impacts and the care that must be taken in weighing
up the pros and cons of establishing such plantations.
The complexity of the competing processes affecting dry season flows indicates that detailed,
site-specific models will be required to predict impacts. In general, the role of Eucalyptus and other
tree species in determining the infiltration properties of soils, as they affect the hydrological func-
tioning of catchments through surface runoff generation, recharge and high and low flows and
catchment degradation, remains poorly understood. Modelling approaches which are able to take
into account forest influences and soil physical properties will be required to predict these site-
specific impacts.
Eucalypts and erosion

The role of eucalypt plantations and other forest plantations in relation to soil erosion remains
controversial. If foresters are under suspicion for propagating the myth that forests are the cause
of high rainfall in upland areas then there may be equal suspicions raised regarding the oft cited
universal claims of the benefits of forests in relation to reduced erosion. As with impacts on sea-
sonal flows, the impacts on erosion are likely to be site specific, and again, many, and often com-
peting processes, are likely to be operating.
Conventional theory and observations indicate these benefits of afforestation:
1 Reduced incidence of surface runoff and reduced erosion transport due to high infiltration
rates in natural, mixed forests.
2 Enhanced slope stability, which tends to reduce erosion, due to reduced soil water pressure
and the binding effect of tree roots.
As Figure 2.1 illustrates, however, there may also be adverse effects:
1 Pre-planting, maintenance and harvesting activities may contribute to such things as soil
compaction, increased surface flow and gully formation.
2 Reduced slope stability, which tends to increase erosion, due to windthrow of trees and the
weight of the tree crop.
3 Splash-induced erosion from drops falling from the leaves of forest canopies.

Figure 2.1 Erosion under eucalypts planted on steep slopes in Tamil Nadu, India (photo: I. Calder).
The benefits gained by afforesting degraded and eroded catchments will be very dependent on
the situation and the management methods employed and afforestation should not necessarily be
seen as a quick panacea. The choice of tree species will also be important in any programme
designed to reduce erosion and catchment degradation, especially as it is now known that
splash-induced erosion is related to tree species.
Forests can also influence soil erosion by altering the drop size distribution of the incident rain-
fall. Contrary to popular belief, forest canopies do not necessarily protect the soil from raindrop
impacts. In recent years there has been new understanding of the importance and significance of
this effect, particularly as it relates to the choice of tree species to minimise erosion. In some cases
there is actually the potential for increased erosion from drops falling from forest canopies.
Although the importance of species in determining drop size and erosive impacts has not always
been well understood, results of recent studies involving the measurement of dropsize spectra
have advanced our knowledge in this area. In particular they have shown that
1 Below-canopy drop size is independent of the raindrop size falling on the top of the canopy.
2 The below-canopy drop size spectrum is a characteristic of the species and varies widely
between species. This can result in large differences in the potential for erosion; kinetic ener-
gies of drops falling from Tectona grandis can be as much as nine times greater than those from
Pinus caribaea and about four times greater than Eucalyptus camaldulensis.
The canopy of the tree is not the only canopy affecting drop size modification and erosion.
The presence of an understorey canopy, close to the ground where drops cannot reach terminal
velocities, is very effective in ameliorating splash-induced erosion. Where the understorey has
been removed through fire or biological competition the potential for erosion is very much
increased (Figure 2.1).
Conclusions
As a result of comprehensive research programmes hard evidence now exists on the hydrological
impacts of eucalyptus plantations. The information has been hard won through detailed studies in

India, South Africa, South America and Australia. The results do not show Eucalyptus species to be
quite as harmful as they have often been portrayed by environmentalists but neither do they show
them to be without hydrological disbenefits. What they do show is a complex pattern of interac-
tions, some of which may be seen as beneficial and others as adverse. Although the researchers
have done their work, and major advances in knowledge have been achieved, the use of this
knowledge for land management purposes, and in the better and more productive management of
eucalypt plantations, has been less spectacular. This is perhaps unsurprising as the issues are com-
plex and the tools for holistic resource management such as Decision Support Systems which
can assist with assessing the economic, hydrological and ecological tradeoffs associated with land-
use decision making (OConnell 1995, OCallaghan 1996) have only recently been developed
and the inclusion of socio-economic evaluation methods has yet to be achieved.
Eucalyptus species are beneficial in having high economic value, both for timber and pulp and for
oil production. Also beneficial are their high plot water use efficiencies; they probably produce
more biomass per unit of water evaporated on a plot basis than any other tree species.
Furthermore, their high growth rates make them very attractive plantation species, and in some
countries such as Australia their ability to reduce and hold down water tables is a very great
advantage in salinity control. Offsetting these advantages is the high water consumption that
needs to be considered, in an integrated way, with other economic, socio-economic and environ-
mental factors. The challenge for future forest managers, whether the forest is geared towards
production of oil, timber or pulp, is to design sustainable forestry systems for eucalypts which
minimise some of the adverse hydrological impacts that have been identified, whilst maximising
economic benefits and being compatible with the social and economic needs of the local people.
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3 Eucalypts in cultivation: an overview
John W. Turnbull and Trevor H. Booth
Introduction
Australias natural forests and woodlands are dominated by eucalypts. They extend over 28 million
hectares from temperate latitudes (42S) in Tasmania to the tropics (11S) in Queensland. Beyond
Australia small areas of natural eucalypt forests occur in tropical Indonesia, Papua New Guinea and
the Philippines. Within this vast geographic range there is great ecological variability. Eucalypts
fringe the sea coast in many places yet extend to an altitude of 2960 m in the mountains of Timor.
In Tasmania the varnished gum, Eucalyptus vernicosa, is a sprawling shrub while not far away in the
Florentine Valley the giant mountain ash (E. regnans) is one of several species that can exceed
70 m in height. The genetic diversity of the genus Eucalyptus is very great with over 700 species
having been described and many of the species have great intra-specific variation. In 1988 the
official Flora of Australia recognised 513 species (Chippendale 1988) but intensive taxonomic
studies since then have resulted in descriptions of almost 200 new species (e.g. Brooker and
Hopper 1991, Hill and Johnson 1992, Pryor et al. 1995).
When Australia was first settled in the late eighteenth century, eucalypts were used for farm
buildings, fencing and fuelwood. The medicinal value of the essential oils extracted from the
leaves of some species was also recognised. Elsewhere, eucalypts were regarded as botanical
curiosities and were soon cultivated in botanical gardens and private arboreta in Europe. Once in
cultivation, the potential of some species to grow rapidly and produce a variety of timber and
non-timber forest products was recognised. Their seeds were sought after throughout the world
wherever the winter climate was not too severe and they quickly deserved the title the emigrant
eucalypts coined by Zacharin (1978). Some were planted for their ornamental value, others for
land reclamation. Farmers planted them for windbreaks and to produce posts and poles. In coun-
tries such as Brazil and South Africa, eucalypts were planted along railway lines to provide fuel
for wood-burning locomotives. The reasons for planting eucalypts have changed significantly
over time, and the end uses to which the species have been put are diverse. Today, eucalypts pro-
vide sawn-timber, plywood, fibreboard, mine props, pulp for paper and rayon, poles, firewood,
charcoal, essential oils, honey, and shade and shelter (Hillis and Brown 1978). Less conventional
uses include the production of plant growth regulators, tannin extracts, industrial chemical
additives, adhesives and fodder additives (Song 1992).
The genus has many favourable characteristics including high growth rates, wide adaptability
to soils and climate, ease of management through coppicing, valuable wood properties
and absence of weediness. From the hundreds of species in the natural forests many have been
introduced and tested for their adaptability and utility but only a relatively few have become
widely cultivated. In China, for example, over 200 species have been introduced but fewer than
ten are now cultivated on a significant scale. This is also the situation elsewhere and just four

species, E. camaldulensis, E. globulus, E. grandis and E. tereticornis, dominate plantations globally.
Eucalypts used in the commercial production of essential oils (mainly those rich in cineole,
citronellal, phellandrene or piperitone) include E. globulus, E. polybractea, E. radiata, E. smithii,
E. elata, E. citriodora, E. dives and E. kochii (Small 1981, Boland et al. 1991, Coppen and
Hone 1992).
This chapter describes the extent of eucalypt planting, the use of eucalypts to improve farm
income and services, species/site selection and models which have been developed to try and
optimise this (particularly for oil-bearing eucalypts), and some aspects of their growth charac-
teristics and management technologies. The cultivation of commercially important oil-yielding
species in particular parts of the world is described in detail in other chapters.
Large-scale planting of eucalypts
Size and location of main plantings

Reliable global estimates for areas of planted eucalypts are difficult to obtain. Statistical information
is incomplete and there is confusion between new areas of planting and coppice regeneration of
existing plantations. In places such as China and India many eucalypts are planted by farmers in
very small woodlots, or in lines around fields and along waterways and railways, so accurate area
estimates are extremely difficult to make. Even in Brazil, where eucalypts are planted in large
blocks for industrial wood production, the estimates range from 3.2 million ha (EMBRAPA 1996)
to over 5 million ha (Barros and Novais 1996). Nevertheless, a global estimate of 13.4 million ha of
plantations (Davidson 1995 and Appendix 2) gives a good indication of the extent and popularity
of eucalypts in cultivation.
In the tropics there were over 10 million ha of eucalypt plantations at the end of 1990 (FAO
1993), principally in tropical America (4 million ha) and in Asia (5 million ha). The American
statistic is dominated by Brazil, where there are 3.2 million ha (EMBRAPA 1996), and in
tropical Asia India has over 4 million ha including trees in various configurations on
farms (Davidson 1995). In addition, there are substantial plantations in countries with more
temperate climates including Australia 287,000 ha (Wood et al. 1999), Chile 300,000 ha
(Flynn and Shield 1999), China 600,000 ha (Wang et al. 1994), Morocco 200,000 ha (Marien
1991), Portugal 500,000 ha (Pereira et al. 1996), South Africa 600,000 ha (Flynn and Shield
1999) and Spain 400,000 ha (Soares 1994). Disaggregated country statistics, including
plantation ownership and utilisation for wood products, have been assembled by Flynn and
Shield (1999).
Increased eucalypt plantation areas are projected in several countries. Plantings will continue
in Brazil but not at the very high rates of the recent past as there will be more effort to increase
the productivity and quality of existing areas. Both China and India have active reforestation
programmes and, although there has been variable success and acceptance of eucalypts in parts of
India, the great demand for wood will undoubtedly ensure that planting continues.
Eucalypt planting has accelerated in recent years in several tropical countries. Large areas of
E. camaldulensis have been established in Thailand and Vietnam. There are also 43,000 ha of high
yielding clonal plantations in the Congo (Bouillet et al. 1999) and in Vietnam. However, exten-
sive planting of eucalypts in the lowland humid tropics has been inhibited by the incidence of
pathogens and insect pests which reduce productivity. Only a few eucalypt species, such as
E. urophylla, E. deglupta and E. pellita, appear to be adapted to hot, humid conditions (Werren
1991). There are also active plantation programmes in the more temperate areas. Australian
plantations increased from 125,000 to 287,000 ha between 1994 and 1998 (Cromer et al. 1995,

Wood et al. 1999), mainly using E. globulus and E. nitens. In Chile the plantation area of euca-
lypts, mainly E. globulus and, more recently, E. nitens, increased from 185,000 ha in 1990 to over
300,000 ha in 1998 (Anon. 1990, Flynn and Shield 1999), and in Uruguay about 300,000 ha
have been planted since 1988. These trends suggest that eucalypt plantation establishment
through the 1990s will have resulted in a total area of over 15 million ha in 2000.
It is inevitable that natural forests will continue to be cleared for agriculture and other pur-
poses and that planted eucalypts will have a major role, often expanding, in providing wood
products, improved standards of living, and environmental protection in many countries.
Industrial plantations
The industrial use of eucalypts is expanding rapidly as large areas of plantations are being
established to provide medium- to low-density short-fibre pulp for paper. The plantation-grown
wood is usually harvested after 510 years and provides a uniform material with high bright-
ness, and good opacity and bulk, all of which make the pulp very suitable for the production of
copying, printing, writing and tissue papers. Demand for these products is rising, and with it
the demand for eucalypt pulp, such that most of the internationally traded bleached hardwood
pulp is now coming from eucalypts.
Huge areas of eucalypt plantations for industrial wood have been established by private com-
panies in countries such as Brazil, Chile, Uruguay, Portugal and South Africa (Attiwill and
Adams 1996, Campinhos 1999, Turnbull 1999). These plantations are in large compact blocks
close to the production plant to minimise transportation costs. They usually comprise a single
species and use genetically selected stock, often clones, which is managed very intensively with
clean weeding, fertilising and pest control. These management practices are all designed to max-
imise production of very uniform wood. Leaves are harvested from some industrial pulpwood
plantations of E. globulus to produce cineole-rich oil as a by-product.
Most research into plantation management has been undertaken to enhance the productivity
and economic viability of these large-scale plantations. Some of the technologies developed can
be readily transferred to small-scale planting or can be adapted, but as farm planting often offers
the opportunity of producing more diverse products using more flexible management regimes,
it is likely that additional research will be required to develop a full range of technologies appro-
priate for eucalypt planting by smallholders.
Growing eucalypts on farms
Why plant eucalypts?

It is not the purpose of this section to describe the role of trees on farms. Others such as Hall
et al. (1972), Cremer (1990) and Arnold and Dewees (1995) have done this already. The aim is to
stress that farmers already plant eucalypts and others will do so when markets and other condi-
tions are favourable.
Farmers are increasingly diversifying their farming systems by tree planting to minimise risk
and provide a range of products and services. Deep-rooted species such as Grevillea robusta are
very compatible with agricultural crops but eucalypts are not always the most desirable trees to
plant on farms as many species have shallow root systems which compete effectively with agri-
cultural crops. Nevertheless, there are situations where eucalypts are grown mixed with crops
and the severity of the competition is reduced by applying different management strategies.
Although many eucalypts have sparse crowns and permit high levels of radiation to reach the

ground, the canopy can be manipulated by pruning or coppicing. Removal of the crown biomass
has the effect of reducing the root mass and this diminishes root competition and releases nutri-
ents into the soil as the roots decompose. In the drier parts of Malawi, where some farmers grow
E. camaldulensis amongst their crops, the branches are pruned off until only the stem remains
when the trees begin to compete with the maize or other crops.
Population growth in the developing world has led to a greater demand for fuelwood, poles
and other wood products. In many countries where fuelwood is the main source of energy for the
rural population there is a substantial shortfall in supply. Natural forests have felt the pressure
and are being heavily exploited, but the scale of wood shortages in many countries is such that
these forests alone cannot meet the needs. By the year 2010, consumption of fuelwood and poles
will have increased substantially in rural areas, especially in India, Kenya, Nigeria and other
densely populated countries of Asia and Africa where much of the natural forest has disappeared
or is severely degraded (FAO 1991). Increasingly, farmers and other land holders are becoming
involved in providing both wood for profit and subsistence from new on-farm plantings.
Farmers plant trees for a variety of reasons including shade and shelter; wood products;
non-wood products such as fruit, fodder, honey, essential oils; and savings and security. They are
often more interested in trees yielding products that can be sold to provide a cash income. The
main reason for some farmers choosing to plant E. globulus in Yunnan province, China, is the
quick cash return they get from harvesting leaves for cineole oil production, and in India and
elsewhere branches and litter for fuel may be valued secondary products, especially by women
(e.g. Nesmith 1991). Tree planting for shade, shelter and the marking of farm boundaries is also
important for some farmers. The use of trees as a living bank account, to be harvested when there
is a need for cash, is widespread.
Choosing the species which best provides profitable and readily marketed products, or meets
the immediate needs of the farmer, is a critical first step in the decision-making process. Fast
growing species which are disease-free and easily managed are usually preferred because they
give an early return on the capital invested and do not divert the farmer from other activities.
Some eucalypts meet these criteria and are popular with farmers in many parts of the world.
On-farm planting worldwide

Eucalypts, established to a very large extent by farmers, dominate the rural landscapes in
Ethiopia, China, India, Peru, Rwanda and elsewhere. In Ethiopia, farmers plant E. globulus on
small areas of land and subsequently the plots may be managed to yield a variety of products
including leaves and small branches for fuelwood, poles or posts for house building and other
farm uses, and large poles and timber for sale. Farmers who have insufficient land to have wood-
lots nevertheless often grow a few trees which they can sell to buy food when their crops are
exhausted. Many people in Ethiopia are absolutely dependent on eucalypts as a source of fuel and
house building material. Unlike farmers in China, India and Peru they have not exploited the
potential of E. globulus to yield cineole-rich oil.
Peoples Republic of China

In southern China, eucalypts are a prominent and important part of the rural landscape. They are
favoured because they grow relatively fast and tolerate poor, degraded soils. There are many
dispersed plantings on farms and it is estimated that some one billion trees are planted beside
farmhouses and along roads and waterways (Wang et al. 1994). The most widely used species
have been E. exserta, E. citriodora, E. globulus and a hybrid of unknown origin referred to as

E. leizhou No. 1, but these are being replaced by more productive species such as E. grandis,
E. urophylla and hybrids between these two species. The wood is used for posts and poles, pulpwood,
furniture, farm tools and fuel. Essential oils and tannins are extracted from the leaves and the flowers
support honey production. Oil extraction began in 1958 and since 1970 has developed rapidly;
China now dominates the international eucalyptus oil market (Song 1992, Coppen and Hone 1992).
The eucalypts play an important part in crop production by providing shelter from typhoons in
coastal areas and make a significant contribution to the quality of life and income of farmers.
India
Farmers in India have been growing eucalypts on an increasing scale over the past fifteen years.
As the Indian population approaches one billion, so there is an immense requirement for wood
for both industrial and domestic use. The annual demand for industrial wood is three times the
estimated production (Kumar 1991). Economic benefits have generally come from eucalypt
plantations, although excessive planting by farmers in Haryana and the Punjab has now resulted
in a local glut of fuelwood and small-sized poles, leading to falling prices. Farmers who planted
early made large profits while those planting later did not earn similar rewards and some would
have been better growing agricultural crops (Dewees and Saxena 1995, Saxena and Vishwa
Ballabh 1995).
E. tereticornis, known locally as Eucalyptus hybrid or Mysore gum, is the preferred species
for planting in India. It is used extensively for village woodlots, on farms and along the bound-
aries of roads, canals and railways. It has also been widely planted on what are broadly termed
wastelands or degraded lands. Its popularity is based on its capacity for rapid growth, resistance
to cattle browsing, great adaptability to varying environmental conditions, ready market at
profitable prices and suitability of the wood for fuel, rural housing, etc. (Rajan 1987, Shah
1988). Farmers have established block plantings and windbreaks on the margins of the fields
and sometimes grow eucalypts in combination with agricultural crops. The potential of essential
oil yielding eucalypts, such as E. citriodora, grown in combination with crops has been high-
lighted by Shiva et al. (1988), and in nearby Nepal selected clones of E. camaldulensis, which have
high levels of cineole in the leaves, have been suggested for planting on small farms (White
1988). Eucalypts are often planted in India to meet future contingencies and have functioned as
savings banks of the rural poor.
In India, as in some other countries, there is continuing controversy over the use of eucalypts.
There are questions about the diversion of cropland from food production to forestry, reduction
in employment and the utilisation of common lands for eucalypt growing by the more powerful
members of the community (Saxena and Vishwa Ballabh 1995). While from the farmers or
entrepreneurs viewpoint, eucalypt growing makes economic sense, the landless poor may
endure increased hardship and reduced welfare when farmers grow eucalypts (Gregersen et al.
1989). Although the debate is frequently framed in terms of the beneficial and negative ecolog-
ical impacts of eucalypts, the major problem in fact relates to land availability, tenure and man-
agement (Poore and Fries 1985). Hydrological studies show a complex series of interactions,
some of which may be seen as beneficial and others as adverse (Calder 1994). According to an
analysis by Raintree and Lantican (1993),
the real crux of the political controversy surrounding eucalyptus planting in India was the
opportunity cost of a social forestry programme which generated such dramatic benefits for
the relatively better off segments of society while leaving the originally targeted beneficiaries
of the Social Forestry programme without benefit.

Clearly, if eucalypts are to realise their full potential to provide benefits to a community there
will need to be much more careful analysis of ecological, economic and social factors before
extensive planting is undertaken.
Australia
In some countries, farmers are urged by their governments to plant trees as part of their farming
systems for environmental protection reasons. In the southwest of Western Australia deforesta-
tion has resulted in rising watertables which bring saline ground water to the surface. Deep-
rooted perennials, especially trees and shrubs, can use excess water and become part of the
salinity management strategy (e.g. Marcar et al. 1995). In Western Australia it is estimated that
3 million ha of trees and shrubs are necessary to manage the states salinity problem successfully.
Commercial wood plantations of eucalypts and pines, shrubby forage crops and new tree crops
such as oil-producing mallee eucalypts are being promoted to achieve this target (Agriculture
Western Australia 1996). Combinations of fodder trees and eucalypts may be planted in an agro-
forestry system to provide animal forage, essential oils and salinity control (Eastham et al. 1993).
The government of Western Australia is supporting financially the establishment of a eucalyp-
tus oil industry based on mallee species such as E. kochii (subspp. kochii and plenissima), E. horistes,
E. polybractea and E. angustissima. Although most eucalypts are currently grown for a relatively
limited medicinal oil market, the Western Australians are aiming to sell their oils for use as a
range of industrial solvents (Bartle 1994, Bartle et al. 1996).
The future
There is increasing evidence that in future more industrial wood will be produced in small-scale
plantations by farmers (Cossalter 1996). Plantations have already been established by farmers
primarily to supply wood to industrial enterprises. In Spain, there is an example of a marriage
between industrial and social forestry with farmers cooperating with a private pulp and paper
company, Celulosas de Asturias S.A., to grow eucalypts on their land to sell to the mill, while
also making money from the production of honey and essential oils (CEASA 1994). Similar
schemes operate in Brazil (e.g. de Freitas 1995), the Philippines (Morrison and Bass 1992), India
(Chinniah Sekar et al. 1996) and elsewhere.
There are some basic requirements which must be fulfilled if farmers are to grow trees prof-
itably. There must be a good species/management technology available, a potential market,
roads or other infrastructure to enable cheap transport of the product, clear tenure rights on the
land and trees, and a source of credit for those who need it. If these conditions are met, farmers
need little persuasion to plant trees. While some prefer to plant native trees, the majority will
grow the species which are most profitable or provide the services they require, irrespective of
the origin of the tree. The extensive planting of eucalypts in India for poles and fuelwood when
the prices were favourable is evidence of this, although many were subsequently disappointed
when prices fell (Saxena and Vishwa Ballabh 1995). If secure and profitable markets can be
developed for eucalyptus oils then entrepreneurial farmers will quickly take advantage of the
commercial opportunity.
Species selection and growth prediction

When considering high oil-yielding eucalypts for planting it is useful to know which areas are
suitable for particular species and how well they are likely to grow on specific sites. This section

outlines some of the methods available for answering these questions for important oil-producing
eucalypts such as E. citriodora, E. globulus and E. camaldulensis (Petford provenance).
Climatic requirements
Climate is an important influence on tree growth but climatic data are frequently not available
for forest sites, which are often remote from meteorological stations. Fortunately, mean climatic
conditions can now be estimated reliably for most locations around the world. Mathematical
relationships have been developed which can estimate mean monthly climatic conditions for fac-
tors such as maximum temperature, minimum temperature, precipitation, solar radiation and
evaporation (e.g. Hutchinson et al. 1984). These interpolation relationships allow the range of
climatic conditions experienced by particular trees to be analysed. For example, a program called
BIOCLIM developed by Nix, Busby and Hutchinson takes in geocoded information on species
natural distributions (i.e. sets of observations of latitude, longitude and elevation) and produces
information on species climatic requirements (see Busby 1991 for summary).
Data from natural vs exotic locations

One of the first published applications of BIOCLIM was to analyse the natural distribution of
E. citriodora (Booth 1985), an important oil-yielding eucalypt. The program estimated twelve
climatic factors for each of eighty-four natural locations of E. citriodora. The ranges of these
factors provided an estimate of the species climatic environment in Australia. For example,
mean annual temperature was in the range 1824C, the mean maximum temperature of the
hottest month was in the range 2836C and the mean annual rainfall was in the range
2501100 mm. Some of these estimates must be treated with caution. The lower end of the
rainfall range, for example, was surprisingly low. Trees may be just surviving in such an envi-
ronment or may be growing where additional moisture is available, such as by a river. Despite
problems of interpretation like this the information can be used to suggest areas outside
Australia which might be suitable for growing the species.
Studying natural distributions can provide a first impression of a species climatic require-
ments, but many species can thrive under conditions which are somewhat different from those
within their natural range. Additional information from trials also helps to interpret extreme
values, such as the low rainfall observation mentioned above. An analysis of E. citriodora planta-
tion sites in Africa illustrated some of these differences (Booth et al. 1988). The precise locations
of thirty-two trials of E. citriodora, including seventeen successful trials, in ten countries were
obtained and climatic conditions estimated. Five of the mean annual temperatures recorded at
the successful plantations were slightly below the range recorded from the natural distribution,
whilst the mean annual rainfall was in the range 3801580 mm, with a mean of 882 mm.
Information from many successful trials around the world has been used to develop the
descriptions of the climatic requirements of E. citriodora, E. globulus (particularly E. globulus
subsp. globulus) and E. camaldulensis (northern provenances) and this is illustrated in Table 3.1.
Climatic mapping programs

Whilst descriptions such as those given in Table 3.1 are useful for suggesting areas where the
species might be grown, it is difficult to visualise where such areas occur within a particular coun-
try. The climatic interpolation relationships mentioned above have also helped to develop a fam-
ily of PC-based programs known as climatic mapping programs (see Booth 1996a for several

Table 3.1 Climatic requirements of some oil-producing eucalypts (after Booth and Pryor 1991)
E. globulus E. citriodora E. camaldulensis

subsp. globulus (Petford provenance)
Mean annual rainfall (mm) 5501500 6502500 2502500
Rainfall regimea s, u/b, w s, u/b, w s
Dry seasonb (months) 07 07 28
Mean max temperature, 1930 2839 2840
hottest month (C)
Mean min temperature, 212 822 622
coldest month (C)
Mean annual temperature (C) 918 1728 1828
Absolute minimum !8 !3 nac
temperature (C)
a s "summer, u/b "uniform/bimodal, w " winter.

b Dry season length is number of consecutive months for which rainfall is #40 mm.
c Not applicable (frost should not be a problem in areas indicated by other factors).
Figure 3.1 Regions of China (dark-shaded areas) which are climatically suitable for Eucalyptus globulus
subsp. globulus.
examples). These programs can take in descriptions of climatic ranges similar to those given in
Table 3.1 and generate maps showing climatically suitable and unsuitable areas. The programs
include a moveable marker which can be positioned over any location. This allows the detailed
climatic data for that particular location to be examined and compared with the current descrip-
tion of a species requirements. Figure 3.1 shows example output from a program for China indi-
cating areas likely to be climatically suitable for E. globulus subsp. globulus. The output is based
on interpolated climatic data estimated for nearly 100,000 locations across China. Many other
climatic mapping programs have been developed at CSIRO Forestry and Forest Products in coll-
aboration with researchers in other countries. These include programs for individual countries
such as Australia, Thailand, Philippines, Indonesia, Laos, Vietnam and Zimbabwe, as well as
major regions such as Africa and Latin America and, at a coarser scale, for the whole world
(Booth 1996a,b).

Growth prediction
Relationship between site and environmental factors

Being able to identify where particular trees will grow is useful, but many people need, in addition,
an approximate indication of how well particular trees will grow at specific sites. In ideal situations
trees of the same species will already be widely grown within the area of interest. In this case it may
be possible to collect data on growth as well as environmental conditions and to develop predictive
relationships to assess potential planting sites. For example, Inions (1991) has described the devel-
opment of site index curves for E. globulus plantations in Western Australia, where site index is
related to top height at five years of age. Height is used as an indication of performance as it is rel-
atively little affected by differences in stand density and top height is the average of the tallest forty
trees per hectare. Curves of top height development by age can be plotted so that site index can be
estimated for stands of any age, and this enables the performance of stands of different ages to be
directly compared.
Using data from fifty-one sites, Inions (1991) developed the following equation relating site
index to environmental factors:
S "B0(S1 S2)B1
where
S1"B0 ! B1(SILT50 BD50 RAIN_DQ) $B2(SILT50 BD50 RAIN_DQ TEMP_HM)
!B3 RAIN $ B4 RAIN_LM !B5{(SILT50 BD50) $ (CLAY50 BD50)}
S2"exp{B0 ! B1(NIT10)!1 $ B2(NIT10)!2 !B3(P10)!1 $B4 SILT10}
and
S is site index (m)
B0, B1, B2, B3 and B4 are coefficients (given in Inions 1992)
SILT50 is silt content at 50 cm soil depth (%, wt)
BD50 is bulk density at 50 cm soil depth (g cm!3)
RAIN_DQ is rainfall in the driest quarter (mm)
TEMP_HM is highest monthly temperature (C)
RAIN is total annual rainfall (mm)
RAIN_LM is rainfall in the driest month (mm)
CLAY50 is clay content at 50 cm soil depth (%, wt)
NIT10 is nitrate content at 10 cm soil depth (%g g!1)
P10 is phosphorus content at 10 cm soil depth (%g g!1)
SILT10 is silt content at 10 cm soil depth (%, wt)
The values of the coefficients have been omitted here to simplify the equation. Their actual
values are irrelevant to most readers as they are only useful for predicting growth within the area
where they were collected, that is, the southwest of Western Australia. Although the relationship
is complex it can be seen that temperature, rainfall, soil water-holding capacity and soil nutrition
are important factors determining tree growth. Other authors have developed predictive relation-
ships relating the growth of oil-yielding eucalypts to environmental conditions. For example,
Janmahasatien et al. (1996) describe relationships for E. camaldulensis in Thailand. However,
Inions (1991, 1992) also gathered independent data from a further eighteen sites to test the equa-
tion given above. These sites had observed site indices ranging from about 10 to 22 m. The resi-
dual statistics generated by the equation were 0.38 with a standard deviation of 1.71 (r2 "0.73).

Regression relationships, such as those prepared by Inions (1991, 1992), relate tree growth
directly to environmental factors such as rainfall and soil nutrients. In recent years considerable
effort has gone into developing process-based models which attempt to simulate important
processes related to growth such as light interception, photosynthesis and respiration. Relatively
simple models such as ProMod (Battaglia and Sands 1997, Sands et al. 2000) and 3-PG
(Landsberg and Waring 1997, Landsberg et al. 2001) have been developed to predict the suita-
bility of particular sites for particular species. For example, the ProMod model was initially
developed using data from nine E. globulus plots in Tasmania and Western Australia and was vali-
dated using data from nineteen E. globulus plots in northern Tasmania. Regression of predicted
against observed mean annual increment (MAI) for the nineteen validation plots produced an
r2 of 0.81, compared with an r2 of 0.91 for the research plots.
Leaf biomass and oil production

Most growth prediction work has used measures such as height and volume, which are directly
or indirectly related to wood production. Factors such as site index and MAI should also be
related to leaf production, at least in the early stages of growth before canopy closure, and hence
should be expected to bear some relation to oil yield. However, predicting actual oil yield, which
is a function of both leaf biomass and leaf oil concentration, is more difficult. Doran (1991) con-
cluded that the effects of environmental factors on the oil concentration in leaves are likely to
involve a highly complex network of variables, and very little is known about them. In addition
to environmental factors he noted that important influences on oil concentration include genetics,
type and age of leaf, and extraction techniques. Doran (1992) further concluded that the extent
and direction of variation in oil concentration of E. camaldulensis depended very much on the
individual tree. Though it may currently be impossible to predict oil yield for potential sites it
should at least be possible in some areas to use relationships similar to those described by Inions
(1991, 1992), Janmahasatien et al. (1996) and Battaglia and Sands (1997) to identify sites where
oil-yielding species such as E. globulus and E. camaldulensis can grow well. However, relationships
such as these can only be developed in areas where the species are already widely grown in plan-
tations or trials. There is need for an evaluation system which can use minimal data to provide
tentative predictions in those areas (the vast majority) where high oil-yielding species are not
already widely grown.
Other predictive models

The Plantgro model (Hackett 1991) was developed by CSIRO to provide coarse predictions of the
growth of lesser-known crops. The model is run using individual plant, climate and soil files, and
the program makes it easy for users to develop their own files to meet their particular require-
ments. The program produces summary predictions of likely growth patterns as well as detailed
evaluations of limitations due to light, temperature, moisture and twelve important soil factors.
Plantgro uses simple notional relationships, which are two-dimensional relationships indicating
which conditions are most suitable for growth and those which are less suitable. Liebigs (1855)
Law of the Minimum is used to combine limitations. In simple terms this states that the most
limiting factor determines plant performance, that is, favourable factors do not compensate for
unfavourable factors. Overall conditions are evaluated on a scale of 09 where 0 indicates ideal
conditions (i.e. no limitations) and nine indicates the greatest possible limitations.
Fryer (1996) described a test of Plantgro which related predictions of site potential for
E. camaldulensis in Central America to actual growth measurements (r2 "0.63 for nine locations

spread across six countries). He also included the Plantgro plant file which he used to describe
the environmental requirements of E. camaldulensis. In the same book Davidson (1996) describes
a general method for developing Plantgro plant files for forest trees. Information from tree trial
databases such as the TROPIS database being developed by the Centre for International Forestry
Research (CIFOR) (Vanclay 1996), and from tree growth databases such as TREDAT main-
tained by CSIRO (Brown et al. 1989), can assist in the development of files describing the
requirements of particular trees. Pawitan (1996) describes how Plantgro was integrated with a
geographical information system to provide a broadscale evaluation of site potential for many
tree species, including E. camaldulensis, across 40 per cent of Indonesia. As part of this work,
Plantgros limitation ratings were related to growth curves to produce estimates of wood
production for use in economic analyses.
In conclusion, it can be said that climatic mapping programs can assist in identifying regions
likely to be suitable for growing oil-yielding eucalypts, whilst statistical methods or simple
models can be used to help to suggest how well particular trees are likely to grow at specific
sites. More work is needed to develop methods for predicting likely oil yields of particular
species and provenances at potential sites, as well as to determine the often substantial variations
in growth, survival and adaptability between provenances of particular species.
Whilst existing yield prediction methods are useful, unexpected problems such as pests and
diseases may arise in particular areas. For example, work at CSIRO Forestry and Forest Products
has developed methods to predict risks of diseases such as Cylindrocladium quinqueseptatum, a leaf
blight which affects some provenances of E. camaldulensis in parts of the world such as Vietnam
(Booth et al. 2000). However, trials should always be established in a particular region before
large-scale plantations are established and the socio-economic impacts of plantation establish-
ment on the local population should also be carefully assessed.
Nutritional factors and the growth of eucalypts

When managers have chosen the species they want to provide the desired products, their man-
agement options to improve growth are largely restricted to those which improve the availabil-
ity of water, nutrients and other resources such as light. Sub-optimal levels of any of these factors
will reduce growth and productivity. Many eucalypts have been cultivated because they grow
rapidly and this characteristic is related to the unusual bud system of the leafy shoot in this
genus ( Jacobs 1955, FAO 1981, Florence 1996). In the axil of each leaf is a naked bud which
enables continuous growth above a critical temperature, providing water and nutrients are not
limiting. This feature is associated with very high rates of growth and productivity in eucalypt
plantations (Beadle and Inions 1990). Ultimately, it is the amount of radiation at the plantation
site which sets limits to growth but weather and soil constraints will reduce potential growth.
Low temperatures and low rainfall limit the planting of eucalypts in many areas but constrain-
ing nutritional factors can often be readily manipulated in eucalypt cultivation.
Eucalypts grow naturally in a diversity of ecosystems and the quality of sites varies enor-
mously throughout their distribution. The evolution of species on high nutrient, high water
availability has produced different morphological and physiological attributes among eucalypts.
Species that have adapted to nutrient-deficient and drought-prone sites often show limited abil-
ity to respond to additional nutrients in the form of fertiliser and this can reduce their sustain-
ability for high-yielding, short-rotation, plantations (Kriedemann and Cromer 1996). Species
trials have demonstrated species with high potential for rapid growth and, when there are mini-
mal constraints, species such as E. grandis, E. globulus and E. urophylla are among the fastest
growing and the most responsive to added nutrients (e.g. Turvey 1995). Other species with more

conservative strategies and lower potential growth rates may be planted if they yield particularly
desirable products. The oil-producing eucalypts such as E. radiata, E. dives and E. polybractea are
in this category.
Studies of nutrient cycling, and interventions using inorganic fertiliser, received little atten-
tion until the development of fast-growing plantations. Evans (1992) suggests the reasons for
increased interest in tree nutrition, especially in the tropics, are:
1 The high nutrient demands of fast-growing plantations and the high potential for nutrient
depletion when grown on short rotations on infertile soils in the moist tropics.
2 Fertilising is more economic for trees grown on short rotations.
3 Nutrient inputs assist establishment and uniformity of growth where site heterogeneity
is high.
4 Correction of specific micronutrient deficiencies, such as boron, can significantly improve
productivity.
All these reasons apply in eucalypt cultivation and much research is in progress to define fac-
tors that limit eucalypt productivity, particularly nutrient availability and uptake in relation to
other factors (e.g. Cromer et al. 1995). When eucalypts are grown for leaf oil production the
export of nutrients from the site will be high, and at short intervals, so the potential for nutrient
depletion of the soil is particularly great.
Managers need reliable methods of predicting nutrient requirements for short-rotation euca-
lypt plantations over a range of soil types and climates. However, until recently, systematic gath-
ering of soil information and its interpretation has not been given the attention it deserves for
efficient planning of tree planting operations. Soil management, like land preparation and har-
vesting, needs to be site-specific and there are no general solutions which will produce maxi-
mum yields (Erasmus 1991).
Information is accumulating on eucalypt nutrition (e.g. Attiwill and Adams 1996) and some
generalisations can be made. The majority of eucalypts will not grow well on highly calcareous
sites or heavy textured soils with high pH (Pryor 1976). It is also the case that many eucalypts
go through their life cycle in Australia on soils with very low nutrient status, especially phos-
phorus. Under these conditions they have evolved to be very efficient users of nutrients with
effective internal re-distribution mechanisms (Adams 1996). Many fertiliser experiments have
demonstrated that young eucalypts usually respond to a greater or lesser degree to improved soil
nutritional status providing other factors are not limiting.
Nutrient deficiencies in eucalypts have many causes, including a low rate of nutrient cycling,
interactions with other nutrients, inadequate mycorrhizal associations and excessive weed com-
petition. Manifestation of visual symptoms takes the form of poor tree vigour, leaf chlorosis and
other colour changes, and malformed organs. Deficiency symptoms of nitrogen, phosphorus and
potassium, highly mobile nutrients, appear first in old leaves and gradually extend towards the
shoot apex. In contrast, less mobile or immobile nutrients such as calcium, sulphur, boron, iron,
copper and zinc are first expressed in young leaves and progress to mature leaves (Dell et al.
1995). Boron deficiency, which commonly occurs in eucalypts, results in tip death and multiple
leaders; severely deficient trees may become prostrate. An illustrated guide to nutrient defi-
ciency, toxicity and non-nutritional symptoms of E. globulus, E. grandis, E. pellita and E. urophylla
is provided by Dell et al. (1995). Impaired or abnormal growth of eucalypt leaves and shoots can
also be the result of nutrient toxicities or non-nutrient factors such as plant pathogens, herbi-
cides, air pollutants, genetic factors or environmental stresses, so great care must be exercised
when using visual symptoms to identify a nutritional problem. Additional tests may be needed

to confirm the diagnosis. Plant analysis is often the preferred method of diagnosing nutrient
deficiencies and the following approaches have been used (Mead 1984):
1 Comparison of nutrient concentrations in healthy and unhealthy plants.

2 Estimation of plant nutrient status from a knowledge of relationships between concentra-
tions of nutrients in plant tissues and plant growth.
3 Examination of nutrient balances within plants through calculation of nutrient rations.
4 Biochemical techniques.
The application of fertiliser can correct a specific deficiency and aid establishment and/or stim-
ulate growth. Fertilisers are expensive and so there needs to be careful diagnosis of the nutritional
problem before wide-scale application. Several approaches can be tried, including on-site fertiliser
trials, foliar analysis, soil analysis and pot trials under controlled conditions. Techniques for diag-
nosis have progressed to the point that nutrient deficiencies can usually be detected and growth
on unfertilised sites can often be predicted. However, assessment of nutrient status and prediction
of the magnitude of response to fertiliser for advanced management planning requires more
research (Goncalves et al. 1997).
Fertiliser trials in the field are slow and relatively expensive and must take into consideration
soil variability and the representativeness of the trial site. They must also include the nutrient(s)
which are deficient and hence are rarely used as the primary diagnostic tool (Evans 1992). Foliar
analysis is only useful in detecting deficiencies after the trees are planted, whereas soil analysis or
pot trials using soil from the field site can be used to determine the nutritional status of land before
planting. Most research indicates that maximum response to fertilisers occurs if the application is
within the first three months of planting. The extent of the response may be confounded by other
factors such as the degree of weed control and the site preparation technique (Turvey 1995).
There is concern that the establishment of densely planted, even-aged and genetically homo-
geneous clonal eucalypt plantations designed to maximise wood production will bring increased
risk of disease epidemics. However, the greater economic investment and returns in such planta-
tions allows more intensive control of diseases, including selection and breeding for disease resis-
tance (Turnbull 2000).
Vegetative propagation
The selection and cloning of plantation crops such as rubber and oil palm has resulted in very
substantial increases in latex and oil yields (Tan 1987, Hardon et al. 1987). Cloning of species of
Populus, Cryptomeria and a few other trees has been practised for centuries but the application of
vegetative propagation techniques to eucalypts only began to receive serious attention in the
1950s and 1960s. It is mainly since the late 1970s that eucalypts have been mass propagated
vegetatively for use in plantations. The use of clones selected for high yields of essential oils
appears to be the way forward for improving productivity in this industry as substantial
between-tree variability in oil traits has been demonstrated. Some E. camaldulensis trees have
leaves with almost double the oil content compared to average trees in the same population
(Doran and Williams 1994).
Advantages of vegetative propagation

What is the attraction of clonal multiplication if most eucalypts can be raised easily from seeds?
The reason is that cloning is a technology which enables almost all of the genetic gain generated

in selection and breeding to be captured and utilised in commercial plantations (Nikles 1993).
Common techniques of cloning are cuttings, layering, budding and grafting. More recent
approaches involve micropropagation through the application of cell and tissue culture
technologies. Tissue culture offers the potential for very rapidly multiplying selected eucalypt
genotypes (Hartney and Svensson 1992).
Vegetative propagation is widely used to manage eucalypt breeding populations, and cuttings,
grafts and micropropagules have all found application. However, their use is on a relatively small
scale compared to the mass propagation by cuttings which is being applied extensively in clonal
forestry. The term clonal forestry refers to the use of a number of tested, selected and identified
clones (Eldridge et al. 1993). The rise of, and enthusiasm for, clonal forestry with eucalypts has
mirrored the development of short-rotation, fast-growing eucalypt plantations to provide raw
material for the pulp and paper industries. Since the early 1970s, millions of hectares of these
plantations have been established, initially from seeds and, after 1980, with increasing use of
rooted cuttings.
Early research on rooting eucalypt cuttings in Australia and North Africa indicated that it is
increasingly difficult to root cuttings as the parent plant ages (Pryor and Willing 1963, Franclet
1963) although there is considerable variation between species in their ability to root from
cuttings. One of the easiest species to root is the tropical E. deglupta (Davidson 1974) but others,
such as E. globulus, have remained a challenge to the present day (Sasse 1995). Major advances in
developing rooted cuttings from mature trees for commercial plantations were made in the
Congo by researchers from the Centre Technique Forestier Tropical (CTFT) between 1969 and
1973 (Martin and Quillet 1974). Substantial increases in growth and wood production were
achieved, initially with naturally occurring hybrids in plantations, and subsequently with artifi-
cially manipulated crosses (Martin 1991).
A Brazilian private company, Aracruz Forestal, recognised the potential role of clonal forestry
in increasing productivity in its eucalypt pulpwood plantations. The companys research indi-
cated that gains in volume production and wood quality could be achieved using hybrid clones,
for example, E. grandis & E. urophylla, and in 1979 Aracruz decided to gradually replace its plan-
tations derived from seeds with vegetatively propagated clonal plantations (Campinhos 1993).
By 1990, nearly 126 million rooted cuttings of selected hybrid clones had been planted. Since
putting its cuttings programme on an operational scale Aracruz has established 85 per cent of its
area with clonal plantations and the remaining 15 per cent with seedlings (Campinhos and Silva
1990). The clonal option combined with intensive cultural practices has resulted in very sub-
stantial increases in productivity and wood quality and significant savings in harvesting costs
(Campinhos 1993, 1999). The amount of product (bleached wood pulp) grown on each hectare
of forest has almost doubled, from 5.9 to 10.9 t/ha/yr. At the same time, clonal plantations have
provided a saving of about 22 per cent in harvesting and logging costs through tree uniformity,
branch-free stems and high survival rate.
The use of cuttings has become an integral part of operations for many companies in a num-
ber of countries since Aracruz Forestal in Brazil and CTFT/Unit dAfforestation Industrielle du
Congo in West Africa initiated their large-scale clonal eucalypt plantations. In Morocco, vegeta-
tive propagation techniques have played an important role in transferring the results of tree
improvement into a plantation programme which uses 23 million selected clones of E. camald-
ulensis and E. camaldulensis & E. grandis hybrids each year (Marien 1991). In Colombia, an opera-
tional improvement in wood yield of 40 per cent has been achieved with clones of E. grandis
compared to seedlings since a clonal programme was initiated in 1986. At this site, and else-
where, the matching of clones to specific site conditions is an important strategy (Wright 1995).
South Africa, too, has been at the forefront of the application of clonal techniques to industrial

plantations. For example, Mondi Forests have 35 ha of clone banks which are harvested to produce
810 million rooted cuttings annually (Herman et al. 1991) and here there is also careful matching
of clones and sites.
Factors which influence success

A number of factors determine the success of clonal forestry, for example, the genetic quality of
the clones, site-genotype interactions, silvicultural practices and nursery operations (Adendorff
and Schn 1991). It is important that while producing high quality planting stock the costs are
kept to a minimum. The Aracruz experience is that rooted cuttings cost about 40 per cent more
than seedlings but the gains in productivity are so large that this difference is insignificant
(Campinhos 1993).
The most important propagation characteristic of a species or clone is its rooting ability, and
the cuttings of some eucalypts, for example, E. globulus and E. nitens, are very difficult to root.
Failure to achieve a high level of rooting ability can result in many promising genotypes being
excluded from the clonal programme. For example, if the threshold of rooting ability is set at
70 per cent then about 90 per cent of potential genotypes in E. globulus are excluded (Wilson 1992).
E. globulus is such an important species for plantations that a major research effort has been
directed to developing a satisfactory technique to achieve a high rooting (Sasse 1995). Celulose
Beira Industrial (CELBI) in Portugal has developed a propagation system to root stem cuttings
of E. globulus (Wilson 1992). However, the cuttings of E. globulus develop different root systems
to seedlings and clonal growth has been variable. Further development of current propagation
systems is required before widespread use of E. globulus cuttings can be recommended (Sasse and
Sands 1995) although micropropagation of E. globulus and E. nitens is now a viable option
(Ruaud 1996).
It must be emphasised that the mass propagation of cuttings is only worthwhile when there are
selected genotypes to propagate. The techniques used on a commercial scale include the setting
up and management of clone banks of outstanding individuals and mass propagation of cuttings
from the clone banks. The techniques for the establishment, rejuvenation of clones, preparation of
cuttings, rooting and hardening off of rooted cuttings are described by Eldridge et al. (1993).
These techniques are those used in propagating eucalypt cuttings for large industrial plantations
but similar practices can be applied to achieve improvement in smaller scale operations. It is at
this smaller scale that most eucalyptus oil-producing plantations are likely to operate.
Vegetative propagation by small-scale producers

The small-scale forestry sector faces the difficulty of having to obtain selected material to propa-
gate. It is unlikely that small-scale operations can justify their own tree breeding programmes so
they must make arrangements to use material developed by larger companies or government
agencies, or by joining tree improvement cooperatives where the costs of tree breeding and selec-
tion can be shared. Small-scale operations will generally have limited staff resources and low
technology facilities so the propagation system is likely to use cuttings rather than micropropa-
gation by tissue culture. However, small-scale production of tissue cultured plantlets has
produced propagation material of E. grandis & E. urophylla hybrids for plantations in southern
China. In the tropics, only minimal improvements in facilities and work standards may be
needed to convert a conventional seedling nursery into a cuttings nursery. Technical aspects of
the mass multiplication of eucalypts on a small scale are discussed by Kijkar (1991) and White
(1993). Those considering using a clonal strategy are recommended to undertake a simple

marginal benefit/cost analysis of the type described by Walker and Haines (1998) before making
a final decision.
Eucalyptus oil can be produced either as a by-product of a wood industry or as a crop in its
own right. In Australia and South Africa, growers have specialised oil-producing plantations but
in Spain and Portugal waste leaf comes from E. globulus grown for pulpwood. If produced as a
by-product it is less likely that increasing the quantity or quality of the oil will be a major part
of the breeding programme.
Attempts to improve yield and productivity of oil-producing eucalypts such as E. radiata by
selection and cloning have been frustrated by the difficulty in producing clonal material vegeta-
tively, although micropropagation is more promising (Donald 1991). Tissue culturing techniques
have been applied to E. kochii subsp. kochii in Western Australia and the possibilities appear
extremely good for producing cineole-rich oil in the tropics from selected clones of E. camaldulensis
for which the vegetative propagation technology is relatively simple (Doran and Williams 1994).
Coppice management
Coppice is the oldest silvicultural system known, dating back to Neolithic times in Britain. It
was also used by the Greeks and Romans and extensively practised in Europe in the Middle Ages
(Matthews 1989). The coppice system of management starts by felling a tree which was origi-
nally planted. When felled near ground level, many species produce shoots from the stump.
These shoots come from dormant buds on the side of the stump or from adventitious buds in the
cambial layer at the edge of the cut surface (Evans 1992). Many of the millions of hectares of
eucalypts established as plantations are managed as coppice. Plantations managed only for the
production of essential oils are perhaps the most extreme form of coppice, with leaf-bearing
shoots being harvested mechanically or manually from an early age.
Why use a coppice system to regenerate the crop? Firstly, it is a very simple and reliable sys-
tem which is cheaper, and requires less expertise, than using seed or cuttings. Initial growth is
faster in the earliest stages and it is ideal where many small- to medium-sized plots are required
for pulpwood or fuel. The system is generally applied to short-rotation crops, so producing early
economic returns, and this is beneficial to resource-poor small growers. In addition, the variety
of habitat provided by different stages of coppice can be beneficial to wild plants and animals so
there is a conservation value (Matthews 1989). On the negative side, coppice grown and har-
vested on short rotations removes substantial quantities of nutrients from the site. The young
shoots can also be attractive for browsing by animals and may be prone to frost damage in some
localities. It may also be considered aesthetically less desirable than taller forest because of its
uniformity and lower canopy level.
Many eucalypts have excellent coppicing powers. The shoots arise from dormant buds in the
inner bark or from buds in the lignotuber at the base of the stem. Most eucalypts produce ligno-
tubers which consist of a mass of vegetative buds and associated vascular tissue with substantial
food reserves. When the tops of seedling or young trees are destroyed by fires, drought or grazing,
vigorous new shoots develop from the lignotuber (Pryor 1976). The absence of lignotubers in
some species, for example, E. deglupta and E. regnans, partly explains their poor coppicing ability.
Management of eucalypt coppice has been described by FAO (1981) and Evans (1992). The
ability to produce coppice is very variable and is determined mainly by the species and condition
of the stump but the season of felling may also have an effect. The eucalypt stump is best cut low
(1012 cm) with a chainsaw or bow saw to provide a smooth and sloping surface. Shoots grow-
ing from the base of the stump are generally more stable than those higher up. Stump diameter
is also important in determining the productivity of the stump. Larger stumps produce

more vigorous coppice although thick bark and very large stumps may inhibit sprouting. In
E. camaldulensis, stool productivity increased with increasing diameter except for the largest
5 per cent. One year after cutting, large stools (mean diameter 19.5 cm) supported coppice with
four times the basal area of coppice from small stools (mean diameter 7.5 cm) (Kondas 1982 in
Evans 1992).
A stump produces many shoots and whether or not these coppice shoots are thinned before
harvesting depends on the product being grown. For pole production it is usual to reduce the
number of shoots to 23 in the first year and 12 in the second year. Thinning increases the value
of the remaining stems but reduces total biomass production, although this may not be signifi-
cant, for example, Toral et al. (1988). Coppice reduction is an expensive operation and is only car-
ried out if it is essential. It is not carried out in plantations where the total above-ground biomass
is harvested to produce leaf oil, and is rarely undertaken for fuelwood production. Normally, the
yield from the first coppice crop is higher than the seedling crop, but thereafter it declines with
each cropping (Evans 1992). However, Barros and Novais (1996) report that in Brazil the first
coppice crop may have a 50 per cent reduction in productivity on some sites due to soil nutrient
depletion, especially of phosphorus. Coppicing can have a significant short-term effect on local
hydrology due to high water use as the above-ground biomass develops rapidly. Stream flow was
greatly reduced in the two years following coppicing of E. grandis and E. camaldulensis in northern
India but the effect disappeared in the third year (Bruijnzeel 1997).
The number of rotations that can be grown without replanting depends on the rate of stump
mortality and reduction in vigour of older trees. E. globulus in India has been coppiced success-
fully on a ten-year rotation for over 100 years (FAO 1981). As a general rule, three or four cop-
pice rotations can be harvested before total replanting needs to take place, as annual stump
mortality is often in the range 510 per cent. Pulpwood plantations in Brazil are managed on a
69 year rotation followed by one or two coppice crops in which no thinning is practised. As
more intensive management is applied the stock is replaced each rotation with improved genetic
material from breeding programmes. In Swaziland, although oil production has now ceased,
some areas of E. smithii managed specifically for oil were still being harvested in the early 1990s,
twenty years or more after the first cut. A rotation of approximately sixteen months was used
(Coppen and Hone 1992). Some of the lessons from general coppicing techniques will be rele-
vant for growers coppicing eucalypts for essential oil production but the regular and heavy har-
vesting of leaves in oil-yielding plantations may require the development and application of
more specialised technologies to ensure sustained production.
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4 Genetic improvement of eucalypts
With special reference to oil-bearing species
John C. Doran
Introduction
Domestication of eucalypts for oil production in plantations is in its infancy. Tree breeders have
only just started to make genetic changes to planting stock and in many instances seed for plan-
tations still comes from natural stands. Eucalypts are largely outbreeding and genetically highly
variable, which represents a huge opportunity for the tree breeder, whose main task is to exploit
this variability through exploration, evaluation, selection and breeding. In this situation, large
gains in heritable traits such as various growth and oil characteristics can be achieved simply and
cheaply using relatively unsophisticated procedures. This is in marked contrast to many agricul-
tural crops (e.g. barley, wheat and rice) that have been domesticated for thousands of years, are in
many cases inbreeding species, and where changes such as polyploidy and mutation need to be
artificially induced by breeders.
Tree breeding is worthwhile only if the subsequent economic returns are greater than its
implementation costs. In the following discussion it will be assumed that developing better
genotypes for oil production through selection and breeding is cost-effective. However, it is
recognised that this argument may well be hard to sustain at times of low eucalyptus oil prices.
Many of the principal oil-producing species, for example, Eucalyptus globulus (China), E. smithii
(Southern Africa) and E. citriodora (China, Brazil, India), are grown primarily for their wood;
eucalyptus oil is a valuable, but relatively minor, additional product. Improvement of character-
istics affecting wood production such as growth rate, form and wood quality will always be a tree
breeders first priority when working with these species. A benefit/cost analysis of incorporating
selection for oil traits in such a programme may well return a negative result. Economic analysis
should be applied to all breeding work to ensure that the benefits outweigh the cost of the
programme.
Namkoong et al. (1980) suggested that genetic improvement programmes can usefully be
grouped into three classes: those requiring low, medium or high intensity effort. The choice
between these alternatives depends upon the resources (i.e. physical, financial and human)
available and the potential economic benefits of the tree plantations (Harwood 1996). Eco-
nomics may well dictate that a relatively simple, low-input strategy is appropriate for the
genetic improvement of oil traits in eucalypts, and this will be the premise for further discussion
in this chapter. Nevertheless, successful tree breeding, whether simple or complicated, needs
scientific and technical expertise and a commitment to the provision of necessary resources in
the long term. These resources will certainly include access to chemical analytical equipment
such as gas chromatography (GC) and the expertise of an organic chemist when breeding for oil
traits. The expense of screening large numbers of plants for oil content and composition is a
consideration when determining an appropriate breeding strategy and plan.

Tree improvement programmes aim to develop new plantings superior to their predecessors
in one or several key economic traits. The modus operandi of most contemporary programmes is to
start with a carefully chosen breeding strategy implemented through a dependent breeding
plan. The breeding strategy provides a philosophy of the management of genetic improvement
while the breeding plan prescribes the nuts and bolts for implementing the selected strategy.
Typically, the plan includes a set of objectives and a flow chart of what is to be done each month
for several years ahead, and is subject to revision every 25 years (Eldridge et al. 1993).
This chapter has been prepared to serve as a guide to eucalyptus oil producers interested in
improving the yield and quality of oil through selection and breeding. As will be seen, oil traits
in eucalypts have been found to be under moderate to strong genetic control, with substantial
levels of genetic variation, and this will facilitate the capture of useful gains from relatively sim-
ple, low-input strategies appropriate to the present industry position of a static market and low
prices. The chapter highlights the principal features of breeding strategies for improving oil
traits in eucalypts and some of their key determinants, drawing on examples from the main
oil-producing species where appropriate. In doing so, extensive use is made of three practical
texts that are highly recommended to any newcomer to eucalypt breeding: Eldridge et al.
(1993), Williams and Matheson (1994) and Cotterill and Dean (1990). These in turn introduce
the reader to other literature important to understanding tree breeding and forest genetics.
Basic concepts
Most worthwhile breeding strategies recommend starting with a well-adapted population with
a broad genetic base. This base population is then subjected to a particular method and intensity
of selection. Selected trees are then mated to maximise long-term genetic gain and minimise the
effects of inbreeding within the limits imposed by human and economic resources.
Selection and mating are key activities in breeding. They accumulate genes which influence
yield and adaptation, steadily increasing over successive generations the frequency of superior
genotypes. Every successful breeding strategy, therefore, requires efficient methods of selecting
superior genotypes. These methods include the progeny tests in which the selection is carried
out, appropriate measurement techniques and selection technology (e.g. selection indices).
Mating can be done by open pollination or controlled pollination, carefully minimising the
potential for inbreeding and allowing for genetic material from other sources to be incorporated.
In pursuing its principal functions of efficient selection and mating, a strategy should aim to
assess the variation within a species, generate information about it and ensure that genetic
resources and variation for future selections are conserved (Barnes 1987, Matheson 1990).
The cyclic or recurrent nature of the selecting, testing and mating processes which are part of
an overall breeding strategy is illustrated in Figure 4.1. Every effective breeding strategy
involves maintaining a hierarchy of three major types of population which can continue to meet
the demand for genetically improved planting stock for the fourth population, the production
population (i.e. commercial plantations) (Griffin 1989a, Matheson 1990, Eldridge et al. 1993).
These populations are the base, breeding and propagation populations. Awareness of the concept
of maintaining distinct types of population within the cycle is essential in planning
the operations of genetic improvement (Libby 1973), even if circumstances dictate that some
populations are combined in the one planting.
Breeding objectives
When oil production is the sole objective of a eucalypt plantation, the usual goal of producers is
to maximise the yield of high quality oil if it is economically feasible to do so. The yield of oil

Base Breeding Propagation Oil-producing
population population population population
Progeny Selection Seed Mass

Base Plantation
testing orchards/clone
propagation
banks
Mating
Selected
trees
Figure 4.1 Activity cycle for breeding and the hierarchy of the four populations relevant to breeding
strategies and operations.
from a given area of land depends on the species planted, available leaf biomass and the concen-
tration of oil in those leaves at that point in time. Oil composition usually determines quality
and will be an important consideration if it is liable to variation in the species under cultivation
and affects the marketability or price of the oil produced.
A typical breeding objective for an oil-producing species would therefore be to increase the
yield of high quality oil per unit area. This can be done by improving the yield of leaves, and the
concentration of oil in those leaves, and ensuring that the quality of the oil produced maximises
saleability and price.
Choice of base material

Correct choice of base material is critical to the success of breeding programmes. There are many
examples in eucalypt breeding where breeding has begun with a poor choice of species or prove-
nance and, in others, where the genetic base was much too limited (Eldridge et al. 1993). In the
following discussion it is assumed that the choice of preferred species for oil production has
already been made. The aim, then, is to point out important factors for consideration in acquir-
ing suitable germplasm of a particular species with which to establish breeding populations.
Examples pertaining to the main oil-producing species in use today (i.e. E. citriodora, E. dives, E.
exserta, E. globulus, E. polybractea, E. radiata, E. smithii and E. staigeriana), as well as some with
high potential (e.g. E. camaldulensis and E. kochii), are given wherever possible.
Knowledge of the genetic structure of natural populations is important in determining strate-
gies for seed collections for breeding programmes. Studies of the amount and distribution of
genetic diversity in eucalypt species, as assessed by allozyme variation, have shown that, on
average, 18 per cent of the genetic diversity in the twenty-five species studied to date occurs
between populations (Moran 1992). The species with most genetic differentiation between
populations are those with regional (i.e. moderately extensive) distributions but with small
disjunct populations. Regionally-distributed eucalypts had, on average, a higher proportion of
variation between populations (25 per cent) than localised or widespread (14 per cent) species.
Of the regionally-distributed species, those with disjunct distributions show greater

population differentiation (39 per cent) than those with continuous distributions (11 per cent).
Generally, however, most of the allozyme variation occurred within, rather than between,
populations.
Genetic resources
After defining the objectives of the breeding programme, the next task in tree breeding is to
establish a breeding population. Where selection aims to enhance oil production the natural
inclination is to start by making selections in local plantations of the preferred oil-yielding
species to establish a breeding population. In many instances this is a perfectly good strategy.
However, there are some pitfalls in relying solely on existing plantations (land races) as the
primary source of selections for breeding populations. The genetic history of many eucalypt
plantings is obscure or unknown. Many have a narrow genetic base and have been derived from
a provenance that gives mediocre performance in the environment of the planting site. This
situation has existed with many species in numerous countries and trials of broadly based seed
collections from the natural provenances of a particular eucalypt have often shown better adapta-
bility and faster growth rate than the local land race, even after genetic improvement of the land
race (see examples in Eldridge et al. 1993).
Any new programme should start with a thorough review of provenance performance within
the region of planting. It may well be found that, given the uncertain origins of the land race
and the lack of systematic provenance testing in the past, it is preferable to start again, virtually,
by introducing broadly based provenance collections from natural stands of the target species. If
there is a clear indication that some provenances or regions-of-provenance are better than others,
collections can be concentrated in those areas. These, and collections representing the best ele-
ments of the local land race, can then be used to establish large provenance-progeny trials. Such
trials have multiple functions including ranking provenances and land races, serving as breeding
populations for the first generation, providing resources for selection and breeding activities,
and as commercial seed orchards. Several breeding strategies developed for wood-producing
Eucalyptus species have advocated this approach, for example, E. globulus in China (Raymond
1988) and E. camaldulensis in Thailand (Raymond 1991).
Choice of trees within species
Chemical forms
An extreme type of variation within species, commonly found in Eucalyptus and in a wide variety
of other plant families, is the occurrence of chemical forms. Penfold and Willis (1953)
described these as
plants in naturally occurring populations which cannot be separated on morphological evi-

dence, but which are readily distinguished by marked differences in chemical composition
of their essential oils.
They do not differ qualitatively but show marked discontinuous, quantitative variation
(Hellyer et al. 1969).
Penfold and Morrison (1927) first reported such forms in E. dives and called the variants
physiological forms. In order to distinguish four separate and distinct oil forms in the species
they called them Type, Variety A, Variety B and Variety C in order of discovery. The use of

Table 4.1 The range in abundance of four key compounds in the oils of six
chemical forms in a population of Eucalyptus radiata (Johnstone 1984)
1,8-Cineole (%) !-Phellendrene (%) Piperitone (%) Terpinen-4-ol (%)
212 427 2155 0226

727 333 0.810.5 0237
427 323 019 1236
923 17 16 1428
3060 320 06 0223
5876 120 13.5 16
Orange
Tumut
Mt Buffalo
Yowrie
Figure 4.2 The natural distribution (black dots) of Eucalyptus radiata in southeastern Australia as plot-
ted from authenticated botanical specimens, showing the four regions Mt Buffalo, Orange,
Tumut and Yowrie (circled) where Johnstone (1984) found most trees to give foliar essen-
tial oils of the high-cineole form.
this terminology has now been discontinued in favour of simply referring to the different types
as chemical variants, chemical forms, chemovars or chemotypes, and highlighting the major oil
component, for example E. dives (cineole variant) (e.g. see Lassak 1988). Chemical forms do not
appear to be the result of site differences, seasonal variation (Simmons and Parsons 1987), leaf
ageing effects or hybridisation.
Chemical forms, as highlighted in Chapter 5, abound in several of the principal oil-producing
eucalypts: E. camaldulensis has five chemical forms, E. citriodora four forms, E. dives five forms and
E. radiata six forms. The compositional types of E. radiata are shown in Table 4.1. Each form
may occur in separate, distinct populations (chemical races), but they can also be present
together on the one site and maintain their chemical integrity despite interbreeding. Differences
in chemical form do not appear to be associated with differences in oil yield.
In a study of fifty E. radiata trees in a single population containing three distinct chemical
forms, Whiffin and Bouchier (1992) concluded that the forms appear to be the result of the
actions of the enzymes which control terpenoid biosynthesis modifying a basic monoterpene
pool. In E. camaldulensis, a high-spathulenol form was reported to occur at a frequency of one in
ten trees amongst high-1,8-cineole forms at Petford in northern Queensland (Doran and Brophy

1990). In a progeny trial of Petford families, the high-spathulenol forms could not be
distinguished from the high-1,8-cineole forms until plants were 1825 months old, suggesting
that diversion of the monoterpene pool is linked to maturation processes and the activation of
specific enzymes (Doran 1992).
The potential importance of chemical forms, either positively as a rich source of desirable
chemicals or negatively as adversely affecting the quality of oil, has been noted by Hillis (1986).
In choosing populations within a species as the genetic resources for a tree-breeding programme,
it is preferable to concentrate on populations containing a single chemical form. In E. radiata,
for example, Johnstone (1984) identified only four populations, from many sampled throughout
the range of the species, where most trees were of the commercially valuable high-cineole form
(Figure 4.2). These are the obvious populations to target in seed collections for base populations
of this chemical form of the species. However, such a strategy may not be feasible when dealing
with species or provenances where desirable (that is commercially valuable) and non-desirable
chemical forms co-occur, as is the case with Petford E. camaldulensis. When dealing with popula-
tions with multiple forms, seed trees of the desirable, commercial oil type should be selected and
segregating progeny removed from the breeding population as soon as they can be confidently
identified.
Provenances
When breeding a species for oil production, the primary goals are to maximise the yield of
leaves that contain the highest possible concentration of oil of a composition which gains a
premium price in the market place. The yield of leaves is usually highly correlated with diameter
growth.
There is now ample evidence that much faster growth and greater oil yields of eucalypts in
plantations can be obtained through careful selection of provenance and genetic improvement
(Eldridge et al. 1993). In a study of provenance variation in E. globulus, Doran and Saunders
(1993) found highly significant differences between provenances, and amongst families within
provenances, for three principal oil traits (concentration of oil in the leaf, concentration of
1,8-cineole in the leaf and cineole content of the oil) and for stem diameter at breast height in
trees aged 1.75 years (juvenile foliage) and 2.75 years (mature foliage) in provenance/progeny
trials in New South Wales and Victoria respectively. The results of the younger trial are sum-
marised in Figure 4.3. Families from the Otways/Lorne and Jeeralang provenances consistently
ranked among the best in leaf oil concentrations and were among the fastest growing sources.
These would be the provenances favoured to provide candidates for breeding populations should
breeding E. globulus for oil production in southern Australia be contemplated.
Families
Phenotypic (genotype " environment) variation between trees in natural populations in such
traits as oil concentration and oil composition is very large. Frequency diagrams for oil concen-
tration and 1,8-cineole content in regions-of-provenance of two important oil-yielding species,
E. polybractea from West Wyalong and E. radiata from Nerrigundah-Yowrie, are given in
Figure 4.4. As such traits are highly heritable, it is desirable to screen trees in the native stands
for these traits and select as seed trees for breeding populations only those that rank amongst the
best for both traits. Breeding programmes for oil production using mallee eucalypts, including
E. polybractea (Western Australia), and E. radiata (Australia and South Africa) have employed
this strategy (Donald 1980, 1991, Bartle 1994, Doran et al. 1998).

(a) (b)
4 LSD = 0.49 LSD = 0.49

5
SED = 0.25 SED = 0.25
Oil conc. (% w/w, dry matter basis)

4
3
Diameter (cm)
3
2
2
1
1
0 0
4 2 6 1 9 5 7 8 3 10 1 9 2 3 4 7 6 8 5 10
Provenance Provenance
(c) (d)
1,8-Cineole conc. (% w/w, dry matter basis)
LSD = 0.18 LSD = 1.34

2 60 SED = 0.92
SED = 0.09
50
1,8-Cineole content (%)
40
1 30
20
10
0 0
1 9 3 2 4 7 6 8 5 10 4 6 3 1 5 7 8 9 2 10
Provenance Provenance
Figure 4.3 Variation amongst provenances of Eucalyptus globulus at 1.75 years of age in (a) stem diameter,
(b) oil concentration in leaves, (c) 1,8-cineole concentration in leaves, and (d) 1,8-cineole con-
tent of oil. The caps above the bars represent the standard error of the difference (SED) between
provenances. Provenance identification: 1 # Otways, 2 # Jeeralang, 3 # West Coast, 4 # Cape
Barren, 5 # King Island, 6 # Flinders Island, 7 # Moogara, 8 # Geeveston, 9 # Lorne,
10 #South Gippsland.
Progeny
Even when trees have been selected in the natural stands for such traits as oil concentration and
cineole content, their open-pollinated seed will give progeny which are highly variable in these
traits. This variation provides further opportunity for selection between the breeding population
and propagation population phases of the breeding strategy. Figure 4.5 illustrates the variation
in oil yield per tree in one family of a southern New South Wales provenance of E. radiata
(Doran et al. 1998).
Typically, there is substantial variation in commercial oil traits at all levels of the selection
hierarchy in most, if not all, of the main oil-producing species. A commonly repeated scenario is

80 80
E. polybractea E. polybractea
70 70
60 60
50 50
No. of trees
No. of trees
40 40
30 30
20 20
10 10
0 0
2. 1.9
3. 2.9
4. 3.9
5. 4.9
6. 5.9
7. 6.9
8. 7.9
9. 8.9
.0 9.9
.0 4.9
.0 9.9
.0 4.9
.0 9.9
.0 4.9
.0 9.9
.0 4.9
.0 9.9
.0 4.9
9
9.
9.
50 4
55 5
60 5
65 6
70 6
75 7
80 7
85 8
90 8
95 9
9
0
0
0
0
0
0
0
0
0
0.
.0
45
Oil conc. (% w/w, dry matter basis)
1,8-Cineole content (%)
E. radiata E. radiata
25
30
20 25
20
No. of trees
15
No. of trees
15
10
10
5
5
0 0
.0 .9
.0 .9
.0 .9
.0 .9
.0 .9
.0 .9
.0 .9
9
.0 .9
.0 .9
8. 7.9
.0 1.9
.0 3.9
.0 5.9
2. 1.9
4. 3.9
6. 5.9
3.
7.
63 62
66 65
69 68
72 71
75 74
78 77
81 80
59
10 9
8
12 1
14 1
16 1
1
0
0
0
0
.0
0.
60
57
Oil conc. (% w/w, dry matter basis) 1,8-Cineole content (%)
Figure 4.4 Frequency distributions of oil concentration in foliage and 1,8-cineole content of oil in
Eucalyptus polybractea from West Wyalong, New South Wales, and E. radiata from the
Nerrigundah-Yowrie region of southeastern New South Wales.
that reported for E. globulus (Doran and Saunders 1993) and illustrated in Figure 4.6. The high
level of variation in oil concentration in all the provenances sampled can be seen. This variation
provides the opportunity to select trees for this trait from almost the entire natural range of the
species, despite the presence of significant provenance and family within-provenance variation.
Biological characteristics influencing choice of breeding strategy
Breeding system and inbreeding depression

Eucalypts have hermaphrodite, protandrous flowers and are pollinated by insects or birds
(Griffin 1989a). They reproduce by a mixed mating system, with both outcrossing (where the

250
200
Oil yield/tree (g)
150
100
50
0
T1 T2 T3 T4 T5 T6 T8 T9 T11 T12
Tree number
Figure 4.5 Variation in oil yield per tree in a replicate of one family in a 23-month-old Eucalyptus
radiata progeny trial.
12
Oil concentration (% w/w, dry matter basis)
10
0
5 1 2 10 9 3 4 6 7 8
Provenance
Figure 4.6 Variation in oil concentration in juvenile leaves in a 1.75-year-old Eucalyptus globulus
provenance-progeny trial in southeastern New South Wales. The box represents the
interquartile range, the whiskers represent the outerquartile range and the circles indicate
outliers. The horizontal line within each box is the provenance median value. Provenance
names are given in Figure 4.3.
pollen from one tree fertilises the flowers of another tree) and selfing (pollination of an indivi-
dual tree or clone with its own pollen) (Moran 1992, Moran and Bell 1983). The proportions of
outcrosses and inbreeds reported in seed collected from natural populations range from
45 per cent outcrossing in one population of E. pellita (House and Bell 1996) to 97 per cent
outcrossing in E. camaldulensis (P.A. Butcher pers. comm.).

Controlled pollination experiments on E. regnans (Eldridge and Griffin 1983) showed that
selfed (inbred) seed produced seedlings which grew markedly slower than those from open-
pollinated seed from the same parent trees. At age nine years, height was 12 per cent less, and
stem diameter 19 per cent less, for trees raised from selfed seed compared with those raised from
open-pollinated seed. This is equivalent to a reduction in wood volume of nearly 50 per cent in
the selfed trees at this age, compared to open-pollinated seed (which would itself include about
2530 per cent of selfed seeds and 70 per cent of outcrossed seeds). A few years later nearly all
the selfed trees in the trial were suppressed and many were dead. This reduced performance of
selfed seed has been shown to hold true for other eucalypts, such as E. camaldulensis and E. grandis,
and for many other tree species (Sedgley and Griffin 1989).
Inbreeding results not only from self-fertilisation, but also from the mating of closely related
individuals, such as trees descended from the same mother. Adjacent trees in natural forests will
often be closely related. Levels of inbreeding can be reduced in well-designed seed orchards or
seed production areas, in which many unrelated genotypes are represented and adjacent trees are
not related. In a seed orchard of E. regnans, the outcrossing rate was estimated to be 91 per cent,
compared with 74 per cent in a nearby natural population (Moran et al. 1989).
Cases of a progressive narrowing of the genetic base and associated deterioration in perfor-
mance are frequent in the history of overseas introductions of eucalypts. For example, a limited
introduction of E. nitens to South Africa in 1930 produced a land race which was so severely
inbred after several generations that it was discarded in favour of new importations of seed from
Australia (Purnell 1986).
In summary, selfing in eucalypts has detrimental effects on growth rate and seed set. Seed
orchards should have a broad genetic base and adequate cross-pollination between trees to
minimise self-fertilisation.
Genetic control of oil traits

Several authors have proposed single gene control of the production of particular monoterpenes
(e.g. Squillace et al. 1980), usually with a dominant/recessive pair of alleles. However, these
conclusions have been questioned because of invalidity of the assumption of independence of
each variable (Birks and Kanowski 1988). Based on a review of inheritance studies of coniferous
resin, Birks and Kanowski (1988) concluded that there was little, if any, unambiguous evidence
of simple Mendelian inheritance of resin components. The oil traits of most interest for selec-
tion, such as oil concentration and yield of 1,8-cineole, are most likely governed by a complex of
genes (Doran 1992).
In breeding programmes for oil production in eucalypts, the main traits for selection are
quantitative traits for which the variation is continuous, such as growth rate and oil concentra-
tion. Thus the genetics of breeding eucalypts for oils is predominantly quantitative genetics.
Recent studies of the oils of various species of Eucalyptus using quantitative genetic methods
have indicated moderate to strong genetic control of oil concentration and composition.
Available estimates of genetic parameters for commercial traits in eucalypts are summarised
below.
Genetic parameters
In manipulating quantitative characters the plant breeder deals with the nature, magnitude and
inter-relationships of genetic and non-heritable variation (Allard 1960). Defining genetic varia-
tion is one of the first tasks of tree breeding. This variation is expressed by estimates of genetic

parameters, each of which is a numerical quantity which specifies a population in respect to
some characteristic (Allard 1960).
Reliable, unbiased estimates of genetic parameters from well-designed field trials are essential
to permit a realistic appraisal of rate and magnitude of improvement by selection and to compare
possible alternative strategies (Eldridge et al. 1993).
Additive and non-additive genetic variance Genetic variance (VG) is made up of two parts: an
additive part (VA), due to average effects of genes, and a non-additive part (VNA), due to such
deviations from additivity as dominance (the masking effect of one allele by another allele at the
same gene locus) and epistasis (interaction of genes at different loci) (Matheson 1990). Thus,
VG #VA "VNA. The gains from recurrent selection are due to the accumulation of genes which
act independently (additive effects). Non-additive effects caused by interactions between genes
are unavailable in future generations as these effects break down with random assortment
and recombination by meiosis during sexual reproduction. Gains from non-additive effects can
be exploited only by controlled pollination to produce outstanding specific crosses, or clonal
propagation of outstanding individuals.
Non-additive genetic variance for a particular trait, using the concept of specific combining
ability (SCA), can be estimated from full-sib progeny tests where controlled pollinations have
been carried out in a pattern best suited for such estimates, for example, diallels (all possible
combinations of crosses) or partial diallels (a subset of all possible crosses) (Matheson 1990).
Here, the expected value for trait X in progeny of the cross of parents A and B is calculated as the
population mean for all crosses " general combining ability (GCA) of parent A (i.e. the
difference between the population mean and the mean for all crosses involving parent A) "GCA
of parent B. The difference between the actual value for trait X and the calculated expected
value is the SCA, resulting from non-additive gene action. These deviations from the expected
value may be positive or negative; the positive effect is usually of most interest to the tree
breeder.
The level of SCA for growth traits in Eucalyptus has been discussed by Eldridge et al. (1993).
There are very few estimates available of SCA for oil traits in this genus, mainly because of the
lack of suitable trials. Preliminary estimates of GCA and SCA effects for 1,8-cineole yield in
twelve-month-old E. camaldulensis progenies in a full-sib progeny test indicated that additive
variation exceeded non-additive variation by a ratio of 6 : 1 (Doran 1992). The three control-
pollinated families with the greatest 1,8-cineole yields ranked highest, apparently because at
least one of the parents was a good general combiner and moderately high levels of SCA were
also present. This result mirrors what has been determined for growth traits, where additive
genetic variance is usually greater than the non-additive component, but useful amounts of the
latter are present for utilisation in clonal programmes.
Heritability Heritability (h2) in the narrow sense of the term is the ratio of additive genetic
variance (VA) to the total phenotypic variance (VP, where VP # VA "VNA " VE) (Falconer 1989).
VE is the environmental variance. Put simply, it is a measure of how strongly a trait is influenced
by genetics and how much by environment (Hanson 1963). Genetic gain from selection and
breeding is potentially high when heritability is high. Heritability estimates are needed if selec-
tion is to be assisted by use of an index and are very useful for estimating potential genetic
gains from alternative breeding strategies. They are calculated by parent-offspring regression or
from variance components estimated by statistical analysis of progeny test data. Ideally, progeny
trials test many families and are designed to minimise VE. Eldridge et al. (1993) list several

factors that need qualification when heritability estimates are used, including acknowledgement
that each estimate pertains only to the particular population and environment from which the
data used for the calculation were derived.
Estimates for heritability (hi2 narrow sense, individual heritability) for the principal traits
affecting commercial production of eucalyptus oil are given in Table 4.2.
The principal eucalyptus oil traits in the species indicated appear to be under moderate to
strong genetic control, with mean individual heritability estimates of 0.110.54 for oil concen-
tration in the leaves, 0.270.61 for cineole concentration in the leaves and 0.370.61 for cineole
content of the oil. Most of these estimates are based on relatively small numbers of families and
come from open-pollinated progeny trials, sometimes of a design that is not ideal for estimating
heritabilities (e.g. Barton et al. 1991, Doran and Saunders 1993). Much remains to be done
before reliable estimates of the heritability of oil traits are available for the major oil-
producing eucalypts. However, confidence in the available estimates is boosted by their similar-
ity to heritabilities reported for an oil-producing species from a closely related genus, Melaleuca
alternifolia, the source of Australian tea tree oil. In M. alternifolia, heritabilities for oil concentra-
tion in the leaves were 0.67 and 0.51, and for cineole content of the oil 0.37, when estimated in
Table 4.2 Individual (h2i ) and family (hf2 ) heritability estimates from open-pollinated progeny tests for
commercial traits in some Eucalyptus species used in oil productiona
Trait Speciesb hi2 hf2 Age No. of Reference

(yr) families
Cineole conc. CML 0.53d 0.62 3.75 19 Doran and Matheson (1994)
in leaf c 0.61e 3.75 19
GLB 0.34 2.75 80 Doran and Saunders (1993)
0.27 1.75 80
KOC 0.83 3.8 50 Barton et al. (1991)
POB 0.36 2.4 11 Grant (1997)
Cineole GLB 0.48 2.75 80 Doran and Saunders (1993)
content of oilf 0.37 1.75 80
POB 0.61 2.4 11 Grant (1997)
Oil conc. in leaf c CML 0.54d 3.75 19 Doran and Matheson (1994)
0.42e 3.75 19
GLB 0.11 2.75 80 Doran and Saunders (1993)
0.27 1.75 80
POB 0.36 2.4 11 Grant (1997)
Stem volume GLB 0.19 6.0 45 Volker et al. (1990)
per tree
Tree height GLB 0.12 6.0 45 Volker et al. (1990)
0.29 4.0 36 Borralho et al. (1992)
Stem GLB 0.24 6.0 45 Volker et al. (1990)
diameter g
Stem sectional GLB 0.13 4.0 36 Borralho et al. (1992)
areag
Stem form GLB 0.22 6.0 45 Volker et al. (1990)
a A coefficient of relatedness of 0.4 was used in calculating hi2 for oil traits.
b CML #E. camaldulensis, GLB #E. globulus, KOC #E. kochii, POB #E. polybractea.
c %, w/w (dry matter basis).
d, e Mtao and Forest Hill, respectively, Zimbabwe.
f Relative abundance, %.
g Measured at breast height.

two well-designed provenance-progeny trials in northern New South Wales (Butcher et al. 1996,
Doran et al. 1997).
The oil yield to be expected from a plantation is the product of leaf biomass and oil concen-
tration. Leaf biomass of an individual tree is typically highly correlated with stem diameter and
height, as demonstrated by the significant correlations between the two indirect measures of
leafiness, crown surface area and crown density, and stem diameter and height for E. camaldulensis
shown in Table 4.3a. Heritability estimates for stem diameter and height for eucalypts generally
fall in the low-to-moderate range, as exemplified by the figures for E. globulus given in
Table 4.2. Nevertheless, useful gains can be made by selection and breeding in these traits and
they should be included along with oil characteristics in the list of traits for selection in breeding
programmes for oil production.
Genetic and phenotypic correlation Genetic correlations (rg) are calculated as the correlation of
the breeding values of two traits and express the extent to which these traits are influenced by
the same genes (Falconer 1989). Genetic correlations are important for predicting the magni-
tude and direction of response in one trait to selection for another, as well as for a number of
other useful purposes (Williams and Matheson 1994). Genetic correlations have some influence
on the best way to structure breeding populations. For example, where there are strongly nega-
tive genetic correlations between two traits, it is very difficult to breed for them both in the one
population and it may be necessary to divide the population. Strong positive genetic correla-
tions, on the other hand, are useful in reducing the number of traits for selection, as selection for
one of the correlated traits will be effective in improving the other trait. Phenotypic correlations
(rp), which include genetic and environmental components, are simply calculated from the cor-
responding measurements of two traits and are of much less importance to the tree breeder.
Sometimes there is a large difference between genetic and phenotypic correlation coefficients,
Table 4.3a Estimates of genetic (above the diagonal) and phenotypic (below the diagonal) correlations
between growth and oil traits for 3.75-year-old Petford Eucalyptus camaldulensis at Mtao,
Zimbabwe (Doran and Matheson 1994)
Tree Stem Crown Crown Cineole Oil conc.

height diameter a surface density conc. in in leaf b
area leaf b
Tree height 0.818 0.666 0.481 0.044 $0.481

(0.139)c (0.202) (0.303) (0.295) (0.260)
Stem 0.769 0.816 0.477 $0.100 $0.456
diameter a (0.171) (0.348) (0.358) (0.333)
Crown 0.618 0.751 0.467 $0.104 $0.466
surface area (0.344) (0.341) (0.311)
Crown 0.421 0.482 0.445 0.233 $0.139
density (0.371) (0.385)
Cineole conc. 0.041 $0.071 $0.079 0.185 0.803
in leaf b (0.109)
Oil conc. in $0.427 $0.350 $0.365 $0.096 0.806
leaf b
a Measured at breast height.

b %, w/w (dry matter basis).
c Figures in parentheses indicate standard errors for genetic correlations.

even to the extent that one might show a positive association between traits while the other is
negative (Eldridge et al. 1993).
There are few examples of genetic correlations for oil traits in the literature. Table 4.3a shows
estimates of phenotypic and genetic correlations from a progeny test of E. camaldulensis (Doran
and Matheson 1994). The estimated genetic and phenotypic correlations between growth traits and
1,8-cineole yield were small with large standard errors for the genetic correlation coefficients.
Although these estimates lacked precision, it appears that these characters are weakly associated
and selection for one is unlikely to affect the other, either adversely or favourably. However, oil
concentration, as estimated by the concentration of monoterpenoids in leaves, and growth traits
showed moderate and unfavourable genetic and phenotypic correlations. These genetic correla-
tions had very large standard errors and were considered unreliable by the authors. Since max-
imising yields of 1,8-cineole was the more important breeding objective, no adjustment of the
breeding strategy to cater for the adverse genetic correlation was advocated. 1,8-Cineole yield
and oil concentration were, as expected, strongly associated, with an rg of 0.80 (se #0.11) and an
rp of 0.81. The positive genetic and phenotypic correlations between stem diameter and height
and the crown traits of surface area and crown density were considered beneficial because total
oil production depends not only on oil concentration in the leaves but also on total leaf biomass.
Table 4.3b shows estimates of phenotypic and genetic correlations from a progeny test of
E. polybractea (Grant 1997). Here there was a strong positive genetic correlation between oil
yield per tree and leaf biomass (rg of 0.85). The large negative genetic correlations between oil
traits and the average area of individual leaves are in agreement with other data, indicating that
the larger-leaved forms of the species are poorer oil producers than the narrow-leaved forms.
In a provenance/progeny trial of Melaleuca alternifolia, Butcher et al. (1996) reported a strong
negative genetic correlation (rg of $0.42) between oil yield and plant dry weight. In breeding to
improve oil production in M. alternifolia, and faced with an apparent adverse genetic correlation,
these authors recommended combined index selection (Cotterill and Dean 1990) with a
Kempthorne type restriction (Cotterill and Jackson 1981, Cotterill and Dean 1990) imposed on
plant dry weight to prevent decline in this trait as a means of maximising genetic gains. In
another trial of this species, basal stem diameter, a trait closely correlated with plant dry weight,
showed no adverse genetic correlation with oil yield (rg of $0.14), reinforcing the qualification
that genetic parameters are specific to the population of trees from which the data were collected
and the conditions of the planting site (Doran et al. 1997).
Table 4.3b Estimates of genetic (above the diagonal) and phenotypic (below the diagonal) correlations
between growth and oil traits for 2.4-year-old Eucalyptus polybractea at West Wyalong, New
South Wales, Australia (Grant 1997)
Oil conc. Cineole Cineole Oil yield Area per Leaf

in leaf a conc. in content per tree leaf biomass
leaf a of oil b
Oil conc. in leaf a 0.919 0.379 0.738 $0.295 $0.174

Cineole conc. in leaf a 0.917 0.684 0.512 $0.361 $0.016
Cineole content of oilb 0.317 0.648 $0.338
Oil yield per tree 0.494 0.428 0.155 0.148 0.846
Area per leaf $0.342 $0.455 $0.449 0.007 0.395
Leaf biomass 0.027 $0.009 $0.065 0.836 0.215
a %, w/w (dry matter basis).

b Relative abundance, %.

Juvenilemature correlation (ageage correlation) Juvenilemature correlation, also known as
ageage correlation, is a form of traittrait genetic correlation (Eldridge et al. 1993). When
there is a large positive genetic correlation between a trait in young trees and the same trait in
older ones, selection can be made at an early age and the rate of genetic gain is correspondingly
improved.
Attempts to select eucalypts for oil characteristics in the nursery and at very young ages in
plantations have been largely unsuccessful. Barton et al. (1991) found no qualitative variation
between parents and progeny in E. kochii, but they did report significant quantitative variation
with the age of the plant. Juvenile leaf from six-month-old seedlings grown in the glasshouse
was lower in cineole and higher in terpene hydrocarbon yields than leaf from the parents. The
same seedlings planted in a field trial were sampled at eighteen months and three years: cineole
yield increased steadily and at three years closely resembled parent values. A similar result was
reported for E. citriodora, where it took three years of growth for oil and citronellal content of
progeny to attain stable levels (Mascarenhas et al. 1987).
Doran (1992) studied the variation in 1,8-cineole concentration in controlled cross progeny of
E. camaldulensis at regular intervals up to twenty-five months from planting. Correlations
between offspring and mid-parent values were poor (r # 0.230.55) until twenty two months,
when r reached 0.76. Correlation improved to 0.86 at twenty-five months, although the level of
cineole in the progeny of several crosses was still increasing, suggesting that further changes in
ranking with age might take place. This study included progeny of a distinctive high-spathu-
lenol chemotype. These non-commercial chemotypes could not be distinguished from the high
1,8-cineole forms until plants were 1825 months old, an observation which provided another
incentive to delay selection until at least twenty-five months.
It appears that the earliest age that trees in eucalypt breeding populations can be reliably
ranked for oil traits is about three years. This is still relatively early as general heavy flowering in
most species would not occur until some years later.
Genotype % environment interaction The statistical expression, genotype % environment interac-

tion (GEI), is applied when genotypes grow differently relative to each other in different envi-
ronments. It is estimated by analysing data from two or more trials of the same clones or seedlots
and by joint regression analysis to obtain regression coefficients to measure the stability of
families across sites for the trait in question (Matheson and Cotterill 1990, Williams and
Matheson 1994).
In a study of variation in the two-year growth of extensive provenance-progeny trials of
E. camaldulensis on three sites in Thailand, Pinyopusarerk et al. (1996) reported significant
site % family interaction for height, stem diameter and stem volume growth. A marked differ-
ence in stability of families across sites was found and provenances from Petford and the Thai
land race were more unstable than other provenances, that is they performed very well at good
sites but not so well (in relative terms) at poorer sites. This mirrors what has been reported for
other tree species such as Pinus radiata (Matheson and Raymond 1984). The results have impli-
cations for future selection and breeding of E. camaldulensis in Thailand. For example, it may be
necessary to breed for commercial traits in different environments using a multiple-population
breeding option. If a common breeding population is to be adopted it will be necessary to place
more emphasis on selecting the seedlots that have shown good general adaptability over several
test sites.
In breeding for oils, the extra analytical costs of assessing oil traits is a significant constraint
on dividing the breeding population into regional groups, or into sublines. The breeder will be
looking for genotypes which are relatively stable over all the proposed planting sites for

manipulation in a single breeding population. The critical trials to determine if this is a viable
option, ideally using clones on a range of sites, have still to be established for most of the major
oil-producing eucalypts.
Hybridising ability
Griffin et al. (1988) reviewed the occurrence of natural and manipulated inter-specific hybrids
within the genus Eucalyptus, and confirmed the long-standing hypothesis that within sub-genera
there are generally no strong barriers to the production of hybrid seed following cross-pollination.
Hybrids may be desirable because they are heterotic or because they combine traits that were not
found together in either parental species (Griffin 1989b). Sites which are marginal for pure
species have provided, so far, the most successful habitats for use of eucalypt hybrids. For exam-
ple, hybrids of E. grandis with hardier species such as E. urophylla, E. camaldulensis and
E. tereticornis are showing great promise on sites in South Africa which, because of drought, are
marginal for growing pure E. grandis (Van Wyk et al. 1989).
Leaf oil composition has sometimes assisted botanists to detect eucalypt hybrids, for example,
E. ovata % E. crenulata (Simmons and Parsons 1976) and E. alpina % E. baxteri (Whiffin and
Ladiges 1992). Pryor and Bryant (1958) showed that the essential oils of interspecific hybrid
progeny vary greatly but usually give compositions which are intermediate between those of the
parents. Transgressive compounds, which occur in higher proportions than in either parent, have
been reported in E. ovata % E. crenulata (Simmons and Parsons 1976), possibly resulting from
enzyme complementation.
To date, there has been little interest in applying hybridisation to the improvement of oil-
producing eucalypts. An exception is the interest being shown in Brazil in the hybrid between
E. citriodora and E. torelliana (L. Couto pers. comm.). Here, the aim is to incorporate the better
crown shape and density and coppicing ability of E. torelliana into the breeding programme.
Whether or not this can be achieved by recurrent selection for general combining ability (addi-
tive gene effects) in both species or whether it requires the more complex procedures of reciprocal
recurrent selection (Nikles 1993, Dieters et al. 1995) has still to be determined.
Ease of vegetative propagation

In tree breeding, vegetative propagation is commonly used for the establishment of clone banks
and clonal seed orchards, and can be utilised for the production population if the species in
question lends itself to mass propagation by this means. Clonal forestry generally relies on propa-
gation by stem cuttings rather than micropropagation, which is usually too expensive (Haines
1994). Clonal forestry is now practised with several eucalypt species (e.g. E. camaldulensis,
E. globulus, E. grandis, E. gunnii, E. tereticornis, E. urophylla and their hybrids) and work is
continuing to master the technique with other commercial species such as E. nitens. A summary
of the methods employed with different species is provided by Eldridge et al. (1993).
Of the important oil-yielding eucalypts, mass propagation by cuttings is currently practised
only with E. camaldulensis. Doran et al. (1992) and Doran and Williams (1994), for example,
describe a programme of selection for rooting ability in combination with growth and oil traits
within the tropical E. camaldulensis provenance of Petford. The use of cuttings is made more
attractive in this species by the substantial and quick gains that can be made in yield and oil
quality, as these traits are highly variable and at sub-optimal levels in unselected seedling stock.
The high overall selection intensity required, due to selection simultaneously for several traits,

and particularly rooting ability (only 30 per cent of clones passed the selection criteria for
rootability), reinforced the need to start with a broad genetic base.
Micropropagation by tissue culture of genotypes of E. radiata selected for oil production in
South Africa was recommended by Donald (1991) as a means of improving oil yield in this
species. This was an alternative to striking cuttings from coppice shoots which is difficult in this
species. However, the expense of micropropagation is unlikely to be justified in the present market.
Vegetative propagation as a tool in improving oil yields, therefore, is likely to be practised on
only a small scale at present. It does, however, offer an excellent opportunity with easily rooted
species to quickly exploit the gains from breeding by employing mass vegetative propagation to
establish the production population. The costs and benefits of such a programme need first, of
course, to be carefully considered.
Flowering and seed production

In their natural environment, most eucalypts are prolific seed producers and it is generally not
difficult to produce adequate quantities of seed from open-pollinated orchards, as long as certain
conditions are met. Selection of a site where the species will produce abundant seed is essential,
and at present can only be done by observing seed production of the species on a range of sites.
There are several documented examples in which eucalypt seed orchards have produced very
poor seed crops, often when the species is planted on sites favourable for growth within its nat-
ural range (Eldridge et al. 1993). When planted as an exotic, seed production may occasionally
be suppressed. Thus, at least one eucalyptus oil producer in Brazil purchases E. globulus seed
from Australia because of the species reluctance to seed locally, and E. smithii, too, is shy to seed
in Swaziland ( J. Coppen pers. comm.). The use of bee-hives to encourage cross-pollination in
orchards, and therefore greater seed set, is recommended (Moncur 1991); multiple colonies are
better than one as they promote competition between bees.
The earlier an orchard flowers the sooner a breeder can move from the first to the second and
subsequent generations. Some species, such as E. nitens and E. regnans, cannot be relied upon to
flower until aged six or more years. Application of a growth regulator which stunts vegetative
growth but encourages abundant early flowering is a major breakthrough which speeds genetic
improvement of these and many other species (Reid et al. 1995).
Selection criteria and selection indices

The following selection criteria are pertinent to improving oil production in eucalypt species:
1 High leaf biomass, both as a sapling and when coppiced
2 High concentration of oil in the leaves
3 Good coppicing ability
4 Freedom from insect pests and diseases
5 Broad adaptability
6 High oil quality, that is, an oil that is attractive to the market.
The first five criteria are aimed at maximising the oil yield per hectare, while the sixth seeks
to produce an oil that is not only acceptable to the market but commands the best possible price.
This is a large number of traits to select for simultaneously. Genetic gain in individual traits
generally tends to diminish as the number of traits under selection increases. In an index
combining two, three, four and five traits, the gain in each trait will be about 70, 60, 50 and 45
per cent, respectively, of the gain expected under selection for a single character alone, assuming
traits are uncorrelated (Cotterill and Dean 1990). In practice, therefore, breeders must try to

minimise the number of traits under selection. In selection for oil production it may be suffi-
cient to select for stem sectional area (diameter), as this measure is often highly correlated with
biomass production and coppicing ability, and oil concentration, while setting limits for oil
quality (e.g. for medicinal, cineole-rich oils &70 per cent cineole, '1 per cent !-phellandrene).
The efficiency of selection may be improved by utilising a multi-trait selection index.
SmithHazel indices are often used and incorporate information on heritabilities, genetic cor-
relations and phenotypic correlations, but the calculations are complex (Cotterill and Dean
1990). If the key traits in the index are assumed to be uncorrelated, then simple indices such as
the primary index can work just as well for selection in first-generation breeding populations
and are far easier to calculate (Harwood and Aken 1997). A primary index incorporating the key
oil traits of stem sectional area and oil concentration might take the form:
Index value #w1h21 (PSA/SDSA) " w2h22 (POC/SDOC)
where w1 and w2 are the economic weights assigned to the two traits; h12 and h22 are the heritabil-
ities; PSA/SDSA is the individual (block adjusted) phenotypic value for stem sectional area nor-
malised by dividing it by the standard deviation of that trait; and POC/SDOC is the individual
(block adjusted) phenotypic value for oil concentration in the leaves, again normalised by
dividing it by the standard deviation of that trait.
Sampling and analytical considerations when selecting eucalypts for oil traits
To determine the extent of variation in oil traits due to genetic sources it is important to avoid
or minimise the confounding influence of non-genetic sources of variation. This is achieved by
use of appropriate sampling and analytical techniques. Failure to apply suitable methodological
and sampling controls is, unfortunately, a feature of many published studies of essential oils, ren-
dering them of dubious value. The following factors should be considered in any studies of inter-
or intra-specific variation in eucalyptus oil.
Variation due to ontogeny, age of plant and phenology

Eucalypts develop up to five distinct morphological types of leaf (viz., cotyledons, seedling
leaves, juvenile leaves, intermediate leaves and adult leaves) during their lifetime, each corres-
ponding to a certain ontogenetic stage in their development. Oil concentration in seedling
leaves is invariably much lower than that of the other stages, while the comparison between the
juvenile and intermediate phases and the adult are inconsistent and appear to depend largely on
species (Doran 1991). In some eucalypts (e.g. E. polybractea), the harvesting of coppice shoots
results in higher oil concentrations than are achieved from mature crowns (Brooker et al. 1988).
Oil composition may also change with ontogeny. Barton et al. (1991) found that juvenile leaves
from six-month-old seedlings of E. kochii grown in a glasshouse were lower in 1,8-cineole and
higher in terpene hydrocarbons, in comparison to their parents. Coppen and Jacovelli (1992)
studied oil yields and oil composition of juvenile and intermediate/adult leaves of a commercial
sixteen-month-old E. smithii seedling crop in Swaziland. In ten separate trees sampled, a consis-
tent pattern of decreasing oil yield in the leaf and decreasing cineole content of the oil was
obtained as one progressed up the tree.
The poor juvenilemature correlation in oil traits has already been discussed. To better ensure
the reliable ranking of a plants oil-production potential, sampling early ontogenetic stages,
including early coppice leaves, should be avoided. In progeny trials it is best to wait until plants
are at least three years of age before screening and ranking plants for oils.

Although there are no known reports of the effects of flowering on oil traits in eucalypts, evi-
dence from other genera suggests that oils traits are highly variable immediately before and dur-
ing flowering, so sampling during this period is probably best avoided.
Variation due to leaf age and position in the crown

Physiological leaf age is commonly denoted by the terms young leaf (growing tips), mature
leaf (mean age of about six months) and aged leaf (ca. 1218 months). The contrast in oil
concentration between young and mature leaves is often marked. Aged leaves generally yield less
oil than recently matured leaves. In E. camaldulensis, the concentration of 1,8-cineole increased
with increasing leaf age down the branch, reaching the highest levels in fully expanded, non-
lignified leaves 34 months of age. Thereafter, cineole concentration declined rapidly and reached
stable levels with leaf lignification (Doran and Bell 1994). Simmons and Parsons (1987) con-
cluded that the oil concentration at various stages of leaf maturity appears to be determined by a
complex pattern of quantitative change in individual or groups of compounds, some remaining
constant, some increasing and some decreasing with age. Patterns vary between individuals of
the one species on the one site and appear dependent on the genetic constitution of individuals.
Bryant (1950) drew attention to the largely unavoidable, but potentially confounding, influ-
ences of the position of the leaf on the tree and the influence of light intensity. Light has been
shown to be a key factor influencing oil production in a number of essential oil-producing taxa.
Several studies have found that the direction (aspect) faced by sampled branches and the sam-
pling height do not have a significant influence on oil concentration (e.g. Brooker et al. 1988,
Doran and Brophy 1990), although the findings of Coppen and Jacovelli (1992), noted above,
suggest that the age of the trees, or the particular species concerned, may be important.
When sampling leaves for genetic studies, therefore, it is important to limit these sources of
variation by attempting to collect only fully expanded and mature leaves of similar physiologi-
cal age across the entire progeny trial. As an added precaution, shaded parts of the canopy should
be avoided.
Seasonal variation
There is a relatively extensive literature on seasonal variation, no doubt because of the commer-
cial imperative of determining the harvest times that return the greatest yields of oil for a par-
ticular species. However, inappropriate sampling procedures which confound seasonal variation
with other key sources of variation, such as genotype, leaf age and ontogeny, are an unfortunate
feature of much of this literature.
A study of three eucalypt species (E. delegatensis, E. globulus and E. nitens) in which three
sources of variation (seasonal, leaf ageing and ontogenetic) were studied at regular intervals over
twelve months on labelled shoots of marked trees showed that (i) variation in oil concentration
and composition occurred during the active growing season only, (ii) oil concentration increased
steadily during the growing season and was at its maximum during autumn, when the propor-
tion of newly matured leaves was at its peak, and (iii) the oils of individual species and prove-
nances differed markedly in the patterns of change in proportions of different compounds
throughout the growing season (Haifeng Li 1993).
One generally consistent result from the studies undertaken to date is that genotypic differ-
ences outweigh any environmental effects on both oil composition and concentration.
Encouragingly for reliability of selection for oil concentration in E. camaldulensis, individuals
with high oil concentration in one season maintained their superiority over several seasons,

despite there being marked shifts in oil concentration over time (Doran and Bell 1994). These
authors concluded that, although the season of sampling appears to be of less importance to reli-
ability of rankings than factors such as leaf age, greater reproducibility of results can be attained
if fully matured leaves are sampled during the dormant or slower growing period of the year.
Techniques of oil extraction and chemical and statistical analysis
Oil extraction
Because of the large number of samples required for reliable estimates of genetic parameters,
some workers have replaced steam distillation, the conventional method of extracting volatile
oils from plants, by the speedier solvent extraction (Ammon et al. 1985b). Both methods have
advantages and disadvantages and both are costly in terms of labour and materials. It is advisable
to carry out some preliminary work to determine which is the best method for the particular
situation before embarking on a large-scale screening programme.
Whenever possible, the moisture content of the leaves being extracted should be determined
and oil yields reported on a moisture-free (or dry matter) basis. Only in this way can meaning-
ful comparisons be made between different samples, and samples analysed at different times and
by different workers. Leaves which are picked and distilled fresh can vary significantly in their
moisture content depending on the time of year, time between picking and distillation, condi-
tions of storage, etc., and oil yields reported on a fresh basis, particularly when determined by
steam distillation, can only be regarded as indicative. Azeotropic distillation of the water con-
tained in the leaves using a Dean and Stark apparatus is a simple, though time-consuming,
method for determining moisture content and preferable to oven drying, which may result in
loss of volatiles other than water. Ammon et al. (1985a) describe an alternative method, suitable
for use with their solvent extraction technique for Eucalyptus oil analysis (Ammon et al. 1985b).
Whatever method of oil extraction is employed, it should be appreciated that yields deter-
mined in the laboratory represent an exhaustive extraction. Yields likely to be obtained on
fresh leaf using similar material but in a large-scale, commercial context will inevitably be less
than these.
Chemical analysis
Essential oils are generally mixtures of terpenes, often quite complex. However, their relative
volatility means that they can be separated by a technique known as gas chromatography (GC).
GC is a standard analytical tool which, when optimised, not only separates the constituents of
the mixture but quantifies them as well. In competent hands it is very powerful, especially when
linked with other instrumental methods such as mass spectrometry (GC-MS). However, the
inexperienced investigator can encounter many problems leading to inaccurate results. Such
work is best done by a laboratory specialising in this technique and with experience in essential
oil analysis.
Statistical analysis
Quantitative genetic methods are appropriate for estimating genetic parameters of oil traits.
However, since classical methods of quantitative genetics assume that the frequency distribution
of a metric trait approximates the normal (Falconer 1989), their application to compositional
data is inappropriate when oil components are not independent and not normally distributed

(Birks and Kanowski 1988). Birks and Kanowski (1993) recommend analysis of log ratios
of proportional data (i.e. where constituents are reported in terms of relative abundance)
in order to remove the constraint of summation to unity and provide an interpretable
covariance structure, but this technique does not always overcome the problem of skewed distri-
butions which occur when a eucalypt has different chemical forms. The chemical form
contributing to the skewed distribution of the data may need to be identified and deleted from
the data set.
Case study: Eucalyptus camaldulensis

An outline of the breeding strategy proposed by Doran (1992) for improving oil production in
Petford E. camaldulensis is given below. In developing the strategy it was assumed that increased
wood production would be the principal breeding objective, with improvements in oil production
a secondary aim.
Improving growth traits

The starting point, therefore, is the main strategy directed at improving growth traits. For this,
a simple strategy, defined as recurrent selection for general combining ability with open pollina-
tion in a single population keeping maternal identity, was recommended. This strategy
combines the base, breeding and propagation populations in a single plantation on each site and
for each generation. These plantations serve sequentially as progeny tests of trees selected in the
previous generation, as a resource for selection and breeding for the next generation, and finally
as commercial seed orchards. They also provide estimates of genetic parameters (e.g. heritabilities,
genotype % environment interactions, ageage correlations) and may be used to identify mater-
ial to place in a vegetative propagation programme. Breeding strategies employing this basic
approach have been developed for Acacia, Casuarina, Eucalyptus, Melaleuca and Grevillea species in
many countries over the last decade (Harwood 1996) and very useful gains have been achieved.
For example, Eucalyptus grandis was bred using a similar strategy in Florida where, in four gen-
erations over some sixteen years, genetic gains of 159 per cent in stem volume production and a
substantial increase in cold tolerance were reported (Meskimen 1983, Eldridge et al. 1993). The
strategy is shown diagrammatically in Figure 4.7.
Improving oil traits

Controlled pollination, to establish an elite population for oil production and for vegetative
propagation, was recommended as a practical means of improving oil traits in parallel with the
main aim of improving growth traits.
By four years of age the main breeding population will have been gradually thinned down on
the basis of the key selection criteria of health, vigour and stem form. In the programme given
in Figure 4.7, which has many individual seedlots under test, we might expect the five best-
growing individuals of 350 of the original 400 open-pollinated families to be retained at
this stage (i.e. 1750 progenies). These trees would be screened individually for oil concentration
and the abundance of 1,8-cineole in their oil. The forty trees assessed as having the best general
combining ability (GCA) for oil traits would be crossed at the earliest opportunity following
selection using an assortative mating pattern. The controlled-pollinated families generated
would be raised in progeny tests and the best individuals in the best families selected by
combined index selection, giving oil traits and growth traits equal economic weight. These

Base Breeding Population Propagation Population Plantation Population
Population
main population elite population
open-pollinated progeny trials control-pollinated
progeny trials (cppt)
5 yrs
thin Seed
400 N. QLD seed
Generation 1 Orchard
Yr 0 1
40 clon
es by g
irdling
cutting
s
cp 5 7 yrs
20 20 clone trial 1
N. QLD
12 yrs 9 yrs
Generation 2 20 families thin Seed
100 300 seed
Yr 7 Orchard
2
cppt 8 yrs
1
cuttings
clone trial 2
20 20
N. QLD 15 yrs
Generation 3
Yr 13 100 90 200
cppt 14 yrs
2
20 20
Figure 4.7 Schematic diagram of the breeding strategy proposed for a tropical provenance (Petford) of
Eucalyptus camaldulensis. The strategy combines an open-pollinated breeding strategy for growth
traits with the establishment of an elite population by controlled pollination for improvement
of oil traits, together with clonal testing and deployment (adapted from Doran 1992 and
Eldridge 1995).
selections would then be available for mass vegetative propagation. The tendency of the nucleus
towards inbreeding would be reduced by including selections from new families in later genera-
tions of the main breeding population. In addition, the forty parents selected as the basis
for the elite population could be propagated vegetatively through girdling and collection of
cuttings from basal shoots (Kijkar 1991). As rooted cuttings, they would be established in
clonal tests. Selections that root readily and grow well might be used immediately for clonal
oil-producing plantations.
This strategy has a number of advantages over the alternative one of attempting to improve
oil traits in the main breeding population. Selection for oils is delayed until the fourth year,
when the initial thinning for growth traits in the main population has been completed. At this
stage the worst families have been removed and the poorest-growing individuals in the selected
families have also been culled (Figure 4.8). The costly chemical analytical work and selection for
oil traits is limited, therefore, to those families and individuals that have grown well to half rota-
tion age and produce large quantities of leaf biomass. Four years is also a sufficient age for trees
to express their mature oil characteristics and oil-yielding potential.
Climbing to pollinate the ortet at this age could be a problem as the trees will be quite tall
(ca. 12 m). Scaffolding could be erected around each tree to make the operation safer, or the
selected trees could be grafted to a clone bank to make pollination safer and easier. However, this
would add at least two years, and possibly three or four years, to the interval between genera-
tions (Eldridge 1995).

Figure 4.8 Seedling seed orchard of Eucalyptus camaldulensis at Ratchaburi, Thailand, 5.8 years from
planting and after the second thinning (photo: K. Pinyopusarerk).
Expected gain
The genetic gains per generation expected from mass selection to improve oil traits such as con-
centration and abundance of 1,8-cineole can be determined thus:
(G #ihi2)p
where i is the standardised selection differential and )p is the phenotypic standard deviation.1
One of the main advantages of the elite population strategy for improvement of oils over that
of trying to breed for these traits in the main breeding population is that favourable genetic
parameters for these characters can be harnessed to give a high rate of gain. The case study given
above may be used as an example. The forty trees with the best 1,8-cineole yields in the leaves
were selected from the 1750 trees remaining in the main population after first thinning. If
these selections were to be simply interbred in a conventional clonal seed orchard using open
pollination, it would lead to a production plantation with 39 per cent more 1,8-cineole in its
leaves. This estimate is based on the genetic parameters and phenotypic standard deviation for
this trait in trials in Zimbabwe reported by Doran and Matheson (1994).
The elite population strategy of assortative crossing of best (GCA) mates and testing in prog-
eny tests, however, can be confidently predicted to lead to clones of an oil-yielding capacity far
greater than that of their parents. For example, Doran (1992) reported on the progeny of a high
oil-yielding controlled cross in a field trial in Queensland, Australia, which had rapid height
1 Note that this formula applies only to mass selection (i.e. selection among individual trees) without reference to
pedigree (i.e. selection within and between families).

growth in combination with 1,8-cineole yields consistently above 4 per cent (w/w, dry matter
basis). This was 55 per cent greater than the mid-parent value and about double the oil concen-
tration of average trees. The use of selections like this in clonal plantations of this species would
improve oil yields dramatically.
The relatively simple strategy described above suits the circumstances in countries such as
Thailand, where there is a major breeding programme of tropical provenances of E. camaldulensis
(Raymond 1991, Eldridge 1995). This is not to imply that this is the best or only strategy
available for use with this species. Each strategy must be tailored to suit the relevant circum-
stances, with due consideration to the available base material, the biological constraints of the
species being bred, and the human, physical and financial constraints on the programme.
Eldridge et al. (1993) provide examples of other strategies developed by breeders for the
improvement of wood production and some other traits (e.g. cold tolerance) in eucalypts.
Acknowledgements
I would like to thank my colleagues, Alan Brown, Chris Harwood, Carolyn Raymond, Emlyn
Williams and Roger Arnold, for providing helpful comments during the development of this
chapter. Kron Aken, Maurice McDonald and Sarah Doran assisted with the Figures.
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5 Eucalyptus chemistry
Joseph J. Brophy and Ian A. Southwell
Introduction
The medicinal and aromatic properties of Eucalyptus are normally associated with the steam-
volatile components, and so this chapter, with the exception of the last section, is devoted to the
chemistry of the essential (or volatile) oils. This then generally restricts discussion to molecules
of molecular weight less than 250 amu, which are either terpenoid or aromatic in structure. The
ease with which volatile oils can be analysed using gas chromatography (GC) and GC coupled
techniques has meant that many investigations have been undertaken and the structures of
numerous constituents elucidated. Consequently, the number of volatile compounds reported
from Eucalyptus far exceeds the number of non-volatile ones. The leaves are the most frequently
investigated part of the plant but interesting constituents have also been isolated from the bark
and the wood.
Brophy has investigated many new Eucalyptus species using GC-MS techniques (see below)
and the results, together with a listing of the major components from these and previous studies
of eucalyptus oils, have been published in book form (Boland et al. 1991).
The bulk of the present chapter comprises a revised and up-dated list of those Eucalyptus
species for which the volatile oil has been analysed, showing oil yields and the identity and rela-
tive abundance of the most significant constituents (Table 5.2). The data for this table, as earlier
(Boland et al. 1991), are taken mostly from Australian sources, representing trees growing in
their natural habitat. Although some non-Australian data are included, these are usually so
similar to the analyses of endemic populations that the wider inclusion of such data is considered
unnecessary. A few species which do not occur in Australia (e.g. E. leizhou No. 1, a natural hybrid
which is used as a source of oil in China, and E. urophylla) are included in the table. Coppen and
Dyer (1993) have published an extensive bibliography of Eucalyptus and its leaf oils, indexed by
species and country and covering the literature from the 1920s to late 1992, which includes
exotic eucalypts.
The taxonomy of such a large and complex genus as Eucalyptus is under continual revision. For
example, the frequently distilled lemon-scented gum, E. citriodora, along with many other
species previously placed in the Eucalyptus genus, has recently been renamed as a member of the
Corymbia genus (Hill and Johnson 1995). For the purposes of this chapter, however, this species
will still be considered under Eucalyptus. At the latest count there were 777 species listed
(Wilcox 1997).
Early investigations
Although the first reported eucalyptus oil distillation is thought to be that of the Sydney
Peppermint, E. piperita, in 1788, regular steam distillations were not frequent until the 1850s,

when Bosisto in Victoria, Australia, produced firstly experimental and then commercial quanti-
ties of eucalyptus oil for the European market (Penfold 1935, Penfold and Morrison 1950,
McKern 1967, 1968). At that time, organic chemistry was only an emerging science and it was
not until later the same century that the principal constituent of E. globulus oil was named
eucalyptol and its structure established as 1,8-cineole (see later, Figure 5.2, structure 1)
(Boland et al. 1991). Baker and Smith then systematically investigated oils from other Eucalyptus
species, isolating some forty different compounds (Baker and Smith 1920, McKern 1968).
Several schools of essential oil research were established in New South Wales, Queensland, and
South and Western Australia, all publishing data on Eucalyptus oils and the chemical structures
of their constituents. Most of these results were included in Guenthers series of volumes on
essential oils (Guenther 1950) and, later, in Penfold and Williss treatise The Eucalypts (Penfold
and Willis 1961).
The advent of gas chromatography and, more recently, techniques coupling gas chromato-
graphy with mass spectrometry (GC-MS) and infrared spectroscopy (GC-IR), rapidly accelerated
the analysis of volatile oils and the identification of their constituents and this has given rise to
an extensive literature on the oils of Eucalyptus. Today, this literature continues to grow.
Sample preparation and analytical techniques
Sample preparation
As a guide to the commercial viability of production of any eucalyptus oil, laboratory distilla-
tions must first be performed to determine yields and chemical composition. Oil yields, usually
expressed as a percentage of the leaf weight, are measured on either a dry or fresh weight basis.1
The highest oil yield recorded in the authors laboratories was 12.75 per cent from the partly
dried leaf of E. dives. The equipment of choice for laboratory scale distillation is the Clevenger
apparatus (Clevenger 1928) or a modification of it (e.g. Hughes 1970, Whish 1996).
The distillation process is the most time-consuming step in the assessment of essential oil
quality. Consequently micro-extraction methods using a suitable organic solvent are frequently
used to determine oil yield and quality, especially where large numbers of samples are involved
(Ammon et al. 1985, Southwell and Stiff 1989, Brophy et al. 1989). A room temperature extrac-
tion time of 3040 h can be reduced to one hour if microwave irradiation is first carried out
(Southwell et al. 1995). Although the product is not as clean as the steam-distilled oil, the
extract accurately reflects leaf quality and, with the addition of an internal standard, can also
give a reliable estimate of selected constituents of the oil. The use of a GC vial insert (0.1 ml)
means that this method can be adapted to micro-analyses (Brophy et al. 1989, Chen and Spiro
1995, Spiro and Chen 1995). Consequently this is the method of choice for many laboratories
(including our own) for the screening of essential oil-bearing plants, including Eucalyptus.
Soxhlet extractions are also used for Eucalyptus analysis, as well as simultaneous distillation-
extraction procedures like those adapted to the LikensNickerson apparatus (Schultz et al.
1977). The principles of general essential oil preparation reviewed by researchers such as
Koedam (1987) are most applicable to Eucalyptus leaf analysis.
1 If possible, the moisture content of the distilled leaf should be determined so that oil yields can be expressed on a dry
weight basis. This then enables all yields that are determined to be compared on an equal basis. The moisture content
of fresh leaf may be as high as 70 per cent but declines rapidly after harvesting. However, even leaf which has been cut
and air-dried has a residual moisture content (around 5 per cent) and should not be assumed to be perfectly dry.

Although more recent techniques, including supercritical fluid extraction (Boelens and
Boelens 1997), microwave extraction (Craveiro et al. 1989) and headspace analysis (Chialva and
Gabri 1987) have been used to analyse plant volatiles, Eucalyptus has not received the same atten-
tion as other species. There is one report of the supercritical fluid extraction of Eucalyptus (Milner
et al. 1997). Other methods of isolation include vacuum distillation and this has been the
method of choice in a series of papers by Bignell et al. (19941998) who report on the oils
obtained from almost 200 species of Eucalyptus. The procedure has the advantage that it does not
lead to the production of artifacts or the degradation of some of the constituents of the oil which
can happen with conventional steam distillation, that is, the composition thus determined is
closer to the intrinsic composition of the oil within the leaves than that obtained via steam dis-
tillation. However, by the same token, the composition may not reflect what is obtained in prac-
tice (or could be expected) commercially. Moreover, the results reported by Bignell et al. are
derived from single trees and may not be representative either of the particular population of
which the tree is part or of the wider distribution of the species. Nevertheless, they are reported
here (Table 5.2) because in a significant number of cases they are the only analyses reported for
the particular Eucalyptus species.
Analytical techniques
Before the advent of gas chromatography most essential oils were analysed by measuring optical
rotation, relative density, refractive index and solubility in alcohol. Bench chemistry methods
were also used to determine acid value, ester value (before and after esterification), carbonyl
value, phenol content and the concentration of some specific isolates (e.g. 1,8-cineole). These
methods still have a place today in monographs published by standards organisations such as the
International Standardization Organization (ISO) and pharmacopoeias such as the British
Pharmacopoeia (BP). With cineole-type eucalyptus oils, the o-cresol method of Cocking (1920,
1927) is still used as the bench chemistry method for the determination of cineole. Further
information on eucalyptus oil standards is given in Appendix 5; details of how and where the
standards can be obtained are given in Appendix 7.
In the main, the identification of individual eucalyptus oil constituents used to be dependent
on the isolation of pure compounds, either by fractional distillation under vacuum or using
alumina or silica column chromatography. This was then followed by derivatisation and mixed
melting point comparison with an authentic derivative of the suspected compound. With
modern chromatographic, spectroscopic and X-ray crystallographic techniques, identifications
previously taking months or years can now be achieved in hours or days. Examples illustrating
the use of these techniques in identifying Eucalyptus constituents are abundant in the literature
(e.g. Boland et al. 1992, Ghisalberti et al. 1995, Singh and Etoh 1995). ISO standards now
include a chromatographic profile and typical gas chromatographic trace in addition to physico-
chemical and other data.
The most commonly used technique for the identification of volatile constituents is gas
chromatography-mass spectrometry (GC-MS). Using GC-MS a mass spectrum can be obtained
for each peak from a chromatogram and compared with a library of reference spectra in order to
obtain a spectrum of best fit. The spectra of the common terpenes are in most spectral libraries
(e.g. Adams 1995) and a collection of !-triketone mass spectra has recently been published
(Brophy et al. 1996). Mass spectral data alone are insufficient for unambiguous identification,
especially for terpenoids with similar spectra, and should be supported by retention index mea-
surements on two columns of different polarity (Stevens 1996) or additional information (IR,
NMR, etc., e.g. Liener 1996). The use of gas chromatography-infrared spectroscopy (GC-IR) is

one way of providing such data. The critical factor in all GC techniques is the resolution
obtained by the chromatographic column. For example, 1,8-cineole often co-elutes with
limonene on non-polar columns and with !-phellandrene on polar columns. Columns of inter-
mediate polarity often give superior resolution of these key Eucalyptus constituents (Brophy et al.
1989).
Advances in computer technology and software development have encouraged the use of
multivariate statistical methods for principal component and cluster analysis of constituents
(e.g. Brooker and Lassak 1981, Silvestre et al. 1997).
Infraspecific variation and chemotaxonomy

Early investigations of eucalyptus oils suggested that the composition of an oil was constant
within the same species (Baker and Smith 1920) and new taxa were sometimes established solely
on chemical evidence (McKern 1968). It was later realised, however, that infraspecific variation
could occur. Among many examples are the piperitone and cineole/eudesmol forms of E. piperita
(McKern 1968) and the piperitone/phellandrene, phellandrene, piperitone/cineole and cineole
forms of E. dives (Penfold and Morrison 1927a, 1929, Hellyer et al. 1969).
The recognition of infraspecific variation led to the introduction of terms such as physiologi-
cal form or chemical variety and the different types were designated Type, Variety A,
Variety B, Variety C, etc., in order of their discovery (Hellyer et al. 1969). More modern
terminology regards these as chemotypes or chemovars. In the case of E. punctata, however,
sampling seventy-one individual trees showed a wide but continuous variation in the concentra-
tion of the major oil components, indicating that there are no grounds for the establishment of
separate chemical types (Southwell 1973). This infraspecific variation in oil composition high-
lights the importance of investigating individual trees and not assuming that the results from
single trees are representative of the species generally (Boland et al. 1991).
Correlations between the constituents of Eucalyptus species and their taxonomic relationship,
both within the genus and as part of the Myrtaceae family, have been attempted. Hegnauer, for
example, has addressed the issue in his Chemotaxonomie der Pflanzen series (Hegnauer 1969,
1990).
With such a large number of species within the eucalypts, it is not surprising that attempts
have been made to split the genus Eucalyptus into smaller genera. The latest work in this area, by
Hill and Johnson (1995), has seen Corymbia, previously a sub-genus, raised to full genus status,
with approximately 110 species within it. The remaining 700 species (approximately) still
belong to the genus Eucalyptus, though within this genus there are major and minor groupings.
These are shown in the phylogram (Figure 5.1) adapted from Hill and Johnson (1995).
An attempt to discern trends in the essential oils of species within the major groups was car-
ried out by Boland and Brophy (1993) based on analyses of the essential oils of approximately
one third of the species. While not conclusive, some trends were observed. Corymbia as a genus
generally produces poor oil yields and low 1,8-cineole percentages (Boland and Brophy 1993,
Brophy et al. 1998b). An exception, however, is C. citriodora (Eucalyptus citriodora) which can pro-
duce up to 4.2 per cent of a citronellal-rich ("80 per cent) oil. Significantly more species have
now been analysed and the question will be re-examined.
Within the Monocalyptus is a large group of species comprising the majority of section
Renantheria which contain significant amounts of cis- and trans-menth-2-en-1-ol and cis- and
trans-piperitol, as well as, in a significant number of species, piperitone. E. radiata and E. oblonga
occur in this group. Within the eucalypts this is the only place that this occurs. There is also a
group of species which contain oils composed principally of !-triketone (e.g. 26, Figure 5.3)

Arillastrum Group (4 genera / 5 species)
Angophora (17)
Corymbia Fundoria (1)

Corymbia Apteria (1)
Corymbia Rufaria (67)
Corymbia Ochraria (17)
Corymbia Blakearia (27)
Odontocalyptus
Eudesmia s. str.
Fibridia
(20+)
Leprolaena Baileyanae
Leprolaena Miniatae
Gaubaea (2)
Idiogenes (1)
Monocalyptus (170)
Symphyomyrtus (500+)
Telocalyptus (4)
Nothocalyptus (1)
Figure 5.1 Phylogram of the eucalypts (after Hill and Johnson 1995). Numbers in parentheses refer to the
number of species.
and acylphloroglucinol (e.g. 22 and 27, Figure 5.3) derivatives (Brophy et al. 1996) in this sec-
tion, an occurrence not found in the rest of the eucalypts.
Symphyomyrtus is the largest group within the eucalypts, containing over 500 species.
Within it there are groups of species with high oil yields and 1,8-cineole as the major
component. E. bakeri and E. kochii belong to one section of this group, E. camaldulensis to a
second, E. sparsa and E. polybractea to a third, and E. globulus, E. sturgissiana and E. smithii to a
fourth.
It was thought (Boland and Brophy 1993) that Western Australian species produced more
aromatic compounds than did their eastern Australian relatives, this phenomenon crossing
group boundaries. More recent work, however, published in a series of papers by Bignell et al.
(in which the oil is produced by vacuum distillation rather than steam distillation) has shown
that aromatic compounds are present in most of the species examined.
Commercial utilisation of eucalyptus oils
Cineole-rich oils
Apart from practical considerations such as oil and biomass yields, and the amenability of the
species to appropriate and economic field management, the most important factor in determining

Cineole-rich oils
7
1
6 2
5 3
O
4
OH
8 (+)--pinene 4
9 10
1,8-cineole 1 ()-limonene 2 (+)--terpineol 3
OH
H H
H H
(+)-aromadendrene 5 ()-globulol 6
Lemon-scented/perfumery oils
CHO CH2OAc
CHO CHO
(+)-citronellal 7 neral 8 geranial 9 geranyl acetate 10
Piperitone/phellandrene-rich oils E. olida
COOMe
()-piperitone 11 ()--phellandrene 12 E-methyl cinnamate 13
Figure 5.2 Chemical structures of some common constituents of commercial eucalyptus oils.

the commercial value of an oil is its chemical composition. Of the large and diverse range of
compounds found in eucalyptus oils (Table 5.2), the most important is the monoterpene ether
1,8-cineole (1, Figure 5.2). It is used for medicinal, flavour and fragrance purposes and has sig-
nificant biological activity (e.g. mosquito repellency (Klocke et al. 1987)). It comprises over 90
per cent of the oil in some specimens of E. bakeri (Brophy and Boland 1989), E. kochii (Gardner
and Watson 1947/48), E. oblonga (Baker and Smith 1920), E. plenissima (Brooker et al. 1988),
E. polybractea (Boland et al. 1991), E. sparsa (Brophy and Lassak 1986, Southwell 1987) and
E. sturgissiana (Boland et al. 1991). With the exception of E. polybractea, few of these are being
exploited as commercial sources of 1,8-cineole.
E. globulus remains the chief source of cineole worldwide although the oil contains a lower
proportion of it than E. polybractea and some other species. However, E. globulus is widely grown
for its wood and for pulp production and, as a result, the waste leaf is available for production
of oil. This and other commercially produced oils with concentrations of cineole less than that
in E. polybractea (e.g. E. smithii and E. radiata) are either fractionated to enhance cineole levels
to the 7075 per cent or 8085 per cent required by monographs published by ISO and
various national pharmacopoeias or sold for uses where cineole content is not so critical
(e.g. aromatherapy).
The most common constituents co-occurring with 1,8-cineole are limonene (2) and
#-terpineol (3), both of which can be derived from the menth-1-en-8-yl cation, the same
biogenetic precursor from which cineole is thought to be derived (Croteau 1987, Croteau et al.
1994). Other biogenetic pathways then contribute the other monoterpenes, for example,
#-pinene (4), sesquiterpenes such as aromadendrene (5), globulol (6) and #- , !- and $-eudesmol
(1719, Figure 5.3), and aromatic constituents, for example, methyl cinnamate (13).
Other commercial oils

Although cineole-type (medicinal) eucalyptus oils dominate world production (estimated
by Coppen and Hone (1992) at between 2500 and 3100 t in 1991, and by Lawrence (1993)
at 3700 t), lemon-scented (perfumery) oils are also produced. The worldwide production
of citronellal (7) oils from E. citriodora and the citral (i.e. neral%geranial, 8, 9) oils from
E. staigeriana was estimated at 320 and 70 t respectively for 1984 (Lawrence 1985). A chemotype
of E. citriodora rich in citronellol (16, Figure 5.3) also exists (Penfold et al. 1951). Geranyl
acetate (10) has been produced in the past from the leaf and bark of E. macarthurii and
used as a fragrance constituent (Lassak 1988) although it is not believed to be in current
production.
There has been a smaller market for piperitone (11) and #-phellandrene (12)-rich oils (e.g.
E. dives Type). Piperitone has been used in the synthesis of menthol for flavouring and phellan-
drene as a fragrance.
The most recent example of a new eucalyptus oil product is that of E-methyl cinnamate (13)
from E. olida. This natural flavouring ingredient was discovered in near pure form in high yield
for the first time in E. olida in 1985 (Curtis et al. 1990) and its production has subsequently been
commercialised in Australia, from where it is exported.
Oils of potential commercial use

Many other eucalyptus oils have the potential to serve as sources of chemical isolates, that is,
they contain chemicals with potential commercial application (Figure 5.3).

CHO
MeO O
CH2OH
OH O
agglomerone 14 benzaldehyde 15 citronellol 16
OH OH OH
-eudesmol 17 -eudesmol 18 -eudesmol 19
COOMe
CHO
HO OH
MeO OMe
OHC
OH CHO OMe
OH O
guaiol 20 iso-bicyclogermacral 21 jensenone 22 methyl eudesmate 23
H
MeO OMe
MeO O
PhCH2CH2OCOCH2Ph
.
-phenylethyl O
OH O OMe
phenylacetate 24 OH
spathulenol 25 tasmanone 26 torquatone 27
Figure 5.3 Chemical structures of some constituents with the potential to be sourced as isolates from euca-
lyptus oils not yet in commercial production.
Food flavour companies have expressed interest in !-phenylethyl phenylacetate (24) which is
sometimes the major component of the leaf and bark oil of E. crenulata (Lassak and Southwell
1969, Boland et al. 1991) and the leaf oil of E. aggregata (Hellyer et al. 1966, Boland et al. 1991).
The leaf oil of E. crenulata is also rich in methyl eudesmate (methyl 3,4,5-trimethoxybenzoate,
23). Oils from other species of Eucalyptus provide excellent sources of the eudesmols (1719), the
ketones agglomerone (14), jensenone (22), tasmanone (26) and torquatone (27), isobicyclo-
germacral (21), spathulenol (25), benzaldehyde (15) and many other isolates. The best Eucalyptus
sources of chemicals 14 27 are shown in Table 5.1.

Table 5.1 Constituents with the potential to be sourced as chemical isolates from Eucalyptus leaf oils not
yet in commercial production
Isolate a Species Oil yield b Isolate in Reference

(%) oil (%)
Agglomerone (14) E. agglomerata 0.9 80 Hellyer (1964, 1968)

Benzaldehyde (15) E. yarraensis 0.1 90 Lassak and Southwell (1977)
Citronellol (16) E. citriodora 3.4 85 Penfold et al. (1951)
Eudesmols (1719) E. oblonga 0.7 97 Hellyer and McKern (1963)
Guaiol (20) E. maculata 1.1 40 Lassak and Southwell (1977)
Isobicyclogermacral (21) E. dawsonii 3.2 44 Boland et al. (1991)
Jensenone (22) E. jensenii 0.3 70 Boland et al. (1992)
Methyl eudesmate (23) E. crenulata 0.7 47 Hellyer et al. (1964)
!-Phenylethyl E. aggregata 1.5 91 Hellyer et al. (1966)
phenylacetate (24)
Spathulenol (25) E. rubida 1.1 36 Boland et al. (1991)
Tasmanone (26) E. cloeziana 1.9 96 Boland et al. (1991)
Torquatone (27) E. caesia 0.9 50 Bowyer and Jefferies (1959)
a Figures in parentheses refer to chemical structures (Figure 5.3).

b Fresh weight basis except for E. dawsonii and E. rubida (dry weight).
The commercial development of an oil need not be dependent on the major constituents. For
example, the grandinol-type !-triketones from E. grandis possess powerful root and photosyn-
thetic electron transport inhibition properties (Crow et al. 1971, 1976, Yoshida et al. 1988,
Yoneyama et al. 1989) and the minor constituents of E. citriodora and E. camaldulensis oils have
been investigated for mosquito repellent activity (Nishimura et al. 1986, Nishimura 1987,
Watanabe et al. 1993).
Biogenesis of eucalyptus oil constituents

The formation of the mono- and sesquiterpenoids in Eucalyptus follows the general principles of
isoprenoid biosynthesis (Erman 1985, Croteau 1987). The finer details of these principles
advance as the frequency and complexity of labelling experiments increases. For example, recent
investigations now suggest that in higher plants isopentenyl pyrophosphate is formed not from
mevalonic acid but via the alternative triose phosphate/pyruvate pathway (Lichtenthaler et al.
1997, Eisenreich et al. 1997). These early stages of isoprenoid biosynthesis seem to have been
more often studied than the finer details of the coupling and cyclisation steps to form mono-
terpene, sesquiterpene, diterpene and sesterterpene end products.
The Croteau group, working principally on the monoterpenoids, has isolated cyclases and
studied many reactions using isotope labelling and inhibition techniques, principally in mint,
pine, marjoram, sage and fennel. From this picture, an extension and refinement of Ruzickas
original Biogenetic Isoprene Rule regarding the head-to-tail coupling of isoprene units has
developed (Arigoni et al. 1993). Although specific studies on Eucalyptus are rare, principles relat-
ing to these other species can be applied to the formation of eucalyptus oil terpenoids. For exam-
ple, the isolation of cineole synthase from sage (Salvia officinalis) led Croteau et al. (1994) to
propose alternative stereochemical routes to 1,8-cineole (Figure 5.4) that should also be relevant
for Eucalyptus.
The non-terpenoids in eucalyptus oils are probably derived via the shikimic acid or
phenylalaninecinnamic acid routes (e.g. methyl eudesmate (23), methyl cinnamate (13),

3 10
4
OPP OPP PPO
5 2 1* * PPO
9
6
* 7 8
*
()3RLPP
(+)3SLPP
+ OPP PPO +
OPP * * PPO
* *
1
OPP PPO
+ +
* *
2 2
* H 2O * * H2O *
OH HO
+ +
3 3

(+)4R
()4S
Terpineol Terpineol
* *
1,8Cineole
Figure 5.4 Alternative stereochemical routes from geranyl pyrophosphate to 1,8-cineole. LPP is
linalyl pyrophosphate; OPP is the pyrophosphate moiety. Asterisks indicate the two possi-
ble positions of labelling from [1-3H]geranyl pyrophosphate (from Croteau et al. 1994;
used with permission from Academic Press and the author).
!-phenylethyl phenylacetate (24)). However, much more research needs to be done on the for-
mation of the oil components in Eucalyptus.
Metabolism
The bioactivity and chemical ecology of eucalyptus oil are dealt with in detail in other chapters
of this book. Some aspects of the chemistry of metabolites are reviewed here.
The metabolism of eucalyptus oil constituents in humans has been poorly studied.
Uroterpenol (menth-1-en-7,8-diol) has been isolated from human urine (Wade et al. 1966),

presumably as a metabolite of dietary limonene which is also a common eucalyptus oil con-
stituent. A review published in 1984 (Santhanakrishnan) on Biohydroxylation of Terpenes in
Mammals only reported studies with dogs, rabbits and marsupials (the koala and possum
(Southwell et al. 1980)). Terpene metabolism generally involved hydroxylation and further oxi-
dation through to the carboxylic acid where primary carbon atoms were involved.
Marsupials, such as the koala, possum and glider, can survive almost exclusively on a diet of
Eucalyptus leaves and consequently can ingest large amounts (1 g/kg) of eucalyptus oil (Eberhard
et al. 1975, Foley et al. 1987, McLean et al. 1993). The concurrent excretion of large amounts of
glucuronic acid implies excretion as glucuronide ethers or esters although isolation of these con-
jugates was not reported (Southwell 1975, Southwell et al. 1980).
Metabolites of 1,8-cineole have been investigated from a number of species, ranging from
microorganisms through insects to possums, rabbits and rats. Hydroxylation can occur at most
carbon atoms but microorganisms, insects, rabbits and rats favour oxidation of the ring, while
marsupials favour oxidation of the exposed gem-dimethyl group (Flynn and Southwell 1979,
Southwell et al. 1995). On occasions the hydroxyl groups are oxidised through to ring carbon
ketones or to terminal carboxylic acid groups. Insect species feeding on 1,8-cineole-rich leaves
metabolise the moiety differently, suggesting a possible insect communication role for the
metabolites.
Non-volatile constituents
The chemistry of the volatile oils is only one facet of Eucalyptus secondary metabolite
chemistry (Dayal 1988). The genus also contains flavonoids, triterpenes, long chain ketones,
glycosides, acylphloroglucinol derivatives and adducts combining more than one of these
chemical entities. Typical examples are shown in Figure 5.5, some of which are reviewed in more
detail in Chapter 12.
Illustrative of the variety of compounds which occur in Eucalyptus are those found in the
leaf waxes. These include flavonoids such as eucalyptin (5-hydroxy-7,4&-dimethoxy-6,8-
dimethylflavone) (28) (Lamberton 1964, Courtney et al. 1983), triterpenes such as ursolic acid
(29) (Courtney et al. 1983), long-chain ketones such as tritriacontane-16,18-dione (Horn et al.
1964) and its 4-hydroxy equivalent (30), a natural antioxidant (Osawa and Namiki 1985), and
ketones such as 4,6-dimethoxy-2-hydroxyacetophenone (Courtney et al. 1983). None of these is
known to be in commercial production from Eucalyptus.
On the other hand, the flavone-glycoside rutin (31), (3,5,7,3&,4&-pentahydroxy flavone-3-
rhamnoglucoside), which occurs in concentrations of 13 per cent and 23 per cent (dried leaf) in
E. macrorhyncha and E. youmanii, respectively, has been produced for medical applications for
many years (McKern 1960). Occasional export of dried leaf for such purposes still occurs from
Australia (Goodwin pers. comm. 1996).
Ghisalberti (1996), in reviewing bioactive acylphloroglucinol derivatives from Eucalyptus,
updates and extends an earlier review on volatile !-triketones (Hellyer 1968). Singh et al. (1999)
have also reviewed non-volatile constituents of eucalypts. Recent investigations have reported
new and known triterpenes from E. globulus wood (Santos et al. 1997) and E. camaldulensis leaf
(Begum et al. 1997, Siddiqui et al. 1997). These include unusual cinnamic acid esters of
oleanolates (32) and ursolates. In addition, unusual couplings of a jensenone-type acylphloroglu-
cinol to pinane, aromadendrane, guaiane (to give e.g. macrocarpal D, 33) or eudesmane
terpenoids give adducts with promising bioactivity (Aukrust and Skattebol 1996, Savina et al.
1991, Takasaki et al. 1994, Singh and Etoh 1995, Osawa et al. 1996, Singh et al. 1996).

OMe
COOH
MeO O
HO
OH O
eucalyptin 28 ursolic acid 29
OH
OH
O O OH HO O
C15H31 (CH2)11
O[6-(-L-rhamnosyl)
4-hydroxytritriacontane-16,18-dione 30 OH O -D-glucose]
rutin 31
OH
COOMe OHC
HO OH
OH
O CHO
O cis-p -methoxycinnamoyloxyoleanolic macrocarpal D 33

acid methyl ester 32
OMe
Figure 5.5 Chemical structures of some non-volatile Eucalyptus constituents.

Table 5.2 Oil yields and characteristic constituents of the essential oils of Eucalyptus species
Species Oil yield a Characteristic constituents b Reference

(%)
E. abergiana 0.3 dry #-pinene (57), !-pinene Brophy unpubl.

(4), globulol (13)
E. absita trc aromadendrene (8), Bignell et al. (1995c)
torquatone (25)
E. acaciiformis 0.2 d-#-pinene, geranyl acetate (?), Baker and Smith
sesquiterpenes (1920)
1.01.4 1,8-cineole (66), p-cymene, Boland et al. (1991)
#-terpineol, globulol,
viridiflorol
E. accedens 0.9 d-#-pinene, 1,8-cineole, eudesmol Baker and Smith
(mixture of isomers) (1920)
0.9 dry 1,8-cineole (54), aromadendrene Bignell et al. (1997g)
(8), trans-pinocarveol (15)
E. acies 0.2 dry 1,8-cineole (34), linalool (16), Bignell et al. (1997b)
#-terpineol (15)
E. acmenoides 0.1 #-pinene, phellandrene, Baker and Smith
1,8-cineole, sesquiterpenes (1920)
0.91.0 #-pinene (44), 1,8-cineole (43) Boland et al. (1991)
E. acroleuca 0.71.2 dry #-pinene (57), 1,8-cineole (42), Brophy unpubl.
#-terpineol (6)
E. aequioperta 1.1 dry #-pinene (10), 1,8-cineole (36), Bignell et al. (1997e)
bicyclogermacrene (12)
E. agglomerata 0.91.4 agglomerone Unpubl. (1961),
Hellyer (1964)
0.2 dry tasmanone (8), agglomerone (3), Bignell et al. (1998)
spathulenol (6)
0.40.6 tasmanone, agglomerone, aromatic Brophy unpubl.
compounds
E. aggregata tr-0.3 d-#-pinene, limonene, 1,8-cineole, Baker and Smith
(syn. E. rydalensis) p-cymene, methyl eudesmate, (1920), Hellyer
!-phenylethyl phenylacetate, et al. (1966)
sesquiterpenes
0.61.5 isoamyl phenylacetate, Boland et al. (1991)
!-phenylethyl
phenylacetate (91)
E. albens 0.1 #-pinene, 1,8-cineole, p-cymene Baker and Smith (1920)
tr globulol (4), spathulenol (8), #- , Bignell et al. (1997f )
!- , $-eudesmol (6 total)
E. albida 0.4 dry #-pinene (7), !-pinene (10), Bignell et al. (1997d)
bicyclogermacrene (20), #- , !- ,
$-eudesmol (10 total)
E. alpina 0.4 #-pinene, 1,8-cineole Baker and Smith
(1920)
E. amplifolia 0.91.2 #-pinene, dl-limonene, 1,8-cineole, Hellyer and McKern
aromadendrene, #-terpineol, (1966)
#-eudesmol, !-eudesmol
0.4 dry 1,8-cineole (24), aromadendrene Bignell et al. (1996a)
(24), globulol (6)
E. amygdalina 1.62.3 1,8-cineole Baker and Smith
(syn. E. salicifolia) (1920)
1.0 #-pinene, 1,8-cineole (70), trans- Ahmadouch et al.
pinocarveol, #-terpineol, terpinyl (1985)
acetate

Table 5.2 (Continued)

(%)
2.56.3 dry #-phellandrene (16), 1,8-cineole (15), Li et al. (1995)

p-cymene (8), cis- and trans-menth-
2-en-1-ol (8 total), piperitone (13)
0.2 terpinen-4-ol (4), piperitone (63), Brophy unpubl.
!-eudesmol (4)
E. andrewsii 1.6 #-pinene (4), limonene (13), Brophy unpubl.
1,8-cineole (62)
subsp. 1.3 l-#-phellandrene, p-cymene, Baker and Smith
andrewsii piperitone, piperitol (1920), Jones and
(probably trans-) White (1928)
0.6 limonene (4), 1,8-cineole (48), #-, Brophy unpubl.
!-, $-eudesmol (20 total)
subsp. 0.9 #-phellandrene, eudesmol (mixture Baker and Smith
campanulata of isomers) (1920), Jones and
(syn. White (1928)
E. campanulata)
0.6 p-cymene (23), menth-2-en-1-ols Brophy unpubl.
(13 total), #-, !-, $-eudesmol
(30 total)
E. angophoroides 0.2 pinene, l-#-phellandrene, Baker and Smith
1,8-cineole, sesquiterpenes (1920),
1.31.6 #-pinene, limonene, 1,8-cineole Boland et al. (1991)
(70), globulol
E. angulosa 0.91.2 d-#-pinene, 1,8-cineole, Baker and Smith
0.3 dry #-pinene (32), 1,8-cineole (14), Bignell et al. (1994a)
aromadendrene (11), #-, !-,
$-eudesmol (total 8)
E. angustissima 3.4 dry 1,8-cineole (76), #-terpineol (4) Bignell et al. (1997d)
E. annulata 1.5 dry #-pinene (36), 1,8-cineole (42), Bignell et al. (1996e)
aromadendrene (4)
E. annuliformis 5.5 dry #-pinene (23), 1,8-cineole (41), Bignell et al. (1994c)
!-eudesmol (6)
E. apiculata 0.8 d-#-pinene, 1,8-cineole, l-piperitone, Baker and Smith
E. apodophylla 0.10.2 #-pinene (37), limonene (31), Boland et al. (1991)
#-terpineol (6)
0.5 #-pinene (4), limonene (16), Menut et al. (1999)
apodophyllone (5), isotorquatone
(11), torquatone (11), jensenone (4)
E. approximans
subsp. 1.8 p-cymene, cis- and trans-p-menth-2- Lassak and Southwell
approximans en-1-ol, piperitone, cis- and trans- (1982)
piperitol
subsp. 2.1 #- and !-phellandrene, p-cymene, Lassak and Southwell
codonocarpa cis- and trans-p-menth-2-en-1-ol, (1982)
piperitone
E. aquilina 1.5 dry 1,8-cineole (59), #-terpineol (10), Bignell et al. (1997b)
1.4 1,8-cineole (60), #-terpineol (10), #-, Brophy unpubl.
E. arachnaea tr 1,8-cineole (11), aromadendrene (17), Bignell et al. (1997c)
trans-pinocarveol (8), globulol (8),
isobicyclogermacral (7)


(%)
E. archeri 2.12.5 dry #-pinene (19), limonene (4), Li et al. (1996)

1,8-cineole (60)
E. argophloia 0.6 #-pinene (65), limonene, isoamyl Boland et al. (1991)
isovalerate
E. argutifolia 0.9 dry #-pinene (15), 1,8-cineole (54), Bignell et al. (1995a)
!-eudesmol (5)
E. argyphea 0.3 dry #-pinene (15), 1,8-cineole (26), Bignell et al. (1997d)
trans-pinocarveol (8)
E. aromaphloia 1.54.4 isovaleraldehyde, #-pinene, Pryor and Willis
1,8-cineole (1954), Boland
et al. (1991)
E. aspratilis 1.5 dry #-pinene (19), 1,8-cineole (18), Bignell et al. (1996e)
$-terpinene (26)
E. astringens 0.50.6 dry #-pinene, 1,8-cineole, Marshall and Watson
aromadendrene (1937/38)
1.7 #-pinene (36), limonene, Holeman et al. (1987)
1,8-cineole (43), pinocarveol
2.9 dry #-pinene (13), p-cymene (18), Bignell et al. (1996e)
!-caryophyllene (15)
0.9 #-pinene (5), 1,8-cineole (57), Brophy unpubl.
E. aureola 0.40.8 #-pinene (71), guaiol (5), #-, !-, Brophy et al. (1998b)
E. badjensis 2.8 #-pinene, 1,8-cineole (70), Boland et al. (1991)
#-terpineol, #-, !-, $-eudesmol
E. baeuerlenii 0.4 #-pinene, 1,8-cineole, eudesmol Baker and Smith
1.02.6 dry limonene, 1,8-cineole (70), Boland et al. (1991)
E. baileyana 0.8 d-#-pinene, l-aromadendrene Baker and Smith
(1920)
E. bakeri 1.0 1,8-cineole, p-isopropylphenol, Penfold (1927)
phloracetophenone
2,4-dimethylether
1.83.0 1,8-cineole (90) Brophy and Boland
(1989)
2.5 dry !-phellandrene (2), 1,8-cineole Bignell et al. (1996b)
(80), p-cymene (4)
E. balanopelex 0.7 dry #-pinene (44), 1,8-cineole (28), Bignell et al. (1997d)
#-terpineol (4)
E. balladoniensis 0.3 dry #-pinene (10), aromadendrene Bignell et al. (1998)
subsp. sedens (11), #-, !-, $-eudesmol (42 total)
E. bancroftii 0.5 l-#-pinene, l-#-phellandrene, Baker and Smith
1,8-cineole (1920)
0.9 dry #-pinene (4), 1,8-cineole (77) Bignell et al. (1996a)
E. banksii 0.3 1,8-cineole Unpubl. (1961)
E. barberi 2.3 dry 1,8-cineole (72), #-terpineol (3), Li et al. (1996)
#-terpinyl acetate (8)
E. baueriana 0.3 #-phellandrene, 1,8-cineole, Baker and Smith
(syn. E. fletcheri) sesquiterpenes (1920)
1.23.3 dry #-pinene, 1,8-cineole (61), Boland et al. (1991)
#-terpineol, globulol


(%)
0.7 dry p-cymene (17), !-caryophyllene Bignell et al. (1997a)

(16), bicyclogermacrene (14),
spathulenol (22)
E. baxteri 0.3 dry 1,8-cineole (30), #-, !-, $-eudesmol Bignell et al. (1997b)
(33 total)
0.8 1,8-cineole (30), #-, !-, Brophy unpubl.
$-eudesmol (28 total), aromatic
compounds (12)
E. behriana 0.6 #-pinene, 1,8-cineole Baker and Smith
(1920)
0.81.1 dry 1,8-cineole, p-cymene, globulol, Boland et al. (1991)
!-eudesmol
0.5 dry 1,8-cineole (36), p-cymene (11), Bignell et al. (1995c)
!-eudesmol (25)
E. bensonii 2.5 agglomerone (72), tasmanone Brophy unpubl.
(15), #-, !-, $-eudesmol (5 total)
E. benthamii
var. benthamii 1.4 #-pinene (53), aromadendrene Boland et al. (1991)
(10), globulol (16)
var. dorrigoensis 1.11.2 #-pinene (5), 1,8-cineole (37), Boland et al. (1991)
p-cymene (10), aromadendrene,
E. beyeri globulol
cineole-rich 2.3 #-pinene, 1,8-cineole (65), globulol, Boland et al. (1991)
form #-, !-, $-eudesmol
eudesmol- 1.8 globulol (19), #-, !-, $-eudesmol Boland et al. (1991)
rich form (total 63)
E. blakelyi 2.1 #- and !-pinene, 1,8-cineole (60), Holeman et al. (1987)
p- cymene
1.1 dry limonene (3), 1,8-cineole (67), Bignell et al. (1996a)
p-cymene (3)
E. blaxlandii 0.8 d-#-pinene, 1,8-cineole Baker and Smith
(1920)
1.5 #-pinene (13), 1,8-cineole (11), #-, Brophy unpubl.
E. bleeseri 0.4 dry #-pinene (9), !-pinene (10), Bignell et al. (1997f )
E. bloxsomei 0.81.0 #-pinene (30), !-pinene (11), guaiol Brophy et al. (1998b)
(15), globulol (7)
E. bosistoana 1.0 pinene, 1,8-cineole, terpineol, Baker and Smith
sesquiterpenes, aldehydes (1920)
1.5 #-pinene (6), !-phellandrene (7), Holeman et al. (1987)
limonene (7), 1,8-cineole (60)
E. botryoides 0.1 d-#-pinene, sesquiterpenes Baker and Smith
(1920)
0.5 #-pinene Miranda et al. (1981)
p-cymene (42), #-terpineol (5)
E. brachycalyx 1.3 dry #-pinene (8), 1,8-cineole (25), Bignell et al. (1994b)
p-cymene (13)
E. brachycorys 0.8 dry !-pinene (7), 1,8-cineole (25), Bignell et al. (1997g)
p-cymene (9), cryptone (7)
E. brachyphylla 1.7 dry #-pinene (18), 1,8-cineole (58), Bignell et al. (1996c)
!-eudesmol (4)
E. brassiana 0.50.7 #-pinene, 1,8-cineole, citronellal Singh et al. (1991)


(%)
E. brevipes 0.7 dry 1,8-cineole (78), #-terpineol (4) Bignell et al. (1997g)
E. brevistylis 0.8 conglomerone (20), !-caryophyllene (8), Brophy unpubl.
humulene (10), sesquiterpenes (30)
E. bridgesiana 0.40.7 #-pinene, 1,8-cineole Baker and Smith
(syn. E. stuartiana) (1920)
0.41.0 #-pinene, limonene, 1,8-cineole (64), Boland et al. (1991)
#-terpineol
0.5 dry 1,8-cineole (70), aromadendrene (4) Bignell et al. (1997f )
E. brockwayi 0.2 dry #-pinene (21), 1,8-cineole (13), isoamyl Bignell et al. (1996e)
isovalerate (10), aromadendrene (14)
E. brookeriana 1.66.9 dry isovaleraldehyde, #-pinene, limonene, Brooker and Lassak
1,8-cineole, #-terpineol (1981)
3.6 dry #-pinene (18), #-phellandrene (5), Li et al. (1996)
1,8-cineole (53)
E. brownii 1.92.3 1,8-cineole (8090) Boland et al. 1991
E. bunites 0.71.3 #-pinene (75), !-pinene (7), #-, !-, Brophy et al. (1998b)
E. buprestium 0.2 dry #-pinene (12), 1,8-cineole (21), Bignell et al. (1997b)
linalool (5), #-terpineol (5)
E. burdettiana tr #-pinene (11), trans-pinocarveol (13), Bignell et al. (1996b)
E. burgessiana 1.11.5 #-pinene, #- and !-phellandrene, Lassak and Southwell
#-terpinene, p-cymene, terpinen- (1982)
4-ol, cis-and trans-p-menth-2-en-
1-ol, cis-and trans-piperitol,
#-, !-, $-eudesmol
E. burra- 3.6 dry #-pinene (13), 1,8-cineole (62), Bignell et al. (1994c)
coppinensis !-eudesmol (5)
E. cadens 0.51.3 #-pinene, 1,8-cineole (75), trans- Boland et al. (1991)
pinocarveol
E. caesia aromadendrene, globulol, torquatone Bowyer and Jefferies
(1959)
subsp. caesia 0.8 dry #-pinene (14), aromadendrene (27), Bignell et al. (1996c)
torquatone (18)
subsp. magna 0.5 dry #-pinene (7), aromadendrene (16), Bignell et al. (1996c)
torquatone (29)
E. calcareana 1.4 dry #-pinene (23), 1,8-cineole (20), Bignell et al. (1995a)
aromadendrene (19)
E. calcicola 0.3 dry #-pinene (14), limonene (12), Bignell et al. (1997g)
1,8-cineole (32)
0.2 1,8-cineole (13), #-terpineol (20), Brophy unpubl.
geraniol (6), #-, !-, $-eudesmol
(5 total), aromatic compounds (10)
E. caleyi 0.4 #-pinene, #-phellandrene, 1,8-cineole, Baker and Smith
(syn. E. coerulea) eudesmol (mixture of isomers) (1920)
0.1 dry aromadendrene (8), bicyclogermacrene Bignell et al. (1997a)
(34), globulol (9), viridiflorol (8)
0.8 #-pinene (15), limonene (6), 1,8-cineole Brophy unpubl.
(53)
E. caliginosa tr aromadendrene (8), globulol (5), #-, !-, Bignell et al. (1997f )
0.71.5 #-pinene (30), 1,8-cineole (6), #-, !-, Brophy unpubl.


(%)
E. calophylla 0.3 d-#-pinene, p-cymene, sesquiterpenes Baker and Smith

(1920)
tr #-pinene (10), $-terpinene (12), Bignell et al. (1996g)
E,E-farnesol (21)
0.5 #-pinene (51), $-terpinene (10), Brophy unpubl.
E,E-farnesol (11)
E. calycogona 1.0 d-#-pinene, 1,8-cineole, sesquiterpenes Baker and Smith
(1920)
#-pinene, #-phellandrene, 1,8-cineole, Brophy and Lassak
p-cymene, spathulenol, torquatone unpubl.
var. calycogona 1.4 dry #-pinene (27), 1,8-cineole (45) Bignell et al. (1997e)
E. camaldulensis
(syn. E. rostrata,
E. rostrata
var. borealis)
cineole-rich 0.81.2 pinene, 1,8-cineole Baker and Smith
form (1920), Gandini
(1936)
cineole-rich 1.21.7 #-pinene, limonene, 1,8-cineole Doran and Brophy
form (84), globulol (1990), Boland
et al. (1991)
cineole-poor 0.20.4 phellandrene, 1,8-cineole, p-cymene, Baker and Smith
form cuminal, phellandral (1920), Gandini
(1936)
cineole-poor 2.3 !-pinene, bicyclogermacrene, Doran and Brophy
form globulol, viridiflorol (1990), Boland
et al. (1991)
var. 0.3 dry p-cymene (22), cryptone (14), Bignell et al. (1996a)
camaldulensis spathulenol (17)
var. obtusa 1.5 dry #-pinene (15), 1,8-cineole (62), Bignell et al. (1996a)
aromadendrene (3)
E. cameronii 0.9 #-pinene (19), 1,8-cineole (20), Brophy unpubl.
spathulenol (6), #-, !-, $-eudesmol
(30 total)
E. camfieldii 0.51.0 tasmanone Unpubl. (1961),
Hellyer et al. (1963)
E. campaspe 0.71.2 #-pinene, 1,8-cineole, p-cymene, Phillips (1923),
aromadendrene, geraniol Watson and Gardner
(1944/45)
1.9 dry #-pinene (14), 1,8-cineole (50), Bignell et al. (1996d)
aromadendrene (5), torquatone (9)
E. camphora 1.3 #-pinene, 1,8-cineole, eudesmol Baker and Smith
subsp. aquatica 1.94.0 dry 1,8-cineole (57), #-, !-, $-eudesmol Boland et al. (1991)
(33 total)
subsp. camphora 2.32.6 dry p-cymene (15), #-, !-, $-eudesmol Boland et al. (1991)
(75 total)
subsp. humeana 1.62.2 dry #-pinene, limonene, 1,8-cineole (70), Boland et al. (1991)
p-cymene, terpinyl acetate
subsp. relicta 2.63.4 dry #-pinene, limonene, 1,8-cineole (84), Boland et al. (1991)
#-terpineol
E. canaliculata 0.6 dry p-cymene (27), '-terpineol (19), Bignell et al. (1998)
cuminal (9)


(%)
E. capillosa
subsp. capillosa 1.8 dry #-pinene (9), 1,8-cineole (11), Bignell et al. (1997c)
bicyclogermacrene (17), globulol (7)
subsp. polyclada 1.1 dry #-pinene (6), 1,8-cineole (15), Bignell et al. (1997c)
p-cymene (10), bicyclogermacrene
(12), spathulenol (12)
E. capitellata 0.2 1,8-cineole (19), spathulenol (10), Brophy unpubl.
#-, !-, $-eudesmol (20 total)
E. captiosa 0.4 dry #-pinene (8), 1,8-cineole (38), trans- Bignell et al. (1997g)
pinocarveol (17), !-eudesmol (7)
E. carnabyi 1.0 dry #-pinene (28), 1,8-cineole (14), Bignell et al. (1994c)
aromadendrene (16)
E. carnei 1.7 dry #-pinene (33), 1,8-cineole (45), Bignell et al. (1996c)
aromadendrene (3)
E. catenaria 0.21.2 #-pinene (80), globulol (2), Brophy et al. (1998b)
guaiol (3)
E. celastroides
subsp. 2.4 dry #-pinene (27), 1,8-cineole (37), Bignell et al. (1997e)
celastroides aromadendrene (11)
subsp. virella 0.6 dry 1,8-cineole (29), p-cymene (14), Bignell et al. (1997e)
cryptone (9)
E. cephalocarpa 0.71.8 dry #-pinene, limonene, 1,8-cineole (85) Boland et al. (1991)
E. ceratocorys 1.2 dry #-pinene (26), 1,8-cineole (36), Bignell et al. (1994a)
aromadendrene (10)
E. chapmaniana 2.42.7 1,8-cineole (60), $-terpinene, Boland et al. (1991)
E. chlorophylla 0.50.6 limonene, 1,8-cineole (80), Boland et al. (1991)
E. cinerea 1.11.2 #-pinene, 1,8-cineole, Baker and Smith
(syn. E. stuartiana butyraldehyde, valeraldehyde (1920)
var. cordata) 2.83.5 #-pinene, 1,8-cineole (78) Boland et al. (1991)
E. citriodora
Type 0.54.2 citronellal ("65) Baker and Smith
(1920), Boland et al.
(1991), Bignell
et al. (1997f)
Var. A 0.82.0 citronellol and its acetate, Penfold and Morrison
citronellal (1948), Penfold
et al. (1951)
Intermediate 0.11.4 citronellal (2050), guaiol Penfold et al. (1948),
form Penfoldet al. (1950),
Harris and McKern
(1950), Unpubl.
(1961)
Hydrocarbon 0.20.5 citronellal ((10), hydrocarbons Penfold et al. (1950),
form Unpubl. (1961)
E. cladocalyx 0.1 d-#-pinene, 1,8-cineole Baker and Smith
(syn. E. (1920)
corynocalyx) tr p-cymene (5), caryophyllene Bignell et al. (1996g)
oxide (14), spathulenol (10),
!-eudesmol (4)
E. clarksoniana 0.20.5 #- and !-pinene, Boland et al. (1991)
bicyclogermacrene, globulol


(%)
E. clelandii #-pinene, 1,8-cineole, trans- Brophy and Lassak

pinocarveol, !-eudesmol, torquatone unpubl.
1.8 dry #-pinene (19), 1,8-cineole (63), trans- Bignell et al. (1995a)
pinocarveol (4)
E. clivicola 0.2 dry #-pinene (13), 1,8-cineole (21), Bignell et al. (1997c)
aromadendrene (11),
E. cloeziana 0.1 dry #-pinene (16), caryophyllene oxide (8) Bignell et al. (1997f)
pinene-rich 0.20.6 #-pinene (78), !-pinene, limonene, Brophy and Boland
form #-terpineol, globulol (1990), Boland et al.
(1991)
tasmanone-rich 1.51.9 tasmanone (96) Brophy and Boland
form (1990), Boland et al.
(1991)
E. cneorifolia 2.0 #- and !-phellandrene, 1,8-cineole, Baker and Smith
p-cymene, l-cryptone (1920), Berry (1947)
0.9 dry 1,8-cineole (40), p-cymene (14), Bignell et al. (1997d)
cryptone (9)
E. coccifera 0.6 l-#-phellandrene, sesquiterpenes Baker and Smith
(1920)
0.92.5 dry #-phellandrene (9), p-cymene (10), Li et al. (1995)
cis- and trans-menth-2-en-1-ol
(10 total), #-, !-, $-eudesmol
(32 total)
0.6 1,8-cineole (20), globulol (8), #-, Brophy unpubl.
E. concinna 1.71.8 dry #-pinene, 1,8-cineole, Marshall and Watson
aromadendrene, geraniol (1939/40)
4.2 dry #-pinene (23), !-pinene (8), Bignell et al. (1994b)
1,8-cineole (14)
E. conferruminata 0.7 dry #-pinene (23), 1,8-cineole (22), Bignell et al. (1996b)
!-eudesmol (4)
E. conglobata 0.1 dry #-pinene (8), p-cymene (16), Bignell et al. (1995a)
!-caryophyllene (10),
spathulenol (24)
E. conglomerata 0.10.2 l-#-phellandrene, conglomerone, Lahey and Jones
0.6 !-caryophyllene (8), globulol Brophy unpubl.
(12), E,E-farnesol (9),
conglomerone (11)
E. conica 0.6 #-pinene, 1,8-cineole, Baker and Smith
0.9 dry 1,8-cineole (15), p-cymene (12), Bignell et al. (1997a)
bicyclogermacrene (8),
spathulenol (17)
E. consideniana 1.2 #-pinene, #-phellandrene, 1,8-cineole, Baker and Smith
eudesmol (mixture of isomers) (1920)
2.4 1,8-cineole (50), p-cymene (10), Brophy unpubl.
#-terpineol (8)
E. coolabah
subsp. coolabah tr p-cymene (6), aromadendrene (14), Bignell et al. (1997a)
palustrol (14), globulol (9)


(%)
subsp. tr bicyclogermacrene (53), Bignell et al. (1997a)

microtheca '-cadinene (4)
E. cooperiana 2.4 dry #-pinene (25), 1,8-cineole (16), Bignell et al. (1996e)
aromadendrene (19)
E. cordata 2.3 d-#-pinene, 1,8-cineole Baker and Smith
(1920)
4.46.4 dry #-pinene (16), 1,8-cineole (64), Li et al. (1996)
#-terpineol (4), #-terpinyl
acetate (6)
E. cornuta 1.2 d-#-pinene, 1,8-cineole Baker and Smith
(1920)
0.4 dry 1,8-cineole (62), p-cymene (5), trans- Bignell et al. (1996b)
pinocarveol (7)
E. coronata 0.8 dry 1,8-cineole (44), #-, !-, $-eudesmol Bignell et al. (1997b)
(25 total)
E. corrugata 2.2 dry 1,8-cineole (12), p-cymene (17), Bignell et al. (1994b)
cryptone (12)
E. cosmophylla 0.6 #-pinene, 1,8-cineole Baker and Smith
(1920)
0.2 dry 1,8-cineole (51), trans-pinocarveol (5) Bignell et al. (1996g)
E. crebra 0.2 #-pinene, l-#-phellandrene, Baker and Smith
cineole-rich 0.50.9 #-pinene (9), 1,8-cineole (66), Boland et al. (1991)
form globulol
pinene-rich 0.50.9 #-pinene (26), !-pinene (30), Boland et al. (1991)
form limonene, aromadendrene, globulol
0.5 dry 1,8-cineole (37), aromadendrene (9), Bignell et al. (1997a)
spathulenol (6)
E. crenulata 0.9 isovaleraldehyde, #-pinene, Hellyer et al. (1964)
$-terpinene, p-cymene, methyl
eudesmate, terpinolene,
terpinen-4-ol
0.70.9 $-terpinene, p-cymene, terpinen- Boland et al. (1991)
4-ol, !-phenylethyl phenylacetate
(35), phenylacetic acid esters
bark 1.5 isovaleraldehyde, #- and !-pinene, Lassak and Southwell
#-terpinene, p-cymene, methyl (1969)
eudesmate, !-phenylethyl
phenylacetate
E. cretata 1.9 dry #-pinene (15), 1,8-cineole (19), Bignell et al. (1995a)
p-cymene (16), aromadendrene (7)
E. croajingolensis #-pinene (14), 1,8-cineole (30), Brophy and Doran
#-terpineol (30), terpinen-4-ol (4) unpubl.
E. crucis
subsp. crucis 2.2 dry #-pinene (16), 1,8-cineole (62), Bignell et al. (1996c)
!-eudesmol (5)
subsp. 3.8 dry #-pinene (8), 1,8-cineole (62), Bignell et al. (1997g)
lanceolata !-eudesmol (9)
E. cullenii 0.41.8 dry 1,8-cineole (40), p-cymene (38) Brophy unpubl.
E. cunninghamii 1.92.8 #-pinene, #- and !-phellandrene, Lassak and Southwell
(syn. E. rupicola) p-cymene, piperitone (1982)
E. cuprea 1.3 dry #-pinene (13), 1,8-cineole (49), Bignell et al. (1995c)
#-terpineol (6)


(%)
E. curtipes 0.1 dry #-pinene (6), globulol (12), Brophy et al. (1998b)
spathulenol (33)
E. curtisii 0.1 !-pinene (17), E-!-ocimene (11), Brophy et al. (1998a)
globulol (9)
E. cyanophylla 2.1 dry #-pinene (16), 1,8-cineole (14), Bignell et al. (1995a)
aromadendrene (31), globulol (9)
E. cyclostoma 2.0 dry #-pinene (31), 1,8-cineole (34), Bignell et al. (1997e)
!-eudesmol (3)
E. cylindriflora 1.5 dry #-pinene (20), 1,8-cineole (34), Bignell et al. (1996c)
E. cylindrocarpa 1.9 dry #-pinene (22), !-pinene (9), Bignell et al. (1997e)
1,8-cineole (17), p-cymene (10)
E. cypellocarpa 1.92.6 1,8-cineole (64), !-eudesmol (20) Boland et al. (1991)
E. dalrympleana 0.5 #-pinene, 1,8-cineole Baker and Smith (1920)
0.71.1 #-pinene, limonene, 1,8-cineole Boland et al. (1991)
(78), p-cymene
0.8 dry p-cymene (20), globulol (11), Li et al. (1996)
viridiflorol (8), spathulenol (32)
subsp. heptantha 0.1 globulol (8), viridiflorol (8), Brophy unpubl.
spathulenol (25)
E. dawsonii 0.8 l-#-phellandrene, sesquiterpenes Baker and Smith
(1920)
eudesmol- 4.2 dry globulol (16), #-, !-, $-eudesmol Boland et al. (1991)
isobicyclo 2.23.2 dry spathulenol (9), isobicyclogermacral Boland et al. (1991)
germacral- (44), farnesol (7), sesquiterpene
rich form alcohol (14)
0.7 dry alloaromadendrene (8), Bignell et al. (1998)
E. dealbata 0.9 #-pinene, 1,8-cineole, sesquiterpenes Baker and Smith (1920)
1.7 dry #-pinene (2), 1,8-cineole (81) Bignell et al. (1996a)
E. deanei 0.6 #-pinene, 1,8-cineole, p-cymene, Baker and Smith
cuminal, phellandral, cryptone, (1920), Mus. A. and
sesquiterpenes S. unpubl.
E. decipiens tr 1,8-cineole (9), trans-pinocarveol Bignell et al. (1997d)
(15), isobicyclogermacral (12)
E. decorticans 0.3 leptospermone, flavesone Bick et al. (1965),
Hellyer (1968)
0.10.2 !-pinene (28), 1,8-cineole (10), Brophy unpubl.
#-terpineol (6), globulol (12)
E. decurva 0.2 dry #-pinene (4), 1,8-cineole (44), Bignell et al. (1996d)
aromadendrene (4)
E. deglupta 0.2 dry isovaleraldehyde, #-pinene, Webb et al. (1956)
(syn. #-phellandrene, p-cymene,
E. naudiniana) ocimene, nerolidol
0.1 nerolidol (66) Martnez et al. (1986)
E. delegatensis 1.83.9 l-#- and !-phellandrene, p-cymene, Baker and Smith
(syn. E. gigantea) piperitone, cis- and trans-p-menth-2- (1920), Weston
subspp. en-1-ol, trans-piperitol, 4-phenyl-2- (1984)
delegatensis, butanone, methyl cinnamate,
tasmaniensis #-, !-, $-eudesmol


(%)
2.6 dry l-#- and !-phellandrene, p-cymene, Boland et al. (1991)

piperitone, cis- and trans-p-menth-
2-en-1-ol, trans-piperitol, methyl
cinnamate, #-, !-, $-eudesmol
seedling leaves tr-0.1 #- and !-phellandrene, #-terpinene, Boland et al. (1982)
p-cymene, trans-piperitol,
4-phenyl-2-butanone, methyl
cinnamate, #-, !-, $-eudesmol
subsp. 3.25.6 dry #-phellandrene (16), !-phellandrene Li et al. (1995)
tasmaniensis (11), p-cymene (11), cis- and trans-
menth-2-en-1-ol (20 total)
E. dendromorpha 0.32.1 dry #- and !-phellandrene, #-terpinene, Lassak and Southwell
p-cymene, cis- and trans-p-menth-2- (1982)
en-1-ol, piperitone
E. densa subsp. 1.1 dry #-pinene (19), 1,8-cineole (33), Bignell et al. (1997c)
improcera bicyclogermacrene (10)
E. denticulata 0.7 dry 1,8-cineole (11), $-terpinene (22), Li et al. (1994)
p-cymene (30), #-terpineol (3)
E. desmondensis 1.1 dry #-pinene (12), 1,8-cineole (48), Bignell et al. (1997c)
aromadendrene (10)
E. desquamata 3.1 dry #-pinene (3), 1,8-cineole (79), Bignell et al. (1995c)
p-cymene (3)
E. deuaensis 67 dry #-pinene, limonene, 1,8-cineole, Boland et al. (1986)
p-cymene, terpinolene, #-terpineol,
piperitone, #-, !-, $-eudesmol
E. dielsii 4.1 dry #-pinene (50), 1,8-cineole (34) Bignell et al. (1996c)
E. dimorpha 0.5 #-pinene (52), globulol (6), #-, !-, Brophy et al. (1998b)
E. diptera 1.7 dry #-pinene (25), 1,8-cineole (20), Bignell et al. (1996d)
aromadendrene (12)
E. dissimulata 1.0 dry #-pinene (9), 1,8-cineole (30), Bignell et al. (1997d)
aromadendrene (12),
alloaromadendrene (12)
E. distans 1.51.9 1,8-cineole (69), p-cymene (25) Boland et al. (1991)
E. diversicolor 0.81.1 d-#-pinene, 1,8-cineole, Baker and Smith
d-#-terpineol, butyl butyrate (1920)
tr 1,8-cineole (18), trans-pinocarveol Bignell et al. (1996g)
(18), #-terpineol (11)
E. diversifolia 0.4 l-limonene (?), 1,8-cineole, Baker and Smith
(syn. sesquiterpenes (1920)
E. santalifolia) 0.6 dry #-pinene (17), limonene (22), 1,8- Bignell et al. (1997b)
cineole (38)
E. dives 4.76.0 dry #-phellandrene (20), piperitone (53) Boland et al. (1991),
Bignell et al. (1998)
Type 3.04.0 l-#-phellandrene (2030), Baker and Smith
l-piperitone, (4056) (1920), Hellyer
et al. (1969)
Var. A 1.55.1 l-#-phellandrene (6080), Penfold and Morrison
l-piperitone (28) (1927a), (1929)


(%)
Var. B 2.93.9 l-#-phellandrene, 1,8-cineole Penfold and Morrison

(25 40), piperitone (1218) (1927a)
Var. C 3.04.0 1,8-cineole (6875), terpineol, Baker and Smith
geraniol, citral (1920), Penfold and
Morrison (1927a)
E. dolichorhyncha 1.3 dry #-pinene (11), 1,8-cineole (32), Bignell et al. (1994a)
aromadendrene (12)
E. doratoxylon tr 1,8-cineole (8), bicyclogermacrene Bignell et al. (1996d)
0.1 #-pinene (6), bicyclogermacrene Brophy unpubl.
(15), globulol (8)
E. drepanophylla tr #-pinene (28), 1,8-cineole (15), Bignell et al. (1997a)
!-eudesmol (5), torquatone (6)
E. drummondii 2.9 dry #-pinene (24), 1,8-cineole (43), Bignell et al. (1994c)
globulol (2)
E. dumosa 1.0 d-#-pinene, 1,8-cineole, Baker and Smith
sesquiterpenes (1920), Penfold and
Morrison (1951)
1.5 dry p-cymene (16), bicyclogermacrene Bignell et al. (1995a)
E. dundasii 0.2 d-#-pinene, 1,8-cineole, Marshall and Watson
aromadendrene, esters (1934/35)
0.5 dry #-pinene (35), 1,8-cineole (35), Bignell et al. (1996e)
aromadendrene (6)
E. dunnii 0.92.1 #-pinene, 1,8-cineole (44), Boland et al. (1991)
aromadendrene, #-terpineol,
globulol
0.6 dry #-pinene (7), 1,8-cineole (32), Bignell et al. (1997f )
aromadendrene (16), trans-
pinocarveol (7)
E. dura tr-0.1 #-pinene (15), 1,8-cineole (15), Brophy unpubl.
spathulenol (3)
0.1 !-phellandrene (16), 1,8-cineole (23) Doimo et al. (1999)
E. dwyeri 1.62.0 dry 1,8-cineole, p-cymene, Boland et al. (1991)
isobicyclogermacrene, spathulenol,
sesquiterpene alcohols
pinocarveol (3)
E. ebbanoensis 1.8 dry #-pinene (26), aromadendrene (15), Bignell et al. (1996f )
E. effusa
subsp. effusa 0.3 dry #-pinene (8), 1,8-cineole (31), Bignell et al. (1996g)
!-caryophyllene (8)
subsp. exsul 1.3 dry #-pinene (4), 1,8-cineole (71), trans- Bignell et al. (1996g)
pinocarveol (7)
E. elaeophloia 0.2 1,8-cineole (8), p-cymene (20), Brophy unpubl.
spathulenol (31)
E. elata 6.5 dry #-phellandrene, p-cymene, piperitone, Boland et al. (1991)
(syn. cis- and trans-menth-2-en-1-ol, cis-
E. andreana, and trans-piperitol
E. numerosa)


(%)
Type 1.03.0 l-#-phellandrene, l-piperitone (510), Baker and Smith

(as E. radiata) trans-piperitol (1015) (1920), Penfold and
Morrison (1932)
Var. A 1.03.0 l-#-phellandrene, l-piperitone (4055), Baker and Smith
(syn. trans-piperitol (1920), Penfold and
E. lindleyana Morrison (1932)
var. stenophylla)
Var. B 1.72.7 l-#-phellandrene, 1,8-cineole (1215), Baker and Smith
(syn. l-piperitone (2030), trans-piperitol (1920), Penfold and
E. lindleyana) Morrison (1932)
E. erectifolia 0.3 dry #-pinene (11), 1,8-cineole (53), Bignell et al. (1997b)
#-terpineol (5)
E. eremicola 3.1 dry #-pinene (11), !-pinene (21), p-cymene Bignell et al. (1995b)
E. eremophila 1.8 dry d-#-pinene, 1,8-cineole, aldehydes, Marshall and Watson
aromadendrene, phenols, alcohols, (1936/37)
geraniol (?), eudesmols (?), esters
subsp. 3.0 dry #-pinene (12), 1,8-cineole (51), trans- Bignell et al. (1996d)
eremophila pinocarveol (8)
E. erythrandra 1.4 dry #-pinene (35), 1,8-cineole (32), Bignell et al. (1994a)
aromadendrene (8)
E. erythrocorys 0.5 dry #-terpineol (24), C10 diol ? (24) Bignell et al. (1996f )
E. erythronema 2.5 dry 1,8-cineole, geraniol Watson (1941/42)
var. erythronema 2.4 dry #-pinene (10), 1,8-cineole (57), Bignell et al. (1996c)
var. marginata 1.7 dry #-pinene (8), 1,8-cineole (10), Bignell et al. (1996c)
p-cymene (13), spathulenol (20)
E. erythrophloia 0.6 dry #-pinene (50), !-pinene (11), Brophy unpubl.
globulol (5)
E. eudesmioides
subsp. 1.3 dry #-pinene (10), 1,8-cineole (53), Bignell et al. (1996f )
eudesmioides globulol (3)
E. eugenioides 0.21.4 d- and l-#-pinene, phellandrene, 1,8- Baker and Smith
(syn. E. acervula, cineole, geraniol, geranyl acetate, (1920), Mus. A. and
E. wilkinsoniana) sesquiterpenes S. unpubl.
0.2 dry #-pinene (23), #-, !-, $-eudesmol Bignell et al. (1997f ),
(18 total) Brophy unpubl.
E. ewartiana 1.5 dry #-pinene (5), 1,8-cineole (75), Bignell et al. (1996c)
#-terpineol (5)
E. exilipes 0.50.9 #-pinene (14), limonene (16), 1,8- Brophy unpubl.
cineole (8), #-, !-, $-eudesmol
(18 total)
E. exilis 0.1 dry #-pinene (7), 1,8-cineole (43), Bignell et al. (1997b)
#-terpineol (5)
E. eximia 0.50.8 d-#-pinene, eudesmol (mixture of Baker and Smith
isomers), sesquiterpenes (1920)
0.81.0 #-pinene (33), globulol (7), #-, !-, Brophy et al. (1998b)
E. exserta 0.8 d-#-pinene, 1,8-cineole, Baker and Smith
sesquiterpenes, aldehydes (1920)
0.41.2 #-pinene, 1,8-cineole, globulol Boland et al. 1991


(%)
pinocarveol (3)
E. falcata tr 1,8-cineole (11), aromadendrene Bignell et al. (1997d)
E. famelica 0.5 dry 1,8-cineole (86) Bignell et al. (1997e)
E. fasciculosa tr 1,8-cineole Baker and Smith
(1920)
#-terpineol (5)
E. fastigata 0.12.4 d-#-pinene, #-phellandrene, Baker and Smith
1,8-cineole (1920)
0.51.3 #-, !-, $-eudesmol (up to 70 total) Brophy unpubl.
E. fibrosa 0.30.5 #-pinene (7), limonene (5), Brophy unpubl.
1,8-cineole (55)
subsp. fibrosa 0.1 dry 1,8-cineole (37), aromadendrene (12), Bignell et al. (1997a)
globulol (5)
E. ficifolia 0.2 #-thujene (5), #-pinene (66), !-pinene Briggs and Bartley
(8), $-terpinene (14), p-cymene (8) (1970)
0.20.5 #-pinene (36), farnesol (17) Boland et al. (1991)
tr bicyclogermacrene (43), spathulenol (3) Bignell et al. (1996g)
E. flavida 1.6 dry #-pinene (19), 1,8-cineole (62) Bignell et al. (1997c)
E. flindersii 0.8 dry #-pinene (12), 1,8-cineole (49), Bignell et al. (1996a)
$-terpinene (3)
E. flocktoniae 1.8 #-pinene, 1,8-cineole, Watson (1934/35)
aromadendrene, alcohols
2.9 dry #-pinene (31), 1,8-cineole (40), Bignell et al. (1995b)
aromadendrene (7)
E. foecunda 1.4 d-pinene, 1,8-cineole, p-cymene, Baker and Smith
(misidentified aldehydes, sesquiterpenes (1920)
as E. uncinata 0.9 dry 1,8-cineole (62), !-eudesmol (5) Bignell et al. (1997d)
by Baker and
Smith)
E. formanii 1.9 dry #-pinene (17), 1,8-cineole (57), Bignell et al. (1997d)
E. forrestiana 3.3 dry #-pinene (31), 1,8-cineole (17), Bignell et al. (1994a)
aromadendrene (7),
E. fraseri 2.7 dry #-pinene (26), 1,8-cineole (30), Bignell et al. (1995a)
aromadendrene (11)
E. fraxinoides 1.0 l-#-phellandrene, 1,8-cineole, Baker and Smith
piperitone, #-, !-, $-eudesmol (1920), Lassak and
Southwell (1982)
E. froggattii leptospermone Hellyer (1968)
E. fusiformis 0.10.2 dry #-pinene, pinocarvone, Boland et al. (1987)
aromadendrene, trans-pinocarveol,
#-terpineol, borneol, spathulenol
E. gamophylla 2.6 dry 1,8-cineole (6), bicyclogermacrene Bignell et al. (1996f )
E. gardneri
subsp. 1.3 dry 1,8-cineole (6), spathulenol (10), Bignell et al. (1997c)
gardneri isobicyclogermacral (41)
subsp. 1.5 dry p-cymene (7), !-caryophyllene (11), Bignell et al. (1997c)
ravensthorpensis isobicyclogermacral (33)


(%)
E. georgei 1.8 dry #-pinene (5), $-terpinene (26), Bignell et al. (1995a)
p-cymene (39), aromadendrene (7)
E. gillenii 0.6 dry #-pinene (8), 1,8-cineole (51), Bignell et al. (1996a)
aromadendrene (11)
E. gillii 3.2 dry #-pinene (21), 1,8-cineole (10), Bignell et al. (1995b)
E. gittinsii 0.3 dry 1,8-cineole (47), aromadendrene Bignell et al. (1996f )
(8), globulol (4)
E. glaucescens 2.12.6 #-pinene, 1,8-cineole (49), isoamyl Boland et al. (1991)
isovalerate, aromadendrene,
globulol
E. globoidea 0.21.1 1,8-cineole (40), p-cymene (15), #-, Brophy unpubl.
(syn. E. yangoura) !-, $-eudesmol (10 total)
E. globulus
subsp. 1.12.4 dry, d-#-pinene, 1,8-cineole, eudesmol Penfold and Morrison
bicostata (syn. 1.02.0 (mixture of isomers) (1930), Boland et al.
E. bicostata) (1991)
0.8 dry 1,8-cineole (69), aromadendrene (6) Bignell et al. (1996f)
subsp. globulus 0.51.5 isovaleraldehyde, d-#-pinene, 1,8- Baker and Smith
cineole, l-pinocarveol, #-terpineol, (1920), Gildemeister
globulol, sesquiterpenes and Hoffmann
(1961)
2.8 4.0 dry #-pinene (18), 1,8-cineole (55), Li et al. (1996)
globulol (5)
aromadendrene (12)
fruits ? 1,8-cineole, aromadendrene, Nishimura et al.
alloaromadendrene, globulol (1979)
fruits 2.1 1,8-cineole (73), 27 other Baslas and Saxena
compounds incl. methyl eugenol, (1984)
eugenol, carvacrol
subsp. maidenii 1.02.8 isovaleraldehyde, #-pinene, Baker and Smith
(syn. E. maidenii) 1,8-cineole, aromadendrene, (1920), Rutowski
borneol, isoamyl alcohol, eudesmol and Winogradowa
(mixture of isomers) (1927), Boland
et al. (1991)
1.6 dry 1,8-cineole (59), aromadendrene (12) Bignell et al. (1996f)
subsp. 4.05.6 dry #-pinene, 1,8-cineole (70), Boland et al. (1991)
pseudoglobulus (syn. !-eudesmol
E. pseudoglobulus, 1.6 dry #-pinene (12), 1,8-cineole (52) Bignell et al. (1996f)
E. stjohnii)
E. glomerosa 1.62.2 dry 1,8-cineole (62), pinocarvone Bignell et al. (1996g),
(5), trans-pinocarveol (10) (1997g)
E. gomphocephala tr-0.1 #-pinene, #-phellandrene Baker and Smith
(1920), Miranda
et al. (1981)
tr trans-pinocarveol (7), carvone (9), Bignell et al. (1996g)
globulol (6), !-eudesmol (4)
E. gongylocarpa 1.9 dry #-pinene (47), 1,8-cineole (33) Bignell et al. (1996f)
#-pinene, 1,8-cineole, trans- Brophy and Lassak
pinocarveol, #-terpineol, globulol unpubl.


(%)
bark [as 1.0 1,8-cineole, globulol Blumann et al. (1953)

E. eudesmioides]
E. goniantha 1.2 d-#-pinene, 1,8-cineole, Marshall and Watson
subsp. aromadendrene (1934/35)
goniantha 0.4 dry #-pinene (37), 1,8-cineole (20), Bignell et al. (1997d)
E. goniocalyx 1.02.5 d-#-pinene, 1,8-cineole, eudesmol Baker and Smith
(syn. E. elaeophora, (mixture of isomers), aldehydes, (1920)
E. cambagei) sesquiterpenes
0.40.9 limonene, 1,8-cineole (78), Boland et al. (1991)
#-terpineol
E. gracilis 0.9 d-#-pinene, 1,8-cineole, p-cymene, Baker and Smith
aldehydes (1920)
0.6 dry p-cymene (11), cryptone (10) Bignell et al. (1997e)
E. grandifolia 0.2 dry #-pinene (74), spathulenol (2) Brophy unpubl.
E. grandis 0.20.6 #-pinene (25), 1,8-cineole (6), Boland et al. (1991)
spathulenol, leptospermone (26),
flavesone (12), isoflavesone (3)
[as E. saligna 0.10.3 d-#-pinene, 1,8-cineole, esters, Baker and Smith
var. alcohols (1920)
pallidivalvis]
E. granitica 0.4 1,8-cineole (82) Brophy unpubl.
0.51.3 dry #-pinene (18), 1,8-cineole (60), Brophy unpubl.
#-terpineol (2)
E. gregsoniana 0.8 1,8-cineole (18), #-, !-, $-eudesmol Brophy unpubl.
(50 total)
E. griffithsii 0.3 dry #-pinene (8), 1,8-cineole (26), Bignell et al. (1994b)
E. grossa 2.5 dry #-pinene (37), 1,8-cineole (36), Bignell et al. (1996e)
aromadendrene (5)
#-pinene, myrcene, 1,8-cineole, Brophy and Lassak
globulol, viridiflorol, spathulenol unpubl.
E. guilfoylei tr dry viridiflorene (30), myrtenol (6), Bignell et al. (1997g)
torquatone (7)
E. gummifera 0.1 #-pinene, sesquiterpenes Baker and Smith
(syn. E. corymbosa) (1920)
tr !-caryophyllene (6), Bignell et al. (1997f )
bicyclogermacrene
(34), torquatone (6)
0.4 !-pinene (32), globulol (14) Brophy unpubl.
E. gunnii 0.7 d-#-pinene, l-#-phellandrene, Baker and Smith
1,8-cineole (1920)
0.50.9 #-phellandrene, p-cymene, globulol, Boland et al. (1991)
bicyclogermacrene, spathulenol
E. haemastoma 0.30.5 d-#-pinene, 1,8-cineole, eudesmol Penfold and Morrison
(mixture of isomers) (1927b), Mus. A.
and S. unpubl.
E. haematoxylon 0.2 dry #-pinene (17), $-terpinene (16), Bignell et al. (1996g)
E,E-farnesol (28)
E. halophila 0.6 dry #-pinene (17), !-pinene (16), Bignell et al. (1996e)
1,8-cineole (12), aromadendrene (13)


(%)
E. hamersleyana tr bicyclogermacrene (38), Bignell et al. (1997f)

calamenene (7)
E. hebetifolia 0.3 dry #-pinene (22), 1,8-cineole (31), Bignell et al. (1997c)
aromadendrene (8)
E. henryi 0.91.3 dry 1,8-cineole (27), '-cadinene (5), Brophy unpubl.
cadinols/muurolols (22 total)
E. histophylla 1.5 dry #-pinene (22), 1,8-cineole (43), Bignell et al. (1997c)
aromadendrene (5)
E. horistes 2.1 4.7 dry 1,8-cineole Gardner and Watson
(syn. E. oleosa (1947/48)
var. borealis) 3.4 dry 1,8-cineole (88), p-cymene (1) Bignell et al. (1995b)
E. imlayensis 0.30.4 #-pinene, 1,8-cineole, Boland et al. (1991)
#-terpineol, spathulenol
E. incerata 2.8 dry #-pinene (7), bicyclogermacrene (66) Bignell et al. (1998)
E. incrassata 2.8 dry #-pinene (18), 1,8-cineole (30), Bignell et al. (1994a)
(syn. E. costata) aromadendrene (13)
E. indurata 0.5 dry 1,8-cineole (22), trans-pinocarveol (14), Bignell et al. (1997d)
spathulenol (6)
E. insularis tr #-pinene (20), !-pinene (16), Bignell et al. (1997b)
1,8-cineole (15)
E. intermedia 0.1 d-#-pinene, aldehydes, sesquiterpenes Baker and Smith
(1920)
0.20.5 #-pinene (41), !-pinene (26), #-, !-, Boland et al. (1991)
$-eudesmol
E. intertexta 0.2 #-pinene, 1,8-cineole Baker and Smith
(syn. (1920)
E. intertexta 1.5 dry, #-pinene, 1,8-cineole, p-cymene, Brophy and Lassak
var. fruticosa) 0.41.6 trans- pinocarveol, globulol (1986), Boland et al.
(1991)
1.1 dry #-pinene (18), limonene (4), Bignell et al. (1995c)
1,8-cineole (68)
E. irbyi 0.2 #-pinene, #-phellandrene, 1,8-cineole, Baker and Smith
[hybrid, sesquiterpenes (1920)
E. dalrympleana
subsp.
dalrympleana )
E. gunnii subsp.
gunnii]
E. jacksonii 1.0 dry jacksonone (60), cryptone (6) Bignell et al. (1997b)
E. jensenii 0.10.3 jensenone (70) Boland et al. (1991)
E. johnsoniana 0.8 dry 1,8-cineole (56), spathulenol (3) Bignell et al. (1997b)
E. johnstonii 1.3 d-#-pinene, 1,8-cineole Baker and Smith
(syn. E. muelleri) (1920)
0.51.8 #-pinene, limonene, 1,8-cineole, Boland et al. (1991)
$-terpinene, #-terpinyl acetate,
#-, !-, $- eudesmol
4.65.0 dry #-pinene (19), limonene (6), Li et al. (1996)
1,8-cineole (62)
E. jutsonii 2.3 dry #-pinene (10), !-pinene (9), Bignell et al. (1996b)
1,8-cineole (63)
E. kartzoffiana 1.52.2 #-pinene, 1,8-cineole (72), Boland et al. (1991)


(%)
E. kessellii 1.1 dry #-pinene (19), 1,8-cineole (16), Bignell et al. (1997d)
aromadendrene (11)
E. kingsmillii 1.3 dry #-pinene (23), 1,8-cineole (31), Bignell et al. (1994c)
subsp. 2.1 dry 1,8-cineole (55), trans-pinocarveol Bignell et al. (1997g)
alatissima (13)
E. kirtoniana 0.3 limonene (?), citral, sesquiterpenes Baker and Smith
[hybrid, (1920)
E. robusta )
E. tereticornis]
E. kitsoniana 2.1 #-pinene, dipentene, 1,8-cineole, Hellyer and McKern
aromadendrene, sesquiterpene (1966)
alcohols
E. kochii
subsp. kochii 2.53.5 dry #-pinene, 1,8-cineole, p-cymene Gardner and Watson
(syn. (1947/48), Brooker
E. oleosa et al. (1988)
var. kochii) 3.0 dry #-pinene (1), 1,8-cineole (82), Bignell et al. (1995b)
cryptone (1)
subsp. 2.28.6 dry #-pinene, 1,8-cineole, p-cymene Gardner and Watson
plenissima (syn. (1947/48),
E. plenissima) Brooker et al. (1988)
E. kondininensis 3.5 dry #-pinene (28), 1,8-cineole (50), Bignell et al. (1995a)
$-terpinene (4)
E. kruseana 1.0 dry #-pinene (22), 1,8-cineole (51), Bignell et al. (1996c)
!-eudesmol (6)
E. kumarlensis 0.7 dry 1,8-cineole (56), pinocarvone (6), Bignell et al. (1997d)
E. kybeanensis 1.7 p-cymene (12), #-, !-, $-eudesmol Brophy unpubl.
(53 total)
E. laevopinea 0.6 l-#-pinene, 1,8-cineole Baker and Smith
(1920)
tr 1,8-cineole (7), #-, !-, $-eudesmol Bignell et al. (1997f )
(25 total)
1.3 #-pinene (20), 1,8-cineole (18), #-, !-, Brophy unpubl.
1.1 #-pinene (60), 1,8-cineole (7), #-, !-, Brophy unpubl.
E. lane-poolei 1.0 dry #-pinene (24), 1,8-cineole (51), Bignell et al. (1994c)
E. lansdowneana
subsp. 0.5 dry #-pinene (9), !-phellandrene (9), Bignell et al. (1995c)
albopurpurea bicyclogermacrene (32)
subsp. 1.3 dry #-pinene (27), 1,8-cineole (39), Bignell et al. (1995c)
lansdowneana trans-pinocarveol (2)
E. largiflorens 0.9 pinene, 1,8-cineole, aldehydes Baker and Smith
(syn. E. bicolor) (1920)
0.9 dry #-pinene (4), 1,8-cineole (44), Bignell et al. (1995c)
aromadendrene (18)


(%)
E. laseroni 0.4 #-pinene, #-phellandrene, Baker and Smith

[hybrid, 1,8-cineole, sesquiterpenes (1920)
E. caliginosa )
E. stellulata]
E. latens 1.6 dry #-pinene (9), 1,8-cineole (40), Bignell et al. (1997d)
p-cymene (23)
E. lateritica 0.9 dry 1,8-cineole (24), tasmanone (37), Bignell et al. (1997b)
lateriticone (14)
E. latifolia tr #-pinene (12), aromadendrene Bignell et al. (1997f)
(15), globulol (7)
E. lehmannii 0.9 d-#-pinene, 1,8-cineole, aldehydes Baker and Smith
(1920)
2.1 dry #-pinene (27), 1,8-cineole (32), Bignell et al. (1996b)
$-terpinene (15)
E. leichhardtii 0.40.9 #-pinene (84), 3-phenylpropanal (5) Brophy et al. (1998b)
E. leizhou #-pinene (13), 1,8-cineole (37), Chen et al. (1983)
No. 1 [natural p-cymene (4), trans-pinocarveol (4)
hybrid of
E. exserta in
China]
E. lenziana tr bicyclogermacrene (10), '-cadinene Bignell et al. (1997f )
(20), #-, !-, $-eudesmol (10 total)
E. leptocalyx 0.8 dry #-pinene (20), 1,8-cineole (38), trans- Bignell et al. (1996b)
pinocarveol (9)
E. leptoloma 1.11.2 #-pinene (88), 3-phenylpropanal (5) Brophy et al. (1998b)
E. leptophleba 0.40.6 #- and !-pinene, spathulenol, Boland et al. (1991)
caryophyllene oxide
tr p-cymene (13), bicyclogermacrene (8), Bignell et al. (1997a)
spathulenol (8)
E. leptophylla 0.8 dry 1,8-cineole (66), aromadendrene (5), Bignell et al. (1997d)
E. leptopoda 1.3 #-pinene, 1,8-cineole, aromadendrene, Marshall and Watson
geraniol, aldehydes (1936/37)
2.0 dry #-pinene (15), limonene (2), Bignell et al. (1994c)
1,8-cineole (72)
subsp. elevata 2.1 dry 1,8-cineole (77), trans-pinocarveol (6) Bignell et al. (1996g),
(1997g)
E. lesouefii 5.1 dry #-pinene (16), 1,8-cineole (17), Bignell et al. (1995a)
aromadendrene (10),
leaf, bud, twig 1.4, 0.8, 0.3 #-pinene, 1,8-cineole, torquatone Brophy et al. unpubl.
E. leucophloia 1.21.7 1,8-cineole, p-cymene, globulol, Boland et al. (1991)
viridiflorol, spathulenol
E. leucoxylon 0.82.5 d-#-pinene, 1,8-cineole, Baker and Smith
aromadendrene (1920), Penfold and
Morrison (1951)
subsp. leucoxylon 1.1 dry #-pinene (7), aromadendrene (36), Bignell et al. (1995c)
subsp. petiolaris 2.1 dry #-pinene (26), 1,8-cineole (28), Bignell et al. (1995c)
aromadendrene (18)
E. ligulata 0.1 dry #-pinene (7), 1,8-cineole (49), Bignell et al. (1997b)
geraniol (5)


(%)
0.71.0 #-pinene (24), 1,8-cineole (37), Brophy unpubl.

geraniol (3)
E. ligustrina 0.1 geraniol, geranyl acetate, eudesmol Baker and Smith
(mixture of isomers), sesquiterpenes (1920)
0.10.5 1,8-cineole (18), #-, !-, Brophy unpubl.
E. livida 1.8 dry #-pinene (8), 1,8-cineole (18), Bignell et al. (1997c)
aromadendrene (9),
E. longicornis 1.2 #-pinene, 1,8-cineole, Baker and Smith
(syn. E. oleosa sesquiterpenes (1920)
var. longicornis)
E. longifolia 0.6 #-pinene, 1,8-cineole, Baker and Smith
1.1 #-pinene (59), !-pinene (16), Ndou and von
1,8-cineole (5) Wandruszka (1985)
0.6 dry 1,8-cineole (26), p-cymene (19), Bignell et al. (1996g)
aromadendrene (14), palustrol (7)
E. loxophleba 2.4 #-pinene, 4-methylpent-2-yl acetate, Boland et al. (1991)
1,8-cineole (67), trans-pinocarveol,
#-terpineol
subsp. gratiae 3.0 dry #-pinene (10), 1,8-cineole (72) Bignell et al. (1997g)
subsp. 1.9 dry 4-methylpent-2-yl acetate (4), 1,8- Bignell et al. (1997g)
lissophloia cineole (63), trans-pinocarveol (11)
subsp. 1.6 dry 4-methylpent-2-yl acetate (14), 1,8- Bignell et al. (1997g)
loxophleba cineole (25), aromadendrene (32)
E. lucasii 0.7 dry 1,8-cineole (50), aromadendrene (8), Bignell et al. (1997a)
E. lucens #-pinene, 1,8-cineole, camphor, Brophy and Lassak
pinocarvone, trans-pinocarveol (1986)
E. luehmanniana 0.4 1,8-cineole (41), #-terpineol (10), #-, Brophy unpubl.
E. macarthurii 0.21.1 d-#-pinene, myrcene, 1,8-cineole, Baker and Smith
p-cymene, linalool, geranyl acetate, (1920), McQuillin
geraniol, carissone, eudesmol and Parrack (1956),
(mixture of isomers) Agarwal et al.
(1970), Boland
et al. (1991)
bark 0.10.4 d-#-pinene, geranyl acetate, Baker and Smith
geraniol (1920), Neybergh
(1953)
E. macrandra 0.2 dry #-pinene (10), 1,8-cineole (31), Bignell et al. (1996e)
aromadendrene (8)
subsp. olivacea tr 1,8-cineole (19), aromadendrene Bignell et al. (1996e)
(20), alloaromadendrene (4)
E. macrocarpa
subsp. 0.7 dry #-pinene (13), aromadendrene (10), Bignell et al. (1994c)
elachantha bicyclogermacrene (25),
macrocarpa aromadendrene (21)
E. macrorhyncha
subsp. cannonii 1.0 globulol (20), viridiflorol (14), Brophy unpubl.
spathulenol (9), #-, !-, $-eudesmol
(17 total)


(%)
subsp. 0.3 #-pinene, #-phellandrene, 1,8-cineole, Baker and Smith

macrorhyncha eudesmol (mixture of isomers) (1920), Brophy et al.
(1982)
E. maculata 0.5 dry #-pinene (30), globulol (8), #-, !-, Bignell et al. (1997f )
0.7 limonene (5), 1,8-cineole (55), Brophy unpubl.
'-cadinene (4)
NSW form 0.20.8 d-#-pinene, d-limonene, dipentene, Baker and Smith
1,8-cineole, cadinene, cadinol, (1920), McKern
sesquiterpenes et al. (1954)
Queensland 0.71.1 dry d-#-pinene, guaiol, sesquiterpenes McKern et al. (1954),
form Unpubl. (1961)
E. malacoxylon 1.11.2 #-pinene, limonene, 1,8-cineole (69), Boland et al. (1991)
globulol
E. mannensis 1.5 dry #- and !-pinene, limonene, Brophy and Lassak
1,8-cineole, p-cymene (1986)
2.5 dry #- and !-pinene, 1,8-cineole (86) Bignell et al. (1996b)
E. mannifera 0.7 #-pinene (6), aromadendrene (17), Brophy unpubl.
globulol (30)
subsp. gullickii 0.4 #-pinene, 1,8-cineole, eudesmol Baker and Smith
(syn. E. gullickii) (mixture of isomers) (1920)
subsp. maculosa 1.1 #-pinene, 1,8-cineole, eudesmol Baker and Smith
(syn. E. maculosa) (mixture of isomers) (1920)
1.22.0 limonene (12), 1,8-cineole (68), Boland et al. (1991)
#-terpineol (7)
subsp. praecox 0.6 #-pinene, 1,8-cineole, p-cymene Baker and Smith
(syn. E. lactea) (1920)
E. marginata 0.2 #-pinene, p-cymene, sesquiterpenes, Baker and Smith
aldehydes (1920)
0.81.3 limonene (11), 1,8-cineole (14), Brophy unpubl.
p-cymene (13), menthyl acetate (4)
subsp. marginata 0.5 dry p-cymene (10), cryptone (9), Bignell et al. (1997b)
spathulenol (12)
subsp. thalassica tr p-cymene (13), cryptone (8) Bignell et al. (1997b)
E. marsdenii 0.7 sesquiterpenes Baker and Smith
[probably (1920)
a hybrid]
E. mckieana agglomerone Hellyer (1968)
E. megacarpa 0.5 l-#-pinene, #-terpinene, Baker and Smith
l-limonene, 1,8-cineole (1920)
tr dry 1,8-cineole (11), terpinolene (10) Bignell et al. (1997g)
E. megacornuta tr #-pinene (46), aromadendrene (9) Bignell et al. (1996b)
E. melanoleuca 0.20.4 #-pinene (36), 1,8-cineole (32), trans- Brophy unpubl.
pinocarveol (3), !-eudesmol (2)
E. melanophitra 0.8 dry #-pinene (16), 1,8-cineole Bignell et al. (1997c)
(15), $-terpinene (27),
E. melanophloia 0.1 #-pinene, #-phellandrene, 1,8-cineole, Baker and Smith
p-cymene, eudesmol (mixture of (1920)
isomers), sesquiterpenes
0.60.9 #-pinene (40), !-phellandrene, Boland et al. (1991)
1,8-cineole, #-terpineol, globulol


(%)
0.2 dry #-phellandrene (5), bicyclogermacrene Bignell et al. (1995c)

(30), globulol (8)
E. melanoxylon 2.3 dry #-pinene (11), 1,8-cineole (26), Bignell et al. (1994b)
p-cymene (11)
E. melliodora 0.9, #-pinene, #-phellandrene, 1,8-cineole Baker and Smith
2.33.1 dry (1920), Boland et al.
(1991)
0.1 dry 1,8-cineole (43), !-caryophyllene (5) Bignell et al. (1997a)
E. merrickiae 1.5 dry #-pinene (2), 1,8-cineole (25), Bignell et al. (1996e)
aromadendrene (7), !-eudesmol (6)
E. michaeliana leptospermone Hellyer (1968)
E. micranthera 0.5 dry #-pinene (20), a C6 acetate (27), Bignell et al. (1997d)
aromadendrene (5)
E. microcarpa 0.40.5 #-pinene, 1,8-cineole, p-cymene, Baker and Smith
(syn. phellandral, cuminal (1920)
E. woollsiana) tr dry trans-pinocarveol (8), Bignell et al. (1995c)
'-terpineol (4), torquatone (6)
E. microcorys 0.7 isovaleraldehyde, d-#-pinene, 1,8- Jones and Lahey
cineole, borneol and its esters (1938)
#-terpineol (5)
E. microtheca 0.5 #-pinene, l-#-phellandrene, Baker and Smith
0.30.4 1,8-cineole, p-cymene, globulol Boland et al. (1991)
E. miniata 1.0 dry #-pinene (85) Bignell et al. (1998)
0.21.2 dry #-pinene (26), 1,8-cineole (17), Brophy unpubl.
isobaeckeol, homoisobaeckeol and
their methyl ethers, apodophyllone,
isotorquatone, torquatone
E. mitchelliana 3.33.7 1,8-cineole (14), p-cymene (6), #-, !-, Brophy unpubl.
E. moluccana 0.40.9 1,8-cineole, p-cymene, l-cryptone, Baker and Smith
(syn. l-phellandral, cuminal, (1920), Penfold
E. hemiphloia) (1922)
0.7 #-pinene, limonene, 1,8-cineole (80), De Riscala and
p-cymene, cryptone, #-terpineol Retamar (1981)
0.1 dry p-cymene (6), cryptone (10), Bignell et al. (1997a)
spathulenol (7)
E. moorei 0.4 1,8-cineole (26), #-, !-, $-eudesmol Brophy unpubl.
(40 total)
var. latiuscula 1.1 elemol (6), #-, !-, $-eudesmol Brophy unpubl.
(70 total)
var. moorei 0.8 #-pinene, 1,8-cineole, eudesmol Baker and Smith
E. morrisbyi 0.9 #-pinene, 1,8-cineole (64), Boland et al. (1991)
#-terpineol, #-terpinyl acetate
1,8-cineole (67), #-terpineol (6)
E. morrisii 1.7 #-pinene, 1,8-cineole Baker and Smith
(1920)


(%)
E. muelleriana 0.9 d-#-pinene, geranyl acetate Smith (1905), Baker

(syn. and Smith (1920)
E. dextropinea)
E. multicaulis 0.8 p-cymene (6), #-, !-, $-eudesmol Brophy unpubl.
(46 total), E,E-farnesol (7)
E. myriadena 1.5 dry 1,8-cineole (71), trans-pinocarveol (9) Bignell et al. (1997e)
E. neglecta 0.81.0 1,8-cineole (68), globulol Boland et al. (1991)
E. nepeanensis 0.5 #-pinene, 1,8-cineole, Baker and Smith
[probably a sesquiterpenes (1920)
hybrid]
E. nesophila 0.6 dry #-pinene (17), globulol (68), Brophy unpubl.
spathulenol (3)
E. newbeyi tr aromadendrene (4), trans-pinocarveol Bignell et al. (1996b)
(6), globulol (10)
E. nicholii 1.72.3 1,8-cineole (84) Boland et al. (1991)
E. nigra 0.1 l-#-pinene, 1,8-cineole, Baker and Smith
(includes leptospermone (1920), Hellyer
E. phaeotricha (1968)
sensu Boland 1.01.9 #-pinene, linalool, #-, !-, $-eudesmol Boland et al. (1991)
et al. (1991))
E. nitens 1.0 #-pinene, limonene, 1,8- cineole, Hellyer (1968),
cis-ocimene, p-cymene, isoamyl Franich (1986)
isovalerate, #-terpineol,
leptospermone
0.10.6 #-pinene (17), 1,8-cineole (30), Boland et al. (1991)
sesquiterpenes
E. nitida 1.6 l-#-phellandrene, 1,8-cineole, Baker and Smith
(syn. eudesmol (mixture of isomers) (1920)
E. amygdalina 2.25.6 dry #-phellandrene (16), 1,8-cineole (14), Li et al. (1995)
var. nitida, p-cymene (13), cis- and trans-menth-2-
E. radiata en-1-ol (9 total), #-, !-, $-eudesmol
Var. D) (17 total)
1.7 #-phellandrene (11), 1,8-cineole (10), Brophy unpubl.
p-cymene (14), menth-2-en-1-ols (12
total), #-, !-, $-eudesmol (17 total)
E. normantonensis 1.2 dry #-pinene, #-terpinene, limonene, 1,8- Brophy and Lassak
cineole, !-trans-ocimene, p-cymene, (1986)
trans-pinocarveol
0.6 #-pinene (28), limonene (8), Boland et al. (1991)
1,8-cineole (57)
1.0 1,8-cineole (43), $-terpinene (23), Boland et al. (1991)
p-cymene (23)
spathulenol (11)
E. nortonii 0.7 p-cymene, globulol, spathulenol Boland et al. (1991)
E. notabilis leptospermone Hellyer (1968)
E. nova-anglica 0.52.1 d-#-pinene, aromadendrene, Baker and Smith
sesquiterpenes (1920), Unpubl.
(1961)
1.2 dry aromadendrene (22), #-, !-, Bignell et al. (1998)


(%)
eudesmol- 2.0 globulol, viridiflorol, spathulenol Boland et al. (1991)

rich form (total 15), #-, !-, $-eudesmol)
(total 50)
nerolidol- 2.7 nerolidol (78), globulol (10) Boland et al. (1991)
rich form
aromadendrene- 1.02.2 aromadendrene (40), globulol (30) Boland et al. (1991)
rich form
E. nutans 0.9 dry #-pinene (10), 1,8-cineole (14), Bignell et al. (1996d)
aromadendrene (12),
E. obliqua 0.7 l-#-phellandrene, 1,8-cineole, Baker and Smith
p-cymene, aldehydes (1920)
3.8 !-phellandrene, p-cymene, piperitone Boland et al. (1991)
2.25.4 dry !-phellandrene (7), p-cymene (20), Li et al. (1995)
(16 total), piperitone (17)
tr piperitone (15), bicyclogermacrene Bignell et al. (1997b)
E. oblonga 0.21.7 1,8-cineole, eudesmol (mixture of Baker and Smith
(syn. isomers), leptospermone, agglomerone, (1920), Hellyer
E. sparsifolia) tasmanone (1968)
1.8 p-cymene (15), #-, !-, $-eudesmol Brophy unpubl.
(60 total)
E. obtusiflora 01.3 1,8-cineole Lassak and Southwell
(1982), Boland
et al. (1991)
spathulenol (10)
E. occidentalis 1.0 d-#-pinene, 1,8-cineole, aldehydes Baker and Smith
(1920)
var. 1.4 dry #-pinene (19), !-caryophyllene (6), Bignell et al. (1996e)
occidentalis bicyclogermacrene (29)
E. ochrophloia 4.3 dry #- and !-pinene, limonene, 1,8-cineole, Brophy and Lassak
p-cymene, #-terpineol, citronellol, (1986)
globulol, #-, !-, $-eudesmol
0.1 dry verbenone (9), globulol (5), Bignell et al. (1995c)
spathulenol (6)
E. odorata 1.9 1,8-cineole, aldehydes Baker and Smith
(1920)
#-pinene, 1,8-cineole (83), Carmo and Frazo
p-cymene (1985)
cryptone (9)
E. oldfieldii 2.9 dry #-pinene (24), 1,8-cineole (34), Bignell et al. (1994c)
p-cymene (12)
E. oleosa 1.12.1 #-pinene, 1,8-cineole, Baker and Smith
(syn. E. oleosa aromadendrene, (1920), Marshall and
var. obtusa) geraniol, aldehydes Watson (1936/37)
4.6 dry #-pinene (25), limonene (4), Bignell et al. (1995b)
1,8-cineole (52)
E. olida 2.06.0 E-methyl cinnamate (98), !-trans- Curtis et al. (1990),
ocimene (2) Smale et al. (2000)


(%)
E. olsenii 1.82.2 1,8-cineole (29), p-cymene (25), Brophy unpubl.

menth-2-en-ols (17 total), #-, !-,
E. orbifolia 1.7 dry isovaleraldehyde, limonene, Brophy and Lassak
1,8-cineole, p-cymene (1986)
tr #-pinene (7), 1,8-cineole (66), Bignell et al. (1996c)
#-terpineol (6)
E. oreades 1.2 l-#-phellandrene, eudesmol Baker and Smith
(mixture of isomers), sesquiterpenes (1920)
0.40.5 !-phellandrene, 1,8-cineole, Boland et al. (1991)
p-cymene, piperitone, #-, !-,
$-eudesmol
E. orgadophila 0.20.8 #- and !-pinene, !-phellandrene, Boland et al. (1991)
#-terpineol, sesquiterpenes
E. ornata 0.5 dry #-pinene (12), 1,8-cineole (21), Bignell et al. (1997d)
pinocarveol (17)
E. orophila limonene (8), 1,8-cineole (16), Pryor et al. (1995)
terpinyl acetate (22)
E. ovata 0.21.3 dry #- and !-pinene, myrcene, Baker and Smith
(syn. E. paludosa; #- phellandrene, #-terpinene, (1920), Unpubl.
E. acervula limonene, 1,8-cineole, p-cymene, (1961), Brooker
of some terpinolene, linalool, terpinen-4-ol, and Lassak (1981)
authors) #-terpineol, piperitone, geraniol,
cuminal, globulol, viridiflorol,
eudesmol (mixture of isomers)
linalool (13), nerolidol (6)
tr dry terpinen-4-ol (28), globulol (12) Bignell et al. (1998)
E. ovularis 1.0 dry #-pinene (11), 1,8-cineole (45), Bignell et al. (1997e)
E. oxymitra 0.3 dry #-pinene (16), 1,8-cineole (46), Bignell et al. (1994c)
E. pachycalyx 0.61.0 #-pinene, 1,8-cineole Boland et al. (1991)
E. pachyloma 0.7 dry #-pinene (10), 1,8-cineole (53) Bignell et al. (1997b)
E. pachyphylla 0.6 dry #-pinene, limonene, 1,8-cineole, Brophy and Lassak
$-terpinene, !-trans-ocimene, (1986)
p-cymene, trans-pinocarveol,
0.3 dry #-pinene (5), 1,8-cineole Bignell et al. (1994c)
(59), aromadendrene (7)
E. paliformis 2.9 #-phellandrene, 1,8-cineole, Lassak and Southwell
p-cymene, cis- and trans-p-menth- (1982)
2-en-1-ol, terpinen-4-ol, cis- and
trans-piperitol, piperitone
0.6 p-cymene (30), menth-2-en-1-ols Brophy unpubl.
(12 total), piperitone (30)
E. paludicola 0.1 #-pinene, 1,8-cineole, esters, Baker and Smith
alcohols (1920)
0.2 #-pinene (5), 1,8-cineole (44), Ndou et al. (1985)
p-cymene (6), piperitone (6)


(%)
0.2 dry 1,8-cineole (29), aromadendrene Bignell et al. (1996g)

(12), #-terpineol (10)
E. papuana 0.30.7 dry papuanone (70) Boland and Brophy
(1993)
E. papuana s. lat. 0.0 Brophy unpubl.
E. papuana tr aromadendrene (60), Brophy unpubl.
vel aff. bicyclogermacrene
E. paracolpica 0.1 dry #-pinene (20), !-pinene (6), Brophy unpubl.
limonene (19), globulol (4)
E. parramattensis 0.6 #-pinene, 1,8-cineole, aldehydes Baker and Smith
(1920)
1.0 dry 1,8-cineole (72), aromadendrene (6) Bignell et al. (1996a)
E. parvifolia #-pinene, 1,8-cineole, eudesmols Baker and Smith
(mixture of isomers), aldehydes (1920)
1.3 1,8-cineole (81), #-terpineol Boland et al. (1991)
E. patellaris 0.3 dry 1,8-cineole (22), aromadendrene (33), Bignell et al. (1997a)
verbenone (10)
E. patens tr limonene (31), 1,8-cineole (7), Bignell et al. (1997b)
torquatone (8)
E. pauciflora 0.61.5 l-#-pinene, l-#-phellandrene, 1,8- Baker and Smith
(syn. cineole, piperitone, eudesmol (1920)
E. coriacea, (mixture of isomers), may exist
E. phlebophylla) in chemical varieties
myrcene, 1,8-cineole, elemol Yatagai and Takashi
(1983)
1.83.4 dry #-pinene (11), #-phellandrene (6), Li et al. (1995)
1,8- cineole (9), #-, !-, $-eudesmol
(40 total)
0.62.7 spathulenol (4), #-, !-, $-eudesmol Brophy unpubl.
(71 total)
subsp. 2.1 #-, !-, $-eudesmol (60 total), Brophy unpubl.
debeuzevillei elemol (16)
subsp. 1.4 dry cis- and trans-menth-2-en-1-ol Bignell et al. (1998)
niphophila (30 total), trans-piperitol (20)
(syn. 0.4 piperitone (6), elemol (9), #-, !-, Brophy unpubl.
E. niphophila) $-eudesmol (55)
subsp. pauciflora 0.5 dry piperitone (14), #-, !-, $-eudesmol Bignell et al. (1998)
(42 total)
E. peeneri 5.8 dry #-pinene (21), !-pinene (6), Bignell et al. (1995b)
1,8-cineole (32)
E. pellita 0.1 #-pinene, 1,8-cineole, globulol Boland et al. (1991)
0.1 dry 1,8-cineole (25), trans-pinocarveol Bignell et al. (1997f )
(14), #-, !-, $-eudesmol (10 total)
0.3 #-pinene (77), globulol (3) Brophy et al. (1998b)
E. pendens tr bicyclogermacrene (22), spathulenol Bignell et al. (1997b)
(8), torquatone (6)


(%)
E. perangusta tr 1,8-cineole (17), bicyclogermacrene Bignell et al. (1997d)

E. percostata 3.9 dry #-pinene (12), p-cymene (12), Bignell et al. (1995a)
spathulenol (14)
E. perriniana 1.1 #-pinene, 1,8-cineole, butyl Baker and Smith
butyrate, aldehydes (1920)
2.8 dry 1,8-cineole (86) Boland et al. (1991)
3.2 dry #-pinene (11), limonene (5), Li et al. (1996)
1,8-cineole (66), #-terpineol (2)
E. petalophylla 0.31.0 #-pinene (24), $-terpinene (9), Brophy et al. (1998b)
E. petraea 0.7 dry #-pinene (11), 1,8-cineole (57) Bignell et al. (1997a)
E. phaenophylla 1.7 dry #-pinene (8), 1,8-cineole (7), Bignell et al. (1997c)
aromadendrene (7),
spathulenol (15)
subsp. 0.4 dry #-pinene (8), p-cymene (15), Bignell et al. (1997g)
interjacens spathulenol (30)
E. phenax 0.70.8 d-#-pinene, 1,8-cineole Berry and Swanson
(syn. E. anceps) (1942)
aromadendrene (18),
E. pileata 3.7 dry #-pinene (24), 1,8-cineole (20), Bignell et al. (1995a)
sp. aff. pileata 2.1 dry #-pinene (26), 1,8-cineole (29), Bignell et al. (1997e)
aromadendrene (12)
E. pilularis 0.1 d-#-pinene, l-#-phellandrene, 1,8- Baker and Smith
cineole, eudesmol (mixture of (1920)
isomers), sesquiterpenes
0.50.8 #-phellandrene (8), p-cymene (30), Brophy unpubl.
spathulenol (6),
isobicyclogermacrene (15)
E. pimpiniana 1.9 dry #-pinene (39), 1,8-cineole (18), Bignell et al. (1994b)
aromadendrene (7)
E. piperita
Var. A 0.8 #-pinene, #-phellandrene, Baker and Smith
1,8-cineole, piperitone (5), (1920), Penfold and
eudesmol (mixture of isomers) Morrison (1924)
Type 2.3 l-#-phellandrene, l-piperitone Penfold and Morrison
(4050) (1924)
subsp. piperita 1.5 #-phellandrene (8), 1,8-cineole Brophy unpubl.
(25), #-, !-, $-eudesmol
(20 total)
subsp. urceolaris 0.6 #-phellandrene (18), 1,8-cineole Brophy unpubl.
(23), p-cymene (17), terpinen-4-ol
(6), #-, !-, $-eudesmol (10 total)
E. planchoniana tr #-phellandrene, sesquiterpenes Baker and Smith
(1920)
tr-0.3 1,8-cineole (47), spathulenol (5), Brophy unpubl.


(%)
E. platycorys 4.0 dry #-pinene (20), 1,8-cineole (44), Bignell et al. (1996b)
!-eudesmol (4)
E. platyphylla 0.60.8 #-pinene (75), limonene (11) Boland et al. (1991)
E. platypus 0.8 d-#-pinene, 1,8-cineole, aldehydes, Baker and Smith
var. heterophylla 0.61.2 #-pinene (36), 1,8-cineole (15), Brophy unpubl.
aromadendrene (19),
var. platypus 2.1 dry #-pinene (15), 1,8-cineole (24), Bignell et al. (1996d)
aromadendrene (11),
E. pluricaulis
subsp. 0.3 dry 1,8-cineole (28), !-caryophyllene (8), Bignell et al. (1997c)
pluricaulis aromadendrene, bicyclogermacrene
(8), isobicyclogermacral (5)
subsp. porphyrea 2.5 dry #-pinene (33), 1,8-cineole (21), Bignell et al. (1997c)
E. polyanthemos 0.30.8 #-pinene, l-#-phellandrene, Baker and Smith
(syn. E. ovalifolia, 1,8-cineole, sesquiterpenes (1920)
E. ovalifolia var. 0.82.6 dry 1,8-cineole (60), viridiflorene, Boland et al. (1991)
lanceolata) globulol
E. polybractea 1.22.5 1,8-cineole, p-cymene, cuminal, Baker and Smith
(syn. phellandral, cryptone (1920)
E. fruticetorum) 0.75.0 1,8-cineole (92) Boland et al. (1991)
E. populnea 0.8 #-pinene, 1,8-cineole, sesquiterpenes Baker and Smith
(syn. (1920)
E. populifolia) 0.4 dry 1,8-cineole (61), aromadendrene (13), Bignell et al. (1995c)
alloaromadendrene (3)
E. porosa 2.1 dry #-pinene (10), 1,8-cineole (17), Bignell et al. (1995c)
p-cymene (12)
E. praetermissa 0.8 dry #-pinene (27), 1,8-cineole (34), Bignell et al. (1997c)
E. preissiana 0.6 dry 1,8-cineole (54), #-, !-, $-eudesmol Bignell et al. (1997b)
(12 total)
subsp. lobata 0.3 dry 1,8-cineole (38), viridiflorene (10) Bignell et al. (1997g)
E. propinqua 0.3 #-pinene, 1,8-cineole, aldehydes Baker and Smith
(1920)
1.01.8 #-pinene, 1,8-cineole, monoterpene Boland et al. (1991)
alcohols
E. sp. aff. 1.31.7 #-pinene, 1,8-cineole, p-cymene Boland et al. (1991)
propinqua
E. pruiniramis 3.1 dry #-pinene (23), 1,8-cineole (35), Bignell et al. (1997g)
aromadendrene (14)
E. pruinosa tr0.4 bicyclogermacrene, '-cadinene, Boland et al. (1991)
globulol, spathulenol
tr 1,8-cineole (63), trans-pinocarveol Bignell et al. (1997a)
(5), carvone (9)
E. pterocarpa 2.5 dry #-pinene (14), 1,8-cineole (17), Bignell et al. (1995a)
aromadendrene (27)


(%)
E. pulchella 1.11.5 l-#-phellandrene, 1,8-cineole, Baker and Smith

(syn. E. linearis) piperitone, eudesmol (mixture of (1920)
isomers)
4.25.6 dry #-phellandrene (6), 1,8-cineole (47), Li et al. (1995)
aromatics (8)
2.7 1,8-cineole (46), apodophyllone (18) Brophy unpubl.
E. pulverulenta 2.24.8 dry isovaleraldehyde, #-pinene, limonene, Baker and Smith
1,8-cineole, #-terpineol, #-terpinyl (1920), Brophy et al.
acetate (1985), Boland
et al. (1991)
E. pumila 1.6 d-#-pinene, 1,8-cineole, aldehydes Baker and Smith
(1920)
0.5 dry 1,8-cineole (72) Bignell et al. (1998)
E. punctata 0.22.3 #- and !-pinene, myrcene, #-terpinene, Baker and Smith
limonene, 1,8-cineole, p-cymene, (1920), Southwell
menthyl acetate, terpinen-4-ol, (1973)
cryptone, #-terpineol, geraniol,
cuminal, phellandral
E. pyriformis 1.01.1 d-#-pinene, 1,8-cineole, Marshall and Watson
aromadendrene, eudesmol (1937/38)
(mixture of isomers), aldehydes
aromadendrene (5)
E. quadrangulata 0.7 d-#-pinene, 1,8-cineole Baker and Smith
(1920)
cineole-rich 1.62.1 #-pinene (25), 1,8-cineole (55) Boland et al. (1991)
form
$-terpinene- 1.2 #-pinene, 1,8-cineole (25), $-terpinene Boland et al. (1991)
rich form (19), p-cymene, globulol
eudesmol- 1.5 p-cymene (33), #-, !-, $-eudesmol Boland et al. (1991)
E. quadrans 0.8 dry 1,8-cineole (43), trans-pinocarveol (20) Bignell et al. (1997e)
E. quadricostata 0.30.5 #-pinene (21), !-pinene (15), Brophy unpubl.
1,8-cineole (10), #-terpineol (11),
globulol (5)
E. radiata 6.3 dry #-phellandrene (26), 1,8-cineole (12), Li et al. (1995)
(12 total), terpinen-4-ol (4),
piperitone (10)
subsp. radiata
Type (syn. 3.03.5 #-pinene, 1,8-cineole, #-terpineol, Baker and Smith
E. australiana, geraniol, citral (1920), Penfold and
E. radiata Morrison (1935)
var. australiana) 1.72.0 dry 1,8-cineole (70) Boland et al. (1991)
1.52.3 #-terpinene, #-phellandrene, Penfold and Morrison
$-terpinene, terpinen-4-ol (1935)
Var. B 3.04.5 l-#-phellandrene, 1,8-cineole, Baker and Smith
(syn. terpineol, citral (1920), Penfold and
E. phellandra) Morrison (1935)
Var. C 0.43.9 l-#-phellandrene, p-cymene, Penfold and Morrison
(syn. l-piperitone, l-piperitol (1940)
E. australiana
Var. C)


(%)
subsp. radiata 0.4 dry 1,8-cineole (65) Bignell et al. (1998)

3.4 dry #-phellandrene (8), $-terpinene Bignell et al. (1998)
(12), terpinen-4-ol (25)
subsp. sejuncta 0.30.8 #-pinene (80) Brophy unpubl.
E. rariflora 2.02.9 dry l-#- and !-pinene, car-4-ene, Penfold et al. (1930)
[hybrid, #-phellandrene, 1,8-cineole,
E. crebra ) p-cymene, aromadendrene,
E. populnea] dehydroangustione
E. raveretiana tr-0.1 #-pinene (84), campholenic aldehyde Boland et al. (1991)
E. ravida 1.6 dry #-pinene (14), 1,8-cineole (35), Bignell et al. (1996d)
(syn. E. salubris torquatone (8)
var. glauca) #-pinene, 1,8-cineole, trans- Brophy and Lassak
pinocarveol, !-eudesmol, torquatone unpubl.
E. recta tr dry #-pinene (11), 1,8-cineole (15), Bignell et al. (1998)
trans-pinocarveol (8),
E. redacta 0.5 dry 1,8-cineole (43), trans-pinocarveol Bignell et al. (1997g)
(11), bicyclogermacrene (6)
E. redunca 1.2 #-pinene, 1,8-cineole, sesquiterpenes Baker and Smith
(1920)
aromadendrene (6),
E. regnans 0.8 l-#-phellandrene, eudesmol (mixture Baker and Smith
of isomers) (1920)
3.2 dry #-phellandrene, p-cymene, cis- and Boland et al. (1991)
trans-menth-2-en-1-ol, elemol, #-,
!-, $-eudesmol
3.05.8 dry #-phellandrene (6), p-cymene (5), #-, Li et al. (1995)
!-, $-eudesmol (43 total),
aromatics (7)
E. remota 0.72.0 eudesmol (mixture of isomers) Unpubl. (1961)
tr #-, !-, $-eudesmol (50 total), Bignell et al. (1997b)
E. resinifera 0.4 #-pinene, 1,8-cineole, valeraldehyde, Baker and Smith
(syn. sesquiterpenes (1920)
E. hemilampra) 0.7 1,8-cineole (72) Martnez et al. (1986)
tr 1,8-cineole (13), trans-pinocarveol Bignell et al. (1997f )
E. rhodantha 0.9 dry #-pinene (28), 1,8-cineole (33), Bignell et al. (1994c)
E. rhombica 0.30.5 1,8-cineole (34), globulol (15), Brophy unpubl.
spathulenol (5)
E. rigens 2.0 dry 1,8-cineole (69), trans-pinocarveol (11) Bignell et al. (1997e)
E. rigidula 3.3 dry #-pinene (25), 1,8-cineole (7), Bignell et al. (1997d)
aromadendrene (19),
E. risdonii 1.4 l-#-phellandrene, 1,8-cineole, Baker and Smith
amyl acetate (1920)
1.32.3 dry 1,8-cineole (60), #-terpineol (6), Li et al. (1995)
#-terpinyl acetate (6)


(%)
0.3 1,8-cineole (61), #-terpineol % Brophy unpubl.

terpinyl acetate (15 total)
E. robertsonii 1.3 dry 1,8-cineole (61), #-terpineol (15) Bignell et al. (1998)
(syn. 1.4 1,8-cineole (65), linalool (5), Brophy unpubl.
E. radiata #-terpineol (13)
subsp.
robertsonii)
E. robusta 0.2 #-pinene, #-phellandrene, Baker and Smith
1.7 1,8-cineole, p-cymene, linalool, Dayal and Maheshwari
terpinen-4-ol, #-terpineol, (1985)
piperitone, citronellyl acetate
tr #-pinene (13), trans-pinocarveol (27) Bignell et al. (1997f)
E. rodwayi 0.5 #-pinene, 1,8-cineole Baker and Smith
(1920)
cineole-rich 2.33.3 dry #-pinene (18), 1,8-cineole (60), Li et al. (1996)
form #-terpineol (3)
phellandrene- 2.1 #-phellandrene (43), 1,8-cineole (10), Boland et al. (1991)
rich form p-cymene (8), globulol (9)
E. rossii 0.6 #-pinene, 1,8-cineole, eudesmol Baker and Smith
1.6 1,8-cineole (34), #-, !-, $-eudesmol Brophy unpubl.
(34 total)
E. rubida 0.1 #-pinene, #-phellandrene, 1,8-cineole, Baker and Smith
0.61.1 p-cymene, spathulenol (36) Boland et al. (1991)
#-terpineol (6), spathulenol (6)
E. rubiginosa 0.2 #-pinene (47), !-pinene (23) Brophy et al. (1998a)
E. rudderi 0.3 p-cymene, aldehydes Baker and Smith
(1920)
E. rudis 1.2 d-#-pinene, 1,8-cineole, aldehydes Baker and Smith
(1920)
0.7 dry #-phellandrene (3), alloaromadendrene Bignell et al. (1996a)
E. rugosa 0.9 dry #-pinene (9), 1,8-cineole (31), Bignell et al. (1994b)
aromadendrene (9)
E. saligna 0.1 #-pinene, p-cymene Baker and Smith
(1920)
0.30.5 #-pinene (73), campholenic aldehyde, Boland et al. (1991)
#-terpineol
E. salmonophloia 1.43.6 #-pinene, 1,8-cineole, aromadendrene Watson (1935/36)
1.6 piperitone (42) Martnez et al. (1986)
2.7 dry 1,8-cineole (10), p-cymene (17), Bignell et al. (1996e)
cryptone (11)
E. salubris 1.4 #-pinene, 1,8-cineole, p-cymene, Baker and Smith
aldehydes (1920)
aromadendrene (5)
#-pinene, 1,8-cineole, p-cymene, Brophy and Lassak
pinocarvone, trans-pinocarveol unpubl.


(%)
E. sargentii subsp. 1.6 dry #-pinene (12), 1,8-cineole (49), trans- Bignell et al. (1996e)
sargentii pinocarveol (5)
E. saxatilis 3.55.1 dry 1,8-cineole (71), sesquiterpenes Boland et al. (1991)
E. scabrida 0.3 #-pinene (23), globulol (7), guaiol Brophy et al. (1998b)
(11), #-, !-, $-eudesmol (8 total)
E. scias 0.21.8 #-pinene (18), 1,8-cineole (43), Doran et al. (1995)
#-terpineol (12)
E. sclerophylla 0.7 1,8-cineole (14), globulol (15), Brophy unpubl.
viridiflorol (7), spathulenol (28)
E. scoparia 1.21.5 #-pinene, 1,8-cineole (71), globulol Boland et al. (1991)
E. scyphocalyx 2.9 dry #-pinene (30), 1,8-cineole (38), Bignell et al. (1996b)
aromadendrene (10)
E. seeana 0.8 #-pinene, 1,8-cineole Baker and Smith
(1920)
palustrol (9)
E. semiglobosa tr #-pinene (36), 1,8-cineole (21), Bignell et al. (1997d)
aromadendrene (6),
E. semota 0.8 dry 1,8-cineole (61), p-cymene (3) Bignell et al. (1997g)
E. sepulcralis 0.4 dry #-pinene (8), 1,8-cineole (62), Bignell et al. (1997b)
#-terpineol (5)
E. serpentinicola 1.5 1,8-cineole (37), #-, !-, $-eudesmol Brophy unpubl.
(34 total)
E. sessilis 2.0 dry #-pinene (12), 1,8-cineole (61), Bignell et al. (1994c)
aromadendrene (5)
E. setosa tr-0.1 dry aromadendrene (13), globulol (40), Brophy unpubl.
!-eudesmol (5)
E. sheathiana 4.6 dry #-pinene (15), limonene (4), Bignell et al. (1995a)
1,8-cineole (57)
E. shirleyi 0.60.7 #- and !-pinene, bicyclogermacrene, Boland et al. (1991)
'-cadinene, globulol
E. siderophloia 0.1 pinene, phellandrene Baker and Smith
(1920)
0.2 #-pinene (66), #-phellandrene, trans- Boland et al. (1987)
pinocarveol, #-terpineol
E. sideroxylon 1.52.5 #-pinene, 1,8-cineole, sesquiterpenes Baker and Smith
(1920)
2.63.2 1,8-cineole, #-terpinyl acetate, Boland et al. (1991)
globulol, #-, !-, $-eudesmol
E. sieberi 0.5 l-#-phellandrene, 1,8-cineole, Baker and Smith
(syn. piperitone (1920)
E. sieberiana) 0.4 !-pinene (24), car-3-ene (15), Arora et al. (1971)
!-phellandrene (28), 1,8-cineole (14)
3.33.9 dry #-phellandrene (7), !-phellandrene Li et al. (1995)
(6), 1,8-cineole (8), #-, !-,
1.01.3 1,8-cineole (26), p-cymene (27), #-, Brophy unpubl.


(%)
E. signata 0.01.1 !-phellandrene (26), p-cymene (19), Brophy unpubl.

#-terpineol (12), spathulenol (7)
E. smithii 1.12.2 isovaleraldehyde, #-pinene, 1,8-cineole, Baker and Smith
eudesmol (mixture of isomers) (1920), Mus. A.
and S. unpubl.
2.43.0 #-pinene, 1,8-cineole (81), globulol, Boland et al. (1991)
!-eudesmol
0.7 dry 1,8-cineole (78) Bignell et al. (1998)
E. socialis 1.0 dry #-pinene (25), 1,8-cineole (41), trans- Bignell et al. (1995b)
pinocarveol (7)
2.2 dry #-pinene (9), !-pinene (13), p-cymene Bignell et al. (1996g)
E. sparsa 2.6 dry #-pinene, limonene, 1,8-cineole, Brophy and Lassak
p-cymene (1986)
E. spathulata 1.4 d-#-pinene, 1,8-cineole, Phillips (1923)
aromadendrene, aldehydes
subsp. grandiflora 1.3 dry #-pinene (33), 1,8-cineole (38), Bignell et al. (1996d)
aromadendrene (3)
subsp. spathulata 2.1 dry #-pinene (20), 1,8-cineole (44), Bignell et al. (1996d)
aromadendrene (9)
E. sphaerocarpa 1.31.4 #-phellandrene, 1,8-cineole, p-cymene Boland et al. (1991)
E. squamosa 0.7 isovaleraldehyde, #-pinene, Baker and Smith
1,8-cineole (1920), Mus. A.
and S. unpubl.
E. staeri tr calamenene (5), globulol (4), Bignell et al. (1997b)
spathulenol (14), torquatone (7)
E. staigeriana 1.21.5 l-limonene, citral, geranyl acetate, Baker and Smith
geraniol, sesquiterpenes (1920)
2.93.4 limonene, !-phellandrene, methyl Boland et al. (1991)
geranate, geranial, geranyl acetate
2.3 dry 1,8-cineole (24), terpinolene (10), Bignell et al. (1997a)
'-terpineol (12), methyl geranate (7),
geranial (19), geraniol (7)
E. stannicola 0.10.5 spathulenol (10), #-, !-, $-eudesmol Brophy unpubl.
(60 total)
E. steedmanii 1.2 dry #-pinene (21), 1,8-cineole (32), Bignell et al. (1996d)
aromadendrene (15)
E. stellulata 0.3 l-#-phellandrene, 1,8-cineole, Baker and Smith
0.61.1 !-phellandrene (12), p-cymene (27), Brophy unpubl.
E. stenostoma 1.72.4 #-pinene, #- and !-phellandrene, Lassak and Southwell
#-terpinene, 1,8-cineole, p-cymene, (1982)
cis- and trans-p-menth-2-en-1-ol,
terpinen-4-ol, cis- and trans-piperitol,
#-terpineol, eudesmol (all three isomers)
0.5 p-cymene (29), piperitone (38) Brophy unpubl.
E. stoatei 2.6 dry #-pinene (13), 1,8-cineole (34), Bignell et al. (1994a)
aromadendrene (12)


(%)
E. stowardii 1.4 dry #-pinene (47), 1,8-cineole (19) Bignell et al. (1996e)
E. striaticalyx 4.4 dry #-pinene (29), 1,8-cineole (25), Bignell et al. (1995a)
!-eudesmol (4)
subsp. beadellii 0.7 dry #-pinene (15), 1,8-cineole (16), Bignell et al. (1997e)
pinocarveol (22)
subsp. canescens 3.7 dry #-pinene (13), 1,8-cineole (13), Bignell et al. (1997e)
aromadendrene (30), globulol (7),
spathulenol (8)
subsp. gypsophila 0.8 dry 1,8-cineole (56), trans-pinocarveol Bignell et al. (1997e)
(17), !-eudesmol (8)
subsp. 1.7 dry 1,8-cineole (78), p-cymene (5) Bignell et al. (1997e)
striaticalyx
E. stricklandii 2.8 dry #-pinene (20), 1,8-cineole (14), Bignell et al. (1996c)
torquatone (21)
#-pinene, 1,8-cineole, torquatone, Brophy and Lassak
sesquiterpene alcohols unpubl.
E. stricta 0.5 #-pinene, 1,8-cineole, piperitone, Baker and Smith
eudesmol (mixture of isomers), (1920), Mus. A.
aldehydes and S. unpubl.
E. sturgissiana 1.12.5 1,8-cineole (90) Boland et al. (1991)
E. subangusta
subsp. cerina 3.1 dry #-pinene (9), #-phellandrene (16), Bignell et al. (1997g)
1,8-cineole (6), !-caryophyllene
subsp. pusilla 1.3 dry #-pinene (18), 1,8-cineole (57), Bignell et al. (1997g)
!-eudesmol (6)
subsp. 3.3 dry #-pinene (27), 1,8-cineole (35), Bignell et al. (1997g)
subangusta bicyclogermacrene (8)
E. subcrenulata 2.5 4.6 dry #-pinene, 1,8-cineole (62), Boland et al. (1991)
#-terpineol
1.1 4.1 dry #-pinene (15), 1,8-cineole (48), Li et al. (1996)
E. suberea 1.4 dry tasmanone (94) Bignell et al. (1997b)
E. sublucida 1.9 dry #-pinene (31), 1,8-cineole (16), Bignell et al. (1996g)
E. subtilior 0.6 1,8-cineole (58), #-, !-, Brophy unpubl.
E. subtilis 2.7 dry #-pinene (7), 1,8-cineole (58), Bignell et al. (1997c)
aromadendrene (9)
E. suffulgens 0.30.9 #-pinene (20), !-pinene (38), Brophy unpubl.
#-terpineol (12), #-, !-,
E. suggrandis 1.1 dry #-pinene (27), 1,8-cineole (26), Bignell et al. (1998)
carvone (19)
E. synandra 2.4 dry #-pinene (16), !-pinene (2), Bignell et al. (1994c)
1,8-cineole (71)
E. taeniola 0.7 l-#-phellandrene, eudesmol Baker and Smith
[hybrid, (mixture of isomers), (1920)
E. amygdalina ) sesquiterpenes
E. sieberi]
E. talyuberlup tr #-pinene (39), limonene (4), Bignell et al. (1996b)
p-cymene (6)


(%)
E. tectifica 0.41.0 1,8-cineole (65), p-cymene, Boland et al. (1991)

aromadendrene
E. tenera 1.8 dry 1,8-cineole (62), trans-pinocarveol Bignell et al. (1998)
(11)
E. tenuipes 0.4 #-pinene (5), !-pinene (31), Brophy et al. (1998a)
#-terpineol (11), globulol (5)
E. tenuiramis 3.15.7 dry #-phellandrene (11), 1,8-cineole Li et al. (1995)
(35), cis- and trans-menth-
2-en-1-ol (10 total)
E. tenuis 1.3 dry #-pinene (15), 1,8-cineole (24), Bignell et al. (1995a)
p-cymene (21), trans-
pinocarveol (11)
E. terebra 0.6 dry #-pinene (12), 1,8-cineole (45), Bignell et al. (1996d)
E. tereticornis 0.50.9 #-pinene, phellandrene, 1,8-cineole, Baker and Smith
(var. cineolifera p-cymene, cuminal (1920), Shiva
is a cineole- et al. (1984)
rich form) 0.91.4 #- and !-pinene, 1,8-cineole, Boland et al. (1991)
spathulenol, #-, !-, $-eudesmol,
globulol
0.6 dry p-cymene (28), cryptone (15), Bignell et al. (1996a)
caryophyllene oxide (9)
E. tessellaris 0.2 #-pinene, 1,8-cineole, aromadendrene Baker and Smith
(1920)
tr-0.1 !-pinene, limonene, spathulenol Boland et al. (1991)
tr #-pinene (5), aromadendrene (10), Bignell et al. (1997f)
globulol (5), torquatone (5)
E. tetragona 0.5 dry d-#-pinene, l-#-phellandrene, Watson (1935/36)
1,8-cineole
0.1 dry aromadendrene (13), Bignell et al. (1996f)
bicyclogermacrene (11), #-, !-,
0.40.6 #-pinene (13), globulol (12), #-, Brophy unpubl.
E. tetraptera 2.1 dry #-pinene (21), 1,8-cineole (24), Bignell et al. (1994a)
aromadendrene (13)
globulol (7), #-, !-, $-eudesmol
(5 total)
E. tetrodonta 0.2 #-pinene (55), #-terpineol (9), Brophy unpubl.
globulol (3)
E. thozetiana tr 1,8-cineole (21), verbenone (7), Bignell et al. (1997a)
torquatone (3)
E. tindaliae 0.2 #-pinene (35), #-, !-, Brophy unpubl.
E. tinghaensis 0.40.9 Unpubl. (1961)
[hybrid,
E. caliginosa )
E. mckieana]
E. tintinnans 0.1 dry #-pinene (64), limonene (5), Bignell et al. (1997f )
E. todtiana tr !-pinene (11), 1,8-cineole (9), Bignell et al. (1997b)
viridiflorene (8)


(%)
tr-0.1 1,8-cineole (36), globulol (6), Brophy unpubl.

spathulenol (11), #-, !-,
E. torelliana 0.3 #- and !-pinene, p-cymene, Webb et al. (1956)
ocimene, aromadendrene
0.3 dry #-pinene (54), !-phellandrene Brophy unpubl.
(9), !-caryophyllene (8)
E. torquata #-pinene, 1,8-cineole, eudesmol Bowyer and Jefferies
(mixture of isomers), torquatone (1959)
3.6 dry #-pinene (19), !-eudesmol (10), Bignell et al. (1994b)
torquatone (41)
E. trachyphloia 0.2 d-#-pinene, aromadendrene, Baker and Smith
aldehydes (1920)
0.2 dry bicyclogermacrene (54), globulol (8) Bignell et al. (1997f )
E. transconti- 3.9 dry #-pinene (26), 1,8-cineole (47), Bignell et al. (1995b)
nentalis aromadendrene (7)
(syn. E. oleosa
var. glauca)
E. triflora 0.70.8 #-pinene, #- and !-phellandrene, Lassak and Southwell
p-cymene, cis- and trans-p-menth- (1982)
2-en-1-ol, terpinen-4-ol, cis- and
trans-piperitol, piperitone
0.30.5 !-pinene (6), p-cymene (29), cis- and Brophy unpubl.
trans-menth-2-en-1-ol (12 total),
piperitone (29)
E. trivalvis 1.0 dry #-pinene (10), 1,8-cineole (52), Bignell et al. (1997g)
aromadendrene (5)
E. tumida 0.6 dry #-pinene (31), 1,8-cineole (20), Bignell et al. (1997c)
aromadendrene (10)
E. umbonata tr #-, !-, $-eudesmol (20 total), Bignell et al. (1997f)
torquatone (37)
E. umbra 0.6 d-#-pinene, 1,8-cineole, Baker and Smith
0.7 #-pinene, 1,4-cineole, 1,8-cineole Miranda et al. (1981)
1.5 #-pinene (37), 1,8-cineole (30) Brophy unpubl.
subsp. carnea 0.2 d-#-pinene, 1,8-cineole, terpinyl Baker and Smith
(syn. E. carnea) acetate (1920)
E. umbrawarrensis 0.40.6 #-pinene, !-pinene (41), #-terpineol, Boland et al. (1991)
globulol, spathulenol
E. uncinata 0.6 dry 1,8-cineole (47), pinocarvone (8), Bignell et al. (1997d)
pinocarveol (21)
E. unialata 0.9 d-#-pinene, 1,8-cineole, Baker and Smith
E. globulus )
E. viminalis]
E. urnigera 1.1 d-#-pinene, 1,8-cineole Baker and Smith
(1920)
#-terpineol (3), #-terpinyl
acetate (4)
E. urophylla 0.2 #-pinene (7), p-cymene (75) Singh et al. (1988)


(%)
0.61.4 #-pinene (20), !-pinene (5), Doran et al. (1995)

1,8-cineole (40)
E. varia
salsuginosa bicyclogermacrene (31), spathulenol
(5), #-, !-, $-eudesmol (8 total)
subsp. varia 0.6 dry !-caryophyllene (9), Bignell et al. (1997c)
spathulenol (3)
E. vegrandis 1.9 dry #-pinene (35), 1,8-cineole (34) Bignell et al. (1998)
E. vernicosa 0.8 d-#-pinene, 1,8-cineole, aldehydes Baker and Smith
(1920)
#-terpineol (3)
E. vicina 1.2 dry 1,8-cineole (64), trans-pinocarveol Bignell et al. (1996a)
(9), aromadendrene (3)
E. viminalis 0.5 d-#-pinene, #-phellandrene, Baker and Smith
1.11.6 #-pinene, 1,8-cineole (64), globulol Boland et al. (1991)
1,8-cineole (50), globulol (7)
Var. A 0.8 #-pinene, 1,8-cineole, benzaldehyde, Baker and Smith
E. virens 0.10.3 #-pinene (80), bicyclogermacrene (4) Brophy unpubl.
E. virgata 0.30.6 l-#-phellandrene, 1,8-cineole, Baker and Smith
[possibly a piperitone, eudesmol (mixture of (1920)
hybrid, isomers), sesquiterpenes
E. luehmanniana )
E. obtusiflora]
E. viridis 1.5 #-pinene, 1,8-cineole Penfold and Morrison
(1951)
2.1 #- and !-pinene, 1,8-cineole (93), Ghanim and
p-cymene, cryptone, #-terpineol, Jayaraman (1978)
geraniol, isopulegol
aromadendrene (18)
E. vitrea 1.5 l-#-phellandrene, 1,8-cineole, Baker and Smith
E. pauciflora
subsp. pauciflora )
E. radiata
subsp. radiata]
E. wandoo tr #-pinene (8), 1,8-cineole (24), Bignell et al. (1997c)
$-terpinene (10), p-cymene (18)
p-cymene-rich 0.7 p-cymene (65) Brophy unpubl.
form
p-cymene-poor 1.8 1,8-cineole (28), $-terpinene (12), Brophy unpubl.
form p-cymene (10), #-, !-, $-eudesmol
(20 total)
E. watsoniana
subsp. capillata 0.10.6 #-pinene (38), bicyclogermacrene Brophy et al. (1998b)
(9), globulol (8), #-, !-, $-eudesmol
(10 total)


(%)
subsp. tr bicyclogermacrene (52), globulol (4) Bignell et al. (1997f )

watsoniana 0.10.4 #-pinene (5), !-pinene (26), Brophy et al. (1998b)
bicyclogermacrene (8), globulol (15)
E. websteriana 1.4 dry #-pinene (16), 1,8-cineole (62), Bignell et al. (1996c)
!-eudesmol (3)
E. wetarensis #-pinene (5), #-phellandrene (14), Pryor et al. (1995)
$- terpinene (15), p-cymene (20)
E. whitei 0.11.9 nerolidol (55), #-terpineol (8) Brophy unpubl.
E. wilcoxii 1.42.3 dry 1,8-cineole, $-terpinene, #-, !-, Boland et al. (1991),
$-eudesmol Boland and Kleinig
(1983)
E. williamsiana 0.61.0 #-, !-, $-eudesmol (70 total) Brophy unpubl.
E. willisii 1,8-cineole (74), #-terpineol (4), #-, Brophy and Doran
!-, $-eudesmol (4 total) unpubl.
E. woodwardii 2.6 dry #-pinene (28), 1,8-cineole (17), Bignell et al. (1995a)
aromadendrene (11), torquatone (12)
#-pinene, 1,8-cineole, #-, !-, Brophy and Lassak
$-eudesmol, torquatone unpubl.
E. wyolensis 1.4 dry #-pinene (7), 1,8-cineole (12), Bignell et al. (1996g)
spathulenol (15)
E. xanthonema 0.7 dry #-pinene (20), 1,8-cineole (15), Bignell et al. (1997c)
aromadendrene (14),
E. yalatensis tr dry #-pinene (8), !-pinene (10), Bignell et al. (1995b)
1,8-cineole (14), torquatone (4)
E. yarraensis 0.10.6 benzaldehyde Lassak and Southwell
(1977)
0.1 benzaldehyde (84), nerolidol, globulol Boland et al. (1991)
tr dry terpinen-4-ol (17), piperitone (11), Bignell et al. (1998)
spathulenol (11)
E. yilgarnensis 0.8 dry 1,8-cineole (12), p-cymene (14), Bignell et al. (1997e)
cryptone (10)
E. youmanii 1.3 #-pinene, mycrene, #-phellandrene, Brophy et al. (1982)
limonene, 1,8-cineole, p-cymene,
terpinen-4-ol, #-terpineol, #-, !-,
$-eudesmol
tr 1,8-cineole (12), alloaromadendrene Bignell et al. (1997f )
E. youngiana 3.1 dry #-pinene (25), 1,8-cineole (47), trans- Bignell et al. (1994c)
pinocarveol (3)
E. yumbarrana 1.4 dry #-pinene (29), 1,8-cineole (37), trans- Bignell et al. (1995b)
pinocarveol (8)
E. zopherophloia 1.7 dry #-pinene (9), 1,8-cineole (72) Bignell et al. (1997g)
a Based on fresh weight of leaf except where dry indicates dry weight basis.
b Figures in parentheses refer to the percentage abundance of the constituent in the oil.
c Indicates trace ((0.05%).

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6 Distillation of eucalyptus leaf oils
Theory and practice
E.F.K. Denny
Theory
The distilling operation

Several species of Eucalyptus yield oils which are valuable in commerce. The oil glands are
secreted deeply in the leaves, well below the epidermal cuticle and other cells which together
form the surface layers of the foliage. These oils can be recovered from the herb by steam distil-
lation and are then referred to as essential oils because, being the products of distillation they
are, by definition, essences.
When trees grown for timber are felled, the waste leaves and small branches may be gathered
by hand and loaded onto carts or trucks for transport to the distillery. In plantations developed
primarily for essential oil production the trees are smaller and may be harvested by relatively
harsh machinery. This usually damages the foliage and exposes some of the oil ducts, resulting in
some loss of oil by evaporation. If the harvester loads the cut material directly into a trailer
which also serves as the processing container, as is the case in Australia, any such losses are not
significant. Otherwise, unloading and rehandling of this machine-cut eucalypt may result in an
appreciable loss of oil.
At the distillery, the hand-cut material must be loaded manually and tramped down tightly
into big vats, called stills. On the other hand, the mechanically harvested foliage is received
ready packed for distillation in trailers which are specially designed to act efficiently as stills. In
both cases, a steam-tight lid, often incorporating the outlet pipe, is fitted to the top of the still.
A flow of steam, either from water boiled in the bottom of the still itself or, preferably, piped
from a separate boiler, is then introduced below the plant material so that it percolates upwards
through the charge.
Starting at the bottom, the steam condenses on all the herb surfaces and, surrendering its
latent heat, raises the temperature of successive layers to boiling point. When the appropriate
temperature reaches the top of the still, any oil that is exposed on the herb surfaces will start to
boil away. The on-coming steam will then drive a mixture of steam and oil vapour off the top of
the charge and from there it is led through a condenser. In the liquid state, the oil and water are
virtually immiscible and separate spontaneously. The oil floats on top of the water and is easily
removed for bulk storage and subsequent sale. This operation continues until, for all practical
purposes, the oil is exhausted from the herb. The spent charge is then removed from the still and
replaced by fresh plant material.
It is many centuries since aromatic herbs were first packed into vats and steam was passed
through the charge to extract the volatile oils. But despite its antiquity, certain aspects of this
hydrodistillation process have not been well understood and it is much abused. Modern equipment

has made little fundamental advance on the primitive cooking methods of the past. The princi-
ple involved in recovering the volatile oils by vaporising them in the presence of steam is well
known. But this vaporisation demands the transfer of heat from the steam to the oil and it is this
function which is gravely misunderstood. Any improvement in the efficiency and economy of
the industry depends on a better appreciation of this aspect.
Conditions for distilling the oil

For the steam to boil away any oil that is exposed on the herb surface and gather up the vapour,
certain conditions are required. Firstly, since vapours contain more heat energy per gram than
their parent liquids, the oil cannot be turned into a vapour unless heat is applied to it. If the
steam is to do this, and it is the only thing that can, it must be at a higher temperature than
the liquid oil. The amount of heat required to vaporise one gram of liquid, without raising the
vapours temperature above that of the liquid, is a characteristic of the particular compound and
is termed its latent heat of vaporisation. Conversely, if steam or any other vapour is condensed back
to liquid, its energy content is reduced and the characteristic quantity of latent heat is given out.
Secondly, the conditions for boiling depend upon certain properties of vapours. It is not
practical to discuss these in isolation from other aspects of vapour behaviour which will be
important later on and so they are now considered below.
Liquids continually emit moving vapour molecules from their surfaces. These impinge on
their surroundings and exert a characteristic vapour pressure on them. This pressure increases with
rising temperature. If a closed liquidvapour system is at a constant temperature, equal numbers
of molecules are continuously leaving the liquid surface and returning to it. In this equilibrium
condition the number of molecules present in any unit volume of the vapour space, their concen-
tration, is exactly that required to exert the vapour pressure that is characteristic of the compound
at the prevailing temperature. A vapour having this concentration and exerting this pressure is
termed a saturated vapour.
All vapours in immediate contact with their parent liquid will be saturated vapours. It
follows that if heat is applied to a vapour space or its volume is expanded, extra molecules must
vaporise from the liquid surface to maintain the saturated vapour pressure in the new conditions.
But if the vapour is no longer in contact with its liquid the extra molecules are simply not avail-
able. The pressure that can be exerted by the heated or expanded vapour will then be less than
would be exerted by a saturated vapour of the same kind, at the same temperature. Alternatively,
its temperature is higher than that of the saturated vapour exerting the same pressure. A vapour
in this condition is said to be superheated.
If a superheated vapour comes into contact with its parent liquid, the latter will instantly
evaporate to ensure that saturated equilibrium conditions are restored. Since the superheated
vapour will usually provide the heat to support this evaporation, its own temperature will be
reduced. It is very important for eucalypt distillers to understand that when superheated steam
enters moist surroundings, it will immediately take up sufficient water molecules as vapour to
revert to being saturated steam at a lower temperature.
If heat is applied to a liquid, its temperature will not rise beyond the point where its vapour
pressure becomes equal to the surrounding pressure, whatever that may be. Continued applica-
tion of heat will merely convert liquid into vapour at the rate set by the liquids requirement of
latent heat for vaporisation. The liquid is then said to boil and the temperature at which this
occurs is called the boiling point under the prevailing pressure.
A liquids vapour pressure will attain equality with a low surrounding pressure at a lower
temperature than it would require for equalising a high surrounding pressure. If a table is

prepared showing a liquids vapour pressure at different temperatures, the latter are automati-
cally the boiling points when the surrounding pressure is the same as the indicated vapour pres-
sure. Such a table will show that even a very small increase in the pressure required of a vapour
is inevitably associated with the corresponding rise in its temperature, and vice versa.
If the vapour-generating vessel is open to the atmosphere, the liquid will boil when its vapour
pressure becomes equal to the atmospheric pressure. In average conditions at sea level the pres-
sure in the atmosphere will support a column of mercury 760 mm tall, so-called standard atmos-
pheric pressure or 1 atm abs (atmosphere absolute). Alternative expressions for this standard
atmospheric pressure are 14.7 psi, 1.033 kg/cm2 or 101.3 kPa. These are examples of the many
other scales by which pressures are measured in commercial practice. But in all cases, ordinary
industrial pressure gauges show the difference between atmospheric pressure and that inside
the vessel to which they are attached. To obtain the absolute pressure, the ambient atmospheric
pressure must be added to the gauge reading.
Steam
Steam is the vapour of pure water. Reference books give tables showing the properties of dry sat-
urated steam at different temperatures. They show the total heat of steam, which is the amount
required to raise the water from 0C to boiling point under the given pressure, plus the latent
heat required to vaporise the water. It may be given in calories, joules or British thermal units
(Btu).1 Steam generated under 8 atm abs, equal to 7 atm gauge, has a total heat some
3.8 per cent greater than the same mass of steam under atmospheric pressure. So, if steam is
generated under high pressure and allowed to expand under a lower pressure as it enters an
essential oil still, the surplus heat must be accounted for.
In practice, all saturated steam carries microscopic liquid particles in the form of cloud. Only
superheated steam will carry none at all. Good commercial boilers generate steam consisting of
about 97 per cent by weight dry saturated steam and 3 per cent of liquid cloud, the so-called
wetness fraction. Assume this steam emerges from the distillery boiler under 7 atm of gauge
pressure and passes along efficiently insulated piping to the bottom of a still working at virtual
atmospheric pressure. As it expands on entering the still, this steam will give out enough heat to
vaporise all its own wetness fraction plus about 1.5 per cent of its own weight in further water
which, importantly, will be taken from the herb surfaces inside the still.
The amount of steam for distillation is stated in terms of its rate of flow in mass per minute
for each square metre of charge cross-section area traversed by the moving vapours. For
Eucalyptus, a good flow is around 3 kg/min/m2. Faster flows process more herb per hour and con-
sume more steam per kg of oil recovered. But as rates of steam displacement decline below
2 kg/min/m2, they increasingly invite loss of oil to internal reflux, an aspect which is discussed
further below. Eucalypt distillers need their boilers and stills to be matched so that the steams
rate of flow cannot fall below 2 kg/min/m2 of charge (!still) cross-section area. For this purpose,
boilers may be taken as generating 1.6 kg of steam at 100C and 1 atm of absolute pressure for
each kW of their proven capacity. But at the generating pressures likely to be required, one
should not rely on more than 1.2 kg of steam per hour per rated kW. The old boiler ratings in
horsepower (HP) are misleading and should be ignored. They are not convertible on the basis of
1 HP !0.746 kW.
1 One calorie will raise the temperature of 1 g of water by 1C and is equal to 4.18 J of energy. One Btu will raise a
1 pound mass of water 1F.

Mixed vapours
If two immiscible liquids are in equilibrium with the same vapour space, each will contribute its
own characteristic vapour pressure to that space as though the other were not there. The mixture
will boil at the liquids points of contact when the sum of their two vapour pressures becomes
equal to the surrounding pressure. This enables the distiller to vaporise these natural oils in the
presence of steam without even approaching the temperatures at which they would boil alone.
For example, 1,8-cineole, an important component of many eucalyptus oils, exerts a vapour
pressure of 67.3 mm mercury (Hg) at 97.42C. At the same temperature steam exerts 692.7 mm Hg
pressure. The sum of the vapour pressures is then 760 mm Hg and equal to that in the
atmosphere. So cineole can be boiled away from the eucalyptus leaf in the presence of steam
under atmospheric pressure at 97.42C, whereas it would boil alone at nearer 177C and might
start to decompose. The hydrodistillation of all essential oils depends on bringing the two
immiscible liquids into contact at a temperature very close to the boiling point of the water.
Then the addition of even a very small amount of vapour pressure from the oil will cause the
mixtures total pressure to equalise the surrounding pressure. The mixture then boils away from
the herb surface at the rate that the latent heat to support this evaporation can be supplied.
For vapour pressure, VP, and molecular weight, MW, the ratio of oil to water in the ideal sat-
urated mixed vapour is given by:
massoil VPoil " MWoil

masswater ! VPwater " MWwater (1)
Since the molecular weights are predetermined, the vapour pressures control both the tem-
perature at which the oil and water boil together and the composition of the mixed vapour ris-
ing off the herb. Although these proportions are useful for calculation purposes, it is quite
impossible for them to exist in the final distillate issuing from the still. It is also relevant that,
although all vapour pressures increase with any given rise in temperature, that of the oil
increases by a substantially greater factor than does that of water. This phenomenon originally
led to a false theory from which many eucalyptus distilleries still suffer. But, for other reasons, it
is still important for the higher boiling oils, including perhaps E. dives (Type), whose oil exerts
much lower vapour pressures than does cineole.
The transference of heat

For the oil to vaporise inside a field still it must receive latent heat from condensing steam. This
can happen only if the steam is at a higher temperature than the liquid oil. At the oils point of
evaporation, the concentration of its vapour and the proportion of the total ambient pressure it
exerts will be at its maximum. Consequently, the pressure remaining to be exerted by the steam
is minimal and its temperature is the lowest that can produce a boiling mixture of oil and water
under the prevailing pressure.
When the oil vapour is dispersed through the steam in the general vapour space its concen-
tration, and the share of the total pressure it can exert, are very much reduced. The share of the
total pressure remaining to be exerted by the steam is correspondingly increased. So, in the gen-
eral vapour space, the steams temperature cannot fall below that at which it must exert the total
ambient pressure, less only a meagre contribution from the diluted oil vapour. Inevitably, this
temperature is higher than that at the point of evaporation on the herb, where the oil vapour is
saturated and exerts more of the pressure.

This difference in temperature between the general vapour space and the oils point of evapora-
tion is the vital principle of the distillation process. It is the temperature gradient that makes pos-
sible the transference of heat to vaporise the oil, and its magnitude governs the rate at which the
oil receives its latent heat and boils away from the herb surface. In short, the factors which govern
the delivery of the oils latent heat also control the efficiency of its distillation from the herb.
How theory affects practice
Feedback and processing time

Clearly, the oil can evaporate only as fast as its latent heat of vaporisation can be applied to it.
Then, for every oil and set of conditions, there must be a balance point for the maximum obtain-
able oil content of the general distillate vapour. Any further enrichment of the vapour would
lower its temperature and reduce the magnitude of the gradient. This would reduce the rate at
which heat is delivered to the oil and retard its rate of evaporation until the normal balance sit-
uation was restored. This is a perfect example of an automatic control system of a type frequently
called feedback.
If the maximum yield of oil is to be achieved with the minimum consumption of fuel and
time, as much of the distillate as possible must be made to pass with the maximum ratio of oil
to water that feedback will permit. This phenomenon affects not only the running costs per kg
of oil, but also bears on the next subject for discussion, the time taken to process each charge.
The time that a charge must occupy the still falls into two parts. The heating time is the period
from the first admission of steam to the still until it breaks through the top of the charge and the
distillate is flowing normally. This depends on the availability of steam, the rise from day tem-
perature to boiling point, and the mass of the charge. For calculating this time the mean specific
heat of eucalyptus herb is about 0.8 kcal/kg and the latent heat surrendered by condensing steam
is taken as 540 kcal/kg. The extraction time runs from the start of the normal flow of distillate to
the point when the herb is exhausted of commercially recoverable oil, the commercial end-point.
How the oil comes to the herb surface

Initially the oil is secreted deeply inside the eucalyptus leaves. By the end of the heating period,
hot water has condensed on all the leaf surfaces and penetrated their cutaneous layers. This water
sets up a diffusion process by which the oil seeks to equalise its concentration throughout each
microsystem. As oil diffusing to the surface is removed by passing steam it is replaced from the
region of greater oil presence inside the leaf. This movement of the oil to the outside of the leaf
continues at a rate which is proportional to the factor by which the oils concentration inside the
herb exceeds that on the surface.
Relation between charge height and extraction time

If the height of the charge is increased, the number of points the steam will pass from which it
may gather oil is also increased. As the vapours rise through the charge, they continually con-
dense on, and revaporise from, each successive herb layer as they come to it. They tend to be
enriched by nearly equal amounts of oil from each unit layer of herb.
So the amount of surface oil continually in transit at the top of the still tends to increase pro-
portionately with charge height. This travelling oil adds to the surface concentration on the top
layer of herb, and the factor by which the oils concentration inside the herb exceeds that on the

surface at that level is reduced by an equal amount for each successive layer from which the
steam has already gathered oil. The diffusion rate declines and the extraction time for the oil in
the top layer, which is that for the charge as a whole, increases accordingly; that is, by some fac-
tor of charge height.
The steams ability to deliver heat to vaporise the oil has been seen to be proportional to the
magnitude of the temperature gradient leading heat from the general vapour space to the liquid
oil on the leaf. Since this gradient declines as the vapour space is enriched with oil from every
herb layer below the top of the charge, the rate that the oil receives heat and boils away from that
level must also decline proportionately with charge height.
For practical, commercial purposes, a given steam flow may be seen as requiring a basic time,
t, to exhaust the oil from typical glands on the top layer of herb. The limiting factors extend this
time by an increment, #, for each unit of charge height. The total extraction time, T (minutes),
for a charge of any height, H, is then given by:
T !t $(H %#t) (2)
The parameters t and #t are determined from two simultaneous equations in this form which
are obtained from very accurately timed distillations of two charges having different heights.
Once the steam has traversed about 75 cm of a typical charge of eucalyptus leaf, it will have
gathered enough oil for the limiting factors of feedback and diffusion to take effect. Then, all the
vapours from above this putative level will have a constant ratio of oil to water and it will be
the maximum which feedback will permit. All oil that started in herb above this 75 cm level in
the still will be extracted in the richest distillate that nature will allow. To maximise the effi-
ciency this offers, stills and their charges should be as tall as conveniently practical for rapid han-
dling. Both this supposed 75 cm level and formula 2 are simplifications involving a minor
systematic error which increases with diminishing charge heights. But it becomes insignificant
with charges more than 1.25 m tall. Most commercial distilleries work with charge heights
between 1.5 and 2.0 m.
Another very important effect of feedback is that the amount of steam required to pass to
complete a distillation depends on the quantity of oil to be recovered and is independent of the
actual mass of herb in the still. If a charge contains so much barren plant material that its over-
all content of oil per kg is only one-third of average, its distillation will consume the same
amount of steam as a normal charge of the same species, having the same diameter but only one-
third the height, processed under similar conditions.
Typical distillation curve for Eucalyptus polybractea

Figure 6.1 plots the oil delivered against the water passed for E. polybractea, and shows how the
early part of the distillate from a charge of commercial height has a nearly constant ratio of oil to
water. Feedback and other factors limit the oil content of distillate vapours after they have tra-
versed a certain amount of herb. This characteristic applies to most other subcutaneously
secreted oils, although the level in the charge at which the limiting factors intervene will vary
considerably. Nevertheless, it enables engineers to calculate variations in extraction time due to
variations in the total oil content in the still.
Comparison of species yields and extraction times

Estimates of the extraction times for distillation of Eucalyptus species other than E. polybractea can
be made by first finding the time for E. polybractea in the new still and conditions, and then

2.0
1.8
1.6
1.4
Oil collected (l)
1.2
1.0
0.8
0.6
0.4
0.2
0.0
0 4 7 11 14 18 21 25 28 32 36 39
Water condensed (l)
Figure 6.1 Distillation curve for E. polybractea.
Table 6.1 Relative extraction times for Eucalyptus species other than
E. polybractea
Species Oil yield (%)a Relative extraction

time
E. polybractea 1.35 1.00

E. globulus 0.90 0.67
E. smithii 1.30 0.96
E. citriodora 1.125 1.51
E. dives (Type) 2.70 2.00
a Fresh weight basis, v/w.
applying the appropriate time factor taken from Table 6.1. For calculation purposes, variations
in the oil content of the herb may be dealt with by using virtual charge heights. The oil content
of a herb layer, 1 cm thick and 1 m2 in area, will be known for the herb sample which was test
distilled to determine the parameters t and #t in formula 2. This then becomes the standard oil
content for use with those parameters. When calculating the extraction time to be expected for
a charge of similar herb in any other still, its expected total oil yield is divided by its cross-
section area to give the oil content of a column 1 m2 in cross section. The columns oil content is
then divided by the standard oil content figure to get a virtual height H, for use in formula 2.
The figures used for the cineole-type E. polybractea serve as an example. Using direct steam
generated under 2 atm gauge in a separate boiler, the test material was distilled under atmos-
pheric pressure to 95 per cent of its estimated virtual exhaustion oil content, the economic end-
point. Then t was 18.27 min and #t was 0.411 min when distillate flow was 1.36 l/min/m2 and
herb oil content 37.3 ml per layer 1 cm thick and 1 m2 in area. With charge heights and distil-
late flows (see below) duly adjusted, the parameters used in formula 2 will give accurate extrac-
tion times for charges of E. polybractea. They may also be used to obtain guidance on the
extraction times for cineole-type oils from other species of Eucalyptus such as E. globulus and
E. smithii.

Relation between steam speed and extraction time
It is practical to treat the valuable oxygenated compounds as comprising most of the oil. Due to
their greater affinity for water they diffuse to the surface ahead of the minor hydrocarbon com-
ponents. Their rate of diffusion is proportional to the factor by which their concentration inside
the herb exceeds that on the surface. If the oxygenated bodies vaporised immediately on reach-
ing the leaf surface, as in fact the monocyclic hydrocarbons do, the concentration there would
always be nil. Faster flows of steam would make no difference to the relative concentrations and
could not speed up oil recovery. But it is known that the distillation of subcutaneous oils is
accelerated by faster flows of steam. This implies that, under any given flow, there must be an
appropriate quantity of oil on the herb surface whose concentration sets an orderly limit on the
rate of diffusion. By quicker removal of this oil, faster steam reduces its surface concentration.
Since the oils concentration inside the herb is not immediately affected, it will now exceed that
on the surface by a larger factor and diffusion will accelerate accordingly.
When the oil diffuses to the herb surface it forms numerous small circular patches of homo-
geneous oil. It can be shown that the oil will vaporise only from the perimeters of these patches
where it is in contact with the water that condensed to raise the temperature. Also for compari-
son with the oils concentration inside the herb, the area of the circular spot of diffused oil is
proportional to its concentration on the herb surface.
From the foregoing it can be shown that increasing the rate of steam flow by a factor of X3
will, ideally, speed up oil recovery by a factor of only X2. But, in practice, fluids do not increase
their rates of flow along restricted channels in the full proportion of the accelerating force. A lag
factor, R, must be introduced which may be expressed as its effect on the speed of oil recovery.
The resistance to diffusion increases, and the numerical value of R declines, with any faster rate
of steam flow. The formula relating different speeds of steam flow to the speeds with which oil
will be recovered is then given by
Z !RY2/3 (3)
where Z is the factor of change in speed of oil recovery against the clock; Y the factor of change
in steam speed, with speed expressed in kg/min/m2 of charge top area and R the diffusion lag
factor appropriate to factor of change in steam speed, Y.
The new extraction time, T, due to a factor of change in steam speed, Y, may be derived from
the original extraction time, t, using the relation
t
T!
RY2/3 (4)
The new amount of steam, W, required to pass as distillate due to changing the steam speed
by the factor Y, is compared with the original amount required, w, by
w
W ! R . Y1/3
(5)
The lag factor for Eucalyptus

Figure 6.2 relates the steam speeds factor of change, Y, to the diffusion lag factor, R, and applies
strictly for changing from a base condensate flow of 1.36 l/min/m2 of charge top area. However,

4.0
3.0
Y 2.0
1.0
0.0
0.6 0.7 0.8 0.9 1.0 1.1 1.2 1.3
R
Figure 6.2 Curve showing empirical relationship between Y and R for Eucalyptus.
in practice it appears to give usable values for R when Y happens to be a multiple of some other
base rate of flow. The graph may be used to help convert any original extraction time to what
it would have been at the graphs nominated base flow rate. If this is used as t in formula 4, and
for deriving a new value for Y, then the associated value for R will theoretically be free from
systematic error.
Herb surfaces and wet steam

Because water is a very poor conductor of heat, steam can impart its latent heat to the liquid oil
only by condensing onto the water surfaces in immediate close contact with the perimeter of the
surface oil patch. On absorptive herb surfaces, the oil and water intermingle by capillary action
all along their contact interface. This greatly increases both the active heat transfer area and,
naturally, the oils proportion of the distillate. With those herbs which rely on their absorptive
surfaces to create an adequate heat transfer area, the distillation fails when the surfaces become
saturated and are no longer absorptive.
Compared with herbs which are naturally absorptive or have been wilted in the sun to get the
same effect, the absorptive capacity of eucalyptus leaf is very limited. It may well be nearly sat-
urated by the water condensed to heat the charge, yet the oils rate of vaporisation is not
impaired as that of surface-born oils like mint and lavender would be. The surface oil patches of
eucalyptus are homogeneous and virtually circular. They are also minute, and so numerous that
even without intermingling at their perimeters, the aggregate length of oilwater interface is
enough to create an adequate heat transfer area, into which steam can usefully condense.
Eucalyptus distillations differ from some others in that vaporisation of the oil is not impaired if
the herb surface is nearly saturated by steam that has condensed. The inefficiencies and losses are
due to the steams wetness fraction.
Internal reflux
If the steam is very wet, amounts of cloud that are excessive for eucalyptus distillations will
lodge on the leaf surfaces in the still. This deposited moisture is added to the steam which orig-
inally condensed to raise the temperature and it may be further reinforced by fluid from collaps-
ing aqueous plant cells. This moisture soon floods the nearly non-absorptive leaves to the point
where they can no longer hold it. A downward flow of liquids is established, dripping and gath-
ering pace and volume from one leaf to the next, which washes oil to the bottom of the still. The

loss of oil is evidenced by an excess of discoloured water in the bottom of the still at the end of
each distillation. Field tests have shown well-established distilleries losing 30 per cent of the
herbs recoverable oil to this cause.
With satellite boiler steam generated under less than 2 atm gauge, a distillate flow of
3 kg/min/m2 will create an upward wind through the charge which opposes this reflux and
reduces, but does not eliminate, the loss. In wetter conditions a faster flow of steam may help,
but more of it will be used per kg of oil recovered. As noted earlier when discussing steam
requirements, losses of oil to reflux become increasingly severe as flow rates decline progressively
below 2 kg/min/m2. At all flow rates, losses increase as the steams wetness fraction rises. The
distiller can gauge his loss from the amount of dirty water gathering in the bottom of his still. It
should not be there but it usually is.
The hydrophylic effect

If a cloud particle strikes an exposed oil surface it will roll up a coating of oil which it can carry
upward through the charge. Coated cloud particles which lodge on herb surfaces higher up the
still, and are then vaporised, accelerate the extraction of the oil. So relatively rich distillates and
apparently short extraction times are achieved by many of the very primitive operators distilling
Eucalyptus and tea trees in the Australian bush, because they use the very wet steam which
results from boiling the water in the bottom of the still.
Many oil-coated cloud particles fail to lodge on herb surfaces further up the charge. They
escape from the still in the liquid state and are too small to be caught by any normal separator.
Their oil coatings are lost in the discarded water. Evidently, the amount of oil lost to this
hydrophylic effect is proportional to the number of cloud particles reaching the top of the still
and the area of oil held exposed to them while they pass.
Due to lodgement on each successive layer of herb, the residue of the steams original wetness
fraction which reaches the top of the still declines as a function of charge height. Conversely, the
time that the oil area remains exposed at that level increases as a function of charge height. Tests
with charges of practical commercial height show that these effects can compensate each other,
so that the amount of oil lost to the hydrophylic effect is proportional only to the initial wetness
fraction of the steam and the cross-section area of the charge. For each case, this loss of oil tends
to be a significant fixed quantity, the same per unit area for all practical charge heights. So taller
stills give better yields of oil.
E. polybractea seldom assays an oil content under 1.75 per cent by weight (fresh basis). When
it is packed to a density of 250 kg/m3 in commercial stills 1.5 m in diameter by 1.7 m tall, and
processed with steam generated under some 2 atm of gauge pressure, most field distillers would
be satisfied with a return of 11.5 kg of oil. Closer inspection shows that the apparent fixed loss
of this oil to the hydrophylic effect is 1.5 kg/m2 of charge area, representing over 20 per cent of
the herbs recoverable oil at commercial charge heights.
Comparing equal flows of naturally wet steam, lower generating pressures in the boiler give
shorter extraction times for equal returns of oil. Steam from the lowest pressure expands and
dries out least on entering the still. Compared with steam from higher pressure, it increases the
number of coated cloud particles carrying oil up the charge, as well as those escaping from the
still. Since this accelerates both the speed with which oil is removed from the herb and the rate
that it is lost to the hydrophylic effect, it shortens extraction time and enriches the distillate
without raising the yield. However, it is not feasible to exploit the speed of this hydrophylic
translocation of the oil because with all stills of practical commercial height the 2025 per cent
loss of the available oil persists.

Comparing steam generated under low and high pressures
Consider a typical example of a common low-pressure boiler which delivers 300 kg of heating
steam and then passes 1000 kg of steam through a 2.5 t trailer-load of herb. It recovers only
40 kg of oil when the charge is assayed to contain 50 kg. If the steams wetness fraction at the
still is as low as an unlikely 3 per cent, almost 40 kg of cloud will have been carried into the still.
It is not difficult to show that each kg of cloud particles could carry off more than the 250 g of
oil needed to explain the loss.
Now let the boiler deliver steam to the still under 7 atm gauge. On expanding into the atmos-
pheric pressure still, this steam may take up almost 1.5 per cent of its own weight in water from
the herb, instead of importing 3 per cent of cloud particles. It follows that, even if there were no
reduction in the requirement of steam, which is contrary to all theory and experience, the
amount of cloud available to promote reflux or to carry off oil will be some 58 kg less than with
the lower pressure steam. A very big state of the art distillery processing tea tree (Melaleuca), for
which the requirements are similar to Eucalyptus, adopted these parameters and reduced the con-
sumption of steam per kg of oil to two-thirds of normal, while improving the quality and
markedly increasing the yield of oil per tonne of herb.
Distillation under gauge pressure

Measurable gauge pressure in the still is helpful for recovering very high-boiling oils like
vetiver. However, all the oils from eucalyptus are moderately volatile and do not justify the
higher operating and capital costs that pressure distillation incurs. It can be shown (Denny
1991) that raising the operating pressure from 1 atm abs to 2, enriches the distillate by a factor
of 1.5 and only two-thirds as much steam must pass to extract a given yield of oil. Pressure also
increases the temperature gradient, but not by enough to matter with the eucalypts.
Practice the equipment
The stills
All heat-losing surfaces of stills should be insulated with rockwool, or equivalent, about 50 mm
thick.
Laboratory stills
Laboratory steam distillations using stills only 20 or 30 cm tall are usually unhelpful. They are
no guide to herb parameters and are misleading as to herb quality and yield. If the condensate
water is returned to the still and the process is continued to total exhaustion, comparisons of
yield only may be made between multiple tests. With very limited quantities of herb, better
indications of yield and quality are given by water distillations to exhaustion in a glass
Clevenger apparatus. With suitable plant materials, comminuted if necessary, an accurate image
of commercial operation can be obtained with drainpipe stills only 20 cm in diameter, provided
they are about 1.3 m tall. In the laboratory it may be possible to avoid the hydrophylic effect by
desiccating the steam for the drainpipe still.
Pilot still with small steam evaporator

This still (Figure 6.3) is popular for small-scale operation and is capable of passing 45 l of distil-
late per hour at atmospheric pressure. It is made from two galvanised 200-l oil drums and so is

Coolant water
Vapour
outlet Condenser
(7 tubes, 19 mm OD 1.5
50 mm m)
Oil/water
570 mm condensate
Still
extension
1650 mm
Six screw
clamps 1.5 m
Still stand
base pipe
Metal
grid and legs
Flexipipe 37 mm
Steam
Evaporator
Flue
To water
supply Water level
250 mm
Water level 800 mm

holder
9 parallel wa
ter tubes 38 m
m
L.P. gas burner
Figure 6.3 Pilot still with small steam evaporator.
not expensive; even the evaporator can be put together in any normal farm workshop. The con-
denser, however, may need to be fabricated professionally. The still lid should be stainless steel
but it does not require difficult cutting or welding. This still will hold over 100 kg of fresh herb
and the evaporator will give a steam displacement rate very close to 3 kg/min/m2 with a suitable
gas burner. However, with this wet steam and the virtually non-absorptive eucalyptus leaf, the
2025 per cent loss of oil to the hydrophylic effect is inevitable. But the scheme is very good for
absorptive herbs.
Water and steam distillation with under-charge kettle

This system (Figure 6.4) is usually directly fired by wood fuel under a cylindrical still with a
plain, flat bottom, rather than by oil as indicated. The former was a common method of distill-
ing eucalyptus oil, but it is not a good one. The steams wetness fraction is imponderably high
and causes a strong reflux flow. The thermal efficiency of the circular flat plate kettle is scarcely
15 per cent, and solid fuel cannot possibly generate an upward flow of steam through a charge
of equal diameter sufficient to reduce the reflux. There is a massive hydrophylic translocation of
oil, which accelerates both its extraction and its loss. This gives the primitive still an illusion of
efficiency, with extraction times that seem short for its slow rate of flow, and distillates so rich
that it passes barely two-thirds of the amount of steam required by many, supposedly more
advanced, distilleries using small low-pressure boilers to recover the same amount of oil. One
can see this causing the competing claims of superior efficiency to protagonists of each system
when, in fact, both methods were often equally inefficient.

Coolant water
Multi-tubular condenser
Flue on suspended lid
To separator
Still
Steam
Oil
Burner
Boiler
Furnace
Figure 6.4 Water and steam distillation with under-charge kettle.
Hinged lid
Coolant water
Fixed condenser
Oil/water
condensate
Still to separator
Boiler
Steam
Figure 6.5 Direct steam distillation with a separate boiler.
If the kettle for water and steam distillation has the Babcock tubes shown in Figure 6.4,
and the furnace is fired by a diesel burner, the overall thermal efficiency can approach 80 per cent
if well designed. The faster boiling rate reduces reflux but the steam is still wet enough to pro-
mote serious hydrophylic loss when processing the non-absorptive eucalyptus leaf. However, the
system is very suitable for naturally absorptive and partially dried herbs.
Direct steam distillation with a separate boiler

With steam generated from a separate boiler (Figure 6.5) and under different gauge pressures up
to about 2 atm, the ratio of the amount of oil returned, to the amount lost, in any given still usu-
ally varies relatively little. With the lowest generating pressures the distillate ratio of oil to

Figure 6.6 Packing still with comminuted E. globulus leaf and twig, Portugal (photo: J. Coppen).
water approaches that of the water and steam system. But the direct steams potential for faster
distillate flows can save time. On the other hand, if the steam is generated under some 7 atm
gauge, and expands to atmospheric pressure as it enters the still, it superheats sufficiently to
ensure that no wetness fraction at all is carried to the herb. Its residual surplus heat is then still
enough to dry out any additional condensation due to thermal inefficiency. At the end of the
distillation the space beneath the charge is perfectly dry, showing that reflux is eliminated, and
greatly improved yields suggest that losses due to the hydrophylic effect have been minimised.
If the boiler must work at low pressure, it might be worth testing comminution of the mate-
rial with a chopper as it is being loaded into the still. It then packs more densely and traps more
of the coated cloud particles. An example of this in Portugal, where E. globulus is distilled, is
shown in Figure 6.6.
Trailer stills
These are large boxes filled directly during mechanical harvesting in the field and in the context
of eucalyptus distillation are found only in Australia. They eliminate all manual methods of fill-
ing and emptying the stills and were developed in the early 1970s by GR Davis Pty Ltd as a
means of reducing high labour costs. An example of one such trailer still is shown in Chapter 7
(Figure 7.2).
They are subject to all the normal principles of distillation and are usually large enough to
hold at least 2.5 t of herb. On arrival at the distillery, a lid with a central vapour outlet and flex-
ible hose (which connects to the condenser) is lowered over the trailer and fixed securely to it.
Ideally, a typical cross-section area of 8 m2 would demand the output of an 800 kW boiler.
Thermal insulation of the trailers vertical walls saves fuel, but the herb close to the wall is such

a small part of the whole charge that the loss of some of its oil is not obvious enough to cause
alarm. In practice, operators ignore the accumulation of dirty water in the bottom of the trailer
still. Insulation of the trailer lid gives maximum steam flow, but causes unacceptable back pres-
sure when air is being expelled at the start of each run if the condenser is a single tube type
tapering to a restricted final outlet. Unlike steam, air does not collapse in volume on entering
the condenser. If some of the early vapours condense on the cool lid it reduces their speed and less
pressure is required to expel air at the slower rate. An array of parallel, floor level, sparge pipes
joined to a common header is commonly used to admit steam to the still. Pressure in the header
should be maintained close to 1 atm gauge. Alternatively, the steam may enter a pressure equal-
ising space under a perforated false floor carrying the herb. The perforations must be fine enough
to avoid sticks from gripping in them which would prevent the load sliding off easily when
tipped for final discharge. At the end of the distillation the lid is removed and the trailer towed
away to be replaced by a new one.
Handling systems
Distilling essential oils involves getting the fresh herb to the distillery and may also entail mov-
ing the exhausted bulk away from it. These are major activities involving both capital and oper-
ating costs. Frequently, inadequate provision is made for these during the planning stage and
this leads to administrative and financial difficulties later on. In some cases, spent herb from
eucalyptus distillations is used to fuel the boiler or is composted on-site for subsequent sale, and
it does not incur the same sort of removal costs.
In Australia, trailer stills with power tipping systems for discharging spent loads automati-
cally solve the transport problem. There will be at least one more stand for trailers at the
distillery than the number distilling at any one time. This allows for receptions and removals in
the idle bay without disrupting distillation. At change time the steam is merely switched from
the exhausted trailer to the new one. So the system is a genuine continuous operation.
Orthodox cylindrical stills can use cartridges. These are stout bins with mesh bottoms which
may be filled by the harvester in the field or by hand at a point near the stills. They can be
moved on roller beds to a point under a gantry where an overhead trolley hoist picks them up.
They may be liners for normal stills or they may constitute the still themselves. In either case,
their bottom perimeters will rest on a steam seal such as piano note cross-section neoprene, car-
ried on a flange sealed to the still wall 150 mm above its floor. Where the cartridge is a liner for
an orthodox still, the lid closure and insulation are normal, but the height of lift and gantry may
be inconvenient. If the cartridge is merely lowered onto a simple still base just above floor level,
the lift required is much reduced and the gantry simplified. The still lids are then a common fit
to all cartridge tops. Then the cartridge must either carry its own insulation, which may thus be
exposed to damage, or each base must have doors lined with rockwool which close tightly
against the still cylinder. The latter is the best scheme, but not so easy to install. Loosely fitting
doors turn the cartridge wall into an effective air condenser with disastrous results. When car-
ried on the gantry, the cartridges are suspended by ropes from the hoists swingletree to pivots on
the cylinder wall. The latter are designed to facilitate tipping the exhausted herb at the end of
the gantry. A tractor with a front end blade then pushes it to a compost heap. The cartridge sys-
tem facilitates transportation and also permits such rapid replacement of exhausted charges that
it is virtually a continuous operation.
In older systems, the still is filled manually and the herb forms a pudding on a grid that can
be lifted from the still for discharge. The still is necessarily out of action while it is being filled
and the grid legs cause wasteful steam leaks through the charge.

On both theoretical and practical grounds, essential oil distillers should be very careful of so-
called continuous distillation systems. They usually involve a moving column of herb traversed
by a counter current of steam. They do not suit eucalyptus distillation.
The flow diagram

Figure 6.7 depicts the general arrangement of water and steam piping for a modern eucalypt dis-
tillery. It is necessary to treat the boiler feed water to minimise salts and oxygen that can harm
the boiler tubes. Reputable boiler manufacturers will give advice as to the particular treatment
required. All practical rainwater should be collected and used for the boiler. The discharged con-
densate water can also be used if it does not create foam or undesirable volatile products of
decomposition. It is free of salts and, unlike the petroleum hydrocarbons, the traces of essential
oil in the distillate water have tested harmless to boiler tubes.
Most of the energy consumed by a distillery is lost in the heat discharged in the condensers
cooling water. Schemes for saving some of this by using it as preheated boiler feed water are
more academic theory than practical measures. The best method of preheating the feed water is
to hold it in a water jacket round the furnace flue. Some economy may be effected by using spent
herb as boiler fuel. However, this requires major capital outlay for a Dutch oven furnace which is
justified only where other fuel is not readily available. It is usually better economy to compost
the waste material and return it to the fields.
The piping must allow for the distillery to use water at twenty times the amount actually
boiled away per day. This provides for the condenser coolant water to be turned off when distil-
late is not running during changing and heating periods. Design of the condenser will normally
allow for a cooling water flow equal to fifteen times the planned distillate flow. Provision for
emergencies requires that double this rate be available at the condenser coolant inlet under a
pressure of at least 3 m head.
The condenser
The single pass, multi-tube, vapour-in-tube condenser is immensely superior to all others for
essential oil distilleries. It has the following advantages not available from single-tube, spiral
Condenser
Boiler
cooling
water Boiler
head tank Still feedwater
tank
Oil/water
vapours
Pump
Condenser
Oil/water Drain Pump
condensate
Return to water reservoir Boiler feedwater
treatment tank
Oil
Return water line from separator
Return water
Separator Gravity flow holding tank
Pump
Figure 6.7 Flow diagram showing layout and fluid transfers in a modern distillery.

coil condensers. It is nearly five times as efficient in the use of cooling water per unit of heat
exchange area and takes up much less space. It can be instantly adjusted to deliver the distillate
at any chosen temperature for separating oil and water. It readily releases air at the start of each
distillation without unacceptable back pressure. It is easy to clean the inside of the tubes and
access is easy for cleaning the outside of the tubes, if required. An example of a multi-tubular
condenser being used for eucalyptus oil distillation is shown in Figure 6.8. Note that it is here
being used in the vertical position but it can equally be used horizontally.
Consideration of the factors affecting condenser design are given elsewhere (Denny 1991), but
the sample specifications given below are amenable to linear interpolation and so will cover a
wide range of operating conditions. They apply for the following: connecting pipe from the still
is &3 m long with only one 90 bend; coolant water enters at &25C and flows at fifteen times
the distillate flow rate; bundles of stainless steel tubes 20 mm (3/4) outside diameter (the best
size) and about 1 mm wall thickness, arranged in an equilateral triangle pattern with centres 11x
tube diameters apart; coolant baffles not more than 11x shell diameters apart; condensate cooled
to about 22C above the temperature of the entering coolant water. Note that the best separation
of oil from water occurs at 4550C, not lower as is commonly supposed.
The relation between rate of condensate flow and tube numbers is linear. A guide to the
number of tubes required to handle satisfactorily a range of condensate flow rates is given in
Table 6.2.
Figure 6.8 Multi-tubular condenser being used for eucalyptus oil distillation, Australia (photo:
J. Coppen).

Table 6.2 Recommended parameters for multi-tube condensers of the single
pass, vapour-in-tube type
Rate of condensate Diameter of Number of tubes Number of tubes

flow (kg/hr) connecting (20 mm diameter (20 mm diameter
pipe (mm) "2 m long) "3 m long)
200 75 20
500 125 50 35
1000 125 100 69
1500 175 104
Ancillary equipment
Figure 6.9 shows a convenient arrangement for the condenser, separator and end-point indicator.
The condenser is used in the near horizontal position, which permits the separator and other
equipment to be used at a convenient bench height. The horizontal condenser uses only an
insignificant amount more water than when installed in the vertical position but the extra con-
venience is, by contrast, very significant.
Separator
It is a mistake to have the condensate delivered to the separator at a low temperature in the belief
that less oil will be lost to solubility than in warmer water. Most of the loss to solubility occurs
in the condenser near 100C and it is very difficult to demonstrate any commercially significant
increase in a distilled oils solubility in water raised from 20C to 60C. A higher temperature
increases the difference in density between eucalyptus oils and water, thus increasing the force
promoting separation. At 45C the forces due to the waters viscosity, which resist separation, are
only 60 per cent of what they are at 20C. At 45C, small globules of eucalyptus oil rise through
water twice as fast as they do at 25C. The inner cylinder of the separator holds the first two min-
utes of full distillate flow, because it will normally be cooler than the water remaining in the
separator from the preceding distillation, and, if it were not held until all temperatures had sta-
bilised, it would go straight to the bottom and out of the water discharge pipe with its very rich
content of oil.
The separator operates continuously. The central core, at the bottom of which is an inverted
funnel, is inserted down the neck and inner cylinder and provides a primary stage separation
with minimum turbulence. To ensure that delivered oil holds minimal suspended water, 68 cm
depth of oil should be retained in the neck. The cross-section area of the outer annulus is calcu-
lated to ensure that the water travels downward towards the outlet slightly more slowly than the
oil particles rise through it. The cineole-type oils rise at 10 mm/min at 45C, which is faster than
those of E. dives (Type) (6.4 mm/min) and E. citriodora. Inevitably, a properly designed separator
is much larger than most distillers are used to. If the oil particles travel more slowly than the
water they will be carried away and lost.
Recommended dimensions of separators for eucalyptus oils of the cineole and E. dives types,
for a number of different distillate flow rates and at 45C, are given in Table 6.3.
End-point indicator
Taking small samples of distillate in a graduated cylinder is an unreliable way to discern when
the distillation should be stopped. An indicator of the type shown in Figure 6.9 for oils such as

Coolant water
Condenser
2250 mm
Still End-point
indicator
Oil
out
Condensate
Receiver- water out
Separator
Bench height
700 mm
Figure 6.9 Arrangement of ancillary equipment.
Table 6.3 Recommended dimensions of separators for eucalyptus oils
Rate of Height of both Diameter of inner Diameter of outer cylinder (cm)

distillate flow cylinders (cm) cylinder and
(l/min) neck (cm) Cineole types E. dives/others
1 30 9 37 45
3 30 16 64 79
6 30 22 90 111
9 50 22 109 136
12 50 24 132 156
15 50 27 140 175
18 50 30 154 192

eucalyptus, which are less dense than water, with a central, graduated glass column, is strongly
recommended. The main body of the vessel has a capacity of about two minutes of distillate
flow. During normal running, the plug cock at the bottom of the indicator is open and distillate
flows directly into the separator inlet funnel. To measure the rate at which oil is being produced
the plug cock is closed. When the oilwater mixture rises to the level of the upper outlet the
supernatant oil appears in the graduated glass column; the rate at which the depth of oil
increases indicates the rate at which it is being produced.
Acknowledgements
Simon Coppen is thanked for preparation of Figures 6.3, 6.4, 6.5, 6.7 and 6.9 from the authors
original drawings.
References
Denny, E.F.K. (1991) Field Distillation for Herbaceous Oils, 2nd edn, Denny, McKenzie Associates,
PO Box 42, Lilydale, Tasmania 7268, Australia.

Part 2
Cultivation and production of
eucalypts around the world
With special reference to the leaf oils

7 Cultivation and production of
eucalypts in Australia
Geoffrey R. Davis
History of oil production1
The early days

Eucalyptus oil was distilled as early as 1788, the first year of white settlement in Australia, when
Governor Phillip sent a sample to Sir Joseph Banks, and in 1790, John White, the Surgeon-
General, despatched a quart of oil of Eucalyptus piperita to England. However, it was not until
1852 that a still was set up for the commercial distillation of eucalyptus oil. Joseph Bosisto, who
had emigrated from England four years earlier, established his still on Dandenong Creek, about
40 km southeast of Melbourne, with the encouragement of Ferdinand von Mueller, then
Government Botanist in Victoria.
In those early days, before much was known about the chemical composition of eucalyptus
oils, several different species were worked, giving oils of varying composition. Stills for the
production of oil were established in Gippsland, just east of Melbourne, and in Tasmania. The
oil was used as a disinfectant, as a solvent, and for its therapeutic value. For the distiller of
the oil, the critical factor was the yield of oil rather than its composition and, initially, species
containing a high percentage of oil were favoured.
The search for high-yielding species saw the commercial activity move to western Victoria,
particularly in the southern Mallee region, and then east towards central Victoria. At the same
time stills were established in Tasmania and South Australia, particularly on Kangaroo Island.
Early research
While the commercial distillers were seeking better sources of the oil, scientific investigation
began to make significant headway only during the last two decades of the nineteenth century.
For the industry to develop it was essential to know the chemical composition of the different
oils, whether the composition was constant within a species, and the factors, if any, which
affected the yield and composition. At this time, most oil production was in Victoria, but the
main research was carried out at the Technological Museum in Sydney. This institution, later
named the Museum of Applied Arts & Sciences, was set up in 1880 to, inter alia, investigate the
economics of the natural products of Australia, and of New South Wales in particular, and to
make this information available to the public (Grolier Society 1965). Although it covered a
wide field, a lot of its research was on the essential oils of the many plants unique to Australia.
1 A more detailed history of the industry is given by Shiel (1985).

Its reputation grew and the Museum soon became the foremost authority on Australian essential
oils, particularly the eucalyptus oils.
During the Museums ninety-nine year life, the combination of a botanist and a chemist as the
research leaders was of great value to the essential oil industry. The initial work of the eminent
botanist J.H. Maiden was followed, in turn, by that of R.T. Baker and H.G. Smith, A.R. Penfold
and F.R. Morrison, and J.L. Willis and H.H.G. McKern, who, with their more recent successors
R.O. Hellyer, E.V. Lassak and I.A. Southwell, have provided the scientific basis necessary to
develop the industry. The early work established the chemical composition of the oils, within
the limits of chemical knowledge and methods then available. Penfold, together with his
co-workers, was particularly prolific throughout the 1920s, 1930s and 1940s (Coppen and Dyer
1993). The composition of the oil from a given species appeared, then, to be relatively constant.
While the oil yield was also characteristic of the species, it could vary markedly between
individual trees within a natural population.
However, further research showed that within some species pronounced chemical variation
could exist. The plants which exhibit such variation, first termed physiological forms by their
discoverers, Penfold and Morrison, are now usually referred to as chemical variants, chemotypes
or chemovars. Marked variation in oil composition may exist between populations or between
individual trees within a population. An early example of this phenomenon within Eucalyptus
was found to be that of E. dives. Some populations (Type) produce oil commercially valued for
its 4050 per cent piperitone content; other populations (Variety C) produce oil rich in cineole,
also commercially valuable. Yet other variant populations, of no present commercial importance,
are known: Variety A yields an oil consisting chiefly of hydrocarbons, whilst Variety B yields
oils of variable composition, made up of constituents found in the other three forms.2 However,
for practical commercial purposes, populations of trees yielding oils of the desired composition
have now been well defined and the oils distilled from them vary in their properties only within
narrow limits. Recent work indicates that genetically determined quantitative variation (often
to an extreme degree), rather than qualitative variation, accounts for these chemical forms.
Oil-producing species
Of the hundreds of species of eucalyptus, most produce an oil, but few have oil of commercial
value. To be of such value, the quantity of oil in the leaves must be at least 1 per cent of the fresh
weight of leaf and the chemical composition must be of interest to the market. Apart from one
or two speciality oils, such as those from E. olida (see below) and E. staigeriana (produced in
Brazil), there are only three types which presently meet these criteria: oils rich in cineole, piperi-
tone and citronellal. In Australia, the citronellal type has only been produced to a very small
extent.
In the early stages of the industry, the species worked near Melbourne were those which
produced the cineole-type oil, although the cineole content varied anywhere between 30 and
70 per cent. Phellandrene (mainly !-phellandrene) was a common constituent. It is not easy to
be sure which species were worked because at that time the taxonomy of the genus was not well
established. By the fourth quarter of the nineteenth century E. globulus oil, containing 6070 per cent
cineole, was being produced in southern Victoria and Tasmania. Following the first inclusion of
2 The terms Type, Variety A, Variety B, etc., were introduced in the 1920s and applied chronologically within a
species as each distinct type of oil was enumerated. It is preferable, nowadays, to avoid using these terms and to state
the particular chemical variant by name.

eucalyptus oil in the British Pharmacopoeia (BP) in 1885, compliance with the specification
required increasingly higher levels of cineole, and by 1924 the minimum cineole content was
70 per cent, the level at which it is today. This made E. globulus more popular since the cineole
content could be increased to 70 per cent or more by simple rectification and the phellandrene
content was negligible. The BP allowed only a very low level of phellandrene. It still does,
although there appears to be no good reason for this.
Towards the end of the nineteenth century the main part of the industry was in the central
western part of Victoria, where availability of good-yielding, high-cineole, phellandrene-free oil
attracted distillers. Although oil was extracted from several species, including E. viridis and
E. sideroxylon, and elsewhere from E. radiata and E. robertsonii and others, the industry in the cen-
tral and western part of Victoria was firmly based on E. polybractea. Oil was also produced from
the same, hardy species in the mallee country of the western plains of New South Wales. The oil
is high in cineole, 7888 per cent, and phellandrene-free; it is also produced in reasonable yields.
E. polybractea has a remarkable ability to coppice after harvest and grows on land which is of lit-
tle use for anything else. In other parts of New South Wales, and parts of Victoria, cineole vari-
ants of E. radiata and E. dives were the major source of the medicinal type of eucalyptus oil,
particularly the 70 per cent cineole grade which conformed to the several national pharma-
copoeias which listed eucalyptus oil.
In the early part of the twentieth century, oils from various types of E. radiata and E. dives
were produced on the south coast of New South Wales and on the mountains further west. In
addition to pharmaceutical applications, much of the production, particularly that from E. dives
and the phellandrene variant of E. radiata (then known as E. phellandra), was used for mineral
flotation and in disinfectants.
Commercial production
Although hundreds of distillers have been in business during the 140-odd years that eucalyptus
oil has been produced in Australia, there have been just a few major ones in the industry. Joseph
Bosisto, the initial force in the eucalyptus oil industry, continued to be involved in it until his
death in 1898. The following year, J. Bosisto & Company Pty Ltd was constituted, and operated
until 1951 when it became a subsidiary of Drug Houses of Australia (DHA). DHA was taken over
by Slater Walker in 1968. In 1974, Peter Abbott purchased the eucalyptus oil section of DHA and
the name Felton Grimwade & Bickford, the present name of the company. This company also
owns the name Bosisto & Co., which is still in use today, and the Bosisto Parrot Brand name.
Early on, F.H. Faulding & Co. became involved in eucalyptus oil production, particularly in
Victoria and South Australia and, to some extent, New South Wales. This company has main-
tained its connection until the present day. In 1880, the Tasmanian Eucalyptus Oil Company
started in Tasmania. It moved its operations to Melbourne in about 1920 and remained a major
buyer until 1947. W.K. Burnside Pty Ltd were one of the main buyers and leaseholders of land
for oil production from the 1920s to the 1960s. This company also operated in New South
Wales.
In 1912, Fred Webb of Braidwood, a gold fossicker, distilled oil from the narrow-leaved pep-
permint, E. radiata (phellandrene variant). He went to Sydney and while there ordered a suit
from Mr A.J. Bedwell, a tailor who carried out a lot of country order business. The suit, when
made, was sent to Braidwood and to Mr Bedwells consternation payment was made by the
arrival of a small drum of eucalyptus oil. Bedwell not only succeeded in selling the drum of oil
but soon sought more. By 1919 he gave up his tailoring business and became the major force
in eucalyptus oil in New South Wales until selling out to Plaimar Ltd of Perth in 1950.

A.J. Bedwell Pty Ltd continued producing as a Plaimar subsidiary until 1971, when its euca-
lyptus oil interests were acquired by G.R. Davis Pty Ltd.
The eucalyptus oil industry continued to be centred in Victoria until about 1950, producing
mainly cineole-type oils. It had provided work for many men and a lot of oil was produced, but
the industry was not stable and was profitable for the producers for short periods only. For most
of the time it was subsistence farming. The main problems faced by the industry were fluctuat-
ing markets, due mainly to competition from other countries, replacement of the oil with alter-
native, cheaper products particularly in the case of mineral flotation and, in recent years, the
stubborn refusal of all Victorian state governments to allow adequate tenure of land.
In the early post-war years there was a world shortage of menthol. Plaimar Ltd had succeeded
in earlier years in producing l-menthol from l-piperitone, the major compound of E. dives (Type)
oil. Several other manufacturers in Australia, Europe and USA were able to produce liquid
menthol from this source and the demand for piperitone-rich E. dives oil increased substantially.
The main stands of E. dives (Type) are in southern New South Wales and, as a result, much of the
industry moved there. The production of cineole-rich oils also increased in New South Wales,
while continuing in Victoria. The demand for locally produced E. dives (Type) oil lasted, with
fluctuations, for about twenty years, until other countries, particularly South Africa, were able to
produce low-cost oil. More importantly, production of menthol from alternative sources (natural
menthol from Mentha arvensis and synthetic menthol from turpentine) could supply the worlds
needs and the piperitone route from E. dives became increasingly less economic.
Early methods of production

For the first hundred years of the industry, almost all eucalyptus oil was produced in very simple
bush stills by steam distillation at atmospheric pressure. The typical bush still consisted of a
simple tank, usually mild steel, into which leaf and terminal branchlets were stacked on a grid
about 1530 cm from the bottom. Water below the grid was heated by a fire directly below the
tank. The steam so generated passed up through the leaf to an outlet just below, or sometimes
through, the lid. The resulting mixture of hot oil and water vapours was led to a condenser
often simply a long pipe passing through a dam or stream and the condensate then passed to a
separator where the top layer of oil was removed from the oilwater mixture. In some cases
steam was produced in a separate boiler and injected into the tank holding the leaf. This
was necessarily so when wooden vats, rather than steel tanks, were used to hold the leaf. These
simple stills were used because they were easy to construct and operate, were low-cost (second-
hand tanks were often used), and could easily be set up and dismantled, an advantage when they
were used in areas where there was insufficient leaf available to support a large or permanent
operation. There were, of course, some much larger and more sophisticated plants operating in
the early stages of the industry, where large natural stands of the required species were available.
These plants were usually, but not always, established and owned by one of the major companies
referred to earlier. It is worth noting that the oil produced in the simplest direct-fired still is not
inferior in quality to that produced in the most sophisticated apparatus.
It is fortunate that in stands of commercial oil-bearing species the required trees usually
dominate the stand. Furthermore, where a single species is worked, the composition of the oil is
similar throughout the stand, although the yield of oil might differ substantially from tree to
tree. There are some exceptions to this but, generally, once a stand of trees with good quality oil
is found, the producer can harvest it with confidence.
All the commercial oil-bearing eucalypts coppice well and, providing the interval between
harvests is not too short so that there is no decline of vigour in the production of foliage, they

can be worked on a sustained yield basis. Coppicing was practised from the early days of oil
production. The only tools required were an axe for felling the tree and a heavy knife for remov-
ing the leaves and terminal branchlets. In the case of the mallee species, that is, the multi-
stemmed trees commonly found in the drier inland areas, the tree is normally cut at, or close, to
the ground using a billhook or curved knife. Regrowth comes from the lignotuber just below
the ground. In the early years of the industry this arduous work was done mostly by itinerant
workers, often as an alternative to prospecting for gold. Few were able to make a good living
because of the low value of the oil. Nevertheless, production of oil gave a start to many of the
post-war migrants. When farms were being developed on land where oil-bearing trees occurred,
production of eucalyptus oil provided a cash return before the traditional agricultural crops
matured. New farmers were prepared to sell oil cheaply just to get a cash income.
Competition with other producers

Ever since the industry first started in Australia other countries have planted commercial
oil-bearing eucalypts and for almost a century have been able to offer oil on the world market.
The main early competitors were Spain and Portugal, where oil was produced, mainly from
E. globulus, as a by-product of the timber industry. In Australia, despite the advantage of low
costs for much of its history, high production costs in the 1950s, and for some time after, made
it uncompetitive in many world markets, including the eucalyptus oil market. The advantages
of producing oil as a by-product, rather than the sole product, proximity to the main markets,
and a low wage structure, enabled first the Iberian countries, and then China, to put oil on the
market at prices which Australia could not meet. South Africa, too, began to supply Australia
with piperitone-rich oil from E. dives (as was noted earlier) and medicinal (cineole-rich) oil from
E. smithii. It became apparent by the 1960s that if the industry were to survive, mechanisation
of production and development of superior trees in plantations was essential.
It is unfortunate that Australia has been unable to retain the larger part of this uniquely
Australian product. However, very rapid growth of Eucalyptus in other countries, probably due
to the absence of natural predators, together with the factors noted above, meant that not
enough money could be generated in the industry, either to make it profitable for producers or
to provide the capital needed to develop the industry. The value of the product on the world
market, except for quite brief periods, has not been enough to cover production costs in this
country. Much of the land cleared of oil-bearing trees for planting traditional agricultural crops
is actually better suited to growing trees for oil. Except for very small areas this calls for plantation
development, which is costly and beyond the financial capacity of most producers. Furthermore,
as noted earlier, in Victoria, where larger producers could have financed such development,
short-sighted Government policy has frustrated such moves by its refusal to recognise the need
for reasonable term land tenure.
Modern methods of harvesting and production

On the plain country, attempts were made as early as 1950 to mechanise harvesting and,
although not the complete solution, they did demonstrate that cutting the tree using powered
tools was possible without detriment to its health.
The problem of mechanising harvesting of natural stands is that the land is usually uneven
and contains rocks, stumps, logs and holes. There are also, initially, other plants which, if
harvested, might contain products which would be co-distilled with the eucalyptus oil. Clearing
the site of unwanted obstacles is therefore the first task, and in many areas this is a large and

costly job. Once it is possible to operate normal agricultural machinery on the land to be
harvested the aim is to reduce the manual work to a minimum. The traditional technique of
cutting the coppice with a knife, laying the cut material in heaps, loading the heaps on to a
vehicle, transporting the leaf to the still and loading the still, has all to be done, if possible,
mechanically.
The idea of bringing the still to the area to be harvested was thus conceived and, after many
trials, a machine was developed which was strong enough to cut the mallee coppice at ground
level and elevate the material into the mobile still towed behind. Partial mechanisation was
achieved by several distillers in the late 1960s, but the first effective, fully mechanical, harvest-
ing system was set up in the mallee country near West Wyalong, New South Wales, in about
1971. Since then, virtually all the industry situated on the plains has been mechanised. A typi-
cal area of cleaned natural stands of E. polybractea, ready for mechanical harvesting, is shown in
Figure 7.1.
In the field, a forage harvester is towed by a tractor, and a series of rotating hammers with
cutting edges slice though the shrubby plants at ground level. The chopped pieces are blown up
and into the separate 3-t capacity box-shaped bin trailed behind (Figure 7.2). It takes approxi-
mately one hour to fill a bin and two to two and a half bin loads to harvest one hectare of land.
When harvesting areas near to the distillery, pairs of bins are towed to and from the site by trac-
tor. If the distances involved preclude this then each pair is transported by low loader. One man
is able to undertake the harvesting operation at each site on his own. The system has also been
adopted for other essential oil production, such as tea tree oil (from Melaleuca).
Whatever the raw material, the principles of harvesting and handling, and the subsequent
distillation, remain the same. On arrival back at the distillery, a suspended lid is lowered onto
Figure 7.1 Area of regularly harvested natural stands of Eucalyptus polybractea, West Wyalong, New
South Wales. Regrowth shown is eighteen months old and ready for harvesting (photo:
J. Coppen, courtesy of G.R. Davis Pty Ltd).

Figure 7.2 Trailer bin, which also functions as a still, packed during mechanical harvesting of
Eucalyptus polybractea, West Wyalong, New South Wales (photo: J. Coppen, courtesy of
G.R. Davis Pty Ltd).
the bin by block and tackle and securely fastened. Steam from a boiler is passed upwards through
the charge of plant material and, on distillation, the oil/water vapours are led through a duct
in the lid to a multi-tubular condenser and receiver (Figure 7.3). No lagging or double skinning of
the bin is found to be necessary, ambient temperatures being sufficiently high to prevent reflux
of vapours within the bin during distillation. Once distillation commences, it is complete in
approximately one hour. Distillation at atmospheric pressure is effective and there is no advan-
tage in distilling at either reduced or increased pressure. The whole operation can be carried out
in a fairly compact, enclosed area, designed to accommodate two bins at a time (Figure 7.4).
While one is being distilled the other, with spent leaf, can be removed and replaced by another
with fresh leaf. After distillation, the extracted leaf is returned to an area which has recently been
harvested and pulled or, in some cases, tipped out of the still. In this way it serves as a much-
valued mulch. The leaf so distilled is untouched by hand throughout the entire process.
Although eucalyptus oil is readily distilled from the foliage in quite simple apparatus, some
improvement in oil yields has been achieved by using the cohobation technique. Here, the dis-
tillate water, after removal of the non-dissolved oil, is re-introduced to the system. The only
additional water required is that needed to replace water lost by evaporation and residual water
lost when the wet charge of extracted leaf is removed. The water so circulated becomes saturated
with oil and does not dissolve any more of it. Cineole-type oils have quite low solubility in
water, even hot water, and this technique was seldom used with simple bush stills. However,
with larger stills which operate most of the year, the increase in yield with cohobation is signif-
icant. A further advantage of cohobation is conservation of water; E. polybractea is a dryland
species where water is usually limited.

Figure 7.3 Trailer bin ready for distillation of Eucalyptus polybractea. Photo shows flexible duct which
leads oil/water vapours from outlet at lid to multi-tubular condenser (photo: J. Coppen,
courtesy of G.R. Davis Pty Ltd).
Figure 7.4 Distillery of G.R. Davis Pty Ltd showing space either side of the boiler for placement of
trailer bins. Boiler uses dried spent leaf from previous distillations (photo: J. Coppen).

In the mountain country where E. dives, E. radiata and several other species are worked, the axe
gave way to a chain saw for felling the tree in the 1950s, but it was not until the late 1970s that the
idea of a mobile still of the type used on the plains was tried. A still of reasonable size mounted on
a truck is difficult to operate in the steep mountain country, and is suitable only in the less steep
areas. After felling the tree with a chain saw, or the coppice growth with a heavy knife, the branches
are fed manually into a chipper which elevates the chipped material into the still mounted on the
truck. The truck then returns to the distillery. Although still requiring some manual handling,
this partial mechanisation has reduced production costs significantly where it can be used.
To be able to produce E. dives (Type) oil competitively calls for complete mechanisation and
this, in turn, requires plantation establishment. Although in some years up to 500 t of oil was
produced from natural stands, the market was never stable enough to support the high capital
cost of establishing plantations in Australia.
Mechanised harvesting of natural stands does tend to expose the harvested area to soil erosion,
both by wind and water. In the period immediately following harvest there is no ground cover
and soil blows and washes away rapidly. Various methods of alleviating this problem have been
tried. Sowing traditional agricultural cereal crops after harvesting the leaves is sometimes prac-
tised. Establishment of a pasture, where this is possible, is effective, providing the stock are not
allowed to graze until the tree regrowth is advanced. Light cultivation across the slope is also
practised. This has the effect of collecting water, so reducing run-off and therefore erosion, and,
of course, stimulating growth. A very effective method of controlling erosion and building soil
fertility is to return the extracted leaf to the land whence it came. Considerable expense is
involved in this, but in so doing, the regrowth of the trees is stimulated, in addition to control-
ling erosion. Increased yield of leaf, and therefore oil, eventually offsets the cost of this operation.
Cultivation for oil production

The ready availability of oil-bearing eucalypts in Australian forests, and the low value and fluc-
tuating demand for the oil, made plantation development unattractive during the first century
of production. However, as the nation developed, vast areas of oil-bearing forests were cleared for
agriculture, other good areas were incorporated into national parks and reserves of various types,
and much private property became unavailable. Mechanisation, so necessary to allow competi-
tive production, was difficult or often impossible on much of the available hill country forests. It
became obvious that plantation establishment was essential if the industry was to progress.
The feasibility of plantation establishment became apparent when markets became reasonably
assured and as mechanical planting and harvesting techniques were developed. The mechanical
harvesting machines were tried and improved on upgraded natural stands and the planting
machines were developed by modification of existing planters.
The advantages of plantation production, as distinct from natural forest production, are sum-
marised below:
1 Suitable land on which to grow the required species of Eucalyptus can usually be found.
Some species grow better on land other than that on which they occur naturally.
2 Alternatively, species can be selected which are most suited to the land which is available
on an existing farm, for example.
3 Land can be chosen on which machinery can be safely used.
4 A single species can be planted if desired and at a density which can be optimised. This is
usually much greater than in natural forests, where in most cases other species are present
(sometimes to a greater extent than the one required).

5 Insects and other predators can be controlled more easily.
6 In dry country, which is usually the case with Australian production, irrigation is some-
times possible.
7 The compact nature of stands allows short hauls to the still-house after harvesting.
8 Breeding programmes to develop trees with superior growth rate, higher oil yields or better
quality oil can be established.
In Australia, the eucalyptus oil industry is moving more towards plantation produc-
tion. Plantations already established are living up to expectations and one such plantation
(E. polybractea) is shown in Figure 7.5.
Aspects of establishment
Land preparation
Land preparation is important. In most cases it is desirable to deep rip the row to be planted as
deep as the available machinery can manage to allow water and root penetration. Just before
planting, the rough surface is reduced to a smoother one on which a planting machine will work
effectively. A rotary hoe is suitable for this purpose. For E. polybractea one pass is usually suffi-
cient since, in the type of soil in which it thrives, further hoeing tends to break down the soil
structure. In dry country, planting in a groove is preferable to planting on flat land or on a
mound. In this way any surface water that becomes available is concentrated near the plant.
Layout of the plantation is also important. In particular, it is necessary to ensure that machinery
can be used between rows of trees and that the density of planting is adequate to give sufficient
Figure 7.5 Eucalyptus polybractea plantation of G.R. Davis Pty Ltd, West Wyalong, New South Wales
(photo: G. Davis).

biomass, though not so dense as to cause suppression of some trees or excess stress in very
dry conditions. In very broad terms, and subject to much variation according to actual site,
5000 trees/ha is the likely optimum density for E. polybractea.
Planting
Direct sowing of seed is not practised because of the very fragile nature of the E. polybractea
plant soon after germination. Even in good conditions, losses are too great to allow adequate
establishment. Seedlings are therefore raised in a nursery to a stage where they can stand field
conditions. In spring and summer, seeds take about three weeks to germinate (unless climate-
controlled greenhouses are used) and the seedlings are ready to plant out after a further six
weeks. In autumn and winter, at least twice this time is required. Provided water is available,
seedlings can be planted in spring and summer so that the trees are established before the first
frosts of winter.
Weeding
Control of weeds in the early stages is essential. After the trees are well established, and form a
canopy, weeds are suppressed. However, since this is a perennial crop, weeds must be controlled
after each harvest, until either the canopy is formed or the season for vigorous weed growth
is past.
In plantations with straight rows, cultivation of a strip approximately 0.5 m either side of
the trees is effective in controlling weeds. The 2 m space between cultivated strips is best left
with plants on it to prevent soil erosion. Except when the trees are quite young, and therefore
fragile, sheep can be grazed on the natural or sown pasture between the rows. There is likely to
be some damage to trees when stock graze but in most cases this is offset by the value of the
grazing. Before planting, a pre-emergence herbicide such as Goal is very effective. Cultivation
in the early stages of seedling growth and coppice regrowth, followed by sheep grazing as the
trees develop, can control weeds until there is sufficient canopy to minimise weed competition.
Pests and diseases

E. polybractea is not usually subject to serious insect attack, although a sawfly (Perga dorsalis) and
a case moth (Hyalarcta huebneri) both cause some damage. When the tree is concentrated as a
single species in plantations, or in dense natural stands from which other species have been
removed, this damage can, under certain conditions, be considerable. Occasional, serious infesta-
tion tends to occur when leaf density is high, but rarely in the early regrowth stage. Damage due
to infestation can spread very rapidly, destroying large areas of leaf within a few days if not
checked. Although the trees are defoliated and the crop is lost, the tree is not killed, and it
shoots again from the lignotuber. The case moth is difficult to destroy by chemical spraying as it
is protected by its case, except at night when it feeds. However, a very effective control method
is to harvest the area of E. polybractea under attack.
The greatest hazard which E. polybractea has to face is prolonged drought conditions. The
tree has adapted to this and survives even extreme droughts by not growing. So while almost a
whole crop might be lost in such conditions, the stock is not lost and it grows again when rain
eventually falls.
E. polybractea is subject to root fungus attack when grown outside its natural habitat, particu-
larly in wetter areas.

Table 7.1 Commercial oil yields of Eucalyptus species in Australia
Commercial yield Interval between

(% w/w, fresh basis) harvests (years)
E. polybracteaa 1.01.5 1.52.0

E. radiata, cineole variant 2.53.5 2.53.0
E. dives, cineole variant 2.54.0 2.53.0
E. dives, piperitone variant 3.04.5 3.04.0
E. viridisb 0.30.6 1.01.5
E. globulusb 0.61.1 2.03.0
a The most important species.

b Nowadays only occasionally distilled separately.
Factors which affect biomass and oil yields

It is not sensible to state quantities of biomass or oil yield per unit area for natural forest stands,
from which most Australian-produced oil originates. The number of trees per hectare varies
greatly, as does their vigour and the yield of oil, depending as they do on soil, climate and species.
There is a general consistency within a species of yield of oil per unit weight of leaf, and even
greater consistency of chemical composition. For commercial purposes, the yield of oil of any
species is usually expressed in percentage terms as the weight of oil distilled from freshly harvested
leaf material (i.e. per cent w/w, fresh basis). Leaf material is that part of the plant which is put into
the still. In the case of trees in which the branches are chopped off and then the leaves stripped from
the branches, for example, E. dives and E. radiata, the material that goes into the still consists of
leaves and terminal branchlets only. In the case of trees cut at ground level by hook or by machine,
for example, E. polybractea and E. viridis, the whole of the aerial part of the plant is put into the still.
On this basis, yields of the main commercially produced oils are shown in Table 7.1.
The figures in Table 7.1 are general and subject to considerable variation. There is variation
from district to district and even more variation with season. The cause of this rise and fall in the
yield of oil is not clearly understood, although a number of factors are involved. In the case of
E. polybractea, which is a dry-country species, the quantity of biomass produced per hectare increases
with higher rainfall, while the yield of oil in the leaf increases in dry periods. This is partially
explained by the lower moisture content of the leaf in dry times. In order to avoid the problems
of variable moisture content, and the inclusion of variable amounts of woody material in the
charge of leaf which is distilled, laboratory distillation in which the moisture content of the
leaf is known (by determination) and only leaf (including petiole) is used is the only satisfactory
means of determining oil yields. For the commercial producer, however, such methods are time-
consuming and expensive, and may yield results which cannot immediately be related to practice.
It must be noted, too, that the frequency of harvest varies with species and, to some extent,
with district. The interval between harvests is indicated in Table 7.1. Although in years of
favourable weather the trees can be harvested at shorter intervals, more frequent harvesting will
ultimately reduce the vigour of the tree. Trees which have not been harvested too frequently have
a long production life and give a sustained yield of oil. Some E. polybractea trees have been
harvested at approximately eighteen-month intervals for up to eighty years without loss of vigour.
As in natural stands, the biomass and oil yields of plantations vary greatly. Factors which
affect these yields include:
1 Seed provenance
2 Soil and nutrient properties

3 Water supply
4 Weather
5
6
Weeds
}
Discussed
Pests and diseases earlier
Seed provenance
In nature, although there is some consistency of leaf production and oil yield within a stand,
there can be variation, sometimes quite marked, between different geographical sites (prove-
nances) due to genetic differences. In addition, some individual trees within a stand may have a
particularly high or low vigour and/or oil content. Selection of seed from known, high quality
trees or provenances or, better still, vegetative reproduction, is therefore desirable in order to
maximise the returns from plantation development. To date, while vegetative propagation has
been achieved, it is difficult and much more expensive than planting seedlings. Selection of
superior trees, striking cuttings and developing a seed orchard from them remains the most
effective means of establishing high-quality plantations.
Soils
Natural stands of E. polybractea, the main source of oil in Australia, are restricted to a small area
on the central western plains of New South Wales and, disjunctively, to a larger area in central
and western Victoria. The tree grows well on hard, dry country but less well on more fertile, friable
soils. Considerable research has confirmed that the best results for biomass production are
obtained in the natural stand areas. Here, E. polybractea is often the dominant tree and sometimes
occupies the area almost exclusively in terms of eucalypts. Although the tree thrives on the low
ridges of the mallee-type country it grows best in the wide, very shallow valleys between the
ridges. The plantations established to date are in the natural stand areas.
Addition of conventional fertilisers has very little effect on the growth rate of E. polybractea
when it is grown in its natural habitat. Trials have shown that there is no useful response
to potassium or phosphorous. Indeed, growth can be retarded by heavy application of these
elements. Milthorpe et al. (1994) reported a poor response to either phosphorous or nitrogen.
Substantial application of nitrogen does tend to increase growth, but mainly of stem, with little
increase in leaf biomass. Some trials of trace elements have also shown little promise. Other than
returning extracted leaf to the harvested areas, therefore, application of fertiliser is not beneficial.
Water supply
For the dryland eucalypts, water is a major factor in determining biomass and oil yields. If
irrigation is feasible, biomass can be considerably increased if it is employed at the most appro-
priate time in the growth cycle. However, water for irrigation is seldom available in the mallee-
growing areas and it is necessary to resort to maximising retention of rainwater on plantations.
Spreading the extracted leaf on the land from which it was harvested is probably the most effec-
tive means of conserving moisture. This probably also returns some of the nutrients to the trees.
Weather
Without doubt, the major factor in biomass yield is the weather. Although irrigation reduces its
effect to some extent, biomass nevertheless increases dramatically in times of good rain, particu-
larly in springs which are followed by hot summers with sufficient follow-up rain. In mallee

species, biomass is low at the first harvest after planting, but it increases in subsequent harvests
as the coppice growth from the lignotuber produces several stems rather than just the original,
single one. Excluding the first harvest, biomass yields are likely to range from 2.5 to 15 t, and oil
yields from 30 to 150 kg, per hectare. While this very great variation is due to a combination of
the factors already mentioned, the major factor remains the weather and the climatic conditions
which prevail during the period of growth between harvests.
In a 5-ha trial plot of E. polybractea harvested annually from 1981 to 1990, the yield of oil
per hectare varied from 56 to 80 kg (G. Davis unpubl.). The highest yields were in years of
higher-than-average rainfall, while drought years resulted in lower oil yields. The lowest yield,
56 kg/ha, was in the final year of the trial; biomass was also low, despite reasonable weather con-
ditions, and this was attributed to a decline in vigour of the trees due to too short a time inter-
val between harvests. In its natural habitat of an average, but variable, annual rainfall of about
400 mm, E. polybractea is normally harvested at eighteen-month intervals. When the interval
between harvests in the trial was increased from twelve to eighteen months, and then to twenty-
one months, the oil yields were 112 kg (equivalent to 75 kg/year) and 140 kg (80 kg/year)
per hectare, respectively, that is, at the higher end of the annual range quoted earlier. However,
the confounding effect of rainfall means that there is not necessarily a simple inverse relationship
between annual yield and frequency of harvesting.
While the variation in oil yield in the trial has been substantial, variation in natural stands is
much greater and caused by such factors as differing soil properties, tree provenance, topography
(particularly in relation to water run-off) and weed and pest infestation.
Post-harvest aspects of oil production
Oil storage
After distillation, the layer of oil which is separated from the oil-water condensate remains wet.
If the oil is to be sold in crude form, without further rectification, it is therefore desirable to dry
it and for this, anhydrous calcium chloride or anhydrous sodium sulphate can be employed. The
oil can then be stored, preferably in galvanised steel drums or in high-density plastic ones. Some
plastics are affected by cineole-type oils. Although cineole-type oils do not oxidise rapidly in
contact with air, it is recommended that soon after distillation the oil be stored in airtight drums
in the shade, that is, away from excessive heat and with light excluded.
Further processing
After drying, the crude oil is usually colourless or pale yellow. In this form it can be held for sev-
eral years without deterioration, although it will eventually discolour. However, oil is often
refined by carrying out a second, separate, dry distillation after the initial distillation from the
leaf. This rectification, if undertaken, is carried out primarily to adjust the cineole content to
that required by the various standards or by the buyers, but it also removes any water and colour.
It also removes any low-boiling components of the oil, which in some oils have an unpleasant
odour. If necessary, high-boiling fractions can also be removed, although this calls for a high
temperature towards the end of the rectification process, which is undesirable. Rectification is
best carried out at reduced pressure. Rectification at moderate temperatures can also be achieved
by passing steam through the oil; this removes colour and unwanted odours, but the oil then has
to be dried. A further advantage of rectification is that it has a unifying effect, producing more
consistency in composition for different batches of oil, which most buyers require.

It is standard practice to rectify oil distilled from E. globulus because the crude oil rarely has a
sufficiently high cineole content to conform to the normal standards. E. smithii oil, imported
into Australia from Africa, is usually rectified to reduce the aldehyde content; isovaleraldehyde,
the offending chemical, is obnoxious, even in small concentrations. Although the most com-
monly produced Australian oils, those from E. polybractea and E. radiata (Type), do not need to
be rectified, in practice they are because of the demand for consistency of composition. We are in
an age where natural oils are expected to fit man-made standards, rather than standards being
established to accommodate natural oils. While this view tends to hold sway, some buyers
consider that rectification has the effect of reducing the individual character of the different oils
by removing some of the compounds which give them their unique aroma, and so reduces, rather
than enhances, the quality. E. radiata, for example, yields an oil with much more aromatic
character than, say, E. globulus.
There is a demand for eucalyptol, the trade name for virtually pure 1,8-cineole, and this is
readily obtained from E. polybractea, where the cineole content of the crude oil is high to start
with (from levels of around 82 per cent to as high as 90 per cent). However, limonene, which is
usually present to the extent of a few percent in the crude oil, has a boiling point very close to
that of 1,8-cineole, and this prevents eucalyptol being obtained solely by distillation without a
great deal of effort and expense. A two-stage procedure is therefore adopted, making use of dif-
ferences in freezing point as well as boiling point. Initial rectification is performed by distilling
the oil under vacuum and, after first removing the low-boiling components, collecting the major
cineole-rich fraction. This is then transferred to a cold store at around "30C for up to 24 h. The
resulting mixture contains mainly frozen cineole; limonene, and some other minor components,
remain liquid. The mixture is centrifuged to remove the liquid portion and the frozen part is
collected and warmed to furnish eucalyptol. Eucalyptol is hygroscopic and is usually returned to
the still for a final, careful redistillation. The end-product is 99 per cent or more pure.
Standards
For more than 100 years there has been a standard to which eucalyptus oil must conform in order
to be used for medicinal purposes. In 1914, the British Pharmacopoeia required a minimum of
55 per cent cineole and a very low content of phellandrene and aldehydes. The latter two compounds
were restricted by limit tests, without the actual percentages permitted being stated. The main
aldehyde in the cineole-type eucalyptus oils is isovaleraldehyde, already referred to above. As well
as being unpleasant itself, short exposure to air induces production of its oxidation product, isova-
leric acid, in sufficient amounts to give a rancid odour. Later, national pharmacopoeias, including
the British Pharmacopoeia, stipulated 70 per cent as the minimum level of cineole, and specific
ranges for a number of physical constants. At present, oil is sold mainly in accordance with
national pharmacopoeias or other national and international standards, all of which are similar.
Revised Australian standards for cineole-rich oils have recently been published (SA 1998),
replacing those of 1977. In addition to physico-chemical data for oils with cineole contents
within the defined ranges (7075 and 8085 per cent) there are chromatographic data and infor-
mation on flash points (see also Appendix 5). Full details are available from Standards Australia.
There is an Australian standard for E. citriodora oil (AS 2116) but it dates to about the time
that the oil was last produced in Australia, approximately thirty years ago; it is unlikely that
E. citriodora oil will be produced again in Australia.
Adulteration of the cineole-type eucalyptus oils is extremely uncommon. The general use of
chromatography in analysis makes detection of adulterants relatively easy and the present low
price and ready availability of the oil provides little financial incentive for adulteration.

End uses
Cineole-type oils
In the early days of white settlement in Australia many natural products were tried for their
general household and medicinal utility. Cineole-type eucalyptus oil was highly valued and used
for many purposes. A list of tried and tested uses of the oil, provided by Felton Grimwade &
Bickford Pty Ltd, is shown below and indicates the diversity of its applications.
Childrens colds Sauna Carpet shampoo

Head colds and influenza Wool wash Bathroom cleaner
Mouthwash Washing work clothes and Linoleum cleaner
Scalp massage nappies Leather cleaner
Muscular aches and pains Dog wash Plastic and vinyl cleaner
Rubbing or training oil Sticking plaster removal Paint brush cleaner and
Cuts and abrasions Removal of chewing gum, softening hardened paint
Insect bites paint, ball-point ink marks Telephone cleanser
Insect repellent Removal of tar marks on Toilet cleanser
Hand and skin cleaner motor vehicles Vaporiser-humidifier
Bath and foot bath additive Spot and stain remover Penetrating oil
Many of the household uses listed above have been exploited commercially and numerous
products containing eucalyptus oil are marketed (Chapter 16). The oil is also used in perfumery,
in flavouring, and in confectionery for its therapeutic value as well as its flavouring properties.
In more recent years, a boost to the use of eucalyptus oil has been achieved with the develop-
ment and marketing of eucalyptus wool wash. Although this has been used in Australia for
many years, and was usually made up in the household as required, its use was small until it was
taken up by some of the major manufacturers of cleaning products around 1985 and marketed in
a ready-to-use form. The oil in the wool wash serves three purposes: it acts as a solvent for
removing grease, it imparts a fresh clean odour to the garment being washed, and it softens the
texture of the wool.
Other oils
Eucalyptus oils of the non-cineole type were used in large quantities earlier this century for
mineral flotation (E. dives Type and E. radiata phellandrene variant) and for the manufacture of
menthol (E. dives Type) and, to a small extent, thymol. Oil is not used for these purposes now.
The production of the so-called perfumery oils has never developed in Australia and although all
the oil-bearing species occur naturally, the yield of oil from E. citriodora, E. staigeriana and
E. macarthurii is too low to enable commercial exploitation to be profitable. Only E. citriodora
oil (and to a much lesser extent E. staigeriana oil) has been produced on a commercial scale in
other countries, and this only where production costs are low.
Recently, Australian scientists discovered a eucalypt, originally designated Eucalyptus
sp. nov. aff. campanulata but now classified as E. olida, which yields an oil rich in E-methyl cin-
namate (Curtis et al. 1990). As a result, natural methyl cinnamate is now produced and mar-
keted. However, the species is confined to a remote part of New South Wales, which is not easily
accessible and which has very limited stands, so it is now grown in plantations. Unfortunately,
the market for natural methyl cinnamate is very small and, at present, further development of
plantations of E. olida is not justified.

Production of extracts other than oil from Eucalyptus
Several extractive products other than oil have been obtained commercially from eucalypts in
Australia, although the ones described below are now largely of historical interest only.
One other outlet for the waste, spent leaf arising from oil production is worth mentioning.
Apart from its use as a mulch and a slow-acting fertiliser by the oil producer himself, as has
already been mentioned, it has established a market as a domestic garden mulch through retail
outlets. However, its low value and large bulk, and consequent high transport cost, tends to
confine its sale to producers fairly close to a city or large town.
Tannin extract
Although it is no longer produced, tannin used to be extracted from the wood of E. wandoo, a
Western Australian species of Eucalyptus. Industrial Extracts Ltd, a member of the Plaimar group
of companies, extracted and concentrated tannin for about forty years until the late 1960s. The
material was used in tanning leather, particularly heavy leather. It was also used as an agent for
treating boiler-water, where it acted as an oxygen scavenger, preventing scaling by forming sol-
uble salts in preference to insoluble calcium ones, and forming a preservative iron tannate film
on the tubes of the boiler. It was also used as a mud loss preventative in oil drilling. Many thou-
sands of tonnes of these particular types of phenolic products were exported.
Rutin
Another phenolic compound, the flavone glucoside rutin, occurs in the leaves of a number of
eucalypts and was extracted on a commercial scale, particularly from E. macrorhyncha and
E. youmanii, during the 1950s and 1960s (Humphreys 1964). Rutin is used in the treatment of
capillary fragility, particularly varicose veins, haemorrhoids and frostbite. However, the econom-
ics of rutin extraction from Eucalyptus could not compete with that of rutin obtained from
Sophora japonica from China and Australian production ceased around 1970.
Eucalyptus kino
The astringent exudate produced from the trunk of many eucalypts is commonly, but erro-
neously, known as gum. It was used by early settlers as an astringent and also, later, in the wine
trade. Kino was exported to Europe, particularly France, until about 1975 when difficulties with
its collection, and a declining market, led to a cessation of production. Kino from E. camaldulensis
was the most popular.
Research and development

The Australian eucalyptus oil industry has been well served by the research institutes. Almost
from the commencement of the industry, the Technological Museum in Sydney (later the
Museum of Applied Arts & Sciences) worked on the essential oils of the native flora, particularly
eucalypts. Their research on the botany and chemistry assisted the industry to develop. Other
aspects, such as selection of the most suitable land for growing oil-bearing species such as
E. polybractea, were also investigated, particularly by B.E.J. Small of the Museum of Applied Arts &
Sciences. Some of this research has been continued at the New South Wales Department of
Agriculture. Milthorpe et al. (1994), for example, have conducted research into growth rates and

oil yields of E. polybractea under dryland and irrigation conditions. Optimum planting densities
for E. polybractea and E. kochii have also been investigated (Milthorpe et al. 1998).
Currently, much work is focused on the selection and breeding of elite trees for oil production.
Dr M.U. Slee of the Forestry Department of the Australian National University, Canberra, is
working on a project with E. polybractea. In Western Australia, work at Murdoch University,
Agriculture WA and the Department of Conservation and Land Management (CALM) is seeking
to produce elite trees for oil production from E. kochii subsp. kochii, E. kochii subsp. plenissima,
E. horistes, E. angustissima and E. loxophleba subsp. lissophloia, all Western Australian species, as
well as E. polybractea.
The Western Australian research is part of a large project aimed at reversing land degradation
in the wheatbelt. Loss of tree and shrub cover, sometimes exacerbated by the use of flood irriga-
tion, has led to a rising water table and salt-rich soils. By planting eucalypts it is hoped to reduce
groundwater recharge and thus control the salinity (Eastham et al. 1993). In choosing good
oil-bearing species it is expected that oil production, as well as residue utilisation (to produce,
for example, activated carbon and energy), will eventually defray the cost of planting and bring
in a cash return. All the species have the mallee habit, well-suited to short production cycles and
large-scale mechanised harvesting operations. Placing large quantities of oil on a traditional
market, already over-supplied, will be difficult and the project aims, instead, to penetrate the
market for industrial solvents, particularly as a natural, environmentally friendly substitute for
trichloroethane (Bartle et al. 1996, Bartle 1999). If successful, the size of the scheme (of the
order of 0.5 million ha of oil mallees) will result in very considerable quantities of cineole-type
oil being produced. However, as the project has not yet reached the first large-scale harvest stage
the production economics cannot be confirmed and its viability remains uncertain.
Commercial producers themselves have also spent much time investigating the many aspects
of plantation development including land selection, land preparation, seed selection, raising of
seedlings, planting and harvesting techniques, weed and insect control, soil and water conserva-
tion, and irrigation. A very good technique for raising seedlings of E. polybractea, using a
potting mix derived mainly from eucalyptus leaves, was developed by Constance Davis of
G.R. Davis Pty Ltd. This, together with an effective method of selecting high quality seed, has
been used to establish large plantations on the western plains of New South Wales. Mrs Davis,
in conjunction with the Department of Forestry, Australian National University, has also developed
an effective technique for the vegetative propagation of E. polybractea.
Research needs
Australia, being the home of the eucalypt, has all the oil-bearing species at its disposal. It there-
fore has the potential to be able to choose the best ones in terms of suitability for planting in a
particular part of the country and in terms of oil yield and quality. The future of the industry
depends on continued research to develop such high-yielding, high quality stock, as well as even
more efficient methods of production. Further work on vegetative reproduction will enable this
to proceed rapidly.
While, obviously, there is still much to be learnt about the botany and chemistry of the
eucalypts, and about the practical aspects of field management such as growing, harvesting and
distilling the oil, the major task facing researchers today is, without doubt, to find new uses for
eucalyptus oil. At present, world demand for this oil is easily met by the supply. Furthermore,
there are a number of countries not now contributing to the market which could produce oil if
increased demand were to develop. A new, large use is required if the industry is to develop
further. Research at Murdoch University into the use of eucalyptus oil as an industrial solvent

has already been mentioned but the very low cost of the solvents to be replaced is likely to make
this a difficult task.
Some years ago, work in Japan and Australia indicated that cineole, or high-cineole eucalyp-
tus oil, could be used advantageously with ethanol as an automobile fuel (e.g. Takeda 1982,
Barton and Tjandra 1989). Small amounts of the oil in ethanol, or a petrolethanol mix,
improve the effectiveness of the fuel. Further research on this should be done, although, even if
it is shown that there is an advantage in incorporating some cineole in the mix, it is unlikely to
benefit the eucalyptus oil industry unless there is a shortage of petrol.
Chemical research has demonstrated the preponderance in some oils of chemicals other than
the usual ones such as cineole or piperitone, and this offers the possibility of the oils being
exploited as sources of chemical isolates, providing, of course, that the chemical in question is of
commercial interest. The extraction of E-methyl cinnamate from E. olida is a recent example of
this, and E. loxophleba, which is rich in 4-methyl-2-pentyl acetate (Grayling and Knox 1991), is
currently being evaluated for its commercial prospects. However, by their very nature, such
speciality oils have limited markets in volume terms.
References
Bartle, J.R. (1999) Why oil mallee? In Oil Mallee Profitable Landcare, Proc. Oil Mallee Association Seminar,
Perth, Western Australia, March 1999, pp. 410.
Barton, A.F.M. and Tjandra, J. (1989) Eucalyptus oil as a cosolvent in waterethanolgasoline mixtures.
Fuel, 68(1), 1117.
Coppen, J.J.W. and Dyer, L.R. (1993) Eucalyptus and its Leaf Oils. An Indexed Bibliography, Natural
Curtis, A., Southwell, I.A. and Stiff, L.A. (1990) Eucalyptus, a new source of E-methyl cinnamate. J. Essent.
Oil Res., 2, 105110.
Grayling, P.M. and Knox, J.R. (1991) (R)-4-methyl-2-pentyl acetate from Eucalyptus loxophleba. J. Nat.
Prod., 54, 295297.
Grolier Society (1965) The Australian Encyclopedia, Vol. 3, The Grolier Society of Australia, Sydney,
pp. 409411.
Humphreys, F.R. (1964) The occurrence and industrial production of rutin in southeastern Australia. Econ.
Bot., 18, 195253.
Milthorpe, P.L., Brooker, M.I.H., Slee, A. and Nicol, H.I. (1998) Optimum planting densities for the
production of eucalyptus oil from blue mallee (Eucalyptus polybractea) and oil mallee (E. kochii). Industrial
Crops Prods., 8, 219227.
Milthorpe, P.L., Hillan, J.M. and Nicol, H.I. (1994) The effect of time of harvest, fertilizer and irrigation
on dry matter and oil production of blue mallee. Industrial Crops Prods., 3, 165173.
SA (1998) Oil of Australian Eucalyptus. Part 1: 7075 Percent Cineole, AS 2113.1-1998, and Part 2: 8085
Percent Cineole, AS 2113.2-1998, Standards Australia, Strathfield, Australia.
Shiel, D. (1985) Eucalyptus The Essence of Australia, Queensbury Hill Press, Melbourne.
Takeda, S. (1982) Studies of eucalyptus oil and its application to internal combustion engine. Pan-Pacific
Synfuels Conf., 2, 498508.

8 Cultivation and production of eucalypts
in the Peoples Republic of China
Shaoxiong Chen
Eucalypts as plantation trees in China
History of their introduction and cultivation

Eucalypts were first introduced into China from Italy in 1890 (Qi 1990). They were initially
planted for ornamental and screening purposes, mainly on a small scale in gardens, schools, col-
leges and scenic spots, along roads and around villages. Some very old trees, up to 80 years old,
still exist in southern China and some indication of their size can be seen from Table 8.1.
A number of distinct periods can be recognised in eucalypt domestication in China (Liu et al.
1996). Prior to 1950 eucalypts were planted in gardens and for amenity or general purpose use.
Predominant species were Eucalyptus camaldulensis, E. citriodora, E. exserta, E. globulus, E. robusta,
E. rudis and E. tereticornis but little is known of their provenance origin. Establishment of euca-
lypt plantations on a large scale only began in the 1950s, using species readily available within
China. However, severe frost damage and widespread failures occurred in sub-tropical areas due
to the use of inappropriate frost-sensitive material. Plantation species were primarily the same as
those used prior to 1950, with growth rates averaging up to 7.5 m3 ha!1 yr!1 (Wu et al. 1994).
Table 8.1 Documented data on old eucalypts in China
Species Age Height Dbh No. of Location

(years) (m) (cm) trees (province)
E. amplifolia 62 20 45 1 Guangdong
E. botryoides 62 25 70 1 Guangdong
E. camaldulensis 5076 3039 71150 7 Fujian, Guangdong
E. citriodora 5070 3040 75101 6 Guangdong, Fujian,
Guangxi, Yunnan
E. dichromophloia 70 30 88 1 Guangdong
E. exserta 50 2030 7580 2 Guangdong
E. globulus 5075 3050 110161 3 Yunnan
E. globulus subsp. 50 20 100 1 Sichuan
bicostata
E. maculata 70 30 65 1 Guangdong
E. microcorys 62 20 34 1 Guangdong
E. paniculata 6062 2030 5076 2 Guangdong
E. robusta 5866 2530 8498 4 Guangdong, Fujian
E. rudis 80 37 154 1 Fujian
E. saligna 65 30 68 1 Guangdong
E. tereticornis 6070 2035 4097 6 Guangdong, Jiangxi

The first eucalypt forest farm, Yuexi Forest Farm, was set up in Zhanjiang, Guangdong
Province, by the Southern China Bureau of Agriculture in Leizhou Peninsula, Guangdong
Province, in 1954 (Wu 1991). The main species planted were E. exserta and E. citriodora.
During the 1960s the total plantation area increased slowly towards 300,000 ha with
increments of 810 m3 ha!1 yr!1 as improved land races and better cultural techniques were
developed. The second eucalypt forest farm, Guinan Forest Farm, was founded in Guangxi
Zhuang Autonomous Region in 1963. E. exserta and E. citriodora were again the main species.
In the 1970s small-scale, rudimentary breeding programmes commenced with species and
provenance testing and the testing of land races. The plantation area increased to about
400,000 ha and increments of 1012 m3 ha!1 yr!1 became commonplace.
The period from 1981 onwards saw the greatest progress in eucalypt domestication in China
(Bai 1994). Establishment of eucalypt plantations increased substantially, with an average of
approximately 30,000 ha being planted each year. The rate has been accelerating since 1990 and
by 1995 had reached 50,000 ha yr!1, based on a survey by the China Eucalypt Research Centre
(CERC).
Present day plantations

More than 300 species of Eucalyptus have been introduced to China in the past century (Wang
and Brooker 1991), but only about a third of these have survived, of which ten species are used
in large-scale plantations: E. camaldulensis, E. citriodora, E. exserta, E. globulus, E. globulus subsp.
maidenii, E. grandis, E. urophylla, the hybrid between E. urophylla and E. grandis, E. 12ABL, and
a local land-race called E. leizhou No. 1. Several of these are used as sources of oil in China. The
taxon E. 12ABL is a land race developed from the seed introduced to China in the 1970s from
the Congo and reported to originate from a single tree in Madagascar (Eldridge et al. 1993).
E. leizhou No. 1 is a natural hybrid of E. exserta (Qi 1990). A number of other species, including
E. nitens, E. smithii, E. tereticornis, E. dunnii and E. saligna have recently shown good potential in
trials, although plantation areas of these species are relatively limited to date (Liu et al. 1996).
E. smithii is discussed later in connection with its oil.
According to estimates made by CERC in 1996, the area of eucalypt plantations now exceeds
0.92 million ha. Details of the main areas, together with intended end uses (including oil pro-
duction), are given in Table 8.2.
The plantations are distributed over 17 provinces: Guangdong, Guangxi, Hainan, Fujian,
Yunnan, Sichuan, Guizhou, Hunan, Hubei, Jiangxi, Zhejiang, Jiangsu, Shanghai, Anhui,
Shenxi, Gangsu and Taiwan (Wu 1991). The distribution extends from latitude 18 to 33N,
longitude 100 to 125E, and altitude up to 2000 m (Qi 1990). About 90 per cent of the plantation
area is concentrated in Guangdong, Guangxi, Hainan and Yunnan provinces, south of latitude
27N. By the year 2000, the Chinese eucalypt plantation area was forecast to be more than
1.3 million ha (Midgley and Pinyopusarerk 1996), with 1520 per cent of the annual planting
stock being derived from clonal seed orchard seed or from vegetatively multiplied clones.
Because of their rapid growth, ability to coppice, multiple uses and adaptability, eucalypts are
widely planted in the countryside, often by small farmers who use part of the harvest themselves
and part as a source of cash income. Some of the wood is used for timber and some for fuelwood.
Recently cropped leaves from roadside areas of E. citriodora grown for timber, and awaiting dis-
tillation, are shown in Figure 8.1. Increasing use of improved planting and management meth-
ods has enabled short rotations of 810 years to be shortened still further.
Apart from oil production and extraction of tannins (Table 8.2), non-wood uses include
extraction of phytohormones from the leaves of some species for horticultural applications and

Table 8.2 Areas under plantation and utilisation of main eucalypt species in China (1996)
Province Main species Area (ha) Utilisation
Guangdong E. camaldulensis, E. citriodora, 400,000 Wood chips, plywood, particle

E. exserta, E. leizhou No. 1, board, fibre board, charcoal,
E. 12ABL, E. urophylla, oil, tannins
E. urophylla " E. grandis
Hainan E. citriodora, E. exserta, 187,000 Wood chips, plywood, particle
E. 12ABL board, fibre board, oil
Guangxi E. citriodora, E. exserta, 170,000 Wood chips, plywood, particle
E. leizhou No. 1, E. urophylla, board, fibre board, oil
Yunnan E. globulus, E. globulus subsp. 147,000 Oil, plywood, particle board,
maidenii fibre board
Sichuan E. globulus, E. globulus subsp. 13,000 Oil, firewood
maidenii, E. robusta
Guizhou E. globulus, E. globulus subsp. 3000 Oil, firewood
maidenii
Hunan E. camaldulensis 2000 Firewood
Figure 8.1 Eucalyptus citriodora leaves awaiting distillation, Leizhou Peninsula, Guangdong Province
(photo: S. Chen).
honey production from bees that feed exclusively on Eucalyptus flowers (Zheng 1988). Again, for
some families, such activities are a much valued means of income generation. As multipurpose
trees, some eucalypts are used in agroforestry. On Hainan Island, for example, E. exserta
and E. citriodora are interplanted with pineapple and in southwest China E. globulus is planted
alongside tobacco and sweet potato.

Table 8.3 Eucalyptus species used for four-around planting
Species Province
E. camaldulensis, E. citriodora, Guangdong, Guangxi, Fujian

E. exserta, E. robusta, E. rudis
E. camaldulensis, E. globulus, Yunnan
E. globulus subsp. maidenii
E. botryoides, E. camaldulensis, Sichuan
E. robusta
E. camaldulensis, E. tereticornis Jiangxi
E. camaldulensis, E. robusta Zhejiang, Hubei, Hunan
E. camaldulensis, E. cinerea, Shanghai
E. gunnii
Four-around plantings
The term four-around plantings refers to the trees which are planted as shelterbelts along roads
and ditches, and around villages and houses (Qi 1990). The main species used in this way are
listed in Table 8.3 and include some oil-bearing ones.
Plantings amount to over 1.8 billion trees (Wu 1991), of which over half are in Yunnan and
Sichuan provinces. However, eucalypts are not naturally good shelterbelt trees because of their
branch shedding habit which permits the wind to blow under the crowns of single rows of trees.
It is therefore necessary to plant them as several rows. The trees do not cast a heavy overhead
shade but provide a good side shade throughout the year. Another reason for planting eucalypts
alongside roads and railways is to reduce noise.
Silviculture
Although some research is now being focused on the dual-purpose management of eucalypts for
oil and wood production (see below), most Chinese eucalyptus oil is produced from waste leaf
resulting from thinning or felling of trees grown primarily for timber, pulp or other wood use.
Several of the important plantation species (E. citriodora, E. exserta, E. globulus and E. globulus
subsp. maidenii) also happen to be useful sources of oil and the leaves can be collected for distil-
lation whenever it is worthwhile to do so.
In some cases, eucalypt plantations are coppiced and harvested again at intervals of 47 years.
Timber from these crops is mostly small in diameter with a low value per unit volume.
Substantial added value is only obtained when it is processed into paper and other reconstituted
products.
Establishing a productive plantation requires good seedlings of suitable species, adequate site
preparation, sound planting methods, effective weed control and a satisfactory nutritional status
in the soil.
Nursery techniques
Seed is usually collected from seed orchard and seed production areas. Sometimes it is obtained
from phenotypically outstanding trees. Nursery techniques have changed significantly in recent
years and simplicity and cheapness have given way to more efficient and productive methods.
The advantages of container planting using plastic tubes and pots have been recognised, namely,
lower cost, greater survival rate (due to the greater volume of soil in which the roots of the young

Table 8.4 Examples of container sizes and standards of Eucalyptus seedlings
Species Tube size Length of seedling Height Diameter at Survival

(cm) stage (days) (cm) base (mm) (%)
E. leizhou No. 1 14 " 3.5 6080 1530 1.53.0 95

E. citriodora 14 " 3.5 6080 1530 1.53.0 95
E. globulus 11 " 7 7090 2025 $3.0 80
E. globulus subsp. 11 " 7 7090 2025 $3.0 80
maidenii
seedlings can grow) and avoidance of damage to seedlings through careless picking out. This
permits the planting operation to be carried out over a reasonably long season. Seed is normally
sown to a soil bed. When the seedlings are in the second or third leaf-pair stages they are trans-
ferred to containers.
The size of the containers is important. The more room in the container, the more medium
can be used, and this gives the seedlings better conditions for growth in the nursery and early
stages after planting. However, it is then heavier for transporting and handling. The medium
used depends very much on what is available locally. Two examples are 53 per cent burned soil
#41 per cent organic matter #6 per cent phosphorous (applicable to seedlings) and 75 per cent
deep yellow soil #25 per cent peat soil (cuttings). Examples of container sizes and standards for
seedlings of four Eucalyptus species are shown in Table 8.4. The information is taken from the
Leizhou Forestry Bureau and Yunnan Forestry Academy.
To protect the seedlings and cuttings from excessive sunlight and storm rains, different types
of shade are used for raising them. The shade density is about 5070 per cent. Many nurseries
also require some protection from the wind, especially in coastal regions. Artificial screens are
sometimes erected at right angles to the prevailing winds or live hedges are used. Facilities for
watering are essential in the nursery and for large ones this may be done automatically. Watering
twice a day, morning and evening, is desirable.
Establishment
When the planting area has an old crop of trees and shrubs on it which have no value, they need
to be cleared before ploughing can begin. In Guangdong and Guangxi, tractors are used to assist
in this task but in Yunnan, where the planting is in mountainous areas, the work is usually done
manually. When the area to be cleared for planting is an earlier eucalypt plantation the old
stumps are dug out or killed in order to avoid any coppicing. There is a very considerable vol-
ume of stump wood below the ground in these areas and it is recovered by the local people for
use as fuel for cooking or for making charcoal.
Land preparation is a very important step in planting eucalypts. In Guangdong, Guangxi and
Hainan, ripping, ploughing and disc harrowing of the site are generally carried out. The depth
of ploughing is normally 30 cm. Planting holes are then prepared, usually 30 " 30 " 30 cm in
size. However, in Yunnan, where the sites are stony or very steep, complete cultivation is
impracticable. Normal practice is to prepare a soil ditch, 60 " 60 cm (Zhang, Su and Dai,
unpubl. 1996), and then make a planting hole at least 50 " 50 " 40 cm, preferably larger. This
has proved to be very good for E. globulus and E. globulus subsp. maidenii growth.
A wide range of initial spacings has been used, depending on the planting site and the
intended end-use for the eucalypts. In general, poor sites have wider spacings and good sites
closer spacings. Some examples are given in Table 8.5.

Table 8.5 Spacings used for four species in the main eucalypt provinces
Species Initial spacing (m) Stocking density Utilisation Province

(stems/ha)
E. leizhou No. 1 1 " 1 " 3 or 1 " 1.3 " 2.7 5000 Pulpwood Guangdong
1.5 " 4 or 1.5 " 3 1667 or 2222 Pulpwood Guangxi
E. citriodora 1 "3 3333 Pulpwood Guangdong
1.5 " 4 or 1.5 " 3 1667 or 2222 Sawlogs, oil Guangxi
E. globulus 1 "2 5000 Oil Yunnan
1.5 " 2.5 or 1 " 4 2667 or 2500 Pulpwood, Yunnan
sawlogs
E. globulus subsp. 1 "2 5000 Oil Yunnan
maidenii 1.5 " 2.5 or 1 " 4 2667 or 2500 Pulpwood, Yunnan
sawlogs
Table 8.6 Fertiliser regimes used in the main eucalypt provinces
Province Fertiliser regime
Guangdong 1.52.5 kg organic matter #75 g NPK (1 : 2 : 2) per

plant basal dressing; 50 g NPK in 2nd and 3rd years
Guangxi 200 kg NPK (2 : 1 : 1) per ha basal dressing; 150 kg
NPK in 2nd and 3rd years
Yunnan 5 kg organic matter #510 g B per plant basal
dressing; 50 g N in 2nd year
In order to promote uniform growth and facilitate mechanical tending and harvesting, the
lines of trees should be regular and straight and the spaces between them even. This is achieved
by use of a planting chain which has markers along it at the same intervals as the required spac-
ing. The planting holes are indicated on the ground by lime. Planting is usually done in the wet
season so that the plants can take full advantage of the rains in summer rainfall regions. The
seedling should be planted firmly in the ground without air space around or below its roots, and
the field soil should be in contact with the roots. Plastic containers are removed before planting.
In most sites, young eucalypts respond quickly and generously to fertilisation. It is common
practice to apply fertiliser a few days before planting (basal dressing) and twice more thereafter.
The amount of fertiliser used and the balance between the different elements is determined by
weighing the increased yield against the cost of the fertiliser and its application on a particular
type of soil. Examples are given in Table 8.6.
Control of weed growth is greatly helped by good site preparation but there are likely to be
many weed seeds in the soil and other seed will blow in from outside. Before the closure of the
canopy, therefore, weeds are controlled by disc harrowing, hand pulling or hoeing.
Management of coppice crops

The first-rotation crop is normally felled at 510 years. The way in which the felling is carried
out, the type of equipment used, and the period during which it is done are all key factors in the
survival and well-being of the plantations through successive coppicing. Experience in Guangxi
has shown that better results are obtained with the use of chain-saws than axes, while in
Guangdong axes have been reported to give better results than the bow-saw and the two-man

crosscut saw. The felling period should be planned to avoid dry periods; in Guangdong province
it is from October to March.
The height at which the cut is made is important. If the stool is too high the chances of sur-
vival are lower but if the cut is at ground level then the bark is loosened. The recommended
height is about 5 cm. The cut should be made as smooth as possible and slanted so as to facilitate
water run-off. The accumulation of water on the stool increases the risk of fungal attack.
In most cases a number of shoots develop on each stool, although these are likely to be
reduced to six or seven by mutual competition. When the coppice shoots are about 6 months old
they are thinned to two or three stems per stool, the main selection criteria being form, wind
firmness and vigour. The final number of stems per hectare retained in the thinned coppice crop
is not less than the original stocking.
Tree improvement
Bai (1992, 1994) has summarised the problems of eucalypt improvement in southern China and
discussed issues relating to breeding strategies, use of hybrids (see also Wu et al. 1996), clonal
forestry, etc. However, during the last two decades considerable progress has been made in euca-
lypt domestication and eucalypt improvement in China, much of it with Australian assistance
(Anon. 1989, Midgley and Yang 1992, Brown 1994). New base/breeding populations have been
assembled, clonal seed orchards established, inter- and intra-specific controlled pollination tech-
niques developed and vegetative propagation techniques improved. Species and provenance test-
ing has continued and traits currently of major importance in selection work include growth,
wind firmness, disease resistance, cold tolerance and wood quality. Research aimed at identifying
high-yielding oil species and developing improved germplasm for oil production is discussed in
more detail below.
Pests and diseases

At present, our information on the pests and diseases of Eucalyptus in China (as well as those
which affect other tree crops) is limited. Pests of Eucalyptus are not too serious but the main ones
are listed in Table 8.7 (Gu and Chen 1988).
The diseases usually occur in the nursery and in the roots of the plant and can sometimes cause
serious damage in plantations. The main diseases of eucalypts in China are listed in Table 8.8
(Gong and Ke 1988).
Table 8.7 Main pests of eucalypts in China
Pest Host
Carea subtilis (Lepidoptera: Noctuidae) E. citriodora

Dappula tertius (Lepidoptera: Psychidae) E. citriodora
Acanthoecia laminatia (Lepidoptera: Psychidae) E. citriodora
Pelochrista sp. (Lepidoptera: Tortrichidae) Leaf of all kinds of eucalypts
Tarbinskiellus portentosusb (Orthoptera: Gryllidae) All kinds of eucalypts
Adoretus sinicus (Coleoptera: Scarabaeidae) E. camaldulensis, E. 12ABL
Anomala cupripes (Coleoptera: Scarabaeidae) E. camaldulensis, E. citriodora
Anomala corpulenta, A. chamaeleon Leaf/root of all kinds of
(Coleoptera: Scarabaeidae) eucalypts
a Syn. Chalia laminati.

b Syn. Brachytrupes portentosus.

Table 8.8 Main nursery and root diseases of eucalypts in China
Pathogen Host
Nursery diseases
Fusarium sp. E. citriodora, E. gunnii, E. robusta,
E. leizhou No. 1, E. leptophleba
Macrophomina phaseolina E. citriodora, E. exserta, E. globulus,
E. globulus subsp. bicostata, E. gunnii,
E. pauciflora, E. robusta
Sclerotium rolfsii E. citriodora, E. exserta
Botrytis cinerea E. saligna
Root diseases
Pseudomonas solanacearum E. grandis, E. saligna, E. urophylla,
Agrobacterium tumefaciens E. citriodora, E. exserta
Verticillium albo-atrum E. citriodora, E. exserta
Ganoderma sp. E. exserta, E. robusta
Fomes sp. E. robusta
3000
2500
2000
Exports (t)
1500
1000
500
0
1983 1984 1985 1986 1987 1988 1989 1990
Year
Figure 8.2 Exports of eucalyptus oil from China, 19831990.
Eucalyptus oil production
Brief history of the industry

The eucalyptus oil industry first developed in 1953 in Guangzhou, Guangdong Province (Song
1991). This immediately became an important channel for cash income in rural areas of
Guangdong and Guangxi. In the 1960s, the first large commercial eucalyptus oil operations in
China started in Leizhou Peninsula, Guangdong Province (Qi 1990). By the 1970s, annual pro-
duction of eucalyptus oil was about 3000 t, of which 30 per cent was exported. In the 1980s
these figures increased to 4000 t, of which 50 per cent was exported. During the 1990s, produc-
tion remained the same but the proportion which was exported rose to around 80 per cent.
Exports of eucalyptus oil for the period 198390 are shown in Figure 8.2 (Zhang 1997). China
is the worlds largest producer and exporter of both medicinal (mainly E. globulus) and perfumery
(E. citriodora) oils.

In the last 1015 years, Yunnan has become the focus of essential oil production in China.
The topography and range of climates found there gives rise to a wide variety of native flora,
many of which yield essential oils, and enables some species of exotic plants such as eucalypts to
flourish (Cu 1988). With a rich and diverse raw material base to support it, primary production
of essential oils has gradually progressed to value-added processing such as fractionation and the
production of absolutes, concretes and other types of extract. Research centres aimed at devel-
oping in-house capabilities in processing and formulating essential oils, including eucalyptus
oil, have been established, particularly in and around Kunming.
Typically, eucalyptus oil distilled by small farmers from E. globulus using fairly rudimentary
equipment is either sold to local shops or traders or transported to Kunming for redistillation
through a fractionating column. This removes both the lower boiling monoterpenes and, after
collection of the desired cineole-rich oil, the high-boiling residue. The latter contains a complex
mixture of oxygenated monoterpenes and sesquiterpenes and has, itself, the potential for further
exploitation (Zhao et al. 1997).
Eucalyptus species used for oil production

The principal species used for oil production in China are listed in Table 8.9, together with oil
yields and an indication of typical abundances of the main constituents of the oils (Zhang
1997). Of the medicinal type, E. leizhou No. 1 produces an oil of relatively poor quality (low
1,8-cineole) and in low yields but its widespread occurrence accounts for its use as a source of oil.
E. exserta also yields an oil with a relatively low cineole content (Chen et al. 1983, Zhang 1997).
E. globulus is the source of most Chinese eucalyptus oil. E. citriodora and E. dives are the sole
sources of perfumery and industrial oils, respectively.
Biomass and oil yields on a per hectare basis for four of the species given in Table 8.9 are
shown in Table 8.10 (Qi 1990). The data represent typical trees managed for commercial pro-
duction. E. globulus is the best of the medicinal oil species. Research has demonstrated some sea-
sonal variation in oil yield within the leaves (Table 8.11), although for the five species reported
by Song (1991) the pattern is not consistent.
Table 8.9 Principal Eucalyptus species exploited for leaf oil in China
Species Oil yield a Main constituent Province

(%) (relative abundance, %)
Medicinal oils
E. globulus 0.41.7 1,8-Cineole (6075) Yunnan, Sichuan, Guizhou
E. globulus subsp. 1.52.3 1,8-Cineole (75) Yunnan, Sichuan, Guizhou
maidenii
E. smithii 2.43.0 1,8-Cineole (7584) Yunnan
E. exserta 0.60.8 1,8-Cineole (3540) Guangdong, Guangxi, Hainan
E. leizhou No. 1 0.4 1,8-Cineole (2038) Guangdong
Perfumery oils
E. citriodora 1.51.7 Citronellal (8090) Guangdong, Guangxi, Hainan,
Fujian
Industrial oils
E. dives 4.7 Piperitone (52) Yunnan, Fujian
%-Phellandrene (20)
a Fresh weight basis (averages of different sites).

Table 8.10 Biomass and oil yields of four Eucalyptus species
Species Harvest (age, yr) Biomass yield a Oil yield

(t ha!1 yr!1) (kg ha!1 yr!1)
E. globulus Thinning (68) 3060 450900

E. globulus subsp. Thinning (17) 1530 300600
maidenii
E. exserta Final felling (1015) 1522.5 105157.5
E. citriodora Nursery methodb 75 900
Coppice methodc 15 180
Final fellingd (15) 7.5 90
a Fresh weight basis (leaf #twigs).

b 10,000 trees/ha harvested many times a year.
c 1667 trees/ha harvested twice a year.
d 1667 trees/ha.
Table 8.11 Seasonal variation in oil yields (%)a
Species Spring Summer Autumn Winter
E. globulus ? 1.25 ? 1.13

E. globulus subsp. ? 1.50 ? 1.30
maidenii
E. exserta 0.62 0.62 0.56 0.56
E. leizhou No. 1 0.43 0.61 0.57 0.62
E. citriodora 1.34 1.84 1.75 1.96
a Fresh weight basis (distilled from leaf #twigs).
In recent years the potential of E. smithii as an important species for oil and fuelwood production
has become clear from the results of species and provenance trials in the southern subtropical
regions of China (Wang and Wang 1991, Zheng et al. 1994, Wang 1997). Its outstanding per-
formance in terms of leaf biomass is already taken advantage of in South Africa, where it
has been grown specifically for oil production for many years. Wang and Wang (1991) investi-
gated the growth and above-ground biomass production of E. bakeri, E. dives, E. globulus,
E. macarthurii, E. radiata and E. smithii at a site in central Yunnan. After two years under inten-
sive management, growth and biomass yields (both leaf and stem/branch wood) were best for
E. smithii and E. globulus. Oil yields (in the leaf and per hectare) and oil quality (composition)
were also determined and are shown in Table 8.12, together with fuelwood yields. E. smithii and
E. globulus again performed best in terms of wood production although the high yield of oil in
the leaf of E. radiata overcame its slightly inferior leaf biomass to give it the highest yield of oil
per hectare. As a dual-purpose crop for oil and fuelwood, E. smithii and E. globulus have great
potential and the former species may come to be much more widely planted in China than it is
at present.
The potential of E. smithii for oil production has been recognised by CERC who have devel-
oped a breeding programme for it. Progeny trials were established in 1995 in Yunnan, Sichuan
and Fujian, with 100 families in each trial. Plus trees for leaf oil will be selected from these
trials in the next few years. Further tests on the plus trees and the deployment of genetically
superior trees will then be carried out.

Table 8.12 Leaf oil/fuelwood yields and oil composition of six Eucalyptus species tested in Yunnan
(after Wang and Wang 1991)
Species 1,8-Cineole Oil yield a Oil yield Fuelwood yield a

content, relative (%) (kg ha!1) (t ha!1)
abundance (%)
E. smithii 81.7 4.9 349.2 14.6

E. globulus 63.5 &1.6 291.6 13.4
E. radiata 44.7 9.1 396.0 5.6
E. bakeri 90.6 8.8 295.2 3.2
E. dives 45.1 10.1 234.9 5.4
E. macarthurii 2.0 81.6 9.0
a Moisture-free basis.
Figure 8.3 Village-scale steam distillation of Eucalyptus globulus, near Chu Xiang City, Yunnan
Province (photo: S. Midgley).
Distillation practice
Distillation of eucalyptus oil from the leaves follows the basic principles of steam distillation
which have been described earlier in some detail (Chapter 6). The traditional type of distillation
commonly practised in China is briefly described here.
Most of the stills in China are of the above-ground type in which the vessel stands on the
ground and water below the charge of leaf is fired directly. The design is simple and suitable for
field distillation on both a small and relatively large scale of production. Stills of this type are
still used in Guangdong, Guangxi and Yunnan today. An example of village-scale steam distil-
lation of E. globulus is shown in Figure 8.3.
The firebox for heating the water consists of a tank resting on a low brick wall on three sides,
with one side left open. The wall is about 50 cm high. Wood is the most suitable, and normally

the most abundant, fuel available. Spent leaf from previous distillations, once dried, can also be
used. The still rests over the firebox and comprises a tank with a cover and a screen in the mid-
dle, on which is loaded the leaves. The leaf material is hand cut by the farmers and packed so as
to completely fill the available space. The tank is constructed from mild steel sheets, about
24 mm thickness for the walls and heavier (5 mm) for the floor. Water is contained in the tank
below the screen. When the wood or spent leaf in the firebox has been lit and the water has
boiled, steam passes upwards through the fresh charge and distillation commences. The hot
mixture of oil vapour and steam is led from the top of the still through a small pipe to the con-
denser. The latter is a pipe approximately 40 45 m long which runs from the still to a large
body of water. The cooled, condensed distillate is then collected in an open drum of 60200 l
capacity, where the oil and water are allowed to separate. The oil is taken off and stored and the
water passed back to a constant level tank.
Medicinal and aromatic uses of Eucalyptus in China
Eucalyptus oil
Medicinal oils
The active therapeutic agent and the principal constituent of medicinal-type eucalyptus oils is
1,8-cineole. The medicinal quality of the oil is specified by minimum standards which are
defined in different factories. They require a medicinal oil to contain not less than 70 per cent
cineole, the same as the Chinese Pharmacopoeia (PPRC 1992), and to be practically free of
%- and '-phellandrene. Other requirements of the Chinese Pharmacopoeia are a relative density
within the range 0.8950.920 and a refractive index within the range 1.4581.468. The limit
on heavy metals is 10 ppm.
Although many species of Eucalyptus contain 1,8-cineole in their oils, only a limited number
are suitable for commercial exploitation; they combine a composition high in 1,8-cineole with
consistently high total oil yields. Although most eucalyptus oil is genuinely derived from
Eucalyptus, the Chinese Pharmacopoeia (PPRC 1992) defines it as the volatile oil obtained by
steam distillation from the plants of Eucalyptus globulus Labill. (Fam. Myrtaceae), Cinnamomum
camphora (L.) Sieb. (Fam. Lauraceae) or other plants belong[ing] to the same genus of these two
families. Cineole-rich camphor fractions are therefore permitted although, in practice, it is
believed that the use of C. camphora as a source of eucalyptus oil has declined in recent years.
Examples of Chinese medicines containing eucalyptus oil are shown in Table 8.13. Others
include An Ye Tang, Shi Di Shui, Qi Wen You, Qin Liang You and Zhi Ke Tang. People usually
buy the ready-made formulations from a traditional medicine shop or general store.
Perfumery oils
The lemon-scented gum, E. citriodora, is rich in citronellal. Although citronellal itself has lim-
ited use as a perfume, it is a valuable intermediate for the production of other fragrances. A few
other Eucalyptus species contain oils which might be considered for perfumery purposes but
E. citriodora is the only one ever to have been exploited in China on a large scale.
Industrial oils
So-called industrial eucalyptus oils contain piperitone and %-phellandrene as their main con-
stituents. Phellandrene-rich oils are used exclusively for scenting of inexpensive disinfectants,
industrial liquid soaps, insecticides and flavouring agents.

Table 8.13 Examples of Chinese medicines containing eucalyptus oil
Chinese name English name Ingredients Uses
Bai Hua You White Flower Winter green oil (40%), menthol Headache, nasal
Embrocation crystals (30%), eucalyptus oil congestion, muscular
(18%), lavender oil (6%), pain, stomach-ache,
camphor (6%) abdominal pain,
antiseptic, travel
sickness, insect bites
Feng You Jing Medicated Oil Menthol, eucalyptus oil, Headache, toothache,
methyl salicylate, eugenol, inflammation,
camphor mosquito bites
Fu Biao Qu Feng You Axe Brand Menthol crystals (20%), Headache, rheumatic
Universal Oil eucalyptus oil (15%), methyl pain, stomach-ache,
salicylate (15%), other essential colic, giddiness, travel
oils (12%), camphor (5%) sickness, insect bites
Si Ji Run Hou Pian Even-Cooling Menthol crystals (0.001 g), Pharyngitis, tonsillitis
Throat Tablets tangerine (0.001 ml), eucalyptus
oil (0.0008 ml), peppermint
(0.0007 ml), glucose, citric acid
Eucalyptus leaves
Parts of the plant, usually the leaves, are often used in traditional Chinese medicines and E. robusta
and E. saligna have been found to be particularly valuable. Qi (1990) cites three examples:
1 Disinfectant Boiled water of the leaves of E. robusta is used as a disinfecting agent in place
of ethyl alcohol after operations. Up to 1970, approximately 100,000 people had been
treated in this way at Guangzhou Military Hospital.
2 Treatment of dysentery In 1973, using Chinese medicines containing E. saligna leaves,
100 dysentery patients at a military hospital made a full recovery.
3 Treatment of nephritis Also in 1973, 115 patients were treated with Chinese medicines
containing E. robusta and E. saligna leaves. Of these, 70 made a full recovery, 25 a partial
recovery and 20 were unaffected.
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pp. 116122.

eucalypts in Africa
Paul A. Jacovelli
Historical review
Introduction of eucalypts to Africa

Settlers, missionaries and government officials introduced eucalypts to Africa in the early nineteenth
century. The first recorded introduction was in 1828 when the newly appointed Governor of the
Cape Colony brought with him from Mauritius nine Eucalyptus globulus seedlings. Progeny from
these blue gums in the Governors garden soon found their way to other parts of South Africa.
Many other eucalypt species were introduced from Australia to South Africa from around 1860
onwards. The rapid growth, adaptability to a wide range of site conditions and diversity of end
uses of the eucalypts encouraged their rapid spread into other parts of Africa. Today, eucalypts are
part of the landscape of virtually every African country.
E. globulus was for many years the most important eucalypt species in Africa but its use
declined due to its susceptibility to premature die-back (often drought related) and the atten-
tions of the eucalyptus snout beetle (Gonipterus scutellatus Gyll.), a pest accidentally introduced
from Australia. The species is still successful, however, at high elevations in cool, tropical cli-
mates such as is found in Ethiopia. The continents main commercial species are now E. grandis
(often confused with E. saligna) on the more fertile sites, E. camaldulensis in drier regions,
E. gomphocephala in the sandy, arid North African countries (e.g. Libya, Morocco and Tunisia) and
E. robusta in tropical regions (e.g. Madagascar) (Poynton 1979, FAO 1981).
Scale of plantings and end-use

Most of these early eucalypt plantings in Africa were around homesteads and farms for fuelwood
and pole production, for use as windbreaks and for their ornamental value. The commercial
potential of eucalypts in Africa was soon recognised, however, and by the late nineteenth century
plantations were being established to meet not only escalating household needs, but also a
rapidly expanding industrial requirement (e.g. for the production of pit props for the gold mines
of South Africa and to fuel the railways of Angola). By the early 1900s, the planting of eucalypts
was rapidly expanding throughout Africa, principally for fuelwood and for the protection of
fragile lands. In the latter half of the twentieth century, there was a huge expansion of eucalypt
planting for hardwood pulp and sawn timber. Large and small-scale eucalypt plantations (private
and state-owned) are now a very important part of many African countries economies.
Estimates of the eucalypt plantation area in Africa vary markedly due to the difficulties of
obtaining reliable (or recent) figures from a number of countries. Pandey (1995) estimated that
in 1990 tropical African countries alone had 790,000 ha of eucalypt plantations, the principal

countries being Angola (135,000 ha), Madagascar (130,000 ha) and Ethiopia (95,000 ha).
Eldridge et al. (1993) estimated Ethiopian plantations at over 250,000 ha. Outside the tropical
areas there are extensive eucalypt plantations in some Northern and Southern African countries
for example, Morocco (200,000 ha), Tunisia (42,000 ha), Algeria (30,000 ha) and South Africa
(538,000 ha) (Davidson 1995). Davidson (1995) estimated a total of 1,636,000 ha of eucalypt
plantations in Africa in 1990. A full list of African estimates for 1990, together with more
recent data (1995), is given in Appendix 2.
Eucalyptus oil production in Africa

There is very little recorded information concerning the use of eucalypts in Africa for their essen-
tial oils, though it is likely that local people quickly discovered the therapeutic value of the
leaves of certain species. South Africa was probably importing eucalyptus oil from the late nine-
teenth century (Shiel 1985). Poynton (1979) refers to two publications which indicate that there
was an interest in eucalyptus oils in South Africa by the 1930s (De Villiers and Naud 1932,
Van der Riet 1933). From the range of species tested they concluded that there was potential in
South Africa for the production of the three main types of eucalyptus oil, namely, medicinal,
industrial and perfumery oils.
Obtaining information about the oil industry in Africa is difficult undoubtedly due to the
competitive nature of the business, with the key private growers closely guarding the details of
their operations. The first distillation of eucalyptus oil in Africa probably took place using crude
stills and the leaves of E. globulus trees harvested primarily for timber or fuelwood. The first
African plantations dedicated to the production of eucalyptus oil were probably established
around the early 1940s in the Democratic Republic of the Congo (formerly Zaire), Rwanda and
Burundi. These Central African countries were producing cineole-rich oil from E. globulus,
E. smithii, E. globulus subsp. maidenii and E. dives, as well as other types of oil from E. citriodora
and E. macarthurii. By 1957, these operations were producing 80 t of oil annually (Penfold and
Willis 1961, Weiss 1997).
Around the early 1950s, oil plantations were being established on private farms in the high-
veld region of South Africa and in neighbouring Swaziland. Both cineole and industrial oils were
being produced from these plantations: cineole-rich oil mainly from E. smithii and E. radiata,
and industrial oils from the piperitone-rich variant of E. dives and the phellandrene-rich variant
of E. radiata. The total area of plantations dedicated to eucalyptus oil production in South Africa
and Swaziland was around 4000 ha by 1990, with over 80 per cent of the area being worked on
a short-rotation coppice system. An estimated 470 t of oil per year was being produced in the
late 1970s (245 t of cineole-rich oil and 225 t of piperitone-rich oil) (Small 1981). Coppen and
Hone (1992) estimated that in 1991, approximately 255 t of cineole-rich oil was produced in
Southern Africa (representing over 9 per cent of total world production), with some rectification
capability in South Africa. Oil production was often on a stopstart basis, depending on the oil
price. The majority of the distilled oil was exported to Australia and Spain for rectification,
though there always was (and still is) a small local market for both types of oil.
Plantations of E. smithii are believed to have been established in Malawi and Angola for cine-
ole production but little is known of their fate or whether commercial quantities of oil were ever
produced. Civil wars in Angola and the Central African countries over the past thirty years or so
will undoubtedly have severely affected any eucalyptus oil operations which existed. More
recently, private growers in Zimbabwe have grown E. smithii and E. cinerea on a short-rotation
coppice cycle, also for cineole (Poynton 1979, Boland et al. 1991). Oil production began there in
1989 but it is not known whether this is continuing today. Also in the late 1980s, a company in

the Eastern Highlands of Tanzania conducted trials with oil species and was planning to produce
cineole from E. smithii on a significant scale.
The economic climate in the late 1980s and 1990s poor oil prices and rising production
costs meant either that full scale oil production never materialised (in the case of Tanzania) or
that some production ceased (as in Swaziland). In South Africa, the area of eucalypt plantations
dedicated to oil has now reduced to approximately 1800 ha, most of the reduction occurring in
E. smithii. One estimate puts the production split at about 1 : 2 for cineole : piperitone-type oils
(V. Davidson pers. comm. 1998).
Species and provenance selection of oil-bearing eucalypts
Introduction
Successful oil production operations in Africa have been largely based on plantations cultivated
with the primary objective of oil production. These plantations, particularly in Southern Africa,
are managed intensively with the aim of maximising oil yields. Other products produced, such
as poles and firewood, are seen as useful by-products and utilised (or sold) where possible. These
oil plantations have mostly been managed on a short-rotation, coppice system. Dual-purpose
plantations for wood and oil production have been used to a lesser extent in Africa, though
this technique could make the business more appealing to small growers.
The information provided below is based largely on work carried out in the late 1980s and
early 1990s at Shiselweni Forestry Company in Swaziland. Working in collaboration with the
Natural Resources Institute (Chatham, U.K.), research in Swaziland was aimed at increasing
the sustainable yield of cineole-rich oil from the plantations. Matters investigated included the
optimisation of source material through species and provenance research, the influence of other
factors such as fertiliser application, rotation and seasonal effects on oil yield, field management
practices (e.g. spacing, harvesting and transport methods) and distillation conditions (Coppen,
Milchard unpubl., Jacovelli 2002).
Species characteristics
This section discusses the main eucalypt species used commercially for the production of oil in
Africa and those introduced on a trial basis. It must be stressed that whilst research conducted
elsewhere provides some indication of what might grow well in a particular area, there is no
substitute for performance trials in a region prior to any large-scale plantings for eucalyptus oil
production.
Table 9.1 shows the oil characteristics of those species which are, or have been, used for
oil production. Yield and compositional data should be regarded as illustrative and not
necessarily representative. Dethier et al. (1994), for example, in Burundi, only sampled single
trees.
E. smithii
On favourable sites where it has been cultivated in Southern and Central Africa, E. smithii has
often produced higher biomass yields (wood and foliage) than other eucalypts. It appears to be a
fairly consistent species throughout its natural range with regard to oil yield and cineole con-
tent, though there is some variation between and within provenances in terms of other factors,

Table 9.1 Yields and characteristics of leaf oils obtained from eucalypts growing in Africaa
Species Country Datab Main constituent Oil yield c Reference

(relative abundance, %) (%)
E. camaldulensis Benin r 1,8-Cineole (3173) 0.61.4 (dry) Moudachirou et al.

(1999)
Burkina Faso r !-Phellandrene (24.8) 1.2 (air-dry) Samat et al. (1998)
Burundi r 1,8-Cineole (43.3) 1.5 (mfb) Dethier et al. (1994)
Egypt r 1,8-Cineole (6575) 0.71.5 Abou-Dahab (1973)
Morocco r 1,8-Cineole (72.4) 0.7 (mfb) Zrira et al. (1992)
Nigeria r 1,8-Cineole () 0.6 (?) Osisiogu (1966)
Zimbabwe r 1,8-Cineole (ca 75) ca 2 (mfb) Doran and Matheson
(1994)
E. cinerea South Africa r 1,8-Cineole (62.7) 1.3 Ndou (1986)
Zimbabwe c 1,8-Cineole (62.5) Coppen unpubl.
E. citriodora Benin r Citronellal 1.5, 2.25.9 Sohounhloue et al.
(65.5, 5590) (air-dry, dry) (1996),
Moudachirou et al.
(1999)
Burundi r Citronellal (46.9) 3.4 (mfb) Dethier et al. (1994)
Egypt r Citronellal (60.5) 0.71.0 Elkiey et al. (1964)
Ghana r Citronellal (60.4) 2.6 (dry) Talalaj (1966)
Kenya r Citronellal (3088) 2.28.3 (mfb) Mwangi et al. (1981)
Madagascar r Citronellal (71.2) De Medici et al.
(1992)
Morocco r Citronellal (56.3) 1.1 (mfb) Zrira et al. (1992)
Nigeria r Citronellal 4.8 (?), 4.8 Osisiogu (1966),
(, 5070) Weiss (1997)
Rwanda r 1,8-Cineole (55.4) 0.6 Chalchat et al. (1997)
Zaire, former c Citronellal (4650) 0.50.8 Weiss (1997)
E. dives Rwanda r Piperitone 3.5, 3.2 (mfb) Chalchat et al. (1997),
(32.8, 52.2) Molangui et al. (1997)
South Africa c Piperitone (3041) Coppen unpubl.
Zaire, former c Piperitone (4555) 3 Weiss (1997)
Zimbabwe r 1,8-Cineole (67.4) 9.9 (mfb) Coppen unpubl.
E. elata South Africa c Piperitone (35.2) Coppen unpubl.
E. globulus Burundi r 1,8-Cineole (63.8) 3.5 (mfb) Dethier et al. (1994)
subsp. Egypt r 1,8-Cineole (7180) 0.91.2 Yousef et al. (1991)
globulus Madagascar r 1,8-Cineole (40.4) De Medici et al.
(1992)
Morocco r 1,8-Cineole 2.1, 1.92.7 Zrira et al. (1992),
(72.8, 6282) (mfb) Zrira and Benjilali
(1996)
South Africa r 1,8-Cineole (48.7) 1.1 Ndou (1986)
E. globulus Burundi r 1,8-Cineole (60.0) 4.8 (mfb) Dethier et al. (1994)
subsp. Morocco r 1,8-Cineole (76.8, 1.4, 2.43.9 Zrira et al. (1992),
maidenii 6980) (mfb) Zrira and Benjilali
(1996)

Table 9.1 (Continued )

Nigeria r 1,8-Cineole () 3.4 (?) Osisiogu (1966)

South Africa r 1,8-Cineole (59.6) 1.1 Ndou (1986)
E. macarthurii Angola r Geranyl acetate 0.21.0 Cardoso and Proena
(64.3) (1968)
Rwanda r Geranyl acetate 0.1 Chalchat et al. (1997)
(50.5)
Zambia r Geranyl acetate 3.2 (air-dry) Chisowa (1997)
(58.0)
E. radiata South Africa r 1,8-Cineole (70.0) >8 Donald (1980)
Swaziland r 1,8-Cineole (5575) 2.54.0 Jacovelli unpubl.
Tanzania r 1,8-Cineole (4056) 8.310.5 Coppen unpubl.
(mfb)
E. sideroxylon South Africa r, c 1,8-Cineole 0.7, Ndou (1986),
(51.8, 75) Weiss (1997)
E. smithii Rwanda r 1,8-Cineole (84.3) 2.5 Chalchat et al.
(1997)
South Africa c 1,8-Cineole (71.1) Coppen unpubl.
Swaziland c, r 1,8-Cineole , 5.88.4 Jacovelli unpubl.,
(6575, 6271) (mfb) Coppen unpubl.
Tanzania r 1,8-Cineole (6470) 5.06.8 (mfb) Coppen unpubl.
Zaire, former c 1,8-Cineole () 1.01.5 Weiss (1997)
Zimbabwe c, r 1,8-Cineole , 5.0 (mfb) Coppen unpubl.
(70.0, 70.7)
E. staigeriana Zaire, former c Citral () ca 4 Weiss (1997)
Zimbabwe r Citral (27.9) 5.9 (mfb) Coppen unpubl.
a The species listed are those where there has been at some time, or is, commercial production of oil somewhere in Africa or
where, in the case of E. camaldulensis, there is the potential for it. Some of the references cited refer to other species, in addi-
tion to those indicated here.
b Indicates whether data are research results (r) or relate to commercial production (c).
c Yields are on a fresh weight basis unless otherwise indicated; mfb #moisture free basis. Yields given by Coppen (unpubl.)
refer to distillation of leaves only, that is, no twigs or woody material.
particularly biomass production and frost tolerance. Provenance trials in Swaziland found the
best overall performers came from Tallaganda State Forest and Narooma (both New South
Wales, Australia), whilst South African trials found Wombeyan Road, Larrys Mountain and
Mount Dromedary the best provenances on the basis of performance and frost tolerance.
E. smithii requires deep soils and a mean annual temperature of "15C. In Southern Africa, the
species appears to be very susceptible to diseases, notably pathogenic fungi causing root rot and
stem cankers. Although E. smithii can produce reasonably straight stems, the wood splits badly
and it can have spiral grain (ICFR 1997, Jacovelli 2002).

E. radiata and E. dives
E. radiata and E. dives exhibit significant intraspecific variation, particularly with regard to their
oil characteristics. Both species have populations rich in phellandrene or piperitone as well as
cineole. Parent trees must be tested first for their oil content and composition before collecting
seed of either species for the establishment of oil plantations in order to check that the desired
chemotype has been selected. Certain provenances and individual trees of E. radiata have shown
very high yields of cineole-rich oil in trials in Swaziland: the Nerrigundah region of New South
Wales appears very promising. The cineole form of E. dives is still harvested in New South Wales
(around Tumut, Batlow, Tumbarumba and Rosewood) although most seed imported into Africa
has proved to be the piperitone-rich variety (Boland et al. 1991, Jacovelli 2002). Oil produced in
South Africa is all from the piperitone/phellandrene form of E. dives. Both species are small trees
with generally poor form (E. radiata is often multi-stemmed) and hence they are not good
multipurpose trees.
E. globulus and its subspecies

E. globulus possesses many desirable traits and these led to its widespread planting in Africa: it is
easy to establish (being unpalatable to grazing animals) and is a fast grower, it has good stem
form, good fuelwood and pulping properties, and its widespread rooting system controls ero-
sion. However, the species susceptibility to a range of pests and diseases has limited its planting
in Africa. Although E. globulus is the main source of cineole-rich oil outside Africa, its oil yield
is generally lower than that of many other species cultivated in Africa (Table 9.1). Boland et al.
(1991), however, report some individuals with up to 4 per cent oil, with an average cineole con-
tent of 6575 per cent. Two subspecies of E. globulus, maidenii and bicostata, appear promising
species for certain parts of Africa the former in warmer and drier situations than suits E. globu-
lus and the latter in cooler conditions than E. globulus. E. globulus subsp. bicostata has individuals
with higher oil yields than E. globulus (Eldridge et al. 1993). All species, however, appear sus-
ceptible to the eucalyptus snout beetle and in trials in Swaziland E. globulus subsp. bicostata was
very attractive to a number of pests (see below and Jacovelli 2002).
Other cineole-rich species

E. camaldulensis is a very adaptable and drought-tolerant species. It has performed well in many
of the drier regions of Africa, although on better sites, particularly areas with deeper soils and
higher rainfall, its growth falls well behind many other eucalypts. It also produces an excellent
fuelwood. The identification of cineole-rich genotypes, particularly from the tropical prove-
nances such as Petford, could lead to this species being used for cineole production in drier
regions of Africa (Doran and Brophy 1990).
E. cinerea is a promising species for oil production in cooler and moist parts of Africa, and
has been used for commercial oil production, albeit on a very limited scale, in Zimbabwe
(Figure 9.1). It is a very frost-hardy species and tolerates poor soils (Ndou and von Wandruszka
1986). Weiss (1997) notes that oil from E. sideroxylon was once produced commercially in South
Africa, where it was used as a flotation agent in the mining industry. E. badjensis is another cine-
ole-rich species recently introduced to Africa, where it has performed well in species-provenance
trials in South Africa. It has proved to be very frost-tolerant but has also been heavily attacked
by the ubiquitous snout beetle (ICFR 1997).

Figure 9.1 Eucalyptus cinerea being harvested for oil production in Zimbabwe (photo: J. Coppen).
The mallee eucalypt species tried to date in Africa, particularly E. polybractea, grow very
slowly. Even though the cineole content of the oil from this and other mallee species is often very
high (up to 90 per cent), the overall biomass production, and thus oil yield, is very poor
compared to many of the other cineole-rich species cultivated in Africa (Donald 1980).
Industrial and perfumery oil species

The use of E. dives as a source of industrial (piperitone-rich) oil has been referred to above. E. elata
is grown commercially in South Africa for its timber and it tolerates poor sites and is frost hardy.
Some E. elata individuals have a very high leaf oil content (usually high in piperitone and/or
phellandrene) but the species is said to be very variable. Considerable screening would be needed
before the species could be considered for commercial oil production (V. Davidson pers. comm.).
Poor market prices for the flavouring and perfumery eucalyptus oils have restricted the plant-
ing in Africa of E. citriodora, E. macarthurii and E. staigeriana specifically for oil production.
E. citriodora, however, is cultivated in many African countries and has been grown commercially
in Africa for its citronellal-rich oil (Table 9.1). The species is fairly widely planted as an orna-
mental in Southern Africa, where its fragrant, lemon-scented foliage is also used locally as an
insect repellent. E. citriodora prefers warmer, humid areas, where it produces a hard, durable tim-
ber. There has been only limited and occasional commercial production in Central and Southern
Africa of oils from E. macarthurii (rich in geranyl acetate) and E. staigeriana (rich in monoter-
penes, especially neral, geranial, methyl geranate and geranyl acetate; Boland et al. 1991) and
there is currently little demand for the oil of either species (Robbins 1983, Weiss 1997).
E. macarthurii is planted on a large scale (for timber production) in the South African highveld
on poor soils and in frost-prone areas.

Silviculture
Basic information
The site requirements and silvicultural characteristics of the principal oil-bearing eucalypts
introduced into Africa are detailed in Table 9.2 (summarised from information contained in
Poynton 1979, FAO 1981, Florence 1996, ICFR 1997, Jacovelli 2002).
Seedling production
In many African countries, small-scale, low-tech nurseries are often appropriate, particularly in
remote regions with a poorly developed infrastructure. The shift towards decentralised nursery
systems in many developing countries has ensured more effective seedling distribution and
greater participation by local people (Shanks and Carter 1994). On the other hand, large, cen-
tralised, nurseries have proved successful in some other African countries. These modern nurseries
often use either expanded polystyrene (Styrofoam) or plastic (Unigro) trays and raise seedlings
in a growing medium of composted pine bark or vermiculite (Donald 1986, Jacovelli 1994).
Whichever nursery system is chosen to produce seedlings for a eucalyptus oil operation, two fac-
tors are crucial to success: the need for plantings to be reasonably concentrated around a central
distillation plant (since it is important to minimise the transport cost of the bulky leaf material)
and the importance of using the seed from parent trees with the desired oil characteristics.
Three other key points should be borne in mind by potential oil producers:
1 Provenance details must be recorded (and provided by reputable seed merchants) and differ-
ent seedlots should be kept separate in the nursery and in the field.
2 All unhealthy or under-sized seedlings should be discarded; using poor planting stock will
not achieve the objective of establishing uniform, well-stocked plantations.
Table 9.2 Site requirements and silvicultural characteristics of oil-bearing eucalypts cultivated in
Africa
Species Min Frost Drought Stem Wood Pests and Principle

MARa toleranceb toleranceb formc qualityd diseasese type of oil
E. camaldulensis 400 m/s h 2 4 3 Variablef

E. cinerea 700 h m 2 2 3 1,8-Cineole
E. citriodora 600 s h 4 5 4 Citronellal
E. dives 850 h m 2 1 4 Variableg
E. elata 1000 h m 3 3 3 Piperitone
E. globulus 800 s s 4 4 1 1,8-Cineole
E. globulus subsp. 800 s m 4 4 1 1,8-Cineole
maidenii
E. macarthurii 850 h m 3 3 4 Geranyl acetate
E. radiata 850 m m 1 1 4 Variableg
E. sideroxylon 500 m h 2 4 3 1,8-Cineole
E. smithii 850 h m 2 2 2 1,8-Cineole
E. staigeriana 1000 s h 2 4 3 Citral
a Mean annual rainfall (mm).
b Hardy (h), moderately hardy (m) or sensitive (s) to frosts or drought.
c On scale 1 (bushy) to 5 (straight stemmed).
d On scale 1 (poor quality) to 5 (excellent quality).
e On scale 1 (very susceptible) to 5 (rarely affected).
f Only the 1,8-cineole chemotype is likely to be important commercially.
g Numerous chemotypes but in Africa E. dives is mainly piperitone and E. radiata 1,8-cineole.

3 Through careful planning and knowledge of local conditions the sowing must be timed so
that seedlings are ready at the optimum time (for most seasonally dry areas in Africa the
best time to plant is at the start of the main rainy season).
Vegetative propagation
Vegetative propagation enables the mass multiplication of desirable genotypes to be achieved.
Some of the first trials of rooted eucalypt cuttings, on E. camaldulensis, took place in Africa
(Morocco) in the 1950s. Since then, mass production by rooting cuttings has been carried out in
Africa on a commercial scale. From around 1964, French researchers at the Centre Technique
Forestier Tropical at Pointe Noire in the Congo successfully mass-produced eucalypt cuttings
(mainly the hybrid E. tereticornis $ E. grandis). More recently, in South Africa, pure E. grandis,
and many E. grandis hybrid clones, have been successfully produced on a large scale (Eldridge
et al. 1993).
For obvious economic reasons, virtually all the vegetative propagation work to date in Africa
has concentrated on maximising fibre production. There has been some research, however, with
mass propagation of cineole-rich species in Southern Africa. Working with E. radiata, Donald
(1980) had success rooting cuttings using standard techniques developed for eucalypts (as
described by Eldridge et al. 1993). However, he reported marked clonal variation in rooting abil-
ity. In South Africa, E. smithii is classed as a difficult rooting species, along with a number of
other hard-gums (cold-tolerant eucalypts).
In Swaziland, in the late 1980s, attempts were made to root cuttings from young coppice
shoots of selected high cineole-yielding E. smithii and E. radiata coppiced trees from plantations.
The Oxford Forestry Institute (OFI) successfully propagated shoot-tip cuttings from both
species. OFI also raised seedlings from commercial seed of E. smithii and E. radiata and
attempted micropropagation from these. Up to 67 per cent of E. smithii and 50 per cent of
E. radiata clones rooted successfully, although there was a marked clonal variation in rooting
ability. These results at least indicate that micropropagation for the rapid multiplication of
selected oil-producing eucalypts is possible (Woodward and Thomson 1989).
Cultivation methods for establishing oil crops

The topics described below summarise the practices developed mainly in Southern Africa for the
establishment of large-scale eucalypt plantations. Much of the work has been carried out with
the most important timber species, E. grandis, but research has shown that the same principles
generally apply to all eucalypt species. What may alter in plantings made specifically for oil
production are the spacing, fertiliser regime and rotation.
Establishment costs will vary significantly depending on the local situation. Table 9.3
presents typical inputs involved in establishing eucalyptus oil plantations in Southern Africa
where there are significant mechanical inputs. In some African countries it may be more cost-
effective (and possibly more socially or environmentally acceptable) to use more labour, particu-
larly for land clearance and planting preparation. The costs will vary considerably depending on
site conditions.
Land preparation
Thorough land preparation for the successful establishment of eucalypt plantations has long
been recommended in Southern Africa. Where there is a rooting impediment including soils

Table 9.3 Typical inputs involved in establishing eucalyptus oil plantations in Southern Africa
Job description Details Man-days Machine-hrs Consumables

(per ha) (per ha)
Land preparation
Clearinga 0.5 4.0
Deep rippingb To min. 600 mm 0.5 2.5
Cultivation 0.2 1.5
Pre-plant sprayc 2.0 1.5 Herbicide
Planting/establishment
Plantingd 6.0 Seedlings
Infilling/blankinge 2.0 Seedlings
Fertilising See Table 9.4 3.5 Fertiliser
Weeding, year 1 Manual (line) 45.0
(3 passes) Chemical 6.0 Herbicide
Weeding, year 2 Mechanical 0.5 1.5
(disc, inter-row)
a Varies according to site conditions.

b Necessary on sites with a rooting impediment, including a high clay content.
c Types and dosages depend on current and expected status of weeds.
d Stocking depends on species and objectives.
e Replacement of failures; depends very much on conditions at, and soon after, planting.
with a high clay content contoured deep ripping is beneficial, not only to increase the effective
rooting depth but also to improve the water-holding capacity of the site. On other sites, plough-
ing and cultivation along the planting line is recommended. The manual preparation of pits
is often unsatisfactory for the establishment of eucalypts and is also becoming prohibitively
expensive (Schnau 1984).
Plant espacement
Most eucalyptus oil plantations in Southern Africa were established initially at a spacing of
9%$ 9% (2.74 m $ 2.74 m), equivalent to 1332 stems ha&1. In more recent years there has been
a tendency to increase the stocking density, with one grower in Swaziland planting at
3.0 m $ 1.5 m (2222 stems ha&1). The higher stocking is aimed at increasing the biomass pro-
duction with short-rotation crops, whilst the rectangular spacing allows mechanical access
between the rows for weed control. Foresters have traditionally manipulated stocking to max-
imise the yield of a particular species on a specific site. The objective with eucalypt plantations
established specifically for oil must be to maximise leaf biomass rather than woody material.
One possible way of increasing the biomass production might be to establish high density plan-
tations (even greater than 10,000 stems ha&1), though more research is needed to assess the sus-
tainability of such high levels of stocking by testing various species on different sites.
Weed control
Virtually all eucalypts in cultivation have proved to be intolerant of competition from weeds,
particularly grasses, during their establishment. For optimum growth, it is advisable to keep
eucalypt plantations completely weed-free until canopy closure. As labour costs escalate in many
developing countries, herbicides are increasingly proving cost-effective. The use of grass

pre-emergent herbicides (e.g. active ingredient acetochlor) in combination with a non-specific
herbicide (especially glyphosate), has proved very cost-effective in Southern African countries,
giving up to ten weeks weed control (N.B. advice must always be taken regarding compatibility
and labels must always be read for dosages and safety aspects prior to using herbicides).
Fertilising
Application of fertiliser at planting has proved to be highly cost-effective for eucalypts in
Southern Africa. The full benefit of fertilising, however, is only realised in conjunction with
other silvicultural practices, particularly good weed control, the use of healthy planting stock
and good site preparation (Schnau 1983, 1984). Table 9.4 gives the fertiliser prescriptions for
Southern African conditions (ICFR 1997); under more tropical conditions, boron can also be
important. In the intensive eucalyptus oil operations in Southern Africa these prescriptions have
generally been followed at planting. No additional fertiliser has been added even though the
plantations would be repeatedly harvested on coppice cycles every 1224 months, sometimes for
over twenty years.
An intensive oil operation removes all the leaf and much of the small branch material, and
there is clearly a large nutrient demand on the site over successive rotations. The lack of accurate
yield data from commercial operations, combined with the many factors that can affect oil
yields, makes it difficult to determine whether there has been a decline in oil yield from the
intensively managed African plantations as a result of decreasing soil fertility. Studies have
shown that whilst eucalypts are very efficient users of available nutrients, the chances of them
depleting soil nutrients are increased with shortened rotations and situations where most of the
biomass is removed from the site. Grove et al. (1996) found that the foliage of eucalypts contains
around 20 per cent N and 17 per cent P of the above-ground nutrients. Very short rotations also
expose the site to possible losses through erosion and leaching. The nutrient balance and sus-
tainability of eucalyptus oil production under African conditions clearly needs further research
(Herbert 1996).
Whilst the addition of fertilisers at establishment is clearly beneficial for most eucalypts
growth (particularly on marginal sites), the effect on overall oil yield and oil composition is not
clearly understood. An increase in leaf production does not necessarily produce more oil per unit
Table 9.4 Fertiliser prescriptions for eucalypts in summer rainfall regions of Southern Africa
Topsoil organic carbon N and/or P Standard fertiliser

(%) (per tree) (per tree)
Fully cultivated, virgin sites

"8 15 g P 140 g single superphosphate (10.5% P)
38 5 g N '12 g P 100 g ammoniated superphosphate or
60 g mono-ammonium phosphate
13 8 g N '10 g P 100 g single superphosphate '
25 g limestone ammonium nitrate
or 50 g di-ammonium phosphate
Ripping/pitting
(re-establishment)
"3 8 g N '12 g P 60 g di-ammonium phosphate or
125 g NPK (2 : 3 : 2, 22%)
(3 14 g N '10 g P 100 g NPK (3 : 2 : 0, 25%) or 125 g NPK
(3 : 2 : 1, 25%)

area of land. The limited amount of research on this subject indicates that with E. smithii in
Southern Africa, nitrogen may have a beneficial effect on oil yield (Jacovelli and Coppen 1994).
However, recommended dosages and the economics of fertiliser application to oil plantations
have not been calculated. A positive response has been obtained to fertiliser applied to E. grandis
coppice crops in South Africa but the amounts needed have been so large that the operation is
considered uneconomic (Schnau 1983). For oil plantations managed intensively on a short-
rotation coppice regime, it is likely that nutrients will have to be returned to the system to
sustain yields in the long term.
Rotation
The optimum rotation for oil production depends on many factors, including:
1 The objective(s) (i.e. whether solely oil production, oil and fuelwood, oil and poles, etc.).
2 The site conditions (particularly the climate and nutrient status).
3 The species or provenance origin of the eucalypt(s).
4 The silvicultural regime (e.g. spacing, weed control, fertilisation, etc.).
5 Utilisation/market factors.
Research in Swaziland has shown that the rotation for the first (seedling) crop of E. smithii
should be longer (2030 months, depending on the growth rates) than the subsequent coppice
cycle. This presumably gives the root system time to develop well and makes it better able to
support repeated coppicing later on. In Swaziland, the E. smithii coppice was cut on a cycle of
1218 months, depending on the growth rates. This cycle was based on the time taken for the
crop to reach canopy closure, at which stage the lower leaves begin to be shaded out (and even-
tually die). How many times a crop can be cut depends on stocking levels, the coppicing ability
of the species and the nutrient status of the site. Five-month-old coppiced E. smithii on its eighth
cycle is shown in Figure 9.2. E. smithii plantations in Southern Africa have been repeatedly
harvested for oil for over twenty years with little apparent loss of stool vigour. The main cause of
yield loss is generally from stool death and the resulting reduction in stocking. As a general rule,
plantations with less than 75 per cent stocking should be replanted. The main oil species in
Africa are all classed as good coppicing species.
In Swaziland, the stems of E. smithii were typically cut about 15 cm above the ground. In
South Africa, the practice of one producer of E. dives (piperitone variant) has been to cut the stem
at knee height (45 years after planting, with harvest of the coppice re-growth at 1518 month
intervals thereafter), Figure 9.3.
Irrigation
Studies have shown that climatic factors, and particularly rainfall, have a significant effect on
oil yield. In South Africa, Donald (1980) predicted yields of over 650 kg ha&1 yr&1 by drip
irrigating selected high oil-yielding clones of E. radiata. However, on a continent where water is
frequently scarce, irrigated oil plantations are unlikely to be economically feasible or socially
acceptable.
Pests and diseases

An enormous number of pests and diseases have been identified on eucalypt crops since their
introduction to Africa (FAO 1981). Only those that can cause serious losses to the principal
oil-producing eucalypts in Africa are discussed here.

Figure 9.2 Five-month-old coppiced Eucalyptus smithii on its eighth cycle, Swaziland (photo: J. Coppen).
Figure 9.3 Recently harvested Eucalyptus dives, showing coppice re-growth from the stump, South
Africa (photo: J. Coppen).

The incidence and threat of the many potential pests and diseases can be significantly reduced
by practising sound silvicultural techniques so as to reduce the stress on the crop. These tech-
niques have been described elsewhere in this chapter but the most important are:
1 Careful site-species matching, especially in drought and/or frost-prone areas.
2 Ensuring a broad genetic base is maintained by not planting large, contiguous blocks with
the same species, provenance or clone.
3 Site amelioration to reduce stress (see section on Silviculture).
4 Planting only healthy, vigorous seedlings at the optimum time.
5 Thorough weed control.
Insect pests
Termites
Termites, especially in the semi-arid and sub-humid tropics, cause significant yield losses and
are often a major constraint on forestry development in these regions. The most serious losses are
due to various Macrotermitinae (Termitidae) and exotic trees are most at risk (Cowie et al. 1989).
In higher elevation, cooler areas of Swaziland and South Africa, where most of the eucalyptus oil
plantations are in Africa, termites do not pose a serious threat. Where plantations are established
in drier areas, however, control measures have to be taken. In Zimbabwe, mortalities due to ter-
mites in Eucalyptus are commonly 3050 per cent but can approach 100 per cent in the absence
of any control (Mitchell 1989). The first visible symptoms of termite attack are normally a die
back from the branch tips, followed by rapid death of the whole tree. On inspection, the root
collar (often from just below the ground) will be ring-barked and many of the roots severed. For
many years the organochlorine insecticides (e.g. dieldrin, chlordane and aldrin) were used to
protect trees from termites, but their persistence in the environment means that they are not
now recommended, even in countries where they are still available. Carbosulfan controlled-
release granules (trade name Marshall/suSCon; recommended at 1.0 g active ingredient
per tree at planting) have been successful in a number of sub-Saharan African countries
(Atkinson et al. 1991, Canty 1991). Logan et al. (1990) discuss other, non-chemical control
methods.
Cutworms and white grubs

Cutworms (Lepidoptera: Noctuidae) and white grubs (Coleoptera: Scarabaeidae) have caused sig-
nificant deaths in new plantings of many eucalypts in Southern Africa (including E. smithii).
Both pests cause damage in the first twelve months after planting and can seriously reduce the
stocking of new plantings. Cutworms ring-bark young seedlings at, or just above, ground level
whereas white grubs feed on the fine, lateral roots of seedlings. Control can be achieved by spray-
ing deltamethrin (5 per cent suspension concentrate) at a dose of 0.025 g active ingredient per
tree (Govender 1993).
Eucalyptus snout beetle

The eucalyptus snout beetle (Gonipterus scutellatus) is a major pest which influences the choice of
which Eucalyptus species to plant in many parts of Africa. This defoliating weevil was an unwel-
come visitor from Australia around 1916 and, like many pests when away from their natural

predators, their population exploded on finding large plantations of susceptible hosts. Most
eucalypts growing in Africa were subsequently attacked, with E. globulus and E. globulus subsp.
maidenii proving very susceptible. In Southern Africa, the beetle has also heavily attacked
E. smithii, E. badjensis and E. camaldulensis. Both the adult and the larvae feed on the leaves and
young shoots of susceptible species; severe attacks lead to crown dieback. The severity of attacks
by the snout beetle reached epidemic proportions in Africa in the 1920s and lead to the intro-
duction of a parasitic wasp from Australia. This proved to be very successful in controlling the
pest except at high elevations or latitudes (Poynton 1979).
Other insect pests

There are several sap-sucking insects, particularly scales and psyllids, which affect eucalypts to
varying degrees. Eucalypt plantations in Malawi, Angola and South Africa have been infested by
scale insects. Trial plantings of E. globulus subsp. bicostata in Swaziland have been heavily infested
with a psyllid (unidentified species). Successful control of some species has been achieved by bio-
logical means (FAO 1981). Wood-boring, bark beetles (the most important being Phoracantha
semipunctata Fabr.) have caused serious damage to many eucalypt plantations in Africa. Amongst
the susceptible species are E. globulus and E. camaldulensis. Attacks are more severe where trees
are under drought stress.
Diseases
Damping-off and root rot disease

Root rot is caused by pathogenic fungi, primarily Phytophthora, Pythium and Fusarium spp.,
which occur naturally in the soil (some also occur in water sources). They are responsible for seri-
ous nursery losses through damping-off and they can also cause significant deaths in young
eucalypt plantations. E. smithii has proved susceptible in Southern Africa with up to 30 per cent
deaths being reported, mostly in the first year after planting. In the nursery, widespread seedling
death can occur, with dead patches visible on the stems. Control is mainly by preventative means
for example, by not over-watering, avoiding sowing during very hot periods, treating irrigation
water and by using fungicide drenches (such as benomyl and captan). In the field, there is a
general wilting of the leaves followed by chlorosis (yellowing) and death of the tree. To reduce
root rot losses, cultural practices should be adopted to reduce seedling stress and, ultimately,
susceptible species and/or provenances should be avoided (Viljoen et al. 1992).
Botrytis cinerea
This parasitic fungus is welcomed by some producers of sweet wines (being responsible for
noble rot), but Botrytis cinerea Pers. has caused severe losses in eucalypt nurseries in Africa, as
well as during the first year of establishment. Typical signs are a fine web of greyish mould
(mycelium) which can be seen on infected plant parts. Control is largely by good nursery man-
agement and particularly hygiene: physical damage to seedlings should be minimised (infection
is often via wounds), dead plant material should not be left around and humidity should be kept
as low as possible (e.g. by ensuring good ventilation and not over-watering). Various fungicides
are available to reduce the spread of any outbreaks (e.g. iprodione and benomyl) but chemical
resistance has been reported (Nichol 1992).

Other diseases
Mycosphaerella muelleriana (Thm) Lindau is regarded as a serious leaf pathogen in Southern
Africa, causing leaf-spot disease. The fungus has been identified on many eucalypt species and
although it rarely causes seedling deaths, a heavy infestation undoubtedly will cause growth
losses (Crous and Wingfield 1991). A heavy Mycosphaerella infestation occurred on trial planti-
ngs of E. globulus subsp. bicostata in Swaziland, whilst adjacent plots of E. smithii, E. radiata and
E. dives were unaffected.
Various other fungal pathogens causing stem cankers have caused serious losses in eucalypt
plantations in many countries and are increasingly appearing in Africa. The main culprits in
Southern Africa have been Cryphonectria cubensis (Bruner) Hodges in hot, humid areas and
Endothia gyrosa in cooler regions (Swart and Wingfield 1991, Nichol 1992). Areas of dead bark
(cankers) can be seen on the stems of infected trees, often stained dark reddish-brown from resin
or kino. The only control at present is preventative, by minimising the stress in plantations.
Endothia gyrosa, in particular, is more severe in drought-stressed trees. Little is known
yet concerning oil species resistance to stem cankers but E. smithii oil plantations in Swaziland
have been affected by up to 10 per cent of stem cankers (probably Endothia gyrosa) ( Jacovelli
2002).
Harvesting and oil distillation techniques
Harvesting and transport

In contrast to the mechanised eucalyptus oil operations in Australia, the African oil operations
have always been very labour intensive. Information provided below relates to a typical oil oper-
ation in Swaziland that, until 1994, was producing about 60 t yr&1 of cineole-rich oil from
around 550 ha of E. smithii. The plantations were worked on a short-rotation coppice system to
maximise the leaf biomass produced.
Harvesting and transport are important elements in the operation of an oil business because
the crop is very bulky. Although the first (seedling) crop is cut by chainsaw (due to the large
stem size), the subsequent coppice cuts are made with a hatchet. The harvesting teams comprise
one cutter, three de-branchers and two bundlers, with each team producing approximately three
tonnes of leaf per day. The de-branchers follow, cutting the branches from the main stem and
then collecting the leaf and small branch material into manageable bundles (Figure 9.4). The
bundles are laid in rows every fifth tree line, allowing field extraction by tractor-trailer units.
The transport teams, comprising a tractor driver and four loaders, then load the bundles with
pitchforks onto customised trailers. Four-wheel drive tractors are necessary in order to be able to
transport on wet days. The trailers have a flat-deck, low-bed construction with high side-rails to
support the bulky material and a capacity of approximately 3 t. The leaf is then off-loaded by
hand at the distillation plant. Some of the stem-wood left infield is crosscut (by chainsaw) after
36 weeks drying and taken to the distillation plant to fuel the boiler.
Many variations on the above are possible and local conditions and preferences will ultimately
determine the optimum harvesting and transport methods used. However, for a successful
eucalyptus oil venture the following important factors must be considered:
1 The plantation layout it should enable easy access to pick up the leaf (and minimise dam-
age to the coppice stools).
2 Infrastructure road access is needed so that the leaf can be brought out of the plantation
quickly.

Figure 9.4 Harvested seedling trees of Eucalyptus smithii (twenty-four months) having their branches
trimmed for collection of foliage, Swaziland (photo: J. Coppen).
3 Location the plantations should be reasonably close to the distillation plant to minimise
transport costs.
4 Transport appropriate vehicles are needed to transport bulky leaf material (e.g.
high-sided trailer units).
5 The use of bow-saws or chainsaws for felling.
6 The possibility of extracting whole stems and debranching at the mill.
7 By-products is there a local market for small poles and/or fuelwood?
8 Compaction problems on sensitive sites caused by vehicles going in-field.
Mechanical harvesting has not been considered appropriate or cost-effective under African
conditions to date. The principal oil crops in Africa (E. smithii, E. radiata and E. dives) are not as
suited to mechanical harvesting as tough, mallee species such as E. polybractea.
Distillation
Capital investment in distillation equipment does not have to be great low-cost stills and
ancillary equipment are often adequate (see Chapter 6) and are used in small-scale eucalyptus oil
operations in many countries. However, that is not to say that the means by which distillation is
achieved should be taken lightly and it is shortsighted, particularly for large-scale operations
where a significant investment has been made with plantation establishment, to pay scant atten-
tion to it. As much good quality oil as possible should be extracted from the leaf in as efficient
and cost-effective a manner as possible. Thus, for example, boilers are best installed to produce
steam rather than relying on direct firing of water below the charge of leaf. Part of the distillery

in which E. smithii leaf is being packed into stills at the (then) Shiselweni Forestry Co. eucalyp-
tus oil operation in Swaziland is shown in Figure 9.5.
The reduced prices being obtained for cineole-rich oil from Africa in the late 1980s high-
lighted the need for operators to increase the efficiency of their operations. The following factors
were found to be important in Swaziland:
1 Fuelwood (for the boiler) is a significant cost of the operation, particularly where there is an
alternative market for the wood (e.g. for poles or pulp).
2 Fuelwood should always be air-dried to increase its heating efficiency (preferably for a min-
imum of six months).
3 Spent leaf can be used to reduce the fuelwood requirement, although this requires cutting
and a continuous feed mechanism (a Dutch oven).
4 Tight, uniform packing of the leaf in the stills has proved to be very important so that the
steam is forced through, not around, the leaf material.
5 The stills must be well sealed to minimise the loss of oil vapour.
6 It is vital to ensure that safety valves are fitted and functioning to relieve any build-up of
pressure in tightly packed stills.
7 The distillation must be closely monitored to ensure that maximum yields of oil are
obtained from the charge.
8 An efficient condenser will reduce the amount of water required to cool the distillate (oil
vapour and steam) emerging from the still.
Oil operations typically work two shifts per day at the distillery and so it is vital to ensure
that there is sufficient leaf brought in to maintain production. Typical charge sizes are 23t of
fresh leaf. The distillation takes place under low pressure, around 345 kPa, and usually takes
Figure 9.5 Eucalyptus smithii leaf being packed into stills for distillation, Swaziland (photo:
J. Coppen).

around 2 h (longer during cool periods). In some operations the spent leaf is returned to the field
and used as a mulch; this is a difficult (and costly) operation, as the material has to be chopped
and then transported back to the field, but it does have benefits for the site in terms of reducing
soil erosion and the need for weed control.
Most African eucalyptus oil is exported in its crude form (typically around 7075 per cent
cineole in Southern African operations) for re-distillation. Rectification is necessary to remove
impurities and increase the cineole content of the oil to meet industry standards. The price dif-
ferential between the crude oil as it emerges from the still and rectified oil, including high
purity oil "98 per cent cineole (eucalyptol), will determine whether investment in a rectifica-
tion plant is justified. At the levels of production of most African growers, and the price of oil in
the late 1980s and early 1990s, such an investment could not be justified.
Oil yields
Table 9.1 lists oil yields obtained in Africa, mainly from research data there is a paucity of
information on yields from commercial operations and published research results are often
derived from a very limited number of leaf samples. Moudachirou et al. (1999) have demon-
strated significant seasonal and site effects, particularly the latter in the case of E. citriodora grow-
ing in Benin. However, detailed records from the operation in Swaziland, together with research
results from elsewhere on the continent, provide a reasonable picture of actual (and achievable)
oil yields.
Commercial eucalyptus oil production in Africa has taken place mainly from rain-fed, short-
rotation coppice crops. Oil yields range from around 50 kg to over 500 kg of oil ha&1 yr&1. The
lower yields are obtained from poor sites in areas marginal for the particular oil species planted.
Conversely, the very high yields have been obtained from high potential sites (e.g. deep, fertile
soils and high rainfall) where high stocking levels and very short rotations are possible. In the
tropical conditions of the former Zaire, for example, two E. smithii crops a year were being
harvested, producing up to 600 kg of oil ha&1 yr&1 (Weiss 1997). From 1979 to 1985, E. smithii
plantations in Swaziland produced an average of 120 kg of oil ha&1 yr&1. This is from a region
with marginal rainfall (mean annual 845 mm) and an often prolonged dry season. These
yields compare favourably with those obtained from natural stands of E. polybractea in Australia,
where around 30150 kg of oil per hectare may be produced from an 18-month harvest
(Chapter 7).
From commercial oil operations in Southern Africa a number of observations regarding yields
have been made, although not all have been proven scientifically:
1 Significant intraspecific variation has been found in E. radiata, E. dives, E. citriodora and
E. globulus subsp. bicostata with regard to both oil yield and oil composition.
2 Maximum oil yields are obtained from short-rotation, coppice crops. Yields are significantly
less from operations where oil production is secondary to the production of other products.
3 Site quality and climate, particularly nutrient status and rainfall, appear to be extremely
important factors affecting oil yields. In general, the higher the site potential, the higher
the oil yields.
4 Higher oil yields have been obtained during the warmer, summer months (many African
producers suspend production during the coldest periods).
5 Higher oil yields per hectare are obtained from coppice crops than from seedling crops (due
primarily to the increased biomass of multi-stemmed coppice).
6 Younger leaves yield more oil than older leaves.

Storage, packing and quality control
Crude eucalyptus oil, like some other essential oils, is corrosive and since most African oil is
exported, good quality, lined steel drums have to be used for storing and transporting it. Clear
labelling to meet national and/or international regulations is also necessary.
Most African-produced cineole-rich eucalyptus oil meets the 70/75 requirement (percentage
of cineole) in its crude form. In one commercial oil operation in Swaziland all batches of oil were
tested for their 1,8-cineole content prior to being exported using the o-cresol crystallisation
method (Appendix 5). E. smithii oil, however, has a poor reputation with some buyers. Robbins
(1983) refers to the low cineole content of some batches (below the industrys minimum require-
ment of 70 per cent cineole) and its acrid odour, due to the presence of aldehydes (although
E. globulus crude oil can also contain the undesirable isovaleraldehyde). Distillation trials with
E. smithii oil in Swaziland showed that its quality could be significantly increased by excluding
the initial 5 per cent of the distillate (which contains primarily isovaleraldehyde) from the
bulked oil intended for export. The higher price that it fetches offsets any loss in overall yield.
Buyers have generally expressed a preference for the cineole-rich oils of E. radiata and E. dives to
that of E. smithii, though this is not always reflected in the prices offered.
Research needs
Despite eucalypts having been cultivated for their essential oils in Africa for over fifty years,
comparatively little scientific research has been carried out aimed at improving oil quality and
yields. Recent work in Southern Africa, however, has at least identified the priority areas for
research, namely:
1 The identification of genotypes with superior oil characteristics, particularly from the prin-
cipal cineole-rich species E. smithii, E. dives and E. radiata. Also of great interest to Africa is
E. camaldulensis, due to its ability to grow in drier regions.
2 Trial plantings of other, lesser-known eucalypts with desirable oil characteristics (see Table 9.1).
3 The mass-multiplication (using rooted cuttings or micropropagation techniques) of these
desirable genotypes to maximise oil yields.
4 With all selection and breeding work, it is most important to maintain a broad genetic base
and to screen for resistance to well-known pests and diseases (particularly root rots and stem
cankers).
5 A greater understanding is needed of the nutrient balance and, especially, the longer-term
effects on various sites of removing much of the above-ground biomass.
6 The cost-effectiveness of various management options needs assessing, particularly fertilis-
ing and spacing regimes, longer rotations and multipurpose plantations.
Future prospects for eucalyptus oil production in Africa

The recent sharp decline in the production of eucalyptus oil from Africa is due to a number of
factors. In the late 1980s and early 1990s, low-priced Chinese oil (mostly from E. globulus)
dominated international trade in eucalyptus oil and lead to prices being depressed. The
competitive advantage of African producers was further eroded around this time by escalating
production costs, particularly for labour in what is a labour-intensive industry. Added to this
were the problems of increased incidence of disease with the main species, E. smithii, and the
variation that was found in the quality of seed available from natural stands of possible alterna-
tive cineole-rich species (particularly E. radiata and E. dives).

With such problems, the eucalyptus oil industry in Africa might not appear to have a promis-
ing future. There are, however, some very positive signs, not least of which are the excellent oil
yields that have been achieved in many parts of Africa with a number of oil-rich eucalypts. More
is being learnt, too, about the suitability of Eucalyptus species for a wide range of sites and objec-
tives. The impressive biomass production of E. smithii, in particular, coupled with the fact
that this species yields a consistent quality, cineole-rich oil, makes it a species of exceptional
potential.
There are also clear indications from research that selection and multiplication of genotypes
with superior oil characteristics could result in very large yield improvements, particularly when
combined with good silvicultural practices. The existence of some genotypes of E. radiata and
E. dives possessing high quantities of cineole-rich oil is very encouraging. Studies with E. kochii
and E. camaldulensis have found very high family heritabilities for cineole yield and this bodes
well for breeding programmes aimed at increasing the sustainable yields of eucalyptus oils
(Barton et al. 1991, Doran and Matheson 1994). Breeding programmes in which the emphasis
has hitherto been on wood quality and productivity are now beginning to look at the volatile
oils and this, too, is encouraging. Thus, selection of individuals for the production of oil from
E. urophylla, E. grandis and E. urophylla $ E. grandis has been reported as part of the CTFT
afforestation programme in the Congo (Menut et al. 1992).
Another positive sign in recent years has been the resurgence in interest (primarily in devel-
oped countries) in natural products eucalyptus oils are in demand for use in a wide range of
therapeutic products and applications, including aromatherapy. With careful planning (and
suitable incentives), eucalyptus oil production could become a very appealing small business
venture for local farmers in Africa. A rural cooperative approach is likely to suit many African
countries but, as Weiss (1997) emphasises, considerable institutional and other support would
be needed. Crucial elements would involve the supply of quality seed (or seedlings), silvicultural
advice, a centralised distillation plant and marketing assistance. Provided the scale of production
could justify the additional investment required, downstream processing, particularly rectifica-
tion, could become attractive to increase the value of the final product.
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eucalypts in South America
Larcio Couto
Introduction
FAO country estimates for the areas of plantation eucalypts in 1990 show that Brazil had the
second largest area after India, 3.6 million ha (Pandey 1995). The most recent estimate, also
from FAO sources, puts the figure at 3.1 million ha (Appendix 2). Although this massive
resource is designed to meet the raw material needs of Brazils forest-based industries such as
timber, pulp and charcoal, it has, nevertheless, indirectly influenced the development of the
eucalyptus oil industry in the country, at least in the early days. Apart from China, Brazil has
been the only other significant producer and exporter of Eucalyptus citriodora oil and this arose
from the widespread availability of waste leaf from E. citriodora planted primarily for charcoal
production. Charcoal is used for fuelling the furnaces in the iron and steel industries and in the
manufacture of cement and E. citriodora has played an important role in the Brazilian economy
(Galanti 1987). In addition to E. citriodora oil, oils from E. globulus and E. staigeriana are
produced in Brazil.
Production of eucalyptus oil elsewhere in South America is small compared to that in Brazil
and although brief mention is made later in this chapter to Chile, Bolivia, Paraguay and some
other countries, the bulk of the discussion concerns methodologies employed in Brazil. Much of
what is described will, of course, be applicable elsewhere. Details are given in the form of a case
study relating to a company which, until recently, produced E. citriodora oil in Minas Gerais
state. Supplementary information is provided from other sources concerning this oil and those
from E. globulus and E. staigeriana produced in Brazil.
Historical review
Introduction of eucalypts to Brazil and end use

Although eucalypts were planted in the Botanical Gardens of Rio de Janeiro as early as 1824, it
was Edmundo Navarro de Andrade who established the first eucalypt plantations in the first
decade of the twentieth century (Couto et al. 2000). On returning to Brazil from his studies of
agronomy in Portugal he brought with him seeds of E. globulus for planting. He worked for a
railroad company to provide firewood for the steam engines and wood for sleepers and the exper-
imental plots were so successful that they led to over 200 species of Eucalyptus being introduced
into Brazil.
From 1909 to 1965, about 470,000 ha of eucalypts were planted, 80 per cent of them in So
Paulo state and intended mainly as a substitute for native woods for use as fuelwood. Other

energy sources such as good quality coal were not available in Brazil. In 1948, the first eucalypt
plantations were established in Minas Gerais to provide wood for charcoal for use by the iron and
steel industries. Although Pinus spp. were also being introduced, partly in response to depletion
of the native Araucaria as a source of high quality timber, the high yields and quicker returns
from short-rotation eucalypts saw them become the dominant plantation species. A federal law
passed in 1966, and a further one in 1970, gave considerable financial incentives to companies to
plant trees, and accelerated this process of reforestation. The consumption of charcoal by the
cement, iron and steel industries has continued to increase although this has been tempered by
lower prices of imported coal since 1997 and other economic factors which are beginning to
make alternative forms of fuel more attractive.
A further impetus to the planting of eucalypts was the increasing use of short fibre pulp for
paper making in the 1970s. The favourable conditions for growth in Brazil, the development of
appropriate silvicultural techniques and the advantages gained by using cloned planting stock
and hybrids led to the massive plantations that now feed Brazils pulp mills. Aracruz Celulose
S.A. alone has 132,000 ha of eucalypt plantations. In the 1980s, coinciding with growing envi-
ronmental concerns worldwide on the loss of natural forests and other related issues, laws were
passed which removed the financial incentives to the forestry sector provided by the earlier leg-
islation. Today, new plantations are mostly established on previously harvested areas rather than
on new land.
Brazils eucalypt plantations extend from the northern states of Par and Maranho to the
eastern and southern states of Bahia, Minas Gerais, Esprito Santo, So Paulo, Paran, Santa
Catarina and Rio Grande do Sul. The species grown for pulp are mainly E. grandis, E. urophylla
(and hybrids of these) and E. saligna, that is, species containing little or no leaf oil, together with
E. dunnii and a few oil-yielding species such as E. globulus, E. viminalis and E. tereticornis.
Although E. citriodora is still the dominant species for charcoal production, there has been some
replacement of it by other, faster growing species of eucalypt.
Eucalyptus oil production in Brazil

Production of essential oils from eucalypts in Brazil started during World War II. It began as a
result of a collapse in international trading of citronellal-rich oil produced in Java from cit-
ronella. At that time there were, in Brazil, some E. citriodora and E. globulus plantations and
these were used by the first local companies to produce essential oils, mainly citronellal-rich oil
from E. citriodora. So Paulo state was the most important area for essential oil production and in
the 1970s Brazil became the biggest producer of E. citriodora oil in the world. Later, Minas
Gerais, Esprito Santo, Mato Grosso do Sul and Bahia contributed to the increase in Brazilian
production of this type of oil (Romani 1972). E. citriodora oil is employed in whole form for
fragrance purposes but is also used as a source of citronellal. This in turn is used either as an
aroma chemical or for conversion to hydroxycitronellal and other compounds used in perfumery.
E. globulus, one of the first species to be introduced in Brazil, is a source of cineole-rich medi-
cinal oil. However, while E. citriodora is widely distributed from the north to the south of the
country, E. globulus is highly dependent on specific climatic and edaphic conditions.
Furthermore, E. globulus in Brazil is used mainly as a source of leaf oil whereas E. citriodora is
grown widely for timber and charcoal production and so forms an abundant, ready-made source
of waste leaf suitable for distillation. Today, the main eucalyptus oil distilleries in Brazil are
located in So Paulo, Minas Gerais, Bahia and Mato Grosso do Sul and use E. citriodora leaf as the
principal, or sole, raw material.

Of the many hundreds of species of Eucalyptus which exist, fewer than twenty have ever been
exploited commercially for oil production (Boland et al. 1991). For a country as large as Brazil,
with continental dimensions and a very large edaphic and climatic diversity, it is perhaps not
surprising that of the half dozen most important species for oil production worldwide, two are
utilised in this way in Brazil, E. citriodora and E. globulus. A third species, E. staigeriana, is also
grown for oil and Brazil is the only such source. E. citriodora and E. globulus furnish oils in
approximately 11.5 per cent yield (fresh weight) containing citronellal (6585 per cent) and
1,8-cineole (around 65 per cent), respectively. E. staigeriana oil, in yields of 1.21.5 per cent,
contains a more complex mixture of terpenes (see later), but with citral as an important fragrance
component.
Today, the production of eucalyptus oil in Brazil is carried out by a small number of medium-
to-large companies, together with some smaller ones. The technology used in the distillation of
the oil is virtually the same for all of them and the main difference is in the way in which they
obtain their raw material. Larger companies have their own eucalypt plantations, established
specifically for oil production, while the smaller ones rely on waste leaf bought from small
landowners or from eucalypt plantations managed for the production of wood (for poles and tim-
ber as well as charcoal and firewood). Both large and small companies sometimes enter into joint
ventures with those involved in E. citriodora-based charcoal production the leaves collected
from harvested areas are sent to the distilleries and a percentage of the profits from the production
of oil is paid back for the use of the raw material.
Oil characteristics
The general characteristics of the oils from the commercially important oil-bearing eucalypts
have been described elsewhere in this volume but data relevant to South America are presented
in Table 10.1 (see also Baez et al. 1992).
E. staigeriana oil, which is used in perfumery in whole form, has, as implied by the variable
but relatively low figures for citral shown in Table 10.1, a complex composition. Analysis of one
such commercial sample found 26.8 per cent limonene, 10.8 per cent terpinolene, 9.6 per cent
neral and 12.5 per cent geranial (i.e. 22.1 per cent citral), 4.7 per cent methyl geranate,
4.6 per cent geranyl acetate and 4.7 per cent geraniol (Coppen unpubl.).
Specifications provided by a leading producer of E. globulus, E. citriodora and E. staigeriana
oils in Brazil are a minimum 70 per cent 1,8-cineole, minimum 70 per cent citronellal and
minimum 20 per cent citral, respectively.
Eucalyptus citriodora: a case study of its cultivation and distillation in Brazil

In some regions of So Paulo state, the lower branches of oil-bearing eucalypts are periodically
cropped for oil production, leaving the stems standing for further growth and future use for tim-
ber. In parts of Minas Gerais and Bahia, the availability of suitable waste leaf from eucalypt
plantations managed for charcoal production is taken advantage of to produce oil when the tree
is felled at the end of the rotation. In both cases eucalyptus oil production is a secondary activity.
There are also companies, however, who grow eucalypts specifically for oil and, here, the trees are
planted and managed more intensively, with much shorter rotations than the normal ones of
around seven years.
The company used as a basis for this case study was founded in 1990 and established itself in
the western part of Minas Gerais, where it acquired 2500 ha of land in the savanna region. Five
million trees of E. citriodora were planted specifically for oil production. The company built a

Table 10.1 Yields and characteristics of leaf oils obtained from eucalypts growing in South Americaa
E. camaldulensis Argentina r p-Cymene (31.2) 0.4 De Iglesias et al. (1977)

Chile r p-Cymene (31.4) 0.2 Erazo et al. (1990)
E. cinerea Argentina r 1,8-Cineole (69.0) 0.7 (air-dry) De Iglesias et al. (1980)
Brazil r, r 1,8-Cineole (76.3, 1.4, 4.18.2 Silva et al. (1978),
61.062.8) (dry) Moreira et al. (1980)
E. citriodora Brazil c Citronellal (75.7) Coppen unpubl.
Chile r Citronellal (85.1) 3.0 Erazo et al. (1990)
Uruguay r Citronellal (59.2) 1.3 Dellacassa et al. (1990)
E. globulus Brazil c 1,8-Cineole (73.6) Coppen unpubl.
subsp. globulus Chile c 1,8-Cineole (6075) 1.21.7 Anon. (1987)
r 1,8-Cineole (60.3) 1.0 Erazo et al. (1990)
Uruguay r 1,8-Cineole (64.5) 0.8 Dellacassa et al. (1990)
E. piperita Brazil r Piperitone (7.5 40.5) 0.22.1 Pinto et al. (1982)
r 1,8-Cineole (47.4) Garrone (1987)
E. staigeriana Brazil c, c Citral (37.2, 22.1) , Porsch et al. (1965),
Coppen unpubl.
Brazil r Citral (10.163.0) 0.32.5 Pinto et al. (1976)
E. viminalis Uruguay r 1,8-Cineole (43.6) 0.4 Dellacassa et al. (1990)
a The species listed are those where there is commercial production of the oil in South America (not necessarily in the
country specified) or where there is, or has been, production elsewhere in the world. Some of the references cited refer
to other species, in addition to those indicated here.
b Indicates whether data are research results (r) or relate to commercial production (c).
c Yields are on a fresh weight basis unless otherwise indicated.
distillery (annual production capacity 360 t oil) and infrastructure such as laboratories, offices
and a village for its 250 employees.
Silviculture
Site selection
E. citriodora does not present good leaf biomass yield in areas subject to strong winds since they
desiccate the leaves and lead to leaf drop. It is very important, therefore, to select sites for its cul-
tivation which are not exposed to winds. The sites should also be located in flat or gently undu-
lating areas to facilitate mechanised silvicultural and harvesting operations. The stands are best
kept below 4050 ha in size and planted with the contours when necessary.
Land preparation
E. citriodora is very demanding on soil quality and does not grow well where the pH is lower
than 5.5 (such as lateritic soils). It is therefore important to analyse soil samples for each plot
before planting and to correct soil acidity where necessary. Nutrients such as phosphorus and
potassium, and micronutrients such as boron and zinc, should also be added if required. With
the annual harvesting of leaf, and the consequent continued removal of plant biomass from the

land, occasional foliar analysis is also desirable in order to monitor and rectify any depletion of
nutrients and micronutrients.
In the area considered in this case study there were sandy soils and the first operation
consisted of locating contour lines in the field to avoid erosion, mainly during the rainy season.
To improve the physical and chemical properties of the soil it was common practice to plant
legumes one year before planting the eucalypts. These plants are then incorporated into the soil
during land preparation. After demarcation of the stands and the building of roads and fire
breaks, 1000 kg of lime and 500 kg of natural phosphate per hectare are applied five months and
one month, respectively, before planting the eucalypt seedlings. This is followed by arrowing
and ploughing the soil to a depth of 30 cm and furrowing to 60 cm. Finally, the soil is levelled
with a lighter arrow and the planting lines in contour are marked with furrows 30 cm
deep. Before arrowing and ploughing, leaf cutting ants are controlled using sulfluramid-based
pesticides.
Establishment
Before planting the seedlings a final check is made on the absence of leaf cutting ants. The
spacing between rows is 2.8 m and the distance between plants in the same row is 0.75 m. A
total of 300 kg of NPK (20 : 20 : 20) plus 6 per cent of boron is applied per hectare, distributed
along the furrows where the planting holes are located. Planting is carried out during the rainy
season as soon as moisture conditions in the soil are satisfactory. At that time, 2g of pesticide are
placed in each planting hole to prevent attack by termites. Replanting of seedlings which
do not survive is carried out fifteen days after the initial planting to avoid heterogeneity in the
size of the trees later on. New applications of fertiliser are made thirty and sixty days after plant-
ing using 50 g of NPK (20 : 0 : 20) per seedling. For each 4050 ha of a new eucalypt plantation
it is necessary to have a labourer to tend the site and to prevent attack of the seedlings by leaf
cutting ants.
In the region applicable to this case study the planting months are generally November and
December, coincident with the rainy season for the western part of Minas Gerais. High temper-
ature and air humidity at this time make it necessary to discontinue harvesting of the leaves,
otherwise fermentation of the raw material is promoted and low quality essential oil is produced.
Advantage is taken of this down time to undertake maintenance of the distillery and to attend
to other necessary work in the eucalypt stands.
Maintenance
The most important silvicultural treatment of eucalypt plantations established for essential oil
production is weeding. In the study in question this involves dealing mainly with grasses such
as Brachiaria brizantha. Initially, control was achieved by applying 4 l/ha of Roundup twice a
year. This resulted in a relatively low tending cost and a good level of soil conservation. Later on,
herbicide application was replaced by renting the forest land to local farmers so that the pastures
could be used by their cattle. Rental was paid on the basis of 10 per cent of the dollar value of
each 15 kg of living animal per month. Besides controlling the grass and other weeds which
might compete with the eucalypts, the cattle provide an additional income for the company.
Two heads of cattle are enough to control the weeds and avoid the use of 8 l of Roundup per year.
The use of cattle to control the weeds, mainly the grasses, was also valuable in reducing the
fire risk.

As mentioned earlier, periodic soil and foliar analyses are carried out for individual stands and
fertilisers applied when necessary, usually at the beginning of the rainy season. Control of leaf
cutting ants is carried out every month of the year.
Rotation
The eucalypt stands are grown under an intensive, coppice system of management, solely for the
purpose of oil production, and harvesting takes place once a year in different months. There are
therefore always stands at different ages and stages of development. There are no special treat-
ments for the coppices or for the stumps but the objective is to obtain the biggest possible pro-
duction of leaf biomass. The trees never reach more than 5 m in height before they are cut and so
irrigation can be used if necessary. The first harvest is usually taken at around 1516 months
(about March) with subsequent harvests at approximately twelve-month intervals. After eleven
or twelve years the original stumps are removed and new seedlings planted.
Silvicultural practice elsewhere in Brazil 1

Propagation is from seed which is germinated over a period of 23 weeks; the seedlings spend a
further three months in the nursery before planting out. Propagation by cuttings has not been
successful. E. globulus is shy to seed in Brazil and most seed for planting purposes is bought from
Australia. Seed of E. citriodora and E. staigeriana is collected from mature trees within the com-
panys plantations.
As in the case study, contour planting is practised in order to avoid soil erosion. Spacing is
3.5 m ! 0.5 m. Fertiliser application is usually too expensive to carry out but spent leaf from
the distillery is returned to the fields to provide some replenishment of nutrients (see later,
Figure 10.4). Undergrowth around the trees is cleared annually.
Harvesting
Initially, the company used to employ manual labour with chain saws to cut the small trees and
to remove the branches with the leaves for transportation to the distillery. No stem biomass was
utilised in any subsequent stage of the processing and the energy required to produce steam was
derived from the residues of distillation. Later, the company adapted a circular saw fitted to a
tractor to mechanise the harvesting operation and so reduce labour costs. The potential hazards
associated with the use of eight chain saws were also thereby eliminated. With this new equip-
ment the trees are cut leaving a stump 0.80.9 m in height. Tests showed that this stump height
gave the best results in terms of percentage of subsequent sprouting. About a third of a hectare
per hour can be harvested. Each year thereafter the cut is made 23 cm above the previous one,
resulting in a loss of only 23 per cent of the coppicing per year.
Loading of the trucks which take the harvested material to the distillery is also mechanised
and approximately 0.6 ha of cut biomass can be loaded per hour. The annual yield of biomass is
around 20 t/ha.
1 Supplementary information provided here and later relates to a company which produces eucalyptus oil from
E. globulus, E. citriodora and E. staigeriana. All three species are grown specifically for oil on a short-rotation, coppice
system of management.

Approximately 30 per cent of the harvesting operation involves manual labour to select the
branches and leaves to go for distillation. The calorific value of this spent material after distilla-
tion when used to fuel subsequent distillations is smaller, and there is less of it, than the
residue from the small whole trees which result from the mechanised part of the harvesting.
These are chipped at the distillery (see below). In both cases, any surplus residue not fed to the
boiler is either sold locally or returned to the fields as organic fertiliser.
Elsewhere in Brazil, the harvesting of coppice-managed eucalypts for oil is sometimes carried
out more frequently than every twelve months. One company clips the side branches a year
after planting and takes the first full harvest at eighteen months. Thereafter, harvesting of
branches and foliage is usually carried out three times in two years. The stems remaining after
recent harvesting of E. citriodora foliage are shown in Figure 10.1. In the fourth year most of the
stems are cut approximately 60 cm from the ground and allowed to sprout; 10 per cent are left
uncut and allowed to grow for timber production. The first harvests from the cut stems are taken
after twelve months, with subsequent ones as before. Some trees have been harvested for thirty
years or more. Most of the harvesting is carried out manually but mechanical grabbers go
between the rows loading the heaped foliage onto tractor-trailers for transport to the distillery
(Figure 10.2).
Figure 10.1 Eucalyptus citriodora being grown specifically for oil, So Paulo state (photo: J. Coppen).

Figure 10.2 Harvested Eucalyptus globulus being loaded for transport back to the distillery (photo:
J. Coppen).
Distillation
Once the trucks containing the harvested biomass arrive back at the distillery each load is
weighed and then fed into a chipper to furnish a mix of chipped eucalypt wood and leaves. The
chipper has the capacity to process 20 t/h of biomass. This biomass is then loaded into the stills
for distillation. Some loss of moisture from the charge before being put into the stills is benefi-
cial since the oil concentration is thereby increased. However, the biomass should not be exposed
to the air for too long since there will be some loss of oil through evaporation and/or enzymic
oxidation or decomposition.
The distillery in this case study has eight stills, each with a nominal capacity of 1.5 t of mixed,
chipped biomass (stem, branches and leaves) and 1.0 t of biomass comprising whole small
branches and leaves. When loading the stills with unchipped material it is essential to pack firmly
and uniformly so as to avoid air gaps and subsequent channelling of steam when distillation is in
progress. This is usually achieved by the workers who load the stills stepping inside them and
stamping the biomass down; at the same time a little steam is trickled through the charge.
Once loaded, detachable, insulated lids are attached to the stills, forming a good, steam-tight
seal, and distillation proceeds in the manner described in Chapter 6. Steam is generated from a
separate boiler at 90110C and uses spent leaf from previous distillations as fuel. Although
multi-tubular condensers are the most efficient, the company in question uses a simple coiled
pipe running through a cold water tank to condense the oil/steam vapours. Each distillation
takes about 1.25 h to complete and yields about 1.01.25 per cent of oil. This represents a yield
of approximately 200 kg of oil per hectare of E. citriodora.
For each distillation charge, the oil is analysed to check citronellal content. The oil is allowed
to stand to cool for 48 h and the fully separated oil is then transferred to separate containers for
storage.

Figure 10.3 Pair of stills sharing a single lid and condenser (photo: J. Coppen).
Figure 10.4 Spent eucalyptus leaf from the distillery being loaded onto lorries for return to the fields
to serve as slow-acting fertiliser (photo: J. Coppen).

Distillation by another Brazilian company utilises 1- or 2-t stills operating in pairs, with one
lid and condenser per pair (Figure 10.3). In this way, one still can be loaded with leaf while the
other, already packed, is being distilled. At the end of this distillation the lid is removed and
transferred to the second still, where distillation commences, while the first still is unloaded and
repacked with fresh material. Distillation usually takes about one hour for E. citriodora and a lit-
tle longer for E. globulus and E. staigeriana. With year-round harvesting and distillation, average
oil yields equate to approximately 140 kg/ha for E. globulus and 100 kg/ha for E. citriodora and
E. staigeriana. Spent leaf from the distillation is returned to the fields to act as a slow-acting
fertiliser (Figure 10.4).
Eucalyptus oil production elsewhere in South America

The most recent estimates of eucalypt plantations (see Appendix 2) show that Argentina, Peru,
Chile and Uruguay all have substantial areas 245,000 ha or more. According to Brown (2000),
Eucalyptus species accounted for 90 per cent of the forest plantation area in Peru in 1995 and
80 per cent of the area in Uruguay. However, none of these countries have ever produced eucalyptus
oil on a scale to match Brazils. The feasibility of exploiting E. globulus for oil production in Peru
has been investigated (Cano Vela 1980 and Ocana Vidal 1983) but no significant commercial
production is known to have developed as a result. Research on oil-bearing eucalypts has been
undertaken in Argentina (e.g. Mizrahi et al. 1972, Argiro and Retamar 1973, De Iglesias et al.
1977, 1980, Mizrahi et al. 1997) and there has been some commercial production of oil.
Chile, Bolivia, Paraguay, Uruguay, Argentina and Colombia have all produced oil at one
time or other but no reliable data relating to current production are known. Chile and Bolivia
produce cineole-rich oil from E. globulus, while Paraguay produces E. globulus and E. citriodora
oils. Chile, Paraguay and Argentina all exported oil in 1999 and/or 2000.
Chile
Although planting of eucalypts on an industrial scale began in Chile in the 1930s it was not
until the late 1980s that rates of planting rapidly increased, reflecting the new-found enthusi-
asm for Eucalyptus as a source of wood for pulp and paper making. By 1992, planting had
reached almost 41,000 ha per year and estimates at about that time put the total area under
eucalypts at 180,000 ha (Davidson 1995, see Appendix 2). More recent estimates put the figure
at 245,000 ha (Appendix 2) and it is predicted that there may eventually be 300,000 ha of euca-
lypt plantations in Chile ( Jayawickrama et al. 1993). Chilean plantings are almost entirely of
E. globulus, mostly in the Valparaiso and BioBio Administrative Regions in the centre of the
country, although E. camaldulensis and non-oil bearing species such as E. nitens, E. delegatensis and
E. regnans are starting to be planted, according to climatic preferences.
Such a massive resource of leaf biomass from a species recognised for its oil quality, E. globulus,
invites exploitation. Chilean production of eucalyptus oil and purified eucalyptol (1,8-cineole)
intended for export began in the 1980s (Anon. 1984a, b) and new investment was still taking
place in 1991 (Anon. 1991). Oil containing 6075 per cent 1,8-cineole is distilled in yields of
1.21.7 per cent from waste leaf. Yields of such leaf from trees planted for wood production
have been estimated at 810 t/ha, equivalent to approximately 100150 kg/ha of oil (Anon.
1987). Other species of eucalyptus have been examined as sources of oil (e.g. Erazo et al. 1990)
but their limited plantings have meant that none has ever come close to matching E. globulus as
a commercial source.

Bolivia
Published accounts of Bolivian oil production are scant but Canadian assistance in the 1980s led to
the establishment of farming cooperatives in Cochabamba, whose aims were to produce essential
oils from locally grown plants (Eberlee 1991). Three oils were chosen for production eucalyp-
tus, mint and lemongrass and by 1991 ten cooperatives had been formed, each using a 5 t
capacity still for distillation. In the case of eucalyptus, the nearby university rectified the crude
oil and the final product was then sold to various Bolivian end-users. Although carried out on a
relatively small scale, it well illustrates the way in which such an operation, if properly organised,
can generate much-needed cash income for rural families.
Research and development

Genetic improvement and the establishment of seed orchards for the production of improved
planting stock are vital for the maintenance of a competitive eucalyptus oil industry but more
research is needed to quantify the likely gains. Xavier et al. (1993) analysed the genetic variabil-
ity of forty-two-month old Brazilian-grown E. citriodora in terms of oil and citronellal content
and found that selection within families provided greater gains than selection among progenies.
The need for careful provenance selection is illustrated by the analyses of Argentinean and
Chilean E. camaldulensis (De Iglesias et al. 1977, Erazo et al. 1990): both sets of plant material
yielded oils richer in p-cymene than 1,8-cineole (Table 10.1). If this species were to be consid-
ered as a potential oil-producing species (rich in cineole) then seed from the well-known Petford
provenance would be better planted and tested.
The Department of Forestry of the Federal University of Viosa, through the Society for
Forestry Research, has always been committed to this kind of research and several collaborative
studies have been undertaken with the company which has been the subject of the case study
above. These have included the genetic improvement of E. citriodora for oil production and the
evaluation of eighteen other eucalypt species and provenances with potential for essential oil
production. In addition to the three species that are currently utilised in Brazil, E. camaldulensis
has been found to have great potential.
Acknowledgements
John Coppen is thanked for providing information additional to that of the authors experience
in Brazil and for information on eucalyptus oil production elsewhere in South America.
Reference
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eucalypts in India
S.S. Handa, R.K. Thappa and S.G. Agarwal
Eucalypts in India
Historical aspects
Eucalyptus was introduced into India as an ornamental tree in the late eighteenth century by the
ruler of Mysore state, Tippu Sultan, who had a great love for gardening. He planted about
sixteen species of Eucalyptus, given to him by his French friends, on the Nandi Hills (then known
as Nandi-Durga) of Karnataka in the period 17821802 (Sreenivasa Murthy and Ramakrishnan
1978, Shyam Sunder 1979). Some of these trees have survived and in 1984, one of the E. tereticornis
trees from Nandi Hills, with a height of 60 m and girth of 4.6 m, was found to have an age of
194 years. Regular planting of Eucalyptus in India started in 1856. In 1860, various species were
planted on a trial basis in northern India: at Lucknow, Saharanpur, Dehra Dun and Agra in Uttar
Pradesh and at Madhopur in Punjab. E. globulus was introduced in the Nilgiris of Madras
Presidency (now Tamil Nadu state) by Captain Dunn and Captain Cotton (Chaturvedi 1976).
Many of these trees, too, still survive, especially along the roadsides.
In the twentieth century, although sporadic attempts were made to grow Eucalyptus alongside
roads and in gardens it was not until the 1950s that serious efforts were made to plant it, following
widespread destruction of Casuarina forests on the Nandi Hills, Mysore state, by the fungus
Trichosporium vesiculosum (Shyam Sunder 1986). Large-scale plantations of Eucalyptus in these areas
were raised from seed collected from plants grown in the Chickaballapur range near the Nandi
Hills. These plants did not clearly resemble any of those grown in the nearby areas and were named
E. chickaballapur, later changed to Eucalyptus hybrid or Mysore gum. This form was discovered,
and its planting promoted, by M.A. Muthana, Chief Conservator of Forests, Mysore state, between
1948 and 1959 (Rajan 1987). It is believed that the tree is a form of E. tereticornis having occasional
hybridisation with E. robusta (FAO 1981). Originally there was evidence of some admixture of the
seed with that of E. camaldulensis but it has now stabilised as a separate entity over many genera-
tions. Brooker (unpubl.) considers it to be locally naturalised E. tereticornis.1
The 1960s saw the introduction of Eucalyptus hybrid on a massive scale throughout India,
from the farthest north to the south. The plantations raised in Karnataka proved it to be the
most adaptable of the eucalypts to the varied climatic and edaphic factors which exist (Shyam
Sunder 1979, Rajan 1987). It was found to be more drought resistant than the original
Australian provenances of E. tereticornis and an excellent soil binder, and this has encouraged its
introduction into other parts of the world (e.g. Sudan).
1 Hereafter in this chapter, because of the very widespread use of the name in India, it is referred to as Eucalyptus
hybrid. However, its near identity with E. tereticornis should be kept in mind.

Present plantations
Eucalyptus hybrid has become the most popular and universal eucalypt in all the low rainfall
areas of India due to its unique ability to adapt to the many different agroclimatic environments,
its ability to withstand drought over long periods, and its excellent coppicing powers. It is
grown on the largest scale in most states of the country, principally for meeting the requirements
of the pulp and paper industry (Chaturvedi 1976, FAO 1981). Although research aimed at util-
ising its leaf oil has been carried out (see below) it has not so far been exploited for this purpose
on a commercial scale. Oil production presently rests with E. globulus and E. citriodora.
Since the introduction of Eucalyptus into India there have been trials on 170 species, varieties
and provenances in many parts of the country (Bhatia 1984), at elevations up to 2200 m and with
an annual rainfall range of 4004000 mm (Chaturvedi 1976). The types of land suitable for
growing some of the important oil-bearing eucalypts are shown in Table 11.1 (Sastry and
Kavathekar 1990).
In Tamil Nadu E. globulus is grown on the high hills, Eucalyptus hybrid in the plains and
E. grandis at medium elevation (Kondas and Venkatesan 1986). The Central Arid Zone Research
Institute, Jodhpur, tested 115 species of Eucalyptus which were growing in comparatively low
rainfall regions of Australia (Muthana et al. 1984). Among the most promising species was
E. camaldulensis and this, too, is now planted. Of late, it is gaining importance and is being
grown in arid zones of Rajasthan, Andhra Pradesh and other states on a plantation scale. These
five species, namely, E. tereticornis (Eucalyptus hybrid), E. globulus, E. citriodora, E. grandis and
E. camaldulensis, have found country-wide acceptance and form the great bulk of eucalypts
in India.
Table 11.1 Suitable land types for oil-bearing eucalypts introduced into Indiaa
Species Land type
E. camaldulensis Hills and plains; arid areas; semi-moist non-forest localities; skeletal
soils; saline and alkaline soils; kankar pans; waterlogged soils; sand
dunes; sandy loam; shallow alluvial soils; ravines; mine sites, especially
of lignite, bauxite and tin
E. cinerea Dry, cold desert
E. citriodora Hills and plains; semi-moist non-forest areas; skeletal soils; ravines;
deep, narrow gullies
E. dives Hills
E. exserta Hills
E. globulus Hills; moist to very moist areas; skeletal soils; laterite soils; controls
erosion with its dense root system
E. globulus subsp. maidenii Hills
Eucalyptus hybrid Hill slopes; semi-moist to very moist soils; non-forest localities; skeletal
soils; laterite soils; coastal sandy soils; deep sandy soils; shallow sandy
loam; saline and alkaline soils; sodic soils; ravines; eroded land; dry
areas; red soils
E. macarthurii Shawalik foothills like Jammu ( J&K) and Palampur (HP) areas
E. sideroxylon Hills; semi-arid areas; saline and alkaline soils; shallow alluvial soils
E. smithii Not successful in India
E. viminalis Hills
E. viridis Arid zone
a Only those species which have been, or are, commercial sources of oil in India (E. citriodora and E. globulus) or
elsewhere, or which have the potential for it (E. camaldulensis and Eucalyptus hybrid), are listed.

Table 11.2 Main areas of eucalypts in India
Region State Area (ha) Year
Northeastern West Bengala 190,000 1987

Northern Uttar Pradesh 200,000 1990
Punjab 95,000 1986
Haryana 40,000 1985
Bihar 21,000 1983
Himachal Pradesh 15,000 1969
Central Madhya Pradesh 57,000 1982
Western Maharashtraa 155,000 1985
Gujaratb 72,000 1983
Southeastern Orissa 50,000 1984
Southern Karnataka 400,000 1986
Tamil Nadu 90,000 1985
Andhra Pradesh 60,000 1980
Kerala 50,000 1987
a A further 190,000 ha (West Bengal) and 150,000 ha (Maharashtra) of mixed forest are
planted, of which one third is estimated to be Eucalyptus.
b A further 120 million Eucalyptus seedlings raised and distributed for planting in rural
areas.
Most eucalypts are planted for the production of pulpwood and firewood but, where it is
economic to do so, waste leaf from the felled trees of E. globulus and E. citriodora is distilled for
oil. The recovery of cineole-rich oil from E. globulus in the Nilgiris marked the beginning of
eucalyptus oil production in India and it now forms a valuable cottage industry for the local
people. A few high oil-yielding clones of E. citriodora, E. globulus and E. camaldulensis have been
successfully cultivated specifically for the production of essential oil, by coppicing younger plants
two or three times a year or collecting leaves every alternate year from plantations raised for wood.
Reliable, up-to-date information is not available but estimates of the main areas in India
under eucalypts, taken from a variety of published sources, are summarised in Table 11.2.
The problem of acquiring accurate statistics is made more difficult by the diverse nature of
the plantings. Apart from large blocks intended for pulp production Eucalyptus is widely planted
as part of agroforestry and social forestry schemes, as well as in strip plantations alongside roads,
railways and canals, and in degraded and otherwise barren areas. In total there are probably
around 7.5 million ha of Eucalyptus in India. This represents about 8 per cent of the global total
(Narwane 1986, Thakekar 1972, Abbasi and Vinithan 1997). Eucalypts are often the dominant
plantation tree and in some states, such as Karnataka, Punjab and Haryana, Eucalyptus planta-
tions account for nearly 1.5 per cent of the total land under cultivation.
Principal eucalypts planted in India
Eucalyptus hybrid
Eucalyptus hybrid, Mysore gum, flourishes from coastal areas to 1000 m altitude, tropical to
warm temperate climates, annual rainfall ranges of 4004000 mm and a wide range of soil types
(Champion and Seth 1968, B. Singh 1977). In the north, it has been successfully raised in
Himachal Pradesh and Jammu and Kashmir at an altitude of 6001200 m. In the plains of
Punjab, Haryana and Uttar Pradesh, large areas have been brought under cultivation under farm
forestry. In Uttar Pradesh, large blocks of plantation are confined to the Tarai and Bhabar tracts,

immediately below the submountain region. On the eastern side of India, in Bihar, most of the
plantations of Eucalyptus hybrid are situated between 100 and 650 m elevation. In West Bengal,
it has been planted in areas with annual rainfall varying from 1000 to 1400 mm and summer
temperatures up to 48C. On the western side of India, in Maharashtra region, it covers a wide
range of climatic and edaphic conditions, from medium rainfall of 1000 mm to high rainfall of
3700 mm. In Gujarat, and in central India (Madhya Pradesh), Eucalyptus hybrid plantations
have been raised in areas where annual rainfall varies from 400 to 2000 mm. The southern states
of Kerala, Karnataka, Tamil Nadu and Andhra Pradesh have the largest areas of Eucalyptus
hybrid and rainfall ranges from 500 to 1500 mm in Tamil Nadu and Andhra Pradesh to
15003500 mm in Kerala.
E. globulus
E. globulus was introduced mainly to create a fuel resource in the Nilgiris plateau (Tamil Nadu)
and so protect the evergreen shoals which were being progressively destroyed for firewood. Its
reputation as the fastest growing and highest yielding species in India led to its increasing popu-
larity in the region (Kondas and Venkatesan 1986, Samraj and Sharda 1986) and the present area
of E. globulus in Tamil Nadu is around 20,000 ha, about half the total in India. Although the
species is used mainly for rayon and paper pulp, and for fence posts, electricity poles and the
construction of farm houses, etc., the distillation of essential oil from its leaves forms a major
cottage industry in the Nilgiris. The leaves are collected from plantations every alternate year or
from standing trees before felling.
E. citriodora
Of the many eucalypts introduced into India, E. citriodora is one of the most valuable. It is par-
ticularly suited to the climate of the Nilgiri Hills and large plantations of it are found there, as
well as the Annamalai Hills and in Kerala, Punjab, Uttar Pradesh, Andhra Pradesh, Karnataka
and Maharashtra. The trees grow well at an elevation up to 200 m, tolerate a rainfall up to
4000 mm, but thrive well even on a poor soil and in a dry climate. About 2000 ha are under
E. citriodora cultivation in the country, of which more than half are in Tamil Nadu. Although the
trees are intended mainly for firewood, timber and pulp, the leaves are used for the extraction of
citronellal-rich essential oil. They are also grown as shelterbelts, wind breaks and for ornamental
purposes along roads or in gardens.
E. camaldulensis
In the arid zones of Rajasthan, Andhra Pradesh and other parts of the country, E. camaldulensis
has been planted. The plantations have been established by providing irrigation in the first two
years because the sites are sandy and characterised by frequent droughts, high temperatures and
desiccating winds. The trees are usually planted alongside canals and roads and in blocks with
irrigation facilities. Plantations are managed on a coppice rotation of 710 years on good sites
and 1415 years on poor sites.
Other Eucalyptus species

E. grandis has been grown successfully on the high ranges of Kerala. Other species which have
been tested include E. globulus subsp. maidenii and E. smithii, both potential sources of oil, and

E. macrorhyncha, E. microtheca, E. regnans, E. terminalis, E. viminalis and E. youmanii. Unfortunately,
E. smithii, which is grown commercially for oil in South Africa, and has shown good promise in
China for oil and fuelwood production, has not been successful in India. The use of E. macrorhyncha
and E. youmanii for the production of rutin in Himachal Pradesh is described later.
Management practices
In India today, forest management and strategy have become more than forestry in the traditional
sense. The focus now is on national development through multipurpose tree cropping, whether it
is in the farm, the forests or among the existing different crop patterns. Trees and forests are
recognised as one of the most important life supporting systems and, since they provide a much
needed protection and production guarantee to the soil, are today the basis of all land manage-
ment systems. Although there has been much heated debate about the ecological impact of
eucalypts (Abbasi and Vinithan 1997), Eucalyptus, being a fast growing species, is favoured by
foresters and farmers for yielding quick economic returns. In some cases the returns are compara-
ble to, or higher, than those from cash crops such as sugarcane, cotton and grapes (Tewari 1992).
Less care and attention is also required compared to other agricultural crops (Kareem et al. 1986).
All the principal Eucalyptus species cultivated in India have good coppicing ability and
most of the plantations are managed under a simple coppice system. Although the use of
short rotations around 710 years in most cases, although this is sometimes reduced to six years
or less by intensive management, including manuring and irrigation enables many consecutive
coppice crops to be produced, repeated harvesting results in loss of vigour and a consequent
decline in wood yields and the number of stumps producing coppice shoots. In practice, there-
fore, the stumps and roots are usually dug out after four rotations and the area replanted (Neelay
et al. 1984). In normal plantations farmers also take interim returns in the form of pruned
materials.
Several recent studies have been conducted in India, examining ways in which Eucalyptus may
be integrated with other crops as part of an agroforestry package and so increase and
diversify the economic returns from the land on which it is being grown. Various models have
been costed in which E. citriodora is grown for oil and poles or fuelwood (Shiva et al. 1988, Shiva
and Jaffer 1990). Scenarios include planting it in blocks within farm forestry programmes,
around borders of agricultural fields and interplanted with essential oil-yielding grasses such as
lemongrass, citronella and palmarosa. In the latter cases, spacings were 2 m ! 2 m and 3 m ! 2 m.
Earlier, Mathur and Sharma (1984) found that wider spacings for Eucalyptus (6 m ! 1 m) gave
maximum returns on farm lands in Uttar Pradesh, Punjab and Haryana. Unfortunately, no reli-
able figures are available to estimate the present scale on which agroforestry practices involving
eucalypts have been taken up or their profitability. Some farmers are known to intercrop such
things as cereals and vegetables, as well as essential oil crops, during the first year and shade-tol-
erant crops such as ginger, turmeric, pineapple and fodder crops during the later years.
Pests and diseases
Insect pests
Besides performing favourably in their introduced habitat when compared to their native habitats
(Sehgal 1983, Basu Choudhuri et al. 1986), Indian eucalypts have been fortunate in suffering
relatively little serious damage from pests and diseases and this has encouraged its planting on a

large scale. About sixty species of insects are associated with Eucalyptus in India (Sen Sharma and
Thakur 1983).
Celosterna scabrator Fabr. (Coleoptera: Lamindae), popularly known as Babul stem and root
borer, has become a major pest of Eucalyptus. Plantations have been reported to be damaged by it
in parts of Andhra Pradesh, Madhya Pradesh, Maharashtra and Uttar Pradesh. The adult insect
attacks tender shoots of the plant, scraping and feeding in the bark up to the sapwood. Only one
egg is laid per plant. On emergence the larvae bore into the stem and root, which are hollowed.
The infested plant shows signs of wilting and yellowing and ultimately dies.
Termite attacks are major problems in dry zones. They cause severe injury and mortality to
eucalypts in the nursery and to young plants. Mortality has been reported to be about
80 per cent (Nair and Varma 1981). Those termite species which cause damage to eucalypts
include Odontotermes assmuthi Holmgren, O. brunneus (Hagen), O. distans Holmgren & Holmgren,
O. feae Wasmann, O. indicus Thakur, O. microdentatus Roonwal & Seri Sarma, O. obesus Rambur,
O. redemanni (Wasmann), O. wallonensis (Wasmann), Microcerotermes minor Holmgren and Microtermes
obesi Holmgren.
Insecticides such as aldrin, clitordane and heptachlor are the most effective as the mortality to
eucalypts is extremely low, ranging from 0 to 4 per cent. They are also effective at the lowest
dosage level (0.25 g active ingredient per seedling). Aldrin, however, is no longer manufactured
in India and its use is being phased out on environmental grounds. Other pesticides such as
those already mentioned and chlordane and chlorpyrifos are equally effective (Rajan 1987,
Tewari 1992).
Diseases
Two fungal diseases, pink disease (Corticium salmonicolor) in plantations (Seth et al. 1978, Sharma
et al. 1984a) and seedling blight (Cylindrocladium quinqueseptatum) in nurseries (Sharma et al. 1984b),
affect eucalypts in high rainfall areas. Cylindrocladium blight assumes epidemic proportions in high
rainfall areas with the onset of the southwest monsoon and causes devastating damage to seedlings
in the nursery, young coppice shoots and one-year-old plants (Anahosur et al. 1977, Rattan et al.
1982). The disease, which initially appears as isolated leaf spots, causes severe defoliation and stem
narcosis and, ultimately, the death of the plant. Although a number of fungicides have been
reported to control the disease, the long-term solution probably lies in identifying resistant geno-
types ( Jayashree et al. 1986).
The nursery diseases can be prevented in high rainfall areas by direct sowing in polythene
bags instead of seed beds, as they are soil-borne in nature (Sharma and Mohanan 1986). The
spread of the disease is reduced considerably by the use of containers since this isolates the
fungal propagules which are present (Sharma and Mohanan 1981). BasalineR (1.0 kg ha"1)
appears to be a promising herbicide for controlling weeds in Eucalyptus nurseries.
Tobacco mosaic disease has been detected in E. citriodora in India. The symptoms of the dis-
ease are a red coloration of the growing ends on 12-year-old plants. The disease adversely affects
the quantity and quality of the oil (Sastry et al. 1971). Root rot, caused by Ganoderma lucidum,
spreads from infected woody debris in the soil. Any such debris should be removed immediately
or isolated by trenching or interplanting with resistant species. In the submountain region in
the north, and on the Central Indian Plateau, Eucalyptus is attacked by the sap and heartrot fun-
gus Trametes cubensis, which enters through injuries caused by Celosterna scabrator (Bagchee 1953).
The threat posed by these diseases in the establishment of eucalypts can be met most effec-
tively by selection of appropriate species and provenances for each geographical area and by
adopting proper silvicultural practices ( Jayashree et al. 1986).

Eucalyptus oil production
Introduction
Despite the large number of species of Eucalyptus which have been tested in India, and the very
large areas of eucalypts which have been planted, only two species, E. globulus and E. citriodora,
have been exploited commercially for oil production (see e.g. Husain et al. 1988). Their use for
this purpose is described below.
The other, most obvious candidate for exploitation is Eucalyptus hybrid, since large quantities
of waste leaf are available after felling the trees from industrial plantations established for pulp
and timber production. However, although a considerable amount of research has been carried
out aimed at determining the composition and properties of the oil and the potential for com-
mercial production (see below), any such potential has not, to date, been realised. Nevertheless,
selection of trees with improved oil characteristics could change the situation and enable the
resource to be utilised for this purpose.
Silvicultural trials and analyses of E. macarthurii, a source of perfumery oil rich in geranyl
acetate, have been undertaken (Madan et al. 1971, Thappa et al. 1979) but despite encouraging
results it has never been exploited commercially in India. Essential oils from other Indian euca-
lypts, none of them produced commercially, are described by Bhalla (1997).
Portable field distillation units employing wood and exhausted leaves as fuel are sometimes
used to distil the oil at the site of felling, and this avoids costly transport of bulky foliage to dis-
tillation units stationed at one place, as well as reducing the cost of fuel per se (Theagarajan et al.
1993). Apart from oil production, use of Eucalyptus leaves as a more general type of fuel is com-
mon and in Karnataka they are preferred by potters for the pottery kilns (Shyam Sunder 1986).
Eucalyptus species used for oil production
E. globulus
The total production of eucalyptus oil in the country from this source is nearly 400 t annually
(S.C. Varshney pers. comm. 1997). In India, E. globulus subsp. globulus is the only source of medi-
cinal oil. It grows well in Nilgiri, Anamalai and Palani hills in south India, and Simla and
Shillong in the north. It is unsuitable for cultivation above 1200 m or at altitudes where the
snowfall is heavy. Leaves and twigs are distilled to yield an oil (0.91.2 per cent, fresh basis) con-
taining about 60 per cent 1,8-cineole which is very popular in south India. Yields of leaves vary
from around 2125 kg to 3375 kg per hectare in the Nilgiris, where the distillation of the oil
is a cottage industry. On an average site approximately 1012 kg ha"1 of oil are obtained,
Table 11.3 (Samraj and Sharda 1986).
Table 11.3 Yields of leaf oil and pulpwood from E. globulus in Nilgiris,
Tamil Nadu
Site quality Average height after Oil yield Pulpwood yield a

10 years (m) (kg ha"1) (m3 ha"1)
Good 2530 1015 450500

Fair 2024 1012 300400
Poor 1519 710 200250
a Per rotation of ten years.

Manian and Gopalakrishnan (1995, 1997) found that oil production in E. globulus is influ-
enced by the ambient temperature and is favoured both seasonally and in altitude terms by
warmer temperatures. Foliar analysis indicated a direct relationship between potassium and oil
yield.
The leaves are collected and dried in the shade for 3 4 days. Copper stills holding about
360 kg of leaves and 160 l of water per charge are generally used for distillation (Rajan 1987).
Each charge takes 8 h for complete distillation. As the oil obtained is somewhat crude, it is
purified by redistillation using a small quantity of caustic soda and water. It is colourless, but
becomes yellowish-pink on long storage and is rectified by redistillation.
E. globulus subsp. bicostata has been shown to yield a leaf oil rich in 1,8-cineole (80 per cent)
(Suri and Mehra 1991) but there are insufficient areas of it planted to make commercial produc-
tion possible at the present time.
E. citriodora
The leaf biomass of E. citriodora yields a lemon-scented oil which is in good demand in India by
the fragrance industry. Despite this, cultivation of E. citriodora as an essential oil crop by farmers
is declining because of alternative, more remunerative, oil and spice crops. Apart from distilla-
tion of leaf from trees grown for wood in places such as the Nilgiris, its present cultivation solely
for oil appears to be limited to just a few areas: Calicut (Kerala, southern India), the Ratnagiri
Hills (Maharashtra, western India) and the Tarai region of Uttar Pradesh (northern India).
Altogether, about 100 t of the oil are produced annually (Singh et al. 1983, S.C. Varshney pers.
comm. 1997).
Of the three most important oil-bearing eucalypts planted in India, most research (as far as
the oil is concerned) has been carried out on E. citriodora and a wealth of knowledge exists on
both chemical and agronomic aspects. The discussion below concerning agronomic and harvest-
ing aspects relates to E. citriodora grown specifically for oil.
Chemical aspects In a study in Jammu, northern India, Kapur et al. (1982) examined the
variability in oil yield and citronellal content amongst twenty-eight individual trees. Trees with
a pubescent leaf type were found to give lower yields but higher citronellal content and
superior odour (1.93.1 per cent yield, fresh basis; 7686 per cent citronellal) than trees with a
non-pubescent leaf (1.44.0 per cent yield; 5075 per cent citronellal). Three to six-month-old
mature leaf gave a higher oil yield (with higher citronellal content) than nine-month-old mature
leaf, indicating that harvesting is best done at 36 month intervals. A consistent pattern of sea-
sonal variation was found with oil yields rising after the summer monsoons and reaching a maxi-
mum during the coldest months before declining. Elsewhere, patterns of variation are different
(e.g. Nair et al. 1983, Rao et al. 1984) and, given the wide range of agroclimatic conditions across
the country, oil yields and the optimum period for harvesting the leaf will vary from region to
region.
Agronomic aspects Kapur et al. (1982) recommended close planting in spring followed by
coppicing the next summer, just before the onset of the monsoons. In this way, a bushy habit was
promoted with high leaf biomass. Two or three harvests could then be taken in northwest India
(in April and November, with a minor crop in July). If the plants were allowed to grow without
any coppicing, then leaf production was poor and, at best, it is two years before the first crop can

be taken. The advantages for total oil yield (on a per hectare per year basis) of coppicing with
fairly frequent harvesting have also been stated by others (e.g. Singh and Atal 1969, Kavulutlayya
1973).
Higher plant densities give a greater leaf biomass (and therefore oil yield) on a per hectare
basis than smaller ones, although the biomass per plant may be less. Thus in Kerala, total
leaf and oil yields went down as the plant spacing increased from 2 m ! 2 m (equivalent to
2500 plants/ha) to 3 m ! 3 m and 4 m ! 4 m (Muralidharan and Ramankutty 1982). P. Singh
(1977) advocated a spacing of 0.90 m ! 0.75 m for raising a commercial crop of E. citriodora.
Ultimately, the spacing employed is a balance between high density and allowing the seedlings
sufficient room to grow and flourish in the time between harvests. Competition from weeds is
more of a problem at the higher spacings and sufficient proximity for adjacent plants to form a
canopy will help suppress weed growth. Application of nitrogen fertiliser is generally beneficial
to leaf production but optimum dose rates appear to be dependent on the nutritional status of
the soil (Muralidharan and Nair 1974, Sirsi et al. 1984).
Harvesting Depending upon conditions, and whether plantations are irrigated or rainfed, either
two or three harvests per year are possible (P. Singh 1977). It is recommended that the first cop-
picing is done at about 3045 cm above the ground and subsequent ones at 7590 cm above
ground. Tips of overgrown shoots are pinched once or twice during a season so as to promote
growth of side shoots and more leaves. For irrigated plantations there is an increase in fresh
weight of herb (leaves # thin branches, approximately 7 : 3) from 7 t in the first year to 30 t in
the second year and 40 t in the third year (per hectare), after which yields stabilise and are
expected to remain economical for about ten years if properly maintained. For unirrigated,
rainfed areas yields are slightly less. Corresponding yields of oil are claimed to be 50 l, 150 l and
200250 l/ha (i.e. about 0.5 per cent on a fresh weight basis).
E. citriodora oil is also produced by the collection of waste leaf from timber plantations.
Yields in this case are reported to be up to 15 kg ha"1 (Fernandez and Suri 1981).
Eucalyptus hybrid
Early reports of Eucalyptus hybrid oil described it as a new source of cineole but also noted its
variability in composition (Theagarajan and Rao 1970; see also Theagarajan and Prabhu 1981,
1988). Typically it contains approximately equal parts of $-pinene, %-pinene and 1,8-cineole
(about 20 per cent each, Mehra and Shiva 1988) and this and subsequent reports have focused on
its potential as a source of pinenes for the manufacture of aroma chemicals rather than its value
as a source of cineole. Both $- and %-pinene are important industrial precursors for a wide range
of fragrance and other materials. Given the very large areas of Eucalyptus hybrid available in
India, and its potential for oil production, Verma et al. (1978) undertook biomass studies to
calculate possible productivity. They stripped the leaves from over 200 trees of a ten-year-old
plantation and found an average of 5.9 kg of green leaf per tree. At a stocking of 1200 trees/ha
this is equivalent to about 7.1 t of leaf per hectare. The average yield of oil was estimated to be
just under 44 kg ha"1.
Shiva et al. (1984, 1989) sampled and analysed E. tereticornis (Eucalyptus hybrid) leaves from
seven, eight, nine and ten-year-old plantations at six different sites in Uttar Pradesh. They con-
cluded that distillation of waste leaf from trees felled for pulp and fuelwood at seven years would
yield maximum quantities of oil and, thereby, substantial quantities of pinenes. However, pinenes

Table 11.4 Variability in leaf oil yield and composition in E. tereticornis (Eucalyptus hybrid) according to
site and age of treesa
Siteb Oil yield $-Pinene %-Pinene $-Terpinene p-Cymene 1,8-Cineole
E. Dehra Dun 1.22.1 11.126.1 4.618.9 20.241.0 5.317.2 21.131.0

Bijnore 1.61.9 14.321.6 13.626.3 3.713.8 10.616.6 24.134.6
Haldwani 1.62.3 13.829.3 13.626.7 1.532.5 4.611.7 11.043.7
Pilibhit 1.02.3 11.524.8 13.324.0 1.128.1 7.9 44.1 8.546.6
S. Kheri 1.42.1 17.037.8 4.125.8 5.08.9 7.724.0 18.543.2
Bahraich 1.12.6 10.717.0 11.031.5 tr8.3 7.424.3 27.950.7
a Figures represent minimum and maximum values at each site for samples taken from plantations aged seven, eight,
nine and ten years. Oil yield: %, moisture-free basis; composition: %, relative abundance.
b All sites are in Uttar Pradesh.
obtained from this source have to compete with cheaper, turpentine-derived pinenes
(i.e. ex Pinus) and, although there is a shortage of turpentine in India, Eucalyptus hybrid oil is not
yet being produced commercially. Nor is there evidence that it is likely to be in the near future.
The variability in yield and composition of E. tereticornis oil is illustrated in Table 11.4
(Shiva et al. 1984, 1989).
End uses and standards for eucalyptus oil

The primary oils are rectified by redistillation and fractionation to maintain quality. Galvanised
iron drums with a capacity of 25 l or 200 l are normally used for storage and marketing of essen-
tial oils, including eucalyptus oil. The drums are then packed in wooden crates. For small-scale
trading 500 ml and 1.0 l glass and aluminium bottles, packed in corrugated boxes, are
commonly used.
Medicinal oil
E. globulus oil is used locally as an antiseptic in the treatment of the respiratory tract, for bron-
chitis and asthma, and as a rubefacient for rheumatism. It is also used as a component of
inhalants, embrocations, gargles, and germicidal and disinfecting preparations. Pure 1,8-cineole
is also produced in large quantities by fractional distillation of E. globulus oil for use in pharma-
ceutical preparations.
To comply with the Indian Pharmacopoeia (IP 1996), E. globulus oil should be colourless to
pale yellow, have an aromatic camphoraceous odour and a camphoraceous pungent taste followed
by a feeling of cold, and contain not less than 60 per cent (w/w) cineole. It should also have a
weight per ml of 0.8970.924 (15.5C), refractive index 1.4571.469 (20C) and optical rota-
tion 0 to #10.
The Bureau of Indian Standards (formerly Indian Standards Institution) also has a require-
ment of not less than 60 per cent cineole for E. globulus oil but the optical rotation range is "5 to
#10 (BIS 1992). Industrial sources are pressing for the minimum cineole content to be raised
to 70 per cent. Such an oil would then be of international quality and comply with the demands
of the British Pharmacopoeia (and some other pharmacopoeias) which specifies a minimum of
70 per cent cineole. Many other new Indian standards have already been introduced as part of a
large revision programme and are in tune with ISO and BP standards. The Indian market, too,
has come to prefer BIS-marked materials and oil which does not initially conform to BIS
standards is often rectified to increase the cineole content.

Perfumery oil
Citronellal-rich oil from E. citriodora is used as a fragrance to perfume soaps, detergents and
disinfectants but its main use is as a starting material for the production of citronellol, hydroxy-
citronellol and hydroxydihydrocitronellal. The latter compound has a fine, flowery odour and is
used in large quantities in perfume compositions for creating linden blossom and lily of the
valley notes.
To meet the requirements of the Bureau of Indian Standards (BIS 1993) E. citriodora oil
should be clear and a colourless to pale yellow or greenish yellow liquid with a citronellal con-
tent of not less than 70 per cent (w/w). It should also have the following specifications (all at
27C): relative density 0.8500.870, refractive index 1.4471.457, optical rotation "2 to #6
and solubility in two volumes of ethanol (80 per cent v/v). The oil should be packed in clean,
dry, air-tight, non-absorbent containers in which it has no action, protected from light and
stored in a cool, dry place.
Use of Eucalyptus in traditional medicine

From time immemorial, aromatic plants have been used in Ayurvedic preparations. Either the
plant itself is used (in whole or in part, e.g. bark, seeds, leaves or flowers) or an infusion or tea.
There is no mention of the use of Eucalyptus in ancient Ayurvedic texts since it has only recently
been introduced into India but, since then, both Ayurvedic and Unani practitioners have found
it to be effective against a wide range of ailments (Singh 1974).
Eucalyptus leaves, kino and oil are used in antiseptic and anti-inflammatory preparations for
both external and internal use and for inhalation. Ayurvedic preparations containing eucalyptus
oil as a major ingredient are used externally for treating rheumatism, headache, bodyache and
abdominal pain (Sharma 1984). It is also used against ailments of the respiratory and gastro-
intestinal tracts (including indigestion, diarrhoea and dysentery), as a vermicide, in the treatment
of skin diseases and as a mouthwash. The cineole-rich oil is used in Ayurvedic preparations for
the treatment of typhoid, haemorrhoidal fever, diphtheria, whooping cough, affections of genito-
urinary organs and for the healing of wounds (Chunekar and Pandey 1988). Tinctures of euca-
lyptus oil in doses of 1020 minims are useful in purulent catarrhal affections of the bladder,
urethra and vagina. Drop doses of oil in combination with water or tepid milk are protective
against cholera.
Production of extracts other than oil from Eucalyptus
Rutin
Eucalyptus leaves are used for composting by farmers (Shyam Sunder 1986) but the only other
extractive utilisation of eucalypts is the production of rutin. Rutin, quercetin-3-rhamnoglucoside,
is a greenish yellow crystalline powder present in the leaves of a number of Eucalyptus species. It
is used in both allopathic and Ayurvedic systems of medicine in the treatment of capillary
fragility, retinitis, rheumatic fever and haemorrhagic conditions (Thappa et al. 1982, 1990). In
India, E. macrorhyncha and E. youmanii have been successfully introduced in Himachal Pradesh as
sources of rutin (Tholamani 1969, Bradu et al. 1982, Sood et al. 1982). In the Palampur area,
12,000 plants have been successfully raised on 4 ha land since 1978 for rutin production. More
recently, high density plantations of E. macrorhyncha and E. youmanii have been established at
Mandi (750 m) and Kullu (1700 m) in Himachal Pradesh, and Ooti (Nilgiris) (R. Kapoor pers.
comm. 1997).

From the mixed E. macrorhyncha and E. youmanii plantation about 15002250 kg/ha of air
dried leaves are harvested annually. The mixed material fetches Rs 1314 (about US$0.35) per
kg and has a rutin content of 68 per cent. The Regional Research Laboratory, Jammu, has
recently developed a process for the simultaneous extraction of essential oils and rutin from plant
materials (Agarwal et al. 1998). Oil rich in eudesmol may be obtained as a by-product from
rutin production. Total production of rutin in India is presently around 2 t annually valued at
about Rs 1500 (US$38) per kg and expected to rise considerably in the future.
Other extractives
Ursolic acid, which has been isolated from Eucalyptus hybrid leaves in 1 per cent yield (Dayal
1987), has a number of potentially useful pharmacological activities. In tests, it has produced a
dose-dependent choleretic effect, significant anticholestatic activity against paracetamol-
induced cholestasis and marked hepatoprotective activity against paracetamol- and galactosamine-
induced hepatotoxicity. Its activity compares favourably with the hepatoprotective drug
silymarin. So far, however, ursolic acid production from eucalyptus has not been taken up
commercially.
Current research and future research needs

In India, current industrial and forestry research on Eucalyptus is mostly directed at the develop-
ment of disease-resistant and genetically improved clones or interspecific hybrids for paper,
pulp, timber and fuelwood purposes. Improvement to oil-bearing eucalypts receives relatively
little attention. Research work conducted at the Forest Research Institute, Dehra Dun, has
resulted in the development of two promising interspecific F1 hybrids between E. tereticornis and
E. camaldulensis, FRI-4 and FRI-5. These improved varieties have yielded 35 times more wood
than the parent species over a ten-year rotation, although the oil composition shows little
improvement in commercial terms (Chaudhari and Suri 1991).
While the needs of the country justify the resources which are put into raising the quality
and productivity of commercial eucalypt plantations in terms of their primary end use, there is
everything to be gained by giving some thought, also, to oil production. While developing
improved strains of Eucalyptus hybrid or other oil-bearing eucalypts for wood and fibre it
requires relatively little extra effort to monitor oil yields and quality (composition). By selecting
germplasm for planting which optimises oil properties but does not adversely affect its silvi-
cultural and primary attributes it may be possible to make the secondary production of oil
from waste leaf economically viable where it was only marginal before. Equally, if the produc-
tion of eucalyptus oil as a primary product from short-rotation, coppiced trees is to withstand
the competition from other, more remunerative crops, then annual oil yields of at least
250 kg ha"1 need to be realisable. Selected, proven germplasm of E. globulus or E. citriodora must
be made available to farmers to achieve this.
Many research institutes have developed broad-based gene pools of Eucalyptus, subject to local
environment selection pressures, to produce improved cultivars with respect to growth and dis-
ease resistance. Superior provenances and better species for each eco-climatic zone are being
selected, germplasm banks are being established and seedling seed orchards and clonal seed
orchards are being raised.
Micropropagation by tissue culture has been tried successfully with some species of
Eucalyptus and thousands of embryoid can be obtained in a single flask. These embryoid can then
be developed into plantlets. Plantlet production by somatic embryogenesis is a superior method

among various tissue culture techniques. Of the various methods of vegetative propagation
tested, side grafting in E. grandis and E. tereticornis, and cutting from fresh shoots in E. globulus
have been successful. Progress so far indicates the possibility of increasing biomass production
and maintaining it at a level of more than three times the present yields by developing high-
yielding and disease-resistant strains through mass selection and recombination breeding.
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Part 3
Biological and end-use aspects

12 Chemistry and bioactivity of the
non-volatile constituents of eucalyptus
Takao Konoshima and Midori Takasaki
Traditional medicinal uses of eucalyptus

From ancient times, the bark and leaves of various species of Eucalyptus have been used as folk
medicines for the treatment of such ailments as colds, fever, toothache, diarrhoea and snake bites
(Ghisalberti 1996). Bark powder has been used as an insecticide in Africa, and a decoction of
leaves has been used for the treatment of colds and bronchitis in Venezuela, Jamaica and
Guatemala. In China, the leaves of Eucalyptus globulus have been used internally for the treatment
of influenza, dysentery, articular pain, tonsillitis and cystitis, and externally for use in the treat-
ment of dermatitis, scabies, erysipelas and burns. The root bark of E. globulus has been used as an
expectorant. The leaves of E. robusta, E. citriodora, E. tereticornis and E. exserta are used for the
same purposes as E. globulus in China ( Jangsu 1977).
Volatile, essential oils have been distilled from the leaves of around 500 species of Eucalyptus
(Coppen and Dyer 1993) and contain many kinds of terpenic compounds, especially 1,8-cineole
(eucalyptol). The oil is used in medicine and perfumery (Coppen and Hone 1992). Eucalyptus oil
for medicinal purposes, usually prepared from E. globulus, E. polybractea or E. smithii, contains not
less than 70 per cent of 1,8-cineole and is included in the pharmacopoeias of many countries, such
as Britain, France, Germany, Belgium, Netherlands, USA, Australia, Japan and China. Eucalyptus
oil has antiseptic properties, which have been established unambiguously in vitro on many germs,
and antimicrobial properties of the oil are described in Chapter 13. Eucalyptol is readily absorbed
by the digestive route, as well as by the cutaneous or rectal route, and is eliminated by pulmonary
or renal excretion. It is also widely accepted that eucalyptus oil (0.050.2 ml/day) has expectorant
and mucolytic properties, and stimulates the bronchial epithelium. Despite the absence of clinical
trials to demonstrate the undeniable therapeutic action of eucalyptus oil and cineole, both products
are ingredients of many proprietary drugs in the form of syrups, lozenges, nasal drops and prepara-
tions for inhalation (Bruneton 1995, Chapter 16 this volume). The essential oils of several species
of Eucalyptus (including E. globulus, E. smithii, E. radiata and E. citriodora) are widely used for aroma-
therapy in Europe and Japan.
Bioactivity associated with the non-volatile constituents

Although phytochemical studies of Eucalyptus have tended to focus on the essential oils, numerous
triterpenoids, flavonoids, tannins and other non-volatile compounds have been isolated from the
plants (Dayal 1988). The rapid growth and increase in woody biomass of Eucalyptus already makes
it useful as a resource for the timber and pulp industries and its secondary metabolites are now
being recognised as potential renewable natural resources for human health care. Many pharma-
cological studies have therefore been made and, where bioactivity has been demonstrated, it has

Table 12.1 Biological activities of some Eucalyptus species and their non-volatile active constituents
Biological activity Species Active compounds Reference
Antioxidant E. cinerea, E. cosmophylla, !-Diketone, Osawa and Namiki (1981,

E. globulus, E. perriniana, ellagic acid 1985), Osawa et al. (1987)
E. viminalis
Inhibitory effect E. globulus Macrocarpal Nishizawa et al. (1992)
on HIV-RTase A, B, C, E
Inhibitory effect E. amplifolia, E. blakelyi, Euglobals Takasaki et al. (1995a),
on Epstein-Barr E. globulus, E. incrassata, Singh et al. (1998),
virus activation E. grandis, E. tereticornis Umehara et al. (1998)
Anti-tumour E. globulus, E. grandis Euglobal-III, -G1 Takasaki et al. (1995b)
promotion (cancer
chemoprevention)
Inhibitory effect on E. sideroxylon Sideroxylonal A, B Satoh et al. (1992)
HeLa cell growth
Inhibitory effect on E. macrocarpa Macrocarpals Murata et al. (1992),
aldose reductase Yamakoshi et al. (1992)
E. sideroxylon Sideroxylonal A, B Singh et al. (1996)
Inhibitory effect on E. amplifolia, E. globulus Macrocarpals Singh and Etoh (1995),
glucosyltransferase Osawa et al. (1995, 1996)
Antibacterial E. macrocarpa Macrocarpals AG Murata et al. (1990, 1992)
Yamakoshi et al. (1992)
E. globulus Macrocarpals Osawa et al. (1996)
? Navarro et al. (1996)
E. perriniana Grandinol Nakayama et al. (1990)
E. sideroxylon Sideroxylonal A, B Satoh et al. (1992)
E. citriodora ? Muanza et al. (1994)
Antifungal E. citriodora ? Muanza et al. (1994)
E. globulus ? Giron et al. (1988),
Navarro et al. (1996)
E. tereticornis Flavonoids Barnabas and Nagarajan
(1988)
Various Eucalyptus spp. ? Egawa et al. (1977)
Antimalarial E. robusta Robustaol A, Xu et al. (1984), Qin and Xu
robustadial A, B (1986), Cheng and Snyder
(1988)
often been found to be associated with the non-volatile, rather than the volatile, constituents of
the plants (Ghisalberti 1996, Singh et al. 1999). Phloroglucinol derivatives in particular
(e.g. robustadials, euglobals, macrocarpals and sideroxylonals) have been found to exhibit
strong biological activities. These include antibacterial, antioxidant, anti-inflammatory,
HIV-RTase inhibitory, antimalarial and anti-tumour promoting activities (Table 12.1).
!-Diketones and polyphenols

Recently, the correlation between oxidative stress and many diseases and natural processes,
including cancer and ageing, has been the focus of investigation, and it has been proposed that
taking antioxidants might be effective for the inhibition of such phenomena. At present, only
tocopherols have been used with safety as natural antioxidative agents.
In order to isolate new types of antioxidant from natural sources, many kinds of natural prod-
ucts have been screened. It is well known that Eucalyptus leaves are covered with a thick wax layer

which might provide antioxidative protection. Accordingly, leaf waxes of seventeen Eucalyptus
species were tested in vitro by Osawa and his co-workers and they reported that several species
showed a strong antioxidative reaction (Osawa and Namiki 1981). As shown in Table 12.2, leaf
waxes of E. citriodora, E. mannifera, E. regnans and E. robusta exhibited no antioxidative activity,
but the other thirteen Eucalyptus species tested did, especially E. dives, E. cosmophylla, E. parvifolia,
E. perriniana, E. rubida and E. viminalis (whose induction periods were more than forty days). The
concentration of one of the !-diketones in the leaf waxes (n-tritriacontane-16,18-dione, which
showed strong antioxidative activity) was also determined. A correlation between the concentra-
tion of n-tritriacontane-16,18-dione and antioxidative activity was observed in all of the species
except E. camaldulensis, E. pauciflora and E. polybractea. For another three species (E. parvifolia,
E. rubida and E. dives), the concentration of this compound in the leaf waxes was not so high but
the activity was very strong. These six species may, therefore, contain antioxidants other than
n-tritriacontane-16,18-dione. Osawa and Namiki (1985) isolated 4-hydroxy-tritriacontane-16,
18-dione (another strong antioxidant) from the leaf wax of E. globulus, in addition to n-tritriacontane-
16,18-dione (Figure 12.1). In this case, the content of leaf wax was more than 0.3 per cent of the
fresh leaves, indicating that E. globulus could serve as an abundant source of antioxidants.
Table 12.2 Antioxidative activitya of leaf wax extracted from some species of Eucalyptus
Species Induction !-Diketone Species Induction !-Diketone

period (days) in leaf wax b period (days) in leaf wax b
E. camaldulensis 20 " E. perriniana #40 $$$

E. cinerea 40 $$$ E. polybractea 30 "
E. citriodora %5 " E. pulverulenta 30 $$
E. cosmophylla #40 $$$$ E. regnans %10 "
E. dives #40 $ E. robusta %10 "
E. globulus 40 $$ E. rubida #40 $
E. gunnii 20 $$ E. viminalis #40 $$
E. mannifera %5 &-tocopherol %20
(100 'g)
E. parvifolia #40 $ BHA (100 'g) #40
E. pauciflora 15 Control 5
a Assayed by thiocyanate method (1 mg of leaf wax extract).

b n-Tritriacontane-16,18-dione quantified by TLC chromatoscanner: $$$$ #80 'g/g, $$$ #50 'g/g,
$$#30 'g/g, $1020 'g/g, "%5 'g/g of fresh leaf, not detected.
O O
C15H31 C CH2 C C15H31 O

O OH
n -tritriacontane-16,18-dione
HO OH
HO O
O O OH O
C15H31 C CH2 C (CH2)11 CH C3H7 ellagic acid
4-hydroxytritriacontane-16,18-dione
Figure 12.1 Chemical structures of some antioxidants from Eucalyptus.

Table 12.3 Antioxidative activitya of ellagic acid (ex Eucalyptus)
IC50
ADP-Fe2$/NADPH ADP-Fe3$/NADPH Adriamycin
Ellagic acid 20 "1 23 " 2 0.10 "0.01

Hexahydroxydiphenic acid #100 #100 7.0 "0.5
Ellagic acid tetraacetate #100 #100 31 "3
&-Tocopherol 320 " 3 0.80 " 0.02 5.5" 0.2
a Measured by inhibition of lipid peroxidation in the rat liver microsome system.

IC50 (concentration ('M) for 50% inhibition of lipid peroxidation.
Another group of strong antioxidants, polyphenols, especially ellagic acid (Figure 12.1), has
been isolated from the bark of Eucalyptus as a by-product of the pulp industry (Osawa and
Namiki 1983, Osawa et al. 1987). As shown in Table 12.3, the antioxidative activity of ellagic
acid is considerably stronger than that of &-tocopherol. Ellagic acid was found to be an effective
inhibitor of in vitro lipid peroxidation by the erythrocyte ghost and microsome test system, and
it was the most potent inhibitor of the perferryl-dependent initiation step of NADPH-depen-
dent microsomal lipid peroxidation. Furthermore, ellagic acid strongly inhibited the lipid
peroxidation induced by adriamycin, and it was deduced that ellagic acid might be valuable
when combined with chemotherapeutic agents such as adriamycin, which normally have the
severe side effect of cardiotoxicity caused by lipid peroxidation.
Ellagic acid has also shown inhibitory effects in vitro on the mutagenicity and carcinogenicity of
benz[a]pyrene-7,8-diol-9,10-epoxide, a potent carcinogen (Sayer et al. 1982).
Other phenolics shown to exhibit strong antioxidant activity include tannins, flavonol
glycosides and acylated flavonol glycosides, all isolated from E. camaldulensis (syn. E. rostrata)
(Okamura et al. 1993).
Macrocarpals
Acquired immunodeficiency syndrome (AIDS) is arguably the most serious disease today, com-
parable to cancer. Ethanol extracts of leaves and calyces of E. globulus have shown significant
inhibitory activity against HIV-RTase, and five active compounds, macrocarpals AE, have been
isolated from the active extracts. The macrocarpals have the combined structures of iso-
pentenylphloroglucinol and a sesquiterpene, and macrocarpal B has exhibited the most signi-
ficant inhibitory effect of HIV-RTase (IC50 5.3 'mol) (Nishizawa et al. 1992). The IC50 for
macrocarpals A, C and E was 10.6, 8.4 and 8.1 'mol, respectively.
The first isolation and structural elucidation of a macrocarpal was that of macrocarpal A, an
antibacterial compound, from E. macrocarpa (Murata et al. 1990). Since then, many other macro-
carpals (BJ and am-1) have been isolated from Eucalyptus (E. macrocarpa, E. globulus and
E. amplifolia), and their antibacterial activities and inhibitory activities on aldose reductase1 have
been reported (Yamakoshi et al. 1992, Osawa et al. 1995, 1996, Singh and Etoh 1995, Singh
et al. 1996). Macrocarpals A, B, C and D inhibit aldose reductase in a concentration range of
1 Aldose reductase is a target enzyme for the control of diabetic complications such as cataract, retinopathy, neuropathy
and nepharcopathy.

2.02.8 'mol (IC50) (Murata et al. 1992). The inhibitory activities on glucosyltransferase and
the cariostatic activities of macrocarpals H, I, J and am-1 (from E. globulus) have also been
reported (Osawa et al. 1995, 1996). In some cases, detailed configurational and conformational
analyses of macrocarpals have been carried out (e.g. Osawa et al. 1997).
The structures of the biologically active macrocarpals are shown in Figure 12.2. There
has been confusion in the literature about some macrocarpals. Firstly, two structurally different
compounds were given the same name, macrocarpal D, by two groups (Nishizawa et al. 1992,
Yamakoshi et al. 1992); the structure containing the seven-membered ring (Nishizawa et al.
CHO CHO
HO OH H HO OH H
OH
OHC OHC
H H
OH OH
macrocarpal-A 9!-isobutyl macrocarpal-C (= -G)

macrocarpal-B 9!-isobutyl
CHO
CHO
HO OH HO OH
H
OHC OHC
OH OH
OH
OH macrocarpal-E
macrocarpal-D
CHO
CHO OH
HO OH
HO OH
OHC
OHC
OH
OH
OH
OH
macrocarpal- I 9!-isobutyl
macrocarpal-H
macrocarpal- J 9!-isobutyl
CHO
HO OH
O
OHC O
OH
macrocarpal-am-1 (= eucalyptone)
Figure 12.2 Chemical structures of macrocarpals from Eucalyptus.

1992) is now accepted as macrocarpal D. Secondly, two different names (macrocarpal-am-1 and
eucalyptone) were given to structurally identical compounds (Osawa et al. 1995, Singh
and Etoh 1995). Finally, macrocarpals C and G have now been shown to be identical (Tanaka
et al. 1997).
Sideroxylonals and grandinal

The dimeric phloroglucinol compounds, sideroxylonals A and B (Figure 12.3), isolated from
E. sideroxylon, have shown strong antibacterial activity against Gram-positive bacteria such as
Staphylococcus aureus and Bacillus subtilis. They have also inhibited the growth of HeLa cells (IC50
for A and B ( 62.5 'g/ml) and aldose reductase (IC50 for A ( 1.25 'mol and B ( 2.47 'mol)
(Satoh et al. 1992). Recently, grandinal (Figure 12.3), which has a similar dimeric phloroglucinol
skeleton, was isolated from E. grandis (Singh et al. 1997).
Robustaol and robustadials

The leaves of E. robusta have been used for the treatment of malaria as a traditional medicine in
China and the benzene-soluble part of the ethanol extract of these leaves showed strong
inhibitory effects against the malarial parasite Plasmodium berghei (Xu et al. 1984). From this
active fraction, robustaol A (a dimeric phloroglucinol) was isolated as an antimalarial con-
stituent, and the structure was confirmed by synthesis (Qin et al. 1981). In addition, robustadials
A and B (combined structure of phloroglucinol and monoterpene) were isolated from other
fractions exhibiting more potent antimalarial activity, although the reported structures were
subsequently revised (Qin and Xu 1986, Cheng and Snyder 1988). The structures of all three
compounds are shown in Figure 12.4.2 Recently, the total synthesis of robustadials A and B and
related compounds was carried out (Majewski et al. 1994, Aukrust and Skattebol 1996). Their
CHO
HO OH CHO
CHO HO OH
HO O CHO
CHO
HO O
OH CHO
OHC OH
OH C
OH
O
sideroxylonal A -isopropyl grandinal

sideroxylonal B -isopropyl
Figure 12.3 Chemical structures of sideroxylonals and grandinal from E. sideroxylon and E. grandis.
2 Note that the spectral data of Qin et al. (1981) support the dissimilar aromatic side chains of robustaol A given by
them and shown in Figure 12.4; the structure given in the reviews by Ghisalberti (1996) and Singh et al. (1999),
which has identical side chains, is incorrect. This has been acknowledged by E. Ghisalberti (pers. comm. 2000 via
J. Coppen).

CHO
HO O
OHC
OH
robustadial A -isobutyl
robustadial B -isobutyl
CH3 CHO
H3CO OH HO OH
CH2
(H3C)2HCOC COCH2CH(CH3)2
OH OH
robustaol A
Figure 12.4 Chemical structures of antimalarial constituents from E. robusta.
antimalarial activity is being studied and the development of new antimalarial agents from
Eucalyptus can be expected.
Euglobals
Euglobals are cycloadducts of formyl phloroglucinol and either mono- or sesquiterpenes, and
exhibit a number of pharmacological activities. Like macrocarpals, they are constituents peculiar
to certain species of Eucalyptus. The phloroglucinol derivatives of Eucalyptus have been reviewed
elsewhere (Ghisalberti 1996, Singh and Etoh 1997, Singh et al. 1999), but the euglobals, which
form a large and important group, are described in more detail here. Their distribution in
Eucalyptus and isolation and structural elucidation using liquid chromatography/mass spectro-
metry (LC/MS) is discussed first, followed by an elaboration of their biological activities. These
latter include anti-inflammatory and anti-tumour promoting activities, and inhibitory effects on
EpsteinBarr virus activation.
Euglobals: analysis and structure elucidation

As indicated above, euglobals are peculiar to Eucalyptus and make up a large group of phloro-
glucinol derivatives. Yields are around 0.030.40 per cent (dry weight basis) in the leaves.
Euglobal-III was first isolated from the buds of E. globulus as a granulation inhibitor and shown
to consist of acylphloroglucinol and terpenoid residues (Sawada et al. 1980). Other euglobals,
with closely related structures, were in the active hexane extract of buds of the plant.
In research on natural products the first essential step is the isolation of pure compounds from
an extract. However, this is a difficult and tedious process when the mixture is complex and
attempts often fail when the mixture is composed of compounds with closely related structures.
In the case of the euglobals from E. globulus, eleven euglobals were isolated by Amano et al. (1981)

using reversed-phase high performance liquid chromatography (HPLC). The structures of these
euglobals were elucidated by means of physicochemical data and X-ray crystallographic analysis
and shown to be acylphloroglucinol-monoterpenes (-Ia1, -Ia2, -Ib, -Ic, -IIa, -IIb and
-IIc) and acylphloroglucinol-sesquiterpenes (-III, -IVa, -IVb, -V and -VII) (Kozuka et al. 1982a,
1982b). Subsequently, in order to search for new euglobals from other Eucalyptus species, a more
efficient analytical method using LC/APCI-MS was developed by our group, and about 50
species of Eucalyptus were examined (Takasaki 1995). From these analyses it has been concluded
that the occurrence of euglobals is restricted to the Symphyomyrtus subgenus of Eucalyptus (see
below). Since the methodologies involved are applicable to other phloroglucinol derivatives they
are described below in some detail.
Analysis of euglobals by LC/MS

Since the 1970s the versatility of HPLC, and its advantages over GC, for the analysis of complex
natural organic mixtures, particularly ones containing non-volatile constituents, has been widely
recognised. The development of soft-ionisation methods for mass spectrometry has also facili-
tated the direct measurement of polar organic compounds without the need for prior chemical
modification. As a result, complex mixtures of euglobals in Eucalyptus have been analysed by
LC/MS using atmospheric pressure chemical ionisation (APCI)-MS techniques. A large number
of euglobals has been detected by such means and their distribution within the genus Eucalyptus
has been examined using the following procedures.
Initial screening
A chloroform extract of the leaves is separated by column chromatography on silica gel into a
number of crude euglobal fractions. Each fraction is tested for the presence of euglobals by thin
layer chromatography (TLC) and LC/APCI-MS. Since euglobals have a distinctive greenish-
yellow fluorescence on the TLC plate when viewed under UV irradiation (365 nm) the primary
screening for euglobals is easily carried out (Takasaki et al. 1994c). Using this procedure,
euglobals were detected in all but three of forty species belonging to the subgenus Symphyomyrtus
(the exceptions being E. aggregata, E. mannifera and E. polybractea), while none were detected in
fifteen species belonging to the subgenera Corymbia3 and Monocalyptus. The results are indicated
in the partial classification scheme shown in Figure 12.5.
Mass spectrometry
After the preliminary separation, each crude fraction is further separated by HPLC and the
eluate led directly into the APCI-MS system. In the case of euglobals with an acylphlorogluci-
nol-monoterpene structure, the molecular weight is 386 and the molecular ion peak is at 387
[M $H$]. Acylphloroglucinol-sesquiterpenes have a molecular weight of 454 and a molecular
ion at 455 [M $ H$ ]. For Eucalyptus species in which no euglobal was detected, no molecular
ion peaks were observed at 387 or 455. The fragmentation of euglobals in electron impact mass
spectra (EI-MS) is shown in Figure 12.6.
The ion m/z 251, formed by loss of the terpenyl part from the euglobal, is a significant peak
and is found in both monoterpene and sesquiterpene types. In the case of the phloroglucinol
3 Corymbia has been elevated to the rank of a separate genus by Hill and Johnson (1995).

Figure 12.5 Partial classification of the genus Eucalyptus indicating the presence or absence of
euglobals.

acylphloroglucinol-monoterpene acylphloroglucinol-sesquiterpene
C23H30O5 C28H38O5
m/z 386 m/z 454
- C13H14O5 - C10H15 - C4H9 - C13H15O5 - C15H23 - C4H9
C10H16 C13H15O5 C19H21O5 C15H23 C13H15O5 C24H29O5

m/z 136 m/z 251 m/z 329 m /z 203 m /z 251 m /z 397
- C3H7 - C4H8 - C3H6 - C4H8
C7H9 C9H7O5 C12H17 C9H7O5

m/z 93 m/z 195 m /z 161 m /z 195
Figure 12.6 EI-MS fragmentations of euglobals.
dialdehyde type, the fragment ion peak at m/z 195 (formed by loss of isobutyl from m/z 251) is
characteristic. This typical fragmentation of euglobals is also observed in APCI-MS and,
together with the total ion chromatogram (TIC) of APCI-MS, provides sufficient information
for euglobals to be detected in complex mixtures. The existence of new euglobals may be
inferred from a combination of APCI-MS and HPLC retention data. As an illustration of the
absence or presence of euglobals in Eucalyptus species, the TICs of E. fastigata and E. cordata are
shown in Figure 12.7.
In the case of E. fastigata, which belongs to the subgenus Monocalyptus, none of the significant
TIC peaks showed an [M $ H+] ion at either m/z 387 or m/z 455 (Figure 12.7a), confirming the
absence of euglobals in the leaves of E. fastigata. In the LC/APCI-MS experiments on E. cordata,
which belongs to the Maidenaria section of the subgenus Symphyomyrtus, four TIC peaks (25)
showed the [M $ H$] ion at m/z 387 and four other peaks (69) showed it at m/z 455; peaks 28
also contained the fragment ion at m/z 195 (Figure 12.7b). From these results and the use of
HPLC retention data, peaks 28 were identified as euglobal-Ib, -Ic, -IIa, -IIb, -III, -IV and -V,
respectively, which have a phloroglucinol dialdehyde moiety. Peak 9 was identified as euglobal-
VII, having an isovaleroyl group on the phloroglucinol moiety.
In E. grandis (subgenus Symphyomyrtus), eight TIC peaks exhibited an [M $ H+] ion at
m/z 387 but none of them contained ions at m/z 455 or m/z 195. The euglobals which are
present therefore have acylphloroglucinol-monoterpene structures with an isovaleroyl group
in the phloroglucinol moiety. From this initial screening preparative HPLC of E. grandis
enabled five new euglobals to be isolated, euglobal-G1, -G2, -G3, -G4 and -G5 (Takasaki et al.
1994c).
Structures and the structural elucidation of new euglobals

To date, thirty-one euglobals have been isolated from six species of Eucalyptus (E. grandis,
E. incrassata, E. amplifolia, E. tereticornis, E. blakelyi and E. globulus). Their structures are shown in
Figures 12.8a and b.
The structures and stereochemistry of the euglobals, detected and isolated using the screening
methods described above, have been elucidated using a variety of spectroscopic techniques,

TIME (min.) TIME (min.)
(a) (b)
0.0 10.0 20.0 0.0 10.0 20.0
6293 176 1
82
2
34
131
5
6
227
78 9
252 TIC
466
455
624 253
397
TIC 387
455
387 251
251
195
100 200 300 400 500 600 700 100 200 300 400 500
SCAN NO. SCAN NO.
Figure 12.7 Total ion chromatogram (APCI-MS) of (a) E. fastigata and (b) E. cordata showing absence
and presence, respectively, of euglobals.
among which nuclear magnetic resonance (NMR) has been pre-eminent. In the case of euglobals
-G1, -G2, -G3, -G4 and -G5 (isolated from the leaves of E. grandis), for example, the results of
high resolution MS suggested that they have a common molecular formula (C23H30O5) and
phloroglucinol-monoterpene structures. The UV, IR and MS spectra of euglobal-G1 and -G2
were similar to those of euglobal-IIc (from E. globulus), indicating the presence of acylphloro-
glucinol moieties. Extensive 1H- and 13C-NMR experiments4 finally enabled the stereochem-
istry and HH distances of euglobal-G2 to be determined (Takasaki et al. 1994c) and these are
depicted in Figure 12.9. It was also deduced that euglobal-G1 was a geometrical isomer of -G2
with respect to the formyl and isovaleroyl groups.
Euglobal-G3, -G4 and -G5 were shown to have the same molecular formula as -G1 and
-G2. Once again, NMR data were invaluable in deducing their relative stereostructures
(Takasaki et al. 1990, 1994c). More recently, seven new euglobals (-G6 to -G12) were isolated
from E. grandis and their structures reported (Singh et al. 1998, Umehara et al. 1998). Other
euglobals which have the acylphloroglucinol-monoterpene structure have been isolated from
E. blakelyi (euglobal-Bl-1), E. tereticornis (euglobal-T1) and E. amplifolia (euglobal-Am-1, -2)
(Kokumai et al. 1991, Takasaki et al. 1994b).
Three new euglobals having an acylphloroglucinol-sesquiterpene structure, euglobal-In-1,
-In-2 and -In-3, have been isolated from the leaves of E. incrassata, along with known euglobals-
III and -V (Takasaki et al. 1994a, 1997).
4 Including NOE (nuclear Overhauser effect), COSY (1H-1H correlation spectroscopy), COLOC (correlation spec-
troscopy via long-range coupling), INADEQUATE (incredible natural abundance double quantum transfer) and
DEPT (distortionless enhancement by polarisation transfer).

R1 R1
HO O HO O
R2 R2
H
OH OH
euglobal-G1 R1 = COCH2CH(CH3)2 euglobal-G3 R1 = CHO

R2 = CHO R2 = COCH2CH(CH3)2
euglobal-G2 R1 = CHO euglobal-G4 R1 = COCH2CH(CH3)2
R2 = COCH2CH(CH3)2 R2 = CHO
CHO H R1
HO HO O
R2
H
OH H OH
O
euglobal-G6 R1 = CHO
euglobal-G5 R2 = COCH2CH(CH3)2
R2 = CHO
CHO R1
H
HO O HO O
R2
H
O OH OH
euglobal-G9 R1 = CHO
euglobal-G8
R2 = COCH2CH(CH3)2
R2 = CHO
CHO O
H
HO O HO O
OHC
O OH OH
euglobal-G11 euglobal-G12
CHO
CHO CHO
HO O
HO O HO O
OHC
H OHC OHC
OH
OH OH
euglobal-Ia1 7-isobutyl euglobal-Ib 7-isobutyl euglobal-Ic 7-isobutyl

euglobal-Ia2 7-isobutyl euglobal-B1-1 7-isobutyl euglobal-IIa 7-isobutyl
Figure 12.8a Chemical structures of euglobals (acylphloroglucinol-monoterpene type) from

Eucalyptus.

CHO R1 CHO
HO O HO O HO O
OHC R2 OHC
H
OH OH OH
euglobal-IIc R1 = CHO
R2 = COCH2CH(CH3)2 euglobal-Am-1 7-isobutyl
euglobal-IIb
euglobal-T1 R1 = COCH2CH(CH3)2 euglobal-Am-2 7-isobutyl
R2 = CHO
Figure 12.8a (Continued).
CHO CHO CHO

HO O HO O HO O
OHC OHC OHC H

OH H OH H OH
euglobal-III euglobal-IVa 7-isobutyl euglobal-V

euglobal-IVb 7-isobutyl
CHO CHO
H H
HO O HO O
R OHC
OH OH
R = COCH2CH(CH3)2
euglobal -VII euglobal-In-1
CHO CHO
H H
HO O HO O
OHC OHC
OH OH
euglobal-In-2 euglobal-In-3
Figure 12.8b Chemical structures of euglobals (acylphloroglucinol-sesquiterpene type) from Eucalyptus.
Biogenesis of euglobals
The probable biogenesis of some of the acylphloroglucinol-monoterpene euglobals is indicated
in Figure 12.10. They are thought to be derived from cycloaddition of the unstable
o-quinonemethide A and the appropriate terpene (&-pinene in the case of euglobal-G1, -G2, and
-G5; !-pinene in the case of euglobal-G3 and -G4). This generates the chroman or spirochroman
skeleton. Euglobal-G6, -G7 and -G8 may be formed from the acylphloroglucinol precursor and
)-terpinene; euglobal-G9, -G10 and -G11 from &-terpinene; and euglobal-G12 from terpinolene.
Similar routes may involve euglobal-T1 and -IIc with &-phellandrene and euglobal-B1-1, -Ib, -Ic

Figure 12.9 Stereochemistry and HH distances of euglobal-G2 as deduced from NMR.
-G1 or -G2
CHO R1
HO OH HO O
-pinene
+
R
CH2OH R2 CH2
OH OH
O
R1 = CHO, R2 = COR -G3 or -G4
R1 = COR, R2 = CHO
-pinene
(A)
CHO
HO O
(A) + - G5
R
-pinene O OH
Figure 12.10 Probable biogenesis of euglobals-G1, -G2, -G3, -G4 and -G5.
and -IIa with sabinene. Biomimetic and other synthetic approaches are gradually shedding light
on the pathways to the euglobal skeleton (e.g. Chiba et al. 1995, 1996).
Anti-inflammatory and anti-tumour promoting activities of euglobals
Anti-inflammatory effects of euglobals

The anti-inflammatory effects of eighteen species of Eucalyptus have been examined in vitro
(Takasaki et al. unpubl.) by measuring granulation inhibitory activity using the fertile egg

Table 12.4 Anti-inflammatory activitya of some Eucalyptus species
Species Inhibition ratiob, % (Survival ratio)
Leaves Stems
E. viminalis 66.7 (11/20) 58.8 (15/20)
E. cordata 62.9 (15/20) 66.1 (16/20)
E. robusta 62.7 (13/20) 45.1 (16/20)
E. cosmophylla 57.9 (18/20) 57.9 (15/20)
E. radiata 57.9 (18/20) 40.3 (17/20)
E. cinerea 56.1 (17/20) 56.1 (16/20)
E. globulus 55.6 (18/20) 44.4 (17/20)
E. parvifolia 54.4 (19/20) 49.1 (15/20)
E. perriniana 48.1 (18/20) 42.6 (20/20)
E. pauciflora 46.3 (16/20) 20.4 (19/20)
E. gunnii 44.4 (19/20) 18.5 (16/20)
E. regnans 39.2 (15/20) 33.3 (15/20)
E. mannifera 38.6 (18/20) 35.1 (17/20)
E. camaldulensis 37.5 (14/20) 35.7 (13/20)
E. citriodora 37.0 (13/20) 42.6 (17/20)
E. niphophila 29.8 (15/20) 26.3 (18/20)
E. ficifolia 29.4 (18/20) 25.5 (18/20)
E. aggregata 24.1 (16/20) 13.0 (16/20)
Berberine 57.1 (17/20)
a Measured as granulation-inhibiting activity.

b Inhibition ratio (%) ((Dry wt in control eggs * Dry wt in test eggs) +(Dry wt in control eggs) ,
100, where Dry wt ( weight of granulation tissue.
Dose: 100 'g/disc chloroform extract of plant, 25 'g/disc berberine chloride.
method of Otsuka et al. (1974). Of the species tested (Table 12.4), eight showed strong
inhibitory activity: E. viminalis, E. cordata, E. robusta, E. cosmophylla, E. radiata, E. cinerea, E. glob-
ulus and E. parvifolia. The inhibitory effects of the extracts of leaves were stronger than those of
stems. It is notable that apart from E. radiata all the active species belong to the Symphyomyrtus
subgenus of Eucalyptus and contain euglobals (Figure 12.5).
Testing of twelve euglobals (-Ia1, -Ia2, -Ib, -Ic, -IIa, -IIb, -IIc, -III, -IVa, -IVb, -V and -VII)
isolated from the leaves of E. globulus as granulation-inhibiting principles showed that nine of
them (Table 12.5) had stronger activities than indomethacin, and similar inhibitory effects to
berberine, both well-known anti-inflammatory agents (Kozuka et al. 1982a,b). The granulation-
inhibiting activity of the euglobals almost certainly derives from the acylphloroglucinol moiety
rather than the terpene.
Inhibitory effects on EpsteinBarr virus activation

Despite substantial progress in our understanding of its development at the molecular level, and
in its treatment, cancer remains a tragic disease and one of the major causes of death worldwide.
The advancement of cancer chemoprevention, as well as the development of still better methods
and drugs for cancer treatment, continues, therefore, to be a much sought-after goal.
The mechanism of chemical carcinogenesis has been explained in terms of either a two-stage
or a multi-stage theory; the latter entails initiation, promotion and progression stages
(Berenblum 1941). Of these stages, the promotion stage is long-term and consists of a reversible
reaction, and the development of inhibitors of promotion has been regarded as the most effective

Table 12.5 Anti-inflammatory activity a of euglobals from Eucalyptus globulus
Sample Dose Granulation tissue Survival ratio

('g/disc)
Dry weight Inhibition
(mg) ratiob (%)
Control 5.6
Euglobal-Ia1 12.5 2.4 57.1 18/20
6.25 3.5 37.5 18/20
Euglobal-Ib 12.5 2.7 51.8 15/20
6.25 3.0 46.4 16/20
Euglobal-Ic 12.5 2.6 53.6 16/20
6.25 3.1 44.6 17/20
Euglobal-IIb 12.5 2.9 48.2 16/20
6.25 3.4 39.3 16/20
Euglobal-IIc 12.5 2.8 50.0 18/20
6.25 3.4 39.3 17/20
Euglobal-III 12.5 2.7 51.8 18/20
6.25 3.4 39.3 18/20
Euglobal-IVa 12.5 2.4 57.1 16/20
6.25 3.5 37.5 18/20
Euglobal-V 12.5 3.7 33.9 20/20
6.25 3.6 35.7 17/20
Euglobal-VII 12.5 3.3 41.1 18/20
6.25 4.1 26.8 18/20
Indomethacin 12.5 4.1 26.8 12/20
6.25 4.2 25.0 12/20
Berberine HCl 25.0 2.4 57.1 17/20
12.5 2.5 55.4 18/20
a, b See footnotes to Table 12.4.
approach to the chemoprevention of cancer. These inhibitors are called anti-tumour promoters.
To search for possible anti-tumour promoters (cancer chemopreventive agents) from natural
sources, the primary screening of many kinds of natural products has been carried out
(Konoshima et al. 1991, 1992, 1996). A suitable method for such screening involves a short-
term in vitro synergistic assay on Epstein-Barr virus early antigen (EBV-EA) activation induced
by a strong tumour promoter, 12-O-tetradecanoylphorbol-13-acetate (TPA). In this assay
method, Raji cells carrying the EBV genome are incubated in a medium containing n-butyric
acid, TPA and various doses of the test compounds. Smears are made from the cell suspension
and the EBV-EA inducing cells are stained by means of an indirect immunofluorescence tech-
nique. Many compounds that inhibit EBV-EA induction by TPA have been shown to act as
inhibitors of tumour promotion in a two-stage carcinogenesis test in vivo (Konoshima et al.
1995, Kapadia et al. 1996).
The potential of Eucalyptus as a source of anti-tumour promoters has been investigated by
Takasaki et al. (1995a,b) and Umehara et al. (1998). In all, twenty-seven euglobals (twenty-one
acylphloroglucinol-monoterpenes and six acylphloroglucinol-sesquiterpenes) isolated from the
leaves of six species of Eucalyptus underwent the primary screening described above. Their
inhibitory effects on EBV-EA activation induced by TPA and the viability of Raji cells are shown
in Table 12.6. Of the test compounds, euglobal-G1, -G2, -G4, -G5, -Am-2 and -III exhibited
significant inhibitory effects (100 per cent inhibition of activation at 1000 mol ratio/TPA and
more than 70 per cent inhibition of activation at 500 mol ratio/TPA) and preserved the high

Table 12.6 Screening of euglobals and macrocarpals from Eucalyptus as anti-tumour promotersa
Sample Concentrationb
1000 500 100 10
Acylphloroglucinol-monoterpenes
Euglobal-G1 0.0 (50) 15.6 (#80) 70.3 (#80) 100.0 (#80)
-G2 0.0 (60) 25.4 (#80) 73.3 (#80) 100.0 (#80)
-G3 10.5 (#80) 23.6 (#80) 65.7 (#80) 100.0 (#80)
-G4 0.0 (70) 26.2 (#80) 68.4 (#80) 100.0 (#80)
-G5 0.0 (70) 0.0 (#80) 55.7 (#80) 93.8 (#80)
-G6 21.7 (70) 68.1 (#80) 80.5 (#80) 100.0 (#80)
-G7 22.3 (70) 64.6 (#80) 81.9 (#80) 100.0 (#80)
-G8 0.0 (70) 40.8 (#80) 78.2 (#80) 91.3 (#80)
-G9 11.3 (70) 49.2 (#80) 84.3 (#80) 100.0 (#80)
-G10 0.0 (70) 44.1 (#80) 68.5 (#80) 100.0 (#80)
-G12 0.0 (70) 59.9 (#80) 71.8 (#80) 100.0 (#80)
-T1 15.6 (#80) 66.9 (#80) 91.3 (#80) 100.0 (#80)
-IIc 7.8 (#80) 62.2 (#80) 89.5 (#80) 100.0 (#80)
-Ia1 c (0) 0.0 (20) 31.5 (#80) 100.0 (#80)
-Ia2 c (0) 0.0 (20) 38.9 (#80) 89.5 (#80)
-B1-1 27.3 (70) 38.1 (#80) 54.5 (#80) 100.0 (#80)
-Ib 18.2 (70) 27.3 (#80) 51.5 (#80) 85.1 (#80)
-Ic 12.1 (60) 30.3 (#80) 69.7 (#80) 100.0 (#80)
-IIa 13.6 (60) 43.7 (#80) 78.5 (#80) 100.0 (#80)
-IIb 0.0 (20) 0.0 (40) 73.6 (70) 100.0 (#80)
-Am-2 0.0 (70) 15.3 (#80) 45.2 (#80) 79.6 (#80)
Acylphloroglucinol-sesquiterpenes
Euglobal-III 0.0 (60) 28.9 (#80) 80.5 (#80) 100.0 (#80)
-IVa 0.0 (20) 0.0 (30) 59.1 (#80) 100.0 (#80)
-IVb 0.0 (10) 0.0 (20) 68.7 (#80) 91.3 (#80)
-V 14.7 (70) 56.4 (#80) 87.1 (#80) 100.0 (#80)
-VII 0.0 (20) 11.4 (30) 70.2 (#80) 100.0 (#80)
-In-1 16.3 (70) 68.3 (#80) 90.5 (#80) 100.0 (#80)
Macrocarpals
Macrocarpal-A 20.6 (10) 48.6 (60) 66.1 (#80) 87.4 (#80)
-B 14.2 (20) 35.7 (60) 63.2 (#80) 100.0 (#80)
-E 17.7 (20) 39.4 (60) 78.1 (#80) 100.0 (#80)
-am-1 33.2 (10) 67.5 (60) 88.0 (#80) 100.0 (#80)
a Measured by inhibitory effects on Epstein-Barr virus early antigen induction. Values represent relative percentages to
the positive control value (100%); values in parentheses are viability percentages of Raji cells.
b Mol ratio/TPA (20 ng (32 pmol).
c Not detected.
viability of Raji cells even at a high concentration. On the other hand, euglobal-Ia1, -Ia2,
-IIb, -IVa, -IVb and -VII showed strong cytotoxicity towards Raji cells (exhibiting less than
40 per cent viability of Raji cells at 1000 and 500 mol ratio/TPA). In addition to euglobals,
macrocarpals A, B, E and am-1 were tested and showed weak inhibitory effects on EBV-EA
activation, similar to those of euglobal-Bl-1 and -IIa, with strong cytotoxicity towards Raji cells
at high concentration (less than 20 per cent viability at 1000 mol ratio/TPA). The use of indirect
immunofluorescence techniques by antigen-antibody reaction requires a high viability of Raji
cells (more than 60 per cent viability) to justify a subsequent in vivo assay.

The inhibitory effects of euglobal-G1, -G2, -G4, -G5, -Am-2 and -III were stronger than
those of glycyrrhetic acid, a well-known potent anti-tumour promoter, and indicate their poten-
tial for cancer chemoprevention.
Anti-tumour promoting activity of euglobal-G1 and -III

In these active euglobals, the yields of euglobal-G1 and -III in the plant are higher than those of
the others, and this has enabled the effects of -G1 and -III on the cell cycle of Raji cells treated
with TPA to be examined by flow cytometry5 (Shimomatsuya et al. 1991). The promoter (TPA)
increased the percentage of the G2 and M phases of Raji cells and decreased the percentages of
both the G1 and S phases in comparison with those of the negative control cultivated without
TPA, as shown in Table 12.7. When treated separately with euglobal-G1 and -III, the effects of
TPA on the cell phases were opposed and at the highest concentration (32 nmol) the percentages
of each phase were near normal. It therefore appears that euglobal-G1 and -III accumulate in
Raji cells in the S phase, dependent on the concentration of these compounds, and that, conse-
quently, the percentage of G2 and M phase is restored to a normal value. Therefore, by influenc-
ing the cell cycle, euglobal-G1 and -III also strongly inhibit one of the biological activities of
the tumour promoter TPA. These in vitro results suggest that euglobal-G1 and -III could be of
considerable value as anti-tumour promoters.
To test the potential of euglobal-G1 and -III as anti-tumour promoters, their inhibitory effects
in the in vivo two-stage carcinogenesis test in mice have been investigated (Konoshima et al. 1993).
One week after initiation of carcinogenic growth with 7,12-dimethylbenz[a]anthracene (DMBA),
TPA was applied twice a week to promote the growth. In the test group of mice, each euglobal
was applied one hour before the TPA treatment. The inhibitory activities were then evaluated by
Table 12.7 Results of testing euglobal-G1 and -III as anti-tumour promoters by

flow cytometry
Treatment % of Raji cells Total
Phase G1 Phase S Phase G2 $M
Medium onlya 61.7 27.9 10.4 100.0

Positive controlb 53.6 8.4 38.0 100.0
Euglobal-G1c
32.0 nmol 60.8 28.8 10.4 100.0
3.2 nmol 57.2 24.0 18.8 100.0
0.32 nmol 52.7 8.2 39.1 100.0
Euglobal-IIIc
32.0 nmol 62.0 29.1 8.9 100.0
3.2 nmol 60.5 25.6 13.9 100.0
0.32 nmol 54.5 8.0 37.5 100.0
a Raji cells cultivated in medium containing 10% fetal calf serum without TPA.
b Treated with TPA (32 pmol) and n-butyric acid.
c Treated with TPA (32 pmol), n-butyric acid and euglobal; 32.0, 3.2 and 0.32 nmol (
1000, 100 and 10 mol ratio/TPA, respectively.
5 Division and proliferation of the cells proceeds via the G1 phase (resting phase after division), S phase (DNA synthetic
phase), G2 phase (resting phase before division) and M phase (mitotic phase). The dispersion and distribution of cells
in each phase can be measured by flow cytometry.

(a) (b)
100 10
Papilloma bearers (%)
Papillomas/mouse
80 8
60 6
40 4
20 2
0 0
0 2 4 6 8 10 12 14 16 18 20 0 2 4 6 8 10 12 14 16 18 20
Weeks of promotion Weeks of promotion
Figure 12.11 Inhibition of TPA-induced tumour promotion by multiple application of euglobal-G1

and -III. Measured in terms of (a) number of papilloma-bearing mice and (b) average
number of papillomas per mouse. Symbols: ! control (TPA alone), " TPA $ 85 nmol
euglobal-G1, TPA $ 85 nmol euglobal-III.
comparing the number (per cent) of papilloma-bearing mice (Figure 12.11a) and the average num-
ber of papillomas per mouse (Figure 12.11b) with those of the control group. As Figure 12.11a
and b indicate, application of euglobal-G1 and -III before each TPA treatment significantly
delayed the formation of papillomas in mouse skin and reduced the number of papillomas per
mouse. Euglobal-G1 and -III exhibited about 55 per cent and 44 per cent inhibition, respectively,
even at twenty weeks of promotion. The results suggest that euglobal-G1 and -III may be valuable
as anti-tumour promoters in two-stage chemical carcinogenesis.
Conclusion
A diverse range of biological activities has been demonstrated by the many kinds of non-volatile
secondary metabolites isolated from Eucalyptus species. The types of metabolites and examples of
their pharmacological actions have been described above. The activities include antioxidative,
antimalarial, antibacterial, antiviral, HIV-RTase inhibitory, aldose reductase inhibitory and cancer
chemopreventive activities. Such broad pharmacological profiles provide a stimulus to further
research and it is likely that more new compounds will be isolated from an increasing number of
Eucalyptus species in the future. The ease of cultivation and rapid growth of eucalyptus makes it,
potentially, a very valuable natural resource for the commercial production of pharmaceuticals,
over and above the present production of eucalyptus oil for medicinal purposes. It is likely that in
the years ahead Eucalyptus metabolites other than the volatile constituents will form part of the
armoury of drugs available to the physician for the treatment or prevention of human diseases.
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13 Antimicrobial activity of eucalyptus oils
Stanley G. Deans
Introduction
The preservative properties of the volatile oils and extracts of aromatic and medicinal plants have
been recognised since Biblical times, while attempts to characterise these properties in the labo-
ratory date back to the early 1900s (e.g. Hoffman and Evans 1911). Martindale (1910) included
Eucalyptus amygdalina (probably the phellandrene variant of E. dives) and E. globulus oils, as well
as eucalyptol (1,8-cineole), in his study of the antiseptic powers of essential oils and although the
carbolic coefficients of eucalyptus oils were not as great as those for oils containing large
amounts of phenolics such as origanum (carvacrol), cinnamon leaf (eugenol) and thyme
(thymol) they did, nevertheless, give some quantitative measure of the antiseptic properties of
eucalyptus leaf oils.
Many volatile oils particularly those of herbs and spices, but including those from Eucalyptus
have been used to extend the shelf-life of foods, beverages and pharmaceutical and cosmetic
products; their antimicrobial and antioxidant properties have also pointed to a role in plant pro-
tection. Such a wide variety of applications, actual or potential, has meant that the antimicrobial
properties of volatile oils and their constituents from a large number of plants have been assessed
and reviewed ( Jain and Kar 1971, Inouye et al. 1983, Shelef 1984, Gallardo et al. 1987, Janssen
et al. 1987, Rios et al. 1988, Knobloch et al. 1989, Pllisier et al. 1994, Shapiro et al. 1994,
Carson et al. 1996, Nenoff et al. 1996, Pattnaik et al. 1996, Baratta et al. 1998a,b, Youdim et al.
1999). In recent years attempts have been made to identify the component(s) of the oils respon-
sible for such bioactivities (e.g. Deans and Ritchie 1987, Jeanfils et al. 1991, Deans et al. 1994,
Lis-Balchin et al. 1998, Daferera et al. 2000, Dorman and Deans 2000). Bhalla (1997) has listed
the organisms against which oils from Indian eucalypts have been tested.
The level of interest in the antimicrobial properties of volatile oils is just one aspect of the
practical potential that such oils have in various protective roles. There also appears to be a
revival in the use of traditional approaches to livestock welfare and food preservation in which
essential oils play a part (Thomann et al. 1997). The use of Eucalyptus and its oils in protecting
stored food products against insect pests is discussed elsewhere (Chapter 14), as are the non-
volatile constituents of Eucalyptus, some of which have antibacterial properties (Chapter 12). It is
intended here to examine the antimicrobial activity of eucalyptus oils and, where it exists, to
assess its potential application to human health care, food preservation and plant protection.
Antimicrobial activity of eucalyptus leaf oils

Unfortunately, much of the research involving the antimicrobial activity of volatile oils, includ-
ing that of Eucalyptus, has been empirical with many of the oils tested simply because they have

been readily at hand. Often, little or nothing has been done to determine the composition of the
oils. Occasionally, the botanical source of the oil is not stated or, where it is, the existence of
chemical variants (chemotypes) is not acknowledged so that even the compositional type cannot
be known with certainty. When commercially available essential oils are tested it is not particu-
larly helpful simply to refer to them by name. As Lis-Balchin et al. (1998) have found, oils of the
same name can have widely different activities. Testing of eucalyptus oil, without any indica-
tion of geographic or botanical source, or composition, is therefore of limited value. As far as
possible, the examples cited below have been chosen only when the eucalyptus oil tested is from
a named species of Eucalyptus. Compositional data are also quoted where possible.
A discussion of the antimicrobial activity of individual eucalyptus oil constituents such as
cineole and citronellal, and the question of possible structureactivity relationships which
might enable one to focus further research on particular types of eucalyptus oil, are deferred till
later, after the results of testing whole oils are examined.
Antifungal activity
Human pathogens
The volatile oil from Eucalyptus camaldulensis (syn. E. rostrata) has been the subject of several stud-
ies where the target organisms were dermatophytic fungi. Singh et al. (1988) tested the oil against
four human pathogens, Trichophyton mentagrophytes, Epidermophyton floccosum, Microsporum canis and
M. gypseum, as well as two storage fungi, Aspergillus nidulans and A. terreus. At concentrations of
10,000 ppm (1 per cent) the oil showed fungicidal activity towards all the test organisms. In a
second study (Ara and Misra 1992), a combination of oils from E. camaldulensis and Juniperus
communis was found to be more effective than either single oil against Epidermophyton floccosum,
M. gypseum and Paecilomyces variotii. The minimum inhibitory concentration (MIC) and time taken
to inhibit mycelial growth were less with the mixture than with the individual oils, suggesting
that there were synergistic interactions between the components present in the two oils.
In a wide-ranging study Pattnaik et al. (1996) tested ten essential oils, one of them from
E. citriodora, against twelve test fungi (mostly human pathogens, with a few plant pathogens):
Alternaria citrii, Aspergillus fumigatus, A. oryzae, Candida albicans, Cryptococcus neoformans, Fusarium
oxysporum, F. solani, Helminthosporium compactum, Macrophomina phaseolina, Sclerotium rolfsii, Sporothrix
schenckii and Trichophyton mentagrophytes. The eucalyptus oil was effective against all the fungi except
M. phaseolina. Seven of the oils (citronella, lemongrass, patchouli, palmerosa, geranium, orange and
aegle) were effective against all twelve fungi, with lemongrass performing the best.
E. pellita oil was found to be active against the human dermatophytes M. gypseum and
T. mentagrophytes, and exhibited greater inhibition than the pine oil from Pinus caribaea (Duarte
et al. 1992).
Organisms involved in food spoilage

The range of fungi that have been screened using eucalyptus oils is very extensive. It has
been shown that inhibition of members of the genera Penicillium (such as the mycotoxigenic
P. citrinum) and Aspergillus (including aflatoxin-producing A. flavus) is readily achievable. Food
spoilage fungi are also inhibited, making eucalyptus a potentially useful oil in the preservation
of foodstuffs.
E. globulus has been tested for its inhibitory effect on the growth of a large number of mould
species frequently involved in food spoilage. Benjilali et al. (1984) tested it using a micro-
atmosphere method, along with five other oils, against thirteen Penicillium spp., six Aspergillus

spp. and sixteen other species. However, while thyme oil was consistently the best performer, the
eucalyptus oil was the least effective. Illustrative results for eucalyptus, rosemary and thyme oils,
including compositional data for the oils, are shown in Table 13.1. Similar results were obtained
using the same oils but an alternative method of testing: E. globulus oil was moderately effective
against Byssochlamys nivea, Geotrichum candidum, Paecilomyces variotii, Penicillium purpurogenum and
Stachybotrys sp., all spoilage organisms, but was the least effective of the oils overall (Benjilali
et al. 1986).
The mycotoxigenic Aspergillus flavus, responsible for the production of aflatoxins in ground-
nuts and other crops, has received much attention from researchers. Several groups have included
eucalyptus oil in screening volatile oils for possible use as antifungal agents although the results
have not been particularly encouraging. Montes-Belmont and Carvajal (1998) investigated the
inhibitory effects of eleven volatile oils, including E. globulus, against A. flavus growing on maize
kernels. The antifungal effect of the eucalyptus oil was described as scanty and no further evalu-
ations of it were carried out. Ansari and Shrivastava (1991) examined the inhibitory power of
eucalyptus oil at three concentrations: the lower two concentrations caused A. flavus growth and
toxin production to be inhibited while the highest concentration resulted in complete inhibition
of growth. After twelve days incubation, however, toxin production was greater than in the
control. It was speculated that the conidia and mycelium were initially under stress, showing
poor growth and low toxin production, but that this was followed by high toxin production in the
late phase of incubation. Masood and Ranjan (1990) have reported on the ineffectiveness of fungi-
toxicant after advanced incubation which stimulated synthesis of aflatoxin, and the correlation
between stress and aflatoxin biosynthesis clearly requires further investigation.
Table 13.1 Antifungal activitya of eucalyptus, rosemary and thyme oils, with composition in terms
of selected constituents (after Benjilali et al. 1984)
Organism Eucalyptus Rosemary Thyme

E. globulus Rosmarinus officinalis Thymus capitatus
Aspergillus flavus ! " """""

A. fumigatus ! "" """
A. niger " " """""
A. repens "" """ """""
Gliocladium roseum " " """""
Mucor hiemalis "" "" """
M. racemosus " " """""
Penicillium clavigerum "" "" """""
P. cyclopium ! " "
P. notatum " ! """""
P. purpurogenum "" " """""
Stachybotrys sp. "" """ """""
Oil compositionb
1,8-Cineole 69 52 !
Camphene 29 4 2
#-Pinene ! 15 Trace
Camphor ! 12 !
Carvacrol ! ! 78
p-Cymene ! ! 15
a Measured by volume of oil required to give complete inhibition: $100 %l (!), 100 %l ("), 50 %l (""),
20 %l ("""), 10 %l (""""), 5 %l (""""").

In tests against the spoilage organisms Aspergillus niger, Penicillium italicum and Zygorrhyncus
sp., E. globulus oil was found to cause reversible inhibition of spore germination (Tantaoui-
Elaraki et al. 1993). At the lowest concentration (0.01 per cent), however, the oil actually caused
stimulation of germination in A. niger conidia and there was evidence to suggest that the fungus
responded positively to the stress caused by low concentrations of oil on the mycelium. Both of
the other oils tested, origanum and mugwort, were more effective at inhibiting spore germina-
tion than the eucalyptus oil and this seems to be in keeping with the observations made by oth-
ers on the effectiveness of different types of oil, namely, phenolic oils $ ketone-rich oils $
cineole-rich oils.
A. niger and Zygorrhyncus sp., as well as the yeasts Candida albicans and Saccharomyces cerevisiae,
and some bacteria, were included by Hajji et al. (1993) in a more comprehensive screening
process involving twenty-one different Eucalyptus oils:
E. amygdalina E. diversicolor E. occidentalis

(syn. E. salicifolia) E. eximia E. oleosa
E. astringens E. globulus subsp. maidenii E. paniculata
E. calophylla E. gomphocephala E. piperita
E. camaldulensis E. longifolia E. sideroxylon
E. citriodora E. macarthurii E. viminalis
E. cladocalyx E. macrorhyncha
E. dealbata E. melliodora
E. cladocalyx oil was the most effective of the oils tested although its yield from the leaves was
relatively poor (0.4 per cent) and not indicative of one that could be produced commercially.
E. citriodora oil was obtained in the highest yield (2.5 per cent) and was moderately effective.
E. citriodora oil has been tested, along with palmarosa (Cymbopogon martinii), against a variety
of organisms, including human and plant pathogens as well as food spoilage organisms:
Alternaria alternata, three Aspergillus spp. (A. flavus, A. fumigatus and A. niger), Cladosporium
cladosporioides, Curvularia lunata and two Fusarium spp. (F. oxysporum and F. solani) (Srivastava
et al. 1993). Both oils contain geraniol and citronellol. Palmarosa was more effective than the
eucalyptus oil at controlling fungal growth, although there was some variability towards differ-
ent organisms. Both oils caused complete inhibition at 0.01 per cent concentration. In another
study involving E. citriodora oil and Cymbopogon martinii (var. motia), Baruah et al. (1996) investi-
gated their antifungal activity towards Fusarium moniliforme, a post-harvest pathogen of cereal
crops. Mentha piperita and Cinnamomum tamala oils were also tested. Using a disc assay and
measuring zones of inhibition on the surface of agar plates, all four oils exhibited activity, with
Cymbopogon martinii the most effective and E. citriodora the next most effective.
Plant protection
It would be of great benefit to be able to employ eucalyptus oil as a natural fungicide, one which
was biodegradable and able to control some of the important plant pathogens. The potential use
of eucalyptus oils in agriculture has been investigated by Singh and Dwivedi (1987) in attempts
to control Sclerotium rolfsii, the causative organism of foot-rot of barley. Four concentrations,
1000 4000 ppm, were used in the poison food technique, where a number of inhibition para-
meters were used as a measure of efficacy, including diameter of the colony on agar media, dry
weight of hyphal mat and reduction in the viability of sclerotia. Of five different oils tested,
E. globulus and Ocimum americanum (syn. O. canum) were the most effective, with MICs of

&4000 ppm. However, further studies showed neem oil (from Azadirachta indica) to be more
effective against S. rolfsii than both E. globulus and O. americanum oils (Singh et al. 1989, Singh
and Dwivedi 1990). Nevertheless, E. globulus oil showed considerable activity towards ten soil
fungi, including the mycotoxigenic Penicillium citrinum; it was most active against Trichoderma
viride (Singh et al. 1989).
The leaf oil from E. camaldulensis was part of a selection of plant oils assayed for antimycotic
activity against the soil-borne fungi Fusarium moniliforme, Phytophthora capsici, Rhizoctonia solani and
Sclerotinia sclerotiorum (Mller-Riebau et al. 1995). The eucalyptus oil, however, was found to have
only slight inhibitory effects in the initial bioassay and was not studied further. Oils from Origanum
minitiflorum, Thymbra spicata and Satureja thymbra were the most active and fungitoxicity was
shown to be due to the presence of carvacrol and/or thymol. Salvia fruticosa, which contained twice
as much 1,8-cineole as E. camaldulensis, had a similar, weakly active profile to the eucalyptus oil.
Eucalyptus oil, along with turpentine and clove oil, completely checked rotting when guava
fruits (Psidium guajava) inoculated with Pestalotiopsis versicolor and Rhizoctonia solani were dipped
in them. However, they had adverse effects on the keeping quality of the treated fruits, in con-
trast to mustard oil which checked the rotting and preserved keeping quality (Madhukar and
Reddy 1989).
The widespread planting of the so-called Eucalyptus hybrid in India (essentially E. tereticornis),
and its leaf oil, have been referred to elsewhere (Chapter 11 this volume). The oil contains
variable amounts of pinenes, 1,8-cineole and p-cymene. In their work to produce true hybrids
with superior growth and wood and oil quality characteristics, Chaudhari and Suri (1991)
reported the oil properties of F1 hybrids of reciprocal crosses E. tereticornis ' E. camaldulensis and
E. camaldulensis ' E. tereticornis, together with those of the parent species. The data include
results from screening the oils for activity against six fungal species: Aspergillus niger, Candida
albicans, Epidermophyton rubrum, Malbranchea pulchella, Microsporum gypseum and Penicillium
notatum. The four oils were active against all six fungi at a dilution of 1 : 500 and the findings
were deemed to bode well for the formulation of control measures against the organisms.
Antibacterial activity
The antibacterial properties of plant volatile oils have been recognised since antiquity and have
been rediscovered in more recent times. Eucalyptus leaf oils have received attention in a number
of studies. Deans and Ritchie (1987) examined the antibacterial effects of fifty volatile oils pur-
chased from a commercial supplier, including eucalyptus, on twenty-five different bacterial gen-
era. The culture collection consisted of food spoilage, food poisoning, human, animal and plant
disease types, along with indicators of faecal pollution and secondary opportunist pathogens.
Eucalyptus oil was most effective against Flavobacterium suaveolens and the dairy organism
Leuconostoc cremoris. However, it was not amongst the ten most inhibitory oils (thyme, cinnamon,
bay, clove, bitter almond, lovage, pimento, marjoram, angelica and nutmeg).
Leaf oils from eight Brazilian-grown eucalypts were tested against Mycobacterium avium by Leite
et al. (1998): E. botryoides, E. camaldulensis, E. citriodora, E. deglupta, E. globulus, E. grandis, E. maculata
and E. tereticornis. M. avium was sensitive to all the oils at 10 mg/ml but only four of them at
5 mg/ml: E. citriodora, E. maculata, E. camaldulensis and E. tereticornis. E. citriodora and E. maculata oils
were particularly rich in citronellal and citronellol. E. citriodora was also one of the better oils tested
by Hajji et al. (1993) against bacteria such as Bacillus megaterium and Staphylococcus aureus although,
like most of the other oils, it was least effective against Escherichia coli.
Another screening programme, this time involving seventeen eucalypts growing in Uruguay, had
earlier been conducted by Dellacassa et al. (1989). Tests were carried out against two Gram-positive

bacteria (Bacillus subtilis and S. aureus) and two Gram-negative ones (E. coli and Pseudomonas
aeruginosa) using volatile oils from the following Eucalyptus species:
E. affinis E. diversicolor E. paniculata

E. amplifolia E. globulus E. pellita
E. botryoides E. lehmannii?1 E. punctata
E. camaldulensis E. longifolia E. sideroxylon
E. citriodora E. maculata E. tereticornis
E. cladocalyx E. melliodora
B. subtilis and S. aureus were most sensitive to the oils and P. aeruginosa least sensitive. For the
latter, oils from only six of the eucalypts showed any inhibition of its growth. Of the seventeen
eucalypts in all, only three (E. affinis, E. cladocalyx and E. diversicolor) inhibited the growth of
all four organisms. Overall, oil from E. globulus (which had the highest cineole content,
64.5 per cent) was the least effective, only showing some activity towards S. aureus. E. citriodora oil
only inhibited S. aureus and E. coli. The authors reported no correlation between either 1,8-cineole
content or the content of any other constituent and antimicrobial activity, and suggested that
the observed activity was due to combinations of more than one oil constituent that are specific
to each test bacterium.
In yet another screening study, Kumar et al. (1988) evaluated freshly distilled leaf oils from
twenty-four species of Eucalyptus against eight Gram-positive and seven Gram-negative bacteria,
some of which were pathogens. The eucalypts were all growing locally in India but unfortu-
nately no information was provided on the chemical composition of the oils:
E. camaldulensis (' 2) E. laevopinea E. rubida

E. crebra E. leucoxylon E. rudis
E. dalrympleana E. melanophloia?2 E. tereticornis
E. deglupta E. microcorys E. viminalis
E. globulus E. parvifolia?3 E. alba ' E. camaldulensis
E. goniocalyx E. regnans E. tereticornis '
E. grandis E. robertsonii E. camaldulensis
E. kirtoniana E. robusta Eucalyptus hybrid
The Gram-positive bacteria tested included Bacillus anthracis, the causative organism of
anthrax, B. subtilis, Micrococcus glutamicus, Sarcina lutea, Staphylococcus aureus and Streptococcus
pyogenes. The Gram-negative bacteria included Enterobacter sp., Listeria monocytogenes, Proteus vulgaris
and Pseudomonas sp. The authors confirmed that in general Gram-negative bacteria are less suscep-
tible than Gram-positive ones. As might be expected, there were differences in inhibitory powers
between the oils: E. tereticornis, one of the E. camaldulensis samples and E. grandis were effective
against thirteen of the fifteen organisms but E. melanophloia and Eucalyptus hybrid showed no
inhibition at all towards any of the Gram-negative bacteria. However, the lack of any composi-
tional data on the oils is a serious weakness in the work there were marked differences in the
effectiveness of the two E. camaldulensis oils, for example, for which no explanation is offered.
1
Authors state E. leshmanii.
2
Authors state E. melanofolia.
3
Authors state E. parviflora so could also be E. largiflorens, for which the former is a synonym.

Of the Gram-positive bacteria, Micrococcus glutamicus was the most sensitive while Streptococcus
pyogenes and Sarcina lutea were the most resistant, fewer than half the oils inhibiting them.
In a study of Malagasy medicinal plants De Medici et al. (1992) analysed oil from the leaves of
E. citriodora and E. globulus, along with an undefined Eucalyptus species. The oils were also tested
for activity against Escherichia coli. Using undiluted oils, E. citriodora oil (71 per cent citronellal)
proved to be inactive while E. globulus (40 per cent cineole) and Eucalyptus sp. (18 per cent cine-
ole, 43 per cent #-pinene) were only weakly active. Comparative results of E. citriodora and
E. globulus oils with those of cineole-rich Cinnamomum camphora and Melaleuca viridiflora,
and eugenol-rich Ocimum gratissimum, are shown in Table 13.2.
E. citriodora oil had earlier been tested against ten bacteria by Siva Sankara Rao and Nigam
(1978). It showed some activity towards eight of them (Bacillus fumilis, Micrococcus sp.,
Pseudomonas solanacearum, Sarcina lutea, Staphylococcus albus, Staphylococcus sp., Shigella sp. and
Xanthomonas campestris) but not to Erwinia carotovora and Pseudomonas mangifera indica. It was not
as effective as the oil from Cinnamomum zeylanicum.
The difficulties in trying to account for the activity of whole oils simply by considering the
activity of individual constituents in isolation has been well demonstrated by Low et al. (1974).
They showed that artificial mixtures of citronellal/citronellol/cineole or citronellal/citronellol in
the same concentrations as found in their sample of E. citriodora oil (i.e. 90 : 7.5 : 2.5 or 90 : 7.5,
respectively) were as effective as the oil itself against Staphylococcus aureus and Salmonella typhi.
This was in contrast to citronellal, citronellol or cineole individually.
The work of Chaudhari and Suri (1991) on E. tereticornis and E. camaldulensis hybrids and their
parents, referred to earlier in connection with antifungal activity, included tests against eight
bacteria: Bacillus mycoides, B. pumilus, Escherichia coli, Proteus vulgaris, Salmonella paratyphi, Sarcina
lutea, Shigella nigesta and Staphylococcus aureus. The four oils were active against all the organisms
at a dilution of 1 : 500.
Production of a soap in which the fragrance also serves as a bacteriostatic agent would have
several advantages and Morris et al. (1979), in the laboratories of International Flavors and
Fragrances, investigated over 520 fragrance raw materials with this objective in mind. The test
samples included both whole oils and pure aroma chemicals and were initially screened against
Escherichia coli, Staphylococcus aureus and Candida albicans. Some 44 per cent of the samples were
inhibitory towards a single organism but only 15 per cent were active against all three.
A lipophilic diphtheroid, Corynebacterium sp., was added to the testing protocol for just over 200
of the original samples, including a commercial cineole-rich eucalyptus oil (7075 per cent). For
eucalyptus oil, as for many of the other materials, the tests gave disappointing results: using the
Table 13.2 Antibacterial activity of Eucalyptus, Cinammomum, Melaleuca and Ocimum oils against Escherichia
coli, with composition in terms of selected constituents (after De Medici et al. 1992)
Oil Inhibitiona Oil compositionb

1,8-Cineole #-Pinene Citronellal Eugenol #-Terpineol
Eucalyptus citriodora 1.0 1.4 71.2 0.3 0.4

E. globulus 4.1 ( 0.8 40.4 32.7 3.0
Cinnamomum camphora 6.8 ( 0.4 56.7 5.0 0.3 6.6
Melaleuca viridiflora 8.1 ( 0.3 72.9 7.2 8.2
Ocimum gratissimum 9.3 ( 0.4 12.0 1.5 1.5 40.3 3.8
a Diameter of inhibition on paper disk (mm).


paper disc diffusion assay there were no zones of inhibition against any of the four test organisms
and MIC values were )1000 ppm. Even the most promising samples had MICs inferior to that
of a commonly used commercial soap bacteriostat and when tested in soaps no reduction of
bacterial counts was obtained. The authors concluded that it did not appear to be possible to
produce a practical antimicrobial soap fragrance. They also pointed out the need for caution
when using experimental zones of inhibition as a measure of antimicrobial activity. Such a
method is dependent on the solubility and rate of diffusion of the test sample in the aqueous
medium and a sample may be much more bacteriostatic than its zone of inhibition might indicate.
One form of testing which is closer, in practical terms, to the way in which human infections
are often spread, namely as bacterial aerosols through coughing and sneezing, has been investi-
gated by Chao et al. (1998). Thieves is a proprietary blend of five volatile oils: E. globulus,
Cinnamomum zeylanicum, Citrus limon, Rosmarinus officinalis and Syzygium aromaticum. In well-
designed experiments subjected to statistical analysis, the blends antibacterial activity was
tested against three Gram-positive organisms Micrococcus luteus, Pseudomonas aeruginosa and
Staphylococcus aureus bioaerosols. Thieves was allowed to diffuse into an enclosed fume hood fol-
lowing spraying of the aerosol-borne bacterial load. P. aeruginosa was the most sensitive to the
treatment, with a 96 per cent reduction in bacterial count following a 10-min exposure.
Inhibition levels for M. luteus and S. aureus were 82 per cent and 44 per cent, respectively. With
further testing the authors suggest that commercial applications could include diffusion of oil
aerosols into air-conditioning systems and spraying in enclosed rooms, both at work and at
home, to prevent the transmission of illnesses through air-borne bacterial pathogens.
Composition and structureactivity relationships

The antimicrobial activity of eucalyptus oils and other volatile oils would be expected to reflect
their composition, the structural configuration of the constituents and their functional groups,
along with potential synergistic interactions between the constituents. Aqueous solubility, and
the ability of toxic compounds to penetrate the fungal or bacterial cell wall, is also likely to be
an important factor and this, too, will be influenced by the chemical nature of individual com-
pounds within the oil. However, while some general observations can be made about the anti-
microbial activity of different classes of terpenes, detailed structureactivity relationships are still
not well understood. Carbonylation of terpenoids, for example, is known to increase their bacte-
riostatic activity but not necessarily their bactericidal activity (Griffin et al. 1999), while alco-
hols possess bactericidal rather than bacteriostatic activity against vegetative bacterial cells.
In a study by Dorman and Deans (2000), a correlation of the antimicrobial activity of the
compounds tested, and their relative percentage composition in the oils, with their chemical
structure, functional groups and configuration has confirmed a number of observations concern-
ing structureactivity relationships made by others. Constituents with phenolic structures, for
example, such as carvacrol and thymol, were highly active against test bacteria, despite their low
capacity to dissolve in water. This may be due to the relative acidity of the hydroxyl group
carvacrol was more active than its methyl ester and, in tests carried out by Knobloch et al.
(1989), methyl and acetyl eugenol were less inhibitory than eugenol; alcohols such as geraniol
and nerol were also less active than phenolic ones. However, Kurita et al. (1981) found that
geraniol was very similar to eugenol (and citronellol) in terms of antifungal activity and only
slightly less active than thymol and isoeugenol. The fact that compounds often have markedly
different responses towards different organisms sometimes makes generalisations unwise.
Citronellol has been found to be relatively inactive towards Escherichia coli and Pseudomonas aeruginosa
but it is strongly active against Staphylococcus aureus (Griffin et al. 1999). Some organisms

are also more sensitive to relatively small changes in structure than others: terpinen-4-ol and
#-terpineol, identical p-menthane tertiary alcohols except for the position of the hydroxyl group,
have identical activity profiles against E. coli, S. aureus and Candida albicans, but the former
retains activity against P. aeruginosa while #-terpineol loses it (Griffin et al. 1999).
The antimicrobial activity of phenolic compounds is further enhanced by alkyl substitution in
the aromatic ring (Kurita et al. 1981, Pelczar et al. 1988). An allylic side chain appears to
enhance the inhibitory effects, chiefly against Gram-negative bacteria. It has been suggested
that alkylation alters the distribution ratio between the aqueous and non-aqueous phases,
including bacterial phases, by reducing the surface tension or altering the species selectivity.
Alkyl-substituted phenolic compounds form phenoxyl radicals which interact with isomeric
alkyl substituents (Pauli and Knobloch 1987). This does not occur with etherified or esterified
isomers, possibly explaining their relative lack of activity.
Aldehydes generally possess powerful antimicrobial activity. The highly electronegative
arrangement of an aldehyde group conjugated to a carboncarbon double bond appears to
enhance activity (Moleyar and Narasimham 1986) and cinnamaldehyde is much more strongly
antifungal than benzaldehyde (Kurita et al. 1981). Such electronegative compounds may inter-
fere in biological processes involving electron transfer and react with vital nitrogen components
such as proteins and nucleic acids, thereby inhibiting growth of the microorganisms. Essential
oils rich in cinnamaldehyde or citral have been linked with consistently high antimicrobial
activity in vitro (Lis-Balchin et al. 1998). Kurita et al. (1981) and Dorman (1999) also found cit-
ral to be moderately active; citronellal, on the other hand, the major constituent of E. citriodora
oil, was only weakly active. Griffin et al. (1999) found citronellal to be active against S. aureus
and C. albicans but relatively ineffective against E. coli and P. aeruginosa.
Using the contact method, Naigre et al. (1996) showed that the bacteriostatic and fungistatic
action of terpenoids was increased when there was a keto group present. Griffin et al. (1999),
however, have found that ketones are variable in their activity carvone was strongly active
against the organisms tested, verbenone was moderately active and menthone was relatively
inactive (the latter in some contrast to the work of Dorman and Deans (2000) who found that
menthone exhibited modest antibacterial activity, particularly against Clostridium sporogenes and
Staphylococcus aureus). Interestingly, piperitone, a major constituent of E. dives oil (piperitone vari-
ant), was also quite strongly active (and more so than carvone against E. coli and S. aureus).
Although Lis-Balchin et al. (1998) demonstrated significant antimicrobial activity for several
Myrtaceae oils, including eucalyptus, they found no correlation between activity and 1,8-cineole
content. E. globulus oil (91 per cent cineole) was less active towards bacteria than E. radiata
(84 per cent cineole) and neither was particularly effective against the fungi tested (Aspergillus
niger, A. ochraceus and Fusarium culmorum). E. citriodora oil (&1 per cent cineole but high in
citronellal) showed much greater antifungal activity.
Terpene hydrocarbons such as #- and *-pinene, limonene and p-cymene have been found to be
inactive towards a variety of organisms (Kurita et al. 1981, Griffin et al. 1999), as have terpene
acetates such as geranyl, linalyl, neryl and #-terpinyl acetates (Griffin et al. 1999). Inactivity has
been attributed to low water solubility and low hydrogen bonding capacity.
An increase in activity dependent upon the type of alkyl substituent incorporated into a non-
phenolic ring structure was observed by Dorman and Deans (2000). The inclusion of a double
bond increased the activity of limonene relative to p-cymene, which demonstrated no activity
against the test bacteria. In addition, the susceptible organisms were principally Gram-negative,
which suggests that alkylation influences Gram reaction sensitivity of the bacteria.
Stereochemistry also has an influence on bioactivity. It has been observed that in some cases
#-isomers are inactive relative to *-isomers (e.g. #-pinene cf. *-pinene) and cis-isomers are

inactive compared to the trans-isomers (e.g. geraniol cf. nerol). Compounds with methyl-isopropyl
cyclohexane rings are most active and unsaturation in the cyclohexane ring further increases the
antibacterial activity, as in terpinolene, #-terpineol and terpinen-4-ol (Hinou et al. 1989).
Investigations into the effects of terpenoids upon isolated bacterial membranes suggest that
their activity is a function of the lipophilic properties of the constituent terpenes (Knobloch
et al. 1986), the potency of their functional groups and their aqueous solubility (Knobloch et al.
1988, 1989). As noted earlier, the importance of water solubility and hydrogen bonding has
been pointed out by others (e.g. Griffin et al. 1999). These interacting factors are not easy to
unravel and different researchers using different procedures and different organisms some-
times obtain results that are difficult to reconcile. In the test conditions used by Knobloch et al.
(1989), *-pinene showed moderate antibacterial activity towards Rhodopseudomonas sphaeroides
although it is insoluble in water; cineole was only slightly active, despite having about the same
water solubility as citronellal, which was very active; and carvacrol and thymol were also highly
active although they were less water soluble than citronellal. The site of action of the terpenoid
appears to be at the phospholipid bilayer of the cell and to be caused by biochemical mechanisms
catalysed by the bilayers. These processes include the inhibition of electron transport, protein
translocation, phosphorylation steps and other enzyme-dependent reactions (Knobloch et al.
1986). Terpenoid activity in whole cells appears to be more complex (Knobloch et al. 1988).
Conclusions
Chemotherapeutic agents, used topically or systemically for the treatment of microbial infections
of humans and animals, possess varying degrees of selective toxicity. Although the principle of
selective toxicity is used in agriculture, pharmacology and diagnostic microbiology, its most dra-
matic application is the systemic chemotherapy of infectious diseases. Plant products which have
been tested appear to be effective against a wide spectrum of microorganisms, both pathogenic
and non-pathogenic. Administered orally, these compounds may be able to control a wide range
of microbes, but there is also the possibility that they may cause an imbalance in the gut
microflora, allowing opportunist pathogenic bacteria, such as coliforms, to become established in
the gastrointestinal tract with resultant deleterious effects. Further studies on therapeutic appli-
cations of volatile oils, including those from Eucalyptus, are needed to investigate these issues, and
to complement the substantial number of analytical and in vitro bioactivity studies that are being
carried out on these natural products.
The potential of eucalyptus oils for use as practical antimicrobial agents remains to be proven.
Some results have been encouraging but others have been less so. The variability is as much a
reflection of the widely differing conditions, procedures and test organisms used by different work-
ers as it is of the compositional variation in the oils themselves. Mixtures of oils, as used by Chao
et al. (1998), may be more effective than single oils, although the choice of which oils to combine
is no easy matter. Prediction of activity in whole oils (or mixtures) based on that of individual con-
stituents is complicated by the existence of synergistic effects, as noted earlier (Low et al. 1974).
In vitro studies have shown that oils from some Eucalyptus species are effective against a range
of pathogens, non-pathogens and spoilage organisms. More comprehensive (and standardised)
tests of oils from a greater number of Eucalyptus species are needed to determine whether such
oils, or formulations containing them, have a major role to play as antimicrobial agents. If they
have, then in vivo studies are needed to assess their efficacy under clinical conditions. With an
increasing public awareness of green issues, plant volatile oils, including those from Eucalyptus,
offer a more eco-friendly alternative to conventional formulations in a number of sectors where
antimicrobial action is desirable.

Acknowledgements
SAC received financial support from the Scottish Executive Rural Affairs Department.
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14 Eucalyptus in insect and
plant pest control
Use as a mosquito repellent and protectant
of stored food products; allelopathy
Peter Golob, Hiroyuki Nishimura and Atsushi Satoh1
Introduction
The ease with which essential oils are obtained from aromatic plants and their diverse chemical
compositions makes them potential sources of natural pesticides either through direct toxicity
or by repellency and they have attracted increasing attention among researchers (as reviewed,
for example, by Singh and Upadhyay 1993). As natural repellents they have seen a resurgence of
interest since the use of synthetic compounds began to displace the large number of essential oils
which were formerly used in the 1930s and 1940s (Curtis et al. 1990). Their volatility has poten-
tial benefits in terms of bringing the pesticide vapour into close contact with the pest while at
the same time not leaving residues which might adversely affect the object being protected, be
this a crop or food product, or, in the case of, for example, a mosquito repellent, the human body.
With the ever-increasing level of air travel the danger of catching malaria and other mosquito-
borne diseases is now a worldwide one and not confined to people living in the tropics.
Citronella oil has been used in commercial repellent preparations and is still popular in
India. In China, essential oils from Mentha haplocalyx and Clausena kwangsiensis have been shown
to repel mosquitoes (Curtis et al. 1990). And essential oils, especially those derived from citrus
peels, have been tested as grain protectants for many years (Golob and Webley 1980). However,
sufficient research has now been conducted to suggest that eucalyptus oil, its constituents or the
leaves from which it is obtained hold, perhaps, most promise of all for use in the battle against
insect pests. As well as exhibiting repellency towards mosquitoes, eucalyptus oil has been found
to be toxic to mosquito larvae and Corbet et al. (1995) suggest that plant essential oils merit
further attention as widely available, environmentally benign mosquito larvicides.
In a few cases, eucalyptus oil-based products have already reached the market place.
Quwenling, made in China from the waste distillate after extraction of oil from the lemon euca-
lyptus, is used for protection against mosquitoes, and the active ingredient has now found a
place in Western human health care as Mosi-guard. This is referred to in Chapter 16 but is
discussed in more detail below.
In many other cases, more research is required, particularly large-scale field trials, to confirm
efficacy and determine the economics and viability of production of the most suitable formula-
tion. Nevertheless, there is hope that in the years ahead more eucalyptus-based products and pro-
cedures will find practical application in the fight against insect pests. Some of the efforts in
1 The section on the use of eucalyptus as a protectant of stored food products is by Golob. The discussion of eucalyptus
as a mosquito repellent and as a source of allelochemicals is by Nishimura and Satoh, with supplementary information
relating to quwenling and the development of Mosi-guard provided by N. Hill, London School of Hygiene and
Tropical Medicine, and described by J. Coppen.

working towards this objective are reviewed below. In the case of insects which damage crops the
number of pests is large (see e.g. Kranz et al. 1977) and many insects have been targeted. The dis-
cussion, here, is limited to those which damage stored food products, a major problem in the
tropics and sub-tropics. This follows a description of eucalyptus-based mosquito repellents and
their active ingredients.
Allelopathy, the effect that one plant has on another through the mediation of naturally pro-
duced chemicals, has also attracted researchers. Aromatic plants such as Eucalyptus release
volatile oils from their leaves which appear to have an inhibitory effect on the growth of under-
storey vegetation and this could lead to the development of natural herbicides. Research aimed
at identifying potentially valuable allelochemicals in eucalyptus is therefore also briefly
reviewed.
Eucalyptus as a mosquito repellent
Introduction
N,N-diethyl-m-toluamide (DEET) has long been used as a repellent against blood-sucking
insects such as mosquitoes. However, DEET has several drawbacks, such as an unpleasant odour
and its skin penetration (Moody et al. 1986). It also behaves as a solvent towards certain plastics
and synthetic rubber and so care has to be taken to avoid contact with glasses and watch straps.
There would be advantages, therefore, in finding natural repellents without these undesirable
properties. The use of citronella oil was referred to earlier but in an assessment of twelve repel-
lent formulations on the European market, those with citronella as the active ingredient rated
considerably worse than those with synthetic active ingredients (Curtis et al. 1990). Neem oil
has also been tested (Sharma and Dhiman 1993).
Eucalyptus citriodora
It has long been known in China that oil from the lemon eucalyptus, E. maculata citriodon, has
some repellent effect on mosquitoes.2 When the active fraction was found to be concentrated in
the waste distillate after extraction of the oil the active principle was identified as p-menthane-
3,8-diol. The product, and its effectiveness against Aedes aegypti, A. albopictus and A. vexans, was first
described by Li et al. (1974) (cited, and with data reproduced, in Curtis et al. 1990) and is sold in
China as quwenling (effective repeller of mosquitoes). Although subsequent studies in the
West have found it to be less persistent than DEET (e.g. Schreck and Leonhardt 1991) it has been
so successful that it has largely displaced the synthetic dimethyl phthalate from the Chinese mar-
ket. As well as mosquitoes it gives protection against midges, tabanids and land leeches. In addi-
tion to not damaging plastic materials its mammalian toxicity is lower than that of DEET, with
mouse oral and dermal LD50 values of 3.2 and 12 g/kg, respectively (Curtis et al. 1990).
Using a combination of bioassay and chemical and analytical methodologies, Nishimura et al.
(1986) have also searched eucalyptus for compounds with repellent activity against mosquitoes.
Using Aedes albopictus, the repellent activities of the essential oils of several species of Eucalyptus,
including E. citriodora, were tested. The oils were obtained by steam distilling acetone extracts of
the leaves. The results are shown in Table 14.1.
2 Published accounts all use the name Eucalyptus maculata citriodon but this is not a recognised species name. However,
E. citriodora oil is produced in large quantities in China and its constituents are the same as those described for
E. maculata citriodon. This, together with the fact that Nishimura et al. (1986) have isolated the same active principle
from E. citriodora, makes it likely that the latter species or something very close to it chemotaxonomically is the
eucalypt in question.

The essential oils of E. citriodora and E. camaldulensis exhibited higher repellent activity than
the oils from the other species. Column chromatography of the E. citriodora oil gave two crys-
talline compounds with high activity, (!)-p-menthane-3,8-cis-diol and (!)-p-menthane-
3,8-trans-diol, Figure 14.1 (Nishimura et al. 1986, Nishimura and Mizutani 1989). These
compounds had earlier been identified by Nishimura et al. (1982, 1984) as potent allelochemicals
(see below). All of the enantiomers of the cis and trans diols exhibited approximately the same
activity as the natural racemates.
Table 14.1 Repellency of the volatile oils of some Eucalyptus species against
mosquitoes, Aedes albopictus
Species Repellency (%)a
1% conc. 0.1% conc.

E. camaldulensis 93 60
E. citriodora 90 43
E. radiata 54 24
E. globulus 30
E. viminalis 27
E. pulverulenta 16
Cinnamomum camphorab 0 0
a Repellency % " {(total no. mosquitoes # attracted mosquitoes) $ total no. mos-
quitoes} %100.
b Oil from this species is known to repel insects such as Coleoptera and was used to
compare eucalyptus.
7
6 H CH3 H CH3
1 2
4
H OH
5 3
CH3 CH3 CH3 CH3 H
9 8 10 OH
OH OH
()-p-Menthane- ()-p-Menthane-
3,8-cis-diol 3,8-trans-diol
OH CHO
OH
4-Isopropylbenzyl (+)-Eucamalol
alcohol
Figure 14.1 Chemical structures of the mosquito repellents from leaves of E. citriodora (p-menthane-3,
8-cis- and trans-diol) and E. camaldulensis (4-isopropylbenzyl alcohol and (&)-eucamalol).

Table 14.2 ED90 values for five mosquito repellent formulations, three of them
derived from Eucalyptus citriodora, against Anopheles gambiae
ED90
(l or g product/cm2) (l or g a.i./cm2)
PMDa liquid (50% a.i.b) 0.65 0.33

PMD gel (50% a.i.) 0.67 0.34
PMD stick (50% a.i.) 0.72 0.36
Autan stick (20% DEET) 0.48 0.10
Citronella oil (50% a.i.) 1.37 0.68
a p-Menthane-3,8-diol formulation.
b Active ingredient.
Further developments in the West, building upon the Chinese work on quwenling, have
recently led to the introduction of a new repellent preparation Mosi-guard Natural. Although
still produced from the lemon eucalyptus and containing p-menthane-3,8-diol as the active
ingredient, it is obtained, this time, from the eucalyptus oil itself, rather than the waste distil-
late. The extraction process was developed at University College, London, and the final formula-
tion contains a patented mixture of isopulegol and citronellol as well as p-menthane-3,8-diol
(Trigg and Hill 1996). Laboratory and field testing of the formulation have confirmed its effi-
cacy as a repellent against the malaria vectors Anopheles gambiae and A. funestus, as well as the bit-
ing midge Culicoides variipennis, the deer tick Ixodes ricinis and the stable fly Stomoxys calcitrans
(Trigg 1996, Trigg and Hill 1996). In tests against A. gambiae, ED90 values (the doses calculated
to give 90 per cent protection against bites) for three forms of the eucalyptus preparation com-
pared favourably with Autan stick and were superior to citronella oil (Table 14.2). It was con-
cluded that the level and duration of protection was comparable to that afforded by DEET
(Trigg 1996). Acute toxicological studies have demonstrated minimal toxicity in rats (oral and
dermal LD50 values of 2.4 and '2 g/kg, respectively).
Eucalyptus camaldulensis
Guided by bioassay using Aedes aegypti, research by Watanabe et al. (1993) on the essential oil
from E. camaldulensis has yielded two mosquito-repellent compounds, 4-isopropylbenzyl alcohol
and a new compound, (&)-eucamalol (3-formyl-6-isopropyl-2-cyclohexen-1-ol), Figure 14.1.
(&)-Eucamalol and its 1-epimer were synthesised from (S)-(#)-perillaldehyde to determine
the absolute configuration and to compare the repellent activities of the two compounds. The
absolute configuration of (&)-eucamalol was determined to be (1R, 6R)-(&)-3-formyl-6-
isopropyl-2-cyclohexen-1-ol (Satoh et al. 1995).
The repellent and feeding inhibitory activities of synthetic eucamalol and its epimer were
evaluated using Aedes albopictus as the test mosquito strain (Table 14.3). The activities of the two
epimers were approximately the same and both were as effective as DEET (Satoh et al. 1995).
Eucalyptus as a protectant of stored food products
Introduction
In the developed world food crops are quickly removed from the farm and processed by drying,
canning or freezing for storage before consumption. In the developing world, harvested produce

Table 14.3 Repellency and feeding inhibition of (&)-eucamalol and its (#)-3-epimer
against Aedes albopictus
Repellency/Feeding inhibition (%)a
500 mg/m2 250 mg/m2 50 mg/m2
(&)-Eucamalol 100/100 100/100 84.2/74.5

(#)-epi-Eucamalol 100/100 100/100 75.0/65.0
DEET 100/100 100/100 80.0/85.0
a Repellency calculated as indicated in Table 14.1. Feeding inhibition % "{(total no. mosquitoes #
blood-sucking mosquitoes) $total no. mosquitoes} %100.
is infrequently processed. Instead, it is usually stored for long periods as raw commodities or as
flour on the farm or in large central storage facilities such as bag stores or silos. Farmers in the
tropics and sub-tropics may store grain for a year or more in small granaries at the homestead in
order to provide staple food for their family until the next harvest. During storage, durable food
commodities, such as cereals and pulses, are susceptible to biodeterioration, particularly as a
result of insect infestation, and to avoid severe quality and quantity loss action must be taken to
protect commodities against such an insect attack.
Even in some processed foods mites can be a potential problem in storage and may cause gas-
trointestinal disorders and allergic dermatitis in humans or animals consuming them or coming
into contact with them (Perrucci 1995).
During the last fifty years contact insecticides have been widely used to protect stored food
produce against insect infestation. Contact insecticides, such as malathion and pirimiphos-
methyl, have been used to provide both prophylactic and long-term protection of the produce
for large-scale storage and for individual farmers who may only want to protect the contents of a
few sacks of grain. Farmers are able to use various types of contact insecticide formulation to pro-
tect their stored crop. The dilute dust is specially formulated for use by the individual who has
only small quantities of grain to treat and who does not possess any sophisticated application
equipment. Such a dust can be applied with a shovel and it requires no prior dilution with water.
However, stable dust formulations are difficult to produce and their shelf life is quite short. They
are also difficult to package and transport because they are bulky and farmers often complain
that they are not available when needed. Other insecticide formulations, which are more appro-
priate for treating larger quantities of commodity, are used as liquid sprays after being diluted
with water or light oil and require spraying equipment for their application.
A major constraint on the use of synthetic protectants, and one which has become an
increasing problem in recent years, is that of insect resistance. Resistance occurs when dosages
that would have been expected to completely kill a population are no longer effective. In many
cases, resistance can be overcome by increasing the dosage but this usually makes the treatment
both uneconomic and impractical. The widespread occurrence of resistance has lead to the exclu-
sion of malathion as a storage protectant in many countries. In recent years, resistance has been
detected in the use of other storage chemicals, including pirimiphos-methyl and fenitrothion.
Concerns regarding environmental contamination by pesticides, together with the more
specific problems associated with the use of insecticides, have led to a search for more natural
and environmentally friendly protectants. For on-farm use any alternative must be cheap, locally
available and safe to use. Plants fill these criteria in general terms and they have traditionally
been used by farmers for insect control, both to protect the growing crop and as storage protec-
tants. Plants are often used after drying, as fine powders, and are applied in a similar manner to

dilute dust insecticide formulations. Furthermore, because the parts of plants which are used as
protectants contain a mixture of chemical constituents, more than one of which may have an
insecticidal effect, they are either less likely to induce resistance or resistance will occur much
more slowly in the pest population. However, even though a plant may have been used for gen-
erations as a storage protectant (Golob and Webley 1980) it may not necessarily be particularly
effective or safe. Exhaustive testing is required to identify any potential toxicant effect which
regular use of the plant might cause, and to define optimum methods for application.
Although more than 100 plants have been assessed as grain protectants (Dales 1996) only
two, Chrysanthemum cinerariaefolium (pyrethrum) and Azadirachta indica (neem), have so far been
exploited commercially for this purpose. The attractions of essential oils as natural pesticides
have already been referred to and some of the research aimed at determining the potential of
Eucalyptus and its leaf oils for protecting stored food products is reviewed below.
Eucalyptus as a storage insecticide

There is anecdotal evidence that Eucalyptus leaves have been used traditionally in Africa to protect
insect infestation in stored grain. For example, farmers in the Teso district of Uganda mix dried
powdered leaves with sorghum and grain legumes to prevent insect damage (M. Verstaag pers.
comm.). However, there is a dearth of documented evidence describing the practical use of this
plant by farmers or its efficacy under these conditions. Most studies on the insecticidal effects of
eucalyptus on storage insect pests have been confined to the laboratory to petri dishes and small
glass jars and so, despite promising experimental work, it is not possible to confirm their real
potential as grain protectants.
Researchers have investigated the effects of eucalyptus on pests which attack cereals
including primary feeders which attack whole grain, such as Sitophilus oryzae (L.) (Curculionidae:
Coleoptera), and secondary feeders which infest flour, such as Tribolium castaneum (Herbst.)
(Tenebrionidae: Coleoptera) and insects which damage grain legumes, including Callosobruchus
maculatus (Fab.) (Bruchidae: Coleoptera) and Acanthoscelides obtectus (Say) (Bruchidae: Coleoptera).
Several other investigations have been conducted to assess the effects of eucalypts on mites,
which occur on both processed and unprocessed food, and on Lepidopteran pests. Research
has tended to focus on the effects of leaf oils or leaf extracts, including pure chemicals such
as 1,8-cineole, an important constituent of many eucalyptus leaf oils. Eucalyptus species
which have been tested, together with the pests they have been tested against, are shown in
Table 14.4.
Effects on insect pests of cereals

A recent study (Prates et al. 1998) assessed the vapour effects of 1,8-cineole (from Eucalyptus) and
limonene (derived from Citrus) on adult T. castaneum and Rhyzopertha dominica (Fab.)
(Bostrichidae: Coleoptera) in a gas-tight chamber. Cineole led to 100 per cent mortality of
R. dominica after 24 h but only 58 per cent control of T. castaneum. Both insect species were also
exposed to contact with treated surfaces, filter papers and small quantities of treated wheat.
Contact tests using grain were more sensitive than those using filter paper. Good control was
achieved with both compounds. In the vapour phase cineole was more effective against
R. dominica than against T. castaneum and was slightly more effective than limonene against the
former. Contact toxicity towards both insects was greater for cineole than limonene. The same
research group has studied the effects of cineole and limonene on S. oryzae and S. zeamais Motsch.
(Curculionidae: Coleoptera), another pest of the tropics and sub-tropics (Santos et al. 1997).

Table 14.4 Species of Eucalyptus (as leaf, oil or extract) tested for efficacy against stored-product insect and arachnid pests
Insect species Insect name/type Commodity type E. citriodora E. globulus E. camaldulensis E. tereticornis Unknown a
Sitophilus granarius Granary weevil Cereals Sharaby (1988)

Sitophilus oryzae Rice weevil Cereals Gakuru and Foua-Bi Sharaby (1988) Sarac and Tunc Gakuru and Ahmed and
(1995, 1996) (1995a,b) Foua-Bi (1995) Eapen (1986)
Sitophilus zeamais Maize weevil Cereals Sasaki and
Calafiori (1987)
Stegobium paniceum Drug store Flour Ahmed and
beetle Eapen (1986)
Rhyzopertha dominica Lesser grain Cereals Thakur and Dakshinamurthy Santos et al. (1997)
borer Sankhyan (1992) (1988), Singh Prates et al. (1998)
et al. (1996a,b)
Tribolium castaneum Red flour Flour Santos et al. (1997)
beetle Prates et al. (1998)
Tribolium confusum Confused flour Flour Thakur and Sarac and Tunc
beetle Sankhyan (1992) (1995a,b)
Acanthoscelides Pulse beetle Beans Faroni et al. (1995) Regnault-Roger Stamopoulos
obtectus and Hamraoui (1991)
(1993), Regnault-
Roger et al. (1993)
Callosobruchus Cowpea weevil Cowpea, gram Pajni and Gill (1991) Pajni and Gill Gakuru and
maculatus Gakuru and Foua-Bi (1991) Foua-Bi (1995)
(1995, 1996)
Callosobruchus Adzuki bean Cowpea, gram Ahmed and Eapen
chinensis weevil (1986)
Corcyra cephalonica Rice moth Wheat Pathak and
Krishna (1991)
Ephestia kuhniella Mediterranean Wheat Sarac and Tunc
flour moth (1995a,b)
Sitotroga cerealella Angoumois Paddy Dakshinamurthy
grain moth (1988)
Phthorimaea Potato tuber moth European potato Kroschel and
operculella Koch (1996)
Tyrophagus longior Mite Processed Perrucci (1995)
products, flour
Tyrophagus Copra mite Processed Miyazaki (1996) Gulati and Mathur
putrescentiae products, flour (1995)
Dermataphagoides Mite Processed Miyazaki (1996)
farinae products, flour
a Species not declared or tests conducted using extracts, oils or isolates, for example, 1,8-cineole.

Although 1,8-cineole is an obvious candidate for being the active constituent of cineole-rich
eucalyptus oils which prove positive in bioassay, possible synergistic effects make it desirable to
test whole oils as well as focusing on individual chemicals. Furthermore, although the work of
Prates et al. provides an indication of the effects that cineole may have under real conditions it
does ignore a major consequence of using R. dominica as a test insect. This species completes its
life cycle inside grain and the larval instars cause a great deal of damage. Any assessment of the
effect of eucalyptus on storage pests must include tests against those stages developing internally.
Exposing infested wheat grains to cineole vapour, for example, would have added significantly to
the conclusions to be drawn from this paper. However, it is an omission that occurs in much of the
published work reviewed here.
Ahmed and Eapen (1986), for example, examined the effect of essential oil vapours against
adults of three insect pests: S. oryzae, another species whose larvae are internal feeders of cereals;
Callosobruchus chinensis (L.) (Bruchidae: Coleoptera), a pest of small grain legumes whose larvae
also develop internally; and Stegobium paniceum (L.) (Anobiidae: Coleoptera), a pest whose larvae
browse loosely in flour. Fifty young unsexed adults were exposed in desiccators to strips of filter
paper impregnated with eucalyptus oil, cineole or one of a selection of ten other essential oils.
Both eucalyptus oil and cineole were deemed to give good control of all three species of insect,
though they were more effective against the bruchid than against the cereal feeders.
A laboratory study of the persistent toxicity of four plant oils towards storage pests of wheat
(Thakur and Sankhyan 1992) showed that at the highest dose tested neem oil was longer lasting
in its toxicity towards R. dominica than eucalyptus oil (distilled from E. citriodora) but that at
lower doses eucalyptus oil performed best. However, against Oryzaephilus surinamensis (L.)
(Silvanidae: Coleoptera) and Tribolium confusum J. du Val (Tenebrionidae: Coleoptera) eucalyptus
oil gave the best protection at all doses. Treatment involved exposure of 07 day old insects to
three replicates of grain coated with oil at three concentrations (0.5, 1.0 and 1.5 per cent v/w).
Mortality was monitored over a period of sixteen weeks. Partial results for the two oils are shown
in Table 14.5.
The effect of oil vapours on the moth pest of cereals, Corcyra cephalonica (Stainton) (Pyralidae:
Lepidoptera), was determined by Pathak and Krishna (1991). Pairs of either newly emerged lar-
vae or those which were fifteen days old were exposed in small glass containers on a food
medium of sorghum and yeast to eucalyptus oil placed in small glass vials in the same enclosure.
Table 14.5 Comparative effectiveness of Eucalyptus citriodora and neem oils against Rhyzopertha dominica,
Oryzaephilus surinamensis and Tribolium confusum (after Thakur and Sankhyan 1992)
Dose Mortality (%) after time (weeks)

(ml/kg)
E. citriodora Neem
2 4 6 8 2 4 6 8
R. dominica 5 96.67 86.67 31.67 11.67 13.33 4.59 0 0

10 100.00 100.00 44.33 25.00 76.67 70.00 61.67 50.00
15 100.00 100.00 58.33 36.67 100.00 100.00 100.00 100.00
O. surinamensis 5 85.00 65.00 28.33 3.33 0 0 0 0
10 100.00 100.00 38.33 11.67 11.67 3.33 0 0
15 100.00 100.00 85.00 21.67 16.67 13.33 5.00 0
T. confusum 5 1.67 0 0 0 0 0 0 0
10 16.67 11.67 0 0 1.67 0 0 0
15 73.33 58.33 10.00 0 6.67 1.67 0 0

Adult moths were similarly exposed. The exposure of newly emerged larvae led to a reduction in
the numbers developing through to adults and to an increase in the development time for males
from thirty days for controls to fifty-six days and for females from thirty-three to sixty-two days.
Exposure of older larvae prevented all adult emergence. It was postulated that the effects were
more marked on the older larvae because these were much more exposed, moving across or close
to the surface of the food substrate, whereas younger larvae were buried more deeply and did not
come into contact with the volatiles as readily. Furthermore, the vapour had a marked effect on
the reproductive potential because oviposition by the emergent adults of exposed larvae was sig-
nificantly reduced. Exposure of adults directly to sub-lethal doses did not produce the same effects
on oviposition. Neem oil, which was also included in the experiments, did not produce any detri-
mental effects on the pest. Further work has elaborated on these findings (Pathak et al. 1993).
Sarac and Tunc (1995a) examined the effects of eucalyptus oil vapour against another moth
pest, Ephestia kuhniella Zeller (Pyralidae: Lepidoptera). Adults and last instar larvae, as well as
23 week old adults of T. confusum and S. oryzae, were exposed to one of four essential oils,
including that from Eucalyptus camaldulensis. Individuals in glass containers were exposed to the
vapours from filter papers treated with the oils. E. camaldulensis was very effective against
Ephestia kuhniella larvae and S. oryzae adults, causing 90 and 95 per cent mortality, respectively,
at 135 (g/l after five days exposure. It was less effective against T. confusum, the same dosage only
causing 85 per cent mortality after seven days. E. camaldulensis oil was generally less effective
than that from anis, Pimpinella anisum, but more effective than those from thyme species,
Thymbra spicata var. spicata and Satureja thymbra.
When the same oils were impregnated into filter papers with which the insects had direct
contact the effect on mortality of T. confusum and S. oryzae was not as marked (Sarac and Tunc
1995b): E. camaldulensis only caused 30 per cent mortality of T. confusum after five days exposure
(Ephestia kuhniella was not tested). However, E. camaldulensis oil was a very effective repellent
when the adults were presented with a choice of either treated or untreated grain. After 24 h,
74 per cent of the adults settled in the control wheat and only 17 per cent in grain treated with a
dosage of 0.25 (l/g oil. As the concentration increased to 1.0 (l/g still fewer adults were attracted
(5 per cent). This repellent effect declined as the oil volatilised but, even after four weeks, 50 per cent
of the activity was retained. In this respect E. camaldulensis oil was better than the others. It is
clear from this work that E. camaldulensis oil does have potential for use as an insect repellent in
stores, though whether this use would be cost-effective remains to be investigated.
The contact effect of eucalyptus leaves mixed with grain has also been observed with other
Sitophilus species. Sharaby (1988) admixed shade-dried, powdered leaves of E. globulus with rice
grains at 125 per cent concentrations in small petri dishes and exposed the samples to 13 day
old adults of S. oryzae and the temperate species S. granarius (L.) (Curculionidae: Coleoptera).
He found that the leaves of another Myrtaceae species, Psidium guajava (guava), were more toxic
to the insects than E. globulus but the latter did have an effect. Both plants were more toxic
to S. oryzae than S. granarius. However, in a repellency choice test E. globulus was more effective
than P. guajava: during the course of a week there were never more than 15 per cent of individu-
als located on the treated grain compared with 6080 per cent on untreated grain. Furthermore,
a sub-lethal dosage of leaf powder of either plant of 15 g/100 g of rice prevented emergence
of progeny of both species. Sharaby concluded that E. globulus does have potential as a rice
protectant.
Sasaki and Calafiori (1987) assessed the effects of dried eucalyptus leaves against S. zeamais.
They compared application of half a leaf of eucalyptus mixed in 150 g maize with treatments
with garlic. Unfortunately, the species of Eucalyptus used was not stated but it was found to
provide some degree of protection.

Leaf oils from E. citriodora and E. tereticornis have been tested in the laboratory against
S. oryzae and found to be relatively ineffective (see later, Table 14.6) (Gakuru and Foua-Bi 1995).
On the other hand, E. citriodora appeared to show rather more promise when extracts of the
leaves were tested. Gakuru and Foua-Bi (1996) coated samples of maize seed with petroleum
ether extracts at concentrations of 0.21.0 per cent (w/w). The mortality of twenty adults was
recorded daily for a week. Although E. citriodora was not as effective as four other plant species
(Ocimum basilicum, Capsicum fructescens, Piper guineense and Tetrapleura tetraptera) it nevertheless
gave considerable protection, especially at 1 per cent concentrations (100 per cent mortality was
attained after one week) when compared with untreated controls.
A similar experiment was conducted by Singh et al. (1996a,b) who exposed 15 day old
adult pairs of R. dominica to wheat mixed with powdered E. hybrida ("Eucalyptus hybrid,
i.e. E. tereticornis) leaves at 1.03.0 per cent (w/w) concentrations. Grain was left in open test
tubes for intervals of twenty days and samples were then examined for damage and adult mor-
tality. There were indications that the eucalyptus treatment did provide some degree of protec-
tion though the insect mortality data are difficult to interpret and the damage levels found in
controls were relatively low (11 per cent after sixty days). Other plants were tested in the study
and extracts of asafoetida (Ferula asafoetida), neem and Lantana camara were all more effective
than eucalyptus.
The control of R. dominica and the moth Sitotroga cerealella (Olivier) (Gelechiidae:
Lepidoptera) infesting paddy was investigated by Dakshinamurthy (1988) who treated grain
with powdered leaves of E. tereticornis. Control of this moth is of particular interest to farmers in
the developing world as it inflicts its damage on small-scale farm stores and is not found in
large, central stores. However, samples in the study were still only of laboratory size, 100 g for
S. cerealella experiments and 2 kg for those with R. dominica. Treatments were left for four
months, after which time damage due to the beetles was assessed and the total number of adult
moths counted. E. tereticornis provided significant control of both species. In the case of
R. dominica, only 3 per cent damage was found in treated samples compared with 13 per cent in
controls (and 9 per cent in samples treated with neem leaf ), while for S. cerealella 369 adults
emerged from untreated paddy but only seventy-seven in treated samples. In addition to euca-
lyptus and neem, three other plants were tested Vitex negundo, Pongamia glabra and Ipomea
tuberosa but E. tereticornis was the most effective of all of them. Although the experiments were
replicated four times none of the statistical data were presented so it is not possible to take into
account replicate variability.
Effects on insect pests of grain legumes

In store, pulses are attacked by a number of different pests of the Bruchidae family. Small grain
pulses, such as cowpea, grams, pigeon pea, chickpea and bambara groundnuts are attacked by
species of the genus Callosobruchus. The major pest of larger pulses, such as Phaseolus vulgaris
(common or kidney beans), is Acanthoscelides obtectus. Experiments to assess the effects of eucalyp-
tus on these pests have been conducted by several groups of workers.
Pajni and Gill (1991) subjected C. maculatus adults to volatiles of eucalyptus oils distilled
from E. citriodora (83 per cent citronellal) and E. globulus (91 per cent 1,8-cineole). Asarone, a
constituent of Acorus calamus rhizomes, known for its insecticidal properties, and some asarone
derivatives, were also tested. Both oils were found to be twice as effective fumigants as asarone.
Ahmed and Eapen (1986) examined the vapour effects of cineole and eucalyptus oils against a
related species, C. chinensis. They found that the vapours gave very effective control of this pest,
which was more susceptible than the cereal pests tested (noted earlier).

Although the results of testing E. citriodora and E. tereticornis oils against S. oryzae (Gakuru
and Foua-Bi 1995), referred to earlier, were disappointing, tests against C. maculatus were more
encouraging (Table 14.6). Experiments were conducted using petri dishes containing filter
paper impregnated with different quantities of essential oil and cowpea as nutritive support. Of
four essential oils tested, E. citriodora oil was the most effective, followed closely by Ocimum
basilicum. Oils from E. tereticornis and Citrus sinensis were relatively ineffective.
The same researchers (Gakuru and Foua-Bi 1996) confirmed the promise of E. citriodora in
tests involving extracts of nine plants. They obtained good control of C. maculatus when two-day-
old adults were exposed to cowpeas treated with 0.21.0 per cent extracts of E. citriodora. The low
dosages did not provide very effective control during the seven-day exposure period but the 1 per
cent treatment resulted in 80 per cent control within three days and 90 per cent after four days.
The effects of the volatiles of commercially available eucalyptus oil on A. obtectus were
assessed in well-designed and replicated experiments by Stamopoulos (1991). In a choice test
with individual females, using kidney beans which were either placed in the same arena by
themselves or with a vapour diffuser, replicated twenty-seven times, only 3 per cent of the eggs
were deposited on beans where the volatiles were present and 97 per cent on the control group.
Females moved towards the control seeds within a few minutes of exploration and remained
there for six days. In a no-choice test, egg production was significantly reduced by the presence
of eucalyptus oil vapour, as was egg hatchability. Three other essential oils were tested (gera-
nium, cypress and bitter almond) but eucalyptus oil was the most effective. Clearly, the repellent
effect of eucalyptus oil volatiles against A. obtectus can be exploited as a space treatment to pro-
tect beans during storage.
Faroni et al. (1995) compared the efficacy of mixing leaves of E. citriodora and black beans
with admixture of ash, sand, black pepper, termite mound soil and synthetic chemicals (includ-
ing deltamethrin) as protectants against A. obtectus infestation. Termite soil and black pepper
controlled damage for up to eight months of storage whereas the leaves of E. citriodora were only
effective in restricting the build-up of insect numbers for twelve weeks.
In southern France, A. obtectus is a significant pest of stored P. vulgaris. Regnault-Roger and
Hamraoui (1993) compared the mortality and fecundity of pairs of adults placed in petri dishes
with a small quantity of one of eleven different dried plant materials, generally leaves, and six
kidney beans. After twelve days E. globulus caused approximately 20 per cent mortality but was
not as effective as the most potent plant, Origanum serpyllum, which caused 50 per cent mortality.
However, E. globulus did have a significant effect on oviposition (19.1 ! 8 eggs compared with
Table 14.6 Effectiveness of Eucalyptus citriodora and E. tereticornis leaf oils against Callosobruchus maculatus
and Sitophilus oryzae (after Gakuru and Foua-Bi 1995)
Dose Cumulative mortality (%) after time (days)

(ml)
E. citriodora E. tereticornis
1 2 7 1 2 7
C. maculatus 0.5 2.50 6.49 10.65 3.75 3.89 13.49

1.0 15.00 20.78 31.50 1.25 2.60 31.50
2.0 91.25 91.25 100.00 3.75 8.75 18.15
S. oryzae 0.5 2.50 3.95 3.95 0 2.63 2.63
1.0 0 2.60 5.63 0 2.60 5.63
2.0 6.25 9.61 9.61 2.50 6.49 8.57

42 ! 12 for the control). The medium potency of E. globulus was confirmed by experiments in
which adult A. obtectus were exposed to essential oils freshly distilled from twenty-two different
plants (Regnault-Roger et al. 1993). Fifteen of the oils caused greater mortality than E. globulus
oil. The most potent group included Thymus serpyllum and Origanum majorana.
Unlike some other published reports, Regnault-Roger and her co-workers give proper
attention to the fact that the effects of essential oils on insects depend upon several things,
including, most importantly, their chemical composition. They go on to point out that the com-
position can vary depending on whether or not there exist chemotypes of the plant in question,
the season in which the plant is harvested, the part of the plant which is studied and the condi-
tions used for distillation or extraction. Although bioassay work is necessarily the main element
of research, the composition of the oil or extract being tested should also be determined and
not relegated to incidental importance as has often been the case in published reports to date. All
the oils used in the authors work were analysed and the results presented. E. globulus oil had a
cineole (&)-phellandrene) content of 86 per cent.
It would appear that although dried leaves of eucalyptus have an effect on A. obtectus
mortality and development the volatile components are much more effective.
Effects on mites
Mites are found associated with many foodstuffs and can be responsible for deterioration both of
raw flour and processed material such as dairy and meat products. Several workers have
attempted to develop methods using non-chemical techniques, including the use of eucalyptus
leaves, to control these pests.
Tyrophagus putrescentiae (Schrank) (Acarina: Acaridae) is a cosmopolitan pest of several stored
products and is encountered infesting stored grain and flour. Gulati and Mathur (1995) added
five pairs of adults to samples of wheat flour to which had been added 575 per cent (w/w) pow-
dered eucalyptus leaves (species not specified). Progeny production was observed at the end of
the fifteen-day life cycle. There was an approximately linear relationship between dosage and the
number of living progeny but even the lowest concentration of 5 per cent gave about 50 per cent
control in comparison with untreated flour (Table 14.7). However, when leaf powder was
applied at 5 per cent to wheat grain or wheat flour there did not appear to be any effect on either
egg hatch or adult emergence.
Perrucci (1995) investigated the control of a related species of mite, T. longior (Gervais)
(Acarina: Acaridae), a common pest of cured ham, cheese and similar products. The effects of a
commercial sample of E. globulus oil and its main terpene constituent, 1,8-cineole, were com-
pared with those of lavender and peppermint oils and their principal constituents. Acaricidal
Table 14.7 Effect of powdered Eucalyptus leaves on egg production and other life stages
of Tyrophagus putrescentiae in wheat flour (from Gulati and Mathur 1995)
Treatment Living progeny

(% Eucalyptus, w/w)
Egg Larvae Nymph Adult
75 2.33 0.86 1.02 5.83
50 4.66 1.66 1.83 14.49
25 8.16 1.99 2.16 25.83
10 42.99 6.16 11.33 61.99
5 51.66 9.99 15.99 69.83
0 98.16 14.66 20.66 78.16

activity was measured in petri dishes by (a) direct contact with the uniformly dispersed oil at
0.256.0 (l doses and (b) inhalation of vapour over a 24 h period. E. globulus oil (analysed and
shown to contain 76 per cent 1,8-cineole) was not as effective as the other plant oils and at the
highest dosage it resulted in 92 per cent mortality when applied by direct contact (cf. 100 per cent
mortality for the other oils at 1.0 (l) and 77 per cent mortality by inhalation. Similarly, 1,8-
cineole was much less effective (82 per cent mortality at 6.0 (l by direct contact and 50 per cent
mortality by inhalation) than linalool, linalyl acetate, fenchone, menthol and menthone at the
same dosage. The author concludes that the absence of harmful residues from essential oils, and
the lack of any adverse effects on the stored food itself, warrant further research on the possible
use of plant oils for mite control in the food industry.
Miyazaki (1996) also observed the effects of various oil vapours, including that of E. citriodora,
on T. putrescentiae, as well as on Dermataphagoides farinae Hughes (Pyroglyphidae: Acaridae), a mite
commonly found in house dust. Single replicates of twelve adults were exposed to 5 (l of one
of a series of oils in a volatilisation chamber and numbers moving were recorded up to 72 h.
E. citriodora oil caused 100 per cent immobility of D. farinae within 4 h but was much less effective
against T. putrescentiae, causing a maximum of only 40 per cent immobility (obtained after 24 h).
Effects on insect pests of other stored products

The potato tuber moth, Phthorimaea operculella Zeller (Gelechiidae: Lepidoptera) is a widely dis-
tributed pest of solanaceous crops in the tropics and sub-tropics. Kroschel and Koch (1996) con-
ducted trials to control this pest using a variety of treatments including synthetic insecticides,
Bacillus thuringiensis, and several plants, including leaves of unspecified eucalypts. Potatoes were
laid on, or completely wrapped in, leaves and the degree of tuber infestation was noted.
Although the treatments were only replicated twice and were not subjected to statistical analy-
sis, there were clear indications that the leaves had a deterrent effect and that wrapping the
tubers in leaves created a barrier to infestation. Despite very much better protection being
obtained by applying B. thuringiensis or the pyrethroid insecticide, fenvalerate, wrapping tubers
in eucalyptus leaves could provide a simple, cheap method of preserving tubers during storage.
Conclusion
The work of Kroschel and Koch (1996) represents the only testing of Eucalyptus under simulated
practical conditions. Even this work lacks sufficient replication to allow firm conclusions to be
drawn. However, it is apparent from laboratory experimentation that this genus does have
potential for use in the protection of stored grain and other food products against insect pest
attack. In particular, the volatile constituents of the leaves have demonstrated their potential for
use in the vapour phase as short-term repellents. Repellency appears to be more strongly associ-
ated as a function of this plant than the ability to cause mortality directly. However, the effects
may well cause mating and developmental disruption and so reduce reproductive potential.
Although repellency is generally a short-term effect, it may last for many weeks when extracts
are applied directly to grain and so may be of benefit to farmers storing grain for several weeks
or months. However, in order to determine whether this is the case, and to assess the cost-
effectiveness of using eucalyptus treatments under other storage conditions, more testing under
practical storage conditions needs to be undertaken.
Given the diversity in composition of eucalyptus leaf oils it would also be advantageous to
examine a greater number of Eucalyptus species for insecticidal effects. So far only a handful of
species have been investigated.

Allelopathy in eucalyptus
Introduction
Since Molish (1937) defined the term allelopathy, many scientists have been concerned with the
exploration and exploitation of allelochemicals (Whittaker 1972, Muller and Chou 1972, Rice
1984, Putnam and Tang 1986, Harborne 1988, Inderjit et al. 1995). In the widest sense the
term allelopathy refers to the biochemical interactions which occur between plants and includes
both deleterious and advantageous interactions. Rice (1984) regards it as an all-embracing term
to cover most types of biochemical interactions, including those between higher plants and
microorganisms. Typically, allelopathic inhibition results from a combination of allelochemicals
which interfere with several physiological processes in the receiving plant or microorganism.
Allelopathy has the potential to enhance crop production and lead to the development of a
more sustainable agriculture, including weed and pest control, through crop rotation, residue
management and a variety of approaches in biocontrol (Einhellig 1995). Trees of the genus
Eucalyptus are frequently surrounded by a grass-free zone and this has led to a search for possible
allelochemicals in Eucalyptus species. The results to date indicate that eucalypts may well be a
practical, commercial source of such chemicals in the future. In its simplest form this might
entail use of the powdered leaves as a natural herbicide. Alternatively, and with a greater under-
standing of their mode of action, the allelochemicals themselves or suitable derivatives could be
used as selective herbicides.
On the other hand, allelopathic effects may incline towards less use of certain eucalypts in
agroforestry schemes. On the basis of reduced germination of some Ethiopian crops in experi-
ments with aqueous leaf extracts, Lisanework and Michelsen (1993) suggested that planting of
E. camaldulensis in integrated land use systems should be minimised while E. globulus had less of
a potentially detrimental effect.
Allelochemicals in E. citriodora
Eucalyptus citriodora (lemon-scented gum) is often surrounded by bare, grass-free ground and it
seems likely that secondary metabolites are exuded from both fresh and fallen leaves which
inhibit the growth and seed germination of surrounding plants. In the course of research on
Eucalyptus metabolites which exhibit biological activities, the authors have studied the allelo-
chemicals from E. citriodora leaves.
Extraction of the leaves with 70 per cent aqueous acetone, followed by column chromato-
graphy in which the inhibitory activity of fractions was monitored against germinating seeds
and seedlings of lettuce (Lactuca sativa cv. Wayahead), garden cress (Lepidium sativum L.), green
foxtail (Setaria viridis L.) and barnyard grass (Panicum crus-galli L.) furnished two crystalline
inhibitors. These were subsequently identified as the (!)-p-menthane-3,8-cis- and trans-diols
shown in Figure 14.1 (Nishimura et al. 1982, 1984).
Both diols, as well as citronellal and citronellol, were determined quantitatively in the
leaves of growing E. citriodora by gas chromatography and gas chromatography combined with
mass spectrometry. The variation in concentration of the constituents in the seedlings with onto-
genetic age is shown in Figure 14.2. The diols were absent from juvenile tissue until thirteen
months (approximately fifty nodes) when they then increased to 4.5 mg/g (cis-diols) and
2.2 mg/g (trans-diols) in fresh adult leaves (twenty-one months old). Interestingly, both
diols occur as racemates. Levels of (!)-citronellal, on the other hand, the major constituent of
E. citriodora essential oils, gradually increased at first but after thirteen months decreased

1.2
Concentration in leaves (% w/w, fresh weight basis)
1.0 Oil content
OH
OH
0.5 Citronellal
OH
OH
Citronellol
0
16 24 32 40 48 70 90 110
Growth stage (nodes)
12 15 18 21
Growth stage (months)
Figure 14.2 Variation in oil content and concentration of the allelochemicals p-menthane-3,8-cis- and
trans-diol and other constituents in E. citriodora with ontogenetic age.
dramatically. This suggests that the cis- and trans-diols are formed biogenetically by cyclisation
of citronellal. However, it is not clear whether they are produced enzymatically. The diols were
not artifacts since the pH of the homogenised tissues was neutral (Nishimura et al. 1984).
In order to evaluate the allelopathic effect, samples of soil were collected at an E. citriodora
grove. Extracts of the soil were analysed and shown to contain cis and trans p-menthane-3,
8-diols, but in much lower amounts than in E. citriodora leaves: approximately 15 ppm compared
to about 4600 ppm in the leaves. The low concentration of the diols in the soil suggests either
that their extraction was inefficient and/or that they were partially transformed by microorgan-
isms in the soil.
The chiral compounds, (&)-cis, (#)-cis, (&)-trans and (#)-trans, were prepared to compare
their germination and growth inhibitory activities against lettuce seeds and seedlings, respec-
tively. The biological activity of racemic (natural product) and chiral compounds of the cis isomers
was found to be much higher than that of the trans isomers. Furthermore, the synthetic (&)-cis
isomer had a higher inhibitory activity than the optical antipode, suggesting that a receptor site
involved in the germination and growth of lettuce is also chiral (Nishimura et al. 1982).
The inhibitory activities of p-menthane-3,8-cis-diol against seed germination of several plants
are shown in Figure 14.3 (Nishimura et al. 1984). Concentrations of 100300 ppm
(5.8 % 10#4#1.7 % 10#3 M) inhibited seed germination in lettuce, garden cress, green foxtail
and barnyard grass. However, even at high concentrations (300 ppm) the diol had very little
inhibitory effect on the germination of E. citriodora itself or of rice. The patterns of inhibition of
hypocotyl growth of seedlings of the same plants were similar to those of seed germination: very
little inhibitory effect on E. citriodora and rice but significant inhibition of the other plants at
100300 ppm (green foxtail experiencing the greatest inhibition and garden cress the least). In

100
90
80
70
Inhibition (%)
60
50
40
30
20
10
0 10 30 100 300
Concentration (ppm)
Figure 14.3 Germination inhibition of p-menthane-3,8-cis-diol against seeds of some higher plants.
Experimental error is within 7 per cent. Symbols: ! lettuce, + garden cress, " green
foxtail, # barnyard grass, $ rice, E. citriodora.
terms of its use as a potential herbicide, it is interesting that the biological activity of the cis diol
is very selective against higher plants.
Studies by other workers have further demonstrated the inhibitory effects of E. citriodora
(e.g. Kohli et al. 1988, 1998, Singh et al. 1991). Particularly encouraging results have
been obtained in India in tests to combat the noxious weed Parthenium hysterophorus (Kohli
et al. 1998). The oil from E. citriodora was more effective in causing injury to the weed than
E. globulus oil.
Allelochemicals in other Eucalyptus species

Of the other eucalypts studied, E. camaldulensis has attracted much attention. Del Moral and
Muller (1970) investigated allelochemicals in E. camaldulensis which is surrounded by bare
ground and identified 1,8-cineole, *- and )-pinene, and *-phellandrene as volatile inhibitors.
This role for the terpenes was established from observations of their presence in all the various
phases of the interaction. Thus:
1 Terpenes are present in significant quantities in the leaves of E. camaldulensis.

2 They are constantly turned over by the eucalypt and a vapour cloud of volatile essence hangs
around the plants.
3 They occur in the soil surrounding the plants.
4 They remain in the dry soil until rains activate soil microorganisms which degrade them.
5 They can be transported into plant cells through the waxy coatings of seeds or roots.
6 They have a significant effect on the germination of seeds of those annuals which grow in the
adjacent grassland area.

The presence of other possible allelochemicals in E. camaldulensis has been investigated by
Nishimura (1989). Fractionation of acetone extracts of leaves, with monitoring of growth
inhibitory activity, resulted in the isolation of spathulenol (Figure 14.4).
The leaves of E. viminalis, E. delegatensis and E. pauciflora, which form colonies in nature, have
also been found to contain potent allelochemicals, mostly terpenoids and phenolics (Figure 14.4)
(Nishimura unpubl.).
H
E. camaldulensis
Spathulenol
H
OH COOH
OH
E. viminalis
COOH
O
COOH
OH
D--Phenyllactic acid 2-Furoic acid p-Coumaric acid
OH OH
E. delegatensis OH
OH
cis trans Thymol Carvacrol

p-Menth-2-en-1-ol
E. pauciflora
H OH
4-Phenylbutan-2-one -Eudesmol
H OH OH
-Eudesmol -Eudesmol
Figure 14.4 Examples of potent allelochemicals from four Eucalyptus species.

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15 Chemical ecology of herbivory
in eucalyptus
Interactions between insect and mammalian
herbivores and plant essential oils
Ivan R. Lawler and William J. Foley
Introduction
Eucalyptus dominates more than 90 per cent of Australian forests and woodlands and supports a
wide range of endemic vertebrates and invertebrates. Nonetheless, few insects, and even fewer
mammals, eat the foliage to any appreciable extent (Landsberg and Cork 1997). Eucalyptus
foliage contains low amounts of dietary nitrogen, which is essential for the maintenance and
reproduction of all animals (Cork and Foley 1991), but also appreciable amounts of essential oils
and phenolic compounds. Both these groups of compounds are believed to have a significant
influence on the acceptability of foliage as food and the nutritional quality of that foliage (Hume
1982).
There has long been speculation about the degree and nature of the influence of Eucalyptus oils
on the food choice of herbivores. This interest has been driven by a number of considerations.
Firstly, the restricted diet of koalas suggests that a knowledge of its nutrition and food choices
will contribute substantially to its conservation and the conservation of other sympatric species
(Cork and Sanson 1990).
Secondly, efforts to establish plantations of Eucalyptus for wood fibre and sawn timber are
plagued by the damage inflicted on plants by pest insects and mammals (Montague 1994,
Patterson et al. 1996). Although this is countered by extensive poisoning campaigns, current
research is seeking to incorporate naturally resistant genotypes into plantation management sys-
tems (Farrow 1993). Determining the role of essential oils and related compounds in conferring
resistance to herbivores has substantial economic consequences.
Finally, the dominance of Eucalyptus in the Australian environment, a variable level of her-
bivory and the substantial quantities of plant secondary metabolites contained in the foliage, has
spurred a number of studies seeking a more fundamental understanding of the evolutionary
interactions between plants and herbivores (Morrow and Fox 1980, Morrow et al. 1976, Cork
and Foley 1991). For example, Morrow and Fox (1980) used Eucalyptus and its volatile oils to test
whether herbivory was controlled by the metabolic costs of detoxification. These types of studies
have made important contributions to broader ecological theory.
In this chapter, we review studies which have examined the role of Eucalyptus oils in deter-
mining the feeding of Australian insects and mammals or which have measured the conse-
quences of ingested oils. We conclude by evaluating the role of essential oils in conferring
natural herbivore resistance on Eucalyptus and the prospects of selecting high yielding genotypes
for use in breeding programmes.

Components of eucalyptus oils relevant to herbivores
Previous chapters have reviewed the nature of eucalyptus oils and discussed the diversity of
mono- and sesquiterpenes present in different species. Several different techniques have been
used to extract eucalyptus oils from plants eaten by herbivores, but most studies have used steam
distillation. However, steam distillation can volatilise compounds other than essential oils and
may also lead to some rearrangements or hydrolysis of naturally occurring compounds. Since
some of these non-terpene compounds are involved in significant ecological interactions, we
review their nature and effects below.
Benzaldehyde
Benzaldehyde (Figure 15.1a) almost certainly arises from the hydrolysis of cyanogenic glycosides
in leaf tissue and in some species (e.g. E. yarraensis, Boland et al. 1991), can dominate the steam-
volatile extractives. The only cyanogenic glycoside that has been isolated from Eucalyptus
is prunasin (Figure 15.1b) (Finnemore et al. 1935, Pass et al. 1998, E.E. Conn pers. comm.).
Concentrations in the young expanding tips of E. cladocalyx can exceed 10 mg/g dry mass
(Gleadow et al. 1998). Sheep have been reported to be poisoned after eating E. cladocalyx foliage
(Everist 1981) and koalas after eating E. viminalis foliage, but in neither case has the link with
cyanogens been proven (Southwell 1978).
Of potentially more importance ecologically is the observation that many eucalypts are poly-
morphic for prunasin. These include E. viminalis, E. orgadophila, E. ovata and E. polyanthemos.
This provides a powerful tool for investigating fundamental questions of the cost of maintaining
plant secondary metabolites and may provide explanations of variable herbivore behaviour
(R. Gleadow and I. Woodrow pers. comm.).
Acylphloroglucinols
Eucalyptus and several other genera of the Myrtaceae contain fully substituted acylphlorogluci-
nols, some of which are steam volatile and frequently isolated during phytochemical investiga-
tions aimed principally at the volatile essential oils (Boland et al. 1991, Ghisalberti 1996). The
most widespread compound is torquatone (Figure 15.1c) (Bowyer and Jeffries 1959) which can
comprise up to 40 per cent of the steam-volatile constituents of E. torquata (Bignell et al. 1994).
A range of other compounds varying in the level of oxidation of the nuclear carbons has been
described including jensenone (Figure 15.1d), which dominates the steam-volatile extract of
E. jensenii leaf (Boland et al. 1991, 1992). These compounds, together with the acylphloroglucinol-
terpene adducts described below, can have substantial biological activity in a number of
different systems.
Acylphloroglucinolterpene adducts
In the past 1015 years a number of compounds have been identified which result from terpenes
bonded to fully substituted acylphloroglucinol derivatives (Chapter 12 this volume, Ghisalberti
1996, Pass et al. 1998). These are known as euglobals (e.g. euglobal III, Figure 15.1e) (Kozuka
et al. 1982a,b) and macrocarpals (e.g. macrocarpal G, Figure 15.1f ) (Yamakoshi et al. 1992).
None are steam volatile but, given that common essential oils form part of the structure, and
given their apparent importance in some ecological interactions (Pass et al. 1998, Lawler et al.
1998), some weight will be given to them in this chapter.

CHO HOH2C
O O
OH CN
HO
OH
(a) Benzaldehyde
(b) Prunasin
CH3 CHO
CH3O OCH3 HO OH
O O
H3C OHC
OCH3 OH
(c) Torquatone (d) Jensenone
CHO
CHO
HO OH
HO O
OHC OHC
OH
OH
(e) Euglobal III (f) Macrocarpal G
CHO
HO OH
CHO
HO O CHO
OH
OHC
OH
(g) Sideroxylonal A
Figure 15.1 Structures of some non-terpenoid compounds extracted from Eucalyptus leaves by conven-
tional steam distillation for essential oils and of possible antifeedant compounds with
similar structures.
Although there are undoubtedly more compounds to be discovered, those already known are
formed with only a restricted number of terpenes. The euglobals contain a monoterpene moiety
derived most commonly from !-pinene, although compounds with sabinene and !-phellandrene
have also been identified. A second group of euglobals are formed with sesquiterpenes, most
commonly bicyclogermacrene. Macrocarpals differ from euglobals in that they lack the ether
linkage between the aromatic and terpenoid parts of the structure. All terpene adducts of known
macrocarpals are derived from sesquiterpenes.

Dimeric acylphloroglucinols
A limited number of compounds have been described which can generically be termed dimers of
the simple acylphloroglucinols. These include sideroxylonal A (Figure 15.1g) and B, robustaol
A and grandinal. Of these, only the effect of sideroxylonals on insect and mammal feeding has
been investigated, with strong indications of high deterrency (see below).
Biosynthesis of acylphloroglucinol compounds

Little is known of the biosynthesis of the simple acylphloroglucinol structure itself. The euglob-
als and dimeric compounds are presumed to be formed by DielsAlder condensations but there
have been no formal synthetic studies to date (Ghisalberti 1996). The generation of a macro-
carpal is thought to involve a carbocationic species which acts as a cationic initiator in the cycli-
sation of the sesquiterpene precursors (Ghisalberti 1996). Acylphloroglucinols occur in all
subgenera of Eucalyptus (Eschler, Pass, Willis and Foley unpubl.).
Ecological factors affecting the concentration of oils in Eucalyptus foliage

The concentration of volatile essential oils in foliage may be influenced by a number of extrinsic
factors including soil type, light and atmospheric CO2. Knowing how essential oils and other
plant secondary metabolites respond to these factors is important because (a) we need to be able
to predict how climate change will affect animalplant interactions, and (b) several key theories
of animalplant interactions are couched in terms of the relationship between the level of
herbivory and the resources available to the plant.
Most influential of these theories are those of resource availability or carbon-nutrient balance
(Bryant et al. 1983, Coley et al. 1985). These propose that the concentration of carbon-based
plant secondary metabolites is governed by the availability of carbon to other nutrients. That
is, under conditions where carbon is plentiful relative to other nutrients (e.g. high light, low
soil nutrients) growth will be limited by these other nutrients, leaving the excess carbon
to be diverted to activities other than growth, such as carbon-based defences (Coley et al. 1985).
The few available data suggest that Eucalyptus phenolics behave in a manner consistent with
these theories but that the same is not true for essential oils. Lawler et al. (1997) grew seedlings
of E. tereticornis under conditions of varying carbon and nutrient supply and measured the con-
centration of steam-volatile essential oils in the foliage (Figure 15.2). The concentration of leaf
essential oils in E. tereticornis, and also in E. citriodora (Lawler, Foley and Woodrow unpubl.),
actually increased with high soil nutrients. Increased light also increased foliar essential oil
concentrations but only under high soil nutrient conditions (Lawler et al. 1997). Elevated atmos-
pheric CO2 had no effects on foliar essential oil concentration in E. tereticornis or E. citriodora but
Adamson and Woodrow (pers. comm.) found elevated foliar essential oils in E. nitens seedlings
grown under elevated CO2.
The oil content of seedlings differs both quantitatively and qualitatively from that of the
foliage of the mature plant (Chapter 4 this volume, Boland et al. 1982). For example, seedling
leaves of E. delegatensis contained only about 0.1 per cent (dry weight basis) of steam-volatile
essential oils, whereas mature foliage contains 1020 fold more oil (Boland et al. 1982). These
differences are significant because seedlings may often be more susceptible to herbivory than
adult plants. Attempts to select for, or breed, plants resistant to herbivores on the basis of their
foliar terpene concentrations may founder unless the relationship between the concentration of
essential oils and herbivory in seedling plants is considered. The differences between seedling

1.8
1.6
(%, dry matter basis) 1.4
Total essential oils
1.2
1.0
0.8
0.6
0.4
0.2
0.0
Low High Low High
light light light light
Low nutrient High nutrient
Figure 15.2 Effect of variation in soil nutrients, light and atmospheric CO2 on essential oil content of
Eucalyptus tereticornis leaves. Unshaded bars represent plants grown at ambient (350 ppm)
CO2 levels while shaded bars represent plants grown at elevated (800 ppm) CO2 levels
(after Lawler et al. 1997).
and adult plants are most probably a consequence of the low energy reserves contained in
seedlings, together with the relatively high metabolic cost of synthesis and maintenance of
essential oils (Gershenzon 1994), but this is an area that needs further research.
Diet choice in vertebrate herbivores

The vertebrate herbivores that eat Eucalyptus foliage extensively are all marsupials. These include
arboreal folivores such as koalas (Phascolarctos cinereus), greater gliders (Petauroides volans), com-
mon ringtail possums (Pseudocheirus peregrinus) and common brushtail possums (Trichosurus
vulpecula), and some macropodines (kangaroo family) such as the swamp wallaby (Wallabia
bicolor), the Tasmanian pademelon (Thylogale billardieri) and the red-necked wallaby (Macropus
rufogriseus). Although kangaroos can inflict severe damage on Eucalyptus plantations (Montague
1994), there are no data examining their interactions with Eucalyptus. In contrast, the reliance of
koalas and the other arboreal folivores on Eucalyptus foliage, and in particular that of a restricted
subset of species, has led to many studies of the relationship between the volatile oil content of
the foliage and food choice. The rationale for these studies has ranged from the distinctive
odours of the oils, to their alleged thermogenic properties and their potential germicidal effects
on the microflora of the gut (Pratt 1937, Fleay 1937).
However, to date there has been no convincing or conclusive evidence that simple essential oils
play any role in diet selection by koalas or any other marsupial herbivore. For example, Southwell
(1978) could find no association between the level of defoliation of individual Eucalyptus trees and
their concentration of the total steam-volatile oils or the proportion of 1,8-cineole in these oils.
Betts (1978) claimed that the ratio of cineole to sesquiterpenes in E. rudis was an important
determinant of food choice in koalas eating that species but his data explained only 18 per cent
of the observed variation. Furthermore, there was no explanation as to why this fraction or ratio
should be more or less important than any other component. Pratt (1937) argued that cineole
had a thermogenic effect, whereas "-phellandrene exerted a cooling effect on the animals which

ate the compound, and that these effects correlated with food choice in koalas in different loca-
tions. Neither the supposed thermogenic effects nor the alleged pattern of food choice has stood
up to closer examination (Southwell 1978).
Hume and Esson (1993) argued that koalas required a minimum threshold of oil in the diet
but there was no clear correlation between the total steam-volatile concentrations and the rela-
tive feeding effort by koalas. In this case, feeding effort was allocated to one of four categories but
animals always had some favoured foliage available. Zoidis and Markowitz (1992) found no
correlation between the concentration of cineole in foliage and food intake by koalas in the San
Diego Zoo. In contrast to the study of Hume and Esson (1993), Lawler et al. (1998) compared
koala feeding on different individual trees of E. ovata and E. viminalis and found that intakes of
foliage were higher when the essential oil content was significantly lower than Hume and Essons
suggested threshold. For individual trees within each Eucalyptus species, intakes decreased in a
manner strongly consistent with the total essential oil concentration (Figure 15.3). A similar
pattern was also observed for common ringtail possums feeding on the same trees (Figure 15.4a).
Although these correlative approaches appear to be a reasonable way to test the basis of food
choice in mammals, they are unlikely to succeed where the essential oil profile of the foliage is
complex, as in Eucalyptus. This is because we have to decide a priori what dietary components are
important, and simply because a foliage smells strongly to man does not mean that it smells the
same way to an animal. In addition, what is toxic to man may not be toxic to a particular herbi-
vore. For example, black colobus monkeys (Colobus satanus) can eat large quantities of toxic
alkaloid-rich leaves which would be fatal to non-adapted species (McKey et al. 1981). Similarly,
while we have shown above that ingestion of Eucalyptus leaves correlates strongly with the essen-
tial oil content of those leaves, for their body sizes, the marsupial folivores of Eucalyptus can eat
over ten times the amount of essential oils known to cause fatality in humans (McLean and Foley
1997), and can do this for sustained periods (Lawler unpubl.). Correlative evidence does
not imply any causal link; a correlation may arise simply because the concentration of oils is
correlated with the true limiting factor.
Most studies of the role of essential oils in regulating feeding in other vertebrate herbivores
have been similarly inconclusive (e.g. Duncan et al. 1994) or do little to demonstrate causal
60
50
Dry matter intake
(g . kg0.75 . d1)
40
30
20
10
0
0 1 2 3 4 5
(%, dry matter basis)
Figure 15.3 Relationship between food intake of koalas and essential oil content of leaves. Circles
represent Eucalyptus ovata and squares represent E. viminalis (after Lawler et al. 1998a).

(a) 60
50
Dry matter intake
(g . kg0.75 . d1) 40
30
20
10
0
0 1 2 3 4 5
(b) 35
30
Dry matter intake
25
(g . kg0.75 . d1)
20
15
10
0
0 3 6 9 12
Cineole concentration
Figure 15.4 Relationship between food intake of common ringtail possums and essential oil content
of: (a) leaves, (b) an artificial diet. In (a), circles represent Eucalyptus ovata and squares rep-
resent E. viminalis. Note that in leaf diets data are for total essential oils, while in the arti-
ficial diet cineole was used since in a range of species, including E. viminalis, it is the
predominant component of the oil (after Lawler et al. 1998a).
relationships. Clearly a better option is a bioassay involving the use of pure compounds added to
an artificial diet in isolation. In this way, other unknown differences between diets can be
excluded and cause and effect can be identified conclusively.
Bioassays with marsupials fed isolated essential oils

The few studies that have fed isolated eucalyptus oils to marsupial herbivores do not support the
notion that essential oils, in themselves, are important influences on diet selection. Pass et al.

(1998) isolated oils from both palatable and unpalatable forms of E. ovata. The main difference
was quantitative: unpalatable trees had higher total oil contents though the compositions of the
oils were similar, with cineole comprising about 80 per cent of the total extract. Although ani-
mals preferred not to feed on either the whole extract or cineole-treated food when given a
choice, there was no reduction in food intake when only cineole-treated food was offered. These
results are consistent with studies of Krockenberger (1988) in which he fed cineole to both com-
mon ringtail and common brushtail possums. No effect on food intake, total diet digestibility or
nitrogen metabolism was detected. M. Harvey and I.D. Hume (unpubl.) fed common brushtail
possums volatile monoterpenes and sesquiterpenes extracted from E. haemostoma leaves at
3.54.0 per cent (dry matter) levels in the diet but they, too, could detect no effect of these frac-
tions on food intake except when the animals were given a choice between oil-rich diets and the
basal diet alone.
The study by Lawler et al. (1998) mentioned earlier has presented perhaps the strongest evi-
dence of a negative correlation between food intake by marsupial folivores and the essential oil
content of the leaves. This was achieved by looking at the differences in intake of individual trees
within each Eucalyptus species. This reduced the interference of qualitative differences (i.e. dif-
ferences in the constituent compounds of the oil) with the quantitative differences (i.e. actual
amounts) in feeding between subject trees which may occur when several species are used.
However, the same study also refuted the role of essential oils as true toxins. Using no-choice
experiments they showed that the amounts of essential oil required to be added to an artificial
diet to reproduce the decrease in food intakes seen in leaves were much higher than those found
in leaves (Figure 15.4). Hence the bioassay showed that the essential oils were not the cause of
the effect, as may have been implied by the correlation. This is further emphasised by data which
show that both common ringtail possums and common brushtail possums can rapidly be condi-
tioned to eat diets containing greater than 12 per cent cineole (dry weight basis) (Lawler et al.
1999 see below, Boyle unpubl.).
Although the difference between two-choice and no-choice experiments suggests that there is
some metabolic cost involved in ingesting essential oils, this cost is either so small or dissociated
sufficiently from the ingestion process that it has no effect on food intake. Integrating the above
observations, a possible role for essential oils in diet choice of herbivores was suggested by
Lawler et al. (1998). There is a strong smell and taste associated with essential oils and food
intakes are strongly correlated with leaf essential oil levels. However, since they apparently do
not present an insurmountable challenge to the animals after ingestion, perhaps they are used by
the animals as a cue to the toxin levels of the leaves.
Lawler et al. (1999) tested whether the avoidance by animals of high essential oil diets could
be the result of a conditioned food aversion, that is, does the aversion result from the animals
learning to associate the sensory effects of the essential oils with the negative effects of another
compound also found in Eucalyptus leaves? An initial test was made on twelve ringtail possums
of reduction in food intake when cineole was added to the diet (again in a no-choice situation):
all possums were found to reduce food intake significantly (Figure 15.5a). Half the animals
(treatments) were then taught to eat cineole by increasing the amount of cineole in the diet
daily until it reached over 10 per cent of the dry weight of the diet after twelve days. The
remaining animals (controls) were fed only the basal diet over the same period. At the end of this
time they were again tested: those exposed to increasing cineole showed little reduction in
intakes, while the control group matched their previous levels (Figure 15.5b). The treatment
animals were then taught the aversion to cineole again by adding both cineole and jensenone (an
acylphloroglucinol derivative) in corresponding amounts to the diet so that the effects of the
jensenone would be associated with the smell and taste of the cineole. Finally, both groups were

(a) 40
35
30
Dry matter intake

(g . kg0.75 . d1)
25
20
15
10
0
Cineole Control
Diet offered
(b) 40
35
30
Dry matter intake
(g . kg0.75 . d1)
25
20
15
10
0
Cineole Control
Diet offered
(c) 40
35
30
Dry matter intake
(g . kg0.75 . d1)
25
20
15
10
0
Cineole Control
Diet offered
Figure 15.5 Evidence for a conditioned food aversion to cineole in common ringtail possums. Data
shown are food intakes by the same animals of an untreated diet and one to which cineole
was added. Data are for two groups of animals, one of which (treatment) was acclimated
to a high-cineole diet while the other (control) was fed only the untreated diet through-
out. Three stages of the experiment are represented: (a) initial test, (b) post acclimation,
(c) after reconditioning (see text for explanation). Unshaded bars represent treatment
animals and shaded bars represent control animals (after Lawler et al. 1998b).
tested again with only cineole added to the diet: the treatment group again behaved in a manner
not significantly different from the controls (Figure 15.5c). Lawler et al. (1999) also present
matching data for common brushtail possums fed cineole in artificial diets. It is clear from these
experiments that the avoidance of Eucalyptus essential oils by marsupial folivores can be the
result of a learned association with negative effects not caused by the essential oils themselves.
The value of essential oils as deterrents of these animals appears to lie in their strong, overriding
smell and taste, which is easily associated with negative effects.
Effects of ingested essential oils on vertebrate herbivores

Even if essential oils do not actually deter mammals from eating Eucalyptus foliage, they may
still impose a metabolic cost on the animal and lead to some disruption of metabolic and diges-
tive processes. The germicidal effects of many constituents of Eucalyptus foliage (Boland et al.
1991) have suggested to some workers the potential for deleterious interactions with intestinal
bacteria (Fleay 1937).
The marsupial herbivores that eat Eucalyptus foliage rely to a small extent on the digestion of
foliar cell walls in the hindgut for part of their energy intake, but the great majority of
digestible energy is derived from the constituents of the cells. For example, fermentation mea-
sured in vitro in the caecum and/or proximal colon of koalas (Cork and Hume 1983) and greater
gliders (Foley et al. 1987) contributed only about 10 per cent of both species digestible energy
intake. Nonetheless, if ingested essential oils disrupt this process by killing the caecal bacteria,
then the animal might find itself unable to digest an essential part of its diet. Early in vitro stud-
ies in deer by Nagy et al. (1964), Oh et al. (1968) and Connolly et al. (1980) showed that many
components of the oils of Douglas Fir significantly inhibited the growth and activity of rumen
microbes derived from sheep and deer in vitro.
It is difficult to sustain an analogous argument for marsupials, namely, that the microbial
populations of koalas, greater gliders, and ringtail and brushtail possums are all found in the
caecum and colon. Indeed, Foley et al. (1987) showed that most oils were absorbed in the simple
stomach and small intestine, thus avoiding for the most part interactions with microbes.
Eucalyptus essential oils could still have a deleterious effect in those species which house their
microbial population in the stomach (e.g. foregut fermenters such as goats and wallabies) but
the evidence from studies of similar essential oils in sheep and deer (Cluff et al. 1982, White
et al. 1982) suggests that the oils are again rapidly absorbed, or else volatilised and eructated
from the rumen very soon after they are ingested. There is little reason to suspect that the situa-
tion would be different with wallabies and Eucalyptus. Overall, the evidence suggests that
Eucalyptus essential oils have little direct effect on the digestive processes of animals that nor-
mally eat the foliage.
Metabolic transformations of Eucalyptus essential oils by mammals

Absorbing ingested oils from the gut avoids interactions with microbes but these materials must
still be detoxified and excreted, and doing so can be energetically expensive. Several authors
(Cork et al. 1983, Foley 1987) have argued that the poor conversion of digested energy from a
diet of Eucalyptus foliage into metabolisable energy is due, in part, to the excretion of oils and
their metabolites in the urine.
There have been a number of studies of the metabolic fate of ingested Eucalyptus oils in foliv-
orous marsupials. Part of the rationale for these studies has been a curiosity about the pathways
of degradation (e.g. Bull et al. 1993) but amongst ecologists the interest has been driven by the

notion that understanding the metabolites might help in measuring the cost of ingesting oil
components.
In koalas, brushtail possums and greater gliders 9598 per cent of volatile oils are absorbed
from the digestive tract. These oils are believed to be modified in the liver by oxidation or
hydrolysis, possibly conjugated with a small molecule, and then excreted via the urine or bile
(Hume 1982). Several recent studies have been reviewed by McLean and Foley (1997). The
outstanding trend in studies by McLean et al. (1993, 1995, 1997) is that mammals which are
capable of including Eucalyptus foliage in their diets appear to have developed a significantly
greater capacity to produce highly oxidised metabolites of ingested monoterpenes than have
other animals. These highly polar products can then be excreted in the urine without the need
for conjugation with glucuronic acid or glycine.
For example, McLean et al. (1995) studied the metabolic fate of dietary citronellal in greater
gliders and common ringtail possums. They found that this monoterpene was cyclised and oxi-
dised to trans-3,8-dihydroxy-p-menthane-7-carboxylic acid, in contrast to rabbits which do not
oxidise the cyclised product. McLean et al. (1997) examined the metabolism of p-cymene in rats,
common brushtail and ringtail possums, and greater gliders. They observed eleven urinary
metabolites and grouped these according to the number of oxygens added per molecule of
p-cymene. Rats excreted metabolites containing from one to four oxygens, whereas brushtails
excreted metabolites with two to four oxygens, and common ringtails and greater gliders only
excreted metabolites with three or four oxygens. This trend is also apparent when considering
metabolites of "- and !-pinene formed by common brushtails and koalas (Southwell et al.
1980). One advantage of excreting unconjugated products is that the loss of carbohydrates and
amino acids which are used as conjugates is avoided. This may be a significant advantage in the
case of nutrient-poor diets such as Eucalyptus foliage.
Recently, Carman and co-workers (Carman and Klika 1992, Bull et al. 1993, Carman and
Rayner 1996) made a detailed study of the fate of cineole in common brushtail possums.
Common brushtails produce a range of metabolites, principally 9-hydroxycineoles and cineole-
9-oic acids, as well as other alcohols and diols. Of particular interest is the chirality of the major
metabolites because females produce a higher ratio of S/R enantiomers than males. Carman and
Klika (1992) argue that these could be involved in pheromonal signalling. Clearly there remain
a number of exciting avenues to explore in our understanding of the metabolism of Eucalyptus
essential oils by folivorous marsupials.
Diet choice in insect grazers of Eucalyptus

Feeding by insect herbivores on Eucalyptus foliage is just as variable as feeding by vertebrate herbi-
vores. Several studies have identified marked interspecific (Morrow and Fox 1980), intraspecific
(e.g. Journet 1980, Edwards et al. 1993, Stone and Bacon 1994, Patterson et al. 1996) and even
intra-individual (Edwards et al. 1990) differences in the amount of defoliation. A review by
Ohmart and Edwards (1991) details the nature of the plantanimal interaction. They concluded
that plant secondary metabolites of Eucalyptus have very little effect on patterns and amounts of
insect herbivory and on the survival and performance of insect herbivores. However, since the time
of Ohmart and Edwards review, continuing studies have gathered strong correlative evidence to
suggest that insect herbivory is affected by foliar essential oils, in particular cineole (Edwards et al.
1993, Stone and Bacon 1994). We briefly review the accumulation of this evidence below.
Morrow and Fox (1980) were the first to suggest that there was an association between the
foliar essential oil content and the level of damage in two alpine eucalypts, E. stellulata and
E. pauciflora. However, their study of five Eucalyptus species showed that the distribution of

Table 15.1 Relationship between essential oil content of leaves and grazing damage by insect herbivores
of Eucalyptus (from Morrow and Fox 1980)
Species Essential oil content a p value of difference

Heavy grazing Light grazing
E. pauciflora 1.149 #0.150 1.253 # 0.253 nsb

E. bridgesiana 3.866 #0.423 3.214 # 0.363 ns
E. melliodora 4.223 #0.700 2.973 # 0.546 ns
E. viminalis 3.740 #0.658 6.864 #1.466 0.025 $p $ 0.05
E. dives 9.909 #0.870 13.389 # 1.512 0.013 $p $ 0.025
a % w/w, dry matter basis.

b Not significant.
damage, eggs and insects, as well as the feeding rates, growth and survival of insects, demon-
strated few consistent effects of total essential oil content (Table 15.1). The average oil yield of
the species used in the experiments ranged from 1.2 per cent to 11.6 per cent (dry matter basis)
with yields in some individual plants as high as 20 per cent. In E. dives and E. viminalis there was
an association between yield and damage. The plants that suffered low levels of damage had oil
yields significantly greater than those suffering high levels of damage. However, there was no
significant difference in total oil yields between the two levels of damage for the other three
species, E. pauciflora, E. bridgesiana and E. melliodora. In fact, there was a tendency toward lower
oil yields for lightly damaged trees in the latter two species. Morrow and Fox (1980) argued that
antiherbivore effects may only become apparent if a threshold in total oil concentration is
exceeded. However, it can be seen from Table 15.1 that the heavily grazed E. dives had more than
twice the total oil yield of the lightly grazed trees of E. pauciflora, E. bridgesiana and E. melliodora.
Recent studies by Edwards et al. (1993) and Stone and Bacon (1994) have shown a strong
negative association between insect herbivory and leaf essential oils, while another (Patterson
et al. 1996) has shown no relationship. Recent work has taken into account the composition of
the oils, whereas Morrow and Fox only considered the total oil yield. For example, Edwards et al.
(1993) found that the proportion of cineole in the leaf essential oil best explained differences in
levels of herbivory by Christmas beetles (Figure 15.6). Although Patterson et al. (1996) found no
effect of essential oils in E. regnans on herbivory by Chrysophtharta bimaculata, the concentration
of cineole in that species is very low. The authors also suggested that perhaps paropsine beetles
are less affected by Eucalyptus essential oils than are other insect herbivores. It should be noted
also that a high proportion of the E. camaldulensis trees examined by Edwards et al. (1993) had
both a high proportion of cineole in the leaves and a high level of defoliation by Anoplognathus, a
non-paropsine beetle (Figure 15.6c).
The above studies suffer from the same shortcomings as do those relating mammal feeding
preferences to leaf essential oils, namely, the studies are all correlative and do not show cause and
effect. If essential oils, including cineole, are to be conclusively shown to be deterrents to insect
feeding, then bioassays with a range of insect species need to be performed. To date we are not
aware of any studies in which either whole oil extract or isolated cineole have been fed to any
foliage-feeding insect. Previously it might have been argued that direct addition of cineole
would lead to an unnatural situation because the headspace vapour pressure would be excessive.
It has been shown that high vapour pressures of Eucalyptus essential oils are highly toxic to
insects (Sarac and Tunc 1995, J. Seymour pers. comm.). However, there are now a number of
methods available, such as microencapsulation (Clancy et al. 1992), that may overcome these
difficulties and make these sorts of experiments more feasible.

(a) 100
90
80
70
Defoliation (%)
60
50
40
30
20
10
0
0 10 20 30 40 50 60 70 80 90 100
Cineole content of oil (%)
(b) 100
90
80
70
Defoliation (%)
60
50
40
30
20
10
0
0 10 20 30 40 50 60 70 80 90 100
(c) 100
90
80
70
Defoliation (%)
60
50
40
30
20
10
0
0 10 20 30 40 50 60 70 80 90 100
Figure 15.6 Relationship between tree defoliation by insects and proportion of cineole in the essential oil
of the leaves of three Eucalyptus species: (a) E. melliodora, (b) E. sideroxylon, (c) E. camaldulensis
(after Edwards et al. 1993).

It may be that cineole is only effective in synergy with other oil components or it may serve as
a cue to the presence of some other toxic molecules. Cineole is clearly metabolised by some of the
major insect herbivores of Eucalyptus (see below). However, it remains to be seen whether this
need to metabolise cineole is limiting the ability of insects to ingest cineole-rich diets, as appears
now not to be the case for marsupial folivores of Eucalyptus (see above).
Metabolic transformations of Eucalyptus essential oils by insects

Insects use a diverse range of strategies for coping with the essential oils they encounter in their
food. Some insects cope with the high essential oil content of Eucalyptus leaves by feeding around
oil glands (Ohmart and Edwards 1991) or sequestering them within the body (Morrow
et al. 1976). Others may simply tolerate the oils, while still others possess mechanisms for
metabolising and detoxifying them.
Morrow and Fox (1980) showed that the gas chromatographic profile of faeces from both
Paropsis atomaria and Anoplognathus montanus fed on a range of Eucalyptus species was not signifi-
cantly different from that of the ingested oils. They concluded that the oils are tolerated but not
detoxified, even though many of the oil components induce polysubstrate membrane oxidases in
other species. Similarly, Southwell et al. (1995) found that Paropsisterna tigrina produced frass
with an essential oil profile almost identical to that of the ingested leaf when fed Melaleuca leaf,
unless cineole was a significant component of the diet. For high-cineole diets, the beetles (adults
and larvae) oxidised the bulk of the cineole to (%)-2!-hydroxycineole while other oil compo-
nents were unchanged. Ohmart and Larsson (1989) found that larvae of P. atomaria absorbed or
converted the majority of essential oils of E. blakelyi leaves, of which most (&75 per cent) was
again cineole. They found no evidence of sequestration of the oils and concluded that the oils are
metabolised by the larvae. However, proportions of the two other main components of the oil
(limonene and "-pinene) were similar in the frass and the leaves, which appears to be consistent
with the findings of Southwell et al. (1995) that cineole is metabolised while the other compo-
nents pass through the gut unchanged. Oil budgets were provided for total oils and for cineole
alone, and it was not clear whether the absorption of cineole entirely explained the effect seen in
the total oils. Ohmart and Larsson (1989) also drew attention to the fact that when Morrow and
Fox (1980) fed leaf of E. elata to P. atomaria the major component of the oil, piperitone, was
removed and presumably metabolised.
Just how the essential oils are metabolised by insects is still unknown. Monoterpene com-
pounds are known to induce mixed function oxidase (MFO) activity (Moldenke et al. 1983)
which accords with studies by Rose (1985) who found that insects with high MFO activity
invariably fed on hosts (including Eucalyptus) containing monoterpene compounds. The study of
Southwell et al. (1995) is the most recent study in this area and concludes with the statement
that the oxidase source (microbial or gut enzymes) is unknown. Clearly then, there is much to be
learnt about insect metabolism of Eucalyptus essential oils.
The role of terpeneacylphloroglucinol adducts in food choice of

mammals and insects
Data on the role of essential oils in mediating feeding by folivorous mammals and insects on
Eucalyptus have not been clear and we are now beginning to realise that perhaps their role has
been overstated. Nevertheless, as described above, they may play a very important role due to
their very close relationships with another group of compounds, the acylphloroglucinols, which
have only relatively recently been discovered, and for which evidence of an antiherbivore role is
accumulating rapidly, for both mammalian and insect herbivores.

Earlier, we described the structures of these compounds and their molecular relationship with
the essential oils. It is unfortunate that our current state of knowledge is such that we cannot
discuss in greater detail the biosynthesis of these compounds or provide a mechanistic explana-
tion of the relationship. Nevertheless, we do know that all of the currently identified active
deterrent acylphloroglucinol compounds contain either a terpene side chain or, at the very least,
an isoprene unit (the basic building block of terpenes). There is a strong correlation between the
concentrations of terpenes and of acylphloroglucinol compounds in four Eucalyptus species that
(a) 60
50
Dry matter intake
40
(g . kg0.75 . d1)
30
20
10
0
0 2 4 6 8 10 12 14
Total acylphloroglucinol concentration
(105 moles . g1)
(b) 40
35
30
Dry matter intake
(g . kg0.75 . d1)
25
20
15
10
0
0.0 1.5 3.0 4.5 6.0
Macrocarpal G concentration
(105 moles . g1)
Figure 15.7 Relationship between food intake of common ringtail possums and total acylphlorogluci-
nol/macrocarpal G content of: (a) Eucalyptus ovata leaves, (b) an artificial diet. Note that
data for leaves are total acylphloroglucinols as there is no existing assay specifically for
macrocarpals (although mass spectrometry shows that acylphloroglucinols in E. ovata are
predominantly macrocarpals) (after Lawler et al. 1998a).

have been examined closely (Foley, Matsuki and Floyd unpubl.). In mammalian herbivores, at
least, the secondary correlation between food intake and essential oil concentration is due to the
primary relationship between the oils and the acylphloroglucinols. The development of the
evidence for this is discussed in this section.
Pass et al. (1998) investigated the difference between palatable and unpalatable forms of E. ovata
by a process of bioassay-guided fractionation. They found that the differences between the two
forms in their ability to deter feeding by common ringtail possums were principally due to the
higher concentration of a compound called macrocarpal G (Figure 15.1f), an acylphloroglucinol
with an adduct of bicyclogermacrene a relatively uncommon sesquiterpene found in Eucalyptus.
This led Lawler et al. (1998) to conduct more comprehensive experiments with ringtail possums,
examining a range of palatabilities of individual E. ovata trees to the animals. As discussed above,
the resultant range of intakes correlated strongly with the essential oil content of the leaves (Figure
15.4a) but bioassay experiments showed that essential oils could not cause the effects seen
(Figure 15.4b). In contrast, bioassays with purified macrocarpal G reproduced the range of reduced
intakes in concentrations that corresponded closely with those found in the leaves (Figure 15.7) and
it was concluded that macrocarpal G was the primary cause of feeding deterrence in E. ovata.
Difficulties in the extraction and purification of macrocarpals led us to investigate the deter-
rent properties of related compounds. The initial focus was on jensenone (Figure 15.1d) as it was
listed by Boland et al. (1991) as a major component of the steam distillate of E. jensenii, and was
thus likely to be relatively easy to extract and purify in suitable quantities. This was achieved
and a number of experiments have been carried out with jensenone added to the diets of com-
mon ringtail and common brushtail possums. These have shown jensenone to be a potent
antifeedant in molar quantities very similar to those found for macrocarpal G. Further work has
indicated that their mechanism of action is due to stimulation of the animals emetic systems
(Lawler, Pass and Foley unpubl.).
More recent work has focused on sideroxylonals (dimers of jensenone) as they are found in
variable concentrations in a number of Eucalyptus species, are often the predominant
60
50
40
Dry matter intake
(g . kg0.75 . d1)
30
20
10
0
0 5 10 15 20 25 30
Sideroxylonal concentration
(mg . g1)
Figure 15.8 Relationship between food intake of common ringtail possums and sideroxylonal content
of Eucalyptus polyanthemos leaves (Lawler unpubl.).

acylphloroglucinol in those species (Eschler, Pass and Foley unpubl.), and methods have been
developed to quantify precisely the amounts found in the leaves. These compounds, too, show
strong correlations with the range of food intakes by common ringtail possums (Figure 15.8) and
preliminary evidence suggests that this applies also to koalas (Moore and Foley unpubl.).
Bioassay experiments have again supported the conclusion that sideroxylonals are responsible for
feeding deterrency in those plants where concentrations are sufficiently high (Lawler, Eschler and
Foley unpubl.). Once again we see the correlation between essential oils and both food intakes
and sideroxylonal concentrations, suggesting that the oils do not have a causal antifeedant effect.
There are, so far, few data on the effects of acylphloroglucinols on insect feeding. Correlations
between defoliation and sideroxylonal concentrations of leaves have been shown (Foley and Floyd
unpubl.), but bioassays have not yet been conducted. Hence the same problems as described pre-
viously with correlative studies are encountered, and we cannot yet say that acylphloroglucinols
are the cause of deterrency in insect-resistant trees. Work in this area should advance rapidly
since the problems of headspace concentrations associated with essential oils do not occur with
acylphloroglucinols.
Efficacy of selecting high essential oil genotypes in conferring natural

herbivore resistance on Eucalyptus plantations
The selection of herbivore-resistant genotypes for Eucalyptus plantations may be a practical
approach to protecting them from damage by both vertebrate and invertebrate herbivores (Floyd
and Farrow 1994). However, we conclude with a word of caution on selecting for genotypes con-
taining high concentrations of essential oils to confer this resistance as suggested by Farrow
(1993) and Stone and Bacon (1994).
There is now some evidence that for mammalian folivores essential oils are not the actual
deterrents, but appear so because their concentrations are correlated with acylphloroglucinol
compounds. Whether this is also the case for insects cannot currently be assessed, due to the dif-
ficulties associated with mixing free essential oils into basal diets. There is no doubt that essen-
tial oils are absorbed and metabolised, in some cases, by both insect and mammalian folivores,
though there is little compelling evidence that the rate of metabolism is limiting to food
intakes.
In any case, the selection of resistant genotypes is a sound approach. Difficulties may arise,
however, if this resistance is then attributed to the wrong compound and selection is based on
that criterion rather than resistance per se. It appears that the concentrations of essential oils and
of acylphloroglucinol compounds are closely related, so selection of high essential oil genotypes
may be successful, as long as that selection also selects for correspondingly high acylphlorogluci-
nol contents. However, our knowledge of the biosynthesis of acylphloroglucinols, and its
relationship with the biosynthesis of essential oils, is sorely lacking at present. There is a distinct
danger that at some point in the artificial selection process the relationship between concentra-
tions of the two groups of compounds may break down, and that high essential oil genotypes
may no longer contain high acylphloroglucinol concentrations. This danger is especially signifi-
cant where genetic engineering may be used to manipulate a single factor, such as cineole
production, unless flow-on effects on related compounds are also assessed.
We believe that in this instance mammalian folivores at least, and perhaps insects, would
rapidly learn, within a local area, that high essential oil contents are not associated with negative
effects and will commence to feed on those plants at a high rate. It now appears that mammalian
folivores of Eucalyptus avoid high essential oil diets as the result of a conditioned food aversion,
and there is strong evidence to suggest that these aversions are lost rapidly where there is

repeated exposure to the taste stimuli in the absence of the negative feedback. This would be the
case for a high essential oil/low acylphloroglucinol Eucalyptus plantation.
Whether this effect would be seen for insect herbivores of Eucalyptus is less certain. For the
reasons discussed above, the actual role of essential oils in determining resistance of foliage
against any insect herbivore remains uncertain. Furthermore, if, indeed, essential oils prove not
to be the causal agents then there is less information on the insects ability to learn to eat these
leaves over either a single generation or evolutionary time. That is, there may be an immediate
behavioural response to encountering edible high essential oil plants, or there may be a reduc-
tion in selection for avoidance due to reduced mortality or increased performance of those insects
feeding on high essential oil plants. It was shown by De Little and Madden (1975) that
Chrysoptharta bimaculata, a significant pest of Tasmanian Eucalyptus plantations, may choose to
oviposit on species on which larval growth and survival rates were subsequently shown to be
lower (Baker 1995) than those on other species present. Thus there may be the opportunity for
at least the larval stages to encounter plants rich in essential oils and to learn that these plants are
a suitable food source, again undermining the resistance conferred by the essential oils.
It is important then, that in the attempts to develop these herbivore-resistant plantations the
questions and gaps in our knowledge outlined in this chapter are addressed. At the very least,
caution is advised in this endeavour, and the resistance of genotypes intended for use should be
checked regularly and directly on the animals concerned, until we have confidence in the attrib-
utes to which we attribute herbivore resistance.
Acknowledgements
We thank Dr Bart Eschler, Dr Darren Schliebs and Mr Bruce Clarke for their assistance with lab-
oratory work and discussion of the chemistry and role of acylphloroglucinols in animal feeding.
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16 Eucalyptus oil products
Formulations and legislation
Judi Beerling, Steve Meakins and Les Small
Introduction
Eucalyptus oils are being used with increasing frequency in a variety of products found in the
supermarket or pharmacy. With extract of Eucalyptus or With Eucalyptus essential oil claims
are becoming more common on the labels of modern consumer products such as cosmetics,
toiletries and household products due to the ever-increasing interest in natural or botanical
ingredients. Eucalyptus oil may be used as an active ingredient to provide scientifically provable
benefits such as nasal decongestion or antibacterial effects or at much lower dosages to
impart more esoteric or folkloric connotations to the product concerned. Eucalyptus oils are also
used as components of perfumes to provide a medicinal-type note to the fragrance.
Eucalyptus globulus, or Blue Gum, oil was a traditional Australian aboriginal remedy for infec-
tions and fevers. It is now used all over the world for relieving coughs and colds, sore throats and
other infections. Its main constituent, 1,8-cineole, is mucolytic (i.e. it thins out and relaxes the
flow of mucus) and is excreted through the lung surface. E. radiata oil is sometimes preferred by
aromatherapists for its more pleasant smell while E. smithii oil is sometimes preferred due to a
perception that it is better tolerated by the skin. E. radiata and E. smithii oils have also been
shown to be useful for treating disorders of the respiratory system, although with some differ-
ences in their uses. A steam inhalation with Eucalyptus1 is not only an effective cold treatment
because it relieves nasal and bronchial congestion, but because it is also claimed to inhibit
proliferation of the cold virus (Davis 1990).
When applied as a diluted oil on the skin Eucalyptus has a warming and slightly anaesthetic
effect. Massaging with such an oil, therefore, will help to relieve respiratory infections, pain
caused by rheumatic joints, neuralgia, fibrositis and muscular aches. Burns, blisters, insect bites
and skin infections such as abscesses are also claimed to respond positively to the topical
application of the essential oil or extract. It is also said to be valuable for easing the symptoms of
shingles, chickenpox and cold sores.
Another common name for eucalyptus is Fever Tree. Baron Ferdinand von Mller, the
German botanist and explorer who was Director of the Botanical Gardens in Melbourne from
1857 to 1873, is credited with making the properties of eucalyptus known outside Australia.
Due to the medicinal smell of the leaves, nineteenth century colonists planted the trees in
fever-ridden areas in various parts of the world in an attempt to drive away insects and contagious
1 The term Eucalyptus (i.e. spelt with an initial capital letter) is used in this chapter to denote a formulation or
product containing eucalyptus oil, or the oil itself. Likewise, other oil or resinoid ingredients such as Geranium,
Lavender, Benzoin, etc. are generally spelt with a capital letter.

diseases. Since the high water-holding capacity of the trees root systems coincidentally tended
to dry out marshy soils, disease-carrying insects such as mosquitoes, which need standing water
to breed, were effectively deterred.
Topically applied oils from certain eucalypts also repel mosquitoes from the skin. A prepara-
tion from E. citriodora, Lemon-scented Gum, has been used in China for many years under the
name Quwenling. In Europe, a formulation based on Quwenling is now being used in natural
insect repellent products such as Mosi-guard Natural, marketed by MASTA in the UK (see
below; see also Chapter 14 for a more detailed discussion of Quwenling and Mosi-guard).2
The use of eucalyptus oils in perfumery
Cineole-rich oils
Although more generally associated with medicinal usage, E. globulus oil is the most common
eucalyptus oil used in perfumery. It consists mainly (approximately 7075 per cent) of 1,8-
cineole (sometimes referred to as eucalyptol and, occasionally, as cajeputol). Cineole has a
molecular weight of 154 and boils at 176C. The remainder of the oil consists of a complex
mixture of monoterpenes, sesquiterpenes, sesquiterpenols, aliphatic alcohols, monoterpenones
and aldehydes (see Chapter 5).
Apart from contributing to the fragrance, 1,8-cineole has two important pharmacological
properties: it stimulates the mucous-secreting cells in the nose, throat and lungs and it has an
antiseptic effect. E. globulus oil is a low-cost essential oil which is comparatively stable in soap
(and has long been known for its antiseptic properties, e.g. Martindale 1910) and Poucher
(1991) reports an effective antiseptic natural soap perfume. It consists of:
Geranium 200
Lavender 200
Lemon 200
Cassia 100
Clove 100
Rosemary 80
Eucalyptus 50
Thyme 50
Vetivert 20
Total 1000
It is often the case that small amounts of Eucalyptus are used to claim aromatherapy effects,
even though the contribution to the overall fragrance theme is minimal. However, in a floral
fragrance for soap the inclusion of only 0.5 per cent of Eucalyptus can have a lifting effect on the
fragrance.
Eucalyptus oil is used in many Australian products, such as fabric softeners and shampoos, in
order to support a product-marketing theme. Australian wool wash detergents also often include
eucalyptus oil because of its renowned stain-removing properties. However, in most countries an
overt eucalyptus note would not be acceptable.
2 Mention of any product name in this chapter is for illustrative purposes only and is not intended as a recommendation.
There may be other products which are just as effective for the intended use.

1,8-Cineole is stable in hypochlorite bleach and actually stabilises the chlorine loss.
Eucalyptus oil, or cineole itself, is therefore often used in fragrances designed to be incorporated
in bleach products at levels between 5 and 35 per cent.
Thus, it can be seen that eucalyptus oil, and its constituent 1,8-cineole, have a valuable place in
the perfumers palette because of the powerful message delivered by such a characteristic odour.
As an alternative to using the oil itself, a solvent extract (termed an absolute) can be pro-
duced from the leaves and branches of E. globulus. This is usually solid at room temperature and
has an aromatic-fruity note rather than the typical eucalyptus odour. It has found use in alcoholic
fragrances but is more expensive to produce than the oil and is not so widely used.
Eucalyptus citriodora and other oils

E. citriodora oil, like citronella oil, has a lemon-like odour and contains citronellal as the princi-
pal constituent. However, when a clean citrus effect is required, one that can be seen as very
functional smelling, then E. citriodora oil is the product of choice. Hence its use in laundry soaps
and powders; it is especially popular in Africa for this purpose. It is also used in other low-cost
soaps, perfumes, air fresheners and disinfectants.
E. staigeriana oil from Brazil also has a lemon-like character this time due to the presence of
citral and although it is used in perfumery its limited availability and rather higher price
means that it is not used on anything like the scale of E. citriodora oil.
The safety of eucalyptus oils in fragrances

Although the fragrance industry is covered by normal consumer protection laws, it has also
established a self-regulatory mechanism to ensure that the ingredients used in fragrances do not
pose a risk to the consumer. This self-regulatory system involves the close cooperation of two
major international fragrance organisations: the Research Institute for Fragrance Materials
(RIFM) and the International Fragrance Association (IFRA). The addresses and other contact
details for both organisations are given in Appendix 7.
Research Institute for Fragrance Materials

RIFM was established in 1966 by the American Fragrance Manufacturing Association as a non-
profit making, independent body whose task is to check the safety of fragrance ingredients. To
date, RIFM has tested over 1300 fragrance materials, including all of the commonly used ingre-
dients. The test results for each material examined are reviewed by an independent international
panel of toxicologists, pharmacologists and dermatologists and the results are published as
monographs in the journal Food and Chemical Toxicology. RIFM also collates all the information
available for an ingredient from the scientific literature and from the aroma chemical manufac-
turers for inclusion in these monographs. Should there be any cause for concern about the use of
an ingredient this is immediately signalled to the industry by RIFM through the publication of
an advisory letter, which is then acted upon by IFRA.
The type of basic tests carried out by RIFM include acute oral toxicity; acute dermal toxicity
if the oral toxicity is significant; skin irritation and sensitisation; and phototoxicity if the mate-
rial absorbs in the UV range. Where there is a need, more detailed studies are undertaken
involving sub-chronic feeding, dermal absorption and metabolic fate. Through IFRA, RIFM
also collects from the industry consumer exposure data on fragrance ingredients. This ensures
that the test data it has are relevant to the market situation and also provides guidance on the

requirements for future research. Thus, RIFM will undertake a review of its safety data, or insti-
gate further research, if the results of these surveys indicate that a particular ingredient is occur-
ring in a wider range of products and/or at higher concentrations than was the case when it was
first examined.
International Fragrance Association

IFRA was established in 1973 by trade associations representing over 100 fragrance manufac-
turers in fifteen countries. It represents the scientific and technical expertise of the industry and
is responsible for issuing and up-dating the Code of Practice upon which the whole self-regulation
policy is based. IFRA is funded by these fragrance manufacturing companies, who all agree
to abide by the code of practice whilst they remain members of the association. This code of
practice has many functions, including setting standards for good manufacturing practice
within the industry, as well as standards for quality control and for labelling and advertising. It
also sets limits on, or prohibits the use of, certain ingredients.
Although IFRA and RIFM are independent of each other they work closely together and it is
only after considerable discussion between them that restrictions or prohibitions are imposed. It
is always the IFRA board in conjunction with the technical advisory committee who make the
final decision in such matters, as they are ultimately responsible for the implementation of any
restrictions, by way of the code of practice. The most common cause for a use restriction is the
ability of some materials to be skin sensitisers. Unlike skin irritation, which usually disappears
soon after the irritant has been removed, skin sensitisation involves the activation of the immune
system and reactions can persist for much longer after the initial exposure and become more
severe on subsequent contact. The strict code of practice applied by IFRA not only protects the
consumer but also protects the health and well-being of those employed within the industry.
E. globulus and E. citriodora oils

Eucalyptus oil of the type from E. globulus, and that from E. citriodora, have both been the sub-
jects of RIFM monographs (Opdyke 1975, Ford et al. 1988). Opdyke (1975) also gives a separate
monograph on eucalyptol. Neither oil has been found to be harmful, irritating or sensitising.
Both oils were tested on human volunteers in 48-h closed patch tests at a concentration of 10 per
cent in petrolatum and neither was irritating. E. globulus oil was also tested undiluted and still
gave a negative result. When subjected to a human maximisation test, again at a level of
10 per cent in petrolatum, neither oil was found to be sensitising (Kligman 1966, Kligman and
Epstein 1975). Use of these oils in fragrance compositions is therefore not restricted by IFRA.
The use of eucalyptus oils in consumer products
Insect repellents
As noted in the introduction, E. citriodora oil has been used as a natural insect repellent.
Depending on the product formulation it is used in, Lemon Eucalyptus (known as Quwenling in
China) is up to four or five times more effective and longer-lasting than citronella oil (from
Cymbopogon nardus), one of the best known natural insect repellents. p-Menthane-3,8-diol is the
main active component of Quwenling and this can be isolated and used as a highly effective
insect repellent. E. citriodora oil contains up to 8090 per cent citronellal, along with geraniol,
both of which are known to have insect repellent activity but tend to dilute the much higher
activity of the p-menthane-3,8-diol.

The Mosi-guard Natural insect repellent spray produced by MASTA in the UK contains
Extract of Lemon Eucalyptus and claims on the label:
Approved and recommended by the London School of Hygiene and Tropical Medicine.
Field trials have shown effective protection for 6 h after a single application in mosquito
infected areas. Also protects against many other biting insects. Mosi-guard Natural is made
from a natural and renewable resource. It is kind to your skin and has no adverse effects on
fabrics and surfaces. Apply Mosi-guard Natural to exposed areas as often as required.
E. citriodora was traditionally used for perfuming the linen cupboard by putting the
dried leaves in a small cloth sachet. During the last century, its use as an insect repellent was
recognised, especially against silverfish and cockroaches.
The use of eucalyptus oil as a natural flea repellent, sprayed around the home three times a
week as a dispersion in water, has also been advocated. Pets and their bedding can be sprayed
with the same solution. An equine shampoo, containing eucalyptus oil as a natural insect
repellent, is also available for sale on the Internet.
The insect repellency properties of eucalyptus have also been reportedly used in mosquito
mats in India.
Medicinal uses
Today, the number and diversity of medicinal products containing eucalyptus oil which are mar-
keted is very large indeed. This is illustrated in Table 16.1 which lists some, but by no means all,
of the products which are available in Australia, Europe, Thailand and the United States. Note
that there are many more products which contain eucalyptol (cineole) and although these are
derived from eucalyptus oil they are not included in Table 16.1.
Eucalyptus is widely used for the treatment of asthma, bronchitis, catarrh, colds, influenza
and sinusitis. Vaporisers and aromatherapy oil burners can be used in the home to distribute the
essential oil odour around the room, helping to purify the air and aid breathing. There are also
numerous inhalation/chest rub products on the market, one of the most well-known being Vicks
VapoRub (Proctor & Gamble), which has been marketed for over eighty years. The oils used in
this, and similar products, which have demonstrated a clinically significant contribution to the
overall nasal decongestant effects of the product, are Eucalyptus, Camphor and Peppermint
(menthol). Vicks VapoRub ointment contains as active ingredients: Camphor B.P. 5.46% w/w,
Menthol B.P. 2.82% w/w, Turpentine oil B.P. 4.71% w/w and Eucalyptus oil B.P. 1.35% w/w in
a petrolatum base. Non-medicinal ingredients are typically Cedar leaf, Nutmeg and Thymol.
A typical formula for a decongestant oil is:
Wintergreen 27
Camphor 23
Peppermint 20
Turpentine 18
Eucalyptus 8
Cedar leaf 2
Nutmeg 2
Total 100
This is then mixed with pure petroleum jelly for use as a chest rub or encapsulated for use
with hot water as a decongestant.

Table 16.1 Examples of pharmaceutical products containing eucalyptus oil which are marketed in
Australia, Europe, Thailand and the United Statesa, b
Product name Manufacturer Treatment
Australia
Alcusal Sport Alcusal Sports injuries
Analgesic Rub J. McGloin Muscle and joint pain
Biosal Yauyip Arthritic pain
Bosistos Eucalyptus Inhalant Felton Grimwade & Bickford Cold symptoms
Bosistos Eucalyptus Rub Felton Grimwade & Bickford Muscular aches and pains
Dencorub Carter Wallace Musculoskeletal pain
Dentese J. McGloin Toothache
Euky Bear Eu-Clear Inhalant Felton Grimwade & Bickford Cold symptoms, respiratory tract
congestion
Euky Bearub Felton Grimwade & Bickford Cold symptoms, nasal congestion,
muscular aches and pains, insect
bites
Logicin Chest Rub Sigma Pharmaceuticals Respiratory tract congestion
Methyl Salicylate Compound J. McGloin Muscle pain
Liniment
Metsal 3M Pharmaceuticals Rheumatic pain, arthritis, sprains
and strains
Vicks Vapodrops Procter & Gamble Nasal congestion, sore throat
Vicks VapoRub Procter & Gamble Cold symptoms
Zam-Buk Key Pharmaceuticals Minor skin disorders
France
Balsofletol Laboratoires Pharmascience Nose and throat infections
dulcor eucalyptus et menthol Laboratoires Pierre Fabre Sore throat
Eucalyptine Le Brun Laboratoires Janssen Coughs
Inongan Laboratoires Fumouze Muscle pain
Kamol Whitehall Localised pain and injury
Nazophyl Laboratoires Mdecine Rhinitis, rhinopharyngitis, sinusitis
Vgtale
Pulmax Laboratoires Zyma Respiratory tract congestion
Pulmoll au menthol Sterling Midy Throat disorders
et leucalyptus
Sirop Pectoral Laboratoires Oberlin Coughs
Thiopon Balsamique Laboratoires Amido Upper respiratory tract infections
Trophirs Compos Millot-Solac Respiratory tract disorders, coughs,
fever
Tussipax lEuquinine Laboratoires Thrica Coughs
Vicks Pastilles Laboratoires Lachartre Sore throats
Vicks Vaporub Laboratoires Lachartre Respiratory congestion
Germany
Aerosol Spitzner N W. Spitzner Respiratory tract disorders
Angocin percutan Repha Respiratory tract disorders, muscle
and joint pain
Aspecton-Balsam Krewel-Werke Coughs, cold symptoms
Babiforton Plantorgan Respiratory tract catarrh
Babix-Inhalat N Mickan Arzneimittel Respiratory tract disorders
Baby-Transpulmin Asta Medica Cold symptoms
Bronchicum Sekret-Lser A. Nattermann Upper respiratory tract disorders
Bronchodurat G. Pohl-Boskamp Bronchitis, cold symptoms
Bronchoforton Plantorgan Bronchitis, sinusitis
Divinal-Broncho-Balsam Divinal Arzneimittel Respiratory tract disorders

Dolo-cyl Pharma Liebermann Musculoskeletal and joint disorders,

sports injuries
Emser Balsam echt Siemens Respiratory tract disorders
Emser Nasensalbe N Siemens Colds, hay fever
Ephepect Bolder Arzneimittel Bronchitis, catarrh
Eucabal-Balsam S Esparma Pharmazeutische Respiratory tract disorders
Fabrik
Eucafluid N Steigerwald Arzneimittelwerk Musculoskeletal and joint disorders
Eufimenth N mild Lichtenstein Pharmazeutica Respiratory tract disorders
Hevertopect Hevert-Arzneimittel Respiratory tract disorders
Hustagil Dentinox Coughs, respiratory tract disorders
Inspirol N Solution Lyssia Mouth and throat disorders
Kneipp Erkltungs-Balsam N Kneipp-Werke Coughs, respiratory tract disorders
Leukona-Eukalpin-Bad Dr Atzinger Pharmazeutische Bath additive, respiratory tract
disorders
Liniplant W. Spitzner Upper respiratory tract disorders
Logomed Erkltungs- Logomed Pharma Upper respiratory tract disorders
Balsam Creme
Makatussin Balsam Menthol Roland Arzneimittel Catarrh, bronchitis
Melrosum Inhalationstropfen A. Nattermann Cold symptoms
Mentholon Original N Richard Schning Catarrh
Nasivin Intensiv-Bad E. Merck Respiratory tract congestion
Nervfluid S Fides Vertrieb Pharm. Nerve, muscle and joint pain
Prparate
Palatol Pascoe Pharm. Prparate Catarrh
Piniol N W. Spitzner Respiratory tract disorders
Pulmotin-N Serum-Werk Bernburg Respiratory tract disorders
Pumilen-N E. Tosse Colds, nasal congestion
Repha-Os Repha Inflammatory disorders of oropharynx
Retterspitz Aerosol Retterspitz Respiratory tract infections
Salviathymol N Galenika Dr Hetterich Inflammatory disorders of oropharynx
Sinuforton (oral drops) Plantorgan Sinusitis
Thymipin N (cream) Zyma Coughs, respiratory tract disorders
Tumarol-N Robugen Colds
Tussipect Beiersdorf Coughs, respiratory tract disorders
Italy
Antipulmina Lisapharma Respiratory tract disorders
Capsolin Parke Davis Joint and muscle pain
Eucalipto Composto Dynacren Nasal congestion
Fomentil SIT Respiratory congestion
Rinostil Laboratorio Chimico Deca Inflammation of nose and throat
Sloan Parke Davis Musculoskeletal and joint pain
Vicks Gola Proctor & Gamble Oropharyngeal disorders
Vicks Vaporub Proctor & Gamble Upper respiratory tract disorders
Spain
Bellacanfor Bicther Rheumatic and muscular pain
Gartricin Cantabria Mouth and throat inflammation
Lapiz Termo Compositum Domenech Garcia Rheumatic and muscular pain
Porosan Reig Jofre Upper respiratory tract disorders, soft
tissue and muscular disorders
Termosan Domenech Garcia Upper respiratory tract disorders, soft
tissue disorders, muscular pain
Vicks Vaporub Procter & Gamble Upper respiratory tract disorders

Switzerland
Antiphlogistine Carter-Wallace Pain, inflammation
Baby Librol Galactina Colds, fever
Baume Kytta Whitehall-Robins Musculoskeletal and joint disorders
Bismorectal Vifor Oropharyngeal disorders
Bradoral Zyma Oropharyngeal disorders
Bronchoforton N Sterling Health Respiratory tract disorders
Capsolin Parke, Davis Musculoskeletal pain
Demo ptes pectorales Demopharm Coughs, bronchitis
Embropax Taphlan Peri-articular and soft tissue disorders
GEM Piraud Coughs, throat disorders
Huile analgsique Polar-Br Panax Import, F. Ruckstuhl Headache
Huile Po-Ho A. Vogel Bioforce Homeopathic preparation
Kemeol Interdelta Nasal congestion
Librol Galactina Muscle and joint pain, chilblains, cold
symptoms
Makatussin (oral drops) Makapharm Coughs, catarrh
Massorax Laboratoire RTA Joint and soft tissue disorders
Nasobol Sodip Respiratory tract disorders
Pasta boli Spirig Musculoskeletal and soft tissue pain
Phlogantine G. Streuli Musculoskeletal inflammation,
bronchitis, skin disorders
Pinimenthol Piniol Influenza, muscle and joint pain
Pirom Solmer Muscle and joint pain, headache,
sports injuries, insect bites
Pulmex Zyma Respiratory tract disorders
Rhinothricinol Laboratoires Plan Rhinopharyngeal infections
Roliwol ECR Pharma Muscle and joint pain
Sloan Baum Warner-Lambert Musculoskeletal and joint disorders
Tumarol Renapharm Cold symptoms
Vicks VapoRub Procter & Gamble Upper respiratory tract disorders
Thailand
Golden Cup Balm Golden Cup Pharmaceutical Muscular rheumatism, strains, insect
bites, eczema
Golden Lion Balm Jack Chia Industries Minor muscular aches and pains
Golden Snake Balm L.P. Standard Laboratories Minor muscular aches and pains,
sprain, headache, insect bites
Neotica Analgesic Balm Thai Nakorn Patana Muscular aches and pains, sprains,
sports injuries, insect bites
White Monkey Holding Monkey Holding Peach Brand Minor muscular aches and pains,
Peach Balm sprain, insect bites
United Kingdom
9 Rubbing Oils Potters Herbal Supplies Rheumatic and muscular pain
Aleevex Pure Plant Products Cold symptoms
Cabdrivers Opal Products Coughs
Catarrh Cream Weleda Nasal congestion
Catarrh Pastilles Healthcrafts Cough and cold symptoms
Chymol Emollient Balm Rosmarine Manufacturing Chapped skin, chilblains, bruises,
sprains
Cupal Baby Chest Rub Cupal Bronchial congestion
Deep Heat Rub Mentholatum Rheumatic and muscular pain
Dragon Balm Gerard House Muscular aches
Fishermans Friend Lofthouse of Fleetwood [Confectionery]
Gonne Balm G.R. Lane Health Products Muscular pain

Mackenzies Smelling Salts Cox Pharmaceuticals Catarrh, head colds

Medicinal Gargle Weleda
Mentho-lyptus Warner-Lambert Confectionery Cold symptoms, sore throats
Mentholease Warner-Lambert Health Care Hay fever
Merothol Marion Merrell Dow Mouth and throat infections, nasal
congestion
Nicobrevin Intercare Products Aid to smoking withdrawal
Olbas Oil G.R. Lane Health Products Bronchial and nasal congestion, hay
fever, muscular pain
Olbas Pastilles BCM for G.R. Lane Health Colds, coughs, catarrh, sore throats,
Products flu, catarrhal headache, nasal
congestion
Oleum Rhinale Weleda Catarrh, sinus congestion
Penetrol Seton Healthcare Nasal congestion
Potters Decongestion Pastilles Ernest Jackson Blocked noses, coughs, catarrhal colds
Proctors Pinelyptus Pastilles Ernest Jackson Throat irritation, coughs
Sandersons Throat Specific Sandersons Sore throat, catarrh
Snufflebabe J. Pickles & Sons Congestion
Soothene G.R. Lane Health Products Minor skin disorders
Strepsils Menthol & Eucalyptus Crookes Healthcare Sore throat, mouth infections, nasal
congestion
Tixylix Inhalant Novartis Consumer Health Nasal congestion
Vicks Vaporub Proctor & Gamble (H&B Care) Congestion
Zam-Buk Roche Consumer Wounds, skin abrasions
United States
Capastat SmithKline Beecham Sore throat
Eucalyptamint Ciba Pharmaceutical
Halls Sugar Free Mentho-Lyptus Warner-Lambert Sore throat
Massengill Beecham Products Vaginal disorders
Maximum Strength Flexall 454 Chattem Consumer Products Pain, musculoskeletal disorders
Mexsana Schering-Plough Nappy rash
Robitussin Cough Drops Whitehall-Robins Coughs
Unguentine Ointment Mentholatum Pain in minor burns
Vicks Menthol Cough Drops Procter & Gamble Sore throat
Vicks VapoRub Procter & Gamble
Vicks Victors Dual Action Richardson-Vicks Coughs
Cough Drops
Source: RPS (1996), Ody (1996) and retail outlets in the UK and Thailand.
a Products containing ingredients listed as eucalyptol/cineole are not included.
b The list is intended to be illustrative rather than exhaustive. Some products may no longer be marketed; or they may
be used for the treatment of conditions different, or additional, to those described; or they may no longer be labelled
as containing explicitly eucalyptus oil. Company names may also have changed.
Halls Mentho-Lyptus cough suppressants, Listerine mouthwash, Olbas oil and vari-
ous nasal inhalers are further examples of products utilising the refreshing and expectorant prop-
erties of Eucalyptus. A recent eucalyptus product, Eucalyptamint, has been promoted in the
United States as a treatment for muscle soreness. Researchers at the University of California are
reported to have tested the ointment and discovered that it increases the blood flow to muscle
tissue (Internet 2000).
Tigerbalm is one of the most popular liniments, traditionally used in Asia but now widely
available in the West. A Chinese merchant is said to have composed the first Tigerbalm, based

Table 16.2 Active ingredients and essential oils used in some proprietary preparations containing eucalyptus oil (%)a
Tiger Golden Kwan Neotica Gonne Golden Golden Golden Olbas Olbas
Liniment Cup Loong Analgesic Balm Snake Lion Balm Lion Balm Oil Pastilles
Balm Oil Balm Balm (White) (Red)
Methyl salicylate 38 15 15 15 9 01
Menthol 08 12 25 10 4 10 11.6 15 04.1 0.1
Camphor 15 15 10 02 2 22 08.0 08
Eucalyptus 06 03 10 02 2 03 13.7 06 35.45 1.16
Peppermint 04 16 16.7 10 35.45b 1.12
Clove 0.5 02 6.0 04 0.1 0.0025
Spike lavender 05 07
Turpentine 7
Cajuput 01 10 18.5
Cinnamon 01
Wintergreen 0 3.7 0.047
Juniper berry 02.7 0.067
a Tiger Liniment and Kwan Loong Oil are manufactured by Drug Houses of Australia (Asia) Pte Ltd, Singapore. Manufacturers of other preparations are given
in Table 16.1.
b Dementholised mint oil.

on the ointment that tradition says was used by Genghis Khans Mongolian horsemen and which
was very effective against saddle and backache.
A typical formula is:
Peppermint 25
Wintergreen 20
Camphor 15
Eucalyptus 15
Lavender 15
Vegetable oil 10
Total 100
This is then mixed with pure petroleum jelly (adding the above oil at about 15% w/w). A
small spot is applied to the forehead to alleviate headaches, or it can be rubbed on aching mus-
cles or insect bites. However, in Tigerbalm products currently marketed in the UK eucalyptus
oil appears to have been replaced by cajeput oil (from Melaleuca cajeputi) which also contains a
high level of cineole and has similar warming, expectorant and analgesic properties.
Further examples of active ingredients and essential oils used in some preparations containing
eucalyptus oil, and the proportions used, are given in Table 16.2.
Other applications of eucalyptus oil include its use in a footbath for sore feet (one teaspoon in a
bowl of hot water) and addition to the water used in saunas or steam rooms to invigorate and
relieve congestion. It can also be used to prevent blistering caused by burns or over-exposure to the
sun, to soothe itching caused by insect bites or rashes and to aid healing of sores, cuts and abrasions.
Aromatherapy uses
The reported medicinal and aromatherapeutic properties of Eucalyptus are legendary. Amongst
the properties attributed to E. globulus and other cineole-rich oils by various aromatherapy texts
are the following:
Analgesic Deodorant
Antidiarrhoeal Depurative (cleanses the blood)
Anti-inflammatory Digestive
Antineuralgic (relieves or reduces nerve Diuretic (aids production of urine)
pain) Expectorant
Antiphlogistic (checks or counteracts Febrifuge (reduces fever)
inflammation) Hypoglycemiant (reduces blood sugar
Antirheumatic levels)
Antiseptic Insecticidal
Antispasmodic (prevents and eases Parasiticidal
spasms or convulsions) Prophylactic (prevents disease or
Antiviral infection)
Bactericidal Rubefacient (causes redness of the skin)
Balsamic (soothing, having qualities of Stimulant
a balsam) Vermifuge (expels intestinal worms)
Cicatrisant (promotes healing by Vulnerary (helps heal wounds and sores
formation of scar tissue) by external application)
Decongestant

Aromatherapy texts also recommend Eucalyptus in cases of boils, pimples, dandruff, athletes
foot, measles, nervous exhaustion or fatigue and various other complaints. In addition to its
physical benefits, Eucalyptus is claimed to act on the emotional centre of the brain. With the
properties of centring, balancing and stimulation, it can be used for treating exhaustion, congestive
headaches, an inability to concentrate, mood swings and temper tantrums.
In aromatherapy, Eucalyptus is said to blend well with Angelica, Benzoin, Black pepper,
Cedar wood, Coriander, Geranium, Juniper, Lavender, Lemon, Lemongrass, Marjoram, Melissa,
Peppermint, Pine, Rosemary, Sandalwood, Spearmint, Tea tree, Thyme and Wintergreen. It is
said to combine well with Lemon for mental clarity and with Myrtle for building up the
immune system. The heating effect of Eucalyptus can often be balanced by mixing it with a
cooling oil such as Lavender or Peppermint (to reduce fever).
Personal care products

Table 16.3 lists some examples of personal care products which contain eucalyptus oil, together
with the benefits claimed for them. They are found mainly in the UK market. The list includes
some products (mainly bath additives) which may also be described as having medicinal or aro-
matherapeutic actions. Two other types of product, a general purpose cleaner and a disinfectant,
are shown at the bottom of Table 16.3.
Typical formulations for personal care products

Eucalyptus oils can easily be incorporated into detergent or soap-based products or those based
on alcohol or vegetable/mineral oils. However, their strong odour may conflict with other fra-
grances which are used in the products. Furthermore, in common with other essential oils, euca-
lyptus is not water-soluble and so cannot easily be incorporated in purely aqueous products
without adding a solubiliser (usually a type of non-ionic detergent).
One way of circumventing any odour and water solubility problems is to use one of the many
eucalyptus herbal extracts, widely available around the world, where solvents such as propy-
lene/butylene glycol, glycerol or ethanol are used to extract the fresh plant material. In these
cases, and depending on the extraction methods used, the components of the extract will differ
significantly from those of the essential oils. However, under the sixth Amendment to the EU
Cosmetics Directive the INCI (International Nomenclature for Cosmetic Ingredients) name
used on European product packaging is the same for both oil and extract, namely the Linnaean
botanical name of the plant species used, for example, Eucalyptus globulus. However, the solvent
used, such as propylene glycol, will also appear somewhere in the ingredient listing. In the USA,
the CTFA3 INCI name Eucalyptus Globulus Extract or Eucalyptus Globulus Oil must be used
until such time as the two sets of nomenclature are fully harmonised.
Formulations and methods of preparation for some typical personal care products containing
Eucalyptus are given below, where European INCI names are used throughout.
3 The Cosmetic, Toiletry and Fragrance Association, the leading US trade association for the personal care products
industry, with more than 500 member companies.

Table 16.3 Examples of personal care and other products which contain eucalyptus oil
Product name Manufacturer a Product description Benefit claimed
Baby Breatheasy Bath and Johnson & Johnson Mild baby bath foam and skin Helps to relieve blocked nasal
Breatheasy Cream cream with decongestant action. passages and aids restful sleep
Contains Eucalyptus, Rosemary
and Menthol
Breathe Clear with Extract [For] Sainsburys Foam bath Soothing, aids relaxation and
of Eucalyptus Supermarkets Ltd makes breathing easier. Eucalyptus
oil is renowned for its head-
clearing properties
Carex Bath & Body Wash; Cussons Green, soothing Aloe vera and Dermaclens is a unique new
Liquid Handwash; (International) Ltd Eucalyptus variant of the range moisturising system with
Antibacterial Moisturising of shower and bath body antibacterial action, derived from
Hand Gel cleanser, liquid hand soap and natural oils
waterless antibacterial hand gel
Radox Solutions Sara Lee H & BC Bath and massage oil containing Relieves muscle tension
Spring Unwind Juniper berry and Eucalyptus
Radox Herbal Bath Breathe Sara Lee H & BC Bath foam with Menthol and Renowned for helping to clear the
Easy Eucalyptus head
Original Radox Herbal Sara Lee H & BC Bath foam with Eucalyptus Contains Eucalyptus, well known
Bath Muscle Soak to relieve congestion
Radox Bath Salts Vapour Sara Lee H & BC Water-softening bath salts with Helps to relieve stiff, aching
Therapy Eucalyptus muscles and clear the head.
Contains Eucalyptus which acts as
a decongestant
Fresh! Green Devil Bath The Boots Co. Bath bomb large Recharge yourself with this
Bonanza effervescing bath tablet refreshing Eucalyptus soak
Eucalyptus Spa Bath Aubrey Organics, Bath oil containing blend of Soothes minor muscle strain and
USA (via Internet) Eucalyptus and Menthol tension. Helps open up blocked
sinuses and clear the head
Relax-R-Bath Aubrey Organics, Herbal bath emulsion. Contains Soothes sore muscles and eases
USA (via Internet) soothing blend of roots and tension. Ideal for athletes, dancers
herbs, including ground and for anyone after a hard days
Eucalyptus leaf work

Product name Manufacturer a Product description Benefit claimed
GDay Eucalyptus Bath Aubrey Organics, Vegetable soap base containing Wake up your senses with this
Bar USA (via Internet) Eucalyptus, Menthol and other invigorating deodorant soap bar.
essential oils Menthol and Eucalyptus tone and
deodorise
Breathe Easy Headache Mother Earth Mask that can be chilled or Designed to provide relief for the
Mask Herbals (via heated. Ingredients: Flax seed, pain and discomfort of sinus/cold
Internet) Eucalyptus and Peppermint congestion and allergies
Blue Gum Shampoos and CanCan Products Range of shampoos and Based on Blue Gum Eucalyptus
Aqua Conditioners conditioners essential oil added to promote
healthy hair and scalp
Original Source: Health & Beauty Intensive hair conditioning Inspired by herbal remedies based
Eucalyptus & Mint Solutions Ltd. treatment and various detergent- on the healing power of plants of
Conditioner based products. the Australian outback.
Shampoo Fragranced by natural Stimulating vapours give an
Bath Foam Eucalyptus and Peppermint oils exhilarating and refreshing
Facial Wash sensation
Fresh! Bar Belle Massage The Boots Co. Massage bar that melts on the With refreshing Mint and
Bar skin Eucalyptus to work out and
freshen up
NSR (Natural Sports Rub) Aubrey Organics, Warm-up/rub-down massage Has a warming/cooling action.
USA (via Internet) lotion. Compounded with seven Eases minor muscle tightness and
essential oils, including tension to help relaxation after a
Eucalyptus workout. Helps warm up and
loosen muscles before a workout
Hand Salve a farmers Burts Bees, USA Moisturising and healing hand Soothes the skin and promotes
friend salve with Comfrey, Rosemary, healing. For dry, chapped and
Lavender and Eucalyptus weather-beaten skin

Buzz Off Natural Insect Mother Earth Insect repellent oil. Contains An all natural alternative for
Repellent Herbals (via Eucalyptus and other essential fighting off pesky insects
Internet) oils
Hairwars Healthy head Tisserand Leave-on, vegetable-based hair An original aromatherapy
and hair promoter Aromatherapy oil treatment for head lice formulation. Contains Tea tree,
Products Ltd Eucalyptus and Kanuka oils as a
natural solution to one of lifes
little problems
Head Lice Treatment Lincs Aromatics Complete treatment for head Contains Lavender, Geranium and
(via Internet) lice. Oil, rinse and fine comb Eucalyptus
pack
Soothing Anti-Itch Herbal Aubrey Organics, Skin-soothing balm containing Relieves itching and inflammation
Remedy USA (via Internet) Aloe vera, Canadian Willowherb of rashes and insect bites; soothes
extract and essential oils symptoms of poison oak and ivy.
including Eucalyptus, Lavender, Helps clear skin fungi and yeast
Tea tree and Oregano overgrowth and ease symptoms of
eczema, seborrhoea, psoriasis and
other skin conditions
King of Shaves Shaving Knowledge and Shaving oil containing Camphor, Total sensitive skin protection
Oil. (Shaving gels are also Merchandising Eucalyptus globulus, Mentha
produced containing (KMI) Inc. Ltd viridis (Spearmint) and Menthol
Eucalyptus)
Ajax with Eucalyptus Colgate, France General-purpose cleaner With essences of Eucalyptus
Earth Aware Household Aubrey Organics, General-purpose cleaner (incl. Cleans most surfaces in the home
Cleaner USA (via Internet) laundry detergent). Contains without harming health or the
Rosemary, Sage and Eucalyptus environment
oils
Myo Powerfresh Ultra Wolseley Castle, Disinfectant With real Eucalyptus oil.
Concentrate, Eucalyptus Australia Hospital grade
a All products are manufactured in the UK except where indicated otherwise.

Formulation 1 Aching muscle relief bath foam This formulation is designed to relieve
congestion and help soak away aches and pains due to everyday stresses and strains. It should be
poured into the bath under warm running water.
% w/w
Aqua (purified water) to 100.00
Sodium laureth sulfate, 28% aq. solution ( foaming agent) 45.00
Cocamidopropyl betaine, 40% aq. solution (mild cleanser) 10.00
Cocamide DEA ( foam booster/stabiliser) 2.00
Sodium chloride (thickener) 0.50
Eucalyptus globulus (as essential oil) 0.50
Tetrasodium EDTA (sequestering agent) 0.10
Preservative as required
Parfum ( fragrance)/other essential oils as required
Dyes as required
Citric acid (pH adjuster) to pH 6.00
Preparation: Mix the ingredients in the order given, stirring well after each addition. Adjust the
pH as shown.
Formulation 2 Clear hand cleanser gel This clear antimicrobial gel has been designed to
hygienically cleanse the hands without the need to use soap and water.
% w/w
Phase A
Aqua ( purified water) to 100.00
Alcohol (Ethanol, DEB 100) (solvent/antimicrobial ) 65.00
Acrylates/C10-30 alkyl acrylate crosspolymer (thickener) 0.50
Glycerin (moisturiser) 1.50
Triclosan (bacteriostat) 0.25
Triethanolamine ( pH neutraliser) 0.50
Phase B
Parfum ( fragrance) 0.30
Preparation: Disperse the Acrylates/C10-30 alkyl acrylate crosspolymer in the water and add
the remaining ingredients of phase A. Pre-mix phase B, add to phase A and stir gently until
completely mixed.
Formulation 3 Hair conditioning treatment with Eucalyptus and Mint This thick, creamy hair
conditioner is designed to remoisturise the hair and prevent static build-up. The eucalyptus and
mint essential oils are designed to stimulate the scalp.

% w/w
Phase A
Aqua ( purified water) to 100.00
Hydroxyethyl cellulose (high viscosity grade) (thickener) 1.00
Panthenol (Pro-vitamin B5 hair conditioning agent) 0.50
Phase B
Cetyl alcohol (emulsion stabiliser/bodying agent) 3.00
Dialkyl ester ethyl hydroxyethyl methylammonium methosulfate 2.00
(biodegradable hair conditioning agent)
Isopropyl myristate (emollient oil) 2.00
Phase C
Preservative as required
Citric acid or Triethanolamine ( pH adjuster) to pH 66.5
Mentha piperita (peppermint oil) 0.20
Parfum (fragrance) as required
Preparation: Heat the water of phase A to 75C, stir rapidly and slowly add the hydroxyethyl
cellulose; stir until fully hydrated. Heat phase B to 75C, add phase A to phase B with stirring
and continue stirring until cool. Finally add phase C.
Oral health care

The therapeutic properties of eucalyptus oils and extracts have meant that their use in oral health
care products such as toothpastes, mouthwashes and chewing gums is becoming more common.
Euthymol by Warner Lambert, a traditional style toothpaste, is based on the renowned
natural antibacterial properties of Eucalyptus and thymol. Eucalyptus is believed to kill bacteria
that cause halitosis and is said to be particularly effective against breath problems caused
by strong-smelling food and drink. Microbiological testing by Quest has demonstrated that
E. globulus oil (with an 8085 per cent 1,8-cineole content) has moderate antimicrobial activity
against both Gram-positive and Gram-negative bacteria.
The Eucalyptus may thus be present as an active agent, for example, as a decongestant (along
with menthol) in the Wrigleys Airwaves vapour release chewing gum, or as part of a more
complex flavour compound. Eucalyptus is not common as a predominant flavour ingredient in
oral care products as it has a medicated note that is not liked by some people, particularly in
North America. Clark (2000) cites a 1992 Wall Street Journal article which reported that the
major brands of mouthwash which contain eucalyptol were all losing market share. However,
Eucalyptus is used to give lift and some freshness to oral care flavours.
One interesting application of Eucalyptus is in a mouthwash to combat or reduce snoring. A
product called Good Night Stop Snore is available by mail order in the UK. This is claimed to
be an effective natural remedy for snoring if used every night. The mouthwash contains a blend
of natural essential oils including Peppermint, Thyme, Fennel and Eucalyptus. These are said to
have the combined effect of clearing bronchial congestion, whilst toning and increasing blood
supply to the soft palate.

Another interesting oral care use is in an aromatherapeutic chewing gum, designed to
impart a stress-free mind as well as fresh breath. Peace of Mind Gumballs are marketed by
Origins (Este Lauder) in the USA as part of their Sensory Therapy line. They contain a blend of
relaxing essential oils, including Peppermint, Basil and Eucalyptus. The latter is added for its
tranquil effect.
Research by Osawa and Yasuda at the Lotte Central Laboratory in Japan found that extracts
of the dried leaves of E. globulus showed appreciable antibacterial activity against the bacteria
that cause dental caries and periodontal disorders (Anon 1996). The researchers identified eight
compounds that exhibited antibacterial behaviour, three of which (macrocarpals) had never been
isolated before (see also Chapter 12). These macrocarpals have greater antibacterial activity than
thymol, commonly used as an oral antibacterial agent. The extracts also act as inhibitors of glu-
cosyltransferases, used by cariogenic bacteria such as Streptococcus mutans to synthesise insoluble
glucans. These adhere to the tooth surface, forming dental plaque and leading to acid attack of
the enamel. Further work was planned to involve in vivo testing as a possible new natural cario-
static drug for the maintenance of oral health.
In a draft review by the Food and Drug Administration Dental Plaque Subcommittee in the
USA, a fixed combination of menthol, Eucalyptus, thymol and methyl salicylate is classified as
a Category I, safe and effective oral care ingredient. The final report was due to have been
published during 1999.
Cleaning uses
Eucalyptus oil can be used in a wide variety of ways as a cleaning agent. It is perhaps best known
in Australia as a wool wash (Chapter 7) but other applications in the home include use in carpet
shampoos, floor and general hard surface cleaning, spot and stain removal from clothes and
furniture, as a solvent for the removal of chewing gum and for general air freshening. Elsewhere,
it can be used as a leather or vinyl cleaner and for the removal of tar marks from motor vehicle
paintwork, residues from stickers, labels or sticky tape, and grease or paint from the hands (when
it will also eliminate obnoxious odours). These properties utilise the ability of cineole and other
monoterpenes to act as a solvent for other oily or greasy molecules.
A general purpose cleaner which contains Eucalyptus is included in Table 16.3.
Legislation in Europe and the United States

In Europe, E. globulus oil has to be labelled for bulk handling purposes under the Dangerous
Substances Directive (67/548/EEC) as its flashpoint is 48C and it is classified as Flammable
(R10). It is not classified for either health or environmental effects. E. citriodora oil is not classi-
fied for health, environmental or physico-chemical (flammability) effects. More detailed infor-
mation on packaging and labelling requirements for the handling and transportation of
eucalyptus oils, particularly those arising from European legislation, is provided in Appendix 6.
The situation in the United States is slightly different to that in Europe. Drums of either of
the two oils are required to be labelled for worker protection with the phrase May irritate skin
and eyes. For transportation purposes E. globulus oil is classified as a flammable liquid while,
again, E. citriodora is not classified.
At the present time, under the sixth Amendment to the European Cosmetics Directive
(96/335/EC), if either E. globulus or E. citriodora oils are used in a cosmetic product they need to
be listed as an active ingredient on the label of that product under their Linnaean name.

The European Biocidal Products Directive (98/8/EC) which is being implemented at the pre-
sent time may also have some labelling consequences for eucalyptus oils. Eucalyptus oil, in par-
ticular that from E. citriodora, is known to have insect repellent properties and repellents are
included in this legislation. The exact consequences for consumer product labelling are as yet
unclear, but it would appear that if biocidal properties are claimed for a product then the active
ingredient must be named on the label, and listed on the annexes to the directive. However,
legal opinion in Europe (Commission DGIII) is of the view that this will not affect cosmetic
products since a cosmetic product cannot be a biocidal product at the same time. In this case,
neither cosmetic products nor their ingredients will have to comply with any of the require-
ments of this directive.
The use of these oils is not regulated or restricted in consumer products in the United States.
Acknowledgements
The authors would like to acknowledge the assistance of Anthony C. Dweck of Dweck Data for
allowing us access to his database on natural plant materials and John Coppen for his compila-
tion of Tables 16.1 and 16.2.
References
Anon (1996) Taking a eucalyptus leaf out of the koalas book. Chem. Brit., 32(12), 17.
Clark, G. (2000) Eucalyptol. Perfum. Flavor., 25(May/June), 6, 810, 12, 1416.
Davis, P. (1990) Eucalyptus. In Aromatherapy, An A-Z, C.W. Daniel, Saffron Walden, UK, pp. 122124.
Ford, R.A., Letizia, C. and Api, A.M. (1988) Eucalyptus citriodora oil. Food Cosmet. Toxicol., 26, 323.
Internet (2000) Herbal Remedies. Eucalyptus: The Australian Antiseptic. www.healthyideas.com/
healing/herb/rem/971216.herb.html.
Kligman, A.M. (1966) The identification of contact allergens by human assay. III. The maximization test.
A procedure for screening and rating contact sensitizers. J. Invest. Derm., 47, 393.
Kligman, A.M. and Epstein, W. (1975) Updating the maximization test for identifying contact allergens.
Contact Dermatitis, 1, 231.
Martindale, W.H. (1910) Essential oils in relation to their antiseptic powers as determined by their carbolic
coefficients. Perfum. Essent. Oil Rec., 1, 266274.
Ody, P. (1996) Handbook of Over-the-Counter Herbal Medicines, Kyle Cathie, London.
Opdyke, D.L.J. (1975) Eucalyptol; Eucalyptus oil. Food Cosmet. Toxicol., 13, 105106; 107108.
Poucher, W.A. (1991) Pouchers Perfumes, Cosmetics and Soaps, Vol. 1, The Raw Materials of Perfumery,
Chapman & Hall, London, p. 159.
RPS (1996) Martindale, The Extra Pharmacopoeia, 31st edn, Royal Pharmaceutical Society, London.
Selected bibliography
Arctander, S. (1960) Perfume and Flavor Materials of Natural Origin, Elizabeth, USA (available from Allured
Publishing, Carol Stream, USA).
Chevallier, A. (1996) The Encyclopedia of Medicinal Plants, Dorling Kindersley, London.
CTFA (1997) International Cosmetic Ingredient Dictionary & Handbook, 7th edn, The Cosmetic, Toiletry &
Fragrance Association, Washington DC, USA.
Curtis, S. (1996) Neals Yard Remedies. Essential Oils, Aurum Press, London.
Grieve, M., A Modern Herbal, Eucalyptus, Internet at www.botanical.com.
Hill, C. (1997) The Ancient and Healing Art of Aromatherapy, Hamlyn, London.
Lawless, J. (1995) The Illustrated Encyclopedia of Essential Oils, Element Books, Shaftesbury, UK.

Leung, A.Y. and Foster, S. (1996) Encyclopedia of Common Natural Ingredients Used in Food, Drugs and
Cosmetics, John Wiley & Sons, USA.
Miller, L. and Miller, B. (1995) Ayurveda and Aromatherapy, Lotus Press, USA.
Ody, P. (1997) 100 Great Natural Remedies, Kyle Cathie, London.
Wells, F.V. and Billot, M. (1981) Perfumery Technology: Art, Science, Industry, Ellis Horwood, Chichester, UK.

17 Production, trade and markets for
eucalyptus oils
John J.W. Coppen
Introduction
The botanical, chemical, genetic and other aspects of oil-bearing eucalypts are discussed in detail
elsewhere in this volume, as are the uses and types of formulations of eucalyptus oil. It is
intended, here, to examine the production, trade and markets for the oil. With the possible
exception of rutin, for which little or no information on trade and markets to the extent that
trade exists is available, the volatile oil is the only aromatic/medicinal product of eucalyptus
around which has been built an industry of any size. Some of the non-volatile constituents have
considerable potential in the pharmaceutical and related fields but their utilisation in this way
is, as yet, some way off from commercial realisation. Eucalyptus oil, on the other hand, is one of
the largest volume and most widely used essential oils, produced in many parts of the world and
on widely differing scales. It is a well established article of commerce and for many countries a
valuable source of foreign exchange.
The different types of eucalyptus oil, and the species from which they are obtained commer-
cially, are first summarised. For each of the major producing countries or regions, production is
then described briefly in terms of locations and species utilised other chapters have dealt with
the subject in greater depth but some description is necessary to facilitate the rest of the discus-
sion. Where possible, the levels of production are quantified and trade statistics are used to indi-
cate the scale and directions of international trade. Price trends are then examined in some detail
and, finally, some remarks are made on the outlook for the industry.
Principal sources and uses of eucalyptus oil
Plant sources
Eucalyptus oils are clear liquids with aromas characteristic of the particular species from which
they are obtained. The oils are colourless when refined but usually slightly yellow when first dis-
tilled from the leaf. The composition of the oil, and therefore its olfactory and other properties,
is dependent, mainly, on genetic rather than environmental factors. The species of Eucalyptus
from which the oil is obtained is, therefore, the most important factor determining its composi-
tion and quality and the use, if any, to which it is put.
Of the hundreds of species of Eucalyptus that have been shown to contain volatile oil in their
leaves, probably fewer than twenty of these have ever been exploited commercially for eucalyptus
oil production. About a dozen species are presently utilised in different parts of the world, of which
six account for the greater part of world oil production: E. globulus, E. exserta, E. polybractea,
E. smithii, E. citriodora and E. dives (piperitone variant). The oils are conveniently classified

Table 17.1 Commercial sources of eucalyptus oil: main species and countries of
productiona
Species Producing country
Medicinal
E. globulusb China, Portugal, Spain, India, Brazil, Chile
E. exsertac China
E. polybractea Australia
E. smithii South Africa
E. radiatad South Africa, Australia
Perfumery
E. citriodora China, Brazil, India
E. staigeriana Brazil
Industrial e
E. dives (piperitone variant) South Africa
E. olida Australia
a Oils from a few species listed here (E. radiata, E. staigeriana and E. olida) are produced in
much smaller quantities than others. Some other species, such as E. dives (cineole variant),
E. viridis and E. camaldulensis are exploited commercially but only intermittently and/or on a
small scale and are not listed. Small producers such as Bolivia, Paraguay and Uruguay are also
not listed.
b Mainly subsp. globulus but including subsp. maidenii in China.
c Includes E. leizhou No. 1, a local land-race in China considered to be a natural hybrid of
E. exserta.
d Still sometimes referred to in commerce as E. australiana or E. radiata var. australiana.
e Both E. dives and E. olida oils (or their constituents) are used for fragrance purposes so could
alternatively be regarded as perfumery oils.
according to their composition and/or main end-use: medicinal (cineole-rich), perfumery and
industrial. Of these, the most important in volume terms is the medicinal type.
The main species currently exploited for oil, and the countries where this occurs, are listed in
Table 17.1. Note that there are some other species and countries which are not listed because oil
production is only intermittent and/or on a small scale. E. globulus is the principal species and is
often the one against which others are judged in terms of quality (cineole content) and produc-
tivity. E. cneorifolia (medicinal), E. macarthurii (perfumery) and E. radiata (phellandrene variant;
industrial) have been used in the past. E. cinerea oil (medicinal) was produced on a small scale in
Zimbabwe in the early 1990s but its present status is not known. Western Australian species
such as E. kochii and others may come to be exploited as a source of eucalyptus oil on a massive
scale in Australia in the future (see below) but at the present time this remains speculative.
Medicinal oils
Present uses
The medicinal properties of eucalyptus oil were known to the aborigines of Australia thousands
of years ago, but were first exploited commercially by Bosisto. He began production in Australia
in 1852, extolling the oils virtues for the treatment of a wide range of ailments. Since then,
medicinal eucalyptus oil has remained the most important of the three types of oil, although
Australia is no longer the dominant producer that it was.
The value of eucalyptus oil for medicinal purposes lies in its cineole content (strictly, 1,8-cineole,
to distinguish it from the alternative 1,4-cineole, but the term cineole is commonly applied to

the former and is used here). This largely determines, also, the price that it fetches. While many
other essential oils are referred to simply by name in the trade or in manufacturers or dealers
product and price lists, medicinal eucalyptus oil is invariably specified in terms of cineole con-
tent. Eucalyptus oil China 80 per cent and eucalyptus oil 70/75 per cent (or 80/85 per cent)
Spain/Portugal are typical descriptions. The higher grades are usually rectified forms of the
crude oil. Essentially pure cineole (about 98 per cent!), which commands the highest price, is
known as eucalyptol. The general norm for cineole content, typified by the international stan-
dard (ISO) for oil of Eucalyptus globulus and the British Pharmacopoeia specification for euca-
lyptus oil is a minimum of 70 per cent (see Appendix 5). Any species of Eucalyptus which yields
an oil with less than about 6065 per cent cineole in the crude oil is unlikely to be of interest to
a buyer or rectifier of such oils.
Providing a medicinal oil satisfies the appropriate pharmacopoeial requirements it may be
sold as such, neat, in pharmacies and other retail outlets. In the home, eucalyptus oil is used in
liquid form in a variety of ways, either medicinally or as a disinfectant, cleaner or deodoriser
about the house. More commonly the oil is formulated before sale and used in the form of sprays,
lozenges, ointments or other, compound oils or solutions (see Chapter 16). Although termed
medicinal oils, the fragrant properties of cineole-rich oils also make them attractive to use in
certain soaps and bath oils.
Possible future uses

Research has also been carried out on other non-medicinal uses of cineole-containing eucalyptus
oils. In Australia and Japan the use of such oils as fuel additives for petrolalcohol mixtures has
been explored but to date there has been no widespread application of this nature.
More recently, research has been undertaken in Western Australia which has far-reaching
implications for eucalyptus oil supply and consumption if the potential indicated by the results
to date is realised. Trials in the early 1990s (see e.g. Eastham et al. 1993) aimed at utilising
Eucalyptus to combat the problem of soil salinity in the wheatbelt of Western Australia were suf-
ficiently promising that a long-term programme of research and development was formulated.
Any perennial planted on a sufficiently large scale to have any prospect of combating salinity
would need to pay its way in terms of cash return. Work coordinated by the Western Australian
Department of Conservation and Land Management (CALM) has shown that if native eucalypts
of the mallee type (multi-stem eucalypts which are amenable to coppicing, such as E. kochii)
were planted, they could be repeatedly harvested and processed in an integrated manner to
produce activated carbon, renewable energy and eucalyptus oil (RIRDC 1999). By mid-2000
some 17 million seedlings had been planted and a demonstration-scale plant was about to be
constructed to undertake processing trials ( J. Bartle pers. comm.). The extent of revegetation
required to have an impact on salinity can be measured in millions of hectares and this inevitably
means large-volume markets for the products. For eucalyptus oil the existing medicinal markets
would be insufficient to absorb the large volumes produced and a new market became the
focus of attention: industrial solvents (Bartle et al. 1996, Bartle 1999). In particular, it is
aimed to replace, at least partially, the environmentally damaging 1,1,1-trichloroethane with
environmentally friendly cineole-rich eucalyptus oil. Before its production was discontinued
in 1996 under international convention, around 700,000 t of trichloroethane were produced
annually. CALM believes that eucalyptus oil has the opportunity to enter the market as a
suitable, natural replacement product. Even just 1 per cent of the market would require
7000 t of eucalyptus oil, around twice the size of the present worldwide consumption of
cineole-type oil.

Perfumery oils
Of the two perfumery oils listed in Table 17.1, that from E. citriodora is produced in the greatest
volume. It contains citronellal as the major component usually about 6585 per cent and is
employed in whole form for fragrance purposes, usually in the lower-cost soaps, perfumes and
disinfectants. However, it is also used as a source of citronellal for the chemical industry. The cit-
ronellal obtained by fractionation of the crude oil is then employed as such as an aroma chemical
or converted to hydroxycitronellal. The latter compound finds major usage as a perfumery mate-
rial. Other, minor, constituents of the oil, such as citronellol, are recovered during fractionation
for subsequent use by the fragrance industry.
Both citronellal and the derived hydroxycitronellal are produced from two other sources,
citronella oil and turpentine. To some extent, therefore, there is competition between these
sources and E. citriodora oil. Price and slight odour differences caused by accompanying minor
constituents in the chemical isolates determine customer preference. Natural citronellal
derived from eucalyptus or citronella oils may have some marketing advantages over synthetic,
turpentine-derived citronellal in flavour applications.
E. staigeriana oil, produced only in Brazil, is utilised solely in whole form for fragrance pur-
poses. It has a lemon-type character. No single chemical predominates as it does in most other
commercial eucalyptus oils, although limonene and the higher-boiling citral (neral!geranial)
together account for about 5060 per cent of the total terpenes (see Appendix 4).
Oil from E. macarthurii is a rich source of geranyl acetate but has only ever been available in
very small quantities and appears no longer to be produced.
Industrial oils
The term industrial is usually used to indicate that the oil is employed as a source of chemical
isolate(s), that is, one or more constituents of the oil is isolated by a process of fractionation or
some other means and then used in its own right for some application or further processed into
marketable derivatives. (In this sense, E. citriodora oil might be considered an industrial oil if it
is used as a source of citronellal). However, if cineole-rich oil were to be produced on a very large
scale for use as an industrial solvent, as discussed above, common parlance would probably
ensure that this, too, was referred to as an industrial oil.
The piperitone variant of E. dives yields an oil rich in piperitone and phellandrene. Since
the mid-1960s, most of the worlds supply of this oil has originated in South Africa and, until
the early 1990s, much of it was shipped to Australia for fractionation. The lower boiling
phellandrene fraction (comprising "-phellandrene and other monoterpenes) was recovered
and sold, mainly for use as a cheap fragrance source, while the piperitone (which accounts for
about 40 per cent of the oil) was recovered for use as a starting material for the production of
menthol, a major flavour ingredient. Although this route to menthol was in competition with
natural menthol obtained directly from Japanese mint (Mentha arvensis) and that obtained
synthetically from petroleum-based raw materials, and is no longer used, some fractionation
does still occur.
Oil distilled from the leaf of E. olida (originally referred to as Eucalyptus sp. nov. aff. campanulata)
contains about 98 per cent E-methyl cinnamate, a chemical used as a flavour and fragrance mate-
rial. Commercial production began in Australia in the late 1980s and to date this remains the
sole source. Given the relatively small market for E-methyl cinnamate this is likely to remain
the case for the foreseeable future.

Production, consumption and trade by country/region
Introduction
Any attempt to accurately quantify and analyse production and consumption trends for eucalyptus
oil is fraught with difficulties. Unlike some of the larger commodities, or some other essential
oils such as the citrus oils, quantitative information is not always available or accessible. Where
data are available their accuracy and reliability have to be judged as best one can. There are,
fortunately, some published trade statistics and this gives some cause for optimism that one can,
at least, be talking within the right orders of magnitude. The finer detail is less certain. Trade
statistics may identify importing countries but if these same countries are also processors and/or
re-exporters then it is difficult to quantify actual consumption in geographical terms. The same
is true of producing countries: since production data are rarely available, any export statistics
will give no clues as to domestic consumption. Chinas exports of eucalyptus oil are
discussed below but their own, internal consumption can only be guessed at. And trade statistics
for eucalyptus oil say nothing about the trade in formulated products containing eucalyptus oil.
Nevertheless, and in the face of these deficiencies, some useful observations can be made.
Before examining published trade statistics some further words of caution on their use and inter-
pretation are appropriate. Firstly, the data are only as good as the customs returns allow. That is
to say, if the exporter chooses not to describe his shipment as eucalyptus oil for whatever
reason then it clearly will not be recorded as such and the official returns will underestimate
exports. Occasionally, items are misnamed by the shipper or misclassified by the customs, which
can result in either inflated or deflated figures. Small quantities of eucalyptus oil of Indonesian
origin, for example, which appear in some countries import statistics are probably cajeput oil
(from Melaleuca) rather than eucalyptus oil.
Secondly, items of trade are not always separately specified in the statistics of the country con-
cerned. In all systems of customs classification, a numbering hierarchy groups commodities
according to type and becomes increasingly more specific as the number of digits increases.1 If
the commodity is a major item then it usually specified, but otherwise it is included with simi-
lar commodities under a general heading. Unfortunately, this is often the case for eucalyptus oil
and although, thankfully, China lists it separately, many other countries or regions simply
include it in the all-embracing essential oils or under an essential oils, not elsewhere specified
(NES) heading. Amongst the importing countries, Japan groups eucalyptus oil with fifteen
other oils under a single essential oil heading and Hong Kong and Singapore, important inter-
mediate destinations for Chinese eucalyptus oil, include it with other essential oils. In these
circumstances, if the essential oil(s) coming from any of the countries of origin listed can reasonably
be expected to be solely or mainly eucalyptus oil then it may be possible to draw some tentative
conclusions. Thus if the figures given in Table 17.2 which shows imports of essential oils into
Japan for the period 19921999 and the contributions of three eucalyptus oil producers to these
imports are reliable, an upper limit of between 2 and 7 t annually can be put on imports of
Australian eucalyptus oil. These figures are close to the levels of exports of eucalyptus oil from
1 Most countries now use the Harmonised Commodity Description and Coding System (usually known simply as the
Harmonised System) of the Customs Cooperation Council. A few countries show the SITC number (Standard
International Trade Classification, Revision 3) of the United Nations alongside the HS number. For eucalyptus oil the
HS number is usually 330129xx (where xx is e.g. 60 for China, 10 for the USA and 14 for India). The SITC number,
if it is used, is of the form 5513xxx.

Table 17.2 Volume of imports of essential oilsa into Japan, showing quantities from
China, Spain and Australia, 19921999
1992 1993 1994 1995 1996 1997 1998 1999
Total (t) 220 237 168 192 184 166 131 149
Of which from
China 50 64 61 55 61 55 33 61
Spain 37 28 37 28 29 32 31 34
Australia 5 2 4 4 5 6 7 4
Source: National statistics.

a Defined as Essential oils (bay leaf, cananga, citronella, eucalyptus, fennel, star anise, petit-grain,
rosemary, rosewood, ylangylang, cinnamon leaf, ginger grass, palmerosa, thyme, gyusho and
lemongrass oils).
Australia to Japan for the earlier period 1982/831989/90 (Coppen and Hone 1992) and the
more recent period 19972000 (Table 17.7, below). In the case of imports into Japan from
China and Spain, eucalyptus oil may well fall within the upper limits indicated in Table 17.2
but it would be unwise to speculate as to exactly how much might represent eucalyptus oil.
Since 1993, European Union statistics (Eurostat), which previously listed eucalyptus oil
separately, have not done so. In this case, fortunately, a reasonable picture of the relative impor-
tance of the member states as importers of eucalyptus oil can be gained from the Chinese export
statistics and this is discussed in more detail below. Of the other producing and exporting coun-
tries, South Africa does not separate eucalyptus oil from other essential oils and neither do the
smaller South American producers such as Paraguay.
Finally, with the exception of export data for China up to 1994 which separates E. citriodora
oil from other types of eucalyptus oil (see below) no distinction is made in trade statistics
between different botanical sources of the oil.
Peoples Republic of China

Eucalyptus has been planted extensively in southern areas of China, almost 1 million ha in all.
Around 150,000 ha of E. globulus (mainly subsp. globulus but also subsp. maidenii) occur in the
south-western area, mainly in Yunnan province, and this is the chief source of Chinese eucalyp-
tus oil. The main producing regions in Yunnan are Dali, Kunming and Chuxiong in the north
of the province. E. globulus is also grown in southern Sichuan province and parts of Guangxi and
Guangdong. China is the worlds largest supplier of E. citriodora oil and this, as well as E. exserta
oil, is produced from plantations growing in Guangxi and Guangdong; additional sources are
the Leizhou Peninsula and Hainan Island. The potential of E. smithii as a dual-purpose crop oil
and fuelwood is being recognised (see Chapter 8) and this species may begin to be utilised as a
source of oil in the future, as it already is in South Africa (see below).
Opinion is divided on how much so-called Chinese eucalyptus oil is derived genuinely from
Eucalyptus and how much is ex camphor. The camphor tree, Cinnamomum camphora, yields an oil
which, on fractionation, furnishes a cineole-rich fraction (Coppen 1995). This material is diffi-
cult to distinguish chemically from genuine eucalyptus oil, although it has a different odour and
is excluded from most direct pharmaceutical use outside China by virtue of its slightly negative
optical rotation.2 In the recent past it has been suggested that C. camphora has been over-logged
2 The British and European Pharmacopoeias, for example, stipulate an optical rotation range of 0 to !10. Eucalyptus
oil ex camphor, however, is explicitly allowed in the Chinese Pharmacopoeia (see Appendix 5).

and is no longer used as a source of medicinal eucalyptus oil but trade sources continue to assert
that it is. In China, eucalyptus oil ex camphor is used primarily as a feedstock for eucalyptol
production.
The scale and great geographical spread of oil production in China makes it exceedingly
difficult to quantify it with any accuracy. Wang and Green (1990) put annual production of all
types of eucalyptus oil at about 3000 t and this is usually the sort of level (sometimes up to
3500 t) that is cited by other sources in the literature or in the trade. The authors also stated that
over 1000 t of oil were exported. However, Chen (Chapter 8) puts the figure for production
much higher, at 4000 t, of which about 80 per cent (i.e. 3200 t) is exported. Sewell (1998) states
that production of cineole oil varied between about 2000 and 4000 t annually in the early and
mid-1990s, a very wide variation. He also estimated production of E. citriodora oil during the
same period to have been in excess of 1000 t/year.
Table 17.3 shows officially reported exports of eucalyptus oil from China in volume, value and
unit value terms for the period 19912000. The rising trend in exports through the 1980s
(Chapter 8) continued into the early 1990s (Table 17.3) and peaked in 1994 (at 4400 t). For the
years 1991 and 19932000, annual exports averaged just under 3600 t. These figures are in line
with those put forward by Chen (Chapter 8). Exports were valued at US $15.2 million in 1995;
the higher volume of exports in 1994 was offset in value terms by the lower average price. Care
must be taken in using the export data in Table 17.3 to assess levels of imports of Chinese oil
into the destination countries shown considerable quantities are shipped to Hong Kong (not
re-integrated with the Peoples Republic of China until 1997), Singapore and Taiwan but almost
all of this is re-exported (often, in the case of Singapore and Taiwan, as eucalyptol). For 1991,
where the split between E. citriodora oil and other eucalyptus oil is known (see footnote to
Table 17.3), France can be seen to have taken a higher proportion of the perfumery oil, while the
other destinations took, largely, the cineole oil.
Table 17.4 cites data from another official source which separates E. citriodora oil from euca-
lyptus oil. Where it is possible to compare years in Tables 17.3 and 17.4, it can be seen that
total volumes for 1991 are similar, those for 1993 and 1994 in Table 17.3 appear to exclude the
quantities of E. citriodora oil shown in Table 17.4, and those for 1995 and 1996 are identical for
both Tables. It is not clear, therefore, even using official statistics, as to whether the term euca-
lyptus oil is all-inclusive. Whatever the truth it seems likely that, firstly, exports of E. citriodora
oil have been between 450 t and about 750 t annually and, secondly, since 1993 exports of euca-
lyptus oil (all types) have been at least around 3500 t/year and they may have been significantly
higher, that is, in accordance with the estimates for production and exports of Chen (Chapter 8).
Outside of China, Vietnam is the only other Southeast Asian (mainland) producer of eucalyptus
oil although, of course, on a much smaller scale. Sewell (1998) put production as high as 250 t
in 1990.
United States (consumption)

In the absence of recent data for member states of the European Union, it is not possible to know
whether the United States is the biggest single market for eucalyptus oil. France, Germany and
Spain all imported more than the USA in the early 1990s (see below) and are undoubtedly still
major importers but all four countries process and re-export eucalyptus oil. It is likely that in
terms of actual consumption the USA is the largest consumer but that one or more of the EU
countries remain(s) the biggest primary destination(s). The volume, value and unit value of
imports of eucalyptus oil into the USA, with origins, for the period 19912000 are shown in
Table 17.5.

Table 17.3 Volume, value and unit value of exports of eucalyptus oil from China, and destinations, 19912000a
1991 1992 1993 1994 1995 1996 1997 1998 1999 2000
Volume (t) 3159b nsc 3414 4420 3858 3659 3690 2811 3784 3449
Value 14,784 ns 9247 10,107 15,215 12,893 12,197 9916 11,468 12,986
(000 US $)
Unit value 4.68 ns 2.71 2.29 3.94 3.52 3.31 3.53 3.03 3.77
(US $/kg)
Of which to (t)
Hong Kong 1444b ns 1031 1445 1321 1432 1133 381 217 377
Singapore 358 ns 609 692 651 456 77 106 183 119
Taiwan d ns 63 205 223 287 43 218 138
Japan 5b ns 16 11 15 29 32 7 15 11
Thailand 17 ns 26 11 25 27 33 45 26 28
Indonesia ns 3 11 63 46 324 387
Malaysia 5 ns 3 29 11 5 12
Vietnam ns 28 7 14 3 3
Philippines ns 4 10 4 6 25 11
Australia 118 ns 84 140 158 70 170 192 196 266
India ns 14 71 46 160 87 353 74
Pakistan 10 ns 13 13 4 5 4 12 20 15
Sri Lanka ns 1 1 4 3 3
Bangladesh ns 1 4 2 5 4
France 454b ns 302 408 227 153 486 399 391 399
Germany 261b ns 394 325 325 186 166 379 540 339
UK 135 ns 298 332 385 374 324 245 421 399
Spain 122b ns 74 331 139 331 181 221 251 302
Netherlands 53b ns 86 134 164 81 74 73 122 154
Switzerland 5 ns 11 11 19 19 72 38 8
Italy 9 ns 3 8 15 14 24 14
Portugal ns 14 58 115
Denmark ns 11 2 6 6 2 2 18 12
Sweden 1 ns 1 1 1 1 1
South Africa ns 3 4 5
USA 153b ns 360 347 166 203 292 358 395 343
Canada ns 18 3 4 7 22 8
Mexico ns 7 7 7 15
Argentina 5 ns 17 14 14 29 14
Others 4 ns 8 6 7 1 3 1 7
Source: China Customs Statistics Year Book.

a For 1991, source data separate Eucalyptus oil and Eucalyptus citriodora oil but these are combined here. For 19931997,
source data are described as Essential oils of eucalyptus.
b Of which E. citriodora oil represents (t) 619 (total), 209 (Hong Kong), 1 ( Japan), 303 (France), 16 (Germany), 35 (Spain),
21 (Netherlands) and 34 (USA).
c Eucalyptus oil not specified separately.
d Indicates that country not recorded (so assumed to be nil or negligible).
Imports rose year-on-year from 1991 to 1995 and then followed a sequence of peaks and
troughs in the second half of the decade; in 1998 and 2000 imports reached just over 700 t/year
(valued at US $3.2 and US $2.9 million, respectively). Imports averaged 510 t/year over the
whole period (cf. 325 t/year for 19831990; Coppen and Hone 1992).
China is clearly seen to be the main source of US imports of eucalyptus oil but Brazil has also
been a consistent, albeit much smaller, supplier. Of the other primary producers, Australia and
South Africa have been the most important.

Table 17.4 Volume, value and unit value of exports of eucalyptus oil from China, 19891996a
1989 1990 1991 1992 1993 1994 1995 1996
Eucalyptus oil
Volume (t) 1344 2354 2521 2654 3316 4482 3858 3659
Value (000 US $) 9560 13,026 12,763 10,781 9651 11,309 15,215 12,893
Unit value (US $/kg) 7.11 5.53 5.06 4.06 2.91 2.52 3.94 3.52
E. citriodora oil
Volume (t) 451 454 459 505 780 744b nsc ns
Value (000 US $) 1410 1260 1792 2046 2508 2432 ns ns
Unit value (US $/kg) 3.13 2.78 3.90 4.05 3.22 3.27 ns ns
Source: Almanac of Chinas Foreign Economic Relations and Trade.

a For 19891994, eucalyptus oil and Eucalyptus citriodora oil are listed separately under Essential oils. For 1995
and 1996, eucalyptus oil is described as Eucalyptus oil, natural and E. citriodora oil is no longer listed separately.
b Source data show figure of 9744 which cannot be right; it is assumed here that correct figure should be 744,
which is consistent with the value figure.
c Not specified separately.
Table 17.5 Volume, value and unit value of imports of eucalyptus oil into the USA, and origins, 19912000
1991 1992 1993 1994 1995 1996 1997 1998 1999 2000
Volume (t) 326 347 454 478 504 402 604 704 576 707
Value 1709 1583 1859 1407 2582 1931 2591 3161 2261 2909
(000 US $)
Unit value 5.24 4.56 4.09 2.94 5.12 4.80 4.29 4.49 3.93 4.11
(US $/kg)
Of which from (t)
China 222 268 386 389 387 306 452 485 482 466
Hong Kong 18 a 14 3 4 5
Singapore 2 13
Taiwan 32 1 5 26 21 7 55
Indonesia 4 2 15
Australia 3 16 4 7 10 16 2 1 12 74
India 4 20
France 1 2 7 7 26 4 7 4 3 4
UK 5 8 10 8 14 1 2 12 10
Germany 3 6 6 8 5 1 10 11
Spain 2 6 13
Switzerland 15 7 1 12
South Africa 14 12 19 7 9 9 1
Swaziland 7
Canada 1 2 2
Jamaica 6 5 1 3 4 3 2 8 8
Brazil 3 22 14 28 33 38 82 138 18 80
Chile 2 2 3
Paraguay 5 5 9
Guatemala 4
Bolivia 1
Others 2 2 1 5 2
Source: US Department of Commerce, Bureau of Census. Provided by Global Trade Information Services, Inc.
a Indicates nil or negligible.

European Union (consumption)
Imports of eucalyptus oil into the European Union from 1990 to 1992, the last year for which
eucalyptus oil is reported separately, are shown in Table 17.6. Origins and destinations within
the EU are also shown. Total imports averaged just over 2600 t/year (cf. just under 1800 t/year in
the period 19831990; Coppen and Hone 1992).
As expected, China is by far the biggest supplier but South Africa is notable amongst the
other producing countries. France, Germany, Spain and the UK are the biggest importers but all
are processors, blenders and re-exporters. This introduces yet another difficulty in properly
interpreting the statistics because there will be a measure of double counting imports into
Table 17.6 Volume of imports of eucalyptus oil into

the European Union, and origins and
destinations, 19901992
1990 1991 1992
Total (t) 2643 2382 2853

Of which from (t)
China 1794 1784 2070
Hong Kong 47 66 47
Singapore 1 9 5
Australia 10 12 8
India 57 5
Sri Lanka a 4 1
South Africa 164 127 176
Swaziland 15
Namibia 21
Zimbabwe 2
USA 20 5 2
Brazil 31 23 34
Paraguay 6
Chile 1 9
Spain 175 128 210
Portugal 117 66 106
UK 78 37 106
Germany 40 52 44
France 35 31 17
Netherlands 29 18 24
Italy 1 2
Belgium/Lux. 2
Switzerland 1 1 1
Total (t) 2643 2382 2853
Of which to (t)
France 863 750 723
Germany 542 627 701
Spain 529 499 717
UK 432 285 440
Netherlands 108 90 79
Portugal 41 16 61
Denmark 22 22 16
Ireland 1 4 5
Greece 1 2
Source: Eurostat.
a Indicates nil.

France from, say, China which are processed and then re-exported to other countries within the
EU in the same year will be counted twice. Imports into the EU from EU countries accounted
for between 14 and 18 per cent of total imports for the years 19901992.
The levels of direct imports into the EU countries from China during 19912000 can be seen
from Table 17.3 but, as noted earlier, it is impossible to know how much more Chinese eucalyp-
tus oil is going into them via Hong Kong and Singapore. The most one can say is that the
figures for the main EU countries are under-estimates, especially so for the years prior to 1998.
Portugal and Spain

In Portugal, very large areas of eucalypts exist, distributed mainly along the Atlantic coast north
of Lisbon and the Tagus valley. The vast majority, and sole source of oil, is E. globulus, all of
which has been planted to meet the needs of the large domestic pulp industry. The main con-
centrations of eucalypt plantings in Spain are in the south of the country, in the forests of
Huelva, where the main species is again E. globulus. In both cases, oil production is from the
waste leaf remaining after the trees have been felled. The main distillery groups, in addition to
producing crude oil themselves, buy oil from a number of small, independent distilleries.
At the beginning of the 1990s, Coppen and Hone (1992) estimated that annual production in
Portugal and Spain was around 150200 and 50 t or less, respectively, but on a declining trend.
The fall in output was a result of rising labour costs and severe competition from low-priced
Chinese oil. This trend has continued and although both Spain and Portugal remain exporters of
eucalyptus oil products, including eucalyptol (1,8-cineole), much of the starting oil is imported
from China and elsewhere. For the three years 19901992, Spanish imports of Chinese oil
averaged 470 t/year (out of total average imports of 580 t, Table 17.6). Present indigenous
production is probably less than 100 t/year for Portugal and Spain combined (and could be as
little as 50 t).
Australia
After the development of large-scale commercial operations during the latter part of the nine-
teenth century, Australian production of eucalyptus oil reached a peak in the 1940s and has since
declined. However, in the face of increasing production elsewhere in the world, the introduction
of mechanised harvesting enabled the Australian industry to become more efficient and it has
consolidated in two main geographical areas: near West Wyalong, New South Wales, and the
Inglewood area of Victoria. In both cases, cleaned natural stands of E. polybractea, a high quality
source of cineole-rich medicinal oil, are utilised, complemented by smaller areas of plantation.
Some oil is produced by independent distillers from species such as E. radiata and E. dives out-
side of these two regions but it is neither substantial nor regular. In the last decade, small
plantations of E. olida have been established to meet demand for natural E-methyl cinnamate;
production is probably no more than 10 t/year.
Domestic production of cineole oil is around 100 t/year or less; McKelvie et al. (1994) put it
at around 80 t/year. However, it is supplemented by imports of lower quality oils, particularly
from China, which are rectified and then blended with locally produced oils. Much of the subse-
quent re-exports are in the form of the final, formulated product, rather than the whole oil. If the
Chinese trade statistics are accurate, Australian imports of eucalyptus oil averaged 155 t/year for
the years 1991 and 19932000 (Table 17.3) with a rising trend. Additional quantities of
Chinese oil may be imported via Hong Kong and Singapore. Piperitone-containing E. dives oil is
no longer imported from South Africa, as it used to be, for menthol production.

Table 17.7 Volume of exports of eucalyptus oil from Australia,
and destinations, 19972000
1997 1998 1999 2000
Total (t) 121 93 91 147

Of which to
New Zealand 5 8 12 17
Thailand 29 5 13 21
Malaysia 3 6 10 7
Indonesia a 5
Singapore 6 13 17 11
Hong Kong 6 5 8 6
Japan 6 7 4 9
South Korea 1 1
Sri Lanka 1
Germany 36 31 7
UK 10 3 1 6
Netherlands 2 1 3 6
Belgium/Lux. 2 1
France 1 3
Spain 1
Poland 2
Russia 9
USA 11 4 18 33
Canada 2 1 11
Source: Global Trade Information Services, Inc.

a Indicates nil or negligible.
Recent Australian exports (19972000) are shown in Table 17.7. They averaged 113 t/year
and apart from North America and Europe, regional destinations, as one would expect, are seen
to be important.
The plans to produce very large quantities of cineole-rich oil in Western Australia have
already been referred to. If the plans come to fruition, eventual oil production in Australia would
exceed that of China.
Africa
Southern Africa remains a significant producing region for eucalyptus oil although it has
declined in both size and diversity since the report of Coppen and Hone (1992). Production now
rests almost entirely with South Africa. Swaziland, previously a significant producer of oil
mainly the medicinal type from short-rotation, coppiced E. smithii effectively ceased produc-
tion when the principal company involved decided to concentrate on its more profitable timber
operations. Previously, some 7080 t of oil were produced annually, most of which was exported
to Australia for rectification and blending. Zimbabwean production began in 1989 and only
ever amounted to around 10 t of oil annually, mostly from coppiced E. smithii but a little from
E. cinerea. Prevailing low prices for the oil made the operation very marginal economically and it
is believed, though not certain, that production has ceased.
With the exception of a small quantity of medicinal oil produced from E. radiata in Cape
Province, South African oil production is centred in the eastern Transvaal, close to the border
with Swaziland. Although large areas of E. smithii have been planted in the south-eastern

Transvaal and Natal for timber purposes, and could be utilised for oil production if there were a
wish to do so, existing production of oil from this species is derived almost entirely from short-
rotation, coppiced trees in which oil is the sole product. In the late 1980s/early 1990s, produc-
tion volume was split approximately equally between E. smithii and E. dives (piperitone type):
150180 t annually each species (Coppen and Hone 1992). Since then, the industry has con-
tracted. Although E. dives oil is no longer used for menthol production, with consequent loss of
the Australian market for this purpose, it continues to be exported for use in flavour and fra-
grance manufacture, mainly to France and Germany. The greatest decline has been in the area
given over to production of cineole-rich oil, under pressure from competing, low-priced oil from
China. One South African source has put the production split at about 1 : 2 for cineole : piperi-
tone-type oils, representing approximately 135 t of cineole oil and 200 t of E. dives oil annually
(V. Davidson pers. comm. 1998). The figure for cineole oil is divided between E. smithii (100 t)
and E. radiata (35 t). However, another estimate has put annual oil production at around 3050 t
(E. smithii) and 100120 t (E. dives) (C. Teubes pers. comm. 1998).
For the years 19901992, imports of South African eucalyptus oil into the European Union
averaged 155 t/year (Table 17.6) with France, Germany, Spain and the UK as the main (but
irregular) destinations. During the 1980s, France and Spain were the main EU destinations
while imports into Australia (including those from Swaziland) consistently exceeded 100 t/year
(Coppen and Hone 1992). The USA has been a small but fairly regular destination for South
African eucalyptus oil, importing (with a few exceptions) between 5 and 15 t throughout the
1980s and 1990s (Coppen and Hone 1992 and Table 17.5); imports were, however, nil or small
in the period 19982000.
Most of the E. radiata and E. dives oils produced are exported but the E. smithii oil at least,
much of it is rectified locally for domestic consumption. E. dives oil is occasionally rectified:
the phellandrene fraction is exported and the piperitone used locally. In order to meet increasing
demand in domestic markets, South Africa also imports Chinese oil (80 per cent cineole) for
compounding a variety of fragrance and flavour materials.
Outside of Southern Africa, the Democratic Republic of the Congo (formerly Zaire) once
produced small amounts of oil but no longer does so. Recent research on oil-yielding eucalypts
in several of the Francophone countries of West and Central Africa (such as Benin, the Congo,
Rwanda and Burundi) has indicated a desire to utilise for oil production those species already
planted for afforestation, fuelwood and other purposes. However, at this stage, the commercial
production of oil from such sources remains speculative.
South America
Brazil has about 3 million ha of eucalypts but most of this is not of oil-bearing species.
Nevertheless, it produces significant quantities of eucalyptus oil, particularly E. citriodora oil.
Production takes place in the states of So Paulo, Minas Gerais, Bahia and Mato Grosso do Sul.
Leaf is harvested either from trees grown specifically for oil on a coppice system, or by collection
as waste leaf from plantations established for other purposes (for the production of charcoal for
use by the steel industry, for example). Oil is also produced from E. globulus and, to a lesser
extent, E. staigeriana (for which Brazil is the only source). Brazil is by far the largest producer of
eucalyptus oil in South America.
Brazilian production of eucalyptus oil is difficult to quantify. Coppen and Hone (1992) esti-
mated E. citriodora oil, the major production, to be 400600 t/year at the beginning of the
1990s. Much less cineole oil and perfumery oil from E. staigeriana is produced, possibly around

50 t/year or less of each. However, a more recent estimate put production of all oils at 750 t in
1985 and 970 t in 1996 (L. Couto pers. comm. 1999).
Brazil has a large domestic market for eucalyptus oil but there is still a surplus for export:
annual exports averaged 215 t in the period 19831990 (Coppen and Hone 1992) and 195 t for
the years 19922000 (Table 17.8). Levels of exports during the latter period were characterised
by a trough in the middle years (19941996) followed by an upward trend to 2000. For the
years for which a breakdown of destinations is available (19972000), the nearby markets of the
USA, Mexico and Colombia have been important (though Mexico and Colombia less so towards
the end of the period). Further afield, Spain and Sweden have been consistent importers but the
UK, France and the Netherlands imported significant quantities of Brazilian oil in 2000.
Shipments to Spain reflect more its position as a fractionator/processor of oils than a consumer,
and the need to maintain a viable feedstock for this purpose, from whatever sources are available.
Although a net exporter, Brazil also imports eucalyptus oil and these imports averaged 70 t
annually for 19921999.
Elsewhere in South America, Chile, Bolivia, Paraguay, Uruguay and Colombia have all pro-
duced oil at one time or other but on a very much smaller scale than Brazil. Sewell (1998) states
that in the mid-1990s annual production of cineole-rich oil was 20 t in each of Bolivia, Uruguay
and Colombia and 25 t in Paraguay; the source of this information is not given. Chile emerged
as a modest producer of eucalyptus oil in the mid-1980s, using stands of E. globulus which is
widely planted. The main areas of E. globulus are in the Valparaiso and Bio-Bio Administrative
Regions in the centre of the country. Annual production was about 80100 t in the early 1990s,
most of which was exported, either as the whole oil or in the form of purified 1,8-cineole. Bolivia
began production of cineole-rich oil from E. globulus in the 1980s but this has been on a very
Table 17.8 Volume of exports of eucalyptus oil from Brazil, and destinations, 19922000
1992 1993 1994 1995 1996 1997 1998 1999 2000
Total (t) 206 225 140 146 133 188 215 223 275
Of which to
USA naa na na na na 90 124 18 78
Mexico na na na na na 30 13 12 6
Colombia na na na na na 24 12 8 9
Paraguay na na na na na 3 2 2
Argentina na na na na na b 8 2 2
Bolivia na na na na na 1
Venezuela na na na na na 1
Spain na na na na na 24 27 148 57
Germany na na na na na 1 1 6 7
France na na na na na 5 16
UK na na na na na 45
Netherlands na na na na na 12
Sweden na na na na na 12 17 15 27
Turkey na na na na na 4 5
India na na na na na 10 11
Singapore na na na na na 5
Australia na na na na na 1
Source: National statistics (19921996) and Global Trade Information Services, Inc. (19972000).
a Not available.
b Indicates nil or negligible.

small scale, operating through a series of farming cooperatives; most of the oil has been used by
domestic industries. Paraguay produces E. globulus and E. citriodora oils. Chile and Paraguay
appear occasionally as suppliers of oil in US import statistics (Table 17.5) and both were
exporting in 2000.
India
Eucalypts have been planted on a large scale in India mainly for fuelwood, pulp, pole and
afforestation purposes but the dominant species is E. tereticornis (Eucalyptus hybrid), which is
not ideally suited to oil production. Both E. globulus and E. citriodora, however, have also been
planted and these two species form the basis for Indian eucalyptus oil production.
Much research has been carried out on E. citriodora grown under Indian conditions and it
has been widely promoted as a crop suitable for small-scale cultivation for oil production.
Despite this it remains the lesser of the two species as a source of oil. Reliable estimates of Indian
production are not easy to come by and some figures which have appeared in the Indian litera-
ture have differed wildly, with no indication of the sources on which they are based. Earlier esti-
mates by Coppen and Hone (1992) put production at around 50 t of E. citriodora oil and
150200 t of cineole-rich E. globulus oil annually. Handa et al. (Chapter 11) have cited a personal
communication which puts annual production at about twice these levels, 100 and 400 t,
respectively.
Levels of Indian exports of eucalyptus oil, as recorded in the annual trade statistics, are small
and erratic and this is in line with domestic consumption which, although not possible to quan-
tify, is known to be high. Exports varied from nil (in 1991/92) or less than one tonne (in
1996/97 and 1997/98) to 39 t (in 1998/99) during the period 1990/911998/99. In the three
years where there were any significant exports, the biggest single destinations were Spain (8 t in
1990/91), France (14 t in 1994/95) and Germany (22 t in 1998/99). However, India is a net
importer of eucalyptus oil, sometimes significantly so: annual imports averaged almost 100 t
during the period 1992/931998/99 and reached 226 t in 1994/95 and 205 t in 1997/98,
almost all of it from China (or of Chinese origin).
Price trends
It is clear from what has been said earlier that world production and trade in eucalyptus oil is
dominated by the Peoples Republic of China, particularly of cineole-rich oil. It is also the main
source of E. citriodora oil although Brazil is also a major producer. Chinese sources put total
annual production of eucalyptus oil at around 4000 t with exports of about 3200 t. Official trade
statistics indicate that even these figures may be under-estimates exports have averaged
3600 t/year in recent years and exceeded 4000 t in 1994. The question as to how much of this is
genuine eucalyptus oil rather than ex camphor remains, although in terms of consumption it is
all used as if it were eucalyptus oil. In broad terms, Chinese exports during the 1990s have been
around 3000 t/year for cineole-type (medicinal) oil and 500 t/year for E. citriodora (perfumery)
oil, although there have been deviations above and below these levels.
Chinese eucalyptus oil production, and any events which may affect it, are therefore very
influential in terms of prices. With the passage of time, any eucalyptus oil prices that are quoted
soon become out of date and of only historical interest. Nevertheless, an examination of price
trends is worthwhile and demonstrates that eucalyptus oil is, indeed, a low-priced oil compared
to most other essential oils.

Cineole-rich oils and eucalyptol
Prices for standard grade Chinese 80 per cent medicinal oil and eucalyptol for the period
19811993 are illustrated graphically in Figure 17.1.3 As would be expected, price movements
for eucalyptol tend to parallel those for 80 per cent oil. The prices of comparable grades of
Spanish/Portuguese eucalyptus oil are invariably higher than that of Chinese 80 per cent oil.
The very large volumes of oil produced, combined with demand in the West and the ability
to earn valuable foreign exchange, encouraged China to pursue a policy of aggressive export pric-
ing throughout much of the 1970s and 1980s. After two exceptional high price peaks during
1973 and 1974, standard grade Chinese 80 per cent medicinal oil settled down to around
US $4.005.50/kg (CIF major world ports) before rising at the end of 1987. During the early
1990s, the centrally controlled economy gave way to economic liberalisation and this resulted in
a plethora of new businesses and trading companies, each eager to acquire a share of the eucalyp-
tus oil trade. The disruption of traditional trading practices caused, in turn, some volatility in
prices. At the same time (19901991), the opportunities for foreign multinational companies to
manufacture and market in China became greater and this led to a decrease in domestic demand
for traditional flavours such as eucalyptus. Increased supplies of Chinese-origin eucalyptus oil to
the world market coincided with a downturn in demand caused by the recession in 19911992.
All these factors contributed to the continuing fall in price of Chinese 80 per cent medicinal oil
from the high US $9.5010.00/kg mark at the end of 1988 to the US $5.00/kg level at the end
of 1991 and historically low levels around US $2.50/kg in early 1994. Prices then recovered and
in the recent past were below US $4.00/kg during 1999 but reached US $6.00/kg towards the
end of 2000 before beginning to fall. Recent prices are shown in Table 17.9.
Along with the normal ebbs and flows of seasonal changes in the supply of crude eucalyptus
oil, and the consequent firming or weakening of prices, come the less predictable changes caused
by climatic events or natural disasters. Floods or unseasonably cold weather in Yunnan,
for example, can hit the eucalyptus harvest either directly or by diverting farmers to other,
more pressing activities. Shortages of supply of eucalyptus oil ex camphor can also have an
Chinese 80% Eucalyptol
16.00
14.00
Price (US $/kg)
12.00
10.00
8.00
6.00
4.00
2.00
0.00
1981 1983 1985 1987 1989 1991 1993
Mar 1981 Dec 1993
Figure 17.1 Price trends for Chinese 80 per cent eucalyptus oil and eucalyptol, 19811993.
3 The graphs (and those of Figure 17.2) are based on average prices per quarter (CIF Main European Port for
Figure 17.1). Source: London dealer.

Table 17.9 Price movements for Chinese 80 per cent cineole eucalyptus oil over
two years, 19982000 (US $/kg, CIF Main European Port)
Date Price Date Price Date Price
Sep 1998 3.50 Oct 1999 3.70 May 2000 4.50

May 1999 3.45 Nov 1999 3.85 Jul 2000 4.75
Jun 1999 3.20 Dec 1999 3.60 Aug 2000 5.25
Aug 1999 3.15 Jan 2000 3.75 Sep 2000 6.00
Sep 1999 3.55 Mar 2000 4.40 Oct 2000 5.75
Source: London dealer.
Chinese Brazilian
10.00
Price (US $/kg)
8.00
6.00
4.00
2.00
0.00
1981 1983 1985 1987 1989 1991 1993 1995 1997
Mar 1981 Dec 1997
Figure 17.2 Price trends for Chinese and Brazilian Eucalyptus citriodora oil, 19811997.
effect: eucalyptol producers may be forced to switch to E. globulus oil as a feedstock, with a con-
sequent effect on the availability and price of Chinese 80 per cent oil.
E. citriodora oil
Prices for Chinese and Brazilian E. citriodora oil for the period 19811997 are illustrated graph-
ically in Figure 17.2. Neither source has been consistently lower priced than the other although,
as noted, Chinese prices are CIF, compared with Brazilian FOB. For most of the period prices
were in the range US $35/kg but towards the end of 1994 they rose fairly sharply and had dou-
bled to US $7.80 (Brazilian) and US $9.00/kg (Chinese) by late 1995 before falling and levelling
out at just over US $6/kg during 1997. For most of 2000, Chinese E. citriodora oil was in the
range US $5.506.00/kg; in October 2000, one London dealer was quoting US $5.75/kg.
The outlook
Given the uncertainty of the plans for Western Australian eucalyptus oil production, China will,
for the foreseeable future, continue to be the dominant force in eucalyptus oil supplies and
events in China will be of prime importance in determining prices, particularly for cineole-type
oils. However, with the liberalisation in China came a keenness to diversify and develop value-
added industries, fuelled in part by the desire to meet the domestic demands of an increasingly

consumer-conscious society but also by the desire of foreign fragrance and flavour companies to
invest in a part of the world which, as well as being the centre of production of many of the
major essential oils, has an indigenous technical expertise and can support relatively low-cost
operations. So today, while Chinese eucalyptus oil remains a high-volume, relatively low-priced
oil, exported for use in blending and compounding by others, there has been an expansion and
consolidation in China of its own refining and marketing activities, particularly in and around
Kunming, Yunnan, and often through joint ventures with foreign companies.
As Smith (1998) has observed in the context of the fragrance and flavour industry:
The world has become, in recent years, an increasingly uncertain place to do business. The
economic turmoil seen in many countries, and particularly in Asia Pacific and the former
Soviet Republics, has sent echoes reverberating around the financial markets of the world.
As information technology develops, these markets move more rapidly than ever before and
capital becomes increasingly mobile. At the same time there is more opportunity than
ever before for those companies with the will and courage to go after it. Market deregula-
tion, the lowering of international tariff barriers, the development of global markets and
the emergence of new markets are features of the international business landscape that
provide prospects for growth and development in abundance.
The increasing globalisation imposes greater demands on both smaller companies and suppli-
ers of eucalyptus oil (and any other essential oils) in the developing world. Jackets (1998) has
indicated that the move towards global purchasing contracts, together with global quality stan-
dards, including the implementation of ISO 9000, has led the major companies to install stricter
control on the suppliers, who must also be capable of providing the necessary documentation.4
All this suggests that those in the eucalyptus oil business whether they are suppliers, dealers,
processors, compounders or manufacturers of final products who can adapt positively to the
changes that are taking place will survive and prosper. In the West, increasing public awareness
of green issues and attention to product labelling will ensure that natural products such as
eucalyptus oil will continue to find favour in the marketplace. In the East, the massive potential
of increasing consumer demand in countries such as China, India and those of the former Soviet
Union beckons, though it may be some time before it becomes a reality.
References
Bartle, J.R. (1999) Why oil mallee? In Oil Mallee Profitable Landcare, Proc. Oil Mallee Association Seminar,
Perth, Western Australia, March 1999, pp. 410.
Coppen, J.J.W. (1995) Flavours and Fragrances of Plant Origin, Non-Wood Forest Products Series, No. 1,
Food and Agriculture Organization of the United Nations, Rome.
Coppen, J.J.W. and Hone, G.A. (1992) Eucalyptus Oils. A Review of Production and Markets, Bulletin 56,
Natural Resources Institute, Chatham, UK.
4 The burden on the supplier arising from increasing legislation centred on environmental and safety concerns is
discussed in Appendix 6.

Jackets, P.A. (1998) The combined effects of technology and the global shift to market economies. In
Global Markets: Present and Future, Proc. IFEAT Internat. Conf. Essential Oils and Aromas, London,
November 1998, pp. 208220.
McKelvie, L., Bills, J. and Peat, A. (1994) Jojoba, Blue Mallee and Broombush: Market Assessment and Outlook,
ABARE Research Report 94.9, Australian Bureau of Agricultural and Resource Economics, Canberra.
RIRDC (1999) Integrated Tree Processing of Mallee Eucalypts. Report by Rural Industries Research and
Development Corporation, Barton, ACT, Australia.
Sewell, M. (1998) Eucalyptus oil: a review of world production and trade. In Proc. Internat. Seminar on
Yunnans Trade Development, Kunming, China, April 1997, China-EU Centre of Agricultural Technology
(CECAT), Beijing, pp. 109122.
Smith, C.M. (1998) World markets and the current business context. In Global Markets: Present and Future,
Proc. IFEAT Internat. Conf. Essential Oils and Aromas, London, November 1998, pp. 15.
Wang, H. and Green, C.L. (1990) A review of eucalyptus oil: production, market and its prospect in the
world. World For. Res., 3(2), 7176.

18 Research trends and future prospects
Erich V. Lassak
Introduction
There are at present approaching 1000 or so fully described species of Eucalyptus and this number
continues to grow. Included amongst these species are the bloodwoods, previously of the sub-
genus Corymbia but which were elevated to a separate genus, Corymbia, by Hill and Johnson
(1995). For the purpose of this chapter, as throughout this book, and in line with the preference
of Brooker (Chapter 1), species of Corymbia will be retained here under the genus Eucalyptus.1
Owing to the unusually large size of this almost exclusively Australian genus, and to the fact that
many botanical descriptions have been published in relatively little known and less accessible
Australian journals, many names, now obsolete, continue to appear in the literature. A case in
point is the frequent use of the old name E. rostrata instead of E. camaldulensis. The compilation
and dissemination of a regularly up-dated list of species and synonyms would be of great assis-
tance to researchers working in this field, and lessen the chance of duplication occurring when dif-
ferent workers investigate the same species under two or more different names. The task would be
made easier using electronic forms of communication.
The factors which have influenced past research into the chemistry of eucalypts (and in par-
ticular of their essential oils) combine, perhaps more than in most other plant genera, pure sci-
ence with applied science, that is, aspects related to their commercial utilisation. A wide range
of topics has been discussed in preceding chapters of this volume and it is evident that Eucalyptus
will continue to provide new or improved commercial opportunities which, in turn, will be a
driving force for further research. This chapter examines certain aspects of past work, highlights
some areas of current research and indicates where additional research might be required for a
better understanding of the chemistry of Eucalyptus and for a continuing expansion of its eco-
nomic potential. Although earlier research focused on the volatile constituents of eucalypts
their essential oils and these have largely been the basis upon which the industry exploiting
the aromatic and medicinal uses of eucalyptus has been built, research in the last two decades
has demonstrated the commercial potential, particularly in the pharmaceutical field, of the
non-volatile constituents. Both types of compounds are therefore discussed below.
Extraction of eucalyptus leaf oils
Developments in large-scale commercial extraction

What developments have there been in the methodologies used for large-scale extraction of
eucalyptus oils and are there any pointers for the future? Steam distillation (or in rare cases
1 Corymbia citriodora, previously named Eucalyptus citriodora, is the source of the commercially important E. citriodora
oil and will, without any doubt, continue to be traded under its old name.

hydrodistillation) at atmospheric pressure is the traditional and most widely used method for
the extraction of eucalyptus oils. More or less freshly harvested foliage, including terminal
branchlets, is used without any pre-treatment. Distillation times are of the order of several hours
depending on the nature of the oil being extracted: 1,8-cineole or citronellal-rich oils require
shorter distillation times than, for example, piperitone-rich oils.
Since eucalyptus oil glands are buried deep within the leaf tissue they require longer times
to rupture and to release the oil than oil cells located in the epidermis of leaves or flowers (as
found, for example, in most plants of the family Lamiaceae). Consequently, various attempts
have been made to reduce the distillation time by crushing or grinding the leaves, and thus
at least partly releasing the oil, before steam distilling them. Whilst the time required for
complete oil extraction may, indeed, be shortened, production costs are usually increased. The
chief reason for this increase in costs is the additional machinery and processing time required.
Furthermore, oil recovery tends to be significantly poorer as some of the lower-boiling
components of the oil evaporate and are lost during the comminution process (Provatoroff 1972,
Abbott 1989).
Continuous steam distillation, as opposed to the normal batch process, has also been
attempted by several Australian eucalyptus oil producers. However, the technical difficulties
proved sufficiently serious that this approach had to be abandoned.
The possibility of producing eucalyptus oils by expression from some of the higher oil-yield-
ing species was investigated at the Museum of Applied Arts and Sciences in Sydney (where most
of the eucalyptus oil research in Australia was carried out up to the late 1970s). Whilst some liq-
uid was obtained by the application of quite high hydraulic pressures, no significant quantities
of essential oil separated, even after centrifugation.
Some recent Western Australian research has examined the possibility of using solar energy to
drive off essential oil and water vapour from foliage contained in very large plastic film cham-
bers, and to separate the oil after condensation of the vapours. The technique apparently shows
some promise (Giles 1998).
It is the authors opinion that for Australian producers, and perhaps others where labour
costs are high, the Australian method of steam distilling foliage which has been mechanically
harvested directly into a mobile still is well-established and proven in terms of simplicity and
cost effectiveness: labour costs are kept to a minimum, fuel costs are almost nil as the air-dried
spent foliage provides all the energy required to raise steam, and quantities of cold water are
usually readily available. Low production costs are essential since virtually all commercial
eucalyptus oils have much lower unit values than essential oils from other plant families.
Outside Australia where, for various reasons, mechanised harvesting may not be possible or
appropriate, there is still scope for greater efficiency in terms of improved oil yields, lower
production costs, etc., using conventional methods of distillation. Significant improvements can
be gained by adopting many of the good manufacturing practices advocated by Denny (Chapter
6). Attempts to develop novel methods of extraction, even if technically feasible, may ultimately
prove not to be viable commercially and thus wasteful as far as effort expended and financial cost
are concerned.
Small-scale laboratory extraction methods

Long before any commercial operation can be contemplated, and in order to provide necessary
data on oil yields and composition, plant material must be analysed in the laboratory. But the
analytical procedure itself (as well as the sampling) must be sound if the conclusions drawn are
to be valid. What methods are available and do alternatives to traditional ones which have been
used in recent years offer any advantages?

Perusal of the recent literature shows that the traditional method of essential oil extraction by
steam entrainment, that is, hydrodistillation with or without cohobation and, less frequently,
true steam distillation, is no longer the sole method used. Other methods, often claimed to be
milder owing to the use of lower extraction temperatures and the absence of acidic still waters
(and therefore less likely to cause heat or pH-induced artifact formation such as the hydrolysis of
esters, skeletal rearrangements, etc.), include solvent extraction and supercritical fluid extrac-
tion, vacuum distillation, and even the extraction of the oil directly from the leaf by means of
capillaries inserted into the oil glands. The choice of extraction method will depend on the num-
ber of plant samples to be extracted, the resources available and the intended use of the results
thus obtained.
Traditional methods
Hydrodistillation and steam distillation, being technologically the simplest, and also the cheap-
est, are quite appropriate for experiments aimed at the eventual commercial utilisation of the oil.
The primary constituents of the major commercial eucalyptus oils are 1,8-cineole, citronellal,
piperitone and !-phellandrene; methyl cinnamate is the main component of a minor oil. None of
these compounds are significantly affected by hydrodistillation and, since all commercial oils
containing these substances are very cheap, large-scale solvent extraction or vacuum distillation
techniques must be ruled out on grounds of cost. However, distillation times utilised by differ-
ent groups of workers have varied widely, ranging from 2 h (Dellacassa et al. 1990) to 30 h
(Bignell et al. 1995). Times are usually between 3 and 24 h but in the overwhelming majority of
cases little or no explanation is given in the published literature for the use of particular distilla-
tion times and one must assume that the cut-off values represent apparent cessation of oil accu-
mulation. Furthermore, in apparatus such as the Clevenger, Likens-Nickerson and modified
Dean-Stark, the condensed aqueous distillate passes continually through the column of collected
essential oil, thereby disturbing it and often carrying oil globules back into the still; accurate
measurement of the volume of oil collected is therefore difficult. An oil receiver developed by
McKern and Smith-White (1948), later modified by Hughes (1970) in order to permit the
simultaneous collection of heavier-than-water oils or oil constituents, eliminates most of the
problems associated with the earlier types of apparatus. In particular, the end point of the distil-
lation is accurately determined from a distillation curve constructed by plotting the volume of
essential oil vs time. This method was used by Lassak (1990, 1992) who showed that hydrodis-
tillation of most of the Eucalyptus species tested required quite long distillation times for com-
plete oil extraction; three examples are shown in Figure 18.l.
Complete essential oil extraction is necessary if the real quantitative composition of the oil, as
present in the foliage, is sought. It is well known that the composition of the oil varies with dis-
tillation time (e.g. Koedam et al. 1979) and any practising essential oil chemist will have
observed that essential oils change in colour and viscosity as the distillation progresses.
In eudesmol-rich eucalypts, for example, the oils tend to become progressively more viscous
and often solidify in the receiver towards the end of the distillation. Table 18.1 illustrates, in the
case of two Eucalyptus species, how different distillation times can affect the overall composition
of the oil.
Solvent extraction methods

Solvent extraction is a technique relatively rarely used for the recovery of eucalyptus oil. Weston
(1984) showed that, in contrast to conventional water distillation, the dichloromethane-extracted

E. erythrocorys E. stricklandii E. woodwardii
Fraction of total essential oil (%)
100
80
60
40
20
0
0 5 10 15 20 25 30 35
Distillation time (h)
Figure 18.1 Distillation curves for three species of Eucalyptus.
Table 18.1 Influence of distillation time on the composition of eucalyptus oil (in
terms of sesquiterpenoids)
Species Distillation Sesquiterpenoids Reference

time (h)
E. globulus 2 Traces Dellacassa et al. (1990)

6 Significant amounts Li and Madden (1995)
8 Significant amounts Boland et al. (1991)
E. nitens 3 None Franich (1986)
8 Significant amounts Boland et al. (1991)
oil of E. delegatensis contained little more than traces of !-phellandrene. He suggested that the
!-phellandrene normally produced was an artifact resulting from the dehydration of trans-piperitol.
It would be interesting to check this by applying the same procedure to other hydrodistilled
eucalyptus oils rich in !-phellandrene such as those obtained from the non-cineole forms of
E. dives and E. radiata subsp. radiata.
Although ethanolic extraction of eucalyptus oils has no commercial significance, Ammon
et al. (1985) have suggested its use for the rapid and accurate determination of terpenes, particu-
larly 1,8-cineole, in the foliage of eucalyptus. The method has been applied to several Eucalyptus
species by Brooker et al. (1988), Doran and Brophy (1990) and Grayling and Brooker (1996) and
appears to give quite satisfactory results. However, the claim that it is a rapid method is perhaps
somewhat exaggerated in view of the very long extraction times required for complete extraction
of the oils (at least two weeks in the cases cited). Its suitability for analysing Eucalyptus species
such as E. cloeziana (!-pinene chemotype), which have leaf oils composed almost entirely of
monoterpenoid hydrocarbons (Boland et al. 1991), also needs to be tested to see whether extrac-
tion is quantitative monoterpenoid hydrocarbons are not very soluble in ethanol containing
even small amounts of water.
Supercritical fluid extraction (SFE) is a relatively recent extension of the normal solvent
extraction technique. Supercritical CO2 behaves like a lipophilic solvent but by varying the

temperature and pressure selectivity can be achieved. The low extraction temperatures normally
used, as well as the absence of an acidic aqueous phase, reduce the likelihood of artifact forma-
tion from any chemically labile plant constituents which may be present, thus yielding a more
nature-like extract. However, as Della Porta et al. (1999) have pointed out, the optimum
extraction conditions must be chosen in order to avoid the co-extraction of undesirable high
molecular weight compounds. Whilst SFE methods are suitable for the production of some nat-
ural flavours and fragrances they have not been applied to any significant extent to the extraction
of eucalyptus oils. One of the probable reasons for this is the relatively high cost of SFE, which
can be justified in the case of high-priced flavour and fragrance materials but not with the
cheaper eucalyptus oils. Apart from a brief mention in connection with the extraction of an
unnamed species of Eucalyptus (Hawthorne et al. 1989) the only substantial investigations have
been those of Milner et al. (1997) and Della Porta et al. (1999). Milner et al. (1997) found that
the qualitative and quantitative compositions of the sesquiterpenoid fractions present in super-
critical CO2-extracted leaf oils of E. varia subsp. varia and E. sparsa were similar to those of leaf
oils obtained by vacuum distillation, but quite different from hydrodistilled oils. The main dif-
ferences with the latter were the high levels of bicyclogermacrene and low levels of certain
sesquiterpenoid alcohols such as !- and "-eudesmol, globulol and viridiflorol in the SFE-
extracted oils, the reverse of what is found in the hydrodistilled oils. Della Porta et al. (1999)
extracted E. globulus leaves and obtained an oil richer in 1,8-cineole than one produced using
conventional hydrodistillation.
Vacuum distillation
Another interesting development is the extraction of eucalyptus leaf oils by means of vacuum
distillation. This rather novel procedure, developed by Inman et al. (1991), involves the extrac-
tion of the oil from plant material which has been frozen with liquid nitrogen and reduced to a
fine powder; it is then subjected to a vacuum and the volatiles condensed on a gold-plated cop-
per rod maintained at around #75C. This method has been used by Bignell et al. (e.g. 1997 and
other references of theirs cited therein) to analyse a large number of Eucalyptus species. The
chemical compositions of the oils obtained in this manner showed some significant differences
with respect to hydrodistilled oils (Bignell et al. 1995, 1996) and led the authors and Milner
et al. (1997) to suggest that vacuum-distilled oils reflect more closely the composition of the oils
present in the living leaf tissue. In particular, they found that bicyclogermacrene levels were
much higher in vacuum-distilled oils, while hydrodistilled oils contained more sesquiterpenoid
alcohols (as in SFE-extracted oils). They proposed that the compositional differences observed in
hydrodistilled oils might be due to hydrogen ion initiated reactions of bicyclogermacrene, as
suggested by Tressl et al. (1983) in the case of hops (Humulus lupulus).
Despite the claims that vacuum distillation produces oils more akin to the original in vivo
oils, some of the results presented by Bignell et al. (1995, 1996) appear to contradict this. The
chemical changes undergone by bicyclogermacrene during hydrodistillation appear to be beyond
dispute but the ratio of C15 : C10 compounds (i.e. total sesquiterpenoids vs total monoterpenoids)
in the vacuum-distilled oils and in hydrodistilled oils of the same samples of foliage should be
approximately the same. In fact, in the case of E. sparsa and E. rudis, they are very dissimilar
(Table 18.2). One other issue needs to be addressed: the possible loss of certain volatile
constituents such as isovaleraldehyde (3-methylbutanal). Despite the fact that this compound
occurs in many Eucalyptus species, and is an undesirable constituent of several commercial euca-
lyptus oils such as E. globulus and E. smithii (see Appendix 4), it has not been reported in
vacuum-distilled oils of the type produced by Bignell and her co-workers.

Table 18.2 Comparison of vacuum-distilled and hydrodistilled oils obtained by Bignell and co-workers in
terms of monoterpenoid (C10) and sesquiterpenoid (C15) content
Species Vacuum-distilled oil Hydrodistilled oil
Total C10 Total C15 C15/C10 Total C10 Total C15 C15/C10
(%) (%) ratio (%) (%) ratio
E. sparsaa 23.1 67.2 2.9 33.1 59.2 1.8

E. rudisb 8.2 83.2 10.1 19.3 66.2 3.4
a Bignell et al. 1995.

b Bignell et al. 1996.
Other methods
Hellyer (1963) was able to remove the essential oil from the oil glands of individual E. dives
(piperitone chemotype) leaves by inserting a glass capillary directly into the oil gland under a
microscope using a micromanipulator. Capillary GC showed that the gas chromatograms of the
capillary-isolated oil and of the hydrodistilled oil from the same batch of leaves were almost iden-
tical, both qualitatively and quantitatively. Of all the extraction techniques available, this is prob-
ably the one most likely to yield artifact-free oils. Using the same technique, Malingr et al.
(1969) successfully isolated the essential oil of Mentha aquatica. Milner et al. (1997) mention
unpublished work on the manually removed oils from E. torquata, E. sparsa and E. woodwardii and
their similarity to vacuum-distilled oils (e.g. Bignell et al. 1995). Unfortunately, the method is
very slow and the glands of many Eucalyptus species are very small and difficult to handle.
It is clear that the trend is towards milder methods of essential oil extraction since such oils
should represent more accurately the oils originally present in the leaves. (Note, however, that
the question as to whether the market would accept an oil that has a different composition and
therefore, inevitably, different aroma characteristics to the traditional one, albeit that it is
closer to the intrinsic oil, would remain to be answered). However, there are two aspects to
be considered, a quantitative one has all the oil been not only extracted but quantitatively
recovered? and a qualitative one how does the chemical composition of the extracted oil
compare with that of the oil contained in the oil glands? The method of extraction should also
be relevant to the goals of the investigation. None of the methods referred to above are likely to
satisfy all these requirements.
It can be argued that cohobative hydrodistillation is the simplest and most suitable method
for the laboratory extraction of eucalyptus oils, particularly if directed towards the evaluation of
their eventual commercial potential, and if it is standardised then oil yield values and oil com-
positional data obtained by different groups of workers should be directly comparable. Such
standardisation could be achieved by adopting the Hughes-modified McKern/Smith-White
type of oil receiver, together with the distillation curve technique for monitoring the progress of
the oil extraction. Using typical sample sizes of 3001000 g of plant material, the method pro-
vides quite accurate information on both oil yields and quality (chemical composition). The fact
that some chemical changes can occur (due to a combination of elevated temperature and weakly
acidic conditions inside the distillation vessel) does not detract from the usefulness of this
method if the quality and characteristics of the oil are what the industry demands. The most commonly
encountered changes relate to the decomposition of terpenic esters (Pickett et al. 1975), the
transformation of sabinene and sabinene hydrates to terpinen-4-ol (Southwell and Stiff 1990 and
references therein), the Cope rearrangement of hedycaryol to elemol ( Jones and Sutherland

1968), of germacrene C to $-elemene (Morikawa and Hirose 1969) and of bicyclogermacrene to
bicycloelemene, as well as its isomerisation to derivatives of aromadendrene and alloaromaden-
drene such as globulol, ledol, etc. (Nishimura et al. 1969). Hydrodistillation offers further
advantages: oils can be isolated, and their yields determined, without recourse to expensive
instrumentation, which may not be readily accessible in small field laboratories in some devel-
oping countries; and it allows the early elimination of samples which do not show promise as far
as oil yields are concerned.
As a final word of caution, the isolation of an artifact-free leaf oil does not guarantee that its
analysis will provide an artifact-free composition. If gas chromatography is used for analysis, as
is commonly the case, the high injector temperatures employed are likely to give rise, even if
only partially, to certain types of reactions (such as Cope rearrangements and polymerisations)
which will distort the genuine composition of the oil. The combination of a mild extraction
method coupled with a mild analytical technique, perhaps HPLC, would be ideal. Unfortu-
nately, HPLC is not as yet either sufficiently sensitive or sufficiently discriminatory to be able to
separate complex mixtures of terpenoids.
Analysis of essential oils
Identification of essential oil constituents

With the development of instrumental techniques it has been possible to dispense with the need
to identify oil constituents by isolation and measurement of their physical constants and by the
properties of their crystalline derivatives. The use of capillary gas chromatography (GC) and
spectral techniques such as mass spectrometry (MS), especially when combined (GC-MS), has
been described elsewhere in this volume (Chapter 5) and has enabled the routine examination of
essential oils to be achieved more simply, rapidly and reliably than ever before.
However, a few words of caution are necessary. Many of the published eucalyptus oil analyses
have been carried out using just one type of GC column, often a polar one such as BP 20 or equiv-
alent. Such columns do not separate !-pinene from !-thujene (or only very incompletely) and this
probably explains why the latter compound has been only rarely reported in the literature. In the
authors experience !-thujene is frequently found in eucalyptus oils, albeit in very small amounts.
The use of a second, apolar, column usually solves this problem and may bring other examples of
multiple peaks to light. It is good practice, always, to use two columns of different polarity in any
essential oil work. This has long been recognised by the International Standardization
Organization (ISO), which includes both types of chromatogram in all its standards.
Monoterpenoid esters can sometimes prove troublesome as their mass spectra do not always
exhibit a molecular ion. The monoterpenoid ketone cryptone (C9H14O, mol. wt. 138) is a compar-
atively unusual eucalyptus oil constituent and has been wrongly reported as menthyl acetate in the
leaf oils of E. benthamii var. benthamii, E. dives (piperitone form), E. elata, E. polybractea, E. propinqua
and E. sp. aff. propinqua (Boland et al. 1991), partly because its molecular ion at z/e 138 was thought
to be derived from the loss of acetic acid from the ephemeral molecular ion of menthyl acetate,
C12H22O2, mol. wt. 198 ( J. Brophy pers. comm.). In most cases, any uncertainties can be avoided
by co-injection of the test sample with the authentic compound. It is the authors firm belief that
this check with authentic compounds is essential as an adjunct to GC-MS generated data, espe-
cially when the constituent in question is not commonly found in oils of Eucalyptus.
From a chemotaxonomic, as well as an economic, point of view it is disappointing that so
many eucalyptus oil constituents, particularly sesquiterpenoids, remain unidentified. It is to be
hoped that this will be addressed by future workers since minor constituents can sometimes

exhibit interesting, and potentially valuable, bioactive properties. Two such examples are
the steam-volatile allelopathic substances, cis- and trans-(%)-p-menthane-3,8-diol, present in
E. citriodora leaves (Nishimura et al. 1982).
The ready availability of chiral stationary phases permits the determination of the enan-
tiomeric composition of essential oils. This technique has been rapidly gaining in importance
but, for some reason, has not been applied to any significant extent to eucalyptus oils, perhaps
because the main constituent of most commercial oils is the optically inactive 1,8-cineole. Chiral
analysis has important commercial, as well as scientific, applications. It can be used to establish
the genuineness of particular essential oils as the enantiomeric ratio of a given unsymmetrical
terpenoid appears to be species-specific. In such cases, chiral analysis can help in revealing adul-
teration with other essential oils or with isolates which are either synthetic or derived from
another plant species. It can also be useful in toxicological studies of essential oils since enan-
tiomers of some compounds exhibit different toxicities: l-pulegone, for example, is less toxic
than d-pulegone (Opdyke 1978). Finally, chiral analysis would be of considerable use in the
elucidation of essential oil biosynthesis.
Chemical variation within a species

The concept of chemical variants (also called chemical forms or chemotypes) has been discussed
elsewhere (e.g. Chapters 4 and 5) but a few points are worth reiterating. The concept has been
based on the existence of discontinuities in the chemical composition of certain eucalyptus oils.
However, the development of more sensitive analytical methods, such as capillary GC, has indi-
cated that in some of those cases previously considered to be examples of qualitative variation,
the variation was only quantitative, as in E. dives (Hellyer et al. 1969). Before proposing the exis-
tence of chemical variants one also needs to be satisfied that the sampling procedures used have
been sound. The age of the leaves sampled and the sample size (in terms of number of trees) are
just two important considerations. Immature leaf tips of the citronellal form of E. citriodora, for
example, contain less citronellal than young mature leaves (Penfold et al. 1953 and references
therein). Sampling a large number of individual trees collected at random from different loca-
tions and spanning, as far as possible, the whole of the known natural distribution of the species
is extremely important since in some Eucalyptus species a particular oil constituent can vary
continuously between very wide limits. Southwell (1973), for example, found that 1,8-cineole varied
from 1 to 70 per cent in the leaf oil of E. punctata. Characterisation of a species by sampling an inad-
equate number of trees can introduce a false discontinuity and result in the postulation of chemical
variants where none actually exist.
One more word of warning: hybridisation is not uncommon amongst eucalypts and the unin-
tended inclusion of unrecognised hybrid trees in an essential oil investigation will distort the
results and render them useless for chemotaxonomic purposes. In later years, it became common
practice at the Museum of Applied Arts and Sciences in Sydney to grow progeny from the seed
of wild growing trees and to investigate their leaf essential oils only if all trees thus raised were
morphologically identical, indicative of an absence of hybridisation.
Search for new commercial uses of Eucalyptus extracts
Essential oils
Most published work has focused on the chemistry of leaf oils, and this is likely to continue to be
the case. All Eucalyptus leaf oils are very complex mixtures of terpenoids (mainly mono- and

sesquiterpenoids), certain shikimate-derived compounds such as "-triketones and some pheno-
lics, and, to a much smaller extent, some relatively rare non-terpenoid aliphatic compounds.
Flavour, fragrance and medicinal use

In order to be of any commercial interest, yields of leaf oil should be at least 1.52 per cent based
on the mass of the fresh plant material (leaves and terminal branchlets) and there should prefer-
ably be one main oil constituent one which has an established market and is present in reason-
ably high concentrations (normally not less than 4570 per cent of the oil, depending on the
particular constituent). In the great majority of Eucalyptus species these two requirements are not
satisfied simultaneously: either the oil yield is too low or the chemical composition is unsuit-
able, or both. In the case of cineole-rich oils, recent literature indicates that only a few species
with possible commercial potential have been identified (Table 18.3), additional to those which
already are, or have once been, used commercially for oil production (Lassak 1988, Coppen and
Hone 1992).
A non-cineole eucalypt with some commercial potential is E. nova-anglica, which contains a
leaf oil rich in nerolidol (77 per cent), a sesquiterpene rarely found in eucalypts (Boland et al.
1991, Brophy et al. 1992); oil yield is approximately 2.7 per cent (fresh weight basis). Another
non-cineole/non-citronellal species whose commercial potential has recently been realised is
E. olida, previously referred to as Eucalyptus sp. nov. aff. campanulata (Curtis et al. 1990); its leaf
oil, produced in Australia, contains E-methyl cinnamate to the extent of about 95 per cent.
The greater part of the present world eucalyptus oil production of about 25003000 t/year is of
the 1,8-cineole type. Most 1,8-cineole type oils are used medicinally whilst smaller quantities are
consumed by the flavour and fragrance industries. Existing eucalyptus plantations established
throughout many warmer regions of the world not only for essential oil production but, more
importantly, as a renewable source of firewood are more than adequate in satisfying present
Table 18.3 Cineole-rich Eucalyptus species with commercial potential
Species Oil yield a 1,8-Cineole Reference

(%) content of oil (%)
E. badjensis 2.8 70 Boland et al. (1991)

E. bakeri 1.83.0 8596 Brophy and Boland (1989)
E. brownii 1.92.3 8089 Boland et al. (1991)
E. globulus subsp. maidenii 2.22.8 4670 Boland et al. (1991)
E. globulus subsp. pseudoglobulusb 4.05.6c 4769 Boland et al. (1991)
E. kochii subsp. kochii 2.35.5c 8394 Gardner and Watson (1947/48),
Brooker et al. (1988)
E. kochii subsp. plenissima 2.28.6c 8395 Gardner and Watson (1947/48),
Brooker et al. (1988)
E. loxophleba 2.4 67 Boland et al. (1991)
E. nichollii 1.72.3 84 Boland et al. (1991)
E. pumila 3.85.8c 8090 Boland et al. (1991)
E. salubris 1.42.3 78 Brophy and Lassak (1991)
E. saxatilis 3.55.1c 6479 Boland et al. (1991)
E. sturgissiana 1.12.5 8090 Boland et al. (1991)
E. subcrenulata 2.54.6c 6166 Boland et al. (1991)
a Fresh weight basis except where indicated.

b Oil from this species has probably been produced and marketed under the name E. globulus.
c Dry weight basis.

world demand for cineole-rich oils. In addition to these stocks, however, huge numbers of
eucalypts are being planted to satisfy an ever-growing demand for paper pulp, artificial board
and timber for general construction purposes. They are also being planted to combat soil salina-
tion due to rising ground water levels in deforested arid or semi-arid areas (for example, in
Western Australia). Where these eucalypts are suitable oil-bearing species the potential exists,
therefore, for a manyfold increase in eucalyptus oil production, although the supply could not be
matched by an increase in demand, at least in terms of existing markets.
Fuel use
Concerns raised in the 1970s about decreasing world supplies of fossil fuels led to the examina-
tion of plants as a potential source of hydrocarbons which could be used to extend, or even sub-
stitute for, fuels normally derived from crude petroleum. Eucalyptus oils of the 1,8-cineole type
ranked fairly high on the list of possible substitute fuels (Nishimura and Calvin 1979,
Nishimura et al. 1980, Ammon et al. 1985, Beckmann 1988, Duffy 1993, etc.). It is quite sur-
prising that this kind of thinking persisted into the 1990s in view of earlier reports which ques-
tioned the ability to produce liquid fuels from plants in quantities sufficient to meet projected
demand (Gartside 1977, Coffey and Halloran 1979).
E. polybractea leaf oil yields of up to 10 t/km2 annually have been achieved in Australia on
selected plantations and under ideal conditions. In South Africa, where the higher oil-yielding
E. radiata subsp. radiata (E. australiana of commerce) is being grown, annual oil yields of about
20 t/km2 are believed to be achievable (Davis 1998). Small-scale experiments conducted in
South Africa with the same species have indicated that still higher annual oil yields, up to
45 t/km2 might be possible (Donald 1980). World crude oil consumption in 1990 was estimated
to be close to 3,000 million tonnes. Even if one sought to replace just a fraction, say 10 per cent,
of that figure with eucalyptus oil, perhaps as an additive to petrol/ethanol fuel mixtures, and
using an annual yield of 20 t/km2, the quantities of oil needed would require an arable and well
watered growing area of millions of square kilometres. It is reasonable to assume that a signifi-
cant proportion of the eucalyptus oil so produced would finish up being used to power the heavy
machinery required for soil preparation, planting of seedlings, harvesting of the foliage, etc. The
production cost of eucalyptus oil from even the most highly mechanised commercial plantations
is still of the order of US$23/kg of oil produced. This is at least ten times the production cost
of petrol (gasoline). Even if the recently introduced carbon credits were taken into account it is
still most unlikely that eucalyptus oil could ever become a viable substitute for petroleum-based
fuels on a global scale.
Use as a solvent/cleaning agent

A more promising future for eucalyptus oils appears to lie in their use as industrial solvents.
Eucalyptus oils, particularly those containing piperitone or !-phellandrene as their major com-
ponents, have been known for a long time to be excellent solvents for paints, resins, varnish,
grease, gums, tar, etc. (Penfold and Morrison 1950). In the past, cineole or cineole-rich eucalyp-
tus oils, with or without addition of phellandrene, have also been suggested for use as paint
removers and clothes cleaners. At the time, their relatively high price prevented them from
being used on a large scale but they have enjoyed something of a rebirth as a popular wool wash
in Australia in recent years.
Recent concerns about the harmful effects of chlorinated solvents such as chloroform,
trichlorethylene and 1,1,1-trichloroethane on human health and the environment have led to a

search for chlorine-free solvents of comparable solvent power. 1,8-Cineole and cineole-rich euca-
lyptus oils appear to fulfil most of the requirements sought of such solvents: biodegradability,
low toxicity, ability to dissolve grease, no adverse effect on the Earths ozone layer and low chem-
ical reactivity, as well as a pleasant odour. Industrial trials conducted in Western Australia have
been successful and cineole is now routinely used as a degreasing agent (Barton 1989, Barton
and Knight 1997). An added advantage is the ease with which it can be recovered from the
degreasing solutions, either by direct distillation or by steam distillation. Its main disadvantage
is its low flash point (about 48C for 1,8-cineole and 44C for eucalyptus oil containing 8085
per cent cineole) and relatively high boiling point (176177C).
Chemical and microbiological transformations as a route to commercially useful products

A very large body of literature exists on the chemical reactions and transformations which
terpenoids undergo. However, only very few such reactions have resulted in commercially useful
products which can be obtained in sufficient yield and purity to warrant large-scale industrial
production. Citronellal, a major constituent of the leaf oil of E. citriodora, as well as of several
plant species belonging to other genera, is the starting material for the manufacture of hydroxy-
dihydrocitronellal (commercially known as hydroxycitronellal), an important perfumery com-
pound. l-Piperitone from E. dives leaf oil was used until relatively recently as the starting
material for the synthesis of l-menthol used in flavours. Derivatives of 1,8-cineole have not yet
found commercial application.
Both piperitone and !-phellandrene, major constituents of E. dives (piperitone form),
E. radiata subsp. radiata (the chemical form once called E. phellandra) and several other species,
contain reactive functional groups which lend themselves to chemical manipulation. Piperitone
can be reduced to a mixture of cis- and trans-piperitols, which yield fragrant esters on esterifica-
tion with low molecular weight aliphatic carboxylic acids. !-Phellandrene can be converted to
DielsAlder adducts which may have commercial potential as plasticisers. It might also be pos-
sible to react !-phellandrene with vinylic co-monomers to produce polymers with novel and
desirable properties.
Transformations of chemical structures can also be achieved by the action of microorganisms.
Early examples were the use of bottom yeast to convert citronellal to citronellol in 59 per cent
yield (Mayer and Neuberg 1915) and the conversion of citronellal to a mixture of citronellol and
citronellic acid using Acetobacter xylinum (Molinari 1929). More recently, racemic piperitone has
been converted to a mixture of (%)-trans-6-hydroxy-p-menth-1-en-3-one (minor product) and
(%)-7-hydroxy-p-menth-1-en-3-one (major product) by organisms such as Fusarium,
Proactinomyces roseus and Aspergillus niger (Lassak et al. 1973). A more interesting development is
the conversion of 1,8-cineole to a mixture of 2!- and 2"-hydroxy-1,8-cineole and
2-keto-1,8-cineole by Pseudomonas flava (MacRae et al. 1979, Carman et al. 1986).
A whole series of metabolites of 1,8-cineole is produced by the gut flora of the brushtail pos-
sum, Trichosurus vulpecula, a herbivorous Australian marsupial which feeds partly on eucalyptus
leaves (see also Chapters 5 and 15). Compounds identified so far (Figure 18.2) include:
9-hydroxy-1,8-cineole and 1,8-cineol-9-oic acid (Flynn and Southwell 1979, Carman and Klika
1992); 7-hydroxy-1,8-cineole (Bull et al. 1993); 2!-hydroxy-1,8-cineole, 2!,9-dihydroxy-
1,8-cineole and 2!,10-dihydroxy-1,8-cineole (Carman et al. 1994); 2!,4-dihydroxy-1,8-cineole
(Carman and Rayner 1994, 1996); 3!-hydroxy-1,8-cineole (Carman et al. 1994, Carman and
Rayner 1996); and 2!,7-dihydroxy-1,8-cineole and 7,9-dihydroxy-1,8-cineole (Carman and
Garner 1996). To the authors knowledge, none of these piperitone and 1,8-cineole metabolites

H3C CH2OH H3C COOH H3C CH3
O O O
CH3 CH3 CH2OH

9-hydroxy- 1,8-cineol- 7-hydroxy-
1,8-cineole 9-oic acid 1,8-cineole
H3C CH3 H3C CH3 H3C CH2OH HOH2C CH3

HO
O O O O
CH3 CH3 CH3 CH3

OH OH OH OH
2!,4-dihydroxy- 2!-hydroxy- 2!,9-dihydroxy- 2!,10-dihydroxy-
1,8-cineole 1,8-cineole 1,8-cineole 1,8-cineole
H3C CH2OH H3C CH3 H3C CH3
O O O
HO
CH2OH CH2OH CH3
OH
7,9-dihydroxy- 2!,7-dihydroxy- 3!-hydroxy-
1,8-cineole 1,8-cineole 1,8-cineole
Figure 18.2 Products of 1,8-cineole metabolism by the brushtail possum worth investigating for
potential applications in medicine or perfumery.
have yet been investigated for potential applications in medicine or perfumery but it would be
of some interest to do so.
To summarise, a large effort has been put into the investigation of the chemical composition
of eucalyptus leaf oils in an attempt to find new uses or sources of them, beyond the traditional
ones. Despite the scientific value of this work, very little of commercial benefit has resulted from
it, the most notable exceptions being the discovery of the E-methyl cinnamate-rich leaf oil of
E. olida and its subsequent commercialisation on a modest scale (as a flavour additive) and the
use of cineole-rich eucalyptus oils as industrial degreasing agents. In the latter case, only time
will tell whether this use can be sustained in view of the present high price of the oils (relative to
alternative solvents).
In order to justify and recoup the substantial financial investment required for the establish-
ment of eucalyptus plantations, both current and planned, new and substantial uses for the oils
will need to be found. Whilst it is not easy, and perhaps unwise, to make predictions for the
future, it is the authors view that the microbiological transformation of readily available euca-
lyptus oil constituents may hold the key to the achievement of these goals, particularly if the
metabolites show pharmacological activity (antibacterial, fungistatic, etc.).

Non-volatile constituents
Rutin
Apart from small amounts of kino resinous exudates of the bark and wood of many Eucalyptus
species the only other non-volatile constituent of eucalyptus foliage which has been produced
commercially is rutin (3,5,7,3&,4&-pentahydroxyflavone-3-rutinoside). Rutin is used medicinally
and its aglycone, quercetin, is a powerful antioxidant. The traditional Australian source of this
compound was E. macrorhyncha although, elsewhere, it was obtained from the flower buds of
Sophora japonica and buckwheat. Australian rutin production fluctuated between 13.5 and 18 t
per year and lasted from the mid-1950s to approximately the end of the 1960s. There are other
eucalypts which contain substantial amounts of rutin in their foliage, notably E. youmanii and
E. delegatensis (Humphreys 1964). Whilst there is virtually no rutin production from eucalypts
today, increased European interest in this medicinal compound, particularly in France and
Germany, might rekindle the industry in Australia.
In E. macrorhyncha the greatest concentration of rutin is found in the youngest leaves, up to 25
per cent on a dry weight basis. However, the overall yields of rutin obtained in commercial oper-
ations were about 10 per cent of dry foliage (Humphreys 1964). Experiments conducted at the
Castle Hill plantation of the Sydney Museum of Applied Arts and Sciences suggested that
E. youmanii might be a better species as overall rutin yields could be as high as 20 per cent (dry
weight) during the summer months (Small 1979). E. delegatensis foliage contains less rutin, 67 per
cent on average. However, this species is also an important timber tree and utilisation of waste
by-product foliage in any new venture would have cost and conservation advantages over, say,
E. youmanii.
Other bioactive non-volatile compounds

Although a great deal of work remains to be done, research carried out since the 1970s has indicated
that the potential for eucalyptus to be used to combat some of the most serious and widespread
illnesses and diseases may rest with some of its non-volatile constituents, rather than with the more
familiar volatile oils. Ghisalberti (1996) and Singh et al. (1999) have drawn attention to this in their
reviews of the non-volatile constituents of eucalypts. In tropical areas where water-borne trematode
infections such as schistosomiasis and fascioliasis are found, it may not even be necessary to isolate
the active constituents in order to take advantage of their properties. Hammond et al. (1994) have
proposed that the natural fall of leaves from Eucalyptus species with molluscicidal properties planted
in appropriate places could effect self-delivery.
Egawa et al. (1974) noticed the almost total absence of microorganisms (fungi, actinomycetes,
bacteria) on the surface of, and inside, the leaves of E. gunnii. They ascribed this to the presence
of three antifungal compounds: gallic acid and two incompletely characterised compounds, a
monoformyl-trihydroxybenzene and a diformyl-trihydroxybenzene previously isolated from this
species by Kobayashi et al. (1972). Several other Eucalyptus species were subsequently found to
contain antifungal compounds, though no attempts were made at their identification (Egawa
et al. 1977).
Since then, a substantial amount of work has been carried out on the isolation and structure
elucidation of novel bioactive metabolites present in the foliage of Eucalyptus species. The stil-
benes polydatin (piceid), polydatin 6'-O-(E)-p-coumarate and rhaponticin from E. rubida all
exhibit attachment-inhibiting activity towards the blue mussel, Mytilus edulis galloprovincialis
(Yamashita et al. 1989, Etoh et al. 1990), and indicate the potential of such compounds as

antifouling agents for protecting ships hulls and other structures in a marine environment.
However, the great majority of the other bioactive metabolites so far identified in eucalypts have
proved to be acylphloroglucinols (Ghisalberti 1996, Singh et al. 1999).
Three phloroglucinol-derived peroxides, G-1, G-2 and G-3, isolated from E. grandis, possess
root growth-inhibiting properties (Crow et al. 1971) whilst grandinol, a derivative of
formylphloroglucinol occurring in E. grandis and E. perriniana, possesses both root growth-
inhibiting and bactericidal properties (Crow et al. 1977, Nakayama et al. 1990). Two new
acylphenones from E. robusta, 2,6-dihydroxy-3,5-dimethyl-4-methoxy-butyrophenone and its
2&-methylbutanoyl homologue, exhibit phosphodiesterase-inhibiting activity (Cheng and
Snyder 1991). Grandinal, a phloroglucinol dimer from E. grandis (Singh et al. 1997), and two
flavonoid glycosides from E. resinifera, resinosides A and B (Hyodo et al. 1992), exhibit blue
mussel attachment-inhibition activity.
Perhaps the most exciting advances in this field relate to the discovery of four groups of novel,
highly bioactive acylphloroglucinol derivatives peculiar to the genus Eucalyptus: the robustadi-
als, sideroxylonals, macrocarpals and euglobals. These have been described earlier in this volume
(Chapter 12) and embrace a number of activities, any or all of which could, in the longer term,
be exploited commercially. Robustadials A and B, with a combined phloroglucinol
monoterpene structure, are antimalarial constituents of E. robusta leaves (Xu et al. 1984, Cheng
and Snyder 1988). The sideroxylonals, dimers of a diformylphloroglucinol moiety isolated from
E. sideroxylon and E. grandis, are antibacterial but also show strong attachment-inhibiting activ-
ity towards the blue mussel; sideroxylonal A is one of the most powerful antifouling agents
known (Satoh et al. 1992, Singh et al. 1996).
The macrocarpals, present in the leaves of E. macrocarpa, E. globulus and E. amplifolia, have a
combined isopentyldiformylphloroglucinolsesquiterpene structure and exhibit a range of bio-
logical activities. They are all strongly antibacterial against Gram-positive bacteria, including
ones which cause dental diseases, and some have recently been found to be active against Gram-
negative bacteria (Murata et al. 1990, Yamakoshi et al. 1992, Osawa et al. 1995, 1996). Some
(macrocarpals A, B, D and G) have been found to inhibit aldose reductase and may find applica-
tion in the treatment of complications resulting from diabetes (Murata et al. 1992). Others (from
E. globulus) are inhibitors of HIV-RTase and have potential in the fight against AIDS (Nishizawa
et al. 1992). The antibacterial and antiviral properties of macrocarpals appear to be due more to
the diformylphloroglucinol moiety than to the different sesquiterpenoid groups attached to it,
although Osawa et al. (1996) have suggested that the antibacterial potency may be regulated by
the structure of the sesquiterpene. Macrocarpals A, B, E, am-1 and H possess blue mussel attach-
ment-inhibiting activity, although it is less than that of sideroxylonal A (Singh and Etoh 1995).
The euglobals are the largest, and structurally most variable, of these four groups of Eucalyptus
metabolites. They are formyl phloroglucinol adducts with either a mono- or a sesquiterpenoid
moiety attached. Euglobals have been isolated from E. globulus (e.g. Kozuka et al. 1982),
E. grandis (e.g. Takasaki et al. 1994a, Umehara et al. 1998), E. amplifolia, E. blakelyi (Takasaki
et al. 1994b), E. incrassata (e.g. Takasaki et al. 1997) and E. tereticornis (Kokumai et al. 1991) but
have been detected in many more species (Chapter 12). Many euglobals show strong inhibition
of Epstein-Barr virus activation induced by 12-O-tetradecanoylphorbol-13-acetate, a tumour-
promoting substance, and this gives rise to hope that they might, in the future, play some role
in cancer prevention (Takasaki et al. 1995).
All the species from which these bioactive metabolites have so far been isolated belong to the
Eucalyptus subgenus Symphyomyrtus (Pryor and Johnson 1971). In view of the potential of these
compounds for disease prevention or treatment, it would be profitable to widen the search to
other species of the subgenus Symphyomyrtus, both within and outside those Sections/Series in

Table 18.4 Distribution of bioactive non-volatile compoundsa in Eucalyptus
Classification of Classification of Species Compound type

Pryor & Johnsonb Chippendale
Section Series Series (no.)
Transversaria Salignae Transversae (no. 42) E. grandis Grandinol, grandinal,

sideroxylonals,
euglobals, peroxides
E. robusta Phenones, robustadials
Annulares (no. 43) E. resinifera Resinosides A, B
Bisectaria Macrocarpae Curviptera (no. 62) E. macrocarpa Macrocarpals
Dumaria Incrassatae Tetrapterae (no. 68) E. incrassata Euglobals
Exsertaria Tereticornes Exsertae (no. 72) E. amplifolia Macrocarpals, euglobals
E. blakelyi Euglobals
E. tereticornis Euglobals
Maidenaria Viminales Viminales (no. 77) E. globulus Macrocarpals, euglobals
E. gunnii ?
E. perriniana Grandinol
E. rubida Stilbenes
E. viminalis Macrocarpals
Adnataria Melliodorae Melliodorae (no. 91) E. sideroxylon Sideroxylonals
a Excluding rutin. See also Figure 12.5, for details of other Sections and Series within Symphyomyrtus in which
euglobals have been detected.
b All within sub-genus Symphyomyrtus.
which these compounds have already been encountered. Table 18.4 shows the distribution of the
different types of bioactive non-volatile compounds referred to above. It includes, for reference,
the alternative classification of Eucalyptus employed by Chippendale (1988), which does not
recognise Symphyomyrtus.
A major drawback in the commercial exploitation of these bioactive metabolites from natural
sources is that the majority of them occur in the buds and foliage of eucalypts in extremely small
amounts (at most 0.1 per cent of fresh plant material, and normally in amounts one or two orders
of magnitude less than this). Huge amounts of eucalyptus foliage would be required to prepare
even small quantities of the desired compound. Handling of such enormous tonnages of plant
material, disposal of waste, and extraction and purification of the final product would be prohib-
itively costly and make the whole operation uneconomic. Synthesis, which has already achieved
some modest success in the laboratory, is probably the only solution to any future large-scale
industrial production.
Concluding remarks
The botanical classification of Eucalyptus has often been fraught with difficulties. Attempts at
providing chemical assistance have, on the whole, been unconvincing although there have been
a few exceptions. Brooker and Lassak (1981) showed that E. ovata and E. brookeriana, superfi-
cially very similar, could be distinguished by the chemical characteristics of their leaf oils. The
seedling leaf oils of the Tasmanian and mainland Australian populations of E. delegatensis differ
significantly from each other in their 4-phenylbutan-2-one content (Boland et al. 1982) and this
fact contributed to the separation of the species into two subspecies, delegatensis and tasmaniensis

(Boland 1985). The leaf oils of E. salubris var. salubris and E. salubris var. glauca were sufficiently
different from each other to suggest that they might be different species (Brophy and Lassak
1991). Independent of this work the variety glauca was separated from E. salubris and designated
E. ravida ( Johnson and Hill 1991). However, Carmans (1992) attempt at producing a computer
program which would show that a unique compound could be assigned to each Eucalyptus
species was of little assistance as the great majority of Eucalyptus species contain the same com-
pounds. Furthermore, it did not take into account the existence of chemical variants within the
same species.
A novel and fundamental approach is being taken at the present time with the whole family
Myrtaceae, including, of course, Eucalyptus, by far the largest of its genera: DNA sequencing
studies are being undertaken (Ladiges et al. 1995). The results of these studies will no doubt
point to new relationships within the genus and indicate new directions for future chemical
research and the search for useful bioactive compounds.
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Appendices

Appendix 1. Sources of eucalyptus seed
The Australian Tree Seed Centre in Canberra is a national and international tree seed bank with
a focus on Australian trees and shrubs. The Centre supplies authenticated seed for research and
tree improvement programmes, together with advice on species and provenance selection and
other information. A leaflet giving details of Australian private seed suppliers is available from
the Centre or the information may be obtained from their Internet website:
Australian Tree Seed Centre

CSIRO Forestry and Forest Products
PO Box E4008
Kingston
ACT 2604
Australia
Tel.: !61-2-6281 8211
Fax: !61-2-6281 8266
E-mail <atsc@ffp.csiro.au>
Website: www.ffp.csiro.au/tigr/atscmain/index.htm
The website also has a searchable seed list which gives details of species and provenances
available.
Many of the seed suppliers listed specialise in eucalypts and some offer bulk or individual tree
collections from specified provenances. Catalogues and price lists are available from suppliers on
request. The Centre points out that there is no tree seed certification scheme in Australia and
recommend that
the purchaser ascertain details of the seed origins before entering into any purchase agree-
ment. The minimum details which might be expected are the precise locality of collection
including latitude and longitude coordinates, altitude of the collecting site, year of harvesting
and number of trees sampled.
Details are also provided of three State Government seed sources (Queensland, Tasmania and
Western Australia).

Appendix 2. Estimates of eucalypt
plantations worldwide
The estimates for the areas of eucalyptus plantations given below (Table A2.1) are taken from
two sources, Davidson (1995) and FAO (unpubl.). Much of Davidsons data is drawn from FAO
sources, which has also been published (Pandey 1995) and provides data up to 1990. The second
source is data made available by FAO in early 1999 which gives the position in 1995; it is based
on further, unpublished reports by Pandey for FAO.
The intention, here, is simply to give some quantitative indication of the extent to which
eucalypts have been planted worldwide. In theory, the amount of waste biomass that is avail-
able for purposes other than that for which the trees are planted, particularly waste leaf, is vast
and constitutes a massive reservoir of potential for utilisation. In practice, of course, many of the
species planted are not oil-bearing ones or ones which might be sources of other commercially
useful medicinal or aromatic compounds. Even where the main species planted has a proven
track record in terms of, say, oil production such as the large plantings of E. globulus in Chile,
Portugal and Spain the size of the industry is not commensurate with the size of the resource.
The economics of production are not favourable when compared with prevailing prices.
Nevertheless, costs and prices do not remain static and conditions in the future may make
production of by-products more attractive.
An indication in Table A2.1 of the main species grown in each country would have been use-
ful but there is insufficient reliable, up-to-date information available to do this. For some coun-
tries the predominant species can be stated with confidence or they have been detailed elsewhere
in this book, for example, E. globulus in Chile, Portugal and Spain, E. camaldulensis in Nepal,
Thailand and Vietnam, Eucalyptus hybrid in India, E. grandis in South Africa, etc. But for many
countries this is not the case and it could be misleading to second guess or use out-of-date
information.
The estimates given below should be treated with caution. Davidson (1995) emphasises that
the majority of figures are approximate and reliability varies. The later FAO data (unpubl.)
contain reduction factors to be applied to the primary data shown in the third column of
Table A2.1; the more reliable the data are, the nearer the factor is to 1.0. For Central and South
America the factor for the region is approximately 0.88, for Africa it is about 0.84 and for Asia
it is approximately 0.64. Worldwide, the total area of eucalypts could be as much as 25 per cent
less than the figures in column three of the table indicate, caused in large part by the uncer-
tainty in the area for India. Estimates given in Chapters 8 and 11 for the areas of eucalypts in
China and India, respectively, are significantly higher than those given here, illustrating, again,
the difficulty of acquiring reliable data. For India, and some other countries, eucalypts may not
be planted in blocks that enable the trees to be included in the definition of plantations for
counting purposes. A later FAO source (Brown 2000) gives figures for the eucalyptus plantation

Table A2.1 Estimates of eucalypt plantations worldwide
Region/Country Area of eucalypts (000 ha) a
1990 1995
Total 13,414 14,619

Of which:
Africa
Algeria 30 39
Angola 135 128
Benin 6
Burkina Faso 7 14
Burundi 40 42
Cameroon 13 12
Cape Verde 2
Central African Rep. 2
Chad 1 2
Comores 1
Congo 35 48
Congo, Dem. Rep.b 20 12
Ethiopia 95 145
Gabon 2 3
Ghana 14
Kenya 17 17
Lesotho 3
Libya 26
Madagascar 130 151
Malawi 30 24
Mali 5 14
Mauritius 3 4
Morocco 200 187
Mozambique 14 14
Namibia 1
Niger 2 3
Nigeria 11 13
Rwanda 60 124
Senegal 40 52
Sierra Leone 2
South Africa 538 557
Sudan 23 76
Swaziland 32
Tanzania 25 4
Togo 10 19
Tunisia 42 35
Uganda 10 3
Zambia 26 7
Zimbabwe 30 10
Total Africa 1637 1805
Asia
Bangladesh 31
China, PR 670 663
India 4800 5063
Indonesia 80 99
Laos 3
Malaysia 8 9
Myanmar 25 49
Nepal 5 11

Table A2.1 (Continued)
Region/Country Area of eucalypts (000 ha)a
1990 1995
Pakistan 29 210
Philippines 10 177
Sri Lanka 45 35
Taiwan 4
Thailand 62 130
Vietnam 245 792
Total Asia 5983 7272
Pacific
Australia 75 160
New Zealand 22
Papua New Guinea 10 15
Solomon Islands 3
Total Pacific 107 178
North America
USA 110
Total N. America 110
Caribbean
Cuba 35 47
Haiti 2
Total Caribbean 37 47
Central America
Costa Rica 10 9
El Salvador 2 1
Guatemala 6 10
Honduras 1
Mexico 38
Nicaragua 6 6
Total C. America 63 26
South America
Argentina 236 249
Bolivia 15
Brazil 3617 3123
Chile 180 245
Colombia 31 60
Ecuador 44 66
Paraguay 8 7
Peru 211 314
Uruguay 160 278
Venezuela 70 71
Total S. America 4557 4428
Mediterranean
Israel 10
Italy 40
Portugal 500 403
Spain 350 460
Turkey 20
Total Mediterranean 920 863
a Source figures rounded to nearest 1000 ha.
b Democratic Republic of Congo, formerly Zaire.
Indicates no estimate given in source data.

resources of India and Brazil of 3.1 and 2.7 million ha, respectively, that is, lower than the fig-
ures in Table A2.1, although 1995 is still used as the basis for the estimates.
Despite these reservations and difficulties the data in Table A2.1 represent the best quantita-
tive picture available of the worlds eucalypt plantings.
References
Brown, C. (2000) The Global Outlook for Future Wood Supply from Forest Plantations, FAO Global Forest
Products Outlook Study Working Paper Series, GFPOS/WP/03, Food and Agriculture Organization of
the United Nations, Rome.
Pandey, D. (1995) Forest Resources Assessment 1990: Tropical Forest Plantation Resources, FAO Forestry Paper

Appendix 3. Advice to a prospective new
producer of eucalyptus oil or
other leaf extractive1
To anyone contemplating the production of eucalyptus oil or any other leaf isolate or
extractive for the first time, there are a number of points which have been discussed or alluded
to in the main body of the book which, in an industrial profile, bear repeating here. They apply
whether the extractive is intended for the domestic market or for export.
Firstly, before undertaking a detailed technical and financial appraisal the intending producer
needs to ascertain the market for the product or, in the case of eucalyptus oil, the type(s) of oil to
be produced. This will require an up-to-date assessment of the domestic, regional and inter-
national markets. For the cineole-containing, medicinal type of oil the biggest one in volume
and value terms the price of Chinese 80 per cent oil will be an important indicator of the sort
of price levels with which the new producer will have to compete.
Someone contemplating production of eucalyptus oil or other leaf extractive in a developing
country may be prompted to do so by the existence of a ready source of suitable waste leaf, that
is, leaf which is available from an operation in which eucalypts are being grown primarily for
their wood. Eucalyptus globulus, grown in Portugal for pulp production, but whose leaves yield a
medicinal type of oil, and E. citriodora, grown in Brazil for charcoal production, and whose leaves
yield a perfumery oil, are examples of eucalypts which are utilised in this way. But it is vital to
the success of this type of operation that the logistics of collection are adequately considered.
The distillery or extraction facility should not be sited too distant from the source of leaf and the
security and continuity of supply of leaf should be assured. Although the landowners where the
trees are grown may be happy to be rid of the foliage and not impose any great price on its
removal, it should not be regarded as a near zero-cost raw material for the distiller. Leaf collec-
tion and transportation costs are a major part of the overall costs of such an enterprise.
If intending producers do not wish to be dependent on others for waste leaf then they may
decide to grow their own, multipurpose trees from which waste leaf can be obtained. Besides
having control over the supply of leaf to the distillery or factory, such a situation means that they
are not reliant on one product only for a source of income. E. smithii in southern Africa is an
example of a dual-purpose eucalypt which has been grown simultaneously for timber and oil
production.
Alternatively, the trees may be grown specifically for oil (or other leaf extractive) and the leaf
repeatedly harvested under a short-rotation coppice system of management. Harvesting of the
leaf on a 1220 month cycle may provide a year-round supply of material for distillation or
extraction. Intensive cultivation is necessary and a combination of high biomass (leaf ) and high
oil or extractive yield from the leaf is desirable. Correct species (and provenance) selection is,
therefore, vitally important. Having regard to the species of eucalypt that may already be used
1 Adapted from Coppen and Hone (1992) by permission of the Natural Resources Institute, University of Greenwich.

by others, information should be sought on their suitability for local conditions. Field trials
should then be established to determine growth and product characteristics for a number of
them, including different provenances, if possible. If selected or superior seed is available then
this should be tested. It is only by such means that a reasonable idea of oil or extractive yield on
a per hectare per year basis can be obtained and, therefore, the likely returns on investment.
E. smithii and E. dives in South Africa, E. globulus, E. citriodora and E. staigeriana in South America,
and E. polybractea in Australia are examples of eucalypt species grown specifically for oil.
The advantages to be gained from giving adequate attention to selection of seed for planting
cannot be over-emphasised. Over-hasty planting of a species or provenance which is unsuited to
local conditions, or does not produce an oil or extractive of acceptable quality or yield, will result
in failure.
The distillery or factory, too, is important and due regard should be given to its design,
construction and operation if, and when, a decision is made by the intending producer to com-
mence investment. In the case of oil production, hard-won gains in oil yield in the selection of
planting stock may be lost by poorly designed equipment or poor distillation practice.
The possibility of generating extra revenue from the production process by making use of
waste by-products should not be ignored. Wood left over from harvesting leaf, as well as the
spent leaf from the processing, are potential sources of such income.
Product quality, particularly composition in the case of an oil, should be determined by a
public analyst or other competent organisation. For medicinal oils the crude oil is usually recti-
fied before sale to the consumer and if this is not to be done by the new producer himself then it
is to a rectifier (who may be another, larger producer) that he should turn first for an opinion on
his oil. A crude medicinal oil should probably have a 1,8-cineole content of 65 per cent or higher
for the rectifier to consider purchasing it. In the case of E. citriodora oil, it should contain at least
65 per cent citronellal.
Ennever (1967) has described the problems and pitfalls associated with marketing essential
oils, either new ones, or existing ones being offered by new producers. The trend in commerce
today is one of globalisation and mergers, with many of the largest flavour and fragrance compa-
nies seeking security of supply by establishing production bases in China and elsewhere. The
plethora of middlemen which traditionally characterised the essential oils industry is less true
than it once was and this may make some of Ennevers comments appear less relevant. However,
some of the advice he gave then, which ends on an encouraging note, is still relevant today.
He observed that
The production of essential oils calls for the utmost patience and the closest possible supervision
at all stages . General merchant houses, banks, agents, brokers, dealers, public warehouses
and public analysts have all, to a greater or lesser extent, become participants in the marketing
and distribution of essential oils. In theory, all these may appear unnecessary, but, in well
proven practice, all have a valuable function in the process of channelling the established oils
from the point of production to the point of use . Marketing, as well as producing, essential
oils is likely to prove very trying for the new producer and much patience, understanding and
confidence will be needed for both. Given these, the production of some essential oils can be
profitable and there is abundant evidence to support this claim.
References
Ennever, W.A. (1967) Marketing essential oils. Trop. Sci., 9, 136143.

Appendix 4. Composition of some
commercially distilled
eucalyptus oils
The data below (Tables A4.1 and A4.2) are from Coppen (unpubl.). The samples were acquired
during visits by the author to commercial eucalyptus distilleries in Portugal, Spain, Brazil,
Australia, South Africa, Swaziland and Zimbabwe during 1990/91. All the samples are freshly
produced crude oils from the primary distillation of leaf, that is, before any rectification has
taken place.
Gas chromatographic analysis was performed using a 20 m ! 0.25 mm fused silica capillary
column coated with a Carbowax 20M-type stationary phase and temperature programming
75225C at 4C/min.
Table A4.1 Composition of some medicinal, cineole-rich eucalyptus oils (per cent relative abundance)
E. globulus E. globulus E. globulus E. polybractea E. radiata E. radiata E. smithii E. cinerea

Portugal Spain Brazil Australia Australia South Africa Swaziland Zimbabwe
Isovaleraldehyde 00.2 00.1 01.3 00.1 01.4 01.2

"-Pinene 14.5 20.1 11.2 01.9 04.2 03.4 08.9 09.8
"-Fenchene tr tr tr tr tr tr tr
Camphene 00.1 00.1 00.1 tr tr tr 00.1 00.1
#-Pinene 00.4 00.5 00.5 00.4 00.8 00.8 00.4 00.2
Sabinene tr? tr? tr? 00.3 00.9 01.0
Myrcene 00.2 00.3 00.4 00.2 01.5 01.5 00.5 00.3
"-Phellandrene 00.2 00.4 00.2 00.1 00.3 00.5 00.4 00.8
"-Terpinene tr 00.1 tr tr 00.3 00.4 tr 00.1
Limonene 01.4 01.0 01.7 00.5 2.0 06.5 07.2 06.9
1,8-Cineole 66.8 59.4 73.6 89.7 70.8 65.2 72.2 62.5
$-Terpinene 01.0 00.6 01.2 00.2 00.7 01.0 01.0 00.3
trans-#-Ocimene 00.1 00.1 00.1 tr tr tr
p-Cymene 02.3 01.2 01.7 01.6 00.4 00.7 01.9 00.8
Terpinolene 00.1 00.3 01.1 00.1 00.2 00.2 00.1 00.2
p-Cymenene 00.1 00.1 00.1 tr? tr?
Linalool tr tr? 00.3? 00.4? 00.1 00.1
Pinocarvone 00.5 00.4 00.2 tr tr tr
Terpinen-4-ol 00.5 00.1 00.5 00.8 01.6 01.6 00.5 01.1
Aromadendrene 02.2 04.6 00.3 00.1? tr tr 00.1 00.3
Alloaromadendrene 00.6 00.9 00.1 tr? 00.1 tr tr 00.2
trans-Pinocarveol 01.3 00.9 01.0 00.2 tr 00.1 00.1 00.1
%-Terpineol 00.1 tr 00.1 00.1 00.2 00.2 00.2 00.2
"-Terpineol 02.6 03.0 01.0 00.5 11.5 11.0 02.1 08.0
"-Terpinyl acetate 03.1
Viridiflorol 00.1 00.1 tr tr? tr? tr 00.1?
Spathulenol tr tr tr tr? tr? tr? tr 00.1?
$-Eudesmol 00.1 tr tr? tr? 00.1 tr?
(Continued)

Table A4.1 (Continued)
E. globulus E. globulus E. globulus E. polybractea E. radiata E. radiata E. smithii E. cinerea

Portugal Spain Brazil Australia Australia South Africa Swaziland Zimbabwe
Agarospirol tr? tr? tr? tr? 00.1 tr?

"-Eudesmol 00.2 tr tr tr? tr? 00.3 tr?
#-Eudesmol 00.3 00.1 tr tr? tr? 00.5 tr?
Others 04.1 05.6 03.6 03.2 04.2 05.5 01.8 03.5
tr &trace ('0.05 per cent).

? Indicates that peaks identity has not been confirmed by GC-MS.
Table A4.2 Composition of some eucalyptus oils used in perfumery or as sources of

chemical isolates (per cent relative abundance)
E. citriodora E. staigeriana E. dives

Brazil Brazil South Africa
"-Pinene 00.2 03.1 04.3

#-Pinene 00.6 01.2 tr
Sabinene 00.1 00.1 00.1
Myrcene 00.2 00.9 02.0
"-Phellandrene 02.3 30.6
"-Terpinene 00.2 01.8
Limonene 00.2 26.8 00.4
#-Phellandrene 03.1
1,8-Cineole 00.4 03.3 ?
cis-#-Ocimene 00.1 00.2 00.1?
$-Terpinene 00.1 02.6 01.7
trans-#-Ocimene tr 00.2
p-Cymene 00.8 02.9
Terpinolene 00.1 10.8 03.0
6-Methyl-5-hepten-2-one 00.2
2,6-Dimethyl-5-heptenal 00.1
p-Cymenene 00.3 00.1
Citronellal 81.5 00.2
Linalool 00.4 01.3 00.9
Isopulegol 01.9
Pulegol 03.7
#-Caryophyllene 00.2 00.2 00.4
Terpinen-4-ol 00.8 04.3
Citronellyl acetate 00.4 00.3
Neral tr? 09.6
Methyl geranate tr? 04.7
"-Terpineol 01.1
Piperitone tr 40.9
Germacrene B 03.1
Geranial tr? 12.5
Geranyl acetate tr? 04.6
Citronellol 06.5 00.5
Nerol 00.1 01.4
Geraniol 00.3 04.7
Others 02.9 03.1 02.3
tr &trace ('0.05 per cent).

? Indicates that peaks identity has not been confirmed by GC-MS.

Appendix 5. Quality criteria and
specifications of
eucalyptus oils
Introduction
Given the variability that can exist for eucalyptus oils, even when they are produced from the
same botanical source, there is clearly a need for some sort of standard or specification for oils of
commerce so that the buyer, or prospective buyer, knows what he can expect when he makes a
purchase. The larger commercial producers, particularly those which export their oil, usually
offer their own specifications and, if requested, these can be passed on by dealers or importers to
their own customers. Once the link between producer and buyer is firmly established, and the
latter has seen that successive consignments meet the needs and expectations of his end-user cus-
tomers, subsequent orders can be placed on the basis of mutual trust. The end user or formulator
will usually monitor purchases by undertaking appropriate quality control tests. For medicinal
oils, 1,8-cineole content (among other things) is important, while for perfumery oils the content
of some specific constituent such as citronellal and/or the overall fragrance characteristics are
important.
National and international standards exist which formalise certain of these quality criteria
and, if they choose to, producers can assert that their oil meets such standards while buyers can
demand that what they purchase does so. For the low-volume, specialised types of oil, published
standards do not exist and compliance with quality requirements is a matter between the buyer
and seller.
Any prospective new producer of eucalyptus oil must be aware of the standards which exist for
the type of oil he is hoping to produce. Some indication of the parameters which are quantified
for the different types of oil is given below but full details should be obtained from the relevant
national or international standards organisation or pharmacopoeia. Specifications are also subject
to change and the current position should be checked with the same institutions. Trade and
other organisations should also be able to offer advice. The addresses of many of these bodies are
given in Appendix 7.
Medicinal oils
Specifications of standards organisations

The International Standardization Organization (ISO) is a worldwide federation of national stan-
dards institutes and has issued three standards covering different types of cineole-rich eucalyptus
oil (ISO 1974, 1980, 1983). The standards specify those characteristics of the oils which can be
quantified with a view to facilitating the assessment of their quality; they cannot adequately
define those properties which involve a buyers subjective judgement, such as odour. In many

cases the ISO standards are formally approved by member bodies of individual countries and go
on to be adopted as national standards. Australia has produced its own standards for eucalyptus
oil (referred to below) but other eucalyptus oil producers such as Brazil and South Africa
have not.
For all three ISO standards, a minimum cineole content or range of values is specified,
together with ranges of values for relative density, refractive index and optical rotation, and the
solubility in ethanol. ISO 770:1980 and ISO 4732:1983 refer to steam-distilled oils from
E. globulus. The first of these stipulates a minimum cineole content of 70 per cent while the sec-
ond describes the three types of rectified oil which are commonly available from Portugal:
70/75, 75/80 and 80/85 per cent cineole. The third standard, ISO 3065:1974, specifies require-
ments for Australian eucalyptus oil of 8085 per cent cineole content and defines the
origin of the oil simply as appropriate species of Eucalyptus of Australian origin.
Standards Australia has recently published revised specifications for Australian eucalyptus oil
(SA 1998). AS 2113.1-1998 lays down requirements for oil containing 7075 per cent cineole
and supersedes AS 2113-1977, while AS 2113.2-1998 refers to oil containing 8085 per cent
cineole and supersedes AS 2115-1977. Both detail physico-chemical requirements, with cineole
contents in the defined ranges, as before, but the revised versions contain some additional mate-
rial, including a gas chromatographic profile of the oils, a table showing the constituents and an
appendix with information on flash points.
An Indian standard, IS 328:1992, exists for Oil of Eucalyptus Globulus, although the
description of the oil allows it to be distilled from other cineole-containing species of eucalyp-
tus as well as E. globulus (BIS 1992). It has different ranges of values for relative density, refrac-
tive index and optical rotation to those of the analogous ISO standard and, importantly, a lower
requirement for cineole: 60 per cent instead of 70 per cent.
The designations of the above standards, the minimum cineole content (or range of values)
demanded by them, and the designations of the ISO standards which describe the methods of
analysis to be followed, are given in Table A5.1. The minimum cineole content specified in the
pharmacopoeia and food specifications referred to below are also included.
Pharmacopoeia specifications
Although conveniently termed medicinal eucalyptus oils, the standards described above make
no reference to the use to which the oils are put. As noted below, some cineole-rich oils are used
in foods. For strictly medicinal purposes the oils must comply with national or international
pharmacopoeias. Compliance with the British Pharmacopoeia (BP) specification is often cited by
producers and this states that eucalyptus oil must contain not less than 70.0 per cent 1,8-cineole
(BP 1998). The specification is identical to that of the European Pharmacopoeia (EP 1998). The
oil is defined as being obtained from various species of eucalyptus rich in 1,8-cineole but goes
on to say that the species used are Eucalyptus globulus Labillardire, Eucalyptus fruticetorum
F. von Mueller (Eucalyptus polybractea R.T. Baker) and Eucalyptus smithii R.T. Baker. In addition
to giving a minimum cineole content, the specification lays down ranges for optical rotation,
relative density and refractive index and states the solubility of the oil in alcohol. It also
describes chemical tests which are to be carried out. These are intended to ensure that levels of
aldehydes and phellandrene which might be present are below certain limits and these additional
requirements distinguish the BP specification from ISO 770:1980 with which it is otherwise
very similar. Several of the crude medicinal oils contain small amounts of isovaleraldehyde (see
Appendix 4) and rectification serves both to increase their cineole content and to remove this
undesirable constituent, thereby enabling them to meet BP standards.

Table A5.1 List of standards and specifications for cineole-rich eucalyptus oils, together with requirements
for cineole content and methods for the determination of parameters referred to in the ISO
standards
Type/Designation Type of oil/Analytical method Cineole content (%)a
Standards
ISO 770:1980(E) E. globulus min. 70
ISO 4732:1983(E) Rectified E. globulus, Portugal: 70.074.9, 75.079.9, 80.085.0
7075%, 7580%, 8085%
ISO 3065:1974(E) Australian, 8085% 8085
AS 2113.1,2-1998 Australian, 7075%, 8085% 7075, 8085
IS 328:1992 E. globulus min. 60
Pharmacopoeias
British Eucalyptus oil min. 70.0
European Eucalyptus oil min. 70.0
Indian Eucalyptus oil min. 60
Chinese Oleum eucalypti min. 70
Food Chemicals
US Eucalyptus oil min. 70.0
Methods
ISO 212:1973 Sampling
ISO 356:1996 Preparation of test samples
ISO 1202:1981 Determination of 1,8-cineole contentb
ISO 279:1981 Determination of relative density
ISO 280:1976 Determination of refractive index
ISO 592:1981 Determination of optical rotation
ISO 7359:1985 Gas chromatography on packed columns
ISO 7609:1985 Gas chromatography on capillary columns
ISO 1271:1983 Determination of carbonyl value (free
hydroxylamine method)c
a On m/m or w/w basis.

b Measures the crystallisation temperature of a mixture of the test oil and o-cresol; the temperature depends on the
1,8-cineole content of the oil.
c Required for E. citriodora oil.
Other national pharmacopoeias that lay down standards for eucalyptus oil include those of
Austria, Belgium, Brazil, the Peoples Republic of China, France, Germany, Hungary, India,
Italy, Japan, Netherlands, Portugal and Switzerland. Although contained in the 21st (1985) edi-
tion of the United States Pharmacopoeia (16th edition National Formulary), eucalyptus oil was
deleted from the 22nd/17th edition (1990) and remains absent from the 23rd/18th edition
(1995). The Indian Pharmacopoeia defines eucalyptus oil in a similar way to the BP and has
similar or identical values for the physico-chemical data, but, like the Indian standard referred to
above (BIS 1992), it has a minimum cineole requirement of 60 per cent rather than 70 per cent
(IP 1996). Like the BP it has tests for aldehydes and phellandrene.
The Pharmacopoeia of the Peoples Republic of China (PPRC 1992) demands a minimum
cineole content of 70 per cent for eucalyptus oil but allows it to be produced from a non-eucalypt
species (by steam distillation from the plants of Eucalyptus globulus Labill. (Fam. Myrtaceae),
Cinnamomum camphora (L.) Sieb. (Fam. Lauraceae) or other plants belong[ing] to the same genus
of these two families). Acceptable ranges for relative density and refractive index are given but,
unlike the BP, no range for optical rotation is specified. A test for the absence of phellandrene is
described and a heavy metals limit of 10 ppm is laid down.

Specifications for use in foods
Cineole-rich eucalyptus oil is sometimes used as a flavouring agent in foods and in the United
States the Food Chemicals Codex (NAS 1996) lays down specifications with which it must
comply. The 1996 version (4th edition) is identical to that in the 1981 3rd edition. The oil is
described as being that distilled from Eucalyptus globulus (FEMA No. 2466) and other species of
Eucalyptus and must contain not less than 70.0 per cent cineole. In addition to specified limits
for specific gravity and refractive index, the oil must pass tests that demonstrate nil (or low)
amounts of heavy metals and phellandrene.
The Food Chemicals Codex also lays down specifications for eucalyptol (FEMA No. 2465),
the trivial name given to the main constituent of medicinal type eucalyptus oil, 1,8-cineole
(synonyms for which include cajeputol and 1,8-epoxy-p-menthane). An infra-red spectrum is
given for identification purposes. Since eucalyptol is a single chemical, the specifications reflect
its physico-chemical properties:
Molecular weight, formula 154.25, C10H18O

Boiling point 176C
Specific gravity (25C) 0.9210.924
Refractive index (20C) 1.4551.460
Optical rotation 0.5 to !0.5
Solidification point minimum 0C
Perfumery oils
Of the perfumery oils, published standards exist only for E. citriodora oil. Other perfumery oils,
such as that from E. staigeriana, are traded on the basis of sample assessment by the buyer.
The international standard for E. citriodora oil, ISO 3044:1997, sets maximum and minimum
limits for relative density, refractive index and optical rotation (ISO 1997). The ranges of values
for all three parameters are slightly different to those given in the previous version of the stan-
dard (ISO 3044:1974). Citronellal content is important and the oil must contain a minimum of
70 per cent carbonyl compounds expressed as citronellal to comply with the standard. In keeping
with the modern trend for standards for essential oils to provide chromatographic information,
ISO 3044:1997 shows typical gas chromatograms obtained on a polar and apolar column in a
separate annex. A second annex provides flash point information.
An Indian standard exists for E. citriodora oil, IS 9257:1993. Physico-chemical data are
slightly different to those given in the ISO standard but the minimum citronellal content
remains 70 per cent (BIS 1993).
The Fragrance Materials Association of the United States (FMA) has a standard for
E. citriodora oil (EOA 130) and this states that the aldehyde content, calculated as citronellal,
should be in the range 6585 per cent. Ranges of values for specific gravity, refractive index
and optical rotation are also prescribed. There is also an FMA monograph for eucalyptol (1991
revision, replacing EOA 288).
Other oils
No published standards exist for oil from E. dives (piperitone variant) and quality criteria are a
matter for agreement between buyer and seller. If the oil is being utilised as a source of piperi-
tone then the content of the latter is usually around 40 per cent or more.

References
BIS (1992) Indian Standard. Oil of Eucalyptus Globulus Specification, IS 328:1992, Bureau of Indian
Standards, New Delhi, India, 4 pp.
BIS (1993) Indian Standard. Oil of Eucalyptus Citriodora Specification, IS 9257:1993, Bureau of Indian
Standards, New Delhi, India, 3 pp.
BP (1998) Eucalyptus oil. In British Pharmacopoeia, Vol. I, British Pharmacopoeial Commission, The
Stationery Office, London, pp. 570571.
EP (1998) Eucalyptus oil. In European Pharmacopoeia, 3rd edn, 1999 Supplement, Council of Europe,
Strasbourg, France, pp. 489490.
IP (1996) Eucalyptus oil. In Indian Pharmacopoeia, Vol. I, Controller of Publication, New Delhi, India,
p. 310.
ISO (1974) International Standard. Oil of Australian Eucalyptus, 80 to 85% Cineole Content, ISO 3065-
1974(E), International Organization for Standardization, Geneva, Switzerland, 2 pp.
ISO (1980) International Standard. Oil of Eucalyptus Globulus, ISO 770-1980(E), International Organization
for Standardization, Geneva, Switzerland, 2 pp.
ISO (1983) International Standard. Rectified Oil of Eucalyptus Globulus Labillardire, Portugal, ISO 4732-
1983(E), International Organization for Standardization, Geneva, Switzerland, 2 pp.
ISO (1997) International Standard. Oil of Eucalyptus Citriodora Hook., ISO 3044-1997(E), International
Organization for Standardization, Geneva, Switzerland, 5 pp.
NAS (1996) Eucalyptus oil. In Food Chemicals Codex, 4th edn, National Academy of Sciences, National
Academy Press, Washington D.C., USA, pp. 138139.
PPRC (1992) Oleum Eucalypti. In Pharmacopoeia of the Peoples Republic of China, English Edition,
Guangdong Science & Technology Press, Guangzhou, China, p. 129.
SA (1998) Oil of Australian Eucalyptus. Part 1: 7075 Percent Cineole, AS 2113.1-1998, and Part 2: 8085
Percent Cineole, AS 2113.2-1998, Standards Australia, Strathfield, Australia.

Appendix 6. Packaging and labelling
requirements for the handling
and transportation of
eucalyptus oils1
Introduction
The production and export of eucalyptus oil (and other essential oils) used to be simply a matter
of producing it to the required quality and transporting it from A to B, with a minimum of doc-
umentation. However, the increasing attention being given worldwide but particularly in
Europe to safety and environmental issues has seen an ever-burgeoning responsibility placed
on the shoulders of producers, processors and importers to see that dangerous substances and
goods are adequately packaged and labelled, and shipped with a much more comprehensive set
of documents. Such measures are designed to ensure the safe handling and transportation of
materials that are actually or potentially dangerous substances. With a few exceptions, the main
risk associated with essential oils is their flammability. In the case of eucalyptus oils, this risk is
different for the cineole-rich medicinal oils and oil from Eucalyptus citriodora.
Legislation
Within Europe, the most important legislation relating to dangerous substances which is rele-
vant to essential oils are Council Directives 67/548/EEC and 79/831/EEC. The regulations relate
to the storage, handling and use of such substances and require, for example, that every package
shows the name and origin of the substance, the appropriate danger symbol (e.g. a flame in a red
diamond indicating a flammable liquid) and standard codes indicating special risks and safety
advice. These codes are of the form Rx (for risks) and Sx (for safety), where x is a number specific
for a particular phrase. Prefixes Xi, Xn or T are added for substances which present an irri-
tant or other harmful risk or are toxic. Substances deemed to be marine pollutants require
special labelling.
None of the eucalyptus oils of international trade are perceived to present health or environ-
mental risks and the only labelling required (valid in 1999) is R10 for the cineole-rich oils such
as E. globulus. This indicates their flammability and is relevant for all oils with a flash point in
the range 2155C. E. citriodora oil has a flash point of approximately 65C and so does not
require a flammability warning.
Recent legislation pertaining to the aspiration hazard of hydrocarbons (94/69/EC and
96/54/EC) has given rise to the need to label certain of such materials with the risk code R65
1 Adapted from Coppen and Hone (1992) by permission of the Natural Resources Institute, University of Greenwich.
Updated information is drawn from Green (1997) and Protzen (1998), for which both authors are thanked. Additional
information provided by M. Irvine and D. Moyler is acknowledged. Aspects of legislation relating to consumer
products containing eucalyptus oil are discussed in Chapter 16.

(Harmful; may cause lung damage if swallowed) and the safety phrase S62. This requirement is
now impinging on essential oils and the European Flavour and Fragrance Association (EFFA)
have decided to apply the R65 class to all essential oils and preparations with a total hydrocar-
bon content of greater than 10 per cent. For eucalyptus oils, the medicinal, cineole-rich ones will
attract an R65/S62 classification but E. citriodora oil will not. It was expected that this labelling
requirement would be enforced during 1999.
In the United States, drums of either of the two types of eucalyptus oil have to be labelled
for worker protection with the phrase May irritate skin and eyes. For transportation
purposes cineole-rich oils are classified as flammable while E. citriodora oil is not classified
(Chapter 16).
Within the European Union there is a special regulation concerning the protection of water
resources, the Water Resources Act. This classifies substances in one of three classes, where
Class 1 represents a weak hazard to water and Class 3 represents a strong hazard. Although so far
only practised and enforced in Germany, the act is likely to be adopted across Europe in due
course. Tests have indicated that eucalyptus oil falls into Class 1.
When dangerous substances are transported they become goods and when conveyed from
one country to another they are subject to international regulations according to the means of
conveyance. In the case of shipment by sea, regulations of the International Maritime Dangerous
Goods (IMDG) code have to be observed. As with dangerous substances, dangerous goods have
to be marked with warning labels.
To warn and inform people who are handling dangerous substances about the potential risks,
Material Safety Data Sheets have been developed for use within the European Union. These
detail the physical, chemical and toxicological properties of the substance in question, together
with measures to be taken in the event of accidental spillage or other exposure, and have to be
provided by importers for all dangerous goods prior to release of the consignment by Customs
from the port of landing, and whenever they are offered for sale, transported and supplied.
Advice and information on these aspects for essential oils is regularly published and updated by
the International Fragrance Association and the International Organisation of the Flavour
Industry. Another example of the way in which such information is compiled and disseminated
is the CHIP (Chemical Hazard Information and Packing Regulations)-List, a database offered by
the British Essential Oil Association which gives information on labelling (hazard symbols and
risk and safety codes required, etc.) for individual essential oils.
Packaging
The risks posed by handling and transportation of dangerous substances are considerably
reduced by proper packaging. In the case of the cineole-rich eucalyptus oils and other essential
oils in which the fire risk is the greatest hazard, this means using UN-approved drums and con-
tainers which meet the specifications for Packing Group III (flammable liquids with a flash
point in the range 2361C and boiling point above 35C). Drums must be metal with a non-
removable head and must have been tested to specified pressure limits. For identification
purposes the appropriate UN code is stamped on the container by its manufacturer.
European Directive 94/62/EC requires a stepwise reduction in the levels of heavy metals in
packaging materials. The final limit is 100 ppm to be achieved by July 2001. In the context
of essential oils this is likely to involve a switch from solvent- to water-based paints used on
drums and is of more concern to companies in importing countries where drums are colour
coded to assist identification during storage and handling rather than those at the point of
origin of the oils.

Documentation
The traditional requirements for documentation which accompanies shipments have been the
commercial invoice, weight and origin certificate, Bill of Lading, insurance documents and a
certificate of the products quality. Nowadays, with the introduction of systems of classification
and labelling has come the need to provide evidence of compliance in shipping documents. The
invoice must now provide information on product identification, the UN product code, its flash
point and any other hazards. For cineole-rich eucalyptus oils UN No. 1169 (extracts, aromatic,
liquid) or No. 1197 (extracts, flavouring, liquid) are applicable, although UN No. 1993
(flammable liquids, non-toxic, not otherwise specified) can be used alternatively.
As indicated earlier, within the European Union importers are obliged to submit Material
Safety Data Sheets for consignments prior to release by Customs. It is also regarded as good com-
mercial practice (and is becoming increasingly common) for the exporters themselves to include
such data along with the other documentation.
Whose responsibility?
Within the European Union, where much of the legislation has been promulgated, it is the
importers of essential oils who are considered to be the producers (since they supply the goods to
the market) and it is they, therefore, who are ultimately responsible for proper classification and
labelling of goods. However, although it may be tempting for producers at origin to feel that
they are absolved from taking the measures indicated above when they are exporting to Europe
and elsewhere, they should recognise, particularly in these days of the global economy, that it
is in their own interests to meet the appropriate packaging and labelling requirements.
Regulations are being increasingly enforced by policing at the point of import and if consign-
ments are found to be lacking in terms of correct packaging, labelling or documentation any
penalties meted out to the importer will have adverse repercussions, in one way or another, for
the producer/exporter.
The regulations discussed above are being continually assessed and revised as new facts or
circumstances come to light; even changes of a general nature may still impinge on eucalyptus
oil. More detailed and up-to-date information than can be given here can be obtained from
national and international transportation authorities, trade associations, international organisa-
tions such as IFEAT, IFRA and IOFI, or the importers themselves. Addresses of some of these
organisations are given in Appendix 7.
References
Green, C.L. (1997) Export packaging and shipment of essential oils: requirements and regulations in the
major markets. Paper presented at UNIDO Essential Oils Conference, Harare, Zimbabwe, November
1997.
Protzen, K.D. (1998) New developments in legislation/regulations for the transportation of essential oils.
In Global Markets: Present and Future, Proc. IFEAT Internat. Conf. Essential Oils and Aromas, London,
November 1998, pp. 260269.

Appendix 7. Useful addresses
Trade associations
British Essential Oil Association (BEOA) Fragrance Materials Association (formerly
15 Exeter Mansions Essential Oil Association of the USA)
Exeter Road Same contact details as for FEMA
London NW2 3UG
UK International Federation of Essential Oils
Tel.: !44-20-8450 3713 and Aroma Trades (IFEAT)
Fax: !44-20-8450 3197 Federation House
6 Catherine Street
Cosmetic, Toiletry and Fragrance Association (CTFA) London WC2B 5JJ
1101 17th Street NW, Suite 300 UK
Washington Tel.: !44-20-7836 2460
DC 20036 Fax: !44-20-7836 0580
USA
Tel.: !1-202-331 1770 International Fragrance Association (IFRA)
Fax: !1-202-331 1969 Rue Charles-Humbert, 8
1205 Geneva
European Flavour and Fragrance Association (EFFA) Switzerland
Square Marie-Louise, 49 Tel.: !41-22-321 3548
1000 Brussels Fax: !41-22-781 1860
Belgium
Tel.: !32-2-238 9905 International Organisation of the
Fax: !32-2-230 0265 Flavour Industry (IOFI)
Same address as for IFRA
Flavour and Extract Manufacturers Association
(FEMA)
1620 I Street NW, Suite 925
Washington
DC 20006
USA
Tel.: !1-202-293 5800
Fax: !1-202-463 8998
Standards organisations
Addresses are given for standards organisations in the major eucalyptus oil producing countries,
together with those in the major markets of France, Germany, Japan, the United Kingdom and
United States. All those listed below are members of ISO and the ISO standards for eucalyptus

oil can be obtained from them, as well as ISO headquarters in Geneva. Some national bodies have
standards for eucalyptus oil which are identical to the ISO ones. A few, such as the Australian
and Indian bodies, issue their own standards.
Other ISO members from whom the ISO standards can be obtained are those in Albania,
Algeria, Argentina, Armenia, Austria, Bangladesh, Belarus, Belgium, Bosnia and Herzegovina,
Bulgaria, Canada, Colombia, Costa Rica, Croatia, Cuba, Cyprus, Czech Republic, Denmark,
Ecuador, Egypt, Ethiopia, Finland, Ghana, Greece, Hungary, Iceland, Indonesia, Iran, Ireland,
Israel, Italy, Jamaica, Kazakhstan, Kenya, Korea (Democratic Peoples Republic of ), Korea
(Republic of ), Libya, Macedonia (former Yugoslav Republic of ), Malaysia, Mauritius, Mexico,
Mongolia, Morocco, Netherlands, New Zealand, Nigeria, Norway, Pakistan, Panama,
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Eucalyptus The Genus Eucalyptus PDF

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Eucalyptus

The Genus Eucalyptus

London and New York

Copyright 2002 Taylor and Francis

Copyright 2002 Taylor and Francis

2 Eucalyptus, water and the environment

3 Eucalypts in cultivation: an overview

4 Genetic improvement of eucalypts: with special reference to

6 Distillation of eucalyptus leaf oils: theory and practice

8 Cultivation and production of eucalypts in the Peoples

Copyright 2002 Taylor and Francis

10 Cultivation and production of eucalypts in South America:

11 Cultivation and production of eucalypts in India:

13 Antimicrobial activity of eucalyptus oils

14 Eucalyptus in insect and plant pest control: use as a mosquito

15 Chemical ecology of herbivory in eucalyptus: interactions

16 Eucalyptus oil products: formulations and legislation

17 Production, trade and markets for eucalyptus oils

18 Research trends and future prospects

Copyright 2002 Taylor and Francis

S.G. Agarwal, Regional Research Laboratory, Jammu-Tawi 180 001, India.

Copyright 2002 Taylor and Francis

Copyright 2002 Taylor and Francis

Copyright 2002 Taylor and Francis

Copyright 2002 Taylor and Francis

1 Eucalyptus coolabah or E. microtheca.

Copyright 2002 Taylor and Francis

Copyright 2002 Taylor and Francis

John J.W. Coppen

Copyright 2002 Taylor and Francis

Copyright 2002 Taylor and Francis

The discovery of the eucalypts

Copyright 2002 Taylor and Francis

Figure 1.1 Numbers of Eucalyptus species published by year.

Copyright 2002 Taylor and Francis

The origins of Eucalyptus

Copyright 2002 Taylor and Francis

Table 1.1 Suggested characters in Protoeucalyptus

Copyright 2002 Taylor and Francis

Taxonomic group Dorsiventral leaves Isobilateral leaves

Red bloodwoods E. polycarpa E. terminalis

Figure 1.3 Axillary inflorescences (E. pyrocarpa).

Classification in the genus Eucalyptus

Copyright 2002 Taylor and Francis

Copyright 2002 Taylor and Francis

Blakella Ghost gums (e.g. E. tessellaris)

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The eucalypt plant

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Copyright 2002 Taylor and Francis

Copyright 2002 Taylor and Francis

Copyright 2002 Taylor and Francis

Figure 1.9 Bark retained forming a rough bole (E. macrorhyncha).

Copyright 2002 Taylor and Francis

Copyright 2002 Taylor and Francis

Figure 1.12 Tessellated bark (E. calophylla).

Copyright 2002 Taylor and Francis

Figure 1.14 Minniritchi bark (E. caesia).

Seeds and germination

Copyright 2002 Taylor and Francis

Seedlings and leaf ontogeny

The adult leaves

Leaf form and coloredness