Professional Documents
Culture Documents
Edited by
John J.W. Coppen
List of contributors
Preface to the series
Preface
PART 1
General aspects
1 Botany of the eucalypts
IAN BROOKER
5 Eucalyptus chemistry
JOSEPH J. BROPHY AND IAN A. SOUTHWELL
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
PART 3
Biological and end-use aspects
12 Chemistry and bioactivity of the non-volatile constituents
of eucalyptus
TAKAO KONOSHIMA AND MIDORI TAKASAKI
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
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
Roland Hardman
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.
General aspects
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.
1800
1600
Number of species published
1400
1200
1000
800
600
400
200
0
1789 1801 1825 1855 1885 1915 1945 1975 1993
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
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.
Subgenera (Pryor and Johnson 1971) Well-known species and species groups
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
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 1.5 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 1.7 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.
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
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.
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.
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.
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 1.18 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.
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.
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.
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.
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
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
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. 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).
References
Baker, R.T. and Smith, H.G. (1915) Eucalyptus australiana, sp. nov. and its essential oil. J. Proc. Roy. Soc.
N.S.W., 49, 514525.
Barlow, B.A. (1981) The Australian Flora: Its Origin and Evolution. In A.S. George (ed.), Flora of Australia,
Vol. 1, Australian Government Publishing Service, Canberra.
Bartle, J.R. (1997) Information Brochure, Farm Forestry Unit, Western Australian Department of
Conservation and Land Management, Perth.
Barton, A.F.M., Cotterill, P.P. and Brooker, M.I.H. (1991) Heritability of cineole yield in Eucalyptus kochii.
Silvae Genetica, 40, 3738.
Blake, S.T. (1953) Botanical contributions of the Northern Territory Regional Survey. I. Studies on north-
ern Australian species of Eucalyptus. Aust. J. Bot., 1, 185352.
Blakely, W.F. (1934) A Key to the Eucalypts, Government Printer, Sydney.
Boland, D.J., Brophy, J.J. and House, A.P.N. (eds) (1991) Eucalyptus Leaf Oils. Use, Chemistry, Distillation
and Marketing, Inkata Press, Melbourne.
Brooker, M.I.H. (1968) Phyllotaxis in Eucalyptus socialis F. Muell. and E. oleosa F. Muell. Aust. J. Bot., 16,
455468.
Brooker, M.I.H. and Kleinig, D.A. (1990) Field Guide to Eucalypts, Vol. 2, South-western and Southern
Australia, Inkata Press, Melbourne.
Brooker, M.I.H. and Lassak, E. (1981) The volatile leaf oils of Eucalyptus ovata Labill. and E. brookerana
A.M. Gray (Myrtaceae). Aust. J. Bot., 29, 605615.
Carr, D.J. and Carr, S.G.M. (1970) Oil glands and ducts in Eucalyptus LHrit. 2. Development and struc-
ture of oil glands in the embryo. Aust. J. Bot., 18, 191212.
Carr, D.J. and Carr, S.G.M. (1980) The Lehmannianae: a natural group of Western Australian eucalypts.
Aust. J. Bot., 28, 523550.
Chippendale, G.M. (1988) Myrtaceae Eucalyptus, Angophora. In A.S. George (ed.), Flora of Australia, Vol. 19,
Australian Government Publishing Service, Canberra.
Coppen, J.J.W. and Hone, G.A. (1992) Eucalyptus Oils: A Review of Production and Markets, NRI Bulletin
56, Natural Resources Institute, Chatham, U.K.
Doran, J.D. and Matheson, A.C. (1994) Genetic parameters and expected gains from selection for monoter-
pene yields in Petford Eucalyptus camaldulensis. New Forests, 8, 155167.
Hill, K.D. and Johnson, L.A.S. (1995) Systematic studies in the eucalypts. 7. A revision of the bloodwoods,
genus Corymbia (Myrtaceae). Telopea, 6, 185504.
Jacobs, M.R. (1955) Growth Habits of the Eucalypts, Commonwealth Government Printer, Canberra.
Johnson, L.A.S. and Blaxell, D.F. (1973) New taxa and combinations in Eucalyptus II. Contributions from
the N.S.W. National Herbarium, 4, 379383.
Johnson, L.A.S. and Hill, K.D. (1990) New taxa and combinations in Eucalyptus and Angophora
(Myrtaceae). Telopea, 4, 37108.
Maiden, J.H. (19031933) A Critical Revision of the Genus Eucalyptus, Government Printer, Sydney.
Milthorpe, P.L., Brooker, M.I.H., Slee, A. and Nicol, H.I. (1998) Optimum planting densities for the pro-
duction of eucalyptus oil from blue mallee (Eucalyptus polybractea) and oil mallee (E. kochii). Industrial
Crops Prods., 8, 219227.
Penfold, A.R. and Morrison, F.R. (1929) The occurrence of a number of varieties of Eucalyptus dives as deter-
mined by chemical analyses of the essential oils. Part 3. J. Proc. Roy. Soc. N.S.W., 63, 7984.
Penfold, A.R. and Willis, J.L. (1961) The Eucalypts, World Crop Series, Leonard Hill, London, and
Interscience, New York.
Pryor, L.D. and Byrne, O.R. (1969) Variation and taxonomy in Eucalyptus camaldulensis. Silvae Genetica, 18,
6471.
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.
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.
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).
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.
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.
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
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.
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.
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).
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
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.
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.
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.
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
References
Attiwill, P.M. and Clayton-Greene, K.A. (1984) Studies of gas exchange and development in a subhumid
woodland. J. Ecol., 72, 285294.
Bands, D.P., Bosch, J.M., Lamb, A.J., Richardson, D.M., van Wilgen, B.W., van Wyk, D.B. and Versfeld,
D.B. (1987) Jonkershoek Forestry Research Centre Pamphlet 384, Dept. Environment Affairs, Pretoria, South
Africa.
Bartle, J. (1994) New horizons for forestry: tree crops for the wheatbelt. Newsletter of the Institute of Foresters
of Australia Inc., 35(2), 47.
Bosch, J.M. and Hewlett, J.D. (1982) A review of catchment experiments to determine the effects of vege-
tation changes on water yield and evapotranspiration. J. Hydrol., 55, 323.
Brookes, J.D. and Turner, J.S. (1964) Hydrology and Australian forest catchments. In Water Resources Use
and Management, Proc. Australian Academy of Sciences Symp., Canberra, 1963, Melbourne University Press,
Melbourne, pp. 390398.
Calder, I.R. (1979) Do trees use more water than grass? Water Services, 83, 1114.
Calder, I.R. (1985) What are the limits on forest evaporation? a comment. J. Hydrol., 82, 179192.
Calder, I.R. (1990) Evaporation in the Uplands, John Wiley & Sons, Chichester, UK.
Calder, I.R. (1992) A model of transpiration and growth of Eucalyptus plantation in water-limited condi-
tions. J. Hydrol., 130, 115.
Calder, I.R. (1994) Eucalyptus, Water & Sustainability. A Summary Report, ODA Forestry Series No. 6,
Institute of Hydrology, Wallingford, UK.
Calder, I.R. (1996) Water use by forests at the plot and catchment scale. Commonwealth For. Rev., 75,
1930.
Calder, I.R. (1998) Review Outline of Water Resource and Land Use Issues, SWIM Paper 3, International
Irrigation Management Institute, Colombo, Sri Lanka.
Calder, I.R. (1999) The Blue Revolution Land Use and Integrated Water Resources Management, Earthscan,
London.
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
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.
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.
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.
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).
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).
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).
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
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).
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
References
Adams, M.A. (1996) Distribution of eucalypts in the Australian landscapes: landforms, soils, fire and
nutrition. In P.M. Attiwill and M.A. Adams (eds), Nutrition of Eucalypts, CSIRO, Australia, pp. 6176.
Adendorff, M.W. and Schn, P.P. (1991) Root strike and root quality: the key to commercial success. In
A.P.G. Schnau (ed.), Intensive Forestry: The Role of Eucalypts, Proc. IUFRO Symp., Durban, September
1991, Vol. 1, Southern African Institute of Forestry, Pretoria, pp. 3038.
Agriculture Western Australia (1996) Western Australian Salinity Action Plan, Government of Western
Australia, Perth.
Anon. (1990) Around the world: Chile. Commonwealth For. Rev., 69, 212.
Arnold, J.E.M. and Dewees, P.A. (eds) (1995) Tree Management Strategies: Responses to Agricultural
Intensification, Oxford University Press, Oxford, UK.
Attiwill, P.M. and Adams, M.A. (eds) (1996) Nutrition of Eucalypts, CSIRO, Australia.
Barros, N.F. and Novais, R.F. (1996) Eucalypt nutritional and fertiliser regimes in Brazil. In P.M. Attiwill
and M.A. Adams (eds), Nutrition of Eucalypts, CSIRO, Australia, pp. 335355.
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.
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
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.
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).
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
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
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
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).
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)
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
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
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.
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.).
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
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
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
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.
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)
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)
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.
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.
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,
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
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).
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).
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.
References
Allard, R.W. (1960) Principles of Plant Breeding, Wiley, New York.
Ammon, D.G., Barton, A.F.M., Clarke, D.A. and Tjandra, J. (1985a) Rapid and accurate chemical deter-
mination of the water content of plants containing volatile oils. Analyst, 110, 917920.
Ammon, D.G., Barton, A.F.M., Clarke, D.A. and Tjandra, J. (1985b) Rapid and accurate determination of
terpenes in the leaves of Eucalyptus species. Analyst, 110, 921924.
Barnes, R.D. (1987) The tree breeding programme in Zimbabwe: plan of work for 1987/88. Oxford
Forestry Institute, Oxford, UK.
Bartle, J. (1994) New horizons for forestry: tree crops for the wheatbelt. Newsletter of the Institute of Foresters
of Australia Inc., 35(2), 47.
Barton, A.F.M., Cotterill, P.P. and Brooker, M.I.H. (1991) Heritability of cineole yield in Eucalyptus kochii.
Silvae Genetica, 40, 3738.
Birks, J.S. and Kanowski, P.J. (1988) Interpretation of the composition of coniferous resin. Silvae Genetica,
37, 2939.
Birks, J.S. and Kanowski, P.J. (1993) Analysis of resin compositional data. Silvae Genetica, 42, 340350.
Borralho, N.M.G., Kanowski, P.J. and Cotterill, P.P. (1992) Genetic control of growth of Eucalyptus
globulus in Portugal. 1. Genetic and phenotypic parameters. Silvae Genetica, 41, 3945.
Brooker, M.I.H., Barton, A.F.M., Rockel, B.A. and Tjandra, J. (1988) The cineole content and taxonomy of
Eucalyptus kochii Maiden & Blakely and E. plenissima (Gardner) Brooker, with an appendix establishing
these two taxa as subspecies. Aust. J. Bot., 36, 119129.
Bryant, L.H. (1950) Variations in oil yield and oil composition of some species of eucalypts and tea trees.
Forestry Commission (Division of Wood Technology) NSW Technical Notes, 4, 610.
Butcher, P.A., Matheson, A.C. and Slee, M.U. (1996) Potential for genetic improvement of oil production
in Melaleuca alternifolia and M. linariifolia. New Forests, 11, 3151.
Coppen, J.J.W. and Jacovelli, P.A. (1992) Results of a sampling study to determine the variability in leaf
oil yield and cineole content in Eucalyptus smithii according to height within a tree and between trees.
Unpubl. report, Natural Resources Institute, Chatham, UK.
Cotterill, P.P. and Dean, C.A. (1990) Successful Tree Breeding with Index Selection, CSIRO, Melbourne.
Cotterill, P.P. and Jackson, N. (1981) Index selection with restrictions in tree breeding. Silvae Genetica,
30, 23.
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,
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.
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
Angophora (17)
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.
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
1
6 2
5 3
O
4
OH
8 (+)--pinene 4
9 10
OH
H H
H H
(+)-aromadendrene 5 ()-globulol 6
Lemon-scented/perfumery oils
CHO CH2OAc
CHO CHO
COOMe
()-piperitone 11 ()--phellandrene 12 E-methyl cinnamate 13
Figure 5.2 Chemical structures of some common constituents of commercial eucalyptus oils.
OH O
OH OH OH
COOMe
CHO
HO OH
MeO OMe
OHC
OH CHO OMe
OH O
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.
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).
()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),
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).
COOH
MeO O
HO
OH O
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
OMe
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)
$-eudesmol (5 total)
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)
bicyclogermacrene (8)
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 )
$-eudesmol (20 total)
0.71.5 #-pinene (30), 1,8-cineole (6), #-, !-, Brophy unpubl.
$-eudesmol (17 total)
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)
#-terpineol, #-, !-, $-eudesmol
E. chlorophylla 0.50.6 limonene, 1,8-cineole (80), Boland et al. (1991)
#-terpineol, globulol
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. 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)
trans-pinocarveol (12)
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)
rich form (total 61)
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)
isobicyclogermacral (28)
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
0.4 dry #-pinene (5), 1,8-cineole (74), trans- Bignell et al. (1996a)
pinocarveol (3)
E. falcata tr 1,8-cineole (11), aromadendrene Bignell et al. (1997d)
(11), trans-pinocarveol (29)
E. famelica 0.5 dry 1,8-cineole (86) Bignell et al. (1997e)
E. fasciculosa tr 1,8-cineole Baker and Smith
(1920)
0.3 dry 1,8-cineole (58), p-cymene (5), Bignell et al. (1995c)
#-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)
trans-pinocarveol (7)
E. forrestiana 3.3 dry #-pinene (31), 1,8-cineole (17), Bignell et al. (1994a)
aromadendrene (7),
bicyclogermacrene (12)
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 )
(47), spathulenol (9)
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)
!-caryophyllene (21),
bicyclogermacrene (13)
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)
1.42.4 #-pinene (11), 1,8-cineole (69) Boland et al. (1991)
2.8 4.0 dry #-pinene (18), 1,8-cineole (55), Li et al. (1996)
globulol (5)
1.8 dry #-pinene (13), 1,8-cineole (41), Bignell et al. (1996f )
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.
E. kessellii 1.1 dry #-pinene (19), 1,8-cineole (16), Bignell et al. (1997d)
!-caryophyllene (11),
aromadendrene (11)
E. kingsmillii 1.3 dry #-pinene (23), 1,8-cineole (31), Bignell et al. (1994c)
bicyclogermacrene (8)
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)
trans-pinocarveol (13)
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.
$-eudesmol (40 total)
1.1 #-pinene (60), 1,8-cineole (7), #-, !-, Brophy unpubl.
$-eudesmol (10 total)
E. lane-poolei 1.0 dry #-pinene (24), 1,8-cineole (51), Bignell et al. (1994c)
trans-pinocarveol (4)
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. 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
sesquiterpenes (1920)
var. heterophylla 0.61.2 #-pinene (36), 1,8-cineole (15), Brophy unpubl.
aromadendrene (6), globulol (13)
0.5 dry #-pinene (13), 1,8-cineole (14), Bignell et al. (1996d)
aromadendrene (19),
bicyclogermacrene (7)
var. platypus 2.1 dry #-pinene (15), 1,8-cineole (24), Bignell et al. (1996d)
aromadendrene (11),
bicyclogermacrene (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)
aromadendrene (15), globulol (5)
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)
bicyclogermacrene (10)
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. 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)
0.4 dry 1,8-cineole (10), p-cymene (25), Bignell et al. (1996a)
palustrol (9)
E. semiglobosa tr #-pinene (36), 1,8-cineole (21), Bignell et al. (1997d)
aromadendrene (6),
bicyclogermacrene (15)
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
0.4 dry #-pinene (14), 1,8-cineole (60), Bignell et al. (1997a)
bicyclogermacrene (5)
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), #-, !-,
$-eudesmol (35 total)
1.01.3 1,8-cineole (26), p-cymene (27), #-, Brophy unpubl.
!-, $-eudesmol (20 total)
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)
aromadendrene (17), trans-
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
(11), bicyclogermacrene (42)
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)
p-cymene (4), spathulenol (6)
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)
trans-pinocarveol (12)
E. subtilior 0.6 1,8-cineole (58), #-, !-, Brophy unpubl.
$-eudesmol (10 total)
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), #-, !-,
$-eudesmol (5 total)
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)
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%).
Theory
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.
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 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.
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)
Table 6.1 Relative extraction times for Eucalyptus species other than
E. polybractea
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.
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)
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.
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
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.
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
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.
To separator
Still
Steam
Oil
Burner
Boiler
Furnace
Hinged lid
Coolant water
Fixed condenser
Oil/water
condensate
Still to separator
Boiler
Steam
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.
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
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.
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.
Figure 6.8 Multi-tubular condenser being used for eucalyptus oil distillation, Australia (photo:
J. Coppen).
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
Condenser
2250 mm
Still End-point
indicator
Oil
out
Condensate
Receiver- water out
Separator
Bench height
700 mm
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
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.
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.
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.
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.
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).
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 7.4 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).
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).
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.
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
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.
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.
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.
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.
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 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
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.
Bartle, J.R., Campbell, C. and White, G. (1996) Can trees reverse land degradation? In Farm Forestry and
Plantations: Investing in Future Wood Supply, Proc. Australian Forest Growers Conf., Mount Gambier,
Australia, September 1996, pp. 6875.
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
Resources Institute, Chatham, UK.
Curtis, A., Southwell, I.A. and Stiff, L.A. (1990) Eucalyptus, a new source of E-methyl cinnamate. J. Essent.
Oil Res., 2, 105110.
Eastham, J., Scott, P.R., Steckis, R.A., Barton, A.F.M., Hunter, L.J. and Sudmeyer, R.J. (1993) Survival,
growth and productivity of tree species under evaluation for agroforestry to control salinity in the
Western Australian wheatbelt. Agrofor. Syst., 21, 223237.
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.
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
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.
Species Province
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
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.
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
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.
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.
Pest Host
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,
E. urophylla " E. grandis
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
Table 8.9 Principal Eucalyptus species exploited for leaf oil in China
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)
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.
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
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.
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.
References
Anon. (1989) ChinaAustralia Afforestation Project at Dongmen State Forest Farm. Technical
Communication No. 40, Queensland Department of Forestry, Brisbane.
Bai, J. (1992) Eucalyptus tree improvement in southern China problems and strategies (in Chinese;
English summary). For. Res., 5, 574580.
Bai, J. (1994) Genetic improvement of tropical Eucalyptus tree species in China. In A.G. Brown (ed.),
Australian Tree Species Research in China, Proc. Internat. Workshop, Zhangzhou, Fujian Province, P.R. China,
November 1992, ACIAR Proceedings No. 48, pp. 3249.
Brown, A.G. (ed.) (1994) Australian Tree Species Research in China, Proc. Internat. Workshop, Zhangzhou,
Fujian Province, P.R. China, November 1992, ACIAR Proceedings No. 48.
Chen, Y., Yang, L., Li, S. and Jiang, Z. (1983) Study on the chemical components of essential oil from the
leaves of Eucalyptus spp. (in Chinese; English summary). Chem. Ind. For. Prods., 3(2), 1631.
Cu, J. (1988) Yunnan the kingdom of essential oil plants. In B.M. Lawrence, B.D. Mookherjee and
B.J. Willis (eds), Flavors and Fragrances: A World Perspective, Proc. 10th Internat. Congr. Essent. Oils Fragr.
Flav., Washington DC, November 1986, pp. 231241.
Historical review
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,
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).
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).
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
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).
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
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)
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
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
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.
Figure 9.3 Recently harvested Eucalyptus dives, showing coppice re-growth from the stump, South
Africa (photo: J. Coppen).
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.
Diseases
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).
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
Figure 9.5 Eucalyptus smithii leaf being packed into stills for distillation, Swaziland (photo:
J. Coppen).
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.
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.
References
Abou-Dahab, A.M. and Abou-Zeid, E.N. (1973) Seasonal changes in the volatile oil, cineole and rutin con-
tents of Eucalyptus camaldulensis Dehn. and E. polyanthemos Schauer. Egypt. J. Bot., 16, 345348.
Atkinson, P.R., Tribe, G.D. and Govender, P. (1991) Pests of importance in the recent expansion of Eucalyptus
plantings in South Africa. In A.P.G. Schnau (ed.), Intensive Forestry: The Role of Eucalypts, Proc. IUFRO
Symp., Durban, September 1991, Vol. 2, Southern African Institute of Forestry, Pretoria, pp. 728738.
Barton, A.F.M., Cotterill, P.P. and Brooker, M.I.H. (1991) Short note: heritability of cineole yield in
Eucalyptus kochii. Silvae Genetica, 40, 3738.
Boland, D.J., Brophy, J.J. and House, A.P.N. (eds) (1991) Eucalyptus Leaf Oils. Use, Chemistry, Distillation
and Marketing, ACIAR/CSIRO, Inkata Press, Melbourne.
Canty, C. (1991) Controlled release granules protect eucalyptus trees from termite attack. In
A.P.G. Schnau (ed.), Intensive Forestry: The Role of Eucalypts, Proc. IUFRO Symp., Durban, September
1991, Vol. 2, Southern African Institute of Forestry, Pretoria, pp. 739748.
Cardoso do V., J. and Proena da C., A. (1968) Essential oil of Eucalyptus macarthuri Deane & Maiden from
Angola (in Portuguese). Garcia de Orta (Lisboa), 16, 423432.
Chalchat, J.C., Muhayimana, A., Habimana, J.B. and Chabard, J.L. (1997) Aromatic plants of Rwanda. II.
Chemical composition of essential oils of ten Eucalyptus species growing in Ruhande Arboretum, Butare,
Rwanda. J. Essent. Oil Res., 9, 159165.
Chisowa, E.H. (1997) Chemical composition of the leaf oil of Eucalyptus macarthurii Dean & Maiden.
J. Essent. Oil Res., 9, 339340.
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
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.
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
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.
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.
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.
Figure 10.1 Eucalyptus citriodora being grown specifically for oil, So Paulo state (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 10.4 Spent eucalyptus leaf from the distillery being loaded onto lorries for return to the fields
to serve as slow-acting fertiliser (photo: J. Coppen).
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.
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
Anon. (1984a) New prospects in eucalyptus production. Chilean For. News ( June), 910.
Anon. (1984b) Eucalyptol to be exported by a Chilean company. Chilean For. News (October), 67.
Anon. (1987) New company appears on the eucalyptus oil scene. Chilean For. News (April), 1314.
Anon. (1991) The fruits of the eucalyptus. Chilean For. News (August), 45.
Argiro, A.I. and Retamar, J.A. (1973) Essential oils from Tucuman province: Eucalyptus citriodora (in
Spanish). Arch. Bioquim. Quim. Farm. Tucuman, 18, 2937.
Baez, C.M., Escobar, R.R., Gonzalez, O.C. and Vasquez, V.O. (1992) Mineral nutrition of Eucalyptus
globulus subsp. globulus plants in relation to yield and quality of cineole (in Spanish). Agricultura
Tecnica Santiago, 52, 475479.
Boland, D.J., Brophy, J.J. and House, A.P.N. (eds) (1991) Eucalyptus Leaf Oils: Use, Chemistry, Distillation
and Marketing, ACIAR/CSIRO, Inkata Press, Melbourne.
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.
Table 11.1 Suitable land types for oil-bearing eucalypts introduced into Indiaa
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.
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.
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,
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.
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.
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
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).
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).
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
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
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
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).
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.
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).
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.
References
Abbasi, S.A. and Vinithan, S. (1997) Eucalyptus: Enduring Myths, Stunning Realities, Rawat Publications,
Jaipur, India.
Agarwal, S.G., Thappa, R.K. and Handa, S.S. (1998) A Novel Single Step Process for the Simultaneous Extraction
of Essential Oils and Rutin from Plant Materials, Indian Patent 113/Del/1998.
Anahosur, K.H., Padaganoor, G.M. and Hedge, R. (1977) Laboratory evaluation of fungicides against
Cylindrocladium quinquiseptatum, the causal organism of seedling blight of Eucalyptus hybrid. Pesticides,
11(6), 44 45.
Bagchee, K. (1953) New and noteworthy diseases of trees in India. The sap and heartrot diseases of
Eucalyptus maculata Hook. var. citriodora Bailey (E. citriodora) due to the attack of Trametes cubensis (Mint)
Sacc. Indian Forester, 79, 341343.
Basu Choudhuri, J. C., Salar Khan, A.M. and Pankajam, S. (1986) Eucalypts their performance and pest
problems. In J.K. Sharma, C.T.S. Nair, S. Kedharnath and S. Kondas (eds), Eucalypts in India Past,
Present and Future, Proc. Nat. Seminar, Peechi, Kerala, January 1984, Kerala Forest Research Institute,
Peechi, pp. 336345.
Bhalla, H.K.L. (1997) Indian Eucalypts and their Essential Oils, Timber Development Association of India,
Dehra Dun.
Bhatia, C.L. (1984) Eucalyptus in India its status and research needs. Indian Forester, 110, 9196.
BIS (1992) Indian Standard. Oil of Eucalyptus Globulus Specification (IS 328:1992), Bureau of Indian
Standards, New Delhi.
BIS (1993) Indian Standard. Oil of Eucalyptus Citriodora Specification (IS 9257:1993), Bureau of Indian
Standards, New Delhi.
Bradu, B.L., Sobti, S.N. and Atal, C.K. (1982) Prospects of rutin (vitamin P) yielding eucalypts in
Himachal Pradesh. In P.K. Khosla (ed.), Improvement of Forest Biomass, Indian Society of Tree Scientists,
H.P. Agric. Univ., Solan, India, pp. 229231.
Champion, H.G. and Seth, S.K. (1968) A Revised Survey of Forest Types of India, Govt. of India, New Delhi.
Chaturvedi, A.N. (1976) Eucalypts in India. Indian Forester, 102, 5763.
Chaudhari, D.C. and Suri, R.K. (1991) Comparative studies on chemical and antimicrobial activities of fast
growing Eucalyptus hybrid (FRI-4 & FRI-5) with their parents. Indian Perfumer, 35(1), 3034.
Chunekar, K.C. and Pandey, G.S. (1988) Bhavprakash Nighantu, Chaukhambha Bharti Academy, Varanasi,
India, p. 827.
Dayal, R. (1987) Occurrence of ursolic acid and related compounds in Eucalyptus hybrid leaves. Curr. Sci.,
56, 670671.
FAO (1981) Eucalypts for Planting, FAO Forestry Series No. 11, Food and Agriculture Organization of the
United Nations, Rome.
Fernandez, R.R. and Suri, R.K. (1981) Studies on the oil of Eucalyptus citriodora Hook. grown at Dehra
Dun. Indian Forester, 107, 243248.
Husain, A., Virmani, O.P., Sharma, A., Kumar, A. and Misra, L.N. (1988) Major Essential Oil-Bearing
Plants of India, Central Institute of Medicinal & Aromatic Plants, Lucknow, India.
IP (1996) Eucalyptus oil. In Indian Pharmacopoeia, Vol. I, Controller of Publication, New Delhi, p. 310.
Jayashree, M.C., Nair, J.M., Deo, A.D. and Ramaswamy, V. (1986) Relative susceptibility of various euca-
lypt provenances to Cylindrocladium blight. In J.K. Sharma, C.T.S. Nair, S. Kedharnath and S. Kondas
(eds), Eucalypts in India Past, Present and Future, Proc. Nat. Seminar, Peechi, Kerala, January 1984,
Kerala Forest Research Institute, Peechi, pp. 395399.
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).
Table 12.2 Antioxidative activitya of leaf wax extracted from some species of Eucalyptus
O O
HO O
O O OH O
4-hydroxytritriacontane-16,18-dione
IC50
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.
CHO CHO
HO OH H HO OH H
OH
OHC OHC
H H
OH OH
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)
CHO
HO OH CHO
CHO HO OH
HO O CHO
CHO
HO O
OH CHO
OHC OH
OH C
OH
O
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).
OHC
OH
robustadial A -isobutyl
robustadial B -isobutyl
CH3 CHO
H3CO OH HO OH
CH2
(H3C)2HCOC COCH2CH(CH3)2
OH OH
robustaol A
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.
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).
C23H30O5 C28H38O5
m/z 386 m/z 454
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).
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).
R2 R2
H
OH OH
CHO H R1
HO HO O
R2
H
OH H OH
O
euglobal-G6 R1 = CHO
euglobal-G5 R2 = COCH2CH(CH3)2
euglobal-G7 R1 = 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
euglobal-G10 R1 = 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
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
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
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
-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).
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)
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.
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
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
Sample Concentrationb
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.
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.
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
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.
References
Amano, T., Komiya, T., Hori, M., Goto, M., Kozuka, M. and Sawada, T. (1981) Isolation and characteriza-
tion of euglobals from Eucalyptus globulus Labill. by preparative reversed-phase liquid chromatography.
J. Chromatogr., 208, 347355.
Aukrust, I.R. and Skattebol, L. (1996) The synthesis of (*)-robustadial A and some analogues. Acta Chem.
Scand., 50, 132140.
Barnabas, C.G.G. and Nagarajan, S. (1988) Antimicrobial activity of flavonoids of some medicinal plants.
Fitoterapia, 59, 508510.
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.
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).
Table 13.1 Antifungal activitya of eucalyptus, rosemary and thyme oils, with composition in terms
of selected constituents (after Benjilali et al. 1984)
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 (""""").
b Relative abundance, %.
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
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
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:
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.
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)
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.
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7782.
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.
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.
Table 14.1 Repellency of the volatile oils of some Eucalyptus species against
mosquitoes, Aedes albopictus
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).
ED90
(l or g product/cm2) (l or g a.i./cm2)
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).
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
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
Insect species Insect name/type Commodity type E. citriodora E. globulus E. camaldulensis E. tereticornis Unknown a
a Species not declared or tests conducted using extracts, oils or isolates, for example, 1,8-cineole.
Table 14.5 Comparative effectiveness of Eucalyptus citriodora and neem oils against Rhyzopertha dominica,
Oryzaephilus surinamensis and Tribolium confusum (after Thakur and Sankhyan 1992)
2 4 6 8 2 4 6 8
Table 14.6 Effectiveness of Eucalyptus citriodora and E. tereticornis leaf oils against Callosobruchus maculatus
and Sitophilus oryzae (after Gakuru and Foua-Bi 1995)
1 2 7 1 2 7
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)
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.
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
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
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.
H
E. camaldulensis
Spathulenol
H
OH COOH
OH
E. viminalis
COOH
O
COOH
OH
OH OH
E. delegatensis OH
OH
E. pauciflora
H OH
4-Phenylbutan-2-one -Eudesmol
H OH OH
-Eudesmol -Eudesmol
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.
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.
(b) Prunasin
CH3 CHO
CH3O OCH3 HO OH
O O
H3C OHC
OCH3 OH
CHO
CHO
HO OH
HO O
OHC OHC
OH
OH
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.
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.
60
50
Dry matter intake
(g . kg0.75 . d1)
40
30
20
10
0
0 1 2 3 4 5
Total essential oils
(%, 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).
50
Dry matter intake
(g . kg0.75 . d1) 40
30
20
10
0
0 1 2 3 4 5
Total essential oils
(%, dry matter basis)
(b) 35
30
Dry matter intake
25
(g . kg0.75 . d1)
20
15
10
0
0 3 6 9 12
Cineole concentration
(%, dry matter basis)
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.
35
30
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).
Copyright 2002 Taylor and Francis
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.
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.
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
Cineole content of oil (%)
(c) 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 (%)
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).
(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).
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.).
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.
References
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In Open Forum and Symp. Conf., Ecological Society of Australia, Hobart, September 1995, p. 26.
Betts, T.J. (1978) Koala acceptance of Eucalyptus globulus Labill. as food in relation to the proportion of
sesquiterpenoids in the leaves. In T.J. Bergin (ed.), The Koala, Zoological Parks Board of NSW, Sydney,
pp. 7585.
Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. (1994) Volatile leaf oils of some south-western
and southern Australian species of the genus Eucalyptus. Part II Subgenus Symphomyrtus, Section
Dumaria, Series Torquatae. Flavour Fragr. J., 9, 167171.
Boland, D.J., Brophy, J.J., Flynn, T.M. and Lassak, E.V. (1982) Volatile leaf oils of Eucalyptus delegatensis
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Boland, D.J., Brophy, J.J. and Fookes, C.J.R. (1992) Jensenone, a ketone from Eucalyptus jensenii.
Phytochemistry, 31, 21782179.
Boland, D.J., Brophy, J.J. and House, A.P.N. (eds) (1991) Eucalyptus Leaf Oils. Use, Chemistry, Distillation
and Marketing, ACIAR/CSIRO, Inkata Press, Melbourne.
Bowyer, R.C. and Jeffries, P.R. (1959) Studies in plant chemistry. I. The essential oils of Eucalyptus caesia
Benth. and E. torquata Luehm. and the structure of torquatone. Aust. J. Chem., 12, 442446.
Bryant, J.P., Chapin, F.S. III and Kleinig, D.A. (1983) Carbon/nutrient balance of boreal plants in relation
to vertebrate herbivory. Oikos, 40, 357368.
Bull, S.D., Carman, R.M., Carrick, F.N. and Klika, K.D. (1993) 7-hydroxy-1,8-cineole and 7-cineolic
acid 2 new possum urinary metabolites. Aust. J. Chem., 46, 441447.
Carman, R.M. and Klika, K.D. (1992) Partially racemic compounds as brushtail possum urinary metabo-
lites. Aust. J. Chem., 45, 651657.
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.
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.
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.
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.
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
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
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
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.
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
3 The Cosmetic, Toiletry and Fragrance Association, the leading US trade association for the personal care products
industry, with more than 500 member companies.
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
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
% 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
Eucalyptus globulus (as essential oil) 0.10
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.
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.
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.
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.
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.
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
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
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.
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.
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
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.
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).
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
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.
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
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.
Source: Eurostat.
a Indicates nil.
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.
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
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
Table 17.8 Volume of exports of eucalyptus oil from Brazil, and destinations, 19922000
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.
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.
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.
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
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.
Bartle, J.R., Campbell, C. and White, G. (1996) Can trees reverse land degradation? In Farm Forestry and
Plantations: Investing in Future Wood Supply, Proc. Australian Forest Growers Conf., Mount Gambier,
Australia, September 1996, pp. 6875.
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.
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.
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.
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.
80
60
40
20
0
0 5 10 15 20 25 30 35
Distillation time (h)
Table 18.1 Influence of distillation time on the composition of eucalyptus oil (in
terms of sesquiterpenoids)
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
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.
Total C10 Total C15 C15/C10 Total C10 Total C15 C15/C10
(%) (%) ratio (%) (%) ratio
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
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
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.
O O O
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.).
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.
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
References
Abbott, P.S. (1989) Commercial eucalyptus oil production. In Proc. Eucalyptus Oil Production Seminar,
Gnowangerup, Western Australia, February 1989, Misc. Publ. 9/89, Agdex 184/500, Dep. Agric.,
Western Australia, pp. 2948, 52.
Ammon, D.G., Barton, A.F.M., Clarke, D.A. and Tjandra, J. (1985) Rapid and accurate determination of
terpenes in the leaves of Eucalyptus species. Analyst, 110, 921924.
Barton, A. (1989) Commercial possibilities for high-cineole Western Australian eucalyptus oil. In Proc.
Eucalyptus Oil Production Seminar, Gnowangerup, Western Australia, February 1989, Misc. Publ. 9/89,
Agdex 184/500, Dep. Agric., Western Australia, pp. 2128.
Barton, A.F.M. and Knight, A.R. (1997) High-cineole eucalyptus oils in degreasing applications. Chem.
Aust., 64(1), 46.
Beckmann, R. (1988) Oil from eucalypts. Ecos, 56, 78, 10.
Bignell, C.M., Dunlop, P.J. and Brophy, J.J. (1997) Volatile leaf oils of some south-western and southern
Australian species of the genus Eucalyptus (Series I). Part XVIII. A Subgenus Monocalyptus.
B Subgenus Symphyomyrtus, (i) Section Guilfoyleanae, (ii) Section Bisectaria, Series Accedentes,
Series Occidentales, Series Levispermae, Series Loxophlebae, Series Macrocarpae, Series Orbifoliae, Series
Calycogonae, (iii) Section Dumaria, Series Incrassatae and Series Ovulares. Flavour Fragr. J., 12,
423432.
Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. (1995) Volatile leaf oils of some south-western
and southern Australian species of the genus Eucalyptus. Part VI Subgenus Symphyomyrtus, Section
Adnataria. Flavour Fragr. J., 10, 359364.
Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. (1996) Volatile leaf oils of some south-western
and southern Australian species of the genus Eucalyptus. Part VII Subgenus Symphyomyrtus, Section
Exsertaria. Flavour Fragr. J., 11, 3541.
Boland, D.J. (1985) Taxonomic revision of Eucalyptus delegatensis R.T. Baker (Myrtaceae). Aust. For. Res., 15,
173181.
Boland, D.J., Brophy, J.J., Flynn, T.M. and Lassak, E.V. (1982) Volatile leaf oils of Eucalyptus delegatensis
seedlings. Phytochemistry, 21, 24672469.
Boland, D.J., Brophy, J.J. and House, A.P.N. (eds) (1991) Eucalyptus Leaf Oils. Use, Chemistry, Distillation
and Marketing, ACIAR/CSIRO, Inkata Press, Melbourne.
Brooker, M.I.H., Barton, A.F.M., Rockel, B.A. and Tjandra, J. (1988) The cineole content and taxonomy of
Eucalyptus kochii Maiden & Blakely and E. plenissima (Gardner) Brooker, with an appendix establishing
these two taxa as subspecies. Aust. J. Bot., 36, 119129.
Brooker, M.I.H. and Lassak, E.V. (1981) The volatile leaf oils of Eucalyptus ovata Labill. and E. brookerana
A.M. Gray (Myrtaceae). Aust. J. Bot., 29, 605615.
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:
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).
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
1990 1995
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.
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.
Davidson, J. (1995) Ecological aspects of eucalypt plantations. In K. White, J. Ball and M. Kashio (eds),
Proc. Regional Expert Consult. on Eucalyptus, Bangkok, October 1993, Vol. 1, Food and Agriculture
Organization of the United Nations, Regional Office for Asia and the Pacific, Bangkok, pp. 3572.
Pandey, D. (1995) Forest Resources Assessment 1990: Tropical Forest Plantation Resources, FAO Forestry Paper
128, Food and Agriculture Organization of the United Nations, Rome.
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.
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
Coppen, J.J.W. and Hone, G.A. (1992) Eucalyptus Oils: A Review of Production and Markets, NRI Bulletin
56, Natural Resources Institute, Chatham, UK.
Ennever, W.A. (1967) Marketing essential oils. Trop. Sci., 9, 136143.
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)
(Continued)
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
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.
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
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.
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.
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.
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.
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
Coppen, J.J.W. and Hone, G.A. (1992) Eucalyptus Oils: A Review of Production and Markets, NRI Bulletin
56, Natural Resources Institute, Chatham, UK.
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.
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
Other organisations
British Pharmacopoeia Commission Singapore 188024
Market Towers Singapore
1 Nine Elms Lane Tel.: !65-433 4435
London SW8 5NQ Fax: !65-337 5256
UK
Tel.: !44-20-7273 0561 Trade Partners UK Information Centre
Fax: !44-20-7273 0566 [Trade statistics and other information]
Kingsgate House
Research Institute for Fragrance Materials (RIFM)
66-74 Victoria Street
2 University Plaza, Suite 406
London SW1E 6SW
Hackensack
UK
NJ 07601
Tel.: !44-20-7215 5444
USA
Fax: !44-20-7215 4231
Tel.: !1-201-488 5527
Fax: !1-201-488 5594
US Food and Drug Administration
E-mail <help@rifm.org>
Office of Generic Drugs
Trade & Investment Information Centre MetroPark North
[Trade statistics and other information] 7500 Standish Place
Singapore Trade Development Board Rockville
230 Victoria Street MD 20855
#07-00 Bugis Junction Office Tower USA
Copyright 2002 Taylor and Francis