© 2017 Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas 16 (1): 26 - 33 ISSN 0717 7917 www.blacpma.usach.cl Artículo Original | Original Article Constituents of essential oils from the leaf, stem, root, fruit and flower of Alpinia macroura K. Schum [Constituyentes de los aceites esenciales de las hojas, tallo, raíz y flores de Alpinia macroura K. Schum] Le T Huong1, Do N Dai2, Mai V Chung1, Doan M Dung3 & Isiaka A Ogunwande4 1 Faculty of Biology, Vinh University, 182-Le Duan, Vinh City, Nghe An Province, Vietnam Faculty of Agriculture, Forestry & Fishery, Nghe An College of Economics, 51-Ly Tu Trong, Vinh City, Nghe An Province, Vietnam 3 Faculty of Chemistry, Vinh University, 182-Le Duan, Vinh City, Nghe An Province, Vietnam 4 Natural Products Research Unit, Department of Chemistry, Faculty of Science, Lagos State University, Badagry Expressway Ojo, P. M. B. 0001, Lasu Post Office, Ojo, Lagos, Nigeria Contactos | Contacts: Do N DAI - E-mail address: daidn23@gmail.com Contactos | Contacts: Isiaka A OGUNWANDE - E-mail address: isiaka.ogunwande@lasu.edu.ng 2 Abstract: This paper reports the chemical constituents of essential oils from the various parts of Alpinia macroura K. Schum (Zingiberaceae) from Vietnam. The essential oils were obtained by hydrodistillation and analysed by means of gas chromatography coupled to Flame ionization detector (GC-FID) and gas chromatography coupled to mass spectrometry (GC/MS). The main constituents of the oils were β-pinene (8.8%-16.4%), 1,8-cineole (5.5%-17.7%), γ-terpinene (5.9%-16.9%), α-pinene (4.5%-8.4%) and β-caryophyllene (1.4%18.6%). Sabinene (9.0%) was identified only in the fruit. Overall, nineteen of the identified compounds are coming to all the essential oils. The chemical constituents of essential oils from the leaf, stem, root, fruit and flower of A. macroura are being reported for the first time and were found to be different from those of other Alpinia oils. Keywords: Alpinia macroura, hydrodistillation, essential oil, monoterpenes, sesquiterpenes Resumen: En este trabajo se presentan los componentes químicos de los aceites esenciales de las distintas partes de Alpinia macroura K. Schum (Zingiberaceae) de Vietnam. Los aceites esenciales se obtuvieron por hidrodestilación y se analizaron por medio de cromatografía de gases acoplada a detector de ionización de llama (GC-FID) y cromatografía de gases acoplada a espectrometría de masas (GC/MS). Los principales constituyentes de los aceites fueron β-pineno (8,8% -16,4%), 1,8-cineol (5,5% -17,7%), γ-terpineno (5,9% -16,9%), α-pineno (4,5% -8,4 %) y β-cariofileno (1,4% -18,6%). Sabineno (9,0%) fue identificado solamente en la fruta. En general, diecinueve de los compuestos identificados están llegando a todos los aceites esenciales. Los componentes químicos de los aceites esenciales de la hoja, tallo, raíz, frutas y flores de A. macroura están siendo reportados por primera vez y se encontró que eran diferentes de las de otros aceites de Alpinia. Palabras clave: Alpinia macroura, hidrodestilación, aceite esencial, monoterpenos, sesquiterpenos. Recibido | Received: June 4, 2016 Aceptado | Accepted: July 2, 2016 Aceptado en versión corregida | Accepted in revised form: July 24, 2016 Publicado en línea | Published online: January 30, 2017 Declaración de intereses | Declaration of interests: The authors wish to thank National Foundation for Science and Technology Development, Vietnam (NAFOSTED) for financial support of this study through the Project Nr. 106-NN.03-2014.23.. Este artículo puede ser citado como / This article must be cited as: LT Huong, DN Dai, MV Chung, DM Dung, IA Ogunwande. 2017. Constituents of essential oils from the leaf, stem, root, fruit and flower of Alpinia macroura K. Schum. Bol Latinoam Caribe Plant Med Aromat 16 (1): 26 - 33. 26 Huong et al. Abbreviation List: v/w- volume by weight; GC-FID Gas chromatography coupled to Flame Ionization Detector; GC-MS- Gas chromatography coupled to mass spectrometry. INTRODUCTION The genus Alpinia from the Zingiberaceae family of plants consists of more than 230 species (Krees et al., 2005). Alpinia macroura is pseudostem plant of about 2-2.5 m high with oblong leaf blades. The labellium are red with yellow margin. The globular fruits are white and are about 2-2.5 cm long. Flowering takes place in August to December while fruiting occurs in November to March of later year. It is native to Vietnam, Thailand, Mianma, Laos and Cambodia (Binh, 2011). The plant is used ethnomedically in the treatment of sores, fever and intestinal infections (Huong, 2016). The authors are not aware of any information on the biological potentials and non-volatile phytochemical constituents on this plant. There are no previous references in literature about the chemical composition of essential oil of this plant from Vietnam or elsewhere and this prompted the present investigation of the volatile constituents of A. macruora. In continuation of an extensive study into the chemical constituents of underutilized flora of Vietnam (Chau et al., 2015; Dai et al., 2016), we report the compounds identified in the essential oils obtained by hydrodistillation of the leaf, stem, root, fruit and flower of A. macruora. MATERIALS AND METHOD Plants collection Leaves, stems, roots, fruits and flowers of A. macroura were collected from Pù Mát National Park, Nghệ An Province, Vietnam, in May 2014. Voucher specimen DND 389 was deposited at the Botany Museum, Vinh University, Vietnam. Plant samples were air-dried prior to hudrodistillation. Essential oils of Alpinia macruora clean and previously weighed sample bottles. The oils were kept under refrigeration until the moment of analyses. Analysis of the essential oils Gas chromatography (GC) analyses of essential oils were carried on Agilent Technologies HP 6890 Plus Gas Chromatograph which was equipped with a flame ionization detector and HP-5MS column. The dimension of the column is 30 m x 0.25 mm (film thickness 0.25 m). The GC operating parameters based on temperature programming were as follows oven temperature 40º C, injection port 250º C while the detector temperature was 260º C. Oven temperature programming: 40º C for 2 min, and then raise to 220º C (and held isothermally for 10 min) at 4º C/min. The carrier gas used was H2 at a flow rate of 1 mL/min. The split ratio was 10:1 while 1.0 L of the diluted essential oil in hexane was injected into the GC at inlet pressure was 6.1 kPa. Each analysis was performed in triplicate. Retention indices (RI) value of each component was determined relative to the retention times of a homologous n-alkane series with linear interpolation on the HP-5MS column. The relative amounts of individual components were calculated based on the GC peak area (FID response) without using correction factors. An Agilent Technologies HP 6890N Plus Chromatograph fitted with a fused silica capillary HP-5MS column (30 m x 0.25 mm, film thickness 0.25 m) and interfaced with a mass spectrometer HP 5973 MSD was used for the gas chromatographymass spectrometry (GC/MS) analyses, under the same conditions as those used for GC analysis. The conditions were the same as described above with He (1 mL/min) as carrier gas. The MS conditions were as follows: ionization voltage 70 eV; emission current 40 mA; acquisitions scan mass range of 35350 amu at a sampling rate of 1.0 scan/s. Identification of the constituents The identification of constituents was performed on Hydrodistillation of the essential oils the basis of retention indices (RI) determined by coBriefly, 500 g of each of the pulverized sample were injection with reference to a homologous series of ncarefully introduced into a 5 L flask and distilled alkanes, under identical experimental conditions. water was added until it covers the sample Further identification was performed by comparison completely. Hydrodistillation was carried out in an of their mass spectra with those from NIST (NIST, all glass Clevenger-type distillation unit for 3 h, 2011) and the home-made MS library built up from according to established procedure (Vietnamese pure substances and components of known essential Pharmacopoeia, 1997), at normal pressure. The oils, as well as by comparison of their retention volatile oils distilled over water and were collected indices with literature (Adams, 2007). separately in the receiver arm of the apparatus into a Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/27 Huong et al. Essential oils of Alpinia macruora RESULTS AND DISCUSSION The yield of essential oils were 0.21% (v/w, leaf), 0.15% (v/w, stem), 0.24% (v/w, root), 0.18% (v/w, fruit) and 0.30% (v/w, flower), calculated on a dry weight basis. Oil samples were light yellow (leaf and root), yellow (stem) and colourless (fruit and flower). Table 1 indicates the chemical constituents present in the oils, their percentages as well as retention indices on HP-5MS column. Monoterpenes hydrocarbons (59.9%) and the oxygenated counterparts (27.2%) represent the main classes of compounds present in the leaf oil. Sesquiterpenes are less common (ca. 5.7%). 1,8-Cineole (17.7%), γ-terpinene (13.3%) and β-pinene (11.4%) were the compounds occurring in higher quantity. There are significant amounts of αphellandrene (8.5%), α-pinene (7.8%), α-terpinene (6.4%) and terpinen-4-ol (5.9%). On the other hand, monoterpenes hydrocarbons (71.9%) and oxygenated counterparts (13.6%) were the main classes of compounds identified in the stem, of which the main compounds were γ-terpinene (16.9%), β-pinene (16.4%), 1,8-cineole (11.2%) and α-terpinene (9.4%). α-Pinene (8.4%) and α-phellandrene (5.9%) were also present in sizeable quantity. Table 1 Chemical constituents of A. macruora oilsa Compoundsb α-Thujene α-Pinene Camphene Sabinene β-Pinene β-Myrcene α-Phellandrene -3-Carene α-Terpinene o-Cymene β-Phellandrene 1,8-Cineole (E)-β-Ocimene γ-Terpinene cis-Sabinene hydrate α-Terpinolene Linalool Nonanal Fenchyl alcohol allo-Ocimene Camphor Borneol Terpinen-4-ol α-Terpineol Myrtenal trans-Piperitol Fenchyl acetate 4-Phenyl-2-butanol i Geraniol Bornyl acetate Bicycloelemene Neryl acetate α-Copaene RI c 930 939 953 976 980 990 1006 1011 1017 1024 1028 1034 1052 1061 1073 1090 1100 1106 1120 1128 1145 1167 1177 1189 1207 1209 1222 1241 1253 1289 1327 1362 1377 RId 921 932 946 969 976 988 1004 1008 1014 1022 1032 1044 1054 1065 1089 1095 1100 1118 1128 1141 1167 1177 1187 1195 1207 1229 1243 1249 1287 1337 1359 1374 MI e f g f g g g g f g f f g f f f f f f f f f f f f f f f f f g f f f L 1.6 7.8 1.2 11.4 1.3 8.5 6.4 4.5 17.7 0.6 13.3 0.1 3.3 1.6 0.1 0.1 0.5 5.9 0.7 0.2 0.1 2.2 0.2 0.1 S 2.0 8.4 2.1 16.4 1.6 5.9 9.4 3.8 11.2 1.0 16.9 4.4 0.3 0.1 1.1 0.1 0.3 0.3 0.2 R 1.9 6.5 2.9 12.5 1.4 1.9 0.2 8.5 2.1 8.7 0.7 13.9 3.7 0.4 0.1 0.1 0.2 0.5 2.3 0.2 0.1 7.8 0.4 1.0 0.5 0.7 Fr 0.4 5.8 1.3 11.1 1.3 3.7 3.2 1.2 11.1 0.6 5.9 1.4 0.3 0.1 0.1 0.6 0.3 0.3 0.3 5.0 0.1 0.2 Fl 0.6 4.5 0.8 9.0 8.8 1.1 1.5 4.7 0.6 3.4 5.5 0.6 7.9 1.3 0.5 0.3 4.4 1.5 3.5 7.2 1.5 0.5 Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/28 Huong et al. Essential oils of Alpinia macruora Geranyl acetate β-Elemene α-Gurjunene β-Caryophyllene Widdrene γ-Elemene α-Guaiene Aromadendrene α-Humulene Selina-4(15),7(11)-diene γ-Gurjunene γ-Muurolene Germacrene D α-Amorphene β-Selinene -Selinene Bicyclogermacrene α-Muurolene β-Bisabolene (E,E)-α-Farnesene δ-Cadinene (E)-Nerolidol Spathulenol Caryophyllene oxide -Muurolol α-Cadinol (E,E)-Farnesol Phytol 1381 1391 1412 1419 1431 1437 1440 1441 1454 1475 1477 1480 1485 1485 1486 1493 1500 1500 1506 1508 1525 1563 1578 1583 1646 1654 1718 2125 1379 1389 1409 1417 1432 1434 1437 1439 1452 1470 1475 1478 1484 1485 1488 1498 1500 1500 1505 1507 1522 1561 1577 1581 1640 1652 1722 2119 0.1 1.7 1.3 0.8 3.4 0.7 1.1 1.0 1.5 1.2 1.4 2.4 2.3 18.6 12.6 0.7 0.1 0.4 0.3 3.6 0.4 1.8 0.2 0.1 0.3 0.6 0.2 0.5 0.8 3.1 1.0 0.4 0.1 1.0 0.2 0.2 0.6 0.5 3.3 0.2 0.2 0.4 0.6 1.1 0.3 0.7 0.9 0.7 0.9 0.1 0.1 0.1 0.2 0.4 0.7 0.5 0.2 0.3 0.8 0.3 0.3 0.7 0.3 0.4 0.6 7.1 0.7 1.0 0.2 0.8 0.4 0.5 0.4 0.2 0.1 Total 95.2 93.6 92.0 93.5 97.7 Monoterpene hydrocarbons 59.9 71.9 56.3 35.9 44.8 Oxygenated monoterpenes 27.2 13.6 21.7 18.0 22.9 Sesquiterpene hydrocarbons 5.4 7.2 10.7 30.5 28.2 Oxygenated monoterpenes 0.5 0.9 3.1 8.7 1.8 Diterpenes 0.2 0.1 Non-terpenes 2.2 0.3 a b SD, values were insignificant and excluded from the Table to avoid congestion; Elution order from HP5MS column; c Retention indices on HP-5MS column; d Literature retention indices; e Mode of Identification; f Identification by mass spectra and GC retention indices; g Identification by mass spectra, column retention indices and co-injection with authentic compound; i tentative identification; - Not found; L leaf; S stem; r root; Fr fruit; Fl flower The main classes of compounds in the root oil were monoterpenes hydrocarbons (56.3%), oxygenated monoterpenes (21.7%) and sesquiterpene hydrocarbons (10.7%). Moreover, the main constituents of the oil were γ-terpinene (13.9%), βpinene (12.5%), 1,8-cineole (8.7%), α-terpinene (8.5%), fenchyl acetate (7.8%) and α-pinene (6.5%). The authors have identified a large proportion of f f f g f f f f f g f f f f f f g f f g f f f g f f f g monoterpene hydrocarbons (35.9%), sesquiterpene hydrocarbons (30.5%) and oxygenated monoterpenes (18.0%) in the fruit. The oil was rich in βcaryophyllene (18.1%), β-pinene (11.1%) and 1,8cineole (11.1%). In addition, caryophyllene oxide (7.1%), γ-terpinene (5.9%), α-pinene (5.8%) and bornyl acetate (5.0%) were also present in significant quantity. Moreover, monoterpene hydrocarbons Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/29 Huong et al. Essential oils of Alpinia macruora agarofuran, (E,E)-farnesol, β-cubebene, δ-cadinene, (44.8%), oxygen containing monoterpenes (22.9%) β-bisabolene, α-humulene and caryophyllene oxide and sesquiterpene hydrocarbons (18.2%) were were either absent or present in lower amounts in A. prominent in the flower oil. The quantitatively macruora. significant constituents of the oil were βThe chemical constituents of essential oils of caryophyllene (12.6%), sabinene (9.0%), β-pinene Alpinia plants from some other parts of the world (8.8%), γ-terpinene (7.9%) and bornyl acetate (7.2%). have been documented. The major constituents of A. The authors are unaware of any previous calcarata from India were 1,8-cineole (35.9%) and βstudy on the essential oils of A. macruora. The fenchyl acetate (12.9%), while α-terpineol (15.1%), present report may represent the first of its kind. α-fenchyl acetate (12.5%), (E)-nerolidol (10.1%) and However, relative information is available on the caryophyllene oxide (10.1%) were the main compositions of volatiles from some other Alpinia compounds of A. smithiae (Raji et al., 2013). 1,8species growing in Vietnam. For example, the fruit Cineole (17.4%) and humulene epoxide II (14.1%) oil of A. menghaiensis (Dai et al., 2016) comprised are the main components of A. allughas from India mainly of monoterpenes represented by β-pinene which displayed antioxidant and antifungal activities (40.4%) and α-pinene (11.3%). The leaf oil of A. (Sethi et al., 2015). An analysis from Malaysia polyantha has its major compounds as camphor reported the abundance of β-sesquiphellandrene (16.1%), α-pinene (15.2%) and β-agarofuran (36.5%) and (E)-methyl cinnamate (78.2%) in the (12.9%), while α-pinene (12.4%), β-cubebene rhizomes of A. aquatica and A. malaccensis (10.6%) and β-agarofuran (10.3%) were present in respectively (Sirat et al., 1995). The leaf oil of A. the stem (Huong et al., 2015a). However, while βpurpurata (Victório et al., 2010) from Brazil was rich cubebene (12.6%) and fenchyl acetate (10.8%) were in β-pinene (34.7%) and α-pinene (11.8%). Another identified in the root, the fruit was rich in δ-cadinene report identified trans-caryophyllene (32.61%) in the (10.9%), β-caryophyllene (9.1%) and β-pinene leaf; 1,8-cineole (32.25%) and myrcene (13.63%) (8.7%). 1,8-Cineole was the most significant from the pseudostem; tetracosane (42.61%) in the compound of rhizomes of A. henryi (Giang et al., rhizome and tetracosane (13.39%) from the fruit of A. 2007) and A. laosensis (Dung et al., 2000). rafflesiana grown in Malaysia (Jusoh et al., 2013). Sesquiterpenes were the dominant compounds in the The major components of A. galanga (Suresh et al., essential oils of A. chinensis. These include β2016) were 1,8-cineole (32.9%) and α-terpineol bisabolene (47.9%) in the leaf (Dung et al., 1994a), (12.7%). The Korean specie of A. kwangsiensis (Wu caryophyllene oxide (13.2%) and β-bisabolene et al., 2015) rhizome afforded oil whose main (10.4%) in the root (Leclerq et al., 1994) as well as compounds were camphor (17.59%), eucalyptol (E,E)-α-farnesene (26.5%), α-humulene (22.3%), β(15.16%), β-pinene (11.15%) and α-pinene (10.50%). bisabolene (17.1%) and β-caryophyllene (13.1%) in The major components of rhizome oil of A. the flower (Dung et al., 1994b). The composition of conchigera from Malaysia (Sirat et al., 1995) include the flowers of A. speciosa (Dung et al., 1994c) β-sesquiphellandrene (20.5%), β-bisabolene (12.1%) consisted mainly of terpene hydrocarbons β-pinene and 1,8-cineole (11.6%). The rhizome of A. speciosa (34.0%), -pinene (14.8%) and β-caryophyllene collected from India (Akshaya et al., 2010) contained (10.8%). A previous study reported abundance of αterpinen-4-ol (15.4%) and 1,8-cineole (11.1%). The pinene and β-pinene in the leaf oils of A. malaccensis main constituents of essential oils of A. nutans were (Huong et al., 2015b). In another study, while (E,E)sabinene (27.8%), 1,8-cineole (17.4%) and terpinenfarnesol make up the oil of the seed of A. 4-ol (14.9%) in the aerial parts while terpinen-4-ol breviligulata (Dung, et al., 1994d), α-pinene and β(25.1%), γ-terpinene (19.4%), sabinene (14.2%) and pinene occurred in the leaf oil (Dung et al., 1994f). 1,8-cineole (10.8%) were present in the flower (Joshi The seed oil of A. katsumadai was dominated by et al., 2010). myrcene, linalool and citronellol (Dung et al., 1990). Both inter-species and intra-species variation Although ubiquitous terpenes predominate in the could be observed in the essential oils of Alpinia essential oils of other Alpinia plants and A. macruora plants. For example, valencene (19.04%), from Vietnam (Dung et al., 1993; Dung et al., calamenene (10.11%) and nootkatone (8.97%) were 1994e), some variation could be seen among the the main components of A. oxyphylla from China components of essential oils. The main compounds of (Wang et al., 2014). In another report, myrtenal other Alpinia essential oils from Vietnam such as (10.25%) and α-citral (9.85%) occurred as the major myrcene, citronellol fenchyl acetate, β-cubebene, βBoletin Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/30 Huong et al. Essential oils of Alpinia macruora component in leaf oil of A. oxyphylla from another part of China (Feng et al., 2012). Terpinen-7-al (40.5%) and sabinene hydrate (15.4%) were identified in A. zerumbet from Brazil (Victório et al., 2010), while, 4-terpineol (32.9%), 1,8-cineole (21.4%) and γ-terpinolene (10.0%) were the monoterpenes of A. zerumbet from another region of Brazil (Mendes et al., 2015). In addition, the major components in the oil of A. calcarata from India (Suresh et al., 2016) were α-fenchyl acetate (12.9%), cubenol (15.0 %) and 1,8-cineole (12.1 %) while another sample from India contained 1,8-cineole (35.9%) and β-fenchyl acetate (12.9%). Also, 1,8Cineole (25.4%), β-pinene (15.1%) and camphor (15.3%) were identified in the leaf of A. nigra (Kanjilal et al., 2010), while the rhizome comprised of 1,8-cineole (34%) and α-fenchyl acetate (13.1%). Moreover, fresh leaf of A. nigra from Bangladesh (Islam et al., 2014) gave oil containing large amount of 1,5,9,9-tetramethyl-1,4,7-cycloundecatriene (24.92%), β-pinene (12.90%), 5-amino-6-(2 fluoroanilino)furazano[3,4-b] pyrazine (12.18%) and isocaryophyllene (10.76%). It could be seen that the essential oils of Alpinia plants from all over the world exhibited chemical variability. In addition, the combination of the observed major compounds of the leaf, stem and root of A. macruora (γ-terpinene/β-pinene/1,8cineole, β-caryophyllene/β-pinene/1,8-cineole in the fruit, as well as β-caryophyllene/sabinene in the flower, were not reported previously for any of the studied Alpinia essential oils from Vietnam and other parts of the world. It was well known that each plant parts contained different phytochemical composition. The variation between these results and those from other parts of the world may be due to the ecological and climatic differences between these regions; as well as the age of the plants and chemotype. The observed compositional patterns may have contributed to the biological activities of Alpinia essential oils such as antimicrobial (Joshi et al., 2010; Jusoh et al., 2013), antifungal (Sethi et al., 2015), insecticidal (Wu et al., 2015), modulation of the activity of aminoglycoside antibiotics (Mendes et al., 2015), cytotoxic (Wang et al., 2014), antioxidant (Joshi et al., 2010; Wang et al., 2014; Sethi et al., 2015) and enhances skin permeation (Feng et al., 2012). CONCLUSION The compositions of the leaf, stem, root, fruit and flower oils of A. macruora from Vietnam were reported. The essential oils were characterized by high contents of γ-terpinene/β-pinene/1,8-cineole in the leaf, stem and root, β-caryophyllene/β-pinene/1,8cineole in the fruit and β-caryophyllene/sabinene in the flower. In addition, a comparative analysis of the chemical compositions of the studied oil samples with data on essential oils of other Alpinia plants from Vitenam and other parts of the world revealed a high chemical variation. ACKNOWLEDGMENTS The authors wish to thank National Foundation for Science and Technology Development, Vietnam (NAFOSTED) for financial support of this study through the Project Nr. 106-NN.03-2014.23. We also appreciated the effort of Dr. Elena Falqué López, Química Analítica, Facultad de Ciencias, España, for the translation of the abstract of the manuscript into the Spanish language. REFERENCES Adams RP. 2007. Identification of essential oil components by gas chromatography/mass spectrometry. 4th Edition, Allured Publishing, Carol Stream, Illinois, USA. Akshaya KI, Pradeep KT, Agrawal NK. 2010. Chemical composition and antimicrobial activity of the essential oil of Alpinia speciosa K. Schum. rhizome from India. J Essent Oil Res 22: 179 - 182. Bình NQ. 2011. Study of the classification of the ginger family (Zingiberaceae Lindl.) in Vietnam. PhD dissertation, Institute of Ecology and Biological Resources, Hanoi, Vietnam. Chau LTM, Thang TD, Tu NTM, Dai DN, Ogunwande IA. 2015. Constituents of essential oils from the leaves, stems and roots of Zingiber gramineum and Zingiber rufopilosum. Bol Latinoam Caribe Plant Med Aromat 14: 449 - 455. Dai DN, Huong LT, Thang TD, Olayiwola TO, Ogunmoye AO, Ogunwande IA. 2016. Essential oils of the fruit of Alpinia menghaiensis. British Biotech J 11: 1 - 7. Dung NX, Phuöng DL, Leclerq PA. 1990. Constituents of the stem, leaf and seed oils of Alpinia katsumadai Hayata L. from Vietnam. Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/31 Huong et al. Essential oils of Alpinia macruora J Essent Oil Res 2: 259 - 261. Dung NX, Trinh DC, Dô DR, Leclercq PA. 1993.The essential oil composition of Vietnamese Alpinia breviligulata Gagnep. flowers. J Essent Oil Res 5: 575 - 576. Dung NX, Trinh DC, Dô DR, Leclercq PA. 1994a. Chemical composition of the leaf oil of Alpinia chinensis Rosc, from Vietnam. J Essent Oil Res 6: 91 - 92. Dung NX, Trinh DC, Dô DR, Leclercq PA. 1994b. Chemical composition of the flower oil of Alpinia chinensis Rosc, from Vietnam. J Essent Oil Res 6: 637 - 638. Dung NX, Trinh DC, Dô DR, Leclercq PA. 1994c. Constituents of the flower oil of Alpinia speciosa K. Schum. from Vietnam. J Essent Oil Res 6: 433 - 434. Dung NX, Trinh DC, Dô DR, Leclercq PA. 1994d. Constituents of the seed and fruit peel oils of Alpinia breviligulata Gagnep. from Vietnam. J Essent Oil Res 6: 295 - 297. Dung NX, Trinh DC, Dô DR, Leclercq PA. 1994e. Constituents of the rhizome and root oils of Alpinia breviligulata Gagnep. from Vietnam. J Essent Oil Res 6: 499 - 501. Dung NX, Trinh DC, Dô DR, Leclercq PA. 1994f. Chemical composition of the leaf oil of Alpiniabreviligulata Gagnep. from Vietnam. J Essent Oil Res 6: 181-182. Dung NX, Trung HO, Vän NH, Nguyên XP, Leclercq PA. 2000. Volatile constituents of the rhizome oil of Alpinia laosensis Gagnep. from Indochina. J Essent Oil Res 12: 213 215. Feng H, Luo JY, Kong WJ, Dou XW, Wang Y, Zhao XS, Zhang WP, Qiong L, Yang M. 2012. Enhancement effect of essential oils from the fruits and leaves of Alpinia oxyphylla on skin permeation and deposition of indomethacin. The Royal Soc Chem 1: 1 15. Giang MP, Son TP, König WA. 2007. Chemical Composition of the essential oil from the rhizomes of Alpinia henryi K. Schum. of Vietnam. J Essent Oil Res 19: 507 - 508. Hương LT, 2016. Study on biological characteristics, chemical composition of essential oils of the species of genus Alpinia Roxb. and Amomum Roxb. (Zingiberaceae) in North Center of Vietnam. PhD. Dissertation, Institute of Ecology and Biological Resources, Vietnam Acadamy of Science and Technology. Huong LT, Thang TD, Ogunwande IA. 2015a. Chemical constituents of essential oils from the leaves, stems, roots and fruits of Vietnamese species of Alpinia polyantha. Nat Prod Comm 10: 367 - 368. Huong LT, Thang TD, Ogunwande IA. 2015b. Volatile constituents of essential oils from the leaves, stems, roots and fruits of Vietnamese species of Alpinia malaccencis. Eur J Med Plant 7: 118 - 124. Islam F, Islam S, Shahjahan M, Nandi NC, Satter MA. 2014. Chemical constituents of essential oil from the leaf of Alpinia nigra of Bangladesh. Int Food Res J 21: 161 - 164. Joshi S, Prakash O, Anil KP, Mathela CS. 2010. Chemical composition, and antioxidant and antimicrobial activities of Alpinia nutans Rosc. J Essent Oil Res 22: 85 - 90. Jusoh S, Sirat HM, Ahmad F. 2013. Essential oils of Alpinia rafflesiana and their antimicrobial activities. Nat Prod Commun 8: 1317 1320. Kanjilal PB, Rumi K, Couladis M. 2010. Essential oil composition of leaf and rhizome oil of Alpinia nigra (Gaertner) B. L. Burtt. from Northeast India. J Essent Oil Res 22: 358 360. Kress WJ, Prince LM, Willia KJ. 2005. The molecular phylogeny of Alpinia (Zingiberaceae): a complex and polyphyletic genus of gingers. Amer J Bot 92: 167 - 178. Leclercq PA, Dung NX, Trinh DC, Dô DR. 1994. Composition of the root oil of Alpinia chinensis Rosc. from Vietnam. J Essent Oil Res 6: 401 - 402. Mendes FRS, Silva FGE, Sousa EO, Rodrigues FFG, Costa JGM, Monte FJQ, Lemos TLG, Assunção JCC. 2015. Essential oil of Alpinia zerumbet (Pers.) B.L. Burtt. & R.M. Sm. (Zingiberaceae): chemical composition and modulation of the activity of aminoglycoside antibiotics. J Essent Oil Res 27: 259 - 263. NIST. 2011. Chemistry Web Book. Data from NIST Standard Reference Database 69. Raji G, Pradeep DP, Yusufali C, Sabulal B. 2013. Chemical profiles of volatiles in four Alpinia species from Kerala, South India. J Essent Oil Res 25: 97 - 102. Sethi S, Prakash O, Pant AK. 2015. Essential oil Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/32 Huong et al. Essential oils of Alpinia macruora composition, antioxidant assay and antifungal activity of essential oil and various extracts of Alpinia allughas (Retz.) Roscoe leaves. Cogent Chem 1: 121 - 127 Sirat HM, Nordin BA. 1995. Chemical composition of the rhizome oil of Alpinia conchigera Griff from Malaysia. J Essent Oil Res 7: 195 - 197. Suresh VN, Menon AN, Esakkidurai T, Pitchumani K. 2016. Essential oil composition of Alpinia calcarata and Alpinia galanga rhizomes-a comparative study. J Essent Oil-Bearing Pl 19: 82 - 87. Victório CP, Leitão SG, Lage CLS. 2010. Chemical composition of the leaf oils of Alpinia zerumbet (Pers.) Burtt et Smith and A. purpurata (Vieill) K. Schum. from Rio de Janeiro, Brazil. J Essent Oil Res 22: 52 - 54. Vietnamese Pharmacopoeia. 1997. Medical Publishing House, Hanoi, Vietnam. Wang CZ, Yuan HH, Bao X, Minbo L. 2014. Chemical composition, in vitro cytotoxic and antioxidant activities of the fruit essential oil of Alpinia oxyphylla. Asian J Chem 26: 4201 - 4205. Wu Y, Zhang WJ, Huang DY, Ying W, Wei JY, Li ZH, Sun JS, Bai JF, Tian ZF, Wang PJ, Du SS. 2015. Chemical compositions and insecticidal activities of Alpinia kwangsiensis essential oil against Lasioderma serricorne. Molecules 20: 21939 - 21945. Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/33