Journal of Essential Oil Bearing Plants ISSN Print: 0972-060X Online: 0976-5026 www.jeobp.com Jeobp 15 (6) 2012 pp 1044-1048 1044 Chemical Composition of the Leaf Essential Oil of Desmos chinensis Lour. (Annonaceae) from Vietnam Ðo Ngoc Ðài 1,2 *, Tran Ðình Thang 3, 1 Institute Ecology and Biological Resources, Academy of Science and Technology, Ha Noi, Vietnam 2 Faculty of Biology, Vinh University, 182- Le Duan, Vinh, Vietnam 3 Faculty of Chemistry, Vinh University, 182- Le Duan, Vinh, Vietnam Received 27 March 2011; accepted in revised form 12 November 2011 Abstract: The leaf oil of Desmos chinensis Lour., collected from Hatinh province (Vietnam) in October 2007, was isolated by steam distillation to give oil yield 0.15 % and analyzed by Capillary GC and GC-MS. Fifty seven components have been identified accounting more than 94.9 % of the oil. The major constituents of this oil appeared to be limonene (11.8 %), germacrene D (11.5 %), α-pinene (11.3 %), benzyl benzoate (9.8 %), β-caryophyllene (9.4 %) and β-pinene (6.2 %). Key words: Annonaceae, Desmos, Desmos chinensis Lour, limonene, germacrene D. Introduction Annonaceae 129 genera and over 2200 species: tropics and subtropics, especially in Old World; 22 genera and 114 species in China. Genus Desmos about 59 species; S. and S.E. Asia, Australia, Oceania; five species and three subspecies in Vietnam 1. Desmos chinensis Lour. (Annonaceae) is distributed widely in Northern Vietnam and is used as an antimalarial, insecticidal, antirheumatic, antispasmodic, and analgesic in folk medicine 2,3. The previously phytochemical studies of D. chinensis have reported several chalcones and flavonoids such as desmethoxymateucinol, negletein and lawinal and new dihydroflavone named cochinine A 4,5,6, C- benzylated chalcones 7, oxoaporphine alkaloids 8, and essential oils 9,10. However, only a few biological effects have been reported, e.q., antibacterial activity for the mixture of 2,4- dihydroxy-6-methoxychalcone and chrysin 11, anti-hiv activity for 2-methoxy-3-methyl-4,6- dihydroxy-5-(3-hydroxy) cinnamoyl benzaldehyde and lawinal against HIV-1 replication in H9 lymphocytes 12, and tyrosine kinase inhibitory effect for desmal in situ in epidermal growth factor receptor-overexpressing NIH3T3 cells 13. The chemical constituent of the essential oil from Desmos cochinchinensis Lour. flower, collected in Nghean province, has been investigated by GC-MS method. The essential oil obtained from young flower contains mainly trans-caryophyllene (yield 56.22 % w/w), whereas from ripened one - mainly spathulenol (yield 61.57 % w/w) 14. Chemical constituents of the root of Desmos *Corresponding author (Ðo Ngoc Ðài) E-mail: < daidn23@gmail.com > 2012, Har Krishan Bhalla & Sons
Ðo Ngoc Ðài et al. / Jeobp 15 (6) 2012 1044-1048 1045 chinensis Lour. (Annonaceae) were studied in an attempt to discover some antitumor compounds. As a result, seven compounds have been isolated from the CHCl 3 extract. They were identified as unonal (I), negletein (II),desmethoxymatteucinol (III), desmethoxymatteucinol-7-methylether (IV), benzoic acid (V), β-sitosterol (VI) and stigmasterol (VII). Compounds I, IV, V, VI and VII were found from this plant for the first time. All flavonoids isolated from this species showed a common feature with the absence of B-ring substitution, which may be of value in chemotaxonomy 15. The leaf oil of of Desmos cochinchinensis var. fulvescens Ban collected from Hatinh province, Vietnam, in October 2006 was isolated by steam distillation to give oil yield 0.15 % and analyzed by Capillary GC and GC-MS. The major constituents of this oil appeared to be β-elemene (16.1 %), d-cadinene (13.8 %) and β-caryophyllene (13.7 %) 16. Experimental Source Desmos chinensis Lour. (Annonaceae), is a clember to 7-10 m long, growing in Vietnam. Leaves were collected from Vu Quang National Park, Hatinh province in October 2007. A voucher specimen (DD2) is deposited at the Herbarium of the Vinh University. Fresh leaves were shredded and their oil was obtained by steam distillation for 3 h at normal pressure, according to the Vietnamese Pharmacopoeia 17. About 15 mg of oil, which was dried with anhydrous sodium sulfate, was dissolved in 1ml of CH 3 OH (for spectroscopy or for chromatography). GC Analysis was performed on a HP 6890 Plus Gas chromatograph equipped with a FID and fitted with HP-5MS column (L=30 m, ID = 0.25 mm, film thickness = 0.25 μm). The analytical conditions were: carrier gas H 2, injector temperature (PTV) 250 C, detector temperature 260 o C, temperature programmed 60 C (2 min hold) to 220 C (10 min hold) at 4 C/min. GC-MS A Hewlett Packard 6890 Plus Chromatograph was fitted with a fused silica capillary column HP- 5MS column (L = 30 m, ID = 0.25 mm, film thickness = 0.25 μm). The condition of use were the same as described above with He as carrier gas, and interface with a mass spectrometer HP 5972 MSD (70eV). The temperature was programmed as reported above. Components identification was carried out by comparing MS data with those reported in Library Willey on Chemstation HP, and in some cases substances identified from oils known composition and also with standard substances 18-20. Results and discussion The yield of the fresh leaf oil is 0.15 %. Of the leaf oil components of Desmos chinensis Lour. from Vietnam that were separated by GC, fifty seven compounds were identified after GC-MS analysis, representing 94.9 % of the total oil (Table 1). It can be seen that there were a large number of compounds, the majority of which were sesquiterpenes, but major compounds were limonene (11.8 %), germacrene D (11.5 %), α- pinene (11.3 %), benzyl benzoate (9.8 %), β- caryophyllene (9.4 %), β-pinene (6.2 %). Less predominant constituents germacrene B (3.5 %), α-humulene (3.4 %), δ-cadinene (3.0 %), bicycloelemene (2.4 %), β-cubebene (2.1 %), β- myrcene (1.9 %), α-copaene (1.9 %), caryophyllene oxid (1.9 %), β-elemene (1.5 %), α- bergamotene (1.3 %), α-amorphene (1.1 %). All the other components were in concentration of less than 0.1. Acknowledgments The authors wish to thank the NAFOSTED (Vietnam) for the financial support of this study through the Project Nr. 104.01-2010.27.
Ðo Ngoc Ðài et al. / Jeobp 15 (6) 2012 1044-1048 1046 Table 1. Chemical composition of the essential oil of Desmos chinensis Lour. from Vietnam S.No Compound RI %FID 1 Anisole 918 0.4 2 α-pinene 939 11.3 3 Camphene 953 0.1 4 Sabinene 976 0.6 5 β-pinene 980 6.2 6 β-myrcene 990 1.9 7 α-terpinene 1016 tr 8 Limonene 1032 11.8 9 (E)-β-Ocimene 1052 0.7 10 γ-terpinene 1061 0.1 11 α-terpinolene 1090 0.1 12 Linalool 1100 0.6 13 Nonanal 1106 0.1 14 Geijerene 1143 0.1 15 Menthone 1172 0.5 16 Terpinen-4-ol 1177 tr 17 iso-menthone 1183 0.1 18 2-Decenal 1259 tr 19 Benzoic acid 1310 0.1 20 Bicycloelemene 1327 2.4 21 α-cubebene 1351 0.6 22 Neryl axetate 1362 0.1 23 α-ylangene 1375 0.1 24 α-copaene 1376 1.9 25 β-bourbolene 1388 0.5 26 β-cubebene 1388 2.1 27 β-elemene 1389 1.5 28 α-gurjunene 1412 tr 29 α-cederene 1412 0.5 30 α-bergamotene (bicyclo 3.1.1] hept-2-ene 1413 1.3 31 β-caryophyllene 1419 9.4 32 β-cedrene 1421 0.5 33 β-gurjunene 1434 0.1 34 α-guaiene 1440 0.3 35 Aromadendrene 1441 0.2 36 β-farnesene 1443 0.1 37 α-humulene 1454 3.4 38 δ-cadinene 1459 3.0 39 α-amorphene 1485 1.1 40 Germacrene D 1486 11.5 41 β-selinene 1490 0.2 42 α-farnesene 1506 tr 43 endo-1-bourbonanol 1520 0.4 44 Cadina-1,4-diene 1532 0.7
table 1. (continued). Ðo Ngoc Ðài et al. / Jeobp 15 (6) 2012 1044-1048 1047 S.No Compound RI %FID 45 α-cadinene 1539 0.1 46 γ-cadinene 1541 0.3 47 α-calacorene 1546 0.1 48 Germacrene B 1561 3.5 49 (E)-Nerolidol 1563 0.3 50 Salvial-4(14)-en-1-one 1582 0.3 51 Caryophyllene oxid 1583 1.9 52 cis-asarone 1617 tr 53 t-muurolol 1641 0.9 54 α-cadinol 1654 0.8 55 trans-asarone 1676 0.3 56 Farnesyl acetate 1726 tr 57 Benzyl benzoate 1763 9.8 Total 94.9 References 1. Nguyen Tien Ban (2000). Flora of Vietnam, Vol 1, Science and Technology publitsing House, Hanoi. 2. Chi, V.V. (ed.) (1997). Vietnamese Medical Plant Dictionary. Ha Noi Medicine Publication. 3. Loi, D.T., (2001). Glossary of Vietnamese Medical Plants. Hanoi S & T Publication 4. Hao, X.Y., Shang, L., Hao, X.J. (1993). Flavonoids from Desmos chinensis. Yunnan Zhiwu Yanjiu, 15: 295-298. 5. Ju, J. and Tu, J. (1999). Studies on chemical constituents of seeds of Desmos chinensis Lour. Zhongguo Zhongyao Zazhi, 24: 418-421. 6. Zhao, J. (1992). Chemical constituents on the roots of Desmos chinensis. Yunnan Zhiwu Yanji, 14: 97-100. 7. Rahman, M.M., Qais, N., and Rashid M.A. (2003). A new C-benzylated chalcone from Desmos chinensis. Fitoterapia, 74: 511-514. 8. Liu, X.T., Zhang Q., Liang, J.Y., Ming, Z.D. (2004). A new oxoaporphine from Desmos chinensis Lour., Chinese Journal of Natural Medicines, 2: 205-207. 9. Tran, H.T., Tran, M.H., Ninh, K.B., Nguyen, Q.H., Vu, T.M., Bighelli, A., Castola, V., Casanova, J. (2003). Chemical composition of the flower essential oil of Desmos chinensis Lour. from Vietnam, J. Pharmaceutical, 1: 23-24. 10. Brophy, J.J., Goldsack, R.J. and Forster, P.I. (2002). The leaf oils of the Australian species of Desmos (Annonaceae). J. Essent. Oil Res., 14: 298-301. 11. Qais, N., Rahman, M.M., Jabbar, A., and Rashi, M.A. (1996). 5-Methoxy-7-hydroxyflavanone from Desmos chinensis. Fitoterapia, 67: 476. 12. Wu, J.H., Wang, X.H., Yi, Y.H., and Lee, K.H. (2003). Anti-AIDS agents. 54. A potent anti- HIV chalcone and flavonoids from genus Desmos. Bioorg. & Med. Chem. Lett., 13: 1813-1815. 13. Kakeya, H., Imoto, M., Tabata, Y., Iwami, J., Matsumoto, H., Nakamura, K., Koyano, T., Tadano, K., and Umezawa, K. (1993). Isolation of a novel substrate-competitive tyrosine kinase inhibitor, desmal, from the plant Desmos chinensis. FEBS, 320: 169-172. 14. Rang, D.D., Tuong, D.T., Linh, D.K. (2004). Preliminary study on the chemical constituent of Desmo cochinchinensis Lour. in Nghe An province, J. Application and Chemistry, 10: 23-26.
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