Chemical Constituents of the Leaves of Eberhardtia Aurata (Sapotaceae)V. T. Nguyen, V. C. Pham, T. M. H. Doan, B. N. Truong, T. H. Tran, M. Litaudon and V. M. Chau ABSTRACT
In the framework of scientific co-operation between the Institute of Marine Biochemistry, (Vietnam Academy of Science and Technology) and the Institute of Natural Product Chemistry (Natural Product Chemistry, France) on phytochemistry of the Vietnamese flora, the plant Eberhardtia aurata (Pierre ex Dubard) Lecomte was selected for its cytotoxic activity on KB cell lines [14.6% inhibition at 1 μg/ml for the ethyl acetate (EtOAc) extract of the leaves]. From the EtOAc extract of the leaves of this plant, 4 oleanane triterpenes, taraxerol (1), taraxerone (2), taraxeryl acetate (3), 3 β-octacosanoyloxy-12-oleanen-28-ol (4) and 1 sterol, spinasterol (5) were isolated. Their structures were elucidated by using MS and NMR spectroscopic methods, including 2D NMR spectroscopy (COSY, HMQC, HMBC).
Key words: Eberhardtia aurata; Sapotaceae; triterpenes; ethyl acetate; cytotoxic activity
REFERENCESVO, V.C. (1997) Vietnamese Medicinal Plants Dictionary, NXB khoa học và Kỹ thuật, vol. 1, pp. 1035–1036.Doan, T.M.H., Pham, V.C., Litaudon, M. and Nguyen, V.H. (2009) Oleanan and ursan Triterpens from the stem bark of Eberhardtia aurata (Sapotaceae), Journal of Science and Technology (Vietnamese), 47(1),95–99.Doan, T.M.H., Pham, V.C., Litaudon, M. and Nguyen, V.H.(2009) Chemicalconstituents of the stem bark of Eberhardtia aurata (Sapotaceae), Journal of Science and Technology (Vietnamese), 47(6), 35–39.Mosmann, T. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, Journal of Immunological Methods, 65, 55–63.Phan, V.K., Phan, T.S., Cha, V.M., Kim, Y.H., Phan, M.G. and Phạm, H.D. (2003) Study on chemical constituent of Acanthopanax trifoliatus (L.) Merr., Araliaceae), Journal of Chemistry (Vietnamese), 41(4), 39–44.Fakir, S.T., Md. Hossain, S., Chowhdury, A.M.S.U., Farhana, A., Al-Mansur, M. and Choudhury, M. (2009) HasanDhaka Universityphytochemical studies on the leaves of Xylia dolabriformis, J. Pharm. Sci., 8(2), 171–172.Hernández-Chávez, I., Torres-Tapia, L.W., Simá-Polanco, P., Cedillo-Rivera, R., Moo-Puc, R. and Peraza-Sánchez, S.R. (2012)Antigiardial activity of Cupania dentata bark and its constituents, J. Mex. Chem. Soc., 56(2), 105–108.Trinh, T.T., Tran, V.S., Frank, K. and Wessjohann, L. (2008) Triterpens from the roots of Codonopsis pilosula, Journal of Chemistry, 46(4), 515–520.Chatterji, N., Rastogi, R.P. and Dhar, M.L. (1965) Chemical examination of Bacopa monniera. II. The constitution of bacoside A, Indian Journal of Chemistry, 3(1), 24–29.Wandji, J., Tillequin, F., Mulholland, D.A., Wansi, J.D. , Fomum, T.Z., Fuendjiep, V. and Libot, F., and Tsabang, N. (2002) Fatty acid esters of triterpenoids and steroid glycosides from Gambeya africana, Planta Med., 68(9), 822–826.Ragasa, C.Y., Espineli, D.L., Mandia, E.H., Don, M-J. and Shen, C.C. (2012) A new triterpene from Glinus oppositifolius, Chinese Journal of Natural Medicines, 10(4), 0284−0286.Ragasa, C.Y. and Lim, K. (2005) Sterols from Cucurbita maxima[J], Philipp. J. Sc., 134(2), 83–87.Barton, D.H.R. and Cox, J.D. (1948) Application of the method of molecular rotation differences to steroid. V. Olefinic unsaturation at the 7,8-position, Journal of the Chemical Society, 67, 1354–1357.Villaseñor, I.M. and Domingo, A.P. (2000) Anticarcinogenicity potential of spinasterol isolated from squash ﬂowers, Teratog Carcinog Mutagen, 20, 99–105.Zhou, C.C., Sun, X.B., Liu, J.Y., Luo, S.Q. and Lu, C.Y. (1985) Anti-inﬂammatory effect of alpha-spinasterol, Yao Xue Xue Bao, 20, 257–261.