83(P-83) フタバガキ科植物のスチルベンオリゴマーの構造と生物活性(ポスター発表の部)

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A number of novel resveratrol oligomers have been recently discovered from the plants belonging to the family Dipterocarpaceae, Vitaceae, Cyperaceae and Leguminosae and their various bioactivities such as chemopreventive and hepatoprotective have been reported. Previously, we reported the structural elucidation of stilbenoids with inhibitory effect on DNA topoisomerase II. In the course of our investigation of chemical constituents with biological activity, phytochemical study on Dipterocarpaceous plants has been carried out. Examination of chemical constituents in the stem bark of Vatica rassak, Shorea hemsleyana and Hopea parvlflora resulted in isolation of 33 resveratrol derivatives including 23 new compounds. The structural elucidation of the isolates was accomplished by spectroscopic analysis. Among them, vaticanol D (13), isolated from V. rassak, was determined to be a novel resveratrol hexamer. Occurrence of stilbene derivatives with C-glycosyl moiety (26-30) or having an unsaturated five-membered lactone ring moiety (24) was revealed in S. hemsleyana. Structure of Vaticanol D (13) The molecular formula of 13 was determined by FABMS. The ^1H, ^<13>C NMR, 2D HOHAHA and HMQC spectra of 13 suggested the presence of six resveratrol units as partial structure (resveratrol A-H) and the HMBC correlations disclosed the connectivity of these partial structures to give the total planar structure which composed of two similar resveratrol trimer (trimer 1 and 2). The ROESY spectra and the coupling constant in ^1H NMR spectra were useful to determine the relative stereochemistry. Bioactivities In our bioactive screening experiment for above-mentioned compounds including their derivatives, we examined in vitro cytotoxicity on a panel of human tumor cell lines. Among isolates, hopeaphonol (21) and vaticanol C (11) displayed significant cytotoxicity on KB cells with ED_<50> values of 1.2 and 1.3μg/ml. Through acetylation, the activity was enhanced. The acetate of 32 showed the most potent and selective cytotoxic activity with ED_<50> values of 0.6, 0.7 and 2.0μg/ml on KB, 1A9 and MCF-7 cells, respectively. Anti-oxidant and SOD like activity of the isolates were also examined and the total results suggested that this type of phenolic compounds generally showed the activities.
天然有機化合物討論会の論文
2000-10-01

83(P-83) フタバガキ科植物のスチルベンオリゴマーの構造と生物活性(ポスター発表の部)

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