P-17 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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Stilbenoids represented by resveratrol have drawn much attention from the chemical community due to their roles in food and beverage, and because of their diverse biological activities. These compounds, either in glycosylated or non-glycosylated form, are typically found as oligomers in limited plant families such as Dipterocarpaceae, Vitaceae, Cyperaceae, and Gnetaceae. The rich structural variation and multifunctional bioactivity make stilbenoid oligomers interesting targets for detailed phytochemical investigations. Dipterocarpaceaeous plants are well-known to contain resveratrol oligomers, and their occurrences in Vatica, Vateria, Shorea, and Hopea genera have been disclosed in our previous works. The genus Upuna, which belongs to the tribe Dipterocarpeae in the largest subfamily Dipterocarpoideae, comprises monotypic species and is rare species endemic to Indonesia. Although structural elucidations of resveratrol oligomers have been made in some of the above-mentioned related genera, no examination of Upuna has been reported yet. In our current phytochemical studies of Dipterocarpaceae, the chemical constituents of U. borneensis were examined, and 17 new resveratrol oligomers were isolated, together with 18 known resveratrol derivatives. The structural elucidation of them, and their NMR characteristics due to steric hindrance are presented. 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 the isolates, vaticanol C exhibited growth suppression and induction of apoptosis via the loss of mitochondrial membrane potential and consequent caspases activation. The detailed mechanisms are not clearly understood. We decided to attempt to gain further insight into the mechanism underlying vaticanol C induced apoptosis in HL-60 cells. Treatment of HL-60 cells with vaticanol C was found to cause a marked decrease in the level or phosphorylated extracellular signal-regulated kinase (ERK) concurrent with inhibited phosphorylation or its upstream kinase mitogen-activates protein kinase kinase (MEK). Moreover, exposure to vaticanol C led to a significant reduction in the level or phosphorylated Akt. Thus, vaticanol C induced inbibition of both ERK and Akt phospborylation, resulting in reduced phosphorylation of Bad. These results suggest that vaticanol C might induce apoptosis via a mechanism involving activation of Bad through disruption of pro-survival signaling pathways.
天然有機化合物討論会の論文
2007-08-24

P-17 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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