Vitisin A and cis-Vitisin A, Strongly Hepatotoxic Plant Oligostilbenes from Vitis coignetiae (Vitaceae)

Yoshiteru Oshima; Akio Kamijou; Hiroshi Moritani; Kei ichi Namao; Yasushi Ohizumi

doi:10.1021/jo00056a016

Vitisin A and cis-Vitisin A, Strongly Hepatotoxic Plant Oligostilbenes from Vitis coignetiae (Vitaceae)

Yoshiteru Oshima, Akio Kamijou, Hiroshi Moritani, Kei ichi Namao, Yasushi Ohizumi

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

The methanolic extract of one of the common Vitaceaeous plants, Vitis coignetiae, showed marked prevention against injuries of primary cultured rat liver cells induced by carbon tetrachloride and d-galactosamine. Activity-guided fractionation of the extract resulted in the isolation of not only an antihepatotoxic stilbene derivative, ϵ-viniferin, but also novel oligostilbenes, vitisin A and its stereoisomer cis-vitisin A as a mixture. The structures of the oligostilbenes have been determined on the basis of spectroscopic evidence, especially by 2D NMR methods such as HMBC spectra of degradative products. The mixture of vitisin A and cis-vitisin A was found to cause marked liver lesions in mice.

Original language	English
Pages (from-to)	850-853
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	58
Issue number	4
DOIs	https://doi.org/10.1021/jo00056a016
Publication status	Published - 1993 Jan 1

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00056a016

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abstract = "The methanolic extract of one of the common Vitaceaeous plants, Vitis coignetiae, showed marked prevention against injuries of primary cultured rat liver cells induced by carbon tetrachloride and d-galactosamine. Activity-guided fractionation of the extract resulted in the isolation of not only an antihepatotoxic stilbene derivative, ϵ-viniferin, but also novel oligostilbenes, vitisin A and its stereoisomer cis-vitisin A as a mixture. The structures of the oligostilbenes have been determined on the basis of spectroscopic evidence, especially by 2D NMR methods such as HMBC spectra of degradative products. The mixture of vitisin A and cis-vitisin A was found to cause marked liver lesions in mice.",

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AU - Oshima, Yoshiteru

AU - Kamijou, Akio

AU - Moritani, Hiroshi

AU - Namao, Kei ichi

AU - Ohizumi, Yasushi

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AB - The methanolic extract of one of the common Vitaceaeous plants, Vitis coignetiae, showed marked prevention against injuries of primary cultured rat liver cells induced by carbon tetrachloride and d-galactosamine. Activity-guided fractionation of the extract resulted in the isolation of not only an antihepatotoxic stilbene derivative, ϵ-viniferin, but also novel oligostilbenes, vitisin A and its stereoisomer cis-vitisin A as a mixture. The structures of the oligostilbenes have been determined on the basis of spectroscopic evidence, especially by 2D NMR methods such as HMBC spectra of degradative products. The mixture of vitisin A and cis-vitisin A was found to cause marked liver lesions in mice.

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