53(P-17) 巨峰(Vitis vinifera 'Kyohou')のオリゴスチルベンの構造と化学(ポスター発表の部)
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Many oligostilbenes with various type of the molecular skeleton have been isolated mainly from the following plant families: Vitaceae, Dipterocarpaceae, Leguminosae. Cyperaceae and Gnetaceae. But, oligostilbenes isolated from Vitaceaeous plants are chemically different from those from other families as shown in the cases of -viniferin (a resveratrol dimer) and hopeaphenol (a resveratrol tetramer). (+)-Viniferin seems to be a biogenetically important precursor of many oligostilbenes isolated from Vitaceaeous plants as shown in Scheme 1 and 2. We describe herein the structures of three new resveratrol tetramers, (+)-viniferols A. B and C from Vitis vinifera 'Kyohou.' (+)-Viniferol A has bicyclo[6.3.0]undecane ring system in its structure. The whole structure including absolute configuration was determined by spectral means and biogenetic considerations. On the other hand, (+)-viniferol B and (+)- -viniferol C have the same planar structure bearing bicyclo[5.3.0]undecane ring system. Their stereochemistries around 7-membered ring were determined by NOE experiment and calculation of J-values of the protons. Moreover, we demonstrate the biomimic transformations of (+)- -viniferin to resveratrol dimers and tetramers. By acid treatment of (+)- -viniferin, (+)-ampelopsin B, (-)-ampelopsin D and (+)-ampelopsin F were obtained. (+)-Ampelopsin A was obtained by alkaline treatment of the 7b,8b-epoxide of (+)- -viniferin pentaacetate. (+)-e-viniferin was oxidized in the mixture of horseradish peroxidase and hydrogen peroxide to give (-)-vitisn B. (-)-Vitisin B was further converted to (+)-vitisin A, which was transformed to (+)-vitisin D, by acid treatment. As the results, the absolute configurations of these oligostilbenes were determined.
- 天然有機化合物討論会の論文
- 2002-09-01
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