vitisin A

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: vitisin A
• 英文别名: (1S,8S,9R,16S)-9-[5-[2-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]-2-hydroxyphenyl]-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.02,7.014,17]heptadeca-2(7),3,5,10(17),11,13-hexaene-4,6,12-triol
• 化学式: C₅₆H₄₂O₁₂
• 分子量: 906.942
• InChiKey: XAXVWWYPKOGXSY-VLYVWKAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  68
• 可旋转键数：
  7
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  221
• 氢给体数：
  10
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  vitisin A 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以42 mg的产率得到(1S,6R,7S,11bS)-6-(5-{2-[(2S,3S)-3-(3,5-Dihydroxy-phenyl)-6-hydroxy-2-(4-hydroxy-phenyl)-2,3-dihydro-benzofuran-4-yl]-ethyl}-2-hydroxy-phenyl)-1,7-bis-(4-hydroxy-phenyl)-1,6,7,11b-tetrahydro-2-oxa-dibenzo[cd,h]azulene-4,8,10-triol
  参考文献：
  名称：

  Vitisin A and cis-vitisin A, strongly hepatotoxic plant oligostilbenes from Vitis coignetiae (Vitaceae)

  摘要：

  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, epsilon-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.

  DOI：

  10.1021/jo00056a016