(1R,2S,3R)-2-(3,5-Dihydroxy-phenyl)-1-[hydroxy-(4-hydroxy-phenyl)-methyl]-3-(4-hydroxy-phenyl)-indan-4,6-diol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1R,2S,3R)-2-(3,5-Dihydroxy-phenyl)-1-[hydroxy-(4-hydroxy-phenyl)-methyl]-3-(4-hydroxy-phenyl)-indan-4,6-diol
• 英文别名: Leachinol f；(1R,2S,3R)-2-(3,5-dihydroxyphenyl)-1-[hydroxy-(4-hydroxyphenyl)methyl]-3-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol
• 化学式: C₂₈H₂₄O₇
• 分子量: 472.494
• InChiKey: PRITZUOAMIVROM-UYCXCSBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  142
• 氢给体数：
  7
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  白藜芦醇 在 Glycine max peroxidase 、 双氧水 作用下， 以 phosphate buffer 、 丙酮 为溶剂， 反应 0.5h， 生成 5-[(E)-2-[(2S,3S)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]ethenyl]benzene-1,3-diol 、 (+/-)-pallidol 、 (1R,2S,3R)-2-(3,5-Dihydroxy-phenyl)-1-[hydroxy-(4-hydroxy-phenyl)-methyl]-3-(4-hydroxy-phenyl)-indan-4,6-diol
  参考文献：
  名称：

  Biomimic transformation of resveratrol

  摘要：

  Resveratrol was treated with several kinds of peroxidases and inorganic reagents so as to prepare E-viniferin. Among several inorganic reagents, which were investigated in this study, thallium(III) nitrate in methanol gave (+/-)-epsilon-viniferin in the yield of 68%. On the other hand, peroxidases did not lead to F-viniferin, but some stilbenedimers such as pallidol, resveratrol trans-dehydrodimer, and leachianol F were obtained. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.023

文献信息

• Dimerization of Resveratrol by the Grapevine Pathogen <i>Botrytis cinerea</i>
  作者：Robert H. Cichewicz、Samir A. Kouzi、Mark T. Hamann

  DOI：10.1021/np990266n

  日期：2000.1.1

  Resveratrol (trans-3,4',5-trihydroxystilbene) is produced by grapes (Vitis spp.) in response to microbial attack by the fungal grapevine pathogen Botrytis cinerca. Several reports indicate that pathogenic B. cinerca strains are capable of biotransforming resveratrol into an assortment of unidentified oxidized metabolites as a means of reducing the antifungal effects of resveratrol and facilitating Botrytis invasion into host-plant tissues. Studies utilizing growing incubations of Botrytis cinerea ATCC 11542 with resveratrol resulted in the production of three new (restrytisols A-C) (1-3) and three known (resveratrol trans-dehydrodimer, leachinol F, and pallidol) oxidized resveratrol dimers. All of the metabolites were evaluated for their anti-HIV-1, cytotoxic, and cyclooxygenase (COX) I and COX II inhibitory activities.
• Biomimic transformation of resveratrol
  作者：Yoshiaki Takaya、Kenji Terashima、Junko Ito、Yue-Hua He、Maki Tateoka、Naho Yamaguchi、Masatake Niwa

  DOI：10.1016/j.tet.2005.08.023

  日期：2005.10

  Resveratrol was treated with several kinds of peroxidases and inorganic reagents so as to prepare E-viniferin. Among several inorganic reagents, which were investigated in this study, thallium(III) nitrate in methanol gave (+/-)-epsilon-viniferin in the yield of 68%. On the other hand, peroxidases did not lead to F-viniferin, but some stilbenedimers such as pallidol, resveratrol trans-dehydrodimer, and leachianol F were obtained. (c) 2005 Elsevier Ltd. All rights reserved.