cis-δ-viniferin

• 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: cis-δ-viniferin
• 英文别名: 5-[(Z)-2-[3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]benzene-1,3-diol
• 化学式: C₂₈H₂₂O₆
• 分子量: 454.479
• InChiKey: LILPTCHQLRKZNG-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  trans-δ-viniferin 以 甲醇 为溶剂， 生成 cis-δ-viniferin
  参考文献：
  名称：

  Identification of isomers of resveratrol dimer and their analogues from wine grapes by HPLC/MSn and HPLC/DAD-UV

  摘要：

  A facile method based on HPLC/(-)ESI-MSn is established for the analysis of seven isomers of resveratrol dimers and three of their analogues in Xinjiang wine grapes. The structures of these compounds are positively or tentatively determined. Among them, three are tentatively identified as new compounds. MSn experiments on the [M-H](-) ions provide abundant structural information, especially regarding the relative abundance of the key product ions, m/z 333 and 369 (385 in compound 3), which can be utilised to distinguish whether or not the compound identified contains the scaffold of the isomer of a resveratrol dimer. The relative abundance of key product ions remains unchanged as collision energy varies from 0.60 to 0.95 V. All the trans-, and cis-isomers could be identified by HPLC/DAD-UV spectra. The UV spectra of compounds 2 and 9 tentatively show cis and trans- configurations, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2010.12.133

文献信息

• pH-switched HRP-catalyzed dimerization of resveratrol: a selective biomimetic synthesis
  作者：Chang Li、Jing Lu、Xiaofei Xu、Ruilin Hu、Yuanjiang Pan

  DOI：10.1039/c2gc36288k

  日期：——

  A selective, concise and green biomimetic synthesis strategy of seven resveratrol dimers from natural resveratrol monomer as starting material is described. By succinct adjustment of environmental pH, the enzyme used, horseradish peroxidase (HRP), can perform in three distinctly different patterns and five dimers form with considerable selectivity. Two other derivative dimers are subsequently synthesized.

  本文介绍了一种以天然白藜芦醇单体为起始原料，选择性地、简洁地合成七种白藜芦醇二聚体的绿色仿生合成策略。通过简洁地调节环境 pH 值，所使用的辣根过氧化物酶（HRP）能以三种截然不同的模式发挥作用，并以相当高的选择性形成了五种二聚体。随后还合成了另外两种衍生物二聚体。
• Metabolism of stilbene phytoalexins by Botrytis cinerea: 1. Characterization of a resveratrol dehydrodimer
  作者：Anne-Céline Breuil、Marielle Adrian、Nadine Pirio、Philippe Meunier、Roger Bessis、Philippe Jeandet

  DOI：10.1016/s0040-4039(97)10622-0

  日期：1998.2

  Resveratrol, a grapevine phytoalexin, is metabolized by a laccase-like stilbene-oxidase of Botrytis cinerea, the causal organism for grey mould. Characterization of one major metabolite formed during this degradation process as a resveratrol dehydrodimer allowed us to precize the reaction mechanism of this enzyme on stilbenes. (C) 1998 Elsevier Science Ltd. All rights reserved.