cis-ε-viniferin | 62218-08-0

• 物质功能分类: 天然产物 - 酚类
• 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-ε-viniferin
• 英文别名: 3-(3,5-Dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-4-hydroxystyryl]-2,3-dihydrobenzofuran；5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• CAS: 62218-08-0
• 化学式: C₂₈H₂₂O₆
• 分子量: 454.479
• InChiKey: FQWLMRXWKZGLFI-RJRFIUFISA-N

物化性质

• 熔点：
  approximate 157℃ (dec.)
• 溶解度：
  溶于甲醇；
• LogP：
  3.802 (est)

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

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

ε-Viniferin 是从 Vitis vinifera 提取得到的 Resveratrol 的二聚体，可有效抑制 CYP 家族酶，其 Ki 值范围在 0.5-20 μM 之间。ε-Viniferin 具有强大的抗氧化活性。

靶点

CYP 类别	IC50 (μM) 或 Ki (μM)
CYP2B6	3 μM (Ki, BROD)
CYP1A2	5 μM (Ki, EROD)
CYP3A4	10 μM (Ki, TST)
CYP4A	15 μM (IC50, LwOH)
CYP2E1	25 μM (IC50, CHZ)
CYP2A6	60 μM (Ki, COH)

反应信息

• 作为产物：
  描述：

  (+)-E-ε-viniferin 以 甲醇 为溶剂， 生成 cis-ε-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

• Identification of isomers of resveratrol dimer and their analogues from wine grapes by HPLC/MSn and HPLC/DAD-UV
  作者：Q.J. Kong、X.Y. Ren、N. Hu、C.R. Sun、Y.J. Pan

  DOI：10.1016/j.foodchem.2010.12.133

  日期：2011.7

  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.