(-)-quadrangularin A | 252557-25-8

• 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: (-)-quadrangularin A
• 英文别名: (1E,2S,3S)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-[(4-hydroxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol
• CAS: 252557-25-8
• 化学式: C₂₈H₂₂O₆
• 分子量: 454.479
• InChiKey: BIQMSWPBPAKGSE-PHPWSYFYSA-N

物化性质

• 沸点：
  723.5±48.0 °C(Predicted)
• 密度：
  1.488±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  121
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  白藜芦醇 、 (-)-quadrangularin A 在 horseradish peroxidase 、 双氧水 作用下， 以 水 、 丙酮 为溶剂， 反应 0.58h， 以14%的产率得到laetevirenol D
  参考文献：
  名称：

  Stilbene Oligomers from Parthenocissus laetevirens: Isolation, Biomimetic Synthesis, Absolute Configuration, and Implication of Antioxidative Defense System in the Plant

  摘要：

  Five new stilbene oligomers, laetevirenol A-E (4-8), were isolated from Parthenocissus laetevirens, together with three known stilbene oligomers (2, 3, and 9). The structures of the new compounds were elucidated by spectroscopic analysis, including 1D and 2D NMR experiments. Afterward the absolute configurations were determined. Biornimetic transformations revealed a possible biogenetic route, where stilbene trimers were enzymatically synthesized for the first time. In addition, their antioxidant activities were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The results showed that stilbene oligomers with an unusual phenanthrene moiety exhibited much stronger antioxidant activities. Thus, the photocatalyzed cyclization of stilbenes was supposed to be an antioxidant activity promoting transformation, which was hypothesized to play a role in the antioxidative defense system of the plant.

  DOI：

  10.1021/jo8001112
• 作为产物：
  描述：

  (-)-parthenocissin A 以 甲醇 为溶剂， 反应 2.0h， 以31%的产率得到(-)-quadrangularin A
  参考文献：
  名称：

  Stilbene Oligomers from Parthenocissus laetevirens: Isolation, Biomimetic Synthesis, Absolute Configuration, and Implication of Antioxidative Defense System in the Plant

  摘要：

  Five new stilbene oligomers, laetevirenol A-E (4-8), were isolated from Parthenocissus laetevirens, together with three known stilbene oligomers (2, 3, and 9). The structures of the new compounds were elucidated by spectroscopic analysis, including 1D and 2D NMR experiments. Afterward the absolute configurations were determined. Biornimetic transformations revealed a possible biogenetic route, where stilbene trimers were enzymatically synthesized for the first time. In addition, their antioxidant activities were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The results showed that stilbene oligomers with an unusual phenanthrene moiety exhibited much stronger antioxidant activities. Thus, the photocatalyzed cyclization of stilbenes was supposed to be an antioxidant activity promoting transformation, which was hypothesized to play a role in the antioxidative defense system of the plant.

  DOI：

  10.1021/jo8001112

文献信息

• US9185909B2
  申请人：——

  公开号：US9185909B2

  公开（公告）日：2015-11-17
• [EN] SYNTHESIS OF RESVERATROL-BASED NATURAL PRODUCTS<br/>[FR] SYNTHÈSE DE PRODUITS NATURELS À BASE DE RESVÉRATROL
  申请人：UNIV COLUMBIA

  公开号：WO2009038731A2

  公开（公告）日：2009-03-26

  Processes for synthesizing reveratrol-based oligomers are provided. In addition, reservatrol-based oligomer compounds free of plant extract are provided.
• Stilbene Oligomers from <i>Parthenocissus laetevirens</i>: Isolation, Biomimetic Synthesis, Absolute Configuration, and Implication of Antioxidative Defense System in the Plant
  作者：Shan He、Bin Wu、Yuanjiang Pan、Liyan Jiang

  DOI：10.1021/jo8001112

  日期：2008.7.1

  Five new stilbene oligomers, laetevirenol A-E (4-8), were isolated from Parthenocissus laetevirens, together with three known stilbene oligomers (2, 3, and 9). The structures of the new compounds were elucidated by spectroscopic analysis, including 1D and 2D NMR experiments. Afterward the absolute configurations were determined. Biornimetic transformations revealed a possible biogenetic route, where stilbene trimers were enzymatically synthesized for the first time. In addition, their antioxidant activities were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The results showed that stilbene oligomers with an unusual phenanthrene moiety exhibited much stronger antioxidant activities. Thus, the photocatalyzed cyclization of stilbenes was supposed to be an antioxidant activity promoting transformation, which was hypothesized to play a role in the antioxidative defense system of the plant.