4-[3-(3,5-dimethoxyphenyl)-5-[(Z)-2-(3,5-dimethoxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-2-yl]phenol | 231300-43-9

• 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: 4-[3-(3,5-dimethoxyphenyl)-5-[(Z)-2-(3,5-dimethoxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-2-yl]phenol
• CAS: 231300-43-9
• 化学式: C₃₂H₃₀O₆
• 分子量: 510.587
• InChiKey: VWAPPSRYPVADPA-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  紫檀芪 在 horseradish peroxidase type II 、 双氧水 作用下， 生成 4-{3-(3,5-Dimethoxy-phenyl)-5-[(E)-2-(3,5-dimethoxy-phenyl)-vinyl]-2,3-dihydro-benzofuran-2-yl}-phenol 、 β-[4-[(1E)-2-(3,5-dimethoxyphenyl)-ethenyl]phenoxy]-α-(4-hydroxyphenyl)-3,5-dimethoxybenzeneethanol 、 4-[3-(3,5-dimethoxyphenyl)-5-[(Z)-2-(3,5-dimethoxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-2-yl]phenol
  参考文献：
  名称：

  Kinetic mechanism and product characterization of the enzymatic peroxidation of pterostilbene as model of the detoxification process of stilbene-type phytoalexins

  摘要：

  The enzymatic peroxidation of pterostilbene, a strong antifungal belonging to the stilbene family, by peroxidase (POX), is reported for the first time as a model of phytoalexin detoxification carried out by the enzymatic pool of pathogens. Kinetic characterization of the pterostilbene oxidation reaction pointed to an optimum pH of 7.0, at which value the thermal stability of POX was studied. Moreover, the data showed that pterostilbene inhibits POX activity at high concentrations of substrate. Several kinetic parameters, including V-max K-m and K-I, were calculated and values of 0.16 Delta Abs min(-1), 14.61 mu M, and 31.41 mu M were reported. To understand the possible physiological role of this reaction in the phytoalexin detoxification process, the products of pterostilbene oxidation were identified using HPLC-MS and a radical-radical coupling reaction mechanism was proposed. Three main products with a high molecular weight and pronounced hydrophobicity were identified: pterostilbene cis dehydromer, pterostilbene trans dehydromer and pterostilbene open dimer. The dimeric structures of these molecules indicate that the pterostilbene oxidation reaction took place at the 4'-OH position of the hydroxystilbenic moieties and the three above mentioned dimeric products were found, due to the ability of electron-delocalized radicals to couple at various sites. Finally, the capacity of cyclodextrins (CDs) as starch model molecules in plants to complex both the substrate and the products of the oxidation reaction was evaluated. The inhibition process of POX activity was modified at high pterostilbene concentrations due to sequestering of the substrate reaction and to the different affinity of the reaction products for CDs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.10.009