(+)-5'-hydroxypinoresinol

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (+)-5'-hydroxypinoresinol
• 英文别名: rubiaxylm E；5-[(3S,3aR,6S,6aR)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-3-methoxybenzene-1,2-diol
• 化学式: C₂₀H₂₂O₇
• 分子量: 374.39
• InChiKey: BAMUCOAOGMYNQY-ISZNXKAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  松脂酚 以 二甲基亚砜 为溶剂， 反应 24.0h， 以4 mg的产率得到(+)-5'-hydroxypinoresinol
  参考文献：
  名称：

  Biotransformation of lignans: a specific microbial oxidation of (+)-eudesmin and (+)-magnolin by Aspergillus niger

  摘要：

  Biotransformation of the lignans, (+)-eudesmin, (+)-magnolin and (+)-yangabin, by Aspergillus niger has been investigated. (+)-Eudesmin was metabolized and transformed to (+)-de-4'-0-methyleudesmin and (+)-pinoresinol. Additionally, (+)-pinoresinol was examined and oxidized to (+)-5'-hydroxypinoresinol. (+)-Magnolin was transformed to (+)-de-0-methylmagnolin and (+)-de-4'-0-methyl-5'-hydroxymagnolin. In these metabolic processes, other products were not generated, although(+)-yangabin and (+)-de-4'-0-methyl-5'-hydroxymagnolin were hardly metabolized by this fungus. This suggested that the veratryl and guaiacyl groups of these lignans were possibly metabolized preferentially, with oxidation proceeding predominantly through de-0-methylation at the p-position of veratryl groups. By contrast, 3,4,5-trimethoxyphenyl and 4,5-dihydroxy-3-methoxyphenyl groups of this type of lignan were stable and not attacked by A. niger. The structures of metabolic products were determined by spectroscopic methods as well as by comparison of spectral data with those of known related compounds.

  DOI：

  10.1016/s0031-9422(00)90836-7

文献信息

• Biotransformation of lignans: a specific microbial oxidation of (+)-eudesmin and (+)-magnolin by Aspergillus niger
  作者：Mitsuo Miyazawa、Hiroyuki Kasahara、Hiromu Kameoka

  DOI：10.1016/s0031-9422(00)90836-7

  日期：1993.12

  Biotransformation of the lignans, (+)-eudesmin, (+)-magnolin and (+)-yangabin, by Aspergillus niger has been investigated. (+)-Eudesmin was metabolized and transformed to (+)-de-4'-0-methyleudesmin and (+)-pinoresinol. Additionally, (+)-pinoresinol was examined and oxidized to (+)-5'-hydroxypinoresinol. (+)-Magnolin was transformed to (+)-de-0-methylmagnolin and (+)-de-4'-0-methyl-5'-hydroxymagnolin. In these metabolic processes, other products were not generated, although(+)-yangabin and (+)-de-4'-0-methyl-5'-hydroxymagnolin were hardly metabolized by this fungus. This suggested that the veratryl and guaiacyl groups of these lignans were possibly metabolized preferentially, with oxidation proceeding predominantly through de-0-methylation at the p-position of veratryl groups. By contrast, 3,4,5-trimethoxyphenyl and 4,5-dihydroxy-3-methoxyphenyl groups of this type of lignan were stable and not attacked by A. niger. The structures of metabolic products were determined by spectroscopic methods as well as by comparison of spectral data with those of known related compounds.