3'-O-methyl-(+)-catechin-7-O-β-glucuronide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3'-O-methyl-(+)-catechin-7-O-β-glucuronide
• 英文别名: (2S,3S,4S,5R,6S)-6-[[(2R,3S)-3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-chromen-5-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₂₂H₂₄O₁₂
• 分子量: 480.425
• InChiKey: WMVRRRYTJXAVND-CNDVCMBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  儿茶提取物 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 3'-O-methyl-(+)-catechin-7-O-β-glucuronide 、 3′-O-methyl-(+)-epicatechin-7-O-glucuronide
  参考文献：
  名称：

  Synthesis and Quantitative Analysis of Plasma-Targeted Metabolites of Catechin and Epicatechin

  摘要：

  Grape seed polyphenolic extract (GSPE) rich in the flavan-3-ols (+)-catechin and (-)-epicatechin beneficially modulates Alzheimer's Disease phenotypes in animal models. The parent molecules in the extract are converted to a series of methylated and glucuronidated derivatives. To fully characterize these metabolites and establish a robust quantitative assay of their levels in biological fluids, we have implemented a partial synthetic approach utilizing chemical methylation followed by enzymatic glucuronidation. Liquid chromatography/time-of-flight mass spectrometry (LC-TOF-MS) and nuclear magnetic resonance (NMR) spectroscopy were used to assign unequivocal structures to the compounds. An analytical method using solid-phase extraction and LC-MS/MS in selective reaction monitoring mode (SRM) was validated for their quantitation in plasma. These studies provide a basis for improvements in future work on the bioavailability, metabolism, and mechanism of action of metabolites derived from dietary flavan-3-ols in a range of interventions.

  DOI：

  10.1021/jf505922b