(+)-catechin-5-O-β-glucuronide | 242807-38-1

• 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: (+)-catechin-5-O-β-glucuronide
• 英文别名: catechin-5-O-β-D-glucuronide；(2S,3S,4S,5R,6S)-6-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-chromen-5-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 242807-38-1
• 化学式: C₂₁H₂₂O₁₂
• 分子量: 466.398
• InChiKey: KGLMKAPOVXBIJB-FSDQAXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  6-[[[5-(2,4-二氧代嘧啶-1-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-3,4,5-三羟基四氢吡喃-2-羧酸 、 儿茶提取物 在 pooled male mouse liver microsomes 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 生成 (+)-catechin-5-O-β-glucuronide 、 (+)-catechin 5-O-β-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

文献信息

• Preparation and Characterization of Catechin Sulfates, Glucuronides, and Methylethers with Metabolic Interest
  作者：Susana González-Manzano、Ana González-Paramás、Celestino Santos-Buelga、Montserrat Dueñas

  DOI：10.1021/jf803140h

  日期：2009.2.25

  for which sufficient amounts of them are required that cannot be obtained by isolation from biological fluids. This paper describes the preparation of the methyl, sulfate, and glucuronide derivatives of catechins using different chemical syntheses and their characterization by HPLC−DAD−ESI/MS. MS2 fragmentation of the compounds was also described that allowed the determination of the location of the different

  儿茶素是许多植物食品中与健康促进有关的主要多酚。在人类有机体中，它们主要代谢为不同的结合物（硫酸盐，葡糖醛酸苷和甲基醚），这些结合物在血浆中进一步发现，将有助于与母体化合物摄入相关的生物学效应。循环代谢物可能具有与原始化合物不同的生物学特性，因此，重要的是评估其活性，为此需要足够量的代谢物，而这些量不能通过从生物体液中分离获得。本文介绍了使用不同化学合成方法制备儿茶素的甲基，硫酸盐和葡萄糖醛酸衍生物，并通过HPLC-DAD-ESI / MS对其进行了表征。MS 2还描述了化合物的断裂，从而可以确定儿茶素糖苷配基上不同取代基的位置。优化的程序允许制备在3'和4'位置缀合的（epi）儿茶素硫酸盐，葡糖醛酸苷和甲基醚，以及在5和7位置缀合的硫酸盐，具有令人满意的收率，可以通过半制备型HPLC进一步分离，考虑到它们在体外/离体测定中的用途。