silybin A-4''-Ο-β-D-glucuronide | 717098-34-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素苷
• 英文名称: silybin A-4''-Ο-β-D-glucuronide
• 英文别名: silybin A-4''-O-β-D-glucuronide；silybin A-4''-O-β-glucuronide；silybin A 20-O-β-glucuronide；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-[(2R,3R)-2-(hydroxymethyl)-6-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-2,3-dihydro-1,4-benzodioxin-3-yl]-2-methoxyphenoxy]oxane-2-carboxylic acid
• CAS: 717098-34-5
• 化学式: C₃₁H₃₀O₁₆
• 分子量: 658.57
• InChiKey: MFAOFQAVDHJBEL-YRTGQMBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  47.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  251.36
• 氢给体数：
  8.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  水飞蓟宾 在 Streptomyces sp. M₅₂₁₀₄ 作用下， 以 aq. buffer 为溶剂， 反应 96.0h， 生成 silybin A-7-Ο-β-D-glucuronide 、 silybin A-4''-Ο-β-D-glucuronide 、 silybin A-5-O-β-D-glucuronide
  参考文献：
  名称：

  Preparation of silybin phase II metabolites: Streptomyces catalyzed glucuronidation

  摘要：

  Flavonolignan silybin is a major component of the silymarin complex isolated from seeds of the milk thistle (Silybum marianum) having strong antioxidant and hepatoprotective effects, and also anticancer, chemoprotective, dermatoprotective and hypocholesterolemic activities. Natural silybin (silibinin in pharmacological literature) is a mixture of two diastereomers: silybin A and silybin B. Their metabolism is strongly linked to Phase II biotransformations and respective conjugates are rapidly excreted in bile and urine. Conjugation reactions of both silybins are strictly stereoselective. Therefore, optically pure compounds must be used for metabolic studies. The aim of this study was to obtain the glucuronidated metabolites of both silybin A and B. Streptomyces sp. strain M52104 was found to be a highly effective tool for the preparation of silybin A-20-O-beta-glucuronide, silybin B-20-O-beta-glucuronide, silybin glucuronide and silybin B-7-O-beta-glucuronide and minor amounts of silybin A and B-5-O-beta-glucuronide. The glucuronides, which were thoroughly characterized by MS and NMR spectroscopy, can be used as invaluable authentic standards in metabolic studies of both silybin diastereomers. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.02.008