chrysophanol-1-O-glucuronide | 1202570-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: chrysophanol-1-O-glucuronide
• 英文别名: chrysophanol glucuronide；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(8-hydroxy-6-methyl-9,10-dioxoanthracen-1-yl)oxyoxane-2-carboxylic acid
• CAS: 1202570-48-6
• 化学式: C₂₁H₁₈O₁₀
• 分子量: 430.368
• InChiKey: LLBDMOMQVJJRNA-ZFORQUDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  171
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,3,8-trihydroxyanthraquinone 、 uridine-5′-diphosphoglucuronic acid 在 recombinant human UGT 1A₉ isoform 作用下， 反应 4.0h， 生成 chrysophanol-1-O-glucuronide 、 chrysophanol-8-O-glucuronide
  参考文献：
  名称：

  In vitro glucuronidation of five rhubarb anthraquinones by intestinal and liver microsomes from humans and rats

  摘要：

  Anthraquinones naturally distribute in many plants including rhubarb and have widespread applications throughout industry and medicine. Recent studies provided new insights in potential applications of these traditional laxative constituents. Glucuronidation was the main metabolic pathway of rhubarb anthraquinones in vivo. This study examined the activity and regioselectivity of glucuronidation of rhubarb anthraquinones (aloe-emodin, emodin, chrysophanol, physcion, rhein) in liver and intestinal microsomes from rats and humans, by comparing with the core structure danthron. All anthraquinones formed mono-glucuronides and, except for rhein, the conjugation sites of the main metabolites were unambiguously identified. Two minor glucuronides of emodin were first reported together with the dominant emodin-3-O-beta-D-glucuronide. The substitution on the anthraquinone ring was crucial to the activity and regioselectivity of glucuronidation. In general, the activity was decreased greatly with a beta-COOH (rhein), while enhanced dramatically with a beta-OH (emodin). Glucuronidation showed an absolute preference towards beta-OH, followed by alpha-OH and beta-alcoholic OH. The glucuronidation activity and regioselectivity also varied slightly with organs and species. All glucuronides of aloe-emodin, emodin, chrysophanol and physcion were formed by multiple human UGT isoforms with 1A9 being the most prominent in most cases. The UGT2B subfamily (2B7 and 2B15) only showed high activity towards a beta-OH. In conclusion, the substitution at the anthraquinone ring was crucial to the rate and preference of glucuronidation. The high glucuronidation activity of UGT1A9 towards anthraquinones highlighted potential drug interactions. (C) 2014 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.cbi.2014.05.006

文献信息

• In vitro glucuronidation of five rhubarb anthraquinones by intestinal and liver microsomes from humans and rats
  作者：Wenjin Wu、Nan Hu、Qingwen Zhang、Yaping Li、Peng Li、Ru Yan、Yitao Wang

  DOI：10.1016/j.cbi.2014.05.006

  日期：2014.8

  Anthraquinones naturally distribute in many plants including rhubarb and have widespread applications throughout industry and medicine. Recent studies provided new insights in potential applications of these traditional laxative constituents. Glucuronidation was the main metabolic pathway of rhubarb anthraquinones in vivo. This study examined the activity and regioselectivity of glucuronidation of rhubarb anthraquinones (aloe-emodin, emodin, chrysophanol, physcion, rhein) in liver and intestinal microsomes from rats and humans, by comparing with the core structure danthron. All anthraquinones formed mono-glucuronides and, except for rhein, the conjugation sites of the main metabolites were unambiguously identified. Two minor glucuronides of emodin were first reported together with the dominant emodin-3-O-beta-D-glucuronide. The substitution on the anthraquinone ring was crucial to the activity and regioselectivity of glucuronidation. In general, the activity was decreased greatly with a beta-COOH (rhein), while enhanced dramatically with a beta-OH (emodin). Glucuronidation showed an absolute preference towards beta-OH, followed by alpha-OH and beta-alcoholic OH. The glucuronidation activity and regioselectivity also varied slightly with organs and species. All glucuronides of aloe-emodin, emodin, chrysophanol and physcion were formed by multiple human UGT isoforms with 1A9 being the most prominent in most cases. The UGT2B subfamily (2B7 and 2B15) only showed high activity towards a beta-OH. In conclusion, the substitution at the anthraquinone ring was crucial to the rate and preference of glucuronidation. The high glucuronidation activity of UGT1A9 towards anthraquinones highlighted potential drug interactions. (C) 2014 Elsevier Ireland Ltd. All rights reserved.