大黄素甲醚-1-O-beta-D-葡萄糖苷 | 26296-54-8

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 大黄素甲醚-1-O-beta-D-葡萄糖苷
• 中文别名: 大黄素甲醚-8-O--D-葡萄糖苷；大黄素甲醚-1-O-BETA-D-葡萄糖苷
• 英文名称: physcion-8-O-β-D-glucoside
• 英文别名: physcion 8-O-glucoside；Physcion 8-glucoside；1-hydroxy-3-methoxy-6-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
• CAS: 26296-54-8
• 化学式: C₂₂H₂₂O₁₀
• 分子量: 446.411
• InChiKey: WLXGUTUUWXVZNM-DQMLXFRHSA-N

物化性质

• 熔点：
  235℃
• 沸点：
  796.3±60.0 °C(Predicted)
• 密度：
  1.567±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  10

制备方法与用途

生物活性

Physion 8-O-β-D-glucoside 是来自毛花叶的生物活性成分，可用于研究头晕。

化学性质

这种物质为淡黄色粉末，可溶于甲醇、乙醇和DMSO等有机溶剂，来源于大黄和何首乌。

用途

Physion 8-O-β-D-glucoside 可用于含量测定、鉴定及药理实验等。

反应信息

• 作为产物：
  描述：

  大黄素甲醚 在 盐酸 、 recombinant human UGT 1A₉ isoform 、 uridine-5′-diphosphoglucuronic acid 、 维生素 C 作用下， 反应 6.25h， 生成 大黄素甲醚-1-O-beta-D-葡萄糖苷
  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.