19α-hydroxy-2,3-secours-12-en-2,3,28-trioic acid 28-O-β-D-glucopyranosyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 19α-hydroxy-2,3-secours-12-en-2,3,28-trioic acid 28-O-β-D-glucopyranosyl ester
• 英文别名: potentillanoside D；cecropiacic acid 28-O-β-D-glucopyranosyl ester；2-[(1R,2R,4aR,4bS,6aS,9R,10R,10aS,12aR)-1-(carboxymethyl)-10-hydroxy-1,4a,4b,9,10-pentamethyl-6a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2H-chrysen-2-yl]-2-methylpropanoic acid
• 化学式: C₃₆H₅₆O₁₂
• 分子量: 680.833
• InChiKey: WBZXSDMOAYYMQC-LHZLNHRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  211
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  19α-hydroxy-2,3-secours-12-en-2,3,28-trioic acid 28-O-β-D-glucopyranosyl ester 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 葡萄糖
  参考文献：
  名称：

  Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina

  摘要：

  A methanol extract from the tuberous roots of Potentilla anserina (Rosaceae) exhibited hepatoprotective effects against D-galactosamine (D-GalN)/lipopolysaccharide-induced liver injuries in mice. Six triterpene 28-O-monoglucopyranosyl esters, potentillanosides A-F, were isolated from the extract along with 32 known compounds, including 15 triterpenes. The structures of potentillanosides A-F were determined on the basis of spectroscopic properties and chemical evidence. Four ursane-type triterpene 28-O-monoglycosyl esters, potentillanoside A (IC50 = 46.7 mu M), 28-O-beta-D-glucopyranosyl pomolic acid (IC50 = 9.5 - mu M), rosamutin (IC50 = 35.5 mu M), and kaji-ichigoside F1 (IC50 = 14.1 mu M), inhibited D-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. Among these four triterpenes, potentillanoside A, rosamutin, and kaji-ichigoside F1 exhibited in vivo hepatoprotective effects at doses of 50-100 mg/kg, p.o. The mode of action was ascribable to the reduction in cytotoxicity caused by D-GalN. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.03.002

文献信息

• Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina
  作者：Toshio Morikawa、Kiyofumi Ninomiya、Katsuya Imura、Takahiro Yamaguchi、Yoshinori Akagi、Masayuki Yoshikawa、Takao Hayakawa、Osamu Muraoka

  DOI：10.1016/j.phytochem.2014.03.002

  日期：2014.6

  A methanol extract from the tuberous roots of Potentilla anserina (Rosaceae) exhibited hepatoprotective effects against D-galactosamine (D-GalN)/lipopolysaccharide-induced liver injuries in mice. Six triterpene 28-O-monoglucopyranosyl esters, potentillanosides A-F, were isolated from the extract along with 32 known compounds, including 15 triterpenes. The structures of potentillanosides A-F were determined on the basis of spectroscopic properties and chemical evidence. Four ursane-type triterpene 28-O-monoglycosyl esters, potentillanoside A (IC50 = 46.7 mu M), 28-O-beta-D-glucopyranosyl pomolic acid (IC50 = 9.5 - mu M), rosamutin (IC50 = 35.5 mu M), and kaji-ichigoside F1 (IC50 = 14.1 mu M), inhibited D-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. Among these four triterpenes, potentillanoside A, rosamutin, and kaji-ichigoside F1 exhibited in vivo hepatoprotective effects at doses of 50-100 mg/kg, p.o. The mode of action was ascribable to the reduction in cytotoxicity caused by D-GalN. (C) 2014 Elsevier Ltd. All rights reserved.