potentillanoside A | 1309589-79-4

• 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: potentillanoside A
• 英文别名: 2α,19α-dihydroxy-3-oxours-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester；Potentillanoside A；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,11R,12aR,14bS)-1,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-2H-picene-4a-carboxylate
• CAS: 1309589-79-4
• 化学式: C₃₆H₅₆O₁₀
• 分子量: 648.835
• InChiKey: PTHJWWHWYWHNNN-AOUBIGNISA-N

物化性质

• 沸点：
  755.0±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  46
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

安全信息

• 储存条件：
  室温

制备方法与用途

委陵菜苷A是一种具有保肝作用的天然化合物。

反应信息

• 作为反应物：
  描述：

  potentillanoside A 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

• Triterpenoids from the Roots of Sanguisorba tenuifolia var. Alba
  作者：Hai-Xue Kuang、Hong-Wei Li、Qiu-Hong Wang、Bing-You Yang、Zhi-Bin Wang、Yong-Gang Xia

  DOI：10.3390/molecules16064642

  日期：——

  The ethyl acetate soluble fraction from the roots of Sanguisorba tenuifolia was found to have a hypoglucemic effect in alloxan-induced diabetic rats. Two new triterpenoids, identified as 2-oxo-3β,19α-dihydroxyolean-12-en-28-oic acid β-D-gluco-pyranosyl ester (1) and 2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid β-D-glucopyranosyl ester (4) were isolated from this fraction, along with thirteen known triterpenoids. Their structures were elucidated by chemical and spectroscopic methods. All these compounds demonstrated inhibitory activities against α-glucosidase with IC50 values in the 0.62-3.62 mM range.

  研究发现，从 Sanguisorba tenuifolia 根部提取的乙酸乙酯可溶性馏分对阿脲诱导的糖尿病大鼠具有降血糖作用。从该馏分中分离出了两种新的三萜类化合物，即 2-氧代-3β,19α-二羟基乌苏-12-烯-28-酸 β-D-吡喃葡萄糖酯（1）和 2α,19α-二羟基-3-氧代-12-乌苏-28-酸 β-D-吡喃葡萄糖酯（4），以及 13 种已知的三萜类化合物。通过化学和光谱方法阐明了它们的结构。所有这些化合物都对α-葡萄糖苷酶有抑制作用，其 IC50 值在 0.62-3.62 mM 之间。
• 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.