1-O-[(2beta,3alpha,5Xi,9beta,18alpha)-2,3,19-三羟基-28-氧代乌苏-12-烯-28-基]-beta-D-吡喃葡萄糖 | 88515-58-6

• 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
• 中文名称: 1-O-[(2beta,3alpha,5Xi,9beta,18alpha)-2,3,19-三羟基-28-氧代乌苏-12-烯-28-基]-beta-D-吡喃葡萄糖
• 中文别名: 2-甲基十九烷基甲丙烯酰酸酯；野蔷薇苷
• 英文名称: rosamultin
• 英文别名: (2α,3β,19α)-2,3,19-trihydroxyurs-12-en-28-oic acid β-glucopyranosyl ester；2α,3β,19α-trihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranosyl ester；2α,3β,19α-trihydroxyurs-12-en-28-oic acid β-D-glucopyranosyl ester；2α,3β,19α-trihydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranoside；2α,3β,19α-trihydroxy-ursolic acid-28-O-β-D-glucopyranoside；β-D-glucopyranosyl 2α,3βa,19α-trihydroxyurs-12-en-28-oate；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 88515-58-6
• 化学式: C₃₆H₅₈O₁₀
• 分子量: 650.851
• InChiKey: MLKQAGPAYHTNQQ-BRDPIYJESA-N

物化性质

• 熔点：
  214-216 °C
• 沸点：
  741.5±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  46
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  10

制备方法与用途

生物活性

Rosamultin 是一种从 Potentilla anserina L. 分离出的 19 α-羟基熊果烷型三萜，能够抑制 HIV-1 蛋白酶。研究表明，Rosamultin 对 H2O2 诱导的氧化损伤和细胞凋亡具有保护作用。

靶点

Target	Value
HIV-1 protease	()

体外研究

从金蔷薇根部提取的 Rosamultin 在浓度为 100 μM 的情况下，能够抑制 HIV-1 蛋白酶活性 53%。

化学性质

Rosamultin 是一种白色结晶粉末，可溶于甲醇、乙醇和 DMSO 等有机溶剂。它来源于金樱根。

用途

野蔷薇苷具有抗氧化和抑菌的作用。

反应信息

• 作为产物：
  描述：

  potentillanoside C 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以97.2%的产率得到1-O-[(2beta,3alpha,5Xi,9beta,18alpha)-2,3,19-三羟基-28-氧代乌苏-12-烯-28-基]-beta-D-吡喃葡萄糖
  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

• Biotransformation of oleanolic acid by<i>Alternaria longipes</i>and<i>Penicillium adametzi</i>
  作者：Dai-Lin Liu、Ying Liu、Feng Qiu、Ying Gao、Jing-Ze Zhang

  DOI：10.1080/10286020.2010.547028

  日期：2011.2

  Microbial transformation of oleanolic acid (1) was carried out. Six transformed products (2-7) from 1 by Alternaria longipes and three transformed products (8-10) from 1 by Penicillium adametzi were isolated. Their structures were elucidated as 2,3,19-trihydroxy-ursolic acid-28-O--d-glucopyranoside (2), 2,3,19-trihydroxy-ursolic acid-28-O--d-glucopyranoside (3), oleanolic acid 28-O--d-glucopyranosyl ester (4), oleanolic acid-3-O--d-glucopyranoside (5), 3-O-(-d-glucopyranosyl)-oleanolic acid-28-O--d-glucopyranoside (6), 2,3,19a-trihydroxy-oleanolic acid-28-O--d-glucopyranoside (7), 21-hydroxyl oleanolic acid-28-O--d-glucopyranoside (8), 21-hydroxyl oleanolic acid (9), and 7,21-dihydroxyl oleanolic acid (10) based on the extensive NMR studies. Among them, 10 was a new compound and compounds 5 and 8-10 had stronger cytotoxic activities against Hela cell lines than the substrate. At the same time, it was reported for the first time in this paper that the skeletons of compounds 2 and 3 were changed from oleanane to uranane and seven glycosidation products were obtained by biotransformation.
• 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.