白头翁皂苷E-2 | 244202-36-6

• 物质功能分类: 生物化工 - 提取物
• 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: 白头翁皂苷E-2
• 英文名称: oleanolic acid 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside
• 英文别名: 3-O-β-D-glucopyranosyl(1→4)-β-D-glucopyranosyl-(1→3)α-L-rhamnopyranosyl(1→2)-α-L- arabinopyranosyloleanolic acid；oleanolic acid 3-O-[O-beta-D-glucopyranosyl-(1->4)-O-beta-D-glucopyranosyl-(1->3)-O-alpha-L-rhamnopyranosyl-(1->2)-alpha-L-arabinopyranoside]；(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 244202-36-6
• 化学式: C₅₃H₈₆O₂₁
• 分子量: 1059.25
• InChiKey: VDRZQZWUCOHKED-BXROMGGZSA-N

物化性质

• 熔点：
  235-237 °C
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  74
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  334
• 氢给体数：
  12
• 氢受体数：
  21

制备方法与用途

生物活性

Pulchinenoside E2 (Compound 8) 是从 Pulsatilla chinensis 的根中分离出的三萜皂苷。Pulchinenoside E2 对 HL-60 白血病细胞具有细胞毒性，IC50 值为 2.6 µg/mL。

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 以25 mg的产率得到白头翁皂苷E-2
  参考文献：
  名称：

  Concise synthesis of two natural triterpenoid saponins, oleanolic acid derivatives isolated from the roots of Pulsatilla chinensis

  摘要：

  The first synthesis of two natural triterpenoid saponins, which were isolated from the roots of Pulsatilla chinensis and exhibited excellent in vitro cytotoxic activity against HL-60 cells, was concisely achieved in a convergent approach. We employed an odourless 2-methyl-5-tert-butylphenyl (Mbp) thioglycoside and trichloroacetimidate donors in one-pot reaction as a key step. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2009.05.011