(3β)-lup-20(29)-en-3-yl stearate

• 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: (3β)-lup-20(29)-en-3-yl stearate
• 英文别名: lupeoyl stearate；[(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] octadecanoate
• 化学式: C₄₈H₈₄O₂
• 分子量: 693.194
• InChiKey: UCCCAIOWWOYXLE-GJYVAEPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.9
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3β)-lup-20(29)-en-3-yl stearate 在 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 羽扇豆醇 、 硬脂酸
  参考文献：
  名称：

  来自 Koelpinia linearis 的羽扇豆醇的不寻常同源长链链烷酸酯

  摘要：

  摘要 5 个不同寻常的羽扇豆醇长链链烷酸(C 14 C 18 ) 酯是从koelpinia linearis 的甲醇提取物中分离出来的，并通过化学和光谱方法，包括13 C NMR 进行表征。光谱分配是通过 APT 和 DEPT 技术实现的。

  DOI：

  10.1016/0031-9422(95)00687-7
• 作为产物：
  描述：

  羽扇豆醇 、 硬脂酸 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3β)-lup-20(29)-en-3-yl stearate
  参考文献：
  名称：

  Gastroprotective properties of Lupeol-derived ester: Pre-clinical evidences of Lupeol-stearate as a potent antiulcer agent

  摘要：

  Lupeol (1) was isolated from hexane branch extract of Maytenus salicifolia and the Lupeol stearate (2), Lupeol palmitate (3), Lupeol myristate (4), Lupeol laurate (5) and Lupeol caprylate (6) were obtained reacting 1 with an adequate carboxylic acid. Swiss mice were treated with vehicle, carbenoxolone or Lupeol esters before administration of ethanol/HCl or indomethacin. Additionally, the involvement of nitric oxide (NO), sulfhydryl compounds (NP-SH), alpha-2 adrenergic receptors (alpha 2-AR) and prostaglandins (PGE) in antiulcer effects was investigated using appropriate inhibitors or antagonist. Oxidative and inflammatory parameters were measured after euthanasia and anti-secretory effects was evaluated in pylorus-ligated rats. Ethanol/HCl ulcerated the gastric mucosa by 64.45 +/- 6.58 mm(2), which the oral treatment with 1, 4 and 6 (10 mg/kg), and 3 and 5 (30 mg/kg) reduced the lesion area. Interestingly, 2 reduced the gastric ulcer by oral route in a potent and dosedependent manner (ED50 = 0.40 mg/kg), which was accompanied by the increase in reduced glutathione levels and by the reduction of lipids peroxidation and myeloperoxidase and superoxide dismutase activities. Moreover, 2 (0.1 mg/kg) also prevented the ulcerogenesis by intraperitoneal route. The participation of NO, NP-SH, alpha 2-AR and PGE in 2-mediated gastroprotection was confirmed. In indomethacin-induced ulcer, 2 (1 mg/kg, p.o) also reduced the ulcer area and increased the PGE 2 levels. However, 2 did not alter the gastric acid secretion. Therefore, these findings indicate that the obtention of 2 potentiated the antiulcer activity of 1 and that this compound can elicit gastroprotective action due a diversified mode of action.

  DOI：

  10.1016/j.cbi.2020.108964