rubiarbonol F | 130295-73-7

• 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: rubiarbonol F
• 英文别名: (1R,3S,3aR,5aS,5bS,6S,7aR,9R,10R,11aS,13aR,13bR)-3a-(hydroxymethyl)-5a,8,8,11a,13a-pentamethyl-3-propan-2-yl-1,2,3,4,5,5b,6,7,7a,9,10,11,13,13b-tetradecahydrocyclopenta[a]chrysene-1,6,9,10-tetrol
• CAS: 130295-73-7
• 化学式: C₃₀H₅₀O₅
• 分子量: 490.724
• InChiKey: KJXUHHARWYEHNL-ZEUDKGLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 rubiarbonol F 在 吡啶 作用下， 以51%的产率得到Acetic acid (1R,3S,3aR,5aS,5bS,6S,7aR,9R,10R,11aS,13aR,13bS)-1,9,10-triacetoxy-3a-acetoxymethyl-3-isopropyl-5a,8,8,11a,13a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-6-yl ester
  参考文献：
  名称：

  Absolute Stereostructures of New Arborinane-Type Triterpenoids and Inhibitors of Nitric Oxide Production from Rubia yunnanensis

  摘要：

  The aqueous acetone extract from the roots of a Chinese herbal medicine, Rubia yunnanensis, showed a potent inhibitory effect on nitric oxide production in lipopolysaccharide-activated macrophages. Five new arborinane-type triterpenes, rubianols-a (1), -b (2), -c (3), -d (4), and -e (5), and a new arborinane-type triterpene glycoside, rubianoside I (6), were isolated from the herbal crude extract together with 10 known compounds. The absolute stereostructures of 1-6 were determined on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The effects of the isolated constituents on nitric oxide production in lipopolysaccharide-activated macrophages were examined, and several triterpenes were found to show inhibitory activity.

  DOI：

  10.1021/np0205710