22α-(2-methylbutyryl)-3β,15α,16α,21β,28-pentahydroxyolean-12-ene

• 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: 22α-(2-methylbutyryl)-3β,15α,16α,21β,28-pentahydroxyolean-12-ene
• 英文别名: 22α-angeloyloxy-3β,15α,16α,28-tetrahydroxyolean-12-ene；racemosol-D；[(3R,4R,4aR,5S,6R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-3,5,6,10-tetrahydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-4-yl] 2-methylbutanoate
• 化学式: C₃₅H₅₈O₇
• 分子量: 590.841
• InChiKey: JWUMMTMOLWCPTC-ARTMIGJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  42
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  22α-(2-methylbutyryl)-3β,15α,16α,21β,28-pentahydroxyolean-12-ene 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以1.5 mg的产率得到R1-barrigenol
  参考文献：
  名称：

  α-Glucosidase inhibitory monoacylated polyhydroxytriterpenoids from the fruits of Barringtonia racemosa

  摘要：

  Chemical investigation of a lipophilic CHCl3 extract of the dried fruits of Barringtonia racemosa resulted in the isolation of two unusual monoacylated polyhydroxy oleanane triterpenoid congeners named racemosols C-D (1-2) along with three known compounds. Their structures were determined by comprehensive spectroscopic analysis coupled with chemical modifications as 2 beta-acetoxy-3 beta, 16 alpha,22 alpha,28-tetrahydroxyolean-12-ene (1) and 22 alpha-(2-methylbutyryl)-3 beta, 15 alpha,16 alpha,21 beta,28-pentahydroxyolean-12-ene (2). Compounds (1-3, 1a, and 2a) were subjected to alpha-glucosidase inhibitory assay and 1 showed the most potent alpha-glucosidase inhibition with an IC50 value of 5.6 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.193

文献信息

• α-Glucosidase inhibitory monoacylated polyhydroxytriterpenoids from the fruits of Barringtonia racemosa
  作者：Mangala Gowri Ponnapalli、Sushma Sukki、S.CH.V. Appa Rao Annam、Madhu Ankireddy、Harini Tirunagari、V. Raju Tuniki、V.V. Pardhasaradhi Bobbili

  DOI：10.1016/j.tetlet.2015.01.193

  日期：2015.3

  Chemical investigation of a lipophilic CHCl3 extract of the dried fruits of Barringtonia racemosa resulted in the isolation of two unusual monoacylated polyhydroxy oleanane triterpenoid congeners named racemosols C-D (1-2) along with three known compounds. Their structures were determined by comprehensive spectroscopic analysis coupled with chemical modifications as 2 beta-acetoxy-3 beta, 16 alpha,22 alpha,28-tetrahydroxyolean-12-ene (1) and 22 alpha-(2-methylbutyryl)-3 beta, 15 alpha,16 alpha,21 beta,28-pentahydroxyolean-12-ene (2). Compounds (1-3, 1a, and 2a) were subjected to alpha-glucosidase inhibitory assay and 1 showed the most potent alpha-glucosidase inhibition with an IC50 value of 5.6 mu M. (C) 2015 Elsevier Ltd. All rights reserved.