olean-12-ene-3β-o-carboxibenzoate | 1011715-00-6

• 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
• 英文名称: olean-12-ene-3β-o-carboxibenzoate
• 英文别名: β-amyrin 3-O-(2-carboxybenzoate)；β-amyrin o-carboxibenzoate；2-[[(3S,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxycarbonyl]benzoic acid
• CAS: 1011715-00-6
• 化学式: C₃₈H₅₄O₄
• 分子量: 574.844
• InChiKey: ITOOCVSAABHXQM-MOBOHLQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯酐 、 α-香树精 、 β-香树精 在 吡啶 作用下， 以 乙醚 为溶剂， 反应 8.0h， 生成 2-(4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yloxy)carbonylbenzoic acid 、 olean-12-ene-3β-o-carboxibenzoate
  参考文献：
  名称：

  Amyrin esters induce cell death by apoptosis in HL-60 leukemia cells

  摘要：

  Four derivatives of an alpha,beta-amyrin mixture were synthesized by acylation with appropriate anhydrides. The structures of the compounds were confirmed by means of IR and H-1 and C-13 NMR. The compounds were screened for cytotoxic activity using four human tumor cell lines (HL-60, MDAMB-435, SF-295 and HCT-8) and normal peripheral blood mononuclear cells (PBMC). 3-O-Carboxymaleinate of alpha,beta-amyrin (3a/3b) were found to be the only active compounds of the series (high cytotoxicity), showing IC50 values ranging from 1.8 to 3 mu M. In PBMC, 3a/3b were not toxic, suggesting selectivity for tumor cells. To better understand the mechanism of action involved in the cytotoxicity of 3a/3b, HL-60 cells treated with 3a/3b were examined for morphological changes, DNA fragmentation, cell cycle perturbation, externalization of phosphatidylserine and activation of caspases 3/7, with doxorubicin serving as the positive control. The results indicate that the cytotoxicity of 3a/3b involves the induction of cell death by apoptosis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.016