23-trans-p-coumaroyloxy-2α,3α-dihydroxyolean-12-en-28-oic acid

• 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: 23-trans-p-coumaroyloxy-2α,3α-dihydroxyolean-12-en-28-oic acid
• 英文别名: (4aS,6aR,6aS,6bR,8aR,9R,10S,11R,12aR,14bR)-10,11-dihydroxy-9-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• 化学式: C₃₉H₅₄O₇
• 分子量: 634.854
• InChiKey: FWUYLMWSIUOLQP-MZRAHRTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  23-trans-p-coumaroyloxy-2α,3α-dihydroxyolean-12-en-28-oic acid 在 甲醇 、 potassium hydroxide 作用下， 反应 3.0h， 以1.5 mg的产率得到2α,3α,23-trihydroxyolean-12-en-28-oic acid
  参考文献：
  名称：

  Bioactivity-guided isolation of cytotoxic triterpenoids from the trunk of Berberis koreana

  摘要：

  A bioassay-guided fractionation and chemical investigation of the trunk of Berberis koreana resulted in the isolation and characterization of two new triterpenoids, 23-trans-p-coumaroyloxy-2 alpha,3 alpha-dihydroxyolean-12-en-28-oic acid ( 1), and 23-cis-p-coumaroyloxy-2 alpha,3 alpha-dihydroxyolean-12-en-28-oic acid ( 2), along with seven known triterpenoids (3-9). The structures of the new compounds were determined on the basis of spectroscopic analyses including 2D NMR. The cytotoxic activities of the triterpenes (19) were evaluated by determining their inhibitory effects on human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) using the SRB assay. Compounds 5 and 6 showed potent cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines (IC50 ( 5): 4.37, 7.04, 9.72, and 5.83 mu M, and IC50 (6): 5.57, 7.84, 13.29, and 5.61 mu M, respectively). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.156

文献信息

• Bioactivity-guided isolation of cytotoxic triterpenoids from the trunk of Berberis koreana
  作者：Ki Hyun Kim、Sang Un Choi、Kang Ro Lee

  DOI：10.1016/j.bmcl.2010.01.156

  日期：2010.3

  A bioassay-guided fractionation and chemical investigation of the trunk of Berberis koreana resulted in the isolation and characterization of two new triterpenoids, 23-trans-p-coumaroyloxy-2 alpha,3 alpha-dihydroxyolean-12-en-28-oic acid ( 1), and 23-cis-p-coumaroyloxy-2 alpha,3 alpha-dihydroxyolean-12-en-28-oic acid ( 2), along with seven known triterpenoids (3-9). The structures of the new compounds were determined on the basis of spectroscopic analyses including 2D NMR. The cytotoxic activities of the triterpenes (19) were evaluated by determining their inhibitory effects on human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) using the SRB assay. Compounds 5 and 6 showed potent cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines (IC50 ( 5): 4.37, 7.04, 9.72, and 5.83 mu M, and IC50 (6): 5.57, 7.84, 13.29, and 5.61 mu M, respectively). (C) 2010 Elsevier Ltd. All rights reserved.