3α,24-dihydroxyolean-12-en-27-oic acid | 890663-26-0

• 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: 3α,24-dihydroxyolean-12-en-27-oic acid
• 英文别名: 3a,24-Dihydroxyolean-12-en-27-oic acid；(4aR,6aR,6aR,6bR,8aR,9S,10R,12aR,14bR)-10-hydroxy-9-(hydroxymethyl)-2,2,4a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-6a-carboxylic acid
• CAS: 890663-26-0
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: HQGWITLOHQUPBL-VSGKQSHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3α,24-dihydroxyolean-12-en-27-oic acid 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 生成
  参考文献：
  名称：

  Protein tyrosine phosphatase 1B inhibitory activity of triterpenes isolated from Astilbe koreana

  摘要：

  Bioassay-guided fractionation of a MeOH extract of the rhizomes of Astilbe koreana (Saxifragaceae), using an in vitro protein tyrosine phosphatase 1B (PTP1B) inhibitory assay, resulted in the isolation of a new triterpene, 3 alpha,24-dihydroxyolean-12-en-27-oic acid (4), along with four triterpenes, 3-oxoolean-12-en-27-oic acid (1), 3 beta-hydroxyolean-12-en-27-oic acid (beta-peltoboy-kinolic acid; 2), 3 beta-hydroxyurs-12-en-27-oic acid (3), and 3 beta,6 beta-dihydroxyolean-12-en-27-oic acid (astilbic acid; 5). Compounds 1-5 inhibited PTP1B with IC50 values of 6.8 +/- 0.5, 5.2 +/- 0.5, 4.9 +/- 0.4, 11.7 +/- 0.9, and 12.8 +/- 1.1 mu M, respectively. Our results indicate that 3-hydroxyl group and a carboxyl group in this type of triterpenes may be required for the activity, while addition of one more hydroxyl group at C-6 or C-24 may be responsible for a loss of activity. Thus, compounds 2 and 3 which possess only one hydroxyl group at C-3 and a carboxyl group at C-27 could be potential PTP1B inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.036