1β,3β,11α-trihydroxyurs-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: 1β,3β,11α-trihydroxyurs-12-en-28-oic acid
• 英文别名: (1S,2R,4aS,6aS,6aS,6bR,8aS,10S,12R,12aS,13R,14bS)-10,12,13-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• 化学式: C₃₀H₄₈O₅
• 分子量: 488.708
• InChiKey: ALPVKKZLECMFMI-JYHPUZRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  熊果酸 以6.23%的产率得到3-氧代-12-烯-28-乌苏酸
  参考文献：
  名称：

  New derivatives of ursolic acid through the biotransformation by Bacillus megaterium CGMCC 1.1741 as inhibitors on nitric oxide production

  摘要：

  Microbial transformation of ursolic acid (1) by Bacillus megaterium CGMCC 1.1741 was investigated and yielded five metabolites identified as 3-oxo-urs-12-en-28-oic acid (2); 1 beta,11 alpha-dihydroxy-3-oxo-urs-12-en-28-oic acid (3); 1 beta-hydroxy-3-oxo-urs-12-en-28, 13-lactoe (4); 1 beta,3 beta, 11 alpha-trihydroxyurs-12-en-28-oic acid (5) and 1 beta,11 alpha-dihydroxy-3-oxo-urs-12-en-28-O-beta-D-glucopyranoside (6). Metabolites 3, 4, 5 and 6 were new natural products. Their nitric oxide (NO) production inhibitory activity was assessed in lipopolysaccharide (LPS) - stimulated RAW 264.7 cells. Compounds 3 and 4 exhibited significant activities with the IC50 values of 1.243 and 1.711 mu M, respectively. A primary structure-activity relationship was also discussed. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.03.076