3β,21β-dihydroxy-urs-11-ene-28-oic acid-13-lactone | 1396810-51-7

• 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: 3β,21β-dihydroxy-urs-11-ene-28-oic acid-13-lactone
• 英文别名: (1R,4S,5R,8R,10S,13S,14R,17S,18R,19S,20S,21S)-10,21-dihydroxy-4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-23-one
• CAS: 1396810-51-7
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: DRNCNHZNEWFZFF-FDQJDZNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  熊果酸 在 Syncephalastrum racemosum (Cohn) Schroter AS 3.264 作用下， 以 丙酮 为溶剂， 反应 192.0h， 以7 mg的产率得到3β,21β-dihydroxy-urs-11-ene-28-oic acid-13-lactone
  参考文献：
  名称：

  Microbial transformation of ursolic acid by Syncephalastrum racemosum (Cohn) Schroter AS 3.264

  摘要：

  Biotransformation of ursolic acid by the filamentous fungus Syncephalastrum racemosum (Cohn) Schroter AS 3.264 yielded five metabolites. Their structures were identified as 3 beta,21 beta-dihydroxy-urs-11-en-28-oic acid-13-lactone, 3 beta,7 beta,21 beta-trihydroxy-urs-11-en-28-oic acid-13-lactone, 1 beta,3 beta-dihydroxy-urs-12-en-21-one-28-oic acid, 1 beta,3 beta,21 beta-trihydroxy-urs-12-en-28-oic acid and 11,26-epoxy-3 beta,21 beta-dihydroxy-urs-12-en-28-oic acid based on NMR and MS spectroscopic analyses. The condensation reactions to form 28-oic acid-13-lactone ring and 11,26-epoxy ring are not frequently seen for the biotransformation of triterpenoids. One compound showed moderate inhibitory activity against protein tyrosine phosphatase 1B (PTP1B). (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.06.020