3-oxo-16α-hydroxy-olean-12-en-28-oic acid 28-O-β-D-glucopyranoside | 1260114-56-4

• 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: 3-oxo-16α-hydroxy-olean-12-en-28-oic acid 28-O-β-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylate
• CAS: 1260114-56-4
• 化学式: C₃₆H₅₆O₉
• 分子量: 632.835
• InChiKey: VXWPPCALNFTIKB-MNPFCYDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  45
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  刺囊酸 在 Nocardia corallina CGMCC₄₁₀₃₇ 作用下， 以 乙醇 、 水 为溶剂， 反应 168.0h， 以22.8%的产率得到3-oxo-16α-hydroxy-olean-12-en-28β-oic acid
  参考文献：
  名称：

  Microbial oxidation and glucosidation of echinocystic acid by Nocardia corallina

  摘要：

  Echinocystic acid (3 beta,16 alpha-dihydroxy-olean-12-en-28-oic acid 1) is a complex compound with many bioactivities. Microbial transformation of echinocystic acid (1) by Nocardia corallina CGMCC4.1037 has been studied. Incubation of echinocystic acid with N. corallina CGMCC4.1037 afforded three metabolites: 3-oxo-16 alpha-hydroxy-olean-12-en-28-oic acid (2), 3 beta,16 alpha-dihydroxy-olean-12-en-28-oic acid 28-O-beta-D-glucopyranoside (3), and 3-oxo-16 alpha-hydroxy-olean-12-en-28-oic acid 28-O-beta-D-glucopyranoside (4). Product (4) was a new product. Their structure elucidation was mainly based on the HRMS and NMR data. The possible mechanism of the regio-selective oxidation of the 3-OH and a probable sequence of these transformations were also discussed. This is the first report on the microbial transformation of echinocystic acid (1). This method may open a new route to the future modification of echinocystic acid (1). (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.05.012