3β,24-dihydroxy-olean-12-ene-28,29-dioic acid | 96284-36-5

• 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,24-dihydroxy-olean-12-ene-28,29-dioic acid
• 英文别名: Olean-12-ene-28,29-dioic acid, 3,23-dihydroxy-, (3beta,4beta,20alpha)；(2R,4aR,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylic acid
• CAS: 96284-36-5
• 化学式: C₃₀H₄₆O₆
• 分子量: 502.692
• InChiKey: CLXOLTFMHAXJST-HKBJSXRUSA-N

物化性质

• 沸点：
  656.8±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  齐墩果酸 在 Streptomyces griseus ATCC 13273 作用下， 反应 144.0h， 以98.6 mg的产率得到三对节萜酸
  参考文献：
  名称：

  New approaches to the structural modification of olean-type pentacylic triterpenes via microbial oxidation and glycosylation

  摘要：

  Microbial transformation of 4 olean-type pentacyclic triterpenes (OPTs), 3-oxo oleanolic acid (1), 3-acetyl oleanolic acid (2), oleanolic acid (3), and esculentoside A (4) was studied. After the screening of 12 strains of microbes, preparative biotransformation by two strains of Streptomyces griseus ATCC 13273 and Aspergillus ochraceus CICC 40330 resulted in the isolation of 10 metabolites. The microbial catalyzed high efficient regio-selective methyl oxidation and glycosylation were discovered, which could be provided as an alternative method to expand the structural diversity of OPTs. All the structures of the metabolites were elucidated unambiguously by ESI-MS, H-1 NMR, C-13 NMR, and 2D-NMR spectroscopy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.055

文献信息

• New approaches to the structural modification of olean-type pentacylic triterpenes via microbial oxidation and glycosylation
  作者：Yu-Yao Zhu、Li-Wu Qian、Jian Zhang、Ji-Hua Liu、Bo-Yang Yu

  DOI：10.1016/j.tet.2011.04.055

  日期：2011.6

  Microbial transformation of 4 olean-type pentacyclic triterpenes (OPTs), 3-oxo oleanolic acid (1), 3-acetyl oleanolic acid (2), oleanolic acid (3), and esculentoside A (4) was studied. After the screening of 12 strains of microbes, preparative biotransformation by two strains of Streptomyces griseus ATCC 13273 and Aspergillus ochraceus CICC 40330 resulted in the isolation of 10 metabolites. The microbial catalyzed high efficient regio-selective methyl oxidation and glycosylation were discovered, which could be provided as an alternative method to expand the structural diversity of OPTs. All the structures of the metabolites were elucidated unambiguously by ESI-MS, H-1 NMR, C-13 NMR, and 2D-NMR spectroscopy. (C) 2011 Elsevier Ltd. All rights reserved.