4-hydroxy-3,4-seco-lup-20(29)-en-3,28-dioic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 4-hydroxy-3,4-seco-lup-20(29)-en-3,28-dioic acid
• 英文别名: 3,4-seco-lup-20(29)-en-4-hydroxy-3,28-oic acid；Mdjrxecevoaeaq-svafspifsa-；(3R,4R,5R,8R,9R,10R,13S,14R,15R)-4-(2-carboxyethyl)-3-(2-hydroxypropan-2-yl)-4,9,10-trimethyl-15-prop-1-en-2-yl-2,3,5,6,7,8,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic acid
• 化学式: C₃₀H₄₈O₅
• 分子量: 488.708
• InChiKey: MDJRXECEVOAEAQ-SVAFSPIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  白桦脂酸 在 Aspergillus terreus SC₁₆₅₁₃, ATCC₁₀₀₂₀ 、 WF₀₄₁ medium 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 反应 168.0h， 以134 mg的产率得到4-hydroxy-3,4-seco-lup-20(29)-en-3,28-dioic acid
  参考文献：
  名称：

  Microbial transformations of betulinic and betulonic acids

  摘要：

  Enzymatic transformation of betulinic acid by growing cells of microorganisms provided several hydroxylated and oxidized products. Bacillus megaterium SC16644 gave 7 beta,15 alpha-dihydroxybetulinic acid, 7 beta,15 alpha-dihydroxybetulonic acid, and a new compound 7 beta,15 alpha,23-trihydroxybetulinic acid [3 beta,7 beta,15 alpha,23-tetrahydroxy-lup-20(29)en-28-oic acid]. Another strain of B. megaterium SC6394 produced 30-oxobetulonic acid, and a mixture of 30-hydroxybetulonic acid and a new compound 7 beta-hydroxy-30-oxobetulonic acid [7 beta-hydroxy-3,30-dioxo-lup-20(29)en-28-oic acid]. Three products were obtained from the biotransformation of betulinic acid by Streptomyces frag-ilis SC16401: 7 beta-hydroxybetulonic acid, and two new compounds 2 alpha,7 beta-dihydroxybetulinic acid [2 alpha,3 beta,7 beta-trihydroxy-lup-20(29)en-28-oic acid] and 2-oxo-7 beta-hydroxy-betulinic acid [2-oxo-3 beta,7 beta-dihydroxy-lup-20(29)en-28-oic acid]. Cunninghamella elegans SC16025 gave 25-hydroxybetulinic acid from betulinic acid. Oxidation of betulinic acid by Aspergillus terreus SC16513 led to two A-ring fission products: 4-hydroxy-3,4-seco-lup-20(29)-en-3,2b-dioic acid and 3,4-seco-lup-20(29), 4(23)-dien-3,28-dioic acid. B. megaterium SC16644 catalyzed transformation of betulonic acid provided 7 beta-hydroxybetulonic acid, 7 beta,15 alpha-dihydroxybetulonic acid, and a new compound 7 beta,15 alpha,30-trihydroxybetulonic acid [3-oxo-7 beta,15 alpha,30-trihydroxy-lup-20(29)en-28-oic acid]. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.04.012

文献信息

• Microbial Transformations of Two Lupane-Type Triterpenes and Anti-Tumor-Promoting Effects of the Transformation Products
  作者：Toshihiro Akihisa、Yoshio Takamine、Kazuo Yoshizumi、Harukuni Tokuda、Yumiko Kimura、Motohiko Ukiya、Toro Nakahara、Toshihiro Yokochi、Eiichiro Ichiishi、Hoyoku Nishino

  DOI：10.1021/np010424m

  日期：2002.3.1

  Microbial transformation of betulin (1), a lupane-type triterpene obtained from the bark: extract of white birch (Betula platyphylla Sukatshev var. japonica), and its chemical oxidation product, betulonic acid (2), by the fungus Chaetomium, longirostre yielded 4,28-dihydroxy-3,4-seco-lup-20(29)-en-3-oic acid (3) and 4-hydroxy-3,4-seco-lup-20(29)-ene-3,28-dioic add (4) from 1, and 4,7beta,17-trihydroxy-3,4-seco-28-norlup-20(29)-en-3-oic acid (5) and 7beta,15alpha-dihydoxy-3-oxolup-20(29)-en-28-oic acid (6) from 2. The four metabolites, 3-6, along with 1 and 2, were evaluated for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells as a primary screening test for inhibitors of tumor promotion. All of the triterpenes tested showed potent inhibitory effects, with the four metabolites 3-6 exhibiting the more potent effects.
• Microbial transformation of pentacyclic triterpenes for anti-inflammatory agents on the HMGB1 stimulated RAW 264.7 cells by Streptomyces olivaceus CICC 23628
  作者：Yuyuan Zhu、Pingping Shen、Jiayi Wang、Xuewa Jiang、Wei Wang、Richa Raj、Haixia Ge、Weiwei Wang、Boyang Yu、Jian Zhang

  DOI：10.1016/j.bmc.2021.116494

  日期：2021.12
• Microbial transformations of betulinic and betulonic acids
  作者：Animesh Goswami、Zhiwei Guo、Thomas P. Tully、Frank A. Rinaldi、Xiaohua Stella Huang、Jacob J. Swidorski、Alicia Regueiro-Ren

  DOI：10.1016/j.molcatb.2015.04.012

  日期：2015.7

  Enzymatic transformation of betulinic acid by growing cells of microorganisms provided several hydroxylated and oxidized products. Bacillus megaterium SC16644 gave 7 beta,15 alpha-dihydroxybetulinic acid, 7 beta,15 alpha-dihydroxybetulonic acid, and a new compound 7 beta,15 alpha,23-trihydroxybetulinic acid [3 beta,7 beta,15 alpha,23-tetrahydroxy-lup-20(29)en-28-oic acid]. Another strain of B. megaterium SC6394 produced 30-oxobetulonic acid, and a mixture of 30-hydroxybetulonic acid and a new compound 7 beta-hydroxy-30-oxobetulonic acid [7 beta-hydroxy-3,30-dioxo-lup-20(29)en-28-oic acid]. Three products were obtained from the biotransformation of betulinic acid by Streptomyces frag-ilis SC16401: 7 beta-hydroxybetulonic acid, and two new compounds 2 alpha,7 beta-dihydroxybetulinic acid [2 alpha,3 beta,7 beta-trihydroxy-lup-20(29)en-28-oic acid] and 2-oxo-7 beta-hydroxy-betulinic acid [2-oxo-3 beta,7 beta-dihydroxy-lup-20(29)en-28-oic acid]. Cunninghamella elegans SC16025 gave 25-hydroxybetulinic acid from betulinic acid. Oxidation of betulinic acid by Aspergillus terreus SC16513 led to two A-ring fission products: 4-hydroxy-3,4-seco-lup-20(29)-en-3,2b-dioic acid and 3,4-seco-lup-20(29), 4(23)-dien-3,28-dioic acid. B. megaterium SC16644 catalyzed transformation of betulonic acid provided 7 beta-hydroxybetulonic acid, 7 beta,15 alpha-dihydroxybetulonic acid, and a new compound 7 beta,15 alpha,30-trihydroxybetulonic acid [3-oxo-7 beta,15 alpha,30-trihydroxy-lup-20(29)en-28-oic acid]. (C) 2015 Elsevier B.V. All rights reserved.