3β,7β,15α-trihydroxy-lup-20(29)en-28-oic acid | 302925-21-9

• 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,7β,15α-trihydroxy-lup-20(29)en-28-oic acid
• 英文别名: 7β,15α-dihydroxybetulinicacid；(1R,3aS,5S,5aR,5bR,6S,7aR,9S,11aS,11bR,13aR,13bR)-5,6,9-trihydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• CAS: 302925-21-9
• 化学式: C₃₀H₄₈O₅
• 分子量: 488.708
• InChiKey: ONXWPJASQLQPHW-RFMJYCFVSA-N

物化性质

• 沸点：
  613.1±55.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  2
• 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：

  白桦脂酸 在 Bacillus megaterium (SC₁₆₆₄₄, ATCC₁₄₅₈₁) 作用下， 以 二甲基亚砜 为溶剂， 反应 336.0h， 生成 3β,7β,15α-trihydroxy-lup-20(29)en-28-oic acid
  参考文献：
  名称：

  通过 C?H 氧化改善物理特性：化学和酶法

  摘要：

  物理化学特性是候选药物成功的关键因素。尽管存在许多改善小杂环型先导物物理化学性质的策略，但由于缺乏官能团，复杂的烃骨架衍生化更具挑战性。各种C已经在桦木脑骨架上探索了 H 氧化方法，以提高这种非常具有生物活性但水溶性差的天然产物的溶解度。利用分子的先天反应性以及核心上存在的少数分子手柄，允许在五环结构的不同位置进行氧化。酶促氧化为化学方法提供了几种正交氧化。溶解度测量显示许多合成化合物的增强。

  DOI：

  10.1002/anie.201407016

文献信息

• Biotransformation of betulinic acid by Circinella muscae and Cunninghamella echinulata to discover anti-inflammatory derivatives
  作者：Chen Chen、Kainan Song、Yongzhen Zhang、Chengjiao Chu、Boyi Fan、Yan Song、Huilian Huang、Guangtong Chen

  DOI：10.1016/j.phytochem.2020.112608

  日期：2021.2

  Circinella muscae CGMCC 3.2695 and Cunninghamella echinulata CGMCC 3.970, yielded six previously undescribed hydroxylated metabolites and four known compounds. C. muscae could catalyze the regioselecitve hydroxylation and carbonylation at C-3, C-7, C-15 and C-21 to yield seven products. C. echinulata could catalyze the C-1, C-7 and C-26 regioselecitve hydroxylation and acetylation to yield five metabolites

  桦木酸的生物转化用圆环藻 CGMCC 3.2695 和 Cunninghamella echinulata CGMCC 3.970 进行，产生了六种以前未描述的羟基化代谢物和四种已知化合物。C. muscae 可以催化 C-3、C-7、C-15 和 C-21 的区域选择性羟基化和羰基化，产生七种产物。C. echinulata 可以催化 C-1、C-7 和 C-26 区域选择性羟基化和乙酰化产生五种代谢物。代谢物的结构是基于广泛的 NMR 和 HR-ESI-MS 数据分析建立的。此外，大多数代谢物对 RAW264.7 细胞中脂多糖诱导的 NO 产生表现出明显的抑制活性。
• 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.