7β,15α-dihydroxybetulonic acid

• 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: 7β,15α-dihydroxybetulonic acid
• 英文别名: 7β,15α-dihydroxy-3-oxolup-20(29)-en-28-oic acid；3-oxo-7β,15α-dihydroxy-lup-20(29)-en-28-oic acid；Vrbzqalcwvckkk-dewkcetosa-；(1R,3aS,5S,5aR,5bR,6S,7aR,11aR,11bR,13aR,13bR)-5,6-dihydroxy-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
• 化学式: C₃₀H₄₆O₅
• 分子量: 486.692
• InChiKey: VRBZQALCWVCKKK-DEWKCETOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7β,15α-dihydroxybetulonic acid 在 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.5h， 生成 (1R,3aS,4aS,4a1R,7aS,7a1R,8aR,12aS,12bR,14aR,14bR)-benzyl 10-(4-(methoxycarbonyl)phenyl)-4a1,6,6,7a1,9,9,12a-heptamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,4a,4a1,7a,7a1,8,8a,9,12,12a,12b,13,14,14a,14b-octadecahydro-1H-cyclopenta[1,2]chryseno[4,5-def][1,3]dioxepine-3a-carboxylate
  参考文献：
  名称：

  [EN] BETULINIC ACID DERIVATIVES WITH HIV MATURATION INHIBITORY ACTIVITY
  [FR] DÉRIVÉS D'ACIDE BÉTULINIQUE PRÉSENTANT UNE ACTIVITÉ INHIBITRICE DE MATURATION DU VIH

  摘要：

  具有药物和生物活性的化合物、其药物组合物及其用途被详细说明。特别是，提供了具有独特抗病毒活性的白桦酸衍生物，作为HIV成熟抑制剂，由公式I、II和III所示的化合物代表：[请在此处插入化学结构]; [请在此处插入化学结构]; [请在此处插入化学结构]; 这些化合物用于治疗HIV和艾滋病。

  公开号：

  WO2015195776A1
• 作为产物：
  描述：

  白桦脂醇 在 jones' reagent 、 Chaetomium longirostre IFO 9873 作用下， 以 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 1.5h， 生成 7β,15α-dihydroxybetulonic acid
  参考文献：
  名称：

  Microbial Transformations of Two Lupane-Type Triterpenes and Anti-Tumor-Promoting Effects of the Transformation Products

  摘要：

  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.

  DOI：

  10.1021/np010424m

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.
• BETULINIC ACID DERIVATIVES WITH HIV MATURATION INHIBITORY ACTIVITY
  申请人：ViiV Healthcare UK (No.5) Limited

  公开号：US20170204133A1

  公开（公告）日：2017-07-20

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, betulinic acid derivaties that possess unique antiviral activity are provided as HIV maturation inhibitors, as represented by compounds of Formulas I, II and III: These compounds are useful for the treatment of HIV and AIDS.
• US9920090B2
  申请人：——

  公开号：US9920090B2

  公开（公告）日：2018-03-20
• [EN] BETULINIC ACID DERIVATIVES WITH HIV MATURATION INHIBITORY ACTIVITY<br/>[FR] DÉRIVÉS D'ACIDE BÉTULINIQUE PRÉSENTANT UNE ACTIVITÉ INHIBITRICE DE MATURATION DU VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015195776A1

  公开（公告）日：2015-12-23

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, betulinic acid derivaties that possess unique antiviral activity are provided as HIV maturation inhibitors, as represented by compounds of Formulas I, II and III: [Please insert chemical structure here]; [Please insert chemical structure here]; [Please insert chemical structure here]; These compounds are useful for the treatment of HIV and AIDS.

  具有药物和生物活性的化合物、其药物组合物及其用途被详细说明。特别是，提供了具有独特抗病毒活性的白桦酸衍生物，作为HIV成熟抑制剂，由公式I、II和III所示的化合物代表：[请在此处插入化学结构]; [请在此处插入化学结构]; [请在此处插入化学结构]; 这些化合物用于治疗HIV和艾滋病。