(2α,3β) 2,3-dihydroxy-12-bromo-olean-28-oic acid 28,13-lactone | 142179-91-7

• 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: (2α,3β) 2,3-dihydroxy-12-bromo-olean-28-oic acid 28,13-lactone
• 英文别名: 12α-bromo-2α,3β-dihydroxyolean-28,13β-olide；12α-bromo-2α,3β-dihydroxyoleanan-28,13β-olide；(1S,4S,5R,8R,10R,11R,13R,14R,16S,17S,18R)-16-bromo-10,11-dihydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-23-one
• CAS: 142179-91-7
• 化学式: C₃₀H₄₇BrO₄
• 分子量: 551.605
• InChiKey: UZFARBMFBLXDIJ-BIJMGBHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  35.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2α,3β) 2,3-dihydroxy-12-bromo-olean-28-oic acid 28,13-lactone 在 吡啶 、 过氧乙酸 、 乙醇 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 2α,3β-diacetoxy-11α,12α-epoxyolean-28,13β-olide
  参考文献：
  名称：

  Biotransformation of oleanolic and maslinic acids by Rhizomucor miehei

  摘要：

  Microbial transformation of oleanolic acid by Rhizomucor miehei produced three metabolites. A known compound, a 30-hydroxyl derivative (queretaroic acid), and two 7 beta,30- and 1 beta,30-dihydroxylated metabolites, respectively. The action of the same fungus (R. miehei) on maslinic acid produced an olean-11-en-28,13 beta-olide derivative, a metabolite hydroxylated at C-30, an 11-oxo derivative, and two metabolites with an 11 alpha,12 alpha-epoxy group, hydroxylated or not at C-30. Their structures were elucidated by extensive analyses of their spectroscopic data, and also by chemical correlations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.05.011
• 作为产物：
  描述：

  山楂酸 在 溴 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 0.17h， 以72%的产率得到(2α,3β) 2,3-dihydroxy-12-bromo-olean-28-oic acid 28,13-lactone
  参考文献：
  名称：

  The chemical and biological potential of C ring modified triterpenoids

  摘要：

  A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.025

文献信息

• The chemical and biological potential of C ring modified triterpenoids
  作者：Bianka Siewert、Jana Wiemann、Alexander Köwitsch、René Csuk

  DOI：10.1016/j.ejmech.2013.11.025

  日期：2014.1

  A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780). (C) 2013 Elsevier Masson SAS. All rights reserved.
• Biotransformation of oleanolic and maslinic acids by Rhizomucor miehei
  作者：Antonio Martinez、Francisco Rivas、Alberto Perojil、Andres Parra、Andres Garcia-Granados、Antonia Fernandez-Vivas

  DOI：10.1016/j.phytochem.2013.05.011

  日期：2013.10

  Microbial transformation of oleanolic acid by Rhizomucor miehei produced three metabolites. A known compound, a 30-hydroxyl derivative (queretaroic acid), and two 7 beta,30- and 1 beta,30-dihydroxylated metabolites, respectively. The action of the same fungus (R. miehei) on maslinic acid produced an olean-11-en-28,13 beta-olide derivative, a metabolite hydroxylated at C-30, an 11-oxo derivative, and two metabolites with an 11 alpha,12 alpha-epoxy group, hydroxylated or not at C-30. Their structures were elucidated by extensive analyses of their spectroscopic data, and also by chemical correlations. (C) 2013 Elsevier Ltd. All rights reserved.
• Biotransformation of oleanolic and maslinic methyl esters by Rhizomucor miehei CECT 2749
  作者：Antonio Martinez、Alberto Perojil、Francisco Rivas、Andres Parra、Andres Garcia-Granados、Antonia Fernandez-Vivas

  DOI：10.1016/j.phytochem.2015.07.020

  日期：2015.9

  The pentacyclic triterpenoids methyl oleanolate, methyl maslinate, methyl 3 beta-hydroxyolean-9(11),12-dien-28-oate, and methyl 2 alpha,3 beta-dihydroxy-12 beta,13 beta-epoxyolean-28-oate were biotransformed by Rhizomucor miehei CECT 2749. Microbial transformation of methyl oleanolate produced only a 7 beta,30-di-hydroxylated metabolite with a conjugated 9(11),12-diene system in the C ring. Biotransformation of the substrate with this 9(11),12-diene system gave the same 7 beta,30-dihydroxylated compound together with a 7 beta,15 alpha,30-trihydroxyl derivative. The action of this fungus (R. miehei) on methyl maslinate was more varied, isolating metabolites with a 30-hydroxyl group, a 9(11),12-diene system, an 11-oxo group, or an 12-oxo group. Microbial transformation of the substrate with a 12 beta,13 beta-epoxy function resulted in the isolation of two metabolites with 12-oxo and 28,13 beta-olide groups, hydroxylated or not at C-7 beta, together with a 30-hydroxy-12-oxo derivative. The structures of these derivatives were deduced by extensive and rigorous spectroscopic studies. (C) 2015 Elsevier Ltd. All rights reserved.