14-deoxy-12R-hydroxyandrographolide | 219721-30-9

• 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: 14-deoxy-12R-hydroxyandrographolide
• 英文别名: 4-[(1R)-2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]-2H-furan-5-one
• CAS: 219721-30-9
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: KHQNSSJNIXVKMK-UQZPWQSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  14-去氧-11,12-二去氢穿心莲内酯 在 Cunninghamella blakesleana (AS 3.970) 作用下， 以 乙醇 为溶剂， 以6.25%的产率得到3-((E)-2-((1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyloctahydro-1H-spiro[naphthalene-2,2′-oxiran]-1-yl)vinyl)furan-2(5H)-one
  参考文献：
  名称：

  Microbial transformation of 14-deoxy-11, 12-didehydroandrographolide and 14-deoxyandrographolide and inhibitory effects on nitric oxide production of the transformation products

  摘要：

  Microbial transformations of 14-deoxy-11, 12-didehyclroandrographolide (a) and 14-deoxyandrographolide (b) were performed by Cunninghamella blakesleana (AS 3.970), respectively. Sixteen metabolites were obtained and their structures were elucidated by spectroscopic data analyses. Among these metabolites, 3 alpha, 12S, 19-trihydroxy-8(17), 9(11)-ent-labdadien-16, 15-olide (a7), 3-oxo-8 alpha, 17 beta-epoxy-14-deoxyandrographolide (b2). 3 alpha, 17. 19-trihydroxy-8, 13-ent-labdadien-16, 15-olide (b6), and 9 beta-hydroxy-14-deoxyandrographolide (b9) are new compounds. The configuration of C-12 in metabolite a7 was determined as S by GIAO method. The proposed metabolic pathways of 14-deoxy-11, 12-didehydroandrographolide and 14-deoxyandrographolide by C blakesleana were drawn. The inhibitory effects of these compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated and their preliminary structure-activity relationships (SAR) were discussed. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.06.012

文献信息

• Microbial transformation of 14-deoxy-11, 12-didehydroandrographolide and 14-deoxyandrographolide and inhibitory effects on nitric oxide production of the transformation products
  作者：Li-Xia Chen、Yu-Lei Zhuang、Lan Shen、En-Long Ma、Hua-Jie Zhu、Feng Zhao、Feng Qiu

  DOI：10.1016/j.molcatb.2011.06.012

  日期：2011.11

  Microbial transformations of 14-deoxy-11, 12-didehyclroandrographolide (a) and 14-deoxyandrographolide (b) were performed by Cunninghamella blakesleana (AS 3.970), respectively. Sixteen metabolites were obtained and their structures were elucidated by spectroscopic data analyses. Among these metabolites, 3 alpha, 12S, 19-trihydroxy-8(17), 9(11)-ent-labdadien-16, 15-olide (a7), 3-oxo-8 alpha, 17 beta-epoxy-14-deoxyandrographolide (b2). 3 alpha, 17. 19-trihydroxy-8, 13-ent-labdadien-16, 15-olide (b6), and 9 beta-hydroxy-14-deoxyandrographolide (b9) are new compounds. The configuration of C-12 in metabolite a7 was determined as S by GIAO method. The proposed metabolic pathways of 14-deoxy-11, 12-didehydroandrographolide and 14-deoxyandrographolide by C blakesleana were drawn. The inhibitory effects of these compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated and their preliminary structure-activity relationships (SAR) were discussed. (C) 2011 Elsevier B.V. All rights reserved.