4α-carboxy-1α,7β,13α-trihydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone | 1012876-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4α-carboxy-1α,7β,13α-trihydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone
• 英文别名: (1S,2S,4S,5R,8S,9S,10R,13S)-2,8-dihydroxy-5,9,13-trimethyl-15-oxo-14-oxatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylic acid
• CAS: 1012876-92-4
• 化学式: C₂₀H₃₀O₆
• 分子量: 366.455
• InChiKey: VASJJOZORMHXKA-PZEXLGDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  异甜菊醇内酯 在 Aspergillus niger BCRC 32720 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 以4 mg的产率得到4α-carboxy-7β,13α-dihydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone
  参考文献：
  名称：

  Microbial Transformation of Isosteviol Lactone and Evaluation of the Transformation Products on Androgen Response Element

  摘要：

  Two filamentous fungi, Cunninghamella bainieri ATCC 9244 and Aspergillus niger BCRC 32720, were used to investigate the biotransformation of isosteviol lactone (4 alpha-carboxy-13 alpha-hydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone) (2), which was derived by reacting isosteviol (ent-16-oxobeyeran-19-oic acid) (1) with m-chloroperbenzoic acid. Incubation of 2 with C. bainieri afforded metabolites 3-6, which involved isomerization, hydroxylation, and ring cleavage reactions followed by oxidation and selective O-methylation. Incubation of 2 with A. niger afforded mono-, di-, and trihydroxylated metabolites 3, 4, and 7-12. The structures of 3-12 were elucidated on the basis of spectroscopic analyses, and structures 3, 4, and 6 were confirmed by X-ray crystallographic studies. Compounds 2-6, 8-10, and 12 were assayed as androgen agonists using an ARE (androgen response element)-mediated luciferase reporter gene assay. Compounds 3, 6, and 10 were significantly active, with 6 showing more activity than testosterone.

  DOI：

  10.1021/np070585b