4α-carboxy-1α,7β,11α,13α-tetrahydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone | 1012877-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 4α-carboxy-1α,7β,11α,13α-tetrahydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone
• 英文别名: (1S,2S,4S,5R,8S,9R,10R,11S,13R)-2,8,11-trihydroxy-5,9,13-trimethyl-15-oxo-14-oxatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylic acid
• CAS: 1012877-00-7
• 化学式: C₂₀H₃₀O₇
• 分子量: 382.454
• InChiKey: PJDAOTFHVKYNJA-XWGHIXMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 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：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  异甜菊醇内酯 在 Absidia pseudocylindrospora ATCC 24169 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 以80 mg的产率得到4α-carboxy-1α,7β,11α,13α-tetrahydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone
  参考文献：
  名称：

  Fungal transformation of isosteviol lactone and its biological evaluation for inhibiting the AP-1 transcription factor

  摘要：

  A number of hydroxylated diterpenoids were obtained from the microbial transformation of isosteviol lactone (4 alpha-carboxy-13 alpha-hydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone) (2) with Mucor recurvatus MR 36, Aspergillus niger BCRC 31130, and Absidia pseudocylindrospora ATCC 24169. Incubation of 2 with M. recurvatus and Asp. niger led to isolation of seven known compounds (1 and 3-8). Incubation of 2 with Abs. pseudocylindrospora produced 5 and six previously unreported compounds (9-14). The structures of these isolated compounds were deduced by high-field NMR techniques (H-1, C-13, DEPT, COSY, NOESY, HSQC, and HMBC), and those of 9 and 11 were further confirmed by X-ray crystallographic analyses. Subsequently, the inhibitory effects on activator protein-1 (AP-1) activation in lipo-polysaccharide-stimulated RAW 264.7 macrophages of all of these compounds were evaluated. Compounds 2-5, 8, 9, 11, and 12 exhibited significant inhibitory activity, while 3 was more potent than the reference compound of dexamethasone. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.03.015

文献信息

• Microbial Transformation of Isosteviol Lactone and Evaluation of the Transformation Products on Androgen Response Element
  作者：Bo-Hon Chou、Li-Ming Yang、Shwu-Fen Chang、Feng-Lin Hsu、Chia-Hsin Lo、Jia-Horng Liaw、Pan-Chun Liu、Shwu-Jiuan Lin

  DOI：10.1021/np070585b

  日期：2008.4.1

  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.