Microbial transformation of isosteviol lactone and evaluation of the transformation products on androgen response element

Bo Hon Chou, Li Ming Yang, Shwu Fen Chang, Feng-Lin Hsu, Chia Hsin Lo, Jia Horng Liaw, Pan Chun Liu, Shwu Jiuan Lin

研究成果: 雜誌貢獻文章

13 引文 (Scopus)

摘要

Two filamentous fungi, Cunninghamella bainieri ATCC 9244 and Aspergillus niger BCRC 32720, were used to investigate the biotransformation of isosteviol lactone (4α-carboxy-13α-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.

原文英語
頁(從 - 到)602-607
頁數6
期刊Journal of Natural Products
71
發行號4
DOIs
出版狀態已發佈 - 四月 2008

指紋

Aspergillus niger
response elements
Response Elements
Metabolites
androgens
lactones
Androgens
Cunninghamella
Hydroxylation
Acids
Methylation
Aspergillus
acids
Lactones
Biotransformation
Isomerization
Fungi
Luciferases
Reporter Genes
metabolites

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

引用此文

Microbial transformation of isosteviol lactone and evaluation of the transformation products on androgen response element. / Chou, Bo Hon; Yang, Li Ming; Chang, Shwu Fen; Hsu, Feng-Lin; Lo, Chia Hsin; Liaw, Jia Horng; Liu, Pan Chun; Lin, Shwu Jiuan.

於: Journal of Natural Products, 卷 71, 編號 4, 04.2008, p. 602-607.

研究成果: 雜誌貢獻文章

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AU - Liaw, Jia Horng

AU - Liu, Pan Chun

AU - Lin, Shwu Jiuan

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