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

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)602-607
Number of pages6
JournalJournal of Natural Products
Volume71
Issue number4
DOIs
Publication statusPublished - Apr 2008

Fingerprint

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

Cite this

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.

In: Journal of Natural Products, Vol. 71, No. 4, 04.2008, p. 602-607.

Research output: Contribution to journalArticle

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AU - Liaw, Jia Horng

AU - Liu, Pan Chun

AU - Lin, Shwu Jiuan

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