Transformation of steviol-16α,17-epoxide by Streptomyces griseus and Cunninghamella bainieri

Shwu Fen Chang, Li Ming Yang, Feng-Lin Hsu, Ju Yin Hsu, Jia Horng Liaw, Shwu Jiuan Lin

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Eight new ent-beyerane metabolites, 5-8, 12, and 14-16, and four new ent-kaurane metabolites, 3, 10, 11, and 13, together with two known metabolites, 4 and 9, were isolated from the microbial transformations of steviol-16α,17-epoxide using Streptomyces griseus ATCC 10137 and Cunninghamella bainieri ATCC 9244. The structures of the metabolites were characterized by IR, HRFABMS, and 1D and 2D NMR data. In addition, a GRE (glucocorticoid response element)-mediated luciferase reporter assay was used to initially screen for the biological activity of the 11 metabolites and stevioside. Steviol (1), steviol-16α,17-epoxide (2), ent-11α,13, 16α,17-tetrahydroxykauran-19-oic acid (3), ent-17-hydroxy-16-ketobeyeran- 19-oic acid (4), ent-9α,13-dihydroxy-16β,17-epoxykauran-19-oic acid (10), ent-9β,17-dihydroxy-16-ketobeyeran-19-oic acid (12), ent-1β,17-dihydroxy-16-ketobeyeran-19-oic acid (14), and stevioside showed significant effects; in particular, stevioside showed almost equal potency as dexamethasone.

Original languageEnglish
Pages (from-to)1450-1455
Number of pages6
JournalJournal of Natural Products
Volume69
Issue number10
DOIs
Publication statusPublished - Oct 2006

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Transformation of steviol-16α,17-epoxide by Streptomyces griseus and Cunninghamella bainieri'. Together they form a unique fingerprint.

  • Cite this