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

Fingerprint

Cunninghamella
steviol
Streptomyces griseus
Epoxy Compounds
Metabolites
epoxides
stevioside
metabolites
Acids
acids
Kaurane Diterpenes
Response Elements
Luciferases
Dexamethasone
Glucocorticoids
response elements
luciferase
dexamethasone
glucocorticoids
Bioactivity

ASJC Scopus subject areas

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

Cite this

Transformation of steviol-16α,17-epoxide by Streptomyces griseus and Cunninghamella bainieri. / Chang, Shwu Fen; Yang, Li Ming; Hsu, Feng-Lin; Hsu, Ju Yin; Liaw, Jia Horng; Lin, Shwu Jiuan.

In: Journal of Natural Products, Vol. 69, No. 10, 10.2006, p. 1450-1455.

Research output: Contribution to journalArticle

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