Microbial transformation of isosteviol and bioactivities against the glucocorticoid/androgen response elements

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Abstract

Preparative-scale fermentation of isosteviol (ent-16-oxobeyeran-19-oic acid) (1) with Mucor recurvatus MR 36, Absidia pseudocylindrospora ATCC 24169, and Aspergillus niger BCRC 32720 afforded nine known metabolites (2, 3, 5-10, and 14) and nine new metabolites (4, 11-13, and 15-19). The reactions involved stereoselective introduction of OH groups at positions C-1, -6, -7, -9, -11, -12, -15, and -17 as well as further ketonization at the C-1 and C-7 positions. The structures of the metabolites were established on the basis of 1D and 2D NMR and IR supported by HRFABMS. GRE (glucocorticoid response element)- and ARE (androgen response element)-mediated luciferase reporter gene assays were used to screen for the biological activities of 1 and its metabolites. Compounds 7, 13, 16, and 18 showed significantly enhanced GRE-mediated luciferase activity, but at levels less than that induced by either methylprednisolone or dexamethasone. On the other hand, compounds 3, 4, 12, 13, 14, and 18 showed significant effects on ARE-mediated luciferase activity; in particular, 3, 12, 14, and 18 were more active than testosterone.

Original languageEnglish
Pages (from-to)87-92
Number of pages6
JournalJournal of Natural Products
Volume71
Issue number1
DOIs
Publication statusPublished - Jan 2008

Fingerprint

response elements
Response Elements
Metabolites
glucocorticoids
androgens
Bioactivity
Glucocorticoids
Androgens
luciferase
Luciferases
metabolites
Absidia
Mucor
Aspergillus niger
Aspergillus
Methylprednisolone
dexamethasone
Reporter Genes
reporter genes
Fermentation

ASJC Scopus subject areas

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

Cite this

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title = "Microbial transformation of isosteviol and bioactivities against the glucocorticoid/androgen response elements",
abstract = "Preparative-scale fermentation of isosteviol (ent-16-oxobeyeran-19-oic acid) (1) with Mucor recurvatus MR 36, Absidia pseudocylindrospora ATCC 24169, and Aspergillus niger BCRC 32720 afforded nine known metabolites (2, 3, 5-10, and 14) and nine new metabolites (4, 11-13, and 15-19). The reactions involved stereoselective introduction of OH groups at positions C-1, -6, -7, -9, -11, -12, -15, and -17 as well as further ketonization at the C-1 and C-7 positions. The structures of the metabolites were established on the basis of 1D and 2D NMR and IR supported by HRFABMS. GRE (glucocorticoid response element)- and ARE (androgen response element)-mediated luciferase reporter gene assays were used to screen for the biological activities of 1 and its metabolites. Compounds 7, 13, 16, and 18 showed significantly enhanced GRE-mediated luciferase activity, but at levels less than that induced by either methylprednisolone or dexamethasone. On the other hand, compounds 3, 4, 12, 13, 14, and 18 showed significant effects on ARE-mediated luciferase activity; in particular, 3, 12, 14, and 18 were more active than testosterone.",
author = "Chang, {Shwu Fen} and Yang, {Li Ming} and Lo, {Chia Hsin} and Liaw, {Jia Horng} and Wang, {Li Hsuan} and Lin, {Shwu Jiuan}",
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T1 - Microbial transformation of isosteviol and bioactivities against the glucocorticoid/androgen response elements

AU - Chang, Shwu Fen

AU - Yang, Li Ming

AU - Lo, Chia Hsin

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AU - Wang, Li Hsuan

AU - Lin, Shwu Jiuan

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