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

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33 引文 斯高帕斯(Scopus)

摘要

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.

原文英語
頁(從 - 到)87-92
頁數6
期刊Journal of Natural Products
71
發行號1
DOIs
出版狀態已發佈 - 一月 2008

ASJC Scopus subject areas

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

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