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 language | English |
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Pages (from-to) | 602-607 |
Number of pages | 6 |
Journal | Journal of Natural Products |
Volume | 71 |
Issue number | 4 |
DOIs | |
Publication status | Published - Apr 2008 |
ASJC Scopus subject areas
- Plant Science
- Chemistry (miscellaneous)
- Drug Discovery
- Organic Chemistry
- Pharmacology
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CCDC 660699: Experimental Crystal Structure Determination
Chou, B. (Contributor), Yang, L. (Contributor), Chang, S. (Contributor), Hsu, F. (Contributor), Lo, C. (Contributor), Liaw, J. (Contributor), Liu, P. (Contributor) & Lin, S. (Contributor), Unknown Publisher, Jan 1 2009
DOI: 10.5517/ccq5hw7, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccq5hw7&sid=DataCite
Dataset
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CCDC 660698: Experimental Crystal Structure Determination
Chou, B. (Contributor), Yang, L. (Contributor), Chang, S. (Contributor), Hsu, F. (Contributor), Lo, C. (Contributor), Liaw, J. (Contributor), Liu, P. (Contributor) & Lin, S. (Contributor), Unknown Publisher, Jan 1 2009
DOI: 10.5517/ccq5hv6, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccq5hv6&sid=DataCite
Dataset
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CCDC 660700: Experimental Crystal Structure Determination
Chou, B. (Contributor), Yang, L. (Contributor), Chang, S. (Contributor), Hsu, F. (Contributor), Lo, C. (Contributor), Liaw, J. (Contributor), Liu, P. (Contributor) & Lin, S. (Contributor), Unknown Publisher, Jan 1 2009
DOI: 10.5517/ccq5hx8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccq5hx8&sid=DataCite
Dataset