Microbial transformation of isosteviol lactone and evaluation of the transformation products on androgen response element

Bo Hon Chou; Li Ming Yang; Shwu Fen Chang; Feng-Lin Hsu; Chia Hsin Lo; Jia Horng Liaw; Pan Chun Liu; Shwu Jiuan Lin

doi:10.1021/np070585b

Microbial transformation of isosteviol lactone and evaluation of the transformation products on androgen response element

Bo Hon Chou, Li Ming Yang, Shwu Fen Chang, Feng-Lin Hsu, Chia Hsin Lo, Jia Horng Liaw, Pan Chun Liu, Shwu Jiuan Lin

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

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
Pages (from-to)	602-607
Number of pages	6
Journal	Journal of Natural Products
Volume	71
Issue number	4
DOIs	https://doi.org/10.1021/np070585b
Publication status	Published - Apr 2008

ASJC Scopus subject areas

Plant Science
Chemistry (miscellaneous)
Drug Discovery
Organic Chemistry
Pharmacology

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10.1021/np070585b

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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
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
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

Cite this

Microbial transformation of isosteviol lactone and evaluation of the transformation products on androgen response element. / Chou, Bo Hon; Yang, Li Ming; Chang, Shwu Fen; Hsu, Feng-Lin; Lo, Chia Hsin; Liaw, Jia Horng; Liu, Pan Chun; Lin, Shwu Jiuan.

In: Journal of Natural Products, Vol. 71, No. 4, 04.2008, p. 602-607.

Research output: Contribution to journal › Article › peer-review

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title = "Microbial transformation of isosteviol lactone and evaluation of the transformation products on androgen response element",

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.",

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AU - Liaw, Jia Horng

AU - Liu, Pan Chun

AU - Lin, Shwu Jiuan

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AB - 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.

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Microbial transformation of isosteviol lactone and evaluation of the transformation products on androgen response element

Abstract

ASJC Scopus subject areas

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CCDC 660700: Experimental Crystal Structure Determination

CCDC 660698: Experimental Crystal Structure Determination

CCDC 660699: Experimental Crystal Structure Determination

Cite this