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 | |
| Publication status | Published - Apr 2008 |
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ASJC Scopus subject areas
- Plant Science
- Chemistry (miscellaneous)
- Drug Discovery
- Organic Chemistry
- Pharmacology
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
}
TY - JOUR
T1 - Microbial transformation of isosteviol lactone and evaluation of the transformation products on androgen response element
AU - Chou, Bo Hon
AU - Yang, Li Ming
AU - Chang, Shwu Fen
AU - Hsu, Feng-Lin
AU - Lo, Chia Hsin
AU - Liaw, Jia Horng
AU - Liu, Pan Chun
AU - Lin, Shwu Jiuan
PY - 2008/4
Y1 - 2008/4
N2 - 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.
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.
UR - http://www.scopus.com/inward/record.url?scp=43249131415&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=43249131415&partnerID=8YFLogxK
U2 - 10.1021/np070585b
DO - 10.1021/np070585b
M3 - Article
C2 - 18275152
AN - SCOPUS:43249131415
VL - 71
SP - 602
EP - 607
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 4
ER -