Microbial transformations of isosteviol

Feng-Lin Hsu; Chia Chung Hou; Li Ming Yang; Juei Tang Cheng; Tzong Cherng Chi; Pang Chun Liu; Shwu Jiuan Lin

doi:10.1021/np000622y

Microbial transformations of isosteviol

Feng-Lin Hsu, Chia Chung Hou, Li Ming Yang, Juei Tang Cheng, Tzong Cherng Chi, Pang Chun Liu, Shwu Jiuan Lin

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32 Citations (Scopus)

Abstract

Microbial transformations of the tetracyclic diterpenoid isosteviol (ent-16-ketobeyeran-19-oic acid) (2) have revealed that isosteviol is metabolized by Cunninghamella bainieri, Actinoplanes sp., Mucor recurvatus, and Cunninghamella blakesleeana to yield five new metabolites, ent-11α,12α-dihydroxy-16-ketobeyeran-19-oic acid (5), ent-11α,12α,17-trihydroxy-16-ketobeyeran-19-oic acid (6), ent-12α, 15α-dihydroxy-16-ketobeyeran-19-oic acid (7), ent-7α,15α-dihydroxy-16-ketobeyeran-19-oic acid (8), and ent-9α-hydroxy-16-ketobeyeran-19-oic acid (9), together with three known metabolites, ent-7α-hydroxy-16-ketobeyeran-19-oic acid (3), ent-7β-hydroxy-16-ketobeyeran-19-oic acid (4), and ent-12α-hydroxy-16-ketobeyeran-19-oic acid (10). The structures of these metabolites were established on the basis of HRFABMS and 1D and 2D NMR spectral data. In addition, metabolites 3-10 were tested for antihypertensive activity and were found to be less active than the parent compound 2.

Original language	English
Pages (from-to)	273-277
Number of pages	5
Journal	Journal of Natural Products
Volume	65
Issue number	3
DOIs	https://doi.org/10.1021/np000622y
Publication status	Published - 2002

ASJC Scopus subject areas

Plant Science
Chemistry (miscellaneous)
Drug Discovery
Organic Chemistry
Pharmacology

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title = "Microbial transformations of isosteviol",

abstract = "Microbial transformations of the tetracyclic diterpenoid isosteviol (ent-16-ketobeyeran-19-oic acid) (2) have revealed that isosteviol is metabolized by Cunninghamella bainieri, Actinoplanes sp., Mucor recurvatus, and Cunninghamella blakesleeana to yield five new metabolites, ent-11α,12α-dihydroxy-16-ketobeyeran-19-oic acid (5), ent-11α,12α,17-trihydroxy-16-ketobeyeran-19-oic acid (6), ent-12α, 15α-dihydroxy-16-ketobeyeran-19-oic acid (7), ent-7α,15α-dihydroxy-16-ketobeyeran-19-oic acid (8), and ent-9α-hydroxy-16-ketobeyeran-19-oic acid (9), together with three known metabolites, ent-7α-hydroxy-16-ketobeyeran-19-oic acid (3), ent-7β-hydroxy-16-ketobeyeran-19-oic acid (4), and ent-12α-hydroxy-16-ketobeyeran-19-oic acid (10). The structures of these metabolites were established on the basis of HRFABMS and 1D and 2D NMR spectral data. In addition, metabolites 3-10 were tested for antihypertensive activity and were found to be less active than the parent compound 2.",

author = "Feng-Lin Hsu and Hou, {Chia Chung} and Yang, {Li Ming} and Cheng, {Juei Tang} and Chi, {Tzong Cherng} and Liu, {Pang Chun} and Lin, {Shwu Jiuan}",

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pages = "273--277",

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T1 - Microbial transformations of isosteviol

AU - Hsu, Feng-Lin

AU - Hou, Chia Chung

AU - Yang, Li Ming

AU - Cheng, Juei Tang

AU - Chi, Tzong Cherng

AU - Liu, Pang Chun

AU - Lin, Shwu Jiuan

PY - 2002

Y1 - 2002

N2 - Microbial transformations of the tetracyclic diterpenoid isosteviol (ent-16-ketobeyeran-19-oic acid) (2) have revealed that isosteviol is metabolized by Cunninghamella bainieri, Actinoplanes sp., Mucor recurvatus, and Cunninghamella blakesleeana to yield five new metabolites, ent-11α,12α-dihydroxy-16-ketobeyeran-19-oic acid (5), ent-11α,12α,17-trihydroxy-16-ketobeyeran-19-oic acid (6), ent-12α, 15α-dihydroxy-16-ketobeyeran-19-oic acid (7), ent-7α,15α-dihydroxy-16-ketobeyeran-19-oic acid (8), and ent-9α-hydroxy-16-ketobeyeran-19-oic acid (9), together with three known metabolites, ent-7α-hydroxy-16-ketobeyeran-19-oic acid (3), ent-7β-hydroxy-16-ketobeyeran-19-oic acid (4), and ent-12α-hydroxy-16-ketobeyeran-19-oic acid (10). The structures of these metabolites were established on the basis of HRFABMS and 1D and 2D NMR spectral data. In addition, metabolites 3-10 were tested for antihypertensive activity and were found to be less active than the parent compound 2.

AB - Microbial transformations of the tetracyclic diterpenoid isosteviol (ent-16-ketobeyeran-19-oic acid) (2) have revealed that isosteviol is metabolized by Cunninghamella bainieri, Actinoplanes sp., Mucor recurvatus, and Cunninghamella blakesleeana to yield five new metabolites, ent-11α,12α-dihydroxy-16-ketobeyeran-19-oic acid (5), ent-11α,12α,17-trihydroxy-16-ketobeyeran-19-oic acid (6), ent-12α, 15α-dihydroxy-16-ketobeyeran-19-oic acid (7), ent-7α,15α-dihydroxy-16-ketobeyeran-19-oic acid (8), and ent-9α-hydroxy-16-ketobeyeran-19-oic acid (9), together with three known metabolites, ent-7α-hydroxy-16-ketobeyeran-19-oic acid (3), ent-7β-hydroxy-16-ketobeyeran-19-oic acid (4), and ent-12α-hydroxy-16-ketobeyeran-19-oic acid (10). The structures of these metabolites were established on the basis of HRFABMS and 1D and 2D NMR spectral data. In addition, metabolites 3-10 were tested for antihypertensive activity and were found to be less active than the parent compound 2.

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Microbial transformations of isosteviol

Abstract

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