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

研究成果: 雜誌貢獻文章

28 引文 (Scopus)

摘要

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.

原文英語
頁(從 - 到)273-277
頁數5
期刊Journal of Natural Products
65
發行號3
DOIs
出版狀態已發佈 - 2002

指紋

Acids
acids
Metabolites
Cunninghamella
metabolites
Actinoplanes
Mucor
isosteviol
Diterpenes
antihypertensive effect
Antihypertensive Agents
diterpenoids
spectral analysis
Nuclear magnetic resonance

ASJC Scopus subject areas

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

引用此文

Hsu, F-L., Hou, C. C., Yang, L. M., Cheng, J. T., Chi, T. C., Liu, P. C., & Lin, S. J. (2002). Microbial transformations of isosteviol. Journal of Natural Products, 65(3), 273-277. https://doi.org/10.1021/np000622y

Microbial transformations of isosteviol. / Hsu, Feng-Lin; Hou, Chia Chung; Yang, Li Ming; Cheng, Juei Tang; Chi, Tzong Cherng; Liu, Pang Chun; Lin, Shwu Jiuan.

於: Journal of Natural Products, 卷 65, 編號 3, 2002, p. 273-277.

研究成果: 雜誌貢獻文章

Hsu, F-L, Hou, CC, Yang, LM, Cheng, JT, Chi, TC, Liu, PC & Lin, SJ 2002, 'Microbial transformations of isosteviol', Journal of Natural Products, 卷 65, 編號 3, 頁 273-277. https://doi.org/10.1021/np000622y
Hsu F-L, Hou CC, Yang LM, Cheng JT, Chi TC, Liu PC 等. Microbial transformations of isosteviol. Journal of Natural Products. 2002;65(3):273-277. https://doi.org/10.1021/np000622y
Hsu, Feng-Lin ; Hou, Chia Chung ; Yang, Li Ming ; Cheng, Juei Tang ; Chi, Tzong Cherng ; Liu, Pang Chun ; Lin, Shwu Jiuan. / Microbial transformations of isosteviol. 於: Journal of Natural Products. 2002 ; 卷 65, 編號 3. 頁 273-277.
@article{1d65cb5f7ddc41fcb1525baa301b0258,
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}",
year = "2002",
doi = "10.1021/np000622y",
language = "English",
volume = "65",
pages = "273--277",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "3",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0036198873&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0036198873&partnerID=8YFLogxK

U2 - 10.1021/np000622y

DO - 10.1021/np000622y

M3 - Article

C2 - 11908964

AN - SCOPUS:0036198873

VL - 65

SP - 273

EP - 277

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 3

ER -