PMID: 11908964Mar 23, 2002Paper

Microbial transformations of isosteviol

Journal of Natural Products
Feng-Lin HsuShwu-Jiuan Lin

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-11alpha,12alpha-dihydroxy-16-ketobeyeran-19-oic acid (5), ent-11alpha,12alpha,17-trihydroxy-16-ketobeyeran-19-oic acid (6), ent-12alpha,15alpha-dihydroxy-16-ketobeyeran-19-oic acid (7), ent-7alpha,15alpha-dihydroxy-16- ketobeyeran-19-oic acid (8), and ent-9alpha-hydroxy-16-ketobeyeran-19-oic acid (9), together with three known metabolites, ent-7alpha-hydroxy-16-ketobeyeran-19-oic acid (3), ent-7beta-hydroxy-16-ketobeyeran-19-oic acid (4), and ent-12alpha-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.

References

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Citations

Nov 18, 2006·Applied Microbiology and Biotechnology·Feng-Lin HsuShwu-Jiuan Lin
Jul 29, 2009·Applied Microbiology and Biotechnology·Jamie E PriorRyan T Gill
Mar 8, 2013·European Journal of Medicinal Chemistry·Orawan WongananApichart Suksamrarn
Sep 9, 2008·Biotechnology Advances·Sepuri Asha, Maravajhala Vidyavathi
May 31, 2016·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·Hong-Xia FanHao Gao
Nov 17, 2007·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Antonio Osorio-LozadaRaju Subramanian

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