4.7 Article

Hydroxylation of the diterpenes ent-kaur-16-en-19-oic and ent-beyer-15-en-19-oic acids by the fungus Aspergillus niger

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PHYTOCHEMISTRY
卷 70, 期 17-18, 页码 2017-2022

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2009.09.005

关键词

Aspergillus niger; Biotransformation; Kaurenoic acid; Beyerenoic acid; Spasmolytic activity

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The diterpenes ent-kaur-16-en-19-oic acid (1) and ent-beyer-15-en-19-oic acid (2) are the major constituents of a spasmolytic diterpenic mixture obtained from the roots of Viguiera hypargyrea, a Mexican medicinal plant. Microbial transformation of 1 and 2 was performed with Aspergillus niger. Two metabolites, ent-7 alpha,11 beta-dihydroxy-kaur-16-en-19-oic acid (4) and ent-1 beta,7 alpha-dihydroxy-kaur-16-en-19-oic acid (5), were isolated from the incubation of 1, and one metabolite, ent-1 beta,7 alpha-dihydroxy-beyer-15-en-19-oic acid (6), was isolated in high yield (40%) from 2. The structures were elucidated on the basis of spectroscopic analyses and confirmed by X-ray crystallographic studies. Compounds 1-4 and 6 and methyl ester derivatives 4a and 6a were evaluated for their ability to inhibit the electrically induced contraction of guinea-pig ileum. Compounds 1, 3, 4, 4a and 5 were significantly active. These results showed that dihydroxylation of 1 at 7 beta, 11 alpha-, and 1 alpha, 7 beta-positions resulted in a loss of potency. (C) 2009 Elsevier Ltd. All rights reserved.

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