The microbiological transformation of some ent-kaur-6, 16-dienes by Gibberella fujikuroi

The preparation of ent-kaur-6, 16-diene and ent-18-hydrosykaur-6, 16-diene from epicandicandiol and of ent-3B, 18-dihydroxykaur-6, 16-diene from foliol is described. On incubation with Gibberella fujikuroi ent-kaur-6, 16-diene gave 7-hydroxykaurenolide and 18-hydroxykaur-6, 16-diene afforded 7, 18-d...

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Bibliographic Details
Authors: Fraga, Braulio M., González, Antonio G., González, Pedro, Hanson, James R., Hernández, Melchor G.
Format: article
Publication Date:1983
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/22134
Online Access:http://hdl.handle.net/10261/22134
Access Level:Open access
Keyword:Gibberella fujikuroi
ent-kaur-6, 16-dienes
ent-6a, 7a-epoxy-3B, 18-dihydroxykaur-16-3n3
kaurenolide biosynthesis
Description
Summary:The preparation of ent-kaur-6, 16-diene and ent-18-hydrosykaur-6, 16-diene from epicandicandiol and of ent-3B, 18-dihydroxykaur-6, 16-diene from foliol is described. On incubation with Gibberella fujikuroi ent-kaur-6, 16-diene gave 7-hydroxykaurenolide and 18-hydroxykaur-6, 16-diene afforded 7, 18-dihydroxykaurenolide, whilst ent-6a,7a-epoxy-3B,18-dihydroxykaur-16-ene was obtained from ent-3B,18-dihydroxykaur-6,16-diene. The possible biosynthetic significance of the 6, 7-epoxidation in kaurenolide formation is noted.

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