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Closed Access item Biotransformation of two ent-Pimara-9(11),15-diene derivatives by Gibberella fujikuroi

Authors:Fraga, Braulio M.
Guillermo, Ricardo
Hernández, Melchor G.
Chamy, María C.
Garbarino, Juan A.
Issue Date:7-Jan-2009
Publisher:American Chemical Society
American Society of Pharmacognosy
Citation:Journal of Natural Products 72(1): 87-91 (2009)
Abstract:The incubation of 19-hydroxy-13-epi-ent-pimara-9(11),15-diene (4) with Gibberella fujikuroi gave 8α,19-dihydroxy-9α,11α-epoxy-13-epi-ent-pimara-15-ene (6), 7-oxo-11α,19-dihydroxy-13-epi-ent-pimara-8(9),15-diene (7), 7-oxo-11β,19-dihydroxy-13-epi-ent-pimara-8(9),15-diene (9), and 8α,19-dihydroxy-9α,11α:15,16-diepoxy-13-epi-ent-pimarane (11), while the feeding of 13-epi-ent-pimara-9(11),15-diene-19-oic acid (5) with this fungus afforded 1-oxo-2α,9α-dihydroxy-13-epi-ent-pimara-11,15-dien-19-oic acid (13), 1-oxo-2β,9α-dihydroxy-13-epi-ent-pimara-11,15-dien-19-oic acid (14), 13-epi-ent-pimara-9(11),15-dien-1,19-dioic acid 1,2-lactone (15), and 1-oxo-12β-hydroxy-13-epi-ent-pimara-9(11),15-dien-19-oic acid (16). In both biotransformations, the main reaction was the epoxidation of the 9(11)-double bond, followed by rearrangement to afford allylic alcohols. The formation of lactone 15 represents the first time that a Baeyer−Villiger oxidation has been observed in a microbiological transformation with this fungus.
Description:5 pages, 1 figure, 1 table.-- PMID: 19128148 [PubMed].-- Printed version published Jan 23, 2009.
Publisher version (URL):http://dx.doi.org/10.1021/np800647v
URI:http://hdl.handle.net/10261/14367
ISSN:0163-3864
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