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Microbial transformation of 18-hydroxy-9,13-epi-ent-pimara-7,15-diene by Gibberella fujikuroi

AuthorsFraga, Braulio M. ; González, Pedro; Hernández, Melchor G.; Chamy, María C.; Garbarino, Juan A.
Issue Date2003
PublisherAmerican Chemical Society
CitationJournal of Natural Products 66: pp. 392-397 (2003)
AbstractThe incubation of the diterpene 18-dihydroxy-9,13-epi-ent-pimara-7,15-diene(3) with the fungus Gibberella fujikuroi gave 14 metabolites, 4 and 6-18. The carbons functionalized were the C-20 methyl and all the secondaries, except C-12. The main reaction observed was the epoxidation of the 7,8-double bond, which rearranged to form 7-keto derivatives, such as 10-17, or the allylic alcohol 18. Compound 9 was the only one obtained in which the 7,8-double bond of the substrate remained unaltered. This work confirms that, in the feeding of this type of diterpene with this fungus, the oxidation at C-19, typical of the biosynthesis of gibberellins from ent-kaur-16-ene. is inhibited.
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