Biotransformation of Two ent-Pimara-9(11),15-diene Derivatives by Gibberella fujikuroi
| Autor: | Ricardo Guillermo, Melchor G. Hernández, Juan A. Garbarino, Braulio M. Fraga, María C. Chamy |
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| Rok vydání: | 2009 |
| Předmět: |
Pharmacology
Molecular Structure biology Diene Gibberella Stereochemistry Organic Chemistry Pharmaceutical Science Stereoisomerism biology.organism_classification Analytical Chemistry Microbiology chemistry.chemical_compound Complementary and alternative medicine Biotransformation chemistry Abietanes Drug Discovery Molecular Medicine Gibberella fujikuroi Nuclear Magnetic Resonance Biomolecular Oxidation-Reduction Incubation |
| Zdroj: | Journal of Natural Products. 72:87-91 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np800647v |
| Popis: | The incubation of 19-hydroxy-13-epi-ent-pimara-9(11),15-diene (4) with Gibberella fujikuroi gave 8 alpha,19-dihydroxy-9 alpha,11alpha-epoxy-13-epi-ent-pimara-15-ene (6), 7-oxo-11 alpha,19-dihydroxy-13-epi-ent-pimara-8(9),15-diene (7), 7-oxo-11beta,19-dihydroxy-13-epi-ent-pimara-8(9),15-diene (9), and 8 alpha,19-dihydroxy-9 alpha,11 alpha: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-2 alpha,9 alpha-dihydroxy-13-epi-ent-pimara-11,15-dien-19-oic acid (13), 1-oxo-2 beta,9 alpha-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-12 beta-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. |
| Databáze: | OpenAIRE |
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