Document Detail


Biotransformation of ent-13-epi-manoyl oxides difunctionalized at C-3 and C-12 by filamentous fungi.
MedLine Citation:
PMID:  14697276     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Biotransformation of ent-3beta,12alpha-dihydroxy-13-epi-manoyl oxide with Fusarium moniliforme gave the regioselective oxidation of the hydroxyl group at C-3 and the ent-7beta-hydroxylation. The action of Gliocladium roseum in the 3,12-diketoderivative originated monohydroxylations at C-1 and C-7, both by the ent-beta face, while Rhizopus nigricans produced hydroxylation at C-7 or C-18, epoxidation of the double bond, reduction of the keto group at C-3, and combined actions as biohydroxylation at C-2/epoxidation of the double bond and hydroxylation at C-7/reduction of the keto group at C-3. In the ent-3-hydroxy-12-keto epimers, G. roseum originated monohydroxylations at C-1 and C-7 and R. nigricans originated the oxidation at C-3 as a major transformation, epoxidation of double bond and hydroxylation at C-2. Finally, in the ent-3beta-hydroxy epimer R. nigricans also originated minor hydroxylations at C-1, C-6, C-7 and C-20 and F. moniliforme produced an hydroxylation at C-7 and a dihydroxylation at C-7/C-11.
Authors:
Andrés García-Granados; Antonia Fernández; María C Gutiérrez; Antonio Martínez; Raquel Quirós; Francisco Rivas; José M Arias
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Phytochemistry     Volume:  65     ISSN:  0031-9422     ISO Abbreviation:  Phytochemistry     Publication Date:  2004 Jan 
Date Detail:
Created Date:  2003-12-30     Completed Date:  2004-03-05     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0151434     Medline TA:  Phytochemistry     Country:  United States    
Other Details:
Languages:  eng     Pagination:  107-15     Citation Subset:  IM    
Affiliation:
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, E-18071, Granada, Spain. agarcia@ugr.es
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MeSH Terms
Descriptor/Qualifier:
Biotransformation
Epoxy Compounds / chemistry
Fusarium / metabolism*
Gliocladium / metabolism*
Hydroxylation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Oxidation-Reduction
Rhizopus / metabolism*
Stereoisomerism
Terpenes / chemistry*,  metabolism*
Chemical
Reg. No./Substance:
0/Epoxy Compounds; 0/Terpenes; 0/ent-13-epi-manoyl oxide

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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