Document Detail


Oxidation and ring cleavage of dibenzofuran by the filamentous fungus Paecilomyces lilacinus.
MedLine Citation:
PMID:  15278240     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The ability of the imperfect soil fungus Paecilomyces lilacinus to transform the environmental pollutant dibenzofuran was investigated. Transformation of dibenzofuran and related derivatives lead to 14 products, which were identified by UV spectroscopy, mass spectrometry, and proton nuclear magnetic resonance spectroscopy. Biotransformation was initiated by two separate hydroxylation steps, leading to the accumulation of 4-monohydroxylated and 4-dihydroxylateddibenzofurans. Hydroxylation at both aromatic rings produced 2,7-dihydroxydibenzofuran, 3,7-dihydroxydibenzofuran, and 2,8-dihydroxydibenzofuran. Further oxidation yields ring cleavage of dibenzofuran, which has not been described before for filamentous fungi. The ring fission products were identified as benzo[ b]furo[3,2-d]-2-pyrone-6-carboxylic acid and [2-(1-carboxy-methylidene)-benzofuran-3-ylidene]-hydroxy-acetic acid and its derivatives hydroxylated at carbon 7 and 8 at the non-cleaved ring. Other metabolites were riboside-conjugates of 2-hydroxydibenzofuran and 3-hydroxydibenzofuran. The results showed that P. lilacinus transforms the hydrophobic compound dibenzofuran by phase I/phase II reactions to produce hydroxylated products and excretable sugar conjugates.
Authors:
Manuela Gesell; Elke Hammer; Annett Mikolasch; Frieder Schauer
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2004-07-28
Journal Detail:
Title:  Archives of microbiology     Volume:  182     ISSN:  0302-8933     ISO Abbreviation:  Arch. Microbiol.     Publication Date:  2004 Sep 
Date Detail:
Created Date:  2004-08-18     Completed Date:  2004-11-19     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0410427     Medline TA:  Arch Microbiol     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  51-9     Citation Subset:  IM    
Affiliation:
Institut für Mikrobiologie und Molekularbiologie, Ernst-Moritz-Arndt-Universität Greifswald, F.-L.-Jahn-Str. 15, 17487, Greifswald, Germany. gesell@uni-greifswald.de
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MeSH Terms
Descriptor/Qualifier:
Benzofurans / metabolism*
Biotransformation
Hydroxylation
Oxidation-Reduction
Paecilomyces / growth & development,  metabolism*
Soil Microbiology
Chemical
Reg. No./Substance:
0/Benzofurans; 132-64-9/dibenzofuran

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


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