Oxidation and ring cleavage of dibenzofuran by the filamentous fungus Paecilomyces lilacinus.
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.
Gesell
Manuela
M
Institut für Mikrobiologie und Molekularbiologie, Ernst-Moritz-Arndt-Universität Greifswald, F.-L.-Jahn-Str. 15, 17487, Greifswald, Germany. gesell@uni-greifswald.de
Hammer
Elke
E
Mikolasch
Annett
A
Schauer
Frieder
F
D001572:Benzofurans / Q000378:metabolism*; D001711:Biotransformation; D006900:Hydroxylation; D010084:Oxidation-Reduction; D010143:Paecilomyces / Q000254:growth & development / Q000378:metabolism*; D012988:Soil Microbiology
D001572:Benzofurans; C023614:dibenzofuran