Author:
Cerniglia C E,Freeman J P,Mitchum R K
Abstract
Cunninghamella elegans oxidized naphthalene to ethyl acetate-soluble and water-soluble metabolites. Experiments with [14C]-naphthalene indicated that 21% of the substrate was converted into metabolites. The ratio of organic-soluble metabolites to water-soluble metabolites was 76:24. The major ethyl acetate-soluble naphthalene metabolites were trans-1,2-dihydroxy-1,2-dihydro-naphthalene, 4-hydroxy-1-tetralone, and 1-naphthol. Enzymatic treatment of the aqueous phase with either arylsulfatase or beta-glucuronidase released metabolites of naphthalene that were extractable with ethyl acetate. In both cases, the major metabolite was 1-naphthol. The ratio of water-soluble sulfate conjugates to water-soluble glucuronide conjugates was 1:1. Direct analysis of the aqueous phase by high-pressure liquid and thin-layer chromatographic and mass spectrometric techniques indicated that 1-naphthyl sulfate and 1-naphthyl glucuronic acid were major water-soluble metabolites formed from the fungal metabolism of naphthalene. C. elegans oxidized biphenyl primarily to 4-hydroxy biphenyl. Deconjugation experiments with biphenyl water-soluble metabolites indicated that the glucuronide and sulfate ester of 4-hydroxy biphenyl were metabolites. The data demonstrate that sulfation and glucuronidation are major pathways in the metabolism of aromatic hydrocarbons by fungi.
Publisher
American Society for Microbiology
Subject
Ecology,Applied Microbiology and Biotechnology,Food Science,Biotechnology
Reference12 articles.
1. Cerniglia C. E. 1981. Aromatic hydrocarbons: metabolism by bacteria fungi and algae p. 321-361. In Reviews in Biochemical Toxicology (E. Hodgson J. R. Bend R. M. Philpot) Vol. 3. Elsevier/North Holland New York.
2. Metabolism of naphthalene by Cunninghamella elegans;Cerniglia C. E.;AppI. Environ. Microbiol.,1977
3. Metabolism of naphthalene by cell extracts of Cunninghamella elegans;Cerniglia C. E.;Arch. Biochem. Biophys.,1978
4. Fungal transformation of naphthalene;Cerniglia C. E.;Arch. Microbiol.,1978
5. Fungal metabolism of biphenyl;Dodge R. H.;Biochem. J.,1979
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