Bacterial oxidation of chemical carcinogens: formation of polycyclic aromatic acids from benz[a]anthracene.
A Beijerinckia strain designated strain B1 was shown to oxidize benz[a]anthracene after induction with biphenyl, m-xylene, and salicylate. Biotransformation experiments showed that after 14 h a maximum of 56% of the benz[a]anthracene was converted to an isomeric mixture of three o-hydroxypolyaromatic acids. Nuclear magnetic resonance and mass spectral analyses led to the identification of the major metabolite as 1-hydroxy-2-anthranoic acid. Two minor metabolites were also isolated and identified as 2-hydroxy-3-phenanthroic acid and 3-hydroxy-2-phenanthroic acid. Mineralization experiments with [12-14C]benz[a]anthracene led to the formation of 14CO2. These results show that the hydroxy acids can be further oxidized and that at least two rings of the benz[a]anthracene molecule can be degraded.
Mahaffey
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WR
Center for Applied Microbiology, University of Texas, Austin 78712.
Gibson
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Cerniglia
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CE
D001551:Benz(a)Anthracenes / Q000378:metabolism*; D001673:Biodegradation, Environmental; D001713:Biphenyl Compounds / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000378:metabolism*; D011548:Pseudomonadaceae / Q000378:metabolism*; D012459:Salicylates / Q000494:pharmacology; D014992:Xylenes / Q000494:pharmacology
D001551:Benz(a)Anthracenes; D001713:Biphenyl Compounds; D011083:Polycyclic Compounds; D012459:Salicylates; D014992:Xylenes; C030935:benz(a)anthracene; C031285:3-xylene