Microbial metabolism of fluoranthene: isolation and identification of ring fission products

SummaryThe degradation of fluoranthene by pure cultures of Alcaligenes denitrificanss WW1, isolated from contaminated soil samples, was investigated. The strain showed maximum degradation rates of 0.3 mg fluoranthene/ml per day. A denitrificans was able to utilize also naphthalene, 1- and 2-methylnaphthalene, phenanthrene, and anthracene as sole carbon sources and to co-metabolize fuuorence, pyrene, and benzo(a)anthracene. During growth on fluoranthene in batch culture two metabolic products that were completely degraded before growth entered the stationary phase were detected in the culture fluid. Anslyses by UV, mass and NMR spectroscopy identified the products as acenaphthenone and 3-hydroxymethyl-4,5-benzocoumarine. Fluoranthene-grown resting cells of A. denitrificans showed degradative activity towards 2,3-dihydroxybenzoic acid, pyrogallol, salicylic acid, and catechol. The enzymatic activities in extracts of fluoranthene-induced cells indicate a meta ring fission involved in the degradation of fluoranthene. From these data new aspects of the biodegradative pathway of fluoranthene have been predicted.

[1]  C. Cerniglia.  Microbial metabolism of polycyclic aromatic hydrocarbons. , 1984, Advances in applied microbiology.

[2]  E. A. Barnsley.  Naphthalene metabolism by pseudomonads: the oxidation of 1,2-dihydroxynaphthalene to 2-hydroxychromene-2-carboxylic acid and the formation of 2'-hydroxybenzalpyruvate. , 1976, Biochemical and biophysical research communications.

[3]  M. Nozaki.  [65] Metapyrocatechase (Pseudomonas)☆ , 1970 .

[4]  P J Chapman,et al.  Isolation and characterization of a fluoranthene-utilizing strain of Pseudomonas paucimobilis , 1990, Applied and environmental microbiology.

[5]  N. Pfennig,et al.  Über das Vitamin B12-Bedürfnis phototropher Schwefelbakterien , 1966, Archiv für Mikrobiologie.

[6]  L. Fieser,et al.  o-Halide Synthesis of 10-Methyl-1',9-methylene-1,2-benzanthracene , 1940 .

[7]  K. White.  An overview of immunotoxicology and carcinogenic polycyclic aromatic hydrocarbons , 1986 .

[8]  E. A. Barnsley.  The bacterial degradation of fluoranthene and benzo[alpyrene. , 1975, Canadian journal of microbiology.

[9]  C. Cerniglia,et al.  Pyrene degradation by a Mycobacterium sp.: identification of ring oxidation and ring fission products , 1988, Applied and environmental microbiology.

[10]  P. Trudgill,et al.  The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL 1. , 1972, The Biochemical journal.

[11]  C. Poh,et al.  Evidence for isofunctional enzymes used in m-cresol and 2,5-xylenol degradation via the gentisate pathway in Pseudomonas alcaligenes , 1980, Journal of bacteriology.

[12]  H. N. Fernley,et al.  OXIDATIVE METABOLISM OF PHENANTHRENE AND ANTHRACENE BY SOIL PSEUDOMONADS. THE RING-FISSION MECHANISM. , 1965, Biochemical Journal.

[13]  M. M. Bradford.  A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. , 1976, Analytical biochemistry.

[14]  C. Cerniglia,et al.  Bacterial oxidation of chemical carcinogens: formation of polycyclic aromatic acids from benz[a]anthracene , 1988, Applied and environmental microbiology.

[15]  Ronald A. Hites,et al.  The global distribution of polycyclic aromatic hydrocarbons in recent sediments , 1978 .

[16]  D. Gibson,et al.  Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene , 1984, Applied and environmental microbiology.

[17]  K. Rinehart,et al.  A New Acyclic Acid Metabolite in Camphor Oxidation , 1966 .

[18]  W. Franklin,et al.  Microbial metabolism of polycyclic aromatic hydrocarbons: isolation and characterization of a pyrene-degrading bacterium , 1988, Applied and environmental microbiology.

[19]  J. Paul Robinson.  Oxidative Metabolism , 1997, Current protocols in cytometry.

[20]  J. Bumpus.  Biodegradation of polycyclic hydrocarbons by Phanerochaete chrysosporium , 1989, Applied and environmental microbiology.

[21]  D. Gibson.  Microbial degradation of organic compounds. , 1984 .

[22]  M. Nozaki,et al.  Metapyrocatechase. 3. Substrate specificity and mode of ring fission. , 1970, Biochimica et biophysica acta.

[23]  M. Nozaki,et al.  Cleavage of pyrogallol by non-heme iron-containing dioxygenases. , 1980, The Journal of biological chemistry.

[24]  I. C. Gunsalus,et al.  An enzyme system for cyclic ketone lactonization. , 1961, Biochemical and biophysical research communications.

[25]  A. Baeyer,et al.  Einwirkung des Caro'schen Reagens auf Ketone , 1899 .

[26]  Jürgen Klein,et al.  Degradation of phenanthrene, fluorene and fluoranthene by pure bacterial cultures , 2004, Applied Microbiology and Biotechnology.

[27]  P. Trudgill,et al.  The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB 9871. , 1976, European journal of biochemistry.

[28]  O. Pelkonen,et al.  Mutagenicity studies of different polycyclic aromatic hydrocarbons: the significance of enzymatic factors and molecular structure. , 1987, Carcinogenesis.

[29]  A. Nakazawa,et al.  [64] Pyrocatechase (pseudomonas) , 1970 .