Biodegradation of polycyclic aromatic hydrocarbons

The intent of this review is to provide an outline of the microbial degradation of polycyclic aromatic hydrocarbons. A catabolically diverse microbial community, consisting of bacteria, fungi and algae, metabolizes aromatic compounds. Molecular oxygen is essential for the initial hydroxylation of polycyclic aromatic hydrocarbons by microorganisms. In contrast to bacteria, filamentous fungi use hydroxylation as a prelude to detoxification rather than to catabolism and assimilation. The biochemical principles underlying the degradation of polycyclic aromatic hydrocarbons are examined in some detail. The pathways of polycyclic aromatic hydrocarbon catabolism are discussed. Studies are presented on the relationship between the chemical structure of the polycyclic aromatic hydrocarbon and the rate of polycyclic aromatic hydrocarbon biodegradation in aquatic and terrestrial ecosystems.

[1]  L. Wackett,et al.  Optimization of trichloroethylene oxidation by methanotrophs and the use of a colorimetric assay to detect soluble methane monooxygenase activity , 1990, Biodegradation.

[2]  W. Evans,et al.  Oxidative metabolism of naphthalene by soil pseudomonads. The ring-fission mechanism. , 1964, The Biochemical journal.

[3]  S. Dagley.  Catabolism of aromatic compounds by micro-organisms. , 1971, Advances in microbial physiology.

[4]  J. Foght,et al.  Degradation of polycyclic aromatic hydrocarbons and aromatic heterocycles by a Pseudomonas species. , 1988, Canadian journal of microbiology.

[5]  T. Vogel,et al.  Transformation of toluene and benzene by mixed methanogenic cultures , 1987, Applied and environmental microbiology.

[6]  W. Campbell,et al.  Identification of a novel metabolite in phenanthrene metabolism by the fungus Cunninghamella elegans , 1989, Applied and environmental microbiology.

[7]  M. Trapido,et al.  [Monitoring of polycyclic aromatic hydrocarbons in the aquatic environment]. , 1987, Eksperimental'naia onkologiia.

[8]  E. Grund,et al.  Naphthalene degradation via salicylate and gentisate by Rhodococcus sp. strain B4 , 1992, Applied and environmental microbiology.

[9]  C. Cerniglia,et al.  Metabolism of naphthalene by cell extracts of Cunninghamella elegans. , 1978, Archives of biochemistry and biophysics.

[10]  H. Rehm,et al.  Biodegradation of phenanthrene by Arthrobacter polychromogenes isolated from a contaminated soil , 1991, Applied Microbiology and Biotechnology.

[11]  Mark R. Smith.  The biodegradation of aromatic hydrocarbons by bacteria , 2004, Biodegradation.

[12]  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.

[13]  C. Serdar,et al.  Genetics of naphthalene catabolism in pseudomonads. , 1988, Critical reviews in microbiology.

[14]  C. Cerniglia,et al.  Stereoselective formation of a K-region dihydrodiol from phenanthrene by Streptomyces flavovirens , 2004, Archives of Microbiology.

[15]  C. Cerniglia,et al.  Biodegradation of 1-nitropyrene , 1991, Archives of Microbiology.

[16]  C. Cerniglia,et al.  Polycyclic aromatic hydrocarbon degradation by a Mycobacterium sp. in microcosms containing sediment and water from a pristine ecosystem , 1989, Applied and environmental microbiology.

[17]  C. Cerniglia,et al.  Evidence for an arene oxide-NIH shift pathway in the transformation of naphthalene to 1-naphthol by Bacillus cereus , 1984, Archives of Microbiology.

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

[19]  E. A. Barnsley.  Bacterial Oxidation of Naphthalene and Phenanthrene , 1983, Journal of bacteriology.

[20]  D. Jerina,et al.  Absolute sterochemistry of the dihydroanthracene-cis- and -trans-1,2-diols produced from anthracene by mammals and bacteria. , 1975, Journal of the Chemical Society. Perkin transactions 1.

[21]  H. Dalton,et al.  Some properties of a soluble methane mono-oxygenase from Methylococcus capsulatus strain Bath. , 1976, The Biochemical journal.

[22]  H. Kiyohara,et al.  Degradation of Phenanthrene througho-Phthalate by anAeromonassp. , 1976 .

[23]  C. Cerniglia,et al.  Algal oxidation of aromatic hydrocarbons: formation of 1-naphthol from naphthalene by Agmenellum quadruplicatum, strain PR-6. , 1979, Biochemical and biophysical research communications.

[24]  D. Jerina,et al.  Initial reactions in the oxidation of naphthalene by Pseudomonas putida. , 1975, Biochemistry.

[25]  K. Hammel.  Organopollutant degradation by ligninolytic fungi , 1989 .

[26]  D. Warshawsky,et al.  Metabolism of benzo(a)pyrene by a dioxygenase enzyme system of the freshwater green alga Selenastrum capricornutum. , 1988, Biochemical and biophysical research communications.

[27]  D. Gibson,et al.  Aromatic hydrocarbon degradation: a molecular approach. , 1991, Genetic engineering.

[28]  C. Cerniglia,et al.  Studies on the Fungal Oxidation of Polycyclic Aromatic Hydrocarbons , 1980 .

[29]  C. Cerniglia,et al.  Fungal oxidation of benzo[a]pyrene and (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene. Evidence for the formation of a benzo[a]pyrene 7,8-diol-9,10-epoxide. , 1980, The Journal of biological chemistry.

[30]  C. Cerniglia,et al.  Microbial metabolism of pyrene. , 1986, Chemico-biological interactions.

[31]  D. Jerina,et al.  Monooxygenase activity in Cunninghamella bainieri: evidence for a fungal system similar to liver microsomes. , 1973, Archives of biochemistry and biophysics.

[32]  H. J. Rehm,et al.  Microbial metabolism of fluoranthene: isolation and identification of ring fission products , 2004, Applied Microbiology and Biotechnology.

[33]  D. Warshawsky,et al.  The phototoxicity of benzo[a]pyrene in the green alga Selenastrum capricornutum. , 1984, Environmental research.

[34]  E C Miller,et al.  Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules , 1981, Cancer.

[35]  C. Cerniglia,et al.  Naphthalene biodegradation in environmental microcosms: estimates of degradation rates and characterization of metabolites , 1987, Applied and environmental microbiology.

[36]  B. Ensley,et al.  Sequences of genes encoding naphthalene dioxygenase in Pseudomonas putida strains G7 and NCIB 9816-4. , 1993, Gene.

[37]  S. R. Wild,et al.  The persistence of polynuclear aromatic hydrocarbons (PAHs) in sewage sludge amended agricultural soils. , 1991, Environmental pollution.

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

[39]  Ikuo Watanabe,et al.  Microbial Degradation of Polycyclic Aromatic Hydrocarbons , 1994 .

[40]  S. E. Herbes,et al.  Microbial Transformation of Polycyclic Aromatic Hydrocarbons in Pristine and Petroleum-Contaminated Sediments , 1978, Applied and environmental microbiology.

[41]  C. Cerniglia,et al.  Stereoselective fungal metabolism of 7,12-dimethylbenz[a]anthracene: identification and enantiomeric resolution of a K-region dihydrodiol , 1987, Applied and environmental microbiology.

[42]  E. A. Barnsley.  Role and regulation of the ortho and meta pathways of catechol metabolism in pseudomonads metabolizing naphthalene and salicylate , 1976, Journal of bacteriology.

[43]  F. Tattersfield.  THE DECOMPOSITION OF NAPHTHALENE IN THE SOIL AND THE EFFECT UPON ITS INSECTICIDAL ACTION , 1928 .

[44]  J. Lalucat,et al.  New naphthalene-degrading marine Pseudomonas strains , 1988, Applied and environmental microbiology.

[45]  W. Lijinsky.  The formation and occurrence of polynuclear aromatic hydrocarbons associated with food. , 1991, Mutation research.

[46]  H. Wariishi,et al.  Extracellular peroxidases involved in lignin degradation by the white rot basidiomycete Phanerochaete chrysosporium , 1989 .

[47]  D. Capone,et al.  Effects of co-occurring aromatic hydrocarbons on degradation of individual polycyclic aromatic hydrocarbons in marine sediment slurries , 1988, Applied and environmental microbiology.

[48]  K. Yano,et al.  Phenanthrene-degrading phenotype of Alcaligenes faecalis AFK2 , 1982, Applied and environmental microbiology.

[49]  N. Walker,et al.  The metabolism of naphthalene by soil bacteria. , 1954, Journal of general microbiology.

[50]  J. Field,et al.  Biodegradation of polycyclic aromatic hydrocarbons by new isolates of white rot fungi , 1992, Applied and environmental microbiology.

[51]  M. Tien,et al.  Oxidation of persistent environmental pollutants by a white rot fungus. , 1985, Science.

[52]  William A. Telliard,et al.  PRIORITY POLLUTANTS I-A PERSPECTIVES VIEW , 1979 .

[53]  D. Capone,et al.  Degradation and Mineralization of the Polycyclic Aromatic Hydrocarbons Anthracene and Naphthalene in Intertidal Marine Sediments , 1985, Applied and environmental microbiology.

[54]  D. Jerina,et al.  Dihydrodiols from anthracene and phenanthrene. , 1976, Journal of the American Chemical Society.

[55]  C. Cerniglia,et al.  Fungal metabolism and detoxification of the nitropolycyclic aromatic hydrocarbon 1-nitropyrene , 1985, Applied and environmental microbiology.

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

[57]  J. Mihelcic,et al.  Microbial degradation of acenaphthene and naphthalene under denitrification conditions in soil-water systems , 1988, Applied and environmental microbiology.

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

[59]  G. C. Okpokwasili,et al.  Numerical taxonomy of phenanthrene-degrading bacteria isolated from the Chesapeake Bay , 1984, Applied and environmental microbiology.

[60]  H. Dalton,et al.  The soluble methane mono-oxygenase of Methylococcus capsulatus (Bath). Its ability to oxygenate n-alkanes, n-alkenes, ethers, and alicyclic, aromatic and heterocyclic compounds. , 1977, The Biochemical journal.

[61]  W. Karcher,et al.  Polycyclic aromatic compounds of environmental and occupational importance , 1986 .

[62]  M. Blumer,et al.  Polycyclic aromatic hydrocarbons in the environment: isolation and characterization by chromatography, visible, ultraviolet, and mass spectrometry. , 1974, Analytical chemistry.

[63]  Kevin C. Jones,et al.  ORGANIC CONTAMINANTS IN WELSH SOILS: POLYNUCLEAR AROMATIC HYDROCARBONS , 1989 .

[64]  R. Sims,et al.  Evidence for Cooxidation of Polynuclear Aromatic Hydrocarbons in Soil , 1989 .

[65]  M. Trower,et al.  Xenobiotic oxidation by cytochrome P-450-enriched extracts of Streptomyces griseus. , 1988, Biochemical and biophysical research communications.

[66]  I. C. Gunsalus,et al.  Plasmid gene organization: naphthalene/salicylate oxidation. , 1982, Proceedings of the National Academy of Sciences of the United States of America.

[67]  J. Means,et al.  Sorption of polynuclear aromatic hydrocarbons by sediments and soils. , 1980, Environmental science & technology.

[68]  B. Ensley,et al.  Naphthalene dioxygenase: purification and properties of a terminal oxygenase component , 1983, Journal of bacteriology.

[69]  K. Hammel,et al.  Ring fission of anthracene by a eukaryote. , 1991, Proceedings of the National Academy of Sciences of the United States of America.

[70]  C. Cerniglia,et al.  Fungal metabolism and detoxification of polycyclic aromatic hydrocarbons , 1985, Archives of Microbiology.

[71]  C. Cerniglia,et al.  Identification of xyloside conjugates formed from anthracene by Rhizoctonia solani , 1992 .

[72]  J. Mihelcic,et al.  Degradation of polycyclic aromatic hydrocarbon compounds under various redox conditions in soil-water systems , 1987, Applied and environmental microbiology.

[73]  P. Williams,et al.  The configuration of the 1,2-dihydroxy-1,2-dihydronaphthalene formed in the bacterial metabolism of naphthalene. , 1971, Biochimica et biophysica acta.

[74]  H. Rehm,et al.  Degradation of pyrene byRhodococcus sp. UW1 , 1991, Applied Microbiology and Biotechnology.

[75]  H. Kiyohara,et al.  The Catabolism of Phenanthrene and Naphthalene by Bacteria , 1978 .

[76]  M. Moen,et al.  Oxidative degradation of phenanthrene by the ligninolytic fungus Phanerochaete chrysosporium , 1992, Applied and environmental microbiology.

[77]  A. Johnson,et al.  The distribution of polycyclic aromatic hydrocarbons in the surficial sediments of Penobscot Bay (Maine, USA) in relation to possible sources and to other sites worldwide , 1985 .

[78]  C. Cerniglia,et al.  Identification of a Carboxylic Acid Metabolite from the Catabolism of Fluoranthene by a Mycobacterium sp , 1991, Applied and environmental microbiology.

[79]  H. Dalton,et al.  Resolution of the methane mono-oxygenase of Methylococcus capsulatus (Bath) into three components. Purification and properties of component C, a flavoprotein. , 1978, The Biochemical journal.

[80]  B. Golding,et al.  Oxidations of cyclopropane, methylcyclopropane, and arenes with the mono-oxygenase system from Methylococcus capsulatus , 1981 .

[81]  D. Warshawsky,et al.  Indigenous and enhanced mineralization of pyrene, benzo[a]pyrene, and carbazole in soils , 1991, Applied and environmental microbiology.

[82]  Kevin C. Jones,et al.  The long-term persistence of polynuclear aromatic hydrocarbons (PAHs) in an agricultural soil amended with metal-contaminated sewage sludges , 1991 .

[83]  J. Mueller,et al.  Action of a Fluoranthene-Utilizing Bacterial Community on Polycyclic Aromatic Hydrocarbon Components of Creosote , 1989, Applied and environmental microbiology.

[84]  G. E. Jones,et al.  Mineralization of phenanthrene by a Mycobacterium sp , 1988, Applied and environmental microbiology.

[85]  C. Cerniglia,et al.  The metabolism of fluoranthene by a species ofMycobacterium , 2005, Journal of Industrial Microbiology.

[86]  M. Alexander,et al.  Factors affecting the microbial degradation of phenanthrene in soil , 1991, Applied Microbiology and Biotechnology.

[87]  B. Ellis,et al.  Bioremediation of a creosote contaminated site , 1991 .

[88]  C. Cerniglia,et al.  Effects of chemical structure and exposure on the microbial degradation of polycyclic aromatic hydrocarbons in freshwater and estuarine ecosystems , 1987 .

[89]  W. Guerin,et al.  Estuarine ecology of phenanthrene-degrading bacteria , 1989 .

[90]  M. Narro,et al.  Evidence for an NIH shift in oxidation of naphthalene by the marine cyanobacterium Oscillatoria sp. strain JCM , 1992, Applied and environmental microbiology.

[91]  W. Campbell,et al.  Stereoselective fungal metabolism of methylated anthracenes , 1990, Applied and environmental microbiology.

[92]  P. Cane,et al.  The Plasmid-coded Metabolism of Naphthalene and 2-Methylnaphthalene in Pseudomonas Strains: Phenotypic Changes Correlated with Structural Modification of the Plasmid pWW60-1 , 1982 .

[93]  Timothy M. Vogel,et al.  Incorporation of Oxygen from Water into Toluene and Benzene during Anaerobic Fermentative Transformation , 1986, Applied and environmental microbiology.

[94]  M. Schell,et al.  Cloning and expression in Escherichia coli of the naphthalene degradation genes from plasmid NAH7 , 1983, Journal of bacteriology.

[95]  D. Warshawsky,et al.  Identification of the 11,12-dihydro-11,12-dihydroxybenzo(a)pyrene as a major metabolite produced by the green alga, Selenastrum capricornutum. , 1985, Biochemical and biophysical research communications.

[96]  D. Jerina,et al.  Oxidation of the carcinogens benzo [a] pyrene and benzo [a] anthracene to dihydrodiols by a bacterium. , 1975, Science.

[97]  C. Cerniglia,et al.  Stereoselective metabolism of anthracene and phenanthrene by the fungus Cunninghamella elegans , 1984, Applied and environmental microbiology.

[98]  S. Dagley.  A biochemical approach to some problems of environmental pollution. , 1975, Essays in biochemistry.

[99]  D. Dutta,et al.  Microsomal benzo(a)pyrene hydroxylase in Aspergillus ochraceus TS: assay and characterization of the enzyme system. , 1983, Biochemical and biophysical research communications.

[100]  D. Gibson,et al.  Purification and properties of ferredoxinNAP, a component of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816 , 1990, Journal of bacteriology.

[101]  D. Warshawsky,et al.  Conjugation of benzo[a]pyrene metabolites by freshwater green alga Selenastrum capricornutum. , 1990, Chemico-biological interactions.

[102]  C. Cerniglia,et al.  Fungal oxidation of (+/-)-9,10-dihydroxy-9,10-dihydrobenzo[a]pyrene: formation of diastereomeric benzo[a]pyrene 9,10-diol 7,8-epoxides. , 1980, Proceedings of the National Academy of Sciences of the United States of America.

[103]  C. Cerniglia,et al.  Microbial metabolism and detoxification of 7,12-dimethylbenz[a]anthracene , 1988, Journal of Industrial Microbiology.

[104]  C. Cerniglia,et al.  Regio- and stereo-selective metabolism of 4-methylbenz[a]anthracene by the fungus Cunninghamella elegans. , 1983, The Biochemical journal.

[105]  C. Cerniglia,et al.  Metabolism of aromatic hydrocarbons by yeasts , 1981, Archives of Microbiology.

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

[107]  C. Cerniglia,et al.  Fungal transformation of fluoranthene , 1990, Applied and environmental microbiology.

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

[109]  C. Cerniglia,et al.  Identification of metabolites from degradation of naphthalene by a Mycobacterium sp. , 2004, Biodegradation.

[110]  C. Cerniglia,et al.  Metabolism of Naphthalene by the Cyanobacterium Oscillatoria sp., Strain JCM , 1980 .

[111]  D. Gibson,et al.  Purification and Propeties of (+)-cis-Naphthalene Dihydrodiol Dehydrogenase of Pseudomonas putida , 1974, Journal of bacteriology.

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

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

[114]  C. Cerniglia,et al.  Oxidation of Naphthalene by Cyanobacteria and Microalgae , 1980 .

[115]  K. Yano,et al.  Characterization of a phenanthrene degradation plasmid from Alcaligenes faecalis AFK2 , 1990 .

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

[117]  R. Sims,et al.  Approach to bioremediation of contaminated soil. , 1990 .

[118]  R. Hites,et al.  Sedimentary Polycyclic Aromatic Hydrocarbons: The Historical Record , 1977, Science.

[119]  P. Gschwend,et al.  Fluxes of polycyclic aromatic hydrocarbons to marine and lacustrine sediments in the northeastern United States , 1981 .

[120]  S. Aust.  Degradation of environmental pollutants byPhanerochaete chrysosporium , 1990, Microbial Ecology.

[121]  D. Jerina,et al.  ABSOLUTE STEREOCHEMISTRY OF THE DIHYDROANTHRACENE-CIS- AND -TRANS-1,2-DIOLS PRODUCED FROM ANTHRACENE BY MAMMALS AND BACTERIA , 1976 .

[122]  R. Hites,et al.  Polycyclic Aromatic Hydrocarbons in Marine/Aquatic Sediments: Their Ubiquity , 1980 .

[123]  William J. Doucette,et al.  Fate of PAH compounds in two soil types: influence of volatilization, abiotic loss and biological activity. , 1990 .

[124]  M. Leisola,et al.  Role of extracellular ligninases in biodegradation of benzo(a)pyrene by Phanerochaete chrysosporium , 1986 .

[125]  D. Capone,et al.  Degradation andMineralization ofthePolycyclic Aromatic Hydrocarbons Anthracene andNaphthalene inIntertidal Marine Sedimentst , 1985 .

[126]  A. Dipple,et al.  Polycyclic aromatic hydrocarbon carcinogens. , 1990, Progress in clinical and biological research.

[127]  M. Leisola,et al.  Oxidation of benzo(a)pyrene by extracellular ligninases of Phanerochaete chrysosporium. Veratryl alcohol and stability of ligninase. , 1986, The Journal of biological chemistry.

[128]  C. Cerniglia,et al.  Metabolism of phenanthrene by Phanerochaete chrysosporium , 1991, Applied and environmental microbiology.

[129]  N. Truffaut,et al.  Preliminary study on relationships among strains forming a bacterial community selected on naphthalene from a marine sediment. , 1990, Canadian journal of microbiology.

[130]  A. Stolz,et al.  Metabolism of naphthalene by the biphenyl-degrading bacterium Pseudomonas paucimobilis Q1 , 2004, Biodegradation.

[131]  C. Serdar,et al.  Studies of nucleotide sequence homology between naphthalene-utilizing strains of bacteria. , 1989, Biochemical and biophysical research communications.

[132]  A. Boronin,et al.  INCOMPATIBILITY GROUPS OF NAPHTHALENE DEGRADATIVE PLASMIDS IN PSEUDOMONAS , 1980 .

[133]  M. Shiaris.  Phenanthrene mineralization along a natural salinity gradient in an Urban Estuary, Boston Harbor, Massachusetts , 1989, Microbial Ecology.

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

[135]  B. Kalyanaraman,et al.  Oxidation of polycyclic aromatic hydrocarbons and dibenzo[p]-dioxins by Phanerochaete chrysosporium ligninase. , 1986, The Journal of biological chemistry.

[136]  C. Cerniglia,et al.  Fungal oxidation of benzo[a]pyrene: formation of (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene by Cunninghamella elegans. , 1980, Biochemical and biophysical research communications.

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

[138]  J. Rosazza,et al.  Microbial models of mammalian metabolism. , 1975, Journal of natural products.

[139]  C. Cerniglia.  Initial Reactions in the Oxidation of Anthracene by Cunninghamella elegans , 1982 .

[140]  E. A. Barnsley,et al.  Naphthalene plasmids in pseudomonads , 1982, Journal of bacteriology.

[141]  C. Cerniglia,et al.  Mineralization of polycyclic aromatic hydrocarbons by a bacterium isolated from sediment below an oil field , 1988, Applied and environmental microbiology.

[142]  R. Hébert,et al.  Fungal transformation of naphthalene , 1978, Archives of Microbiology.

[143]  C. Cerniglia,et al.  Oxidation of benzo[a]pyrene by the filamentous fungus Cunninghamella elegans. , 1979, The Journal of biological chemistry.

[144]  M. Alexander,et al.  Effect of surfactants at low concentrations on the desorption and biodegradation of sorbed aromatic compounds in soil , 1991 .

[145]  C. Cerniglia,et al.  Fungal metabolism and detoxification of fluoranthene , 1992, Applied and environmental microbiology.

[146]  R. Bartha,et al.  Effect of bioremediation on polycyclic aromatic hydrocarbon residues in soil , 1990 .

[147]  C. Cerniglia,et al.  Fungal metabolism of aromatic hydrocarbons. , 1992 .

[148]  B. Ensley,et al.  Oxidation of naphthalene by a multicomponent enzyme system from Pseudomonas sp. strain NCIB 9816 , 1982, Journal of bacteriology.

[149]  H. Holland,et al.  Biotransformation of polycyclic aromatic compounds by fungi. , 1986, Xenobiotica; the fate of foreign compounds in biological systems.

[150]  J. Sutherland,et al.  Detoxification of polycyclic aromatic hydrocarbons by fungi , 2005, Journal of Industrial Microbiology.

[151]  D. Gibson,et al.  Purification and properties of NADH-ferredoxinNAP reductase, a component of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816 , 1990, Journal of bacteriology.

[152]  C. Cerniglia,et al.  Fungal metabolism of acenaphthene by Cunninghamella elegans , 1992, Applied and environmental microbiology.

[153]  C. Cerniglia,et al.  Metabolism of naphthalene by Cunninghamella elegans , 1977, Applied and environmental microbiology.

[154]  C. Cerniglia,et al.  Naphthalene Metabolism by Diatoms Isolated from the Kachemak Bay Region of Alaska , 1982 .

[155]  D. Ghosh,et al.  Oxidation of phenanthrene by a strain ofMicrococcus: Evidence of protocatechuate pathway , 1983, Current Microbiology.

[156]  N. Dunn,et al.  Transmissible Plasmid Coding Early Enzymes of Naphthalene Oxidation in Pseudomonas putida , 1973, Journal of bacteriology.

[157]  D T Gibson,et al.  Oxidative degradation of aromatic hydrocarbons by microorganisms. I. Enzymatic formation of catechol from benzene. , 1968, Biochemistry.

[158]  A. Boronin.  Genetics of biodegradation , 1991 .

[159]  M. Narro,et al.  Metabolism of phenanthrene by the marine cyanobacterium Agmenellum quadruplicatum PR-6 , 1992, Applied and environmental microbiology.

[160]  R. J. Watkinson,et al.  Comparison of abilities of white-rot fungi to mineralize selected xenobiotic compounds , 1991, Applied Microbiology and Biotechnology.

[161]  J. Rosazza,et al.  Microbial models of mammalian metabolism. Aromatic hydroxylation. , 1974, Archives of biochemistry and biophysics.

[162]  R. D. Dua,et al.  Purification and characterisation of naphthalene oxygenase from Corynebacterium renale. , 1981, European journal of biochemistry.

[163]  C. Cerniglia,et al.  Stereochemistry and evidence for an arene oxide-NIH shift pathway in the fungal metabolism of naphthalene. , 1983, Chemico-biological interactions.