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

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

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

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

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

[6]  J. L. Zajicek,et al.  Use of semipermeable membrane devices for in situ monitoring of polycyclic aromatic hydrocarbons in aquatic environments , 1992 .

[7]  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.

[8]  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.

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

[10]  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.

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

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

[13]  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.

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

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

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

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

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

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

[20]  C. Cerniglia,et al.  Identification of metabolites from the degradation of fluoranthene by Mycobacterium sp. strain PYR-1 , 1993, Applied and environmental microbiology.

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

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

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

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

[25]  H. Kiyohara,et al.  Degradation of Phenanthrene through o-Phthalate by an Aeromonas sp. , 1976 .

[26]  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.

[27]  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.

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

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

[30]  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.

[31]  Y. Tsai,et al.  Rapid Method for Direct Extraction of mRNA from Seeded Soils , 1991, Applied and environmental microbiology.

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

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

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

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

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

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

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

[39]  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 .

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

[41]  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.

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

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

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

[45]  R. Efroymson,et al.  Biodegradation by an Arthrobacter Species of Hydrocarbons Partitioned into an Organic Solvent , 1991, Applied and environmental microbiology.

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

[47]  C. Batt,et al.  Polymerase chain reaction amplification of naphthalene-catabolic and 16S rRNA gene sequences from indigenous sediment bacteria , 1993, Applied and environmental microbiology.

[48]  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.

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

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

[51]  H. Kiyohara,et al.  Rapid Screen for Bacteria Degrading Water-Insoluble, Solid Hydrocarbons on Agar Plates , 1982, Applied and environmental microbiology.

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

[53]  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.

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

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

[56]  M. Alexander,et al.  Surfactants at low concentrations stimulate biodegradation of sorbed hydrocarbons in samples of aquifer sands and soil slurries , 1992 .

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

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

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

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

[61]  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.

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

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

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

[65]  J. Bayona,et al.  Isolation and characterization of a fluorene-degrading bacterium: identification of ring oxidation and ring fission products , 1992, Applied and environmental microbiology.

[66]  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.

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

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

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

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

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

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

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

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

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

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

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

[78]  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.

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

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

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

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

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

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

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

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

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

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

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

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

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

[94]  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 .

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

[96]  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.

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

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

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

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

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

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

[103]  Gary S. Sayler,et al.  Specific and Quantitative Assessment of Naphthalene and Salicylate Bioavailability by Using a Bioluminescent Catabolic Reporter Bacterium , 1992, Applied and environmental microbiology.

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

[105]  M. Overcash,et al.  Fate of polynuclear aromatic compounds (PNAs) in soil-plant systems , 1983 .

[106]  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.

[107]  J. Mueller,et al.  Biodegradation of creosote and pentachlorophenol in contaminated groundwater: chemical and biological assessment , 1991, Applied and environmental microbiology.

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

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

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

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

[112]  A. Bogardt,et al.  Enumeration of phenanthrene-degrading bacteria by an overlayer technique and its use in evaluation of petroleum-contaminated sites , 1992, Applied and environmental microbiology.

[113]  P. Chapman,et al.  Bacterial metabolism of naphthalene: construction and use of recombinant bacteria to study ring cleavage of 1,2-dihydroxynaphthalene and subsequent reactions , 1992, Journal of bacteriology.

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

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

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

[117]  M. Shiaris Seasonal Biotransformation of Naphthalene, Phenanthrene, and Benzo[a]pyrene in Surficial Estuarine Sediments , 1989, Applied and environmental microbiology.

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

[119]  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.

[120]  G S Sayler,et al.  Environmental application of nucleic acid hybridization. , 1990, Annual review of microbiology.

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

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

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

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

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

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

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

[128]  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.

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

[130]  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.

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

[132]  T. Omori,et al.  Microbial degradation of dibenzofuran, fluorene, and dibenzo-p-dioxin by Staphylococcus auriculans DBF63 , 1993, Applied and environmental microbiology.

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

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

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

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

[137]  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 .

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

[139]  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.

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

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

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

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

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

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

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

[147]  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.

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

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

[150]  G. Sayler,et al.  Rapid, Sensitive Bioluminescent Reporter Technology for Naphthalene Exposure and Biodegradation , 1990, Science.

[151]  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.

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

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

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

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