Part of the book series: Environment & Chemistry ((ENVC,volume 2))

Abstract

The polycyclic aromatic hydrocarbons (PAHs) with two fused aromatic rings discussed in this chapter are naphthalene, acenaphthalene, acenaphthylene, and fluorene. These small PAHs are produced by pyrolysis of fossil fuels and also are frequent constituents of coal tar, oil products, tobacco smoke, automobile exhaust gas, incinerated waste, industrial effluents, and urban air (Grifoll et al., 1994; Pothuluri et al., 1993) . Naphthalene and acenaphthene are used for the industrial production of pesticides, paints and dyes.

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References

  • Acton, D. W., and J.F. Barker. 1992. In situ biodegradation potential of aromatic hydrocarbons in anaerobic groundwaters. J. Contam. Hydrol. 9:325–352.

    Article  CAS  Google Scholar 

  • Alleman, B.C., R.E. Hinchee, R.C. Brenner, and P.T. McCauley. 1995. Bioventing PAH contamination at the Reilly tar site. In: In situ aeration: Air sparging, bioventing, and related remediation processes (Edited by R.E. Hinchee, R.N. Miller, and P.C. Johnson). Book 3(2) of the third international in situ and on–site bioreclamation symposium (San Diego, USA). Battelle Press, Columbus, USA.

    Google Scholar 

  • Allen, P.G., D.S. Francy, K.L. Duston, J.M. Thomas, and C.H. Ward. 1992. Biosurfactant production and emulsification capacity of subsurface microorganisms. In: Soil decontamination using biological processes. Schön and Wetzel, Germany.

    Google Scholar 

  • Ashok, B.T., and S. Saxena. 1995. Biodegradation of polycyclic aromatic hydrocarbons – A review . J. Sci. Ind . Res. 54 : 442–451.

    Google Scholar 

  • Barclay, C.D., G.F. Farquhar, and R.L. Legge. 1995. Biodegradation and sorption of polycyclic hydrocarbons by Phanerochaete chrysosporium. Appl. Microbiol. Biotechnol. 42:958–963

    Article  CAS  Google Scholar 

  • Barr, D.P., and S.D. Aust. 1994. Mechanisms white rot fungi use to degrade pollutants. Environ. Sci. Technol. 28:78–87.

    Google Scholar 

  • Barnsley, E.A. 1983. Phthalate pathway of phenanthrene metabolism: Formation of 2’–carboxybenzalpyruvate. J. Bacteriol. 154:113–117.

    CAS  Google Scholar 

  • Bauer, J.E., and D.G. Capone. 1985. Degradation and mineralization of the polycyclic aromatic hydrocarbons anthracene and naphthalene in intertidal marine sediments. Appl. Environ. Microbiol. 50:81–90.

    CAS  Google Scholar 

  • Bauer, J.E., and D.G. Capone. 1988. Effects of co–occurring aromatic hydrocarbons on degradation of individual polycyclic aromatic hydrocarbons in marine sediment slurries. Appl. Environ. Microbiol. 54:1649–1655.

    CAS  Google Scholar 

  • Berends, J., and D. Kloeg. 1986. Landfarming van met PAKs, minerale olie of koolwaterstoffen verontreinigde grond. In: Syllabus Symposium Biologische Grondreiniging, d.d. 27 november 1986 te Rotterdam. NIRIA, Den Haag, The Netherlands.

    Google Scholar 

  • Bezalel, L. , Y. Hadar, and C. E. Cerniglia. 1996a. Mineralization of polycyclic aromatic hydrocarbons by the white rot fungus Pleurotus ostreatus. Appl. Environ. Microbiol. 62:292–295.

    CAS  Google Scholar 

  • Bezalel, L., Y. Hadar, P.P. Fu, J.P. Freeman, and C.E. Cerniglia. 1996b. Metabolism of phenanthrene by the white rot fungus Pleurotus ostreatus. Appl. Environ. Microbiol. 62:2547–2553.

    CAS  Google Scholar 

  • Bezalel, L. , Y. Hadar, P. P. Fu, J.P. Freeman, and C. E. Cerniglia. 1996c. Initial oxidation products in the metabolism of pyrene, anthracene, and dibenzothiophene by the white rot fungus Pleurotus ostreatus. Appl. Environ. Microbiol. 62:2554–2559.

    CAS  Google Scholar 

  • Boldrin, B., A. Tiehm, and C. Fritzsche. 1993. Degradation of phenanthrene, fluorene, fluoranthene, and pyrene by a Mycobacterium sp. Appl. Environ. Microbiol. 59:1927–1930.

    CAS  Google Scholar 

  • Bossert, I. D., and R. Bartha. 1986. Structure–biodegradability relationships of polycyclic aromatic hydrocarbons in soil. Bull. Environ. Contam. Toxicol. 37:490–495.

    Article  CAS  Google Scholar 

  • Bossert, I., W.M. Kachel, and R. Bartha. 1984. Fate of hydrocarbons during oily sludge disposal in soil. Appl. Environ. Microbiol. 47:763– 767.

    CAS  Google Scholar 

  • Bouchez, M., D. Blanchet, and J.-P. Vandecasteele. 1995a. Degradation of polycyclic aromatic hydrocarbons by pure strains and defined strain associations: Inhibition phenomena and cometabolism. Appl. Microbiol. Biotechnol. 43:156–164.

    Article  CAS  Google Scholar 

  • Bouchez, M., D. Blanchet, B. Besnaïnou, and J.-P. Vandecasteele. 1995b. Diversity of metabolic capacities among strains degrading polycyclic aromatic hydrocarbons (PAHs). In: Microbial processes for bioremediation (Edited by R.E. Hinchee, C.M. Vogel, and F.J. Brockman). Book 3(8) of the third international in situ and on–site bioreclamation symposium, San Diego, California, USA. Battelle Press, Columbus, USA.

    Google Scholar 

  • Bouwer, E.J., N. Durant, L. Wilson, W. Zhang, and A. Cunningham. 1994. Degradation of xenobiotic compounds in situ: Capabilities and limits. FEMS Microbiol. Rev. 15:307–317.

    Article  CAS  Google Scholar 

  • Brodkorb, T. S. , and R.L. Legge. 1992. Enhanced biodegradation of phenanthrene in oil tarcontaminated soils supplemented with Phanerochaete chrysosporium. Appl. Environ. Microbiol. 58 : 3117–3121.

    CAS  Google Scholar 

  • Bryniok, D., W. Brunner, B. Eichler, A. Köhler, K. Mackenbrock, and H.-J . Knackmuss. 1992. Biodegradation of PAH in airlift-bioreactors. In: Soil decontamination using biological processes. Schön and Wetzel, Germany.

    Google Scholar 

  • Bumpus, J.A., M. Tien, D. Wright, and S.D. Aust. 1985. Oxidation of persistent environmental pollutants by a white rot fungus. Science 228:1434–1436.

    Article  CAS  Google Scholar 

  • Bumpus, J.A. 1989. Biodegradation of polycyclic aromatic hydrocarbons by Phanerochaete chrysosporium. Appl. Environ. Microbiol. 55:154–158.

    CAS  Google Scholar 

  • Callahan, M.A., M.W. Slimak, N.W. Gabel, I.P. May, C.F. Fowler, J. Randall Freed, P. Jennings, R.L. Durfee, F.C. Whitmore, B.M. Maestri, W.R. Mabey, B. R. Holt, and C. Gould. 1979. Water–related environmental fate of 129 priority pollutants. EPA4401479–029(a and b), NTIS (report no. 13.065, vol. 2.), USA.

    Google Scholar 

  • Casellas M., M. Grifoll, J.M. Bayona, and A.M. Solanas. 1997. New metabolites in the degradation of fluorene by Arthrobacter sp. strain F101. Appl. Environ. Microbiol. 63:819–826.

    CAS  Google Scholar 

  • Castaldi, F.J. 1994. Slurry bioremediation of polycyclic aromatic hydrocarbons in soil wash concentrates. In: Applied biotechnology for site remediation (Edited by R. E. Hinchee, D. B. Anderson, F. Blaine Metting (jr.), and G.D. Sayles). CRC Press, New York, USA.

    Google Scholar 

  • Cerniglia, C.E., R.L. Herbert, P.J. Stanizlo, and D.T. Gibson. 1978. Fungal transformation of naphthalene. Arch. Microbiol. 117 :135–143.

    Article  CAS  Google Scholar 

  • Cerniglia, C.E., R.H. Dodge, and D.T. Gibson. 1980. Studies on the fungal oxidation of polycyclic aromatic hydrocarbons. Botanica Marina 23 :121–124.

    Article  CAS  Google Scholar 

  • Cerniglia, C.E. 1984. Microbial metabolism of polycyclic aromatic hydrocarbons. Adv. Appl. Microbiol. 30:31–71.

    Article  CAS  Google Scholar 

  • Cerniglia, C.E., and S.K. Yang. 1984. Stereoselective metabolism of anthracene and phenanthrene by the fungus Cunninghamella elegans. Appl. Environ. Microbiol. 47:119–124.

    CAS  Google Scholar 

  • Cerniglia, C.E., G.L. White, and R.H. Heflich. 1985. Fungal metabolism and detoxification of polycyclic aromatic hydrocarbons. Arch. Microbiol. 143:105–110.

    Article  CAS  Google Scholar 

  • Cerniglia, C.E. 1986. Microbial metabolism of pyrene. Chem.Biol. Interactions 57:203–216.

    Article  CAS  Google Scholar 

  • Cerniglia, C.E., W.L. Campbell, J.P. Freeman, and F.E. Evans. 1989. Identification of a novel metabolite in phenanthrene metabolism by the fungus Cunninghamella elegans. Appl. Environ. Microbiol. 55:2275–2279.

    CAS  Google Scholar 

  • Cerniglia, C.E., and M.A. Heitkamp. 1989. Microbial degradation of polycyclic aromatic hydrocarbons (PAH) in the aquatic environment. In: Metabolism of polycyclic aromatic hydrocarbons in the aquatic environment (Edited by U. Varanasi). CRC Press, New York, USA.

    Google Scholar 

  • Cerniglia, C.E. 1992. Biodegradation of polycyclic aromatic hydrocarbons. Biodegradation 3:351–368.

    Article  CAS  Google Scholar 

  • Cerniglia, C. E., J.B. Sutherland, and S. A. Crow. 1992. Fungal metabolism of aromatic hydrocarbons. In: Microbial degradation of natural products (Edited by G. Winkelmann). VCH Verlagsgesellschaft, Wiesbaden, Germany.

    Google Scholar 

  • Cerniglia, C.E. 1993. Biodegradation of polycyclic aromatic hydrocarbons. Current Opinion in Biotechnology 4:331–338.

    Article  CAS  Google Scholar 

  • Cerniglia, C.E., D.T. Gibson, and R.H. Dodge. 1994. Metabolism of benz[a]anthracene by the filamentous fungus Cumminghamella elegans. Appl. Environ. Microbiol. 60:3931–3938.

    CAS  Google Scholar 

  • Coover, M. P. , and R.C. Sims. 1987. The effect of temperature on polycyclic aromatic hydrocarbon persistence in an unacclimated soil. Hazard. Waste Hazard. Mater. 4:69–82.

    Article  CAS  Google Scholar 

  • Davies, J. I. , and W.C. Evans. 1964. Oxidative metabolism of naphthalene by soil Pseudomonads. Biochem. J. 91:251–261.

    CAS  Google Scholar 

  • Dhawale, S. W., S.S. Dhawale, and D. Dean-Ross. 1992. Degradation of phenanthrene by Phanerochaete chrysosporium occurs under ligninolytic as well as nonligninolytic conditions. Appl. Environ. Microbiol. 58:3000–3006.

    CAS  Google Scholar 

  • Efroymson, R.A., and M. Alexander. 1991. Biodegradation by an Arthrobacter species of hydrocarbons partitioned into an organic solvent. Appl. Environ. Microbiol. 57:1441–1447.

    CAS  Google Scholar 

  • Efroymson, R.A., and M. Alexander. 1994. Role of partioning in biodegradation of phenanthrene dissolved in nonaqueous–phase liquids. Environ. Sci. Technol. 28:1172–1179.

    Article  CAS  Google Scholar 

  • Ehrlich, G.G., D.F. Goerlitz, E.M. Godsy, and M.F. Hult. 1982. Degradation of phenolic contaminants in ground water by anaerobic bacteria: St. Louis Park, Minnesota. Ground Water 20:703–710.

    Article  CAS  Google Scholar 

  • Engesser, K.H., V. Strubel, K. Christoglou, P. Fischer, and H.G. Rast. 1989. Dioxygenolytic cleavage of aryl ether bonds: 1,10–Dihydro–1,10–dihydroxyfluorene–9–one, a novel arene dihydrodiol as evidence for angular dioxygenation of dibenzofuran. FEMS Microbiol. Lett. 65:205–210.

    Article  CAS  Google Scholar 

  • Evans, W.C., H.N. Fernley, and E. Griffiths. 1965. Oxidative metabolism of phenanthrene and anthracene by soil pseudomonads: The ring fission mechanism. Biochem. J. 95:97–103.

    Google Scholar 

  • Field, J.A., E. de Jong, G. Feijoo-Costa, and J.A.M. de Bont. 1992. Biodegradation of polycyclic aromatic hydrocarbons by new isolates of white rot fungi. Appl. Environ. Microbiol. 58:2219–2226.

    CAS  Google Scholar 

  • Field, J.A., E. de Jong, G. Feijoo-Costa, and J.A.M. de Bont. 1993a. Screening for ligninolytic fungi applicable to the biodegradation of xenobiotics. TIBTECH 11:44–49.

    Article  CAS  Google Scholar 

  • Field, J.A., J.T.C. Grotenhuis, E. de Jong, G. Feijoo-Costa, E. Hessels, W. Rulkens, R. Wijngaarde, and J.A.M. de Bont. 1993b. Screening for PAH-degrading white rot fungi: Bjerkandera sp. BOS55, a promising new isolate. In: Integrated soil and sediment research: A basis for proper protection (Edited by H.J.P. Eijsackers and T. Hamers). Kluwer Academic Publishers, The Netherlands.

    Google Scholar 

  • Foght, J. M., and D. W. S. Westlake. 1988. Degradation of polycyclic aromatic hydrocarbons and aromatic hetrocycles by a Pseudomonas species. Can. J. Microbiol. 34:1135–1141.

    Article  CAS  Google Scholar 

  • Fritzsche, C. 1994. Degradation of pyrene at low defined oxygen concentrations by a Mycobacterium sp. Appl. Environ. Microbiol. 60:1687–1689.

    CAS  Google Scholar 

  • Furukawa, K., J.R. Simon, and A.M. Chakrabarty. 1983. Common induction and regulation of biphenyl, xylene/toluene and salicylate catabolism in Pseudomonas paucimobilus. J. Bacteriol. 154:1356–1362.

    CAS  Google Scholar 

  • George, E.J., and R.D. Neufeld. 1989. Degradation of fluorene in soil by fungus Phanerochaete chrysosporium. Biotechnol. Bioeng. 33 :1306–1310.

    Article  CAS  Google Scholar 

  • Gibson, D.T. 1982. Microbial degradation of hydrocarbons. Toxicol. Environ. Chem. 5:237–250.

    Article  CAS  Google Scholar 

  • Gibson, D. T., V. Mahadevan, D.M. Jerina, H. Yagi, and H. J. C. Yeh. 1975. Oxidation of the carcinogens benzo[a]pyrene and benz[a]anthracene to dihydrodiols by a bacterium. Science 189:295– 297.

    Article  CAS  Google Scholar 

  • Gray, M.R., D.K. Banerjee, P.M. Fedorak, A. Hashimoto, J.H. Masliyah, and M.A. Pickard. 1994. Biological remediation of anthracene–contaminated soil in rotating bioreactors. Appl. Microbiol. Biotechnol. 40:933–940.

    Article  CAS  Google Scholar 

  • Grifoll, M., M. Casellas, and A.M. Solanas. 1992. Isolation and characterization of a fluorenedegrading bacterium: Identification of ring oxidation and ring fission products. Appl. Environ. Microbiol. 58:2910–2917.

    CAS  Google Scholar 

  • Grifoll, M., S.A. Selifonov, and P.J. Chapman. 1994. Evidence for a novel pathway in the degradation of fluorene by Pseudomonas sp. strain F274. Appl. Environ. Microbiol. 60:2438–2449.

    CAS  Google Scholar 

  • Grifoll, M., S.A. Selifonov, C.V. Gatlin, and P.J. Chapman. 1995. Actions of a versatile fluorene–degrading bacterial isolate on polycyclic aromatic compounds. Appl. Environ. Microbiol. 61: 3711–3723.

    CAS  Google Scholar 

  • Grosser, R.J., D. Warshawsky, and J.R. Vestal. 1991. Indigenous and enhanced mineralization of pyrene, benzo[a]pyrene, and carbazole in soils. Appl. Environ. Microbiol. 57:3462–3469.

    CAS  Google Scholar 

  • Grund, E., B. Denecke, and R. Eichenlaub. 1992. Naphthalene degradation via salicylate and gentisate by Rhodococcus sp. strain B4. Appl. Environ. Microbiol. 58:1874–1877.

    CAS  Google Scholar 

  • Guerin, W. F., and G.E. Jones. 1988a. Two–stage mineralization of phenanthrene by estuarine enrichment cultures. Appl. Environ. Microbiol. 54:929–936.

    CAS  Google Scholar 

  • Guerin, W.F., and G.E. Jones. 1988b. Mineralization of phenanthrene by a Mycobacterium sp. Appl. Environ. Microbiol. 54:937–944.

    CAS  Google Scholar 

  • Haemmerli, S.D., M.S.A. Leisola, D. Sanglard, and A. Fiechter. 1986. Oxidation of benzo[a]pyrene by extracellular ligninase of Phanerochaete chrysosporium. J. Biol. Chem. 261:6900–6903.

    CAS  Google Scholar 

  • Hammel, K.E., B. Kalyanaraman, and T.K. Kirk. 1986. Oxidation of PAHs and dibenzo[p]dioxins by Phanerochaete chrysosporium lignase. J. Biol. Chem. 261:16948–16952.

    CAS  Google Scholar 

  • Hammel, K. E., B. Green, and W. Z. Gai. 1991. Ring fission of anthracene by an eukaryote. Proc. Natl. Acad. Sci. USA 88:10605–10608.

    Article  CAS  Google Scholar 

  • Hammel, K. E. , W. Z. Gai, B. Green, and M. A. Moen. 1992. Oxidative degradation of phenanthrene by the ligninolytic fungus Phanerochaete chrysosporium. Appl. Environ. Microbiol. 58:1832–1838.

    CAS  Google Scholar 

  • Heitkamp, M.A., and C.E. Cerniglia. 1988. Mineralization of polycyclic aromatic hydrocarbons by a bacterium isolated from sediment below an oil field. Appl. Environ. Microbiol. 54:1612–1614.

    CAS  Google Scholar 

  • Heitkamp, M.A., J.P. Freeman, D.W. Miller, and C.E. Cerniglia. 1988a. Pyrene degradation by a Mycobacterium sp.: Identification of ring oxidation and ring fission products. Appl. Environ. Microbiol. 54:2556–2565.

    CAS  Google Scholar 

  • Heitkamp, M.A., W. Franklin, and C.E. Cerniglia. 1988b. Microbial metabolism of polycyclic aromatic hydrocarbons: Isolation and characterization of a pyrene–degrading bacterium. Appl. Environ. Microbiol. 54:2549–2555.

    CAS  Google Scholar 

  • Heitkamp, M.A., and C.E. Cerniglia. 1989. Polycyclic aromatic hydrocarbon degradation by a Mycobacterium sp. in microcosms containing sediment and water from pristine ecosystem. Appl. Environ. Microbiol. 55:1968–1973.

    CAS  Google Scholar 

  • Herbes, S.E., and L.R. Schwall. 1978. Microbial transformations of polycyclic aromatic hydrocarbons in pristine and petroleum–contaminated sediments. Appl. Environ. Microbiol. 35:306–316.

    CAS  Google Scholar 

  • Hinchee R.E., R.N. Miller, and P.C. Johnson. 1995. In situ aeration: Air sparging, bioventing, and related remediation processes. Book 3(2) of the third international in situ and on–site bioreclamation symposium, San Diego, USA. Battelle Press, Columbus, USA.

    Google Scholar 

  • Hofmann, K.H. 1986. Oxidation of naphthalene by Saccharomyces cerevisiae and Candida utilis. J. Basic Microbiol. 26:109–111.

    Article  CAS  Google Scholar 

  • Huisin’t Veld M. G. A., J. Werners, H. J. Doddema, and H. J. van Veen. 1995. Biological PAHdegradation in dredged sediments. In: Bioremediation of recalcitrant organics (Edited by R. E. Hinchee, R. E. Hoeppel, and D. A. Anderson). Book 3(7) of the third international in situ and on–site bioreclamation symposium, San Diego, California, USA. Battelle Press, Columbus, USA.

    Google Scholar 

  • Jensen, B., E. Arvin, and A.T. Gundersen. 1985. The degradation of aromatic hydrocarbons with bacteria from oil contaminated aquifers. NWWA/API Conf., Nov. 13–15, 1985, Houston, U.S.A.

    Google Scholar 

  • Jerina, D.M., H. Selander, H. Yagi, M.C. Wells, J.F. Davey, V. Mahadevan, and D.T. Gibson. 1976. Dihydrodiols from anthracene and phenanthrene. J. Am. Chem. Soc. 98:5988–5996.

    Article  CAS  Google Scholar 

  • Kappeler, T. , and K. Wuhrmann. 1978. Microbial degradation of the water–soluble fraction of gasoil–II, bioassays with pure strains. Water Res. 12:335–342.

    Article  CAS  Google Scholar 

  • Keck, J., R.C. Sims, M. Coover, K. Park, and B. Symons. 1989. Evidence for cooxidation of polynuclear aromatic hydrocarbons in soil. Water Res. 23:1467–1476.

    Article  CAS  Google Scholar 

  • Kelley, I. , J.P. Freeman, and C. E. Cerniglia. 1990. Identification of metabolites from degradation of naphthalene by a Mycobacterium sp. Biodegradation 1:283–290.

    Article  CAS  Google Scholar 

  • Kelley, I., and C.E. Cerniglia. 1991. The metabolism of fluoranthene by a species of Mycobacterium. J. Ind. Microbiol. 7:19–26.

    Article  CAS  Google Scholar 

  • Kelley, I., J.P. Freeman, F.E. Evans, and C.E. Cerniglia. 1991. Identification of a carboxylic acid metabolite from the catabolism of fluoranthene by a Mycobacterium sp. Appl. Environ. Microbiol. 57 : 636–641.

    CAS  Google Scholar 

  • Kelley, I., J.P. Freeman, F.E. Evans, and C.E. Cerniglia. 1993. Identification of metabolites from the degradation of fluoranthene by a Mycobacterium sp. strain PYR–1. Appl. Environ. Microbiol. 59 : 800–806 .

    CAS  Google Scholar 

  • Keuth, S., and H.-J. Rehm. 1991. Biodegradation of phenanthrene by Arthrobacter polychromogenes isolated from a contaminated soil. Appl. Microbiol. Biotechnol. 34:804–808.

    Article  CAS  Google Scholar 

  • Kincannon, D.F., A. Weinert, R. Padorr, and E.L. Stover. 1983. Predicting treatability of multiple organic priority pollutant waste waters from single–pollutant treatability studies. Proc. Ind. Waste Conf. 37 : 641–650.

    Google Scholar 

  • Kincannon, D.F., and Y.S. Lin. 1985. Microbial degradation of hazardous wastes by land treatment. Proc. Ind. Waste Conf. 40:607–619

    Google Scholar 

  • Kiyohara, H., K. Nagao, and R. Nomi. 1976. Degradation of phenanthrene through o–phthalate by an Aeromonas sp. Agric. Biol. Chem. 40:1075–1082.

    Article  CAS  Google Scholar 

  • Kiyohara, H., and K. Nagao. 1978. The catabolism of phenanthrene and naphthalene by bacteria. J. Gen. Microbiol. 105:69–75.

    CAS  Google Scholar 

  • Kiyohara, H., K. Nagao, K. Kouno, and K. Yano. 1982. Phenanthrene–degrading phenotype of Alcaligenes faecalis AFK2. Appl. Environ. Microbiol. 43:458–461.

    CAS  Google Scholar 

  • Köhler, A., M. Schüttoff, D. Bryniok, and H.-J. Knackmuss. 1994. Enhanced biodegradation of phenanthrene in a biphasic culture system. Biodegradation 5: 93–103 .

    Article  Google Scholar 

  • Kotterman, M.J.J., R.A. Wasseveld, and J.A. Field. 1995. Influence of nitrogen sufficiency and manganese deficiency on PAH degradation by Bjerkandera sp. In: Bioaugmentation for site remediation (Edited by R.E. Hinchee, J. Fredrickson, and B.C. Alleman). Book 3(3) of the third international in situ and on–site bioreclamation symposium, San Diego, California, USA. Battelle Press, Columbus, USA.

    Google Scholar 

  • Kuhm, A.E., A. Stolz, and H.-J. Knackmuss. 1991. Metabolism of naphthalene by the biphenyldegrading bacterium Pseudomonas paucimobilis Q1. Biodegradation 2:115–120.

    Article  CAS  Google Scholar 

  • Lambert, M., S. Kremer, O. Sterner, and H. Anke. 1994. Metabolism of pyrene by the basidiomycete Crinipellis stipitaria and identification of pyrenequinones and their hydroxylated precursors in strain JK375. Appl. Environ. Microbiol. 60:3602–3607.

    Google Scholar 

  • Lambert, M. 1993. Vergleich des PAK–Abbaues im Boden und in Submerskultur durch Basidiomyceten und Deuteromyceten und Untersuchungen zum Pyren–Metabolimus durch Crinipellis stipitaria. Ph. D. Thesis, University of Kaiserslautern, Germany.

    Google Scholar 

  • Lange, B., S. Kremer, O. Sterner, and H. Anke. 1994. Pyrene metabolism in Crinipellis stipitaria: Identification of trans–4,5–dihydro–4,5–dihydroxypyrene and 1–pyrenylsulfate in strain JK364. Appl. Environ. Microbiol. 60:3602–3607.

    CAS  Google Scholar 

  • Langenhoff, A. A. M., A. J. B. Zehnder, and G. Schraa. 1996. Behaviour of toluene, benzene and naphthalene under anaerobic conditions in sediment columns. Biodegradation 7:267–274.

    Article  CAS  Google Scholar 

  • Langenhoff, A. A. M. 1997. Biotransformation of toluene, benzene and naphthalene under anaerobic conditions. Ph.D. Thesis, Wageningen Agricultural University, The Netherlands.

    Google Scholar 

  • Lantz, S., J-E . Lin, J.G. Mueller, and P. H. Pritchard. 1995. Effects of surfactants on fluoranthene mineralization by Sphingomonas paucimobilis strain EPA 505. In: Microbial processes for bioremediation (Edited by R.E. Hinchee, C.M. Vogel, and F.J. Brockman). Book 3(8) of the third international in situ and on–site bioreclamation symposium, San Diego, California, USA. Battelle Press, Columbus, USA.

    Google Scholar 

  • Lee, M. D., J.T. Wilson, and C.H. Ward. 1984. Microbial degradation of selected aromatics in a hazardous waste site. Dev. Ind. Microbiol. 25:557–565.

    CAS  Google Scholar 

  • Lee, M.D., and R.L. Raymond. 1991. Case history of the application of hydrogen peroxide as an oxygen source for in situ bioreclamation. In: In situ bioreclamation: Applications and investigations for hydrocarbon and contaminated site remediation (Edited by R.E. Hinchee, and R.F. Olfenbuttel). Butterworth–Heinemann, Massachusetts, USA.

    Google Scholar 

  • Lee, M. D., W. A. Butler, T.F. Mistretta, I.J. Zanikos, and R. E. Perkins. 1994. Biological treatability studies on surface impoundment sludge from a chemical manufacturing facility. In: Bioremediation of chlorinated and polycyclic aromatic hydrocarbon compounds (Edited by R.E. Hinchee, A. Leeson, L. Semprini, and S. K. Ong). CRC Press, New York, USA.

    Google Scholar 

  • MacGillivray, A.R., and M.P. Shiaris. 1993. Biotransformation of polycyclic aromatic hydrocarbons by yeasts isolated from coastal sediments. Appl. Environ. Microbiol. 59:1613–1618.

    CAS  Google Scholar 

  • MacGillivray, A.R., and M.P. Shiaris. 1994. Relative role of eukaryotic and prokaryotic microorganisms in phenanthrene transformation in coastal sediments. Appl. Environ. Microbiol. 60:1154–1159.

    CAS  Google Scholar 

  • Mahaffey, W.R., D.T. Gibson, and C.E. Cerniglia. 1988. Bacterial oxidation of chemical carcinogens: Formation of polycyclic aromatic acids from benz[a]anthracene. Appl. Environ. Microbiol. 54: 2415–2423 .

    CAS  Google Scholar 

  • Mahro, B., G. Schaefer, and M. Kästner. 1994. Pathways of microbial degradation of polycyclic aromatic hydrocarbons in soil. In: Bioremediation of chlorinated and polycyclic aromatic hydrocarbon compounds (Edited by R.E. Hinchee, A. Leeson, L. Semprini, and S. K. Ong). CRC Press, New York, USA.

    Google Scholar 

  • Mahro, B., and M. Kästner. 1993a. Der mikrobielle Abbau polyzyklischer aromatischer Kohlenwasserstoffe (PAK) in Böden und Sedimenten: Mineralisierung, Metabolitenbildung und Entstehung gebundener Rückstände. Bio. Engineering 9:50–58.

    CAS  Google Scholar 

  • Mahro, B., and M. Kästner. 1993b. Mechanisms of microbial degradation of polycyclic aromatic hydrocarbons (PAH) in soil–compost mixtures. In: Contaminated soil ’93 (Edited by F. Arendt, G.J. Annokkée, R. Bosman, and W.J. van den Brink). Kluwer Academic Publishers, Dordrecht, The Netherlands.

    Google Scholar 

  • Manilal, V.B., and M. Alexander. 1991. Factors affecting the microbial degradation of phenanthrene in soil. Appl. Microbiol. Biotechnol. 35:401–405.

    Article  CAS  Google Scholar 

  • Martens, R. 1982. Concentrations and microbial mineralization of four to six ring polycyclic aromatic hydrocarbons in composed municipal waste. Chemosphere 11:761–770.

    Article  CAS  Google Scholar 

  • Means, J. C., J.J. Hasett, S. G. Wood, and W.L. Banwart. 1980. Sorption properties of polynuclear aromatic hydrocarbons by sediments and soils. Environ. Sci. Technol. 14:1524–1528.

    Article  CAS  Google Scholar 

  • Mihelcic, J.R., and R.G. Luthy. 1988a. Degradation of polycyclic aromatic hydrocarbon compounds under various redox conditions in soil–water systems. Appl. Environ. Microbiol. 54:1182–1187.

    CAS  Google Scholar 

  • Mihelcic, J. R. , and R.G. Luthy. 1988b. Microbial degradation of acenaphthene and naphthalene under denitrification conditions in soil–water systems. Appl. Environ. Microbiol. 54:1188–1198.

    CAS  Google Scholar 

  • Mihelcic, J.R., and R.G. Luthy. 1991. Sorption and microbial degradation of naphthalene in soilwater suspensions under denitrification conditions. Environ. Sci. Technol. 25:169–177.

    Article  CAS  Google Scholar 

  • Moen, M.A., and K.E. Hammel. 1994. Lipid peroxidation by the manganese peroxidase of Phanerochaete chrysosporium is the basis for phenanthrene oxidation by the intact fungus. Appl. Environ. Microbiol. 60:1956–1961.

    CAS  Google Scholar 

  • Møller, J., and H. Ingvorsen. 1993. Biodegradation of phenanthrene in soil microcosms stimulated by an introduced Alcaligenes sp. FEMS Microbiol. Ecol. 102:271–278.

    Article  Google Scholar 

  • Monna, L., T. Omori, and T. Kodama. 1993. Microbial degradation of dibenzofuran, fluorene, and dibenzo–p–dioxin by Staphylococcus auriculans DBF63. Appl. Environ. Microbiol. 59:285–289.

    CAS  Google Scholar 

  • Mueller, J.G., P.J. Chapman, and P.H. Pritchard. 1989. Action of a fluoranthene–utilizing bacterial community on polycyclic aromatic hydrocarbon components of creosote. Appl. Environ. Microbiol. 55:3085–3090.

    CAS  Google Scholar 

  • Mueller, J.G., P.J. Chapman, B.O. Blattmann, and P.H. Pritchard. 1990. Isolation and characterization of a fluoranthene–utilizing strain of Pseudomonas paucimobilis. Appl. Environ. Microbiol. 56:1079–1086.

    CAS  Google Scholar 

  • Narro, M.L., C.E. Cerniglia, C. van Baalen, and D.T. Gibson. 1992a. Metabolism of phenanthrene by the marine cyanobacterium Agmenellum quadruplicatum PR–6. Appl. Environ. Microbiol. 58 :1351–1359 .

    CAS  Google Scholar 

  • Narro, M. L. , C. E. Cerniglia, C. van Baalen, and D. T. Gibson. 1992b. Evidence for an NIH shift in oxidation of naphthalene by the marine cyanobacterium Oscillatoria species strain JCM. Appl. Environ. Microbiol. 58 :1360–1363 .

    CAS  Google Scholar 

  • Nielsen, P. H., and T.H. Christensen. 1994. Spatial variability of aerobic degradation potential for organic pollutants. In: Bioremediation of chlorinated and polycyclic aromatic hydrocarbon compounds (Edited by R.E. Hinchee, A. Leeson, L. Semprini, and S. K. Ong). CRC Press, New York, USA.

    Google Scholar 

  • Patterson, J.W., and P.S. Kodukala. 1981. Biodegradation of hazardous organic pollutants. Chem. Eng. Progr. 77:48–55.

    CAS  Google Scholar 

  • Persson, N.A., and T.G. Welander. 1994. Biotreatment of petroleum hydrocarbon–containing sludges by land application: A case history and prospects for future treatment. In: Hydrocarbon bioremediation (Edited by R. E. Hinchee, B.C. Alleman, R. E. Hoeppel, and R. N. Miller). CRC Press, New York, USA.

    Google Scholar 

  • Phillips, P., J. Bender, J. Word, D. Niyogi, and B. Denovan. 1994. Mineralization of naphthalene, phenanthrene, chrysene, and hexadecane with constructed silage microbial mat. In: Applied biotechnology for site remediation (Edited by R.E. Hinchee, D.B. Anderson, F. Blaine Metting (jr.), and G.D. Sayles). CRC Press, New York, USA.

    Google Scholar 

  • Pothuluri, J.V., J.P. Freeman, F.E. Evans, and C.E. Cerniglia. 1990. Fungal transformation of fluoranthene. Appl. Environ. Microbiol. 56:2974–2983.

    CAS  Google Scholar 

  • Pothuluri, J.V., J.P. Freeman, F.E. Evans, and C.E. Cerniglia. 1992a. Fungal metabolism and detoxification of fluoranthene. Appl. Environ. Microbiol. 58:937–941.

    CAS  Google Scholar 

  • Pothuluri, J.V., J.P. Freeman, F.E. Evans, and C.E. Cerniglia. 1992b. Fungal metabolism of acenaphthene by Cunninghamella elegans. Appl. Environ. Microbiol. 58:3654–3659.

    CAS  Google Scholar 

  • Pothuluri, J.V., J.P. Freeman, F.E. Evans, and C.E. Cerniglia. 1993. Biotransformation of fluorene by the fungus Cunninghamella elegans. Appl. Environ. Microbiol. 59:1977–1980.

    CAS  Google Scholar 

  • Rogoff, M.H. 1962. Chemistry of oxidation of polycyclic aromatic hydrocarbons by soil Pseudomonads. J. Bacteriol. 83:998–1004.

    CAS  Google Scholar 

  • Sanglard, D., M.S.A. Leisola, and A. Fiechter. 1986. Role of extracellular ligninases in biodegradation of benzo[a]pyrene by Phanerochaete chrysosporium. Enzyme Microbiol. Technol. 8:209–212.

    Article  CAS  Google Scholar 

  • Schenk, B., W. Böhmer, C. Langstein, K. Hund, and S. Hermann. 1992. Biodegradation of polycyclic aromatic hydrocarbons (PAH) in soil (on site and laboratory studies). In: Preprints of the International Symposium ‘Soil decontamination using biological processes’ , Karlsruhe, Germany. Dechema, Frankfurt am Main, Germany.

    Google Scholar 

  • Schneider, J., R. Grosser, K. Jayasimhulu, W. Xue, and D. Warshawsky. 1996. Degradation of pyrene, benz[a]anthracene, and benzo[a]pyrene by Mycobacterium sp. strain RJGII–135, isolated from a former coal gasification site. Appl. Environ. Microbiol. 62:13–19.

    CAS  Google Scholar 

  • Schocken, M.J., and D.T. Gibson. 1984. Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphtylene. Appl. Environ. Microbiol. 48:10–16.

    CAS  Google Scholar 

  • Sherrill, T.W., and G.W. Sayler. 1980. Phenanthrene biodegradation in freshwater environments. Appl. Environ. Microbiol. 39:172–178.

    CAS  Google Scholar 

  • Shiaris, M.P., and J.J. Cooney. 1983. Replica plating method for estimating phenanthreneutilizing and phenanthrene–cometabolizing microorganisms. Appl. Environ. Microbiol. 45:706–710.

    CAS  Google Scholar 

  • Shiaris, M.P. 1989. Seasonal biotransformation of naphthalene, phenanthrene, and benzo[a]pyrene in surficial sediments. Appl. Environ. Microbiol. 55:1391–1399.

    CAS  Google Scholar 

  • Smith, M.R. 1990. The biodegradation of aromatic hydrocarbons by bacteria. Biodegradation 1:191–206.

    Article  CAS  Google Scholar 

  • Stieber, M., P. Werner, and F.H. Frimmel. 1994. Investigations on the microbial degradation of polycyclic aromatic hydrocarbons (PAHs) in contaminated soils. In: Bioremediation of chlorinated and polycyclic aromatic hydrocarbon compounds (Edited by R.E. Hinchee, A. Leeson, L. Semprini, and S. K. Ong). CRC Press, New York, USA.

    Google Scholar 

  • Stringfellow, W.T., and M.D. Aitken. 1995. Competitive metabolism of naphthalene, methylnaphthalenes, and fluorene by phenanthrene–degrading Pseudomonads. Appl. Environ. Microbiol . 61: 357–362 .

    CAS  Google Scholar 

  • Stucki, G., and M. Alexander. 1987. Role of dissolution rate and solubility in biodegradation of aromatic compounds. Appl. Environ. Microbiol. 53:292–297.

    CAS  Google Scholar 

  • Sutherland, J. B., J.P. Freeman, A. L. Selby, P. P. Fu, D.W. Miller, and C. E. Cerniglia. 1990. Stereoselective formation of a K–region dihydrodiol from phenanthrene by Streptomyces flavovirens. Arch. Microbiol. 154:260–266.

    Article  CAS  Google Scholar 

  • Sutherland, J.B., A.L. Selby, J.P. Freeman, F.E. Evans, and C.E. Cerniglia. 1991. Metabolism of phenanthrene by Phanerochaete chrysosporium. Appl. Environ. Microbiol. 57:3310–3316.

    CAS  Google Scholar 

  • Sutherland, J.B., P.P. Fu, S.K. Yang, L.S. von Tungeln, R.P. Casillas, S.A. Crow, and C.E. Cerniglia. 1993. Enantiomeric composition of the trans–dihydrodiols produced from phenanthrene by fungi. Appl. Environ. Microbiol. 59:2145–2149.

    CAS  Google Scholar 

  • Symons, B. D., R. Linkenheil, D. Pritchard, C. A. Shanke, and D. Seep. 1995. In situ groundwater aeration of polycyclic aromatic hydrocarbons. In: In situ aeration: Air sparging, bioventing, and related remediation processes (Edited by R.E. Hinchee, R.N. Miller, and P.C. Johnson). Book 3(2) of the third international in situ and on–site bioreclamation symposium, San Diego, California, USA. Battelle Press, Columbus, USA.

    Google Scholar 

  • Thierrin, J., G.B. Davis, C. Barber, B.M. Patterson, F. Pribac, T.R. Power, and M. Lambert. 1993. Natural degradation rates of BTEX compounds and naphthalene in a sulfate–reducing groundwater environment. Hydro. Sci. J. 38:309–322.

    Article  CAS  Google Scholar 

  • Tiehm, A. 1994. Degradation of polycyclic aromatic hydrocarbons in the presence of synthetic surfactants. Appl. Environ. Microbiol. 60:258–263.

    CAS  Google Scholar 

  • Tiehm, A., and C. Fritzsche. 1995. Utilization of solubilized and crystalline mixtures of polycyclic aromatic hydrocarbons by a Mycobacterium sp. Appl. Microbiol. Biotechnol. 42:964–968

    Article  CAS  Google Scholar 

  • Tremaine, S.C., P.E. McIntire, P.E. Bell, A.K. Siler, N.B. Matolak, T.W. Payne, and N.A. Nimo. 1994. Bioremediation of water and soils contaminated with creosote: Suspension and fixed–film vs. constructed wetlands and plowing vs. solid peroxygen treatment. In: Bioremediation of chlorinated and polycyclic aromatic hydrocarbon compounds (Edited by R.E. Hinchee, A. Leeson, L. Semprini, and S. K. Ong). CRC Press, New York, USA.

    Google Scholar 

  • Trust, B. A., J.G. Mueller, R. B. Coffin, and L.A. Cifuentes . 1995. The biodegradation of fluoranthene as monitored using stable carbon isotopes. In: Monitoring and verification of bioremediation (Edited by R.E. Hinchee, G.S. Douglas, S.K. Ong). Book 3(5) of the third international in situ and on–site bioreclamation symposium, San Diego, California, USA. Battelle Press, Columbus, USA.

    Google Scholar 

  • Vail, R.L. 1991. Refiner biodegrades separator–type sludge to BDAT standards. Oil and Gas J. 11:53–57.

    Google Scholar 

  • Van Starkenburg, W. 1981. Polycyclische aromatische koolwaterstoffen. RIZA (publicatie No. 81047), The Netherlands.

    Google Scholar 

  • VROM. 1994. Herziening van de lijst met prioritaire stoffen. Publicatiereeks stoffen, veiligheid, straling (nr. 1994/16). VROM, Zoetermeer, The Netherlands.

    Google Scholar 

  • Walter, U., M. Beyer, J. Klein, and H.J. Rehm. 1991. Degradation of pyrene by Rhodococcus sp. UW1. Appl. Microbiol. Biotechnol. 34:671–676.

    Article  CAS  Google Scholar 

  • Wang, X. , Y. Yu, and R. Bartha. 1990. Effect of bioremediation on polycyclic aromatic hydrocarbon residues in soil. Environ. Sci. Technol. 24:1086–1089.

    Article  CAS  Google Scholar 

  • Warshawsky, D., T.M. Keenan, R. Reilman, T.E. Cody, and M.J. Radike. 1990. Conjugation of benzo[a]pyrene metabolites by the freshwater green alga Selenastrum capricornutum. Chem.Biol. Interact. 73:93–105.

    Article  Google Scholar 

  • Weissenfels, W.D., M. Beyer, and J. Klein. 1990a. Degradation of phenanthrene, fluorene and fluoranthene by pure bacterial cultures. Appl. Microbiol. Biotechnol. 32:479–484.

    Article  CAS  Google Scholar 

  • Weissenfels, W.D., M. Beyer, and J. Klein. 1990b. Rapid testing for assessing the suitability of the biological reclamation for PAH–contaminated soil. In: Proceedings of the 5th Eur. Congress on Biotechnology (Edited by C. Christiansen, L. Munck, and J. Villadsen). Munksgaard, Denmark.

    Google Scholar 

  • Weissenfels, W.D., M. Beyer, and H.J. Rehm. 1991. Microbial metabolism of fluoranthene: Isolation and identification of ring fission products. Appl. Microbiol. Biotechnol. 34:528–535.

    Article  CAS  Google Scholar 

  • Wilson, J.T., J.F. McNabb, J.W. Cochran, T.H. Wang, M.B. Tomson, and P.B. Bedient. 1985. Influence of microbial adaptation of the fate of organic pollutants in groundwater. Environ. Toxicol. and Chem. 4:721–726.

    CAS  Google Scholar 

  • Wittmaier, M., P. Harborth, and H.H. Hanert. 1992. Biological activity, pollutant degradation and detoxification in soil highly contaminated with tar oil (> 100,000 mg PAH/kg dry subst.). In: Soil decontamination using biological processes. Schön and Wetzel, Germany.

    Google Scholar 

  • Wunder, T., S. Kremer, O. Sterner, and H. Anke. 1994. Metabolism of the polycyclic aromatic hydrocarbon pyrene by Aspergillus niger SK 9317. Appl. Microbiol. Biotechnol. 42:636–641.

    Article  CAS  Google Scholar 

  • Würdemann, H., N.C. Lund, and G. Gudehus. 1995. Assessment of a biological in situ remediation. In: In situ aeration: Air sparging, bioventing, and related remediation processes (Edited by R.E. Hinchee, R.N. Miller, and P.C. Johnson). Book 3(2) of the third international in situ and on–site bioreclamation symposium, San Diego, California, USA. Battelle Press, Columbus, USA.

    Google Scholar 

  • Zyistra, G.J., A.K. Goyal, and E. Kim. 1996. Diversity of genes for polycyclic aromatic hydrocarbons. In: Proceedings of the UIB–GBF–CSIC–TUB symposium: Biodegradation of organic pollutants. Palma de Mallorca, 29 June–3 July, Mallorca, Spain.

    Google Scholar 

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van Agteren, M.H., Keuning, S., Janssen, D.B. (1998). Polyaromatic hydrocarbons (PAHs). In: Handbook on Biodegradation and Biological Treatment of Hazardous Organic Compounds. Environment & Chemistry, vol 2. Springer, Dordrecht. https://doi.org/10.1007/978-94-015-9062-4_5

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