Abstract
Several aerobic metabolic pathways for the degradation of benzene, toluene, ethylbenzene and xylene (BTEX), which are provided by two enzymic systems (dioxygenases and monooxygenases), have been identified. The monooxygenase attacks methyl or ethyl substituents of the aromatic ring, which are subsequently transformed by several oxidations to corresponding substituted pyrocatechols or phenylglyoxal, respectively. Alternatively, one oxygen atom may be first incorporated into aromatic ring while the second atom of the oxygen molecule is used for oxidation of either aromatic ring or a methyl group to corresponding pyrocatechols or protocatechuic acid, respectively. The dioxygenase attacks aromatic ring with the formation of 2-hydroxy-substituted compounds. Intermediates of the “upper” pathway are then mineralized by eitherortho-ormeta-ring cleavage (“lower” pathway). BTEX are relatively water-soluble and there-fore they are often mineralized by indigenous microflora. Therefore, natural attenuation may be considered as a suitable way for the clean-up of BTEX contaminants from gasoline-contaminated soil and groundwater.
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Althoff K.A., Mundt M., Eisentraeger A., Dott W., Hollender J.: Microcosms-experiments to assess the potential for natural attenuation of contaminated groundwater.Water Res.35, 720–728 (2001).
Alvarez P.J., Vogel T.M.: Substrate interactions of benzene, toluene andpara-xylene during microbial degradation by pure cultures and mixed culture aquifer slurries.Appl. Environ. Microbiol.57, 2981–2985 (1991).
Baldwin B.R., Mesarch M.B., Nies L.: Broad substrate specificity of naphthalene- and biphenyl-utilizing bacteria.Appl. Microbiol. Biotechnol.53, 748–753 (2000).
Bielefeldt A.R., Stensel H.D.: Biodegradation of aromatic compounds and TCE by filamentous bacteria-dominated consortium.Biodegradation10, 1–13 (1999).
Burback B.L., Perry J.J.: Biodegradation and biotransformation of groundwater pollutant mixtures byMycobacterium vacce.Appl. Environ. Microbiol.59, 1025–1029 (1993).
Chang M.K., Voice T.C., Criddle C.: Kinetics of competitive inhibition and cometabolism in the biodegradation of benzene, toluene, andp-xylene by twoPseudomonas isolates.Biotechnol. Bioeng.41, 1057–1065 (1992).
Cho J.S., Wilson J.T., DiGiulio D.C., Vardy J.A., Choi W.: Implementation of natural attenuation at a JP-4 jet fuel release after active remediation.Biodegradation8, 265–273 (1997).
Cruden D.L., Wolfram J.H., Rogers R.D., Gibson D.T.: Physiological properties of aPseudomonas strain which grows withp-xylene in two-phase (organic-aqueous) medium.Appl. Environ. Microbiol.58, 2723–2729 (1992).
Damborský J., Damborská M., Štípek S., Jesenská A., Trantírek L., Sklenář V.: Effect of the carbon source on assessment of degrading bacteria with the spread-plating technique duringin situ bioremediation.Folia Microbiol.45, 35–40 (2000).
Davey J.F., Gibson D.T.: Bacterial metabolism ofpara-andmeta-xylene: oxidation of a methyl substituent.J. Bacteriol.119, 923–929 (1974).
Davis R.S., Hossler F.E., Stone R.W.: Metabolism ofp-andm-xylene by species ofPseudomonas.Can. J. Microbiol.14, 1005–1009 (1968).
Deeb R.A., Cohen L.A.: Temperature effects and substrate interactions during the aerobic biotransformation of BTEX mixtures by toluene-enriched consortia andRhodococcus rhodochrous.Biotech. Bioeng.62, 526–536 (1999).
Fries M.R., Chee-Zhou J., Sauford J., Tiedje J.M.: Isolation, characterization, and distribution of denitrifying toluene degraders from a variety of habitats.Appl. Environ. Microbiol.60, 2802–2810 (1994).
Furukawa K., Simon J.R., Chakrabarty A.M.: Common induction and regulation of biphenyl, xylene/toluene, and salicylate catabolism inPseudomonas paucimobilis.J. Bacteriol.154, 1356–1362 (1983).
Gibson D.T., Mahadevan V., Davey J.F.: Bacterial metabolism ofpara- andmeta-xylene: oxidation of the aromatic ring.J. Bacteriol.119, 930–936 (1974).
Häner A., Hohener P., Zeyer J.: Degradation ofp-xylene by denitrifying enrichment culture.Appl. Environ. Microbiol.61, 3185–3188 (1995).
Harayama S., Rekik M., Wubbolt S., Rose K., Leppik R.A., Timmis K.N.: Characterization of five genes in the upper-pathway operon of TOL plasmid pWWO fromPseudomonas putida and identification of the gene products.J. Bacteriol.171, 5048–5055 (1989).
Harwood C.S., Gibson J.: Shedding light on anaerobic benzene ring degradation: a process unique to prokaryotes.J. Bacteriol.179, 301–309 (1997).
Heider J., Fuchs G.: Anaerobic metabolism of aromatic compounds.Eur. J. Biochem.243, 577–596 (1997).
Holden P.A., Halverson L.J., Firestone M.K.: Water stress effects on toluene biodegradation byPseudomonas putida.Biodegradation8, 143–148 (1997).
Hyman M.R., Sansome-Schmith A.W., Shears J.H., Wood P.M.: A kinetic study of benzene oxidation to phenol by whole cells ofNitrosomonas europea and evidence for the further oxidation of phenol to hydroquinone.Arch. Microbiol.143, 302–306 (1985).
Kao C.M., Prosser J.: Evaluation of natural attenuation rate at a gasoline spill site.J. Hazard. Mat.B82, 275–289 (2001).
Keener W.K., Arp D.J.: Transformations of aromatic compounds byNitrosomonas europea.Appl. Environ. Microbiol.60, 1914–1920 (1994).
Kobal V.M., Gibson D.T., Davis R.E., Garza A.: X-ray determination of the absolute stereochemistry of the initial oxidation product formed from toluene byPseudomonas putida 39/D.J. Am. Chem. Soc.95, 4420–4421 (1973).
Kukor J.J., Olsen R.H.: Catechol-2,3-dioxygenases functional in oxygen-limited (hypoxic) environments.Appl. Environ. Microbiol.62, 1728–1740 (1996).
Lang E.: Diversity of bacterial capabilities in utilizing alkylated benzenes and other aromatic compounds.Lett. Appl. Microbiol.23, 257–260 (1996).
Lee K., Gibson D.T.: Toluene and ethylbenzene oxidation by purified naphthalene dioxygenase fromPseudomonas sp. strain NCIB 9816-4.Appl. Environ. Microbiol.62, 3101–3106 (1996).
Lee J.F., Liao P.M., Kuo C.C., Yang H.T., Chiou C.T.: Influence of nonionic surfactant (Triton X-100) on contaminant distribution between water and several soil solids.J. Coll. Internat. Sci.229, 445–452 (2000).
Marek J., Páca J., Halecký M., Koutský B., Sobotka M., Keshavarz T.: Effect of pH and loading manner on the start-up period of peat biofilter degrading xylene and toluene mixture.Folia Microbiol.46, 205–209 (2001).
Marr E.K., Stone R.W.: Bacterial oxidation of benzene.J. Bacteriol.18, 425–430 (1961).
Murray K., Duggleby C.J., Sala-Trepat J.M., Williams P.A.: The metabolism of benzoate and methylbenzoatesvia themeta-cleavage pathway byPseudomonas arvilla mt-2.Eur. J. Biochem.28, 301–310 (1972).
Obuekwe C.O., Hourani G., Radwan S.S.: High-temperature hydrocarbon biodegradation activities in Kuwaiti Desert soil samples.Folia Microbiol.46, 535–539 (2001).
Oh Y.S., Shareefdeen Z., Baltzis B.C., Bartha R.: Interactions between benzene, toluene andp-xylene (BTX) during their biodegradation.Biotechnol. Bioeng.44, 533–538 (1994).
Olsen R.H., Kukor J.J., Kaphammer B.: A novel toluene-3-monooxygenase pathway cloned fromPseudomonas pickettii PKO1.J. Bacteriol.176, 3749–3756 (1994).
Pinkart H.C., Wolfram J.W., Rogers R., White D.C.: Cell envelope changes in solvent-tolerant and solvent-sensitivePseudomonas putida strains following exposure too-xylene.Appl. Environ. Microbiol.62, 1129–1132 (1996).
Ramos J.L., Marques S., Timmis K.N.: Transcriptional control of thePseudomonas TOL plasmid catabolic operons is achieved through an interplay of host factors and plasmid-encoded regulators.Ann. Rev. Microbiol.51, 341–373 (1997).
Shim H., Yang S.T.: Biodegradation of benzene, toluene, ethylbenzene, ando-xylene by a co-culture ofPseudomonas putida andPseudomonas fluorescens immobilized in fibrous-bed bioreactor.J. Biotechnol.67, 99–112 (1999).
Stapleton R.D., Sayler G.S.: Assessment of the microbiological potential for the natural attenuation of petroleum hydrocarbons in a shallow aquifer system.Microb. Ecol.36, 349–361 (1998).
Tan H.M., Mason J.R.: Cloning and expression of the plasmid-encoded benzene dioxygenase genes fromP. putida ML2.FEMS Microbiol. Lett.72, 259–264 (1990).
Weigner P., Páca J., Loskot P., Koutský B., Sobotka M.: The start-up period of styrene degrading biofilters.Folia Microbiol.46, 211–216 (2001).
Whited G.M., Gibson D.T.: Toluene 4-monooxygenase, a three-component enzyme system that catalyzes the oxidation of toluene top-cresol inPseudomonas mendocina KR1.J. Bacteriol.173, 3010–3016 (1991).
Williams P.A., Murray K.: Metabolism of benzoate and the methylbenzoates byPseudomonas putida (arvilla) mt-2: evidence for the existence of a TOL plasmid.J. Bacteriol.120, 416–423 (1974).
Worsey M.J., Williams P.A.: Metabolism of toluene and xylenes byPseudomonas putida (arvilla) mt-2: evidence for a new function of the TOL plasmid.J. Bacteriol.124, 7–13 (1975).
Yen K.M., Karl M.R., Blatt L.M., Simon M.J., Winter R.B., Fausset P.R., Lu H.S., Harcourt A.A., Chen K.K.: Cloning and characterization ofPseudomonas mendocina KRI gene cluster encoding toluene-4-monooxygenase.J. Bacteriol.173, 5315–5327 (1991).
Zhang W., Bouwer E.J.: Biodegradation of benzene, toluene, toluene and naphthalene in soil-water slurry microcosms.Biodegradation8, 167–175 (1997).
Ziffer H., Jerina D.M., Gibson D.T., Kobal Val M.: Absolute stoichiochemistry of the (+)-cis-1,2-dihydroxy-3-methylcyclohexa-3,5-diene produced from toluene byPseudomonas putida.J. Am. Chem. Soc.95, 4048–4049 (1973).
Zylstra G.J., Gibson D.T.: Toluene degradation byPseudomonas putida F1.J. Biol. Chem.264, 14940–14946 (1989).
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Jindrová, E., Chocová, M., Demnerová, K. et al. Bacterial aerobic degradation of benzene, toluene, ethylbenzene and xylene. Folia Microbiol 47, 83–93 (2002). https://doi.org/10.1007/BF02817664
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DOI: https://doi.org/10.1007/BF02817664