Biotransformation of linear alkylbenzene sulfonate (LAS) by Phanerochaete chrysosporium : oxidation of alkyl side-chain

Biodegradation - Tập 12 - Trang 443-453 - 2001
Jagjit S. Yadav1, David L. Lawrence2, Barbara A. Nuck2, Thomas W. Federle2, C. Adinarayana Reddy3
1Department of Environmental Health, Division of Molecular Toxicology, University of Cincinnati, Cincinnati, USA
2Environmental Science Department, The Procter & Gamble Company, Cincinnati, USA
3Department of Microbiology and the NSF Center for Microbial Ecology, Michigan State University, East Lansing, USA Author for correspondence

Tóm tắt

The white rot fungus Phanerochaete chrysosporium, which generally mineralizes substituted aromatics to CO2, transformed linear alkylbenzene sulfonate (LAS) surfactants mainly at their alkyl side chain. Degradation of LAS was evidenced by a zone of clearing on LAS-containing agar plates and colorimetric analysis of liquid cultures. Disappearance of LAS was virtually complete within 10 days in low nitrogen (2.4 mM N), high nitrogen (24 mM N) and malt extract (ME) liquid media. After 5 days of incubation in ME medium, transformation of LAS was complete at concentrations≤4 mg l-1, but decreased at higher concentrations. The LAS degradation was not dependent on lignin peroxidases (LiPs) and manganese-dependent peroxidases (MnPs). Mineralization of14C-ring-LAS to 14CO2 by P. chrysosporium was <1% regardless of the culture conditions used. Thin layer chromatography and mass spectral analyses indicated that P. chrysosporium transformed LAS to sulfophenyl carboxylates (SPCs) through oxidative shortening of the alkyl side-chains. While LAS disappearance in the cultures was not dependent on LiPs and MnPs, transformation of the parent LAS moieties to SPCs was more extensive in low N medium that favors expression of these enzymes. The SPCs produced in LN cultures were shorter in chain-length than those produced in ME cultures. Also there was a notable shift in the relative abundance of odd and even chain length metabolites compared to the starting LAS particularly in the low N cultures suggesting the possible involvement of processes other than or in addition toβ-oxidation in the chain-shortening process.

Tài liệu tham khảo

Allred RC,Setzkorn EA &Huddleston RL (1964) A study of detergent biodegradability as shown by various analytical techniques. J. Amer. Oil. Chem. Soc. 41: 13-17 Aust SD (1990) Degradation of environmental pollutants by Phanerochaete chrysosporium. Microbial Ecol. 20: 197-209 Boominathan K,Dass SB,Randall TA,Kelley RL &Reddy CA (1990a) Lignin peroxidase-negative mutant of the white-rot basidiomycete Phanerochaete chrysosporium. J. Bacteriol. 172: 260-265 Boominathan K,Dass SB,Randall TA &Reddy CA (1990b) Nitrogen-deregulated mutants of Phanerochaete chrysosporium-a lignin-degrading basidiomycete. Arch. Microbiol. 153: 521-527 Breen A,Jimenez L,Sayler GS &Federle TW (1992) Plasmid incidence and linear alkylbenzene sulfonate biodegradation in wastewater and pristine pond ecosystems. J. Industr. Microbiol. 9: 37-44 Campos-Garcia J,Esteve A,Vazquez-Duhalt R,Ramos JL &Soberon-Chavez G (1999) The branched-chain dodecylbenzene sulfonate degradation pathway of Pseudomonas aeruginosa W51D involves a novel route for degradation of the surfactant lateral alkyl chain. Appl. Environ. Microbiol. 65: 3730-3734 Hammel KE (1992) Oxidation of aromatic pollutants by lignindegrading fungi and their extracellular peroxidases. In: Sigel H &Sigel A (Eds) Metal Ions in Biological Systems, Degradation of Environmental Pollutants by Microorganisms and their Metalloenzymes, Vol. 28 (pp 41-60). Marcel Dekker Inc., New York Kohler A,Jager A,Willershausen H &Graf H (1988) Extracellular ligninase of Phanerochaete chrysosporium Burdsall has no role in the degradation of DDT. Appl. Microbiol. Biotechnol. 29: 618-620 Kertesz MA,Kolbener P,Stockinger H,Beil S &Cook AM (1994) Desulfonation of linear alkylbenzene sulfonate surfactants and related compounds by bacteria. Appl. Environ. Microbiol. 60: 2296-2303 Longwell J &Maniece WD (1955) Determination of anionic detergents in sewage, sewage effluents and river waters. Analyst 80: 167-171 McEnvoy J &Giger W (1986) Determination of linear alkylbenzene sulfonates in sewage sludge by high-resolution gas chromatography/mass spectrometry. Environ. Sci. Technol. 20: 376-383 Muralikrishna, C. &Renganathan, V. (1993) Peroxidase-mediated desulfonation of 3,5-dimethyl-4-hydroxy and 3,5-dimethyl-4-aminobenzenesulfonic acids. Biochem. Biophys. Res. Commun. 197: 798-804. Pszczynski A &Crawford RL (1995) Potential for bioremediation of xenobiotic compounds by the white rot fungus Phanerochaete chrysosporium. Biotechnol Prog 11: 368-379 Pszczynski A,Crawford RL &Huynh VB (1988) Manganese peroxidase of Phanerochaete chrysosporium. Methods Enzymol. 161: 264-271 Paszczynski A,Pasti-Gigsby M B,Goszczynski S,Crawford R L &Crawford DL (1992) Mineralization of sulfonated azo dyes and sulfanilic acid by Phanerochaete chrysosporium and Streptomyces chromofuscus. Appl. Environ. Microbiol. 58: 3598-3604 Rapaport RA &Eckhoff WS (1990) Monitoring linear alkylbenzene sulfonate in the environment: 1973-1986. Environ. Toxicol. Chem. 9: 1245-1257 Reddy CA (1995) The potential of white rot fungi for the treatment of pollutants. Curr. Opinion Biotechnol. 6: 320-328 Reddy CA &D'souza TM (1994) Physiology and molecular biology of the lignin peroxidases of Phanerochaete chrysosporium. FEMS Microbiol. Rev. 13: 137-152 Reddy GVB,Joshi DK &Gold MH (1997) Degradation of chlorophenoxyacetic acids by the lignin-degrading fungus Dichomitus squalens. Microbiol 143: 2353-2360 Schleheck D,Dong W,Denger K,Heinzle E &Cook AM (2000) Aproteobacterium converts linear alkylbenzene sulfonate surfactants into sulfophenyl carboxylates and linear alkyldiphenylether sulfonate surfactants into sulfodiphenylethercarboxylates. Appl. Environ. Microbiol. 66: 1911-1916 Sigoillot JC &Nguyen MH (1992) Complete oxidation of linear alkylbenzene sulfonate by bacterial communities selected from coastal seawater. Appl. Environ. Microbiol. 58: 1308-1312 Slack JG (1959) The determination of anionic detergents in river water and sewage effluents. Analyst 84:193 Sutherland JB,Selby AL,Freeman JP,Evans FE &Cerniglia CE (1991) Metabolism of phenanthrene by Phanerochaete chrysosporium. Appl. Environ. Microbiol. 57: 3310-3316 Swisher RD (1987) Surfactant Biodegradation, 2nd ed. Marcel Dekker Inc., New York Tien M &Kirk TK (1988) Lignin peroxidase of Phanerochaete chrysosporium. Methods Enzymol. 161: 238-249 Webster HL &Halliday H (1959) Determination of alkylbenzene sulfonate in river waters and sewage. Analyst 84: 555-559 Werdelmann BW (1984) Tenside in unsereWelte-heute und morgen. In Proceedings of the Second World Surfactant Congress, Vol. 1, pp 3-21. Syndicat National des Fabricants d'Agents de Surface et de Produits Auxiliaires Industriels, Paris. Yadav JS &Reddy CA (1993a) Degradation of benzene, toluene, ethylbenzene, and xylenes (BTEX) by the lignin-degrading basidiomycete Phanerochaete chrysosporium. Appl. Environ. Microbiol. 59: 756-762 Yadav JS &Reddy CA (1993b) Mineralization of 2,4-dichlorophenoxyacetic acid (2,4-D) and mixtures of 2,4-D and 2,4,5-trichlorophenoxyacetic acid by Phanerochaete chrysosporium. Appl. Environ. Microbiol. 59: 2904-2908 Yadav JS, Quensen III JF, Tiedje JM & Reddy CA (1995) Degradation of polychlorinated biphenyl mixtures (Aroclors 1242, 1254, and 1260) by the white rot fungus Phanerochaete chrysosporium. Appl. Environ. Microbiol. 61: 2560-2565