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Microsomal Transformation of Organophosphorus Pesticides by White Rot Fungi

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Abstract

The enzymatic mechanism for the transformationof organophosphorus pesticides (OPPs) by differentwhite-rot fungi strains was studied. With theexception of Ganoderma applanatum 8168,all strains from a collection of 17 different fungicultures were able to deplete parathion. Threestrains showing the highest activities were selectedfor further studies: Bjerkandera adusta 8258,Pleurotus ostreatus 7989 and Phanerochaetechrysosporium 3641. These strains depleted 50 to96% of terbufos, azinphos-methyl, phosmet andtribufos after four-days exposure to the pesticides.In order to identify the cellular localization of thetransformation activity, the extracellular andmicrosomal fractions of Pleurotus ostreatus7989 were evaluated in vitro. While the activitiesof ligninolytic enzymes (lignin peroxidase,manganese peroxidase and laccase) weredetected in the extracellular fraction, noenzymatic modification of any of the fivepesticides tested could be found, suggestingthe intracellular origin of the transformationactivity. In accordance with this observation themicrosomal fraction was found able to transformthree OPPs with the following rates:10 μmol mg prot-1 h-1 forphosmet, 5.7 μmol mg prot-1 h-1 forterbufos, and 2.2 μmol mg prot-1 h-1 forazinphos-methyl. The products from these reactions andfrom the transformation of trichlorfon and malathion,were identified by mass-spectrometry. These results,supported by specific inhibition experiments and thestringent requirement for NADPH during the in vitroassays suggest the involvement of a cytochrome P450.

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References

  • Abdelsalm,EB (1987) Organophosphorus compounds. II. Metabolic considerations. Veterinary Res. Commun.11: 589–97

    Google Scholar 

  • Amitai G, Adani R, Sod-Moriah G, Rabinovitz I, Vincze A, Leader H, Chefetz B, Leibovitz-Persky L, Friesem & Hadar Y (1998) Oxidative biodegradation of phosphorothiolates by fungal laccase. FEBS Lett.438: 195–200

    Google Scholar 

  • Boehringer Mannheim GmbH (1975) Biochemica Information I and II. Boehringer Mannheim GmbH.Germany

  • Bossche HV & Koymans L (1998) Cytochrome P450 in fungi. Mycoses41: 32–38

    Google Scholar 

  • Bumpus JA, Kakar SN & Coleman RD (1993) Fungal degradation of organophosphorus insecticides. Appl. Biochem. Biotechnol.39/40: 715–726

    Google Scholar 

  • Butler AM & Murray M Biotransformation of parathion in human liver: participation of CYP3A4 and its inactivation during microsomal parathion oxidation. Pharmacol. Exp. Ther.280: 966973

  • CasidaJ & FukunagaK (1968) Pesticides: Metabolism, degradation, and mode of action. Science160: 445–450

    Google Scholar 

  • Cinti DL, Moldeus P & SchenkmanJB (1972) Kinetic parameters of drug-metabolizing enzymes in Ca2+-sedimented microsomes from rat liver. Biochem. Pharmacol.21: 3249–3256

    Google Scholar 

  • Davis R and Frearson M (1997) In: Prichard FE (Ed) Mass Spectrometry. Analytical Chemistry by Open Learning. John Wiley & Sons, London

    Google Scholar 

  • Engelhardt G & Wallnöfer PR (1983) Microbial transformation of benzazimide, A microbial degradation product of the insecticide azinphos-methyl. Chemosphere 12: 955–960

    Google Scholar 

  • Engelhardt G, Ziegler W, Wallnöfer PR, Oehlemann L & Wagner K (1981) Degradation of azinphos-methyl by Pseudomonadas fluorescens DMS 1976. FEMS Microbiol. Lett. 11: 165–169

    Google Scholar 

  • Eto M(1974) Organophosphorus Pesticides: Organic and Biological Chemistry. CRC Press Inc., Cleveland

  • Grue CE, Fleming WJ, Busby DG & Hill EF (1983) Assessing hazards of organophosphate pesticides to wildlife. pp 200–220 in Transactions of the 48th North American Wildlife and Natural Resources Conference. The Wildlife Management Institute, Washington, DC

    Google Scholar 

  • Hart ADM (1993) Relationships between behavior and the inhibition of acetylcholinesterase in birds exposed to organophosphorus pesticides. Environ. Toxicol. Chem. 12: 321–336

    Google Scholar 

  • Hawkins KI & Knittle CE (1972) Comparison of acetylcholinesterase determinations by the Michel and Ellman methods. Anal. Chem. 44: 416–417

    Google Scholar 

  • Hayes WJ Jr, Dale WE & Pirkle CI (1971) Evidence of safely of long-term, high, oral doses of DDT for man. Arch. Environ. Health 22: 119–135

    Google Scholar 

  • Hernandez J, Robledo NR, Velasco L, Quintero R, Pickard MA & Vazquez-Duhalt R (1998) Chloroperoxidaes-mediated oxidation of organophosphorus pesticides. Pesticide Biochem. Physiol. 61: 87–94

    Google Scholar 

  • Hileman B (2000) Reexamining pesticide risk. Chem. Eng. News 78: 34–36

    Google Scholar 

  • Hites RA (1990) CRC Handbook of Mass Spectra of Environmental Contaminants. CRC Press, Boston

    Google Scholar 

  • Lake BG (1987) Preparation and characterization of microsomal fractions for studies on xenobiotic metabolism. In: Snell & Mullock B (Eds) Biochemical Toxicology, a Practical Approach (pp 183–215). IRL Press, Oxford, UK

    Google Scholar 

  • Lin S-N, Chen C-Y, Sheldon SD & Caprioli RM(1980) Quantitative high-performance liquid chromatography and mass spectrometry for the analysis of the in vitro metabolism of the insecticide azinphos-methyl (guthion) by rat liver homogenates. J. Agric. Food Chem. 28: 85–88

    Google Scholar 

  • Ma T & Chambers JE (1994) Kinetic parameters of desulfuration and dearylation of parathion and chlorpyrifos by rat liver microsomes. Food Chem. Toxicol. 32: 763–767

    Google Scholar 

  • Moungin C, Pericaud C, Malosse C, Laugero C & Asther M (1996) Biotransformation of the insecticide Lindane by white rot basidomycete Phanerochaete chrysosporium. Pest. Sci. 47: 51–59

    Google Scholar 

  • Moungin C, Laugero C, Asther M & Chaplain V (1997) Biotransformation of S-triazine herbicides and related degradation products in liquid cultures by the white rot fungus Phanerochaete chrysosporium. Pest. Sci. 49: 169–177

    Google Scholar 

  • Munnecke DM (1976) Enzymatic hydrolysis of organophosphate insecticides, a possible pesticide disposal method. Appl. Environ. Microbiol. 32: 7–13

    Google Scholar 

  • Pickard MA, Roman R & Vazquez-Duhalt R (1999) High production and ligninolytic enzymes from white rot fungi cereal-bran liquid medium. Can. J. Microbiol. 45: 627–631

    Google Scholar 

  • Storrie B & Madden EA (1990) Isolation of subcellular organelles. Methods Enzymol. 182: 203–225

    Google Scholar 

  • Tien M & Kirk TK (1988) Lignin peroxidase of Phanerochaete chrysosporium. Methods Enzymol. 161: 238–248

    Google Scholar 

  • Tinoco R, Pickard MA & Vazquez-Duhalt R (2000) Kinetic differences of laccases from six Pleurotus ostreatus strains. Lett. Appl. Microbiol. 32: 331–335

    Google Scholar 

  • Yoshihara & Neal RA (1977) Comparison of the metabolism of parathion by a rat liver reconstituted mixed function oxidase enzyme system and by a system containing cumene hydroperoxide and purified liver cytochrome P450. Drug Metab. Disp. 5: 191–197

    Google Scholar 

  • Whitehouse LW & Ecobichon DJ (1975) Paraoxon formation and hydrolysis by mammalian liver. Pestic. Biochem. Physiol. 5: 314–322

    Google Scholar 

  • Wiriishi HK & Gold M (1992) Manganese (II) oxidation by manganese peroxidase from the basidiomycete Phanerochate chrisosporium. J. Biol. Chem. 267: 23688–23695

    Google Scholar 

  • Woolfenden BS & Wilson RL (1982) Radical cations as reference chromogens in studies of one-electron transfer reactions: Pulse radiolysis studies of 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulfonate). J. Chem. Soc. II805–812

    Google Scholar 

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Jauregui, J., Valderrama, B., Albores, A. et al. Microsomal Transformation of Organophosphorus Pesticides by White Rot Fungi. Biodegradation 14, 397–406 (2003). https://doi.org/10.1023/A:1027316610450

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