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.
Similar content being viewed by others
References
Abdelsalm,EB (1987) Organophosphorus compounds. II. Metabolic considerations. Veterinary Res. Commun.11: 589–97
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
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
Bumpus JA, Kakar SN & Coleman RD (1993) Fungal degradation of organophosphorus insecticides. Appl. Biochem. Biotechnol.39/40: 715–726
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
Cinti DL, Moldeus P & SchenkmanJB (1972) Kinetic parameters of drug-metabolizing enzymes in Ca2+-sedimented microsomes from rat liver. Biochem. Pharmacol.21: 3249–3256
Davis R and Frearson M (1997) In: Prichard FE (Ed) Mass Spectrometry. Analytical Chemistry by Open Learning. John Wiley & Sons, London
Engelhardt G & Wallnöfer PR (1983) Microbial transformation of benzazimide, A microbial degradation product of the insecticide azinphos-methyl. Chemosphere 12: 955–960
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
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
Hart ADM (1993) Relationships between behavior and the inhibition of acetylcholinesterase in birds exposed to organophosphorus pesticides. Environ. Toxicol. Chem. 12: 321–336
Hawkins KI & Knittle CE (1972) Comparison of acetylcholinesterase determinations by the Michel and Ellman methods. Anal. Chem. 44: 416–417
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
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
Hileman B (2000) Reexamining pesticide risk. Chem. Eng. News 78: 34–36
Hites RA (1990) CRC Handbook of Mass Spectra of Environmental Contaminants. CRC Press, Boston
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
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
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
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
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
Munnecke DM (1976) Enzymatic hydrolysis of organophosphate insecticides, a possible pesticide disposal method. Appl. Environ. Microbiol. 32: 7–13
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
Storrie B & Madden EA (1990) Isolation of subcellular organelles. Methods Enzymol. 182: 203–225
Tien M & Kirk TK (1988) Lignin peroxidase of Phanerochaete chrysosporium. Methods Enzymol. 161: 238–248
Tinoco R, Pickard MA & Vazquez-Duhalt R (2000) Kinetic differences of laccases from six Pleurotus ostreatus strains. Lett. Appl. Microbiol. 32: 331–335
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
Whitehouse LW & Ecobichon DJ (1975) Paraoxon formation and hydrolysis by mammalian liver. Pestic. Biochem. Physiol. 5: 314–322
Wiriishi HK & Gold M (1992) Manganese (II) oxidation by manganese peroxidase from the basidiomycete Phanerochate chrisosporium. J. Biol. Chem. 267: 23688–23695
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
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
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
Issue Date:
DOI: https://doi.org/10.1023/A:1027316610450