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Biodegradation of the chlorophenoxy herbicide (R)-(+)-mecoprop by Alcaligenes denitrificans

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Abstract

An Alcaligenes denitrificans strain capable of utilizing theherbicide (R)-(+)-2(2-methyl-4-chlorophenoxy)propionicacid (mecoprop) as a sole carbon source was isolated fromsoil and cultured in liquid medium. Crude cell extracts of thebacterium were utilized in spectrophotometric assays toelucidate a biochemical pathway for degradation ofmecoprop. Results indicated a reaction sequence analogousto the degradation of 2,4-dichlorophenoxyacetic acid (2,4-D).GC-MS analysis provided direct evidence for thebiotransformation of mecoprop to the transient metabolite4-chloro-2-methylphenol (MCP). No NADPH-dependentactivity was observed during this reaction. Pyruvate wasverified as the second product derived from the aliphatic sidechain of mecoprop. MCP was subsequently transformed to asubstituted catechol by an NADPH-dependentmonooxygenase. When grown on mecoprop, A.denitrificans was adapted to oxidize catechol and its 4- and3-methylated derivatives indicating the broad substratespecificity of catechol dioxygenase. The microorganism wasdemonstrated to adopt the ortho mechanism of aromaticcleavage which resulted in the formation of2-methyl-4-carboxymethylene but-2-en-4-olide, a reactionintermediate of the β-ketoadipate pathway.

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References

  • Abbott MT & Udenfriend S (1974) Ketoglutarate-coupled dioxygenases. In: Hayaishi O (ntEd) Molecular Mechanisms of Oxygen Activation (pp 167–214). Academic Press, London

    Google Scholar 

  • Anonymous (1992) Produce Farmstat Survey

  • Bollag JM, Helling CS & Alexander M (1967) Metabolism of 4-chloro-2-methylphenoxyacetic acid by soil bacteria.Appl.Microbiol. 15: 1393–1398-(1968a) 2,4-D metabolism: enzymatic hydroxylation of chlorinated phenols. J. Agr. Food Chem. 16: 826–828

    Google Scholar 

  • Bollag JM, Briggs GG, Dawson JE & Alexander M (1968b) 2,4-D metabolism: enzymatic degradation of chlorocatechols. J. Agr. Food Chem. 16: 829–833

    Google Scholar 

  • Chaudhry GR & Chapalamadugu S (1991) Biodegradation of halogenated organic compounds. Microbiol. Rev. 55: 59–79

    Google Scholar 

  • Commandeur LCM & Parsons JR(1990) Degradation of halogenated aromatic compounds. Biodegradation 1: 207–220

    Google Scholar 

  • Dagley S (1987) Lessons from biodegradation. Annu. Rev. Microbiol. 41: 1–23

    Google Scholar 

  • Evans WC, Smith BSW, Moss P & Fernley HN (1971a) Bacterial metabolism of 4-chlorophenoxyacetate. Biochem. J. 122: 509–517

    Google Scholar 

  • Evans WC, Smith BSW, Fernley HN & Davies JI (1971b) Bacterial metabolism of 2,4-dichlorophenoxyacetate. Biochem. J. 122: 543–552

    Google Scholar 

  • Fukumori F & Hausinger RP (1993) Alcaligenes eutrophusJMP134 '2,4-dichlorophenoxyacetate monooxygenase' is an ketoglutarate-dependent dioxygenase. J. Bacteriol. 175: 2083–2086

    Google Scholar 

  • Gamar Y & Gaunt JK (1971) Bacterial metabolism of 4-chloro-2-methylphenoxyacetate (MCPA): formation of glyoxylate by side-chain cleavage. Biochem. J. 122: 527–531

    Google Scholar 

  • Gaunt JK & Evans WC (1971a) Metabolism of 4-chloro-2-methylphenoxyacetate by a soil pseudomonad: Preliminary evidence for the metabolic pathway. Biochem. J. 122: 519–526-(1971b) Metabolism of 4-chloro-2-methylphenoxyacetate by a soil pseudomonad. Ring-fission, lactonizing and delactonizing enzymes. Biochem. J. 122: 533-542

    Google Scholar 

  • H¨aggblom MM (1992) Microbial breakdown of halogenated aromatic pesticides and related compounds. FEMS Microbiol. Rev. 103: 29–72

  • Haigler BE, Nishino SF & Spain JC (1988) Degradation of 1, 2-dichlorobenzene by aPseudomonassp.Appl. Environ.Microbiol. 54: 294–300

    Google Scholar 

  • Hegeman GD (1966) Synthesis of the enzymes of the mandelate pathway by Pseudomonas putida. J. Bacteriol. 91: 1140–1154

    Google Scholar 

  • Higson FK & Focht DD (1992) Utilization of 3-chloro-2-methylbenzoic acid by Pseudomonas cepaciaMB2 through the metafission pathway. Appl. Environ. Microbiol. 58: 2501–2504

    Google Scholar 

  • Kilby (1948) The bacterial oxidation of phenol to α-keto-adipic acid. Biochem. J. 43: V–VI

    Google Scholar 

  • Kilpi S (1980) Degradation of some phenoxy acid herbicides by mixed cultures of bacteria from soil treated with 2-(2-methyl-4-chloro)phenoxypropionic acid. Microbial Ecol. 6: 261–270

    Google Scholar 

  • Lindholm L, Backstr¨om V & Kilpi S (1982) Degradation of mecoprop in soil. Acta Agr. Scandinavica 32: 429–432

    Google Scholar 

  • Loos MA, Roberts RN & Alexander M(1967a) Phenols as intermediates in the decomposition of phenoxyacetates by an Arthrobactersp. Canadian J. Microbiol. 13: 679–690-(1967b) Formation of 2,4-dichlorophenol and 2,4-dichloroanisole from 2,4-dichlorophenoxyacetate by Arthrobactersp. Canadian J. Microbiol. 13: 691–699

    Google Scholar 

  • Loos MA (1975) Phenoxyalkanoic acids. In: Kearney PC & Kaufman DD (Eds) Herbicides: Their Chemistry, Degradation and Mode of Action, Vol 1 (pp 34-57). Marcel Dekker, New York

    Google Scholar 

  • MacRae IC, Alexander M & Rovira AD (1963) The decomposition of 4-(2, 4-dichlorophenoxy)butyric acid by Flavobacteriumsp. J. Gen. Microbiol. 32: 69–76

    Google Scholar 

  • Oh K & Tuovinen OH (1991a) Bacterial degradation of phenoxy herbicide mixtures 2,4-D and MCPP. Bull. Environ. Contam. Toxicol. 47: 1–8-(1991b) Detection and identification of substituted phenols as intermediates of concurrent bacterial degradation of the phenoxy herbicides MCPP and 2,4-D. Microbiol. Lett. 79: 141–146-(1994) Biodegradation of the phenoxy herbicides MCPP and 2,4-D in fixed-film column reactors. Int. Biodet. Biodeg. 33: 93–99

    Google Scholar 

  • Ornston LN & Stanier RY (1966) The conversion of catechol and protocatechuate to β-ketoadipate by Pseudomonas putida. J. Biol. Chem. 241: 3776–3785

    Google Scholar 

  • Pandell AJ (1976) Enzyme-like aromatic oxidations. Metalcatalysed peracetic acid oxidation of phenol and catechol to cis, cismuconic acid. J. Org. Chem. 41: 3992–3996

    Google Scholar 

  • Pieper DH, Stadlerfritzsche K, Engesser KH, Knackmuss HJ (1993) Metabolism of 2-chloro-4-methylphenoxyacetate by Alcaligenes eutrophusJMP-134. Arch. Microbiol. 160: 169–178

    Google Scholar 

  • Sandmann E & Loos MA (1988) Aromatic metabolism of a 2,4-D degrading Arthrobactersp. Canadian J. Microbiol. 34: 125–130

    Google Scholar 

  • Schl¨omann M (1994) Evolution of chlorocatechol catabolic pathways. Biodegradation 5: 301–321

    Google Scholar 

  • Sinton GL, Fan LT, Erickson LE & Lee SM (1986) Biodegradation of 2,4-D and related xenobiotic compounds. Enzyme Microbial Technol. 8: 395–403

    Google Scholar 

  • Stanier RY, Palleroni NJ & Doudoroff M (1966) The aerobic pseudomonads: a taxonomic study.J. Gen. Microbiol. 43: 159–271

    Google Scholar 

  • Tett VA, Willetts AJ & Lappin-Scott HM (1994) Enantioselective degradation of the herbicide mecoprop [2-(2-methyl-4-chlorophenoxy)propionic acid] by mixed and pure bacterial cultures. FEMS Microbiol. Ecol. 14: 191–200

    Google Scholar 

  • Tiedje JM & Alexander M (1969) Enzymatic cleavage of the ether bond of 2,4-dichlorophenoxyacetate. J. Agr. Food Chem. 17: 1080–1084

    Google Scholar 

  • Tiedje JM, D uxbury JM, Alexander M & Dawson JE (1969) 2,4-D metabolism: pathway of degradation of chlorocatechols by Arthrobactersp. J. Agr. Food Chem. 17: 1021–1026

    Google Scholar 

  • Worsey MJ & Williams PA (1975) Metabolism of toluene and xylenes by Pseudomonas putida(arvilla) mt-2: evidence for a new function of the TOL plasmid. J. Bacteriol. 124: 7–13

    Google Scholar 

  • Worthing CR & Walker SB (1991) The Pesticide Manual: A World Compendium. BCPC Publications, Bracknell, UK

Download references

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Authors and Affiliations

  1. Research School of Biosciences, University of Kent at Canterbury, Canterbury, CT2 7NJ, Kent, UK

    Vanessa A. Tett

  2. Department of Biological Sciences, Exeter University, Hatherly Laboratories, Exeter, EX4 4PS, Devon, UK

    Andrew J. Willetts & Hilary M. Lappin-Scott

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  1. Vanessa A. Tett
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  2. Andrew J. Willetts
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  3. Hilary M. Lappin-Scott
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Tett, V.A., Willetts, A.J. & Lappin-Scott, H.M. Biodegradation of the chlorophenoxy herbicide (R)-(+)-mecoprop by Alcaligenes denitrificans. Biodegradation 8, 43–52 (1997). https://doi.org/10.1023/A:1008262901202

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