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Plant cytochrome P450-mediated herbicide metabolism

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Abstract

In the last two decades it has become apparent that enzymes of the P450 monooxygenase (P450) superfamily are responsible for the Phase I metabolism of numerous herbicides representing several classes of organic compounds. The majority of experimental evidence for P450 involvement in herbicide metabolism has been derived from in vitro studies in which the catalytic activity of plant microsomes towards herbicidal substrates was measured in the presence of various P450 inhibitors and activators. While the studies with microsomes elicited much appreciation for the pivotal roles of plant P450s in herbicide metabolism, detailed characterization of these enzymes only became possible after the isolation of genes encoding specific isoforms responsible for herbicide conversion. Several lines of evidence suggest that the development of herbicide resistance in weeds by enhanced detoxification is frequently associated with elevated levels of P450 activity. Enhanced detoxification-based herbicide resistance is particularly difficult to control, because it can involve resistance to multiple, chemically unrelated classes of herbicides. Continued research efforts are aimed at elucidating the role of P450s in the metabolic fates of herbicides in plants and the development of herbicide resistance in weeds. Recent advances made in the isolation and genetic manipulation of P450 enzymes have created new opportunities for their application in engineering herbicide tolerance and bioremediation.

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References

  • Abecassis V, Pompon D, Truan G (2000) High efficiency family shuffling based on multi-step PCR and in vivo DNA recombination in yeast: statistical and functional analysis of a combinatorial library between human cytochrome P450 1A1 and 1A2. Nucl Acids Res 28:e88

    Article  PubMed  CAS  Google Scholar 

  • Abecassis V, Urban P, Aggerbeck L, Truan G, Pompon D (2003) Exploration of natural and artificial sequence spaces: towards a functional remodeling of membrane-bound cytochrome P450. Biocatal Biotransfor 21:55–66

    Article  CAS  Google Scholar 

  • Aguiar M, Masse R, Gibbs BF (2005) Regulation of cytochrome P450 by posttranslational modification. Drug Metab Rev 37:379–404

    PubMed  CAS  Google Scholar 

  • Apel K, Hirt H (2004) Reactive oxygen species: metabolism, oxidative stress, and signal transduction. Annu Rev Plant Biol 55:373–399

    Article  PubMed  CAS  Google Scholar 

  • Arabidopsis Genome I (2000) Analysis of the genome sequence of the flowering plant Arabidopsis thaliana. Nature 408:796–815

    Google Scholar 

  • Baerg RJ, Barrett M, Polge ND (1996) Insecticide and insecticide metabolite interactions with cytochrome P450 mediated activities in maize. Pestic Biochem Physiol 55:10–20

    Article  PubMed  CAS  Google Scholar 

  • Baerson SR, Sanchez-Moreiras A, Pedrol-Bonjoch N, Schulz M, Kagan IA, Agarwal AK, Reigosa MJ, Duke SO (2005) Detoxification and transcriptome response in Arabidopsis seedlings exposed to the allelochemical benzoxazolin-2(3H)-one. J Biol Chem 280:21867–21881

    Article  PubMed  CAS  Google Scholar 

  • Barrett M (2000) The role of cytochrome P450 enzymes in herbicide metabolism. In: Cobb AH, Kirkwood RC (eds) Herbicides and their Mechanisms of Action. CRC Press LLC, Boca Raton, pp 25–37

    Google Scholar 

  • Barrett M, Polge N, Baerg RJ, Bradshaw L, Poneleit C (1997) Role of cytochrome P-450s in herbicide␣metabolism and selectivity and multiple herbicide metabolizing cytochrome P-450 activities in␣maize. In: Hatzios KK (ed) Regulation of enzymatic systems detoxifying xenobiotics in plants.␣Kluwer Academic Publishers, Dordrecht, pp 35–51

    Google Scholar 

  • Barta IC, Dutka F (1991) Influence of 1-aminobenzotriazole (ABT) derivatives on the toxicity of EPTC to monocotyledonous plants. Weed Res 31:89–95

    Article  CAS  Google Scholar 

  • Batard Y, LeRet M, Schalk M, Robineau T, Durst F, Werck-Reichhart D (1998) Molecular cloning and functional expression in yeast of CYP76B1, a xenobiotic-inducible 7-ethoxycoumarin O-de-ethylase from Helianthus tuberosus. Plant J 14:111–120

    Article  PubMed  CAS  Google Scholar 

  • Bell SG, Chen X, Xu F, Rao Z, Wong L (2003) Engineering substrate recognition in catalysis by cytochrome P450cam. Biochem Soc Trans 31:558–562

    Article  PubMed  CAS  Google Scholar 

  • Bode M, Haas M, Faymonville T, Thiede B, Schuphan I, Schmidt B (2006) Biotransformation of metamitron by human P450 expressed in transgenic tobacco cell cultures. J Environ Sci Heal B 41:201–222

    CAS  Google Scholar 

  • Bode M, Stobe P, Thiede B, Schuphan I, Schmidt B (2004) Biotransformation of atrazine in transgenic tobacco cell culture expressing human P450. Pest Manag Sci 60:49–58

    Article  PubMed  CAS  Google Scholar 

  • Cabello-Hurtado F, Batard Y, Salaun JP, Durst F, Pinot F, Werck-Reichhart D (1998) Cloning, expression in yeast, and functional characterization of CYP81B1, a plant cytochrome P450 that catalyzes in-chain hydroxylation of fatty acids. J Biol Chem 273:7260–7267

    Article  PubMed  CAS  Google Scholar 

  • Canivenc MC, Cagnac B, Cabanne F, Scalla R (1989) Induced changes of chlorotoluron metabolism in wheat cell-suspension cultures. Plant Physiol Bioch 27:193–201

    CAS  Google Scholar 

  • Carmichael AB, Wong LL (2001) Protein engineering of Bacillus megaterium CYP102 – the oxidation of polycyclic aromatic hydrocarbons. Eur J Biochem 268:3117–3125

    Article  PubMed  CAS  Google Scholar 

  • Cole DJ, Owen WJ (1987) Influence of monooxygenase inhibitors on the metabolism of the herbicides chlortoluron and metolachlor in cell-suspension cultures. Plant Sci 50:13–20

    Article  CAS  Google Scholar 

  • Coupland D, Lutman PJW, Heath C (1990) Uptake, translocation, and metabolism of mecoprop in a sensitive and a resistant biotype of Stellaria-media. Pestic Biochem Physiol 36:61–67

    Article  CAS  Google Scholar 

  • Davies J, Caseley JC (1999) Herbicide safeners: a review. Pestic Sci 55:1043–1058

    CAS  Google Scholar 

  • Davies J, Caseley JC, Jones OTG, Barrett M, Polge ND (1998) Mode of action of naphthalic anhydride as a safener for the herbicide AC 263222 in maize. Pestic Sci 52:29–38

    Article  CAS  Google Scholar 

  • Didierjean L, Gondet L, Perkins R, Lau SMC, Schaller H, O’Keefe DP, Werck-Reichhart D (2002) Engineering herbicide metabolism in tobacco and Arabidopsis with CYP76B1, a cytochrome P450 enzyme from Jerusalem artichoke. Plant Physiol 130:179–189

    Article  PubMed  CAS  Google Scholar 

  • Diehl KE, Stoller EW, Barrett M (1995) In-vivo and in-vitro inhibition of nicosulfuron metabolism by terbufos metabolites in maize. Pestic Biochem Physiol 51:137–149

    Article  CAS  Google Scholar 

  • Durst F, Benveniste I, Lesot A, Salaun JP, Reichhart D-P (1997) Induction of plant cytochrome P450. In: Hatzios KK (ed) Regulation of enzymatic systems detoxifying xenobiotics in plants. NATO ASI Series, Kluwer, Dordrecht, The Netherlands

  • Feng PCC, Rao SR, Schafer DE (1995) Inhibition of thiazopyr metabolism in plant seedlings by inhibitors of monooxygenases. Pestic Sci 45:203–207

    Article  CAS  Google Scholar 

  • Ferhatoglu Y, Avdiushko S, Barrett M (2005) The basis for the safening of clomazone by phorate insecticide in cotton and inhibitors of cytochrome P450s. Pestic Biochem Physiol 81:59–70

    Article  CAS  Google Scholar 

  • Fischer AJ, Bayer DE, Carriere MD, Ateh CM, Yim KO (2000) Mechanisms of resistance to bispyribac-sodium in an Echinochloa phyllopogon accession. Pestic Biochem Physiol 68:156–165

    Article  CAS  Google Scholar 

  • Fonné-Pfister R, Gaudin J, Kreuz K, Ramsteiner K, Ebert E (1990) Hydroxylation of primisulfuron by an inducible cytochrome-P450-dependent monooxygenase system from maize. Pestic Biochem Physiol 37:165–173

    Article  Google Scholar 

  • Fonné-Pfister R, Kreuz K (1990) Ring-methyl hydroxylation of chlortoluron by an inducible cytochrome P450-dependent enzyme from maize. Phytochemistry 29:2793–2796

    Article  Google Scholar 

  • Forthoffer N, Helvig C, Dillon N, Benveniste I, Zimmerlin A, Tardif F, Salaun JP (2001) Induction and inactivation of a cytochrome P450 confering herbicide resistance in wheat seedlings. Eur J Drug Metab Pharmacokinet 26:9–16

    Article  PubMed  CAS  Google Scholar 

  • Frear DS, Swanson HR (1996) Cytochrome P450-dependent hydroxylation of prosulfuron (CGA 152005) by wheat seedling microsomes. J Agric Food Chem 44:3658–3664

    Article  CAS  Google Scholar 

  • Frear DS, Swanson HR, Tanaka FS (1969) N-Demethylation of substituted 3-(phenyl)-1-methylureas – isolation and characterization of a microsomal mixed function oxidase from cotton. Phytochemistry 8:2157–2169

    Article  CAS  Google Scholar 

  • Frear DS, Swanson HR, Tanaka FS (1993) Metabolism of flumetsulam (DE-498) in wheat, corn, and barley. Pestic Biochem Physiol 45:178–192

    Article  CAS  Google Scholar 

  • Frear DS, Swanson HR, Thalacker FW (1991) Induced microsomal oxidation of diclofop, triasulfuron, chlorsulfuron, and linuron in wheat. Pestic Biochem Physiol 41:274–287

    Article  CAS  Google Scholar 

  • Glassgen WE, Komossa D, Bohnenkamper O, Haas M, Hertkorn N, May RG, Szymczak W, Sandermann H (1999) Metabolism of the herbicide isoproturon in wheat and soybean cell suspension cultures. Pestic Biochem Physiol 63:97–113

    Article  CAS  Google Scholar 

  • Glombitza S, Dubuis PH, Thulke O, Welzl G, Bovet L, Gotz M, Affenzeller M, Geist B, Hehn A, Asnaghi C, Ernst D, Seidlitz HK, Gundlach H, Mayer KF, Martinoia E, Werck-Reichhart D, Mauch F, Schaffner AR (2004) Crosstalk and differential response to abiotic and biotic stressors reflected at the transcriptional level of effector genes from secondary metabolism. Plant Mol Biol 54:817–835

    Article  PubMed  CAS  Google Scholar 

  • Gonzalez FJ (1988) The molecular-biology of cytochrome P450s. Pharmacol Rev 40:243–288

    PubMed  CAS  Google Scholar 

  • Gronwald JW (1989) Influence of herbicide safeners on herbicide metabolism. In: Hatzios KK, Hoagland RE (eds) Crop safeners for herbicides. Academic Press, pp 103–128

  • Haack AE, Balke NE (1994) Enhancement of microsomal bentazon 6-hydroxylase and cinnamic acid 4-hydroxylase activities from grain-sorghum shoots. Pestic Biochem Physiol 50:92–105

    Article  CAS  Google Scholar 

  • Hatzios KK (1983) Herbicide antidotes – development, chemistry, and mode of action. Adv Agron 36:265–316

    CAS  Google Scholar 

  • Hatzios KK (1991) An overview of the mechanisms of action of herbicide safeners. Z Naturforsch C 46:819–827

    CAS  Google Scholar 

  • Hatzios KK (1997) Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants: A Brief Overview and Directions for Future Research. In: Hatzios KK (eds) Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. Kluwer Academic Publishers, Dordrecht, pp 1–5

    Google Scholar 

  • Hatzios KK, Burgos N (2004) Metabolism-based herbicide resistance: regulation by safeners. Weed Sci 52:454–467

    Article  CAS  Google Scholar 

  • Helvig C, Tardif FJ, Seyer A, Powles SB, Mioskowski C, Durst F, Salaun JP (1996) Selective inhibition of a cytochrome P450 enzyme in wheat that oxidizes both the natural substrate lauric acid and the synthetic herbicide diclofop. Pestic Biochem Physiol 54:161–171

    Article  CAS  Google Scholar 

  • Hidayat I, Preston C (2001) Cross-resistance to imazethapyr in a fluazifop-P-butyl-resistant population of Digitaria sanguinalis. Pestic Biochem Physiol 71:190–195

    Article  CAS  Google Scholar 

  • Hinz JRR, Owen MDK, Barrett M (1997) Nicosulfuron, primisulfuron, and bentazon hydroxylation by corn (Zea mays), woolly cupgrass (Eriochloa villosa), and shattercane (Sorghum bicolor) cytochrome P-450. Weed Sci 45:474–480

    CAS  Google Scholar 

  • Hirose S, Kawahigashi H, Ozawa K, Shiota N, Inui H,␣Ohkawa H, Ohkawa Y (2005) Transgenic rice␣containing human CYP2B6 detoxifies various classes of herbicides. J Agric Food Chem 53:3461–3467

    Article  PubMed  CAS  Google Scholar 

  • Inui H, Ohkawa H (2005) Herbicide resistance in transgenic plants with mammalian P450 monooxygenase genes. Pest Manag Sci 61:286–291

    Article  PubMed  CAS  Google Scholar 

  • Jablonkai I, Hatzios KK (1994) Microsomal oxidation of the herbicides EPTC and acetochlor and of the safener MG-191 in maize. Pestic Biochem Physiol 48:98–109

    Article  CAS  Google Scholar 

  • Kawahigashi H, Hirose S, Inui H, Ohkawa H, Ohkawa Y␣(2005a) Enhanced herbicide cross-tolerance in␣transgenic rice plants co-expressing human CYP1A1, CYP2B6, and CYP2C19. Plant Sci 168:773–781

    Article  CAS  Google Scholar 

  • Kawahigashi H, Hirose S, Ohkawa H, Ohkawa Y (2006) Phytoremediation of the herbicides atrazine and metolachlor by transgenic rice plants expressing human CYP1A1, CYP2B6, and CYP2C19. J Agric Food Chem 54:2985–2991

    Article  PubMed  CAS  Google Scholar 

  • Kawahigashi H, Hirose S, Ozawa K, Ido Y, Kojima M, Ohkawa H, Ohkawa Y (2005b) Analysis of substrate specificity of pig CYP2B22 and CYP2C49 towards herbicides by transgenic rice plants. Transgenic Res 14:907–917

    Article  CAS  Google Scholar 

  • Koeppe MK, Hirata CM, Brown HM, Kenyon WH, O’Keefe DP, Lau SC, Zimmerman WT, Green JM (2000) Basis of selectivity of the herbicide rimsulfuron in maize. Pestic Biochem Physiol 66:170–181

    Article  CAS  Google Scholar 

  • Kömíves T, Gullner G (2005) Phase I xenobiotic metabolic systems in plants. Z Naturforsch C 60:179–185

    PubMed  Google Scholar 

  • Kreuz K, Fonné-Pfister R (1992) Herbicide-insecticide interaction in maize – malathion inhibits cytochrome-P450-dependent primisulfuron metabolism. Pestic Biochem Physiol 43:232–240

    Article  CAS  Google Scholar 

  • Kreuz K, Gaudin J, Stingelin J, Ebert E (1991) Metabolism of the aryloxyphenoxypropanoate herbicide, CGA-184927, in wheat, barley and maize – differential-effects of the safener, CGA-185072. Z Naturforsch C 46:901–905

    CAS  Google Scholar 

  • Lundqvist E, Johansson I, Ingelman-Sundberg M (1999) Genetic mechanisms for duplication and multiduplication of the human CYP2D6 gene and methods for detection of duplicated CYP2D6 genes. Gene 226:327–338

    Article  PubMed  CAS  Google Scholar 

  • Maneechote C, Preston C, Powles SB (1997) A diclofop-methyl-resistant Avena sterilis biotype with a herbicide-resistant acetyl-coenzyme A carboxylase and enhanced metabolism of diclofop-methyl. Pestic Sci 49:105–114

    Article  CAS  Google Scholar 

  • McFadden JJ, Frear DS, Mansager ER (1989) Aryl hydroxylation of diclofop by a cytochrome-P450 dependent monooxygenase from wheat. Pestic Biochem Physiol 34:92–100

    Article  CAS  Google Scholar 

  • McFadden JJ, Gronwald JW, Eberlein CV (1990) Invitro hydroxylation of bentazon by microsomes from naphthalic anhydride-treated corn shoots. Biochem Biophys Res Commun 168:206–213

    Article  PubMed  CAS  Google Scholar 

  • Moreland DE, Corbin FT (1991) Influence of safeners on the in vivo and in vitro metabolism of bentazon and metolachlor by grain-sorghum shoots – a preliminary-report. Z Naturforsch C 46:906–914

    CAS  Google Scholar 

  • Moreland DE, Corbin FT, Fleischmann TJ, McFarland JE (1995) partial characterization of microsomes isolated from mung bean cotyledons. Pestic Biochem Physiol 52:98–108

    Article  CAS  Google Scholar 

  • Moreland DE, Corbin FT, McFarland JE (1993a) Effects of safeners on the oxidation of multiple substrates by grain-sorghum microsomes. Pestic Biochem Physiol 45:43–53

    Article  CAS  Google Scholar 

  • Moreland DE, Corbin FT, McFarland JE (1993b) Oxidation of multiple substrates by corn shoot microsomes. Pestic Biochem Physiol 47:206–214

    Article  CAS  Google Scholar 

  • Moreland DE, Fleischmann TJ, Corbin FT, McFarland JE (1996) Differential metabolism of the sulfonylurea herbicide prosulfuron (CGA-152005) by plant microsomes. Z Naturforsch C 51:698–710

    CAS  Google Scholar 

  • Mougin C, Cabanne F, Canivenc MC, Scalla R (1990) Hydroxylation and N-demethylation of chlorotoluron by wheat microsomal-enzymes. Plant Sci 66:195–203

    Article  CAS  Google Scholar 

  • Mougin C, Cabanne F, Scalla R (1992) Additional observations on the chlorotoluron hydroxylase and N-demethylase activities in wheat microsomes. Plant Physiol Bioch 30:769–778

    CAS  Google Scholar 

  • Mougin C, Polge N, Scalla R, Cabanne F (1991) Interactions of various agrochemicals with cytochrome-P-450-dependent monooxygenases of wheat cells. Pestic Biochem Physiol 40:1–11

    Article  CAS  Google Scholar 

  • Narusaka Y, Narusaka M, Seki M, Umezawa T, Ishida J, Nakajima M, Enju A, Shinozaki K (2004) Crosstalk in the responses to abiotic and biotic stresses in Arabidopsis: analysis of gene expression in cytochrome P450 gene superfamily by cDNA microarray. Plant Mol Biol 55:327–342

    Article  PubMed  CAS  Google Scholar 

  • O’keefe DP, Tepperman JM, Dean C, Leto KJ, Erbes DL, Odell JT (1994) Plant expression of a bacterial cytochrome-P450 that catalyzes activation of a sulfonylurea pro-herbicide. Plant Physiol 105:473–482

    PubMed  CAS  Google Scholar 

  • Persans MW, Schuler MA (1995) Differential induction of cytochrome P450-mediated triasulfuron metabolism by naphthalic anhydride and triasulfuron. Plant Physiol 109:1483–1490

    Article  PubMed  CAS  Google Scholar 

  • Persans MW, Wang J, Schuler MA (2001) Characterization of maize cytochrome P450 monooxygenases induced in response to safeners and bacterial pathogens. Plant Physiol 125:1126–1138

    Article  PubMed  CAS  Google Scholar 

  • Pierrel MA, Batard Y, Kazmaier M, Mignottevieux C, Durst F, Werck-Reichhart D (1994) Catalytic properties of the plant cytochrome-P450 CYP73 expressed in yeast-substrate-specificity of a cinnamate hydroxylase. Eur J Biochem 224:835–844

    Article  PubMed  CAS  Google Scholar 

  • Polge ND, Barrett M (1995) Characterization of cytochrome P450-mediated chlorimuron ethyl hydroxylation in maize microsomes. Pestic Biochem Physiol 53:193–204

    Article  CAS  Google Scholar 

  • Preston C (2003) Inheritance and linkage of metabolism-based herbicide cross-resistance in rigid ryegrass (Lolium rigidum). Weed Sci 51:4–12

    Article  CAS  Google Scholar 

  • Preston C (2004) Herbicide resistance in weeds endowed by enhanced detoxification: complications for management. Weed Sci 52:448–453

    Article  CAS  Google Scholar 

  • Preston C, Tardif FJ, Christopher JT, Powles SB (1996) Multiple resistance to dissimilar herbicide chemistries in a biotype of Lolium rigidum due to enhanced activity of several herbicide degrading enzymes. Pestic Biochem Physiol 54:123–134

    Article  CAS  Google Scholar 

  • Rishi AS, Munir S, Kapur V, Nelson ND, Goyal A (2004) Identification and analysis of safener-inducible expressed sequence tags in Populus using a cDNA microarray. Planta 220:296–306

    Article  PubMed  CAS  Google Scholar 

  • Robineau T, Batard Y, Nedelkina S, Cabello-Hurtado F, LeRet M, Sorokine O, Didierjean L, Werck-Reichhart D (1998) The chemically inducible plant cytochrome P450 CYP76B1 actively metabolizes phenylureas and other xenobiotics. Plant Physiol 118:1049–1056

    Article  PubMed  CAS  Google Scholar 

  • Romano ML, Stephenson GR, Tal A, Hall JC (1993) The Effect of monooxygenase and glutathione-S-transferase inhibitors on the metabolism of diclofop-methyl and fenoxaprop-ethyl in barley and wheat. Pestic Biochem Physiol 46:181–189

    Article  CAS  Google Scholar 

  • Scott-Craig JS, Casida JE, Poduje L, Walton JD (1998) Herbicide safener-binding protein of maize – purification, cloning, and expression of an encoding cDNA. Plant Physiol 116:1083–1089

    Article  PubMed  CAS  Google Scholar 

  • Shiota N, Nagasawa A, Sakaki T, Yabusaki Y, Ohkawa H (1994) Herbicide-resistant tobacco plants expressing the fused enzyme between rat cytochrome P4501A1 (CYP1A1) and yeast NADPH-cytochrome P450 oxidoreductase. Plant Physiol 106:17–23

    Article  PubMed  CAS  Google Scholar 

  • Siminszky B, Corbin FT, Ward ER, Fleischmann TJ, Dewey RE (1999) Expression of a soybean cytochrome P450 monooxygenase cDNA in yeast and tobacco enhances the metabolism of phenylurea herbicides. Proc Natl Acad Sci USA 96:1750–1755

    Article  PubMed  CAS  Google Scholar 

  • Siminszky B, Freytag AM, Sheldon BS, Dewey RE (2003) Co-expression of a NADPH: P450 reductase enhances CYP71A10-dependent phenylurea metabolism in tobacco. Pestic Biochem Physiol 77:35–43

    Article  CAS  Google Scholar 

  • Siminszky B, Sheldon BS, Corbin FT, Dewey RE (2000) A cytochrome P450 monooxygenase cDNA (CYP71A10) confers resistance to linuron in transgenic Nicotiana tabacum. Weed Sci 48:291–295

    Article  CAS  Google Scholar 

  • Singh S, Kirkwood RC, Marshall G (1998) Effect of ABT on the activity and rate of degradation of isoproturon in susceptible and resistant biotypes of Phalaris minor and in wheat. Pestic Sci 53:123–132

    Article  Google Scholar 

  • Smith AP, DeRidder BP, Guo WJ, Seeley EH, Regnier FE, Goldsbrough PB (2004) Proteomic analysis of Arabidopsis glutathione S-transferases from benoxacor- and copper-treated seedlings. J Biol Chem 279:26098–26104

    Article  PubMed  CAS  Google Scholar 

  • Sterling TM, Balke NE (1990) Bentazon uptake and metabolism by cultured plant cells in the presence of monooxygenase inhibitors and cinnamic acid. Pestic Biochem Physiol 38:66–75

    Article  CAS  Google Scholar 

  • Teutsch HG, Hasenfratz MP, Lesot A, Stoltz C, Garnier JM, Jeltsch JM, Durst F, Werck-Reichhart D (1993) Isolation and sequence of a cDNA-encoding the Jerusalem-artichoke cinnamate 4-hydroxylase, a major plant cytochrome-P450 involved in the general phenylpropanoid pathway. Proc Natl Acad Sci USA 90:4102–4106

    Article  PubMed  CAS  Google Scholar 

  • Thalacker FW, Swanson HR, Frear DS (1994) Characterization, purification, and reconstitution of an inducible cytochrome P450-dependent triasulfuron hydroxylase from wheat. Pestic Biochem Physiol 49:209–223

    Article  CAS  Google Scholar 

  • Topal A, Adams N, Dauterman WC, Hodgson E, Kelly SL (1993) Purification and herbicide metabolism studies on tulip (Tulipa-Gesneriana) cytochrome-P450. Pestic Sci 38:9–15

    Article  CAS  Google Scholar 

  • Veldhuis LJ, Hall LM, O’Donovan JT, Dyer W, Hall JC (2000) Metabolism-based resistance of a wild mustard (Sinapis arvensis L.) biotype to ethametsulfuron-methyl. J Agric Food Chem 48:2986–2990

    Article  PubMed  CAS  Google Scholar 

  • Vila-Aiub MM, Neve P, Powles SB (2005) Resistance cost of a cytochrome P450 herbicide metabolism mechanism but not an ACCase target site mutation in a multiple resistant Lolium rigidum population. New Phytol 167:787–796

    Article  PubMed  CAS  Google Scholar 

  • Walton JD, Casida JE (1995) Specific binding of a dichloroacetamide herbicide safener in maize at a site that also binds thiocarbamate and chloroacetanilide herbicides. Plant Physiol 109:213–219

    Article  PubMed  CAS  Google Scholar 

  • Xiang WS, Wang XJ, Ren TR, Ci SQ (2006) Expression of a wheat cytochrome P450 monooxygenase cDNA in yeast catalyzes the metabolism of sulfonylurea herbicides. Pestic Biochem Physiol 85:1–6

    Article  CAS  Google Scholar 

  • Yamada T, Kambara Y, Imaishi H, Ohkawa H (2000) Molecular cloning of novel cytochrome P450 species induced by chemical treatments in cultured tobacco cells. Pestic Biochem Physiol 68:11–25

    Article  CAS  Google Scholar 

  • Yun MS, Shim IS, Usui K (2001) Involvement of cytochrome P-450 enzyme activity in the selectivity and safening action of pyrazosulfuron-ethyl. Pest Manag Sci 57:283–288

    Article  PubMed  CAS  Google Scholar 

  • Zhong L, Wang K, Tan J, Li W, Li SG (2002) Putative cytochrome P450 genes in rice genome (Oryza sativa L. ssp indica) and their EST evidence. Sci China Ser C-Life Sci 45:512–517

    Article  CAS  Google Scholar 

  • Zimmerlin A, Durst F (1990) Xenobiotic metabolism in plants – aryl hydroxylation of diclofop by a cytochrome-P-450 enzyme from wheat. Phytochemistry 29:1729–1732

    Article  CAS  Google Scholar 

  • Zimmerlin A, Durst F (1992) Aryl hydroxylation of the herbicide diclofop by a wheat cytochrome-P-450 monooxygenase-substrate-specificity and physiological-activity. Plant Physiol 100:874–881

    Article  PubMed  CAS  Google Scholar 

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Siminszky, B. Plant cytochrome P450-mediated herbicide metabolism. Phytochem Rev 5, 445–458 (2006). https://doi.org/10.1007/s11101-006-9011-7

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