Characterization of cytochrome P450-mediated bensulfuron-methyl O-demethylation in rice

Pesticide Biochemistry and Physiology

Volumn 74, Issue 2, 2002, Pages 102-115

  Deng, Fan ^a   Hatzios, Kriton K ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

Bensulfuron methyl; Characterization of rice P450; Cytochrome P450 monooxygenase (P450); Herbicide metabolism; Herbicide safeners; Lemont rice; P450 inducers P450 inhibitors; Purification of rice P450

Indexed keywords

ORYZA SATIVA;

EID: 0036826647     PISSN: 00483575     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0048-3575(02)00151-7     Document Type: Article

References (38)

1. H. Inui, N. Shiota, Y. Ido, T. Inoue, S. Hirose, H. Kawahigashi, Y. Ohkawa, H. Ohkawa, Herbicide metabolism and tolerance in transgenic rice plants expressing human CYP2C9 and CYP2C19, Pestic. Biochem. Physiol. 71 (2001) 156-169.
2. S. Takeda, T. Yuyama, R.C. Ackerson, R.C. Weigel, Selection of rice herbicides from several sulfonylurea compounds, Weed Res. (Japan) 30 (1985) 278-283.
3. S. Takeda, D.L. Erbes, P.B. Sweetser, J.V. Hay, T. Yuyama, Mode of herbicidal and selective action of DPX-F5384 between rice and weeds, Weed Res. (Japan) 31 (1986) 157-163.
4. H.M. Brown, Mode of action, crop selectivity, and soil relations of the sulfonylurea herbicides, Pestic. Sci. 29 (1990) 263-281.
5. M.K. Koeppe, H.M. Brown, Sulfonylurea herbicide plant metabolism and crop selectivity, Agro-Food-Ind. Hi-Tech 6 (1995) 9-14.
6. Yuyama, P.B. Sweetser, R.C. Ackerson, S. Takeda, Safening of DPX-F5384 on rice by combination with thiocarbamate herbicides, Weed Res. (Japan) 31 (1986) 164-170.
7. T. Yuyama, S. Shirakura, K. Ishizuka, Mode of safener action of dimepiperate, a thiocarbamate herbicide on bensulfuron methyl activity, Z. Naturforsch. C 46 (1991) 887-892.
8. H. Omokawa, J. Wu, K.K. Hatzios, Mechanism of safening action of dymuron and its two monomethyl analogues against bensulfuron-methyl injury to rice (Oryza sativa), Pestic. Biochem. Physiol. 55 (1996) 54-63.
9. G.P. Bolwell, K. Bozak, A. Zimmerlin, Plant cytochrome P450, Phytochemistry 37 (1994) 1491-1506.
10. C. Chapple, Molecular-genetic analysis of plant cytochrome P450-dependent monooxygenases, Annu. Rev. Plant Physiol. Plant Mol. Biol. 49 (1998) 311-343.
11. F. Durst, D.P. O'Keffe, Plant cytochrome P450: an overview, Drug Metab. Drug Interact. 12 (1995) 171-187.
12. M.A. Schuler, Plant cytochrome P450 monooxygenases, Crit. Rev. Plant Sci. 15 (1996) 235-284.
13. M. Kasakuchi, K. Mihara, R. Sato, Signal recognition particle is required for co-translational insertion of cytochrome P-450 into microsomal membranes, Proc. Natl. Acad. Sci. USA 81 (1984) 3361-3364.
14. D.P. O'Keefe, A functional genomics approach to the enzymes of plant xenobiotics, J. Pestic. Sci. 25 (2000) 182-183.
15. W.-M. Cou, T. Kutchan, Enzymatic oxidations in the biosynthesis of complex alkaloids, Plant J. 15 (1998) 289-300.
16. M. Barrett, Metabolism of herbicides by cytochrome P450 in corn, Drug Metab. Drug Interact. 12 (1995) 299-315.
17. DS. Frear, Wheat microsomal cytochrome P450 monooxygenases: characterization and importance in the metabolic selectivity of wheat herbicides, Drug Metab. Drug Interact. 12 (1995) 329-357.
18. C.P. Mougin, M.-F. Corio-Costet, D. Werck-Reichhart, Plant and fungal cytochrome P-450s: their role in pesticide metabolism, in: J.C. Hall, R.E. Hoagland, R.M. Zablotowicz (Eds.), Pesticide Biotransfromation in Plants and Microorganisms: Similarities and Divergences, ACS Symposium Series, 777, American Chemical Society, Washington, DC, 2001, pp. 166-181.
19. B. Siminszky, F.T. Corbin, E.J. Ward, T.J. Fleischmann, R.E. Dewey, Expression of a soybean P450 monooxygenase cDNA in yeast and tobacco enhances the metabolism of phenylurea herbicides, Proc. Natl. Acad. Sci. USA 96 (1999) 1750-1755.
20. T. Robineau, Y. Batard, S. Nedelkina, F. Corbello-Hurtado, M. LeRet, O. Sorokine, L. Didierjean, D. Werck-Reeichhart, The chemically-inducible plant cytochrome P450 CYP76B1 actively metabolizes phenylureas and other xenobiotics, Plant Physiol. 118 (1998) 1049-1056.
21. D. Werck-Reichhart, A. Hehn, L. Didierjean, Cytochrome P450 for engineering herbicide tolerance, Trends Pharmacol. Sci. 5 (2000) 116-123.
22. T. Yamada, Y. Kambara, H. Imashi, H. Ohkawa, Molecular cloning of novel cytochrome P450 species induced by chemical treatments in tobacco cells, Pestic. Biochem. Physiol. 68 (2000) 11-25.
23. Y. Batard, M. Schalk, M-A. Pierrel, A. Zimmerlin, F. Durst, D. Werck-Reichhart, Regulation of the cinnamate 4-hydroxylase (CYP73A1) in Jerusalem artichoke tubers in response to and chemical treatments, Plant Physiol. 113 (1997) 951-959.
24. D. Werck-Reichhart, Cytochromes P450 in phenylpropanoid metabolism, Drug Metab. Drug Interact. 12 (1995) 221-243.
25. K.K. Hatzios, Herbicide safeners and synergists, in: T. Roberts (Ed.), Metabolism of Agrochemicals in Plants, Wiley, Chichester, UK, 2000, pp. 259-294.
26. C. Mougin, F. Cabane, R. Scalla, Additional observations on the chlortoluron hydroxylase and N-demethylase activities in wheat microsomes, Plant Physiol. Biochem. 30 (1992) 769-778.
27. C. Mougin, N. Polge, R. Scalla, F. Cabanne, Interaction of various agrochemicals with cytochrome P-450 dependent monooxygenases of wheat cells, Pestic. Biochem. Physiol. 40 (1991) 1-11.
28. I. Jablonkai, K.K. Hatzios, Microsomal oxidation of the herbicides EPTC and acetochlor and of the safener MG-191 in maize, Pestic. Biochem. Physiol. 48 (1994) 98-109.
29. N.D. Polge, M. Barrett, Characterization of cytochrome P450-mediated clorimuron ethyl hydroxylation in maize microsomes, Pestic. Biochem. Physiol. 53 (1995) 1193-1204.
30. M. Bradford, A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding, Anal. Biochem. 72 (1976) 248-254.
31. G. Collu, N. Unver, A.M.G. Peltenburg-Looman, R.v.d. Heijden, R. Verpoorte, J. Memelink, Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis, FEBS Lett. 508 (2001) 215-220.
32. C.S. Kwon, J.J. Kells, D. Penner, Combined effects of acetolactate synthase-inhibiting herbicides with terbufos and piperonyl butoxide on corn (Zea mays) and soybean (Glycine max), Weed Technol. 9 (1995) 696-702.
33. M.S. Yum, F. Deng, K. Usui, O-dealkylation of coumarin ethers and effects of inducers, inhibitors and sulfonylureas on rice cytochrome P-450, J. Weed Sci. Tech. 44 (1999) 341-348.
34. M.S. Yum, I.S. Shim, K. Usui, Differential activity of O-dealkylation by cytochrome P-450 in rice and Cyperus serotinus, J. Weed Sci. Tech. 45 (2000) 39-42.
35. J. Winter, C. Eckerskorn, R. Waditschatka, H. Keyser, A microsomal ecdysome-binding cytochrome P450 from the insect Locusta migratoria purified by sequential use of type-II and type-I ligands, Biol. Chem. 382 (2001) 1541-1549.
36. R. Stadler, M.H. Zenk, The purification and characterization of a unique cytochrome P450 enzyme from Berberis stolonifera plant cell cultures, J. Biol. Chem. 268 (1992) 823-831.
37. C. Grand, Ferulic acid 5-hydroxylase: a new cytochrome P450-dependent enzyme from higher plant microsomes involved in lignin biosynthesis, FEBS Lett. 169 (1984) 7-11.
38. Y. Utsunomiya, T. Nakayama, H. Oohira, R. Hirate, T. Mori, F. Kawai, T. Ueda, Purification and inactivation by substrate of an allene oxide synthase (CYP74) from corn (Zea mays L.) seeds, Phytochemistry 533 (2000) 319-323.