p-hydroxyphenylpyruvate dioxygenase inhibitor-resistant plants

Pest Management Science

Volumn 61, Issue 3, 2005, Pages 269-276

  Matringe, Michel ^a   Sailland, Alain ^b   Pelissier, Bernard ^b   Rolland, Anne ^b   Zink, Olivier ^b  

^a CNRS   (France)

^b BAYER AG   (Germany)

Author keywords

Herbicide resistance; P hydroxyphenylpyruvate dioxygenase; Transgenic crops

Indexed keywords

4 HYDROXYPHENYLPYRUVATE DIOXYGENASE; 4 HYDROXYPHENYLPYRUVATE DIOXYGENASE INHIBITOR; 4 HYDROXYPHENYLPYRUVIC ACID; ALPHA TOCOPHEROL; ALPHA TOCOTRIENOL; HERBICIDE; HOMOGENTISIC ACID; ISOXAZOLE DERIVATIVE; MUTANT PROTEIN; PLASTOQUINONE; PREPHENATE DEHYDROGENASE; PYROXAZOLE DERIVATIVE; PYRUVIC ACID; TRIKETONE DERIVATIVE; UNCLASSIFIED DRUG;

ENZYME;

BACTERIAL GENE; BLEACHING; CONFERENCE PAPER; CROP; DRUG EFFECT; DRUG POTENCY; DRUG TARGETING; ENZYME INHIBITION; GENE OVEREXPRESSION; GENE THERAPY; GENETIC ENGINEERING; GRASS; HERBICIDE RESISTANCE; HPPD GENE; MAIZE; NONHUMAN; PDH GENE; PLANT; PLANT LEAF; RICE; TRANSGENIC PLANT; WEED; WEED CONTROL; YEAST;

4-HYDROXYPHENYLPYRUVATE DIOXYGENASE; DRUG RESISTANCE; GENE EXPRESSION; GENETIC ENGINEERING; HERBICIDES; PLANTS; PLANTS, GENETICALLY MODIFIED; PSEUDOMONAS FLUORESCENS;

BACTERIA (MICROORGANISMS); ZEA MAYS;

EID: 14644425423     PISSN: 1526498X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ps.997     Document Type: Conference Paper

References (61)

1. Lee DL, Knudsen CG, Michaely WJ, Chin H-L, Nguyen NH, Carter CG, Cromartie TH, Lake, BH, Shribbs JM and Fraser T, The structure-activity relationships of the triketone class of HPPD herbicides. Pestic Sci 54:377-384 (1998).
2. Romagni JG, Meazza G, Nanayakkara NPD and Dayan FE, The phytotoxic lichen metabolite, usnic acid, is a potent inhibitor of plant p-hydroxyphenylpyruvate dioxygenase. FEBS Lett 480:301-305 (2000).
3. Mayonado DJ, Hatzios KK, Orcut DM and Wilson HP, Evaluation of the mechanism of action of the bleaching herbicide SC-0051 by HPLC analysis. Pestic Biochem Physiol 35:138-145 (1989).
4. Soeda T and Uchida T, Inhibition of pigment synthesis by 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-dichlorobenzoyl)-5-hydroxypyrazole, norflurazon, and new herbicidal com-pounds in radish and flatsedge plants. Pestic Biochem Physiol 29:35-42 (1987).
5. Sandman G, Böger P and Kumita I, Atypical inhibition of phytoene desaturation by 2-(4-chloro-2-nitrobenzoyl)-5,5-dimethylcyclo-hexane-1,3-dione. Pestic Sci 30:353-355 (1990).
6. Lock EA, Ellis MK, Provan WM and Smith LL, The effect of NTBC on enzymes involved in tyrosine catabolism in the rat. Toxicologist 14:826-832 (1994).
7. Lindstedt S, Holme E, Lock EA, Hjalmarson O and Strandvik B, Treatment of hereditary tyrosinemia type I by inhibition of 4-hydroxyphenylpyruvate dioxygenase. Lancet 340:813-817 (1992).
8. Lindblad B, Lindstedt S and Steen G, On the enzymic defects in hereditary tyrosinemia. Proc Natl Acad Sci USA 74:4641-4645 (1977).
9. Ellis MK, Lindstedt ST, Lock EA, Markstedt MEH, Mutter LC and Prisbylla MP, Use of 2-(2-nitro-4-trifluoromethyl-benzoyl)-1,3-cyclohexanedione in the treatment of tyrosinemia and pharmaceutical compositions, WO Patent 93/00080 (1993).
10. Prisbylla MP, Onisko BC, Shribbs JM, Adams DO, Liu Y, Ellis MK, Hawkes TR and Mutter, LC, The novel mechanism of action of the herbicidal triketones, in Proc Brighton Crop Prot Conf-Weeds, BCPC, Farnham, Surrey, UK, pp 731-738 (1993).
11. Schulz A, Ort O, Beyer P and Klenig H, SC-0051, a 2-benzoyl-cyclohexane- 1,3-dione bleaching herbicide, is a potent inhibitor of the enzyme p-hydroxyphenylpyruvate dioxygenase. FEBS Lett 318:162-166 (1993).
12. Secor J, Inhibition of barnyardgrass 4-hydroxyphenylpyruvate dioxygenase by sulcotrione. Plant Physiol 106:1429-1433 (1994).
13. Ellis MK, Whiyfield AC, Gowans LA, Auton TR, McLean Provan W, Lock EA, Lee DL and Smith LL, Characterization of the interaction of 2-[2-nitro-4- (trifluoromethyl)benzoyl]-4,4,6,6-tetramethyl-cyclohexane-1,3,5-trione with rat hepatic 4-hydroxyphenylpyruvate dioxygenase. Chem Res Toxicol 9:24-27 (1995).
14. Pallett KE, Little JP, Sheekey M and Veerasekaran P, The mode of action of isoxaflutole: 1. Physiological effects, metabolism and selectivity. Pestic Biochem Physiol 62:113-124 (1998).
15. Mayer MP, Beyer P and Kleinig H, Quinone compounds are able to replace molecular oxygen as terminal electron acceptor in phytoene desaturation in chromoplasts of Narcissus pseudonarcissus L. Eur J Biochem 191:359-363 (1990).
16. Norris SR, Barrette TR and DellaPenna D, Genetic dissection of carotenoid synthesis in Arabidopsis defines plastoquinone as an essential component of phytoene desaturation. Plant Cell 7:2139-2149 (1995).
17. Lindblad B, Lindstedt G and Lindstedt S, The mechanism of enzymatic formation of homogentisate from p-hydroxyphenylpyruvate. J Am Chem Soc 16:7446-7449 (1970).
18. Goodwin BL, The biochemical, physiological, and clinical significance of p-hydroxyphenylpyruvate oxidase, in Tyrosine catabolism, Oxford University Press, pp 1-94 (1972).
19. Wada GH, Fellman JH, Fujita TS and Roth ES, Purification and properties of avian liver p-hydroxyphenylpyruvate hydroxylase. J Biol Chem 250:6720-6726 (1975).
20. Lindblad B, Lindstedt G, Lindstedt S and Rundgren M, Purification and some properties of human 4-hydroxyphenylpyruvate dioxygenase (I). J Biol Chem 252:5073-5084 (1977).
21. Roche PA, Moorehead TJ and Hamilton GA, Purification and properties of hog liver 4-hydroxyphenylpyruvate dioxygenase. Arch Biochem Biophys 216:62-73 (1982).
22. Endo F, Awata H, Tanoue A, Ishiguro M, Eda Y, Titani K and Matsuda I, Primary structure deduced from complementary DNA sequence and expression in cultured cells of mammalian 4-hydroxyphenylpyruvic acid dioxygenase. J Biol Chem 267:24 235-24 240 (1992).
23. Rüetschi U, Dellsen A, Sahlin P, Stenman G, Rymo L and Lindstedt S, Human 4-hydroxyphenylpyruvate dioxygenase, primary structure and chromosomal localization of the gene. Eur J Biochem 213:1081-1089 (1993).
24. Lindstedt S and Odelhög B, 4-Hydroxyphenylpyruvate dioxygenase from Pseudomonas. Methods Enzymol 142:143-148
25. Lenne C, Matringe M, Roland A, Pallett KE and Douce R, Partial purification and localization of p-hydroxyphenylpyruvate dioxygenase activity from cultured carrot cells, in Advances in photosynthesis research, ed by Mathis P, Vol V, pp 285-288 (1995).
26. Garcia I, Rodgers M, Lenne C, Rolland A, Sailland A and Matringe M, Subcellular localization and purification of a p-hydroxyphenylpyruvate dioxygenase from cultured carrot cells and characterization of the corresponding cDNA. Biochem J 325:761-769 (1997).
27. Pascal RA Jr, Olivier MA and Jack Chen Y-C, Alternate substrates and inhibitors of bacterial 4-hydroxyphenylpyruvate dioxygenase. Biochemistry 24:3158-3165 (1985).
28. Crouch NP, Adlington RM, Baldwin JE, Lee M-H and MacKinnon CH, A mechanistic rationalisation for the substrate specificity of recombinant mammalian 4-hydroxyphenylpyruvate dioxygenase (4-HPPD). Tetrahedron 53:6993-7010 (1997).
29. Niederwieser A, Matasovic A, Tippett P and Danks DM, A new sulfur aminoacid, named hawkinsin, identified in a baby with transient tyrosinemia and her mother. Clin Chim Acta 76:345-356 (1977).
30. Gunsior M, Ravel J, Challis GL and Townsend CA, Engineering p-hydroxyphenylpyruvate dioxygenase to a p-hydroxymandelate synthase and evidence for the proposed benzene oxide intermediate in homogentisate formation. Biochemistry 43:663-674 (2004).
31. Ellis MK, Whitfield AC, Gowans LA, Auton TR, Provan W MacLean, Lock EA, Lee DL and Smith LL, Characterization of the interaction of 2-[2-nitro-4- (trifluoromethyl)benzoyl]-4,4,6,6,-tetramethyl-cyclohexane-1,3,5-trione with rat hepatic 4-hydroxyphenylpyruvate dioxygenase. Chem Res Toxicol 9:24-27 (1996).
32. Viviani F, Little JP and Pallett KE, The mode of action of isoxaflutole II. Characterization of the inhibition of the carrot 4-hydroxyphenylpyruvate dioxygenase by the diketonitrile derivative of isoxaflutole. Pestic Biochem Physiol 62:125-134 (1998).
33. Garcia I, Job D and Matringe M, Inhibition of p-hydroxyphenylpyruvate dioxygenase by the diketonitrile of isoxaflutole: a case of half-site reactivity. Biochemistry 39:7501-7507 (2000).
34. Mitchell G, Bartlett DW, Fraser TEM, Hawkes TR, Holt DC, Townson JK and Wichert RA, Mesotrione: a new selective herbicide for use in maize. Pest Manag Sci 57:120 -128 (2001).
35. Serre L, Sailland A, Sy D, Boudec P, Rolland A, Pebay-Peyroula E and Cohen-Addad C, Crystal structure of Pseudomonas fluorescens 4- hydroxyphenylpyruvate dioxygenase: an enzyme involved in the tyrosine degradation pathway. Structure 7:977-988 (1999).
36. Brownlee JM, Johnson-Winters K, Harrison DHT and Moran GR, Structure of the ferrous form of 4-hydroxyphenylpyruvate dioxygenase from Streptomyces avermitilis in complex with the therapeutic herbicide, NTBC. Biochemistry 43:6370-6377 (2004).
37. Yang C, Pflugrath JW, Camper DL, Foster ML, Pernich D and Walsh TA, Structural basis for herbicidal inhibitor selectivity revealed by comparison of crystal structures of plant and mammalian 4-hydroxyphenylpyruvate dioxygenase. Biochemistry 43:10 414-10 423 (2004).
38. Jung E, Zamir LO and Jensen RA, Chloroplasts of higher plants synthesize L-phenylalanine via L-arogenate. Proc Natl Acad Sci USA 83:7231-7235 (1986).
39. Gaines CG, Gyng GS, Whitaker RJ and Jensen RA. L-Tyrosine regulation and biosynthesis via arogenate dehydrogenase in suspension-cultured cells of Nicotiana silvestris. Speg et Comes. Planta 156:233-240 (1982).
40. Fiedler E, Soil J and Schultz G, The formation of homogentisate in the biosynthesis of tocopherol and plastoquinone in spinach chloroplasts. Planta 155:511-515 (1982).
41. Norris SR, Xiaohua S and DellaPenna D, Complementation of the arabidopsis pdsl mutation with the gene encoding p-hydroxyphenylpyruvate dioxygenase. Plant Physiol 117:1317-1323 (1998).
42. Luscombe BM, Pallett KE, Loubiere P, Millet JC, Melgarejo J and Vrabel TE, RPA 201772: a novel herbicide for broad leaf and grass weed control in maize and sugar cane. in Proc Brighton Crop Prot Conf-Weeds, BCPC, Farnham, Surrey, UK, pp 35-42 (1995).
43. Beraud M, Claument J and Montury A, ICIA0051, A new herbicide for the control of annual weeds in maize, in Proc Brighton Crop Prot Conf-Weeds, BCPC, Farnham, Surrey, UK, pp 51-56 (1993).
44. Yamaoka K, Nakagawa M and Ishida M, Hydrolysis of the rice herbicide pyrazolate in aqueous solutions. Nihon Noyaku Gakkaishi (J Pestic Sci) 12:209-212 (1987).
45. Sailland A, Rolland A, Pallett KE and Matringe M, Gène de l'hydroxy-phényl pyruvate dioxygénase et obtention de plantes contenant ce gène résistantes aux herbicides, Patent Appl WO 9 638 567 (1996).
46. Garcia I, Rodgers M, Pepin R, Hsieh T-F and Matringe M, Characterization and subcellular compartmentation of recombinant 4-hydroxyphenylpyruvate dioxygenase from Arabidopsis in transgenic tobacco. Plant Physiol 119:1507-1516 (1999).
47. Tsegaye Y, Shintani DK and DellaPenna D, Overexpression of the enzyme p-hydroxyphenylpyruvate dioxygenase in Arabidopsis and its relation to tocopherol biosynthesis. Plant Physiol Biochem 40:913-920 (2002).
48. Falk J, Andersen G, Kernebeck B and Krupinska K, Constitutive overexpression of barley 4-hydroxyphenylpyruvate dioxygenase in tobacco results in elevation of the Vitamin E content in seeds but not in leaves. FEBS Lett 540:35-40 (2003).
49. Zink O, Paget E, Rolland A, Sailland A and Freyssinet G, Herbicide tolerant plants through by-passing metabolic pathway, Patent Appl WO 02/36 787 (2002).
50. Rippert P and Matringe M, Kinetic characterization of the two isoforms of arogenate dehydrogenase from Arabidopsis thaliana. Eur J Biochem 269:4753-4761 (2002).
51. Siehl DL, The biosynthesis of tryptophan, tyrosine and phenylalanine from chorismate, in Plant amino acids: biochemistry and biotechnology, ed by Singh BK, Dekker, New York, pp 171-204 (1999).
52. Lingens F, Goebel W and Uesseler H, Regulation der Biosynthese der aromatischen Aminosäuren in Saccharomyces cerevisiae. Eur J Biochem 1:363-374 (1967).
53. Hermann KM and Weaver LM, The shikimate pathway. Annu Rev Plant Physiol Plant Mol Biol 50:473-503 (1999).
54. Rippert P, Simemi C, Manuel D and Matringe M, Engineering plant shikimate pathway for production of tocotrienol and improving herbicide resistance. Plant Physiol 134:92-100 (2004).
55. Brigelius-Flohé R, Kelly FJ, Salonen JT, Neuzil J, Zingg J-M and Azzi A, The European perspective on vitamin E: current knowledge and future research. Am J Clin 76:703-716 (2002).
56. Munne-Bosch S and Alegre L, The function of tocopherols and tocotrienols in plants. Crit Rev Plant Sci 21:31-57 (2002).
57. Seo E-K, Kim N-C, Wani MC, Wall ME, Navarro HA, Burgess JP, Kawanishi K, Kardono LBS, Riswan S, Rose WC, Fairchild CR, Farnsworth NR and Kinghorn AD, Cytotoxic prenylated xanthones and the unusual compounds anthraquinobenzophenones from Cratoxylum sumatranum. J Nat Prod 65:299-305 (2002).
58. Kamal-Eldin A and Appelqvist LA, The chemistry and antioxidant properties of tocopherols and tocotrienols. Lipids 31:671-701 (1996).
59. Kamat JP, Sarma HD, Devasegayan TP, Nesaretnam K and Basiron Y, Tocotrienols from palm oil as effective inhibitor of protein oxidation and lipid peroxidation in rat liver microsomes. Mol Cell Biochem 170:131-137 (1997).
60. Qureshi AA, Salser WA and Parmar R, Emerson EE Novel tocotrienols of rice bran inhibit atherosclerotic lesions in C57BL/6 apoE-deficient mice. J Nutr 131:2606-2618 (2001).
61. Guthrie N, Gapor A, Chambers AF and Carroll KK, Inhibition of estrogen receptor-negative MDA-MB-435 and positive MCF-7 human breast cancer cells by palm oil tocotrienols and tamoxifen, alone and in combination. J Nutr 127:544S-548S (1997).