Flufenacet herbicide treatment phenocopies the fiddlehead mutant in Arabidopsis thaliana

Pest Management Science

Volumn 59, Issue 8, 2003, Pages 847-856

  Lechelt Kunze, Christa ^a   Meissner, Ruth C ^a   Drewes, Mark ^a,b   Tietjen, Klaus ^b  

^a BAYER AG   (Germany)

^b BAYER CROPSCIENCE AG   (Germany)

Author keywords

Arabidopsis gene expression profile; Benfuresate; Fiddlehead; Flufenacet; Herbicide; Mode of action; Very long chain fatty acid elongase

Indexed keywords

BENFURESATE; ENZYME; FLUFENACET; HERBICIDE; UNCLASSIFIED DRUG; VERY LONG CHAIN FATTY ACID ELONGASE;

GENE EXPRESSION; HERBICIDE; PHENOTYPE;

ARABIDOPSIS; ARTICLE; DRUG MECHANISM; ENZYME INHIBITION; ENZYME SYNTHESIS; GENE EXPRESSION; NONHUMAN; PHENOTYPE; PHYLOGENY;

ACETAMIDES; AMINO ACID SEQUENCE; ARABIDOPSIS; ARABIDOPSIS PROTEINS; BENZOFURANS; GENE EXPRESSION PROFILING; GENE EXPRESSION REGULATION, PLANT; HERBICIDES; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; OLIGONUCLEOTIDE ARRAY SEQUENCE ANALYSIS; PHENOTYPE; PHYLOGENY; SULFONIC ACIDS; THIADIAZOLES;

ARABIDOPSIS; ARABIDOPSIS THALIANA; LILIOPSIDA;

EID: 0042170331     PISSN: 1526498X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ps.714     Document Type: Article

References (71)

1. Berg D, Tietjen K, Wollweber D and Hain R, From genes to targets: impact of functional genomics on herbicide discovery, in Proc Brighton Crop Protect Conf - Weeds, BCPC, Farnham, Surrey, UK, pp 491-500 (1999).
2. Herbicide Resistance Action Committee, http://www.plantprotection.org/hrac/moa2001.htm.
3. Fedtke C, Physiological activity spectra of existing graminicides and the new herbicide 2-(2-benzothiazolyloxy)-N-methyl-N-phenylacetamide (mefenacet). Weed Res 27:221-228 (1987).
4. Fuerst EP, Understanding the mode of action of the chloroacetamide and thiocarbamate herbicides. Weed Tech 1:270-277 (1987).
5. Böger P, Matthes B and Schmalfuß J, Towards the primary target of chloroacetamides - new findings pave the way. Pest Manag Sci 56:497-508 (2000).
6. Böger P and Matthes B, Inhibitors of biosynthesis of very-long-chain fatty acids, in Herbicide classes in development, ed by Böger P, Wakabayashi K and Hirai K, Springer Verlag, Berlin, Heidelberg, pp 115-137 (2002).
7. Bolton P and Harwood JL, Effect of thiocarbamate herbicides on fatty acid synthesis by potato. Phytochemistry 15:1507-1509 (1976).
8. Prakash TR and Swamy PM, Effect of benthiocarb on epicuticular wax and silica content in rice and barnyard grass. Proc Indian Acad Sci, Plant Sci 97:457-460 (1987).
9. Gronwald JW, Lipid biosynthesis inhibitors. Weed Sci 39:435-445 (1991).
10. Abulnaja KO, Tighe CR and Harwood JL, Inhibition of fatty acid elongation provides a basis for the action of the herbicide, ethofumesate, on surface wax formation. Phytochemistry 31:1155-1159 (1992).
11. Barrett PB and Harwood JL, Effects of pebulate and pebulate sulfoxide on very long chain fatty acid biosynthesis. Phytochemistry 48:441-446 (1998).
12. Kolattukudy PE and Brown L, Inhibition of cuticular lipid biosynthesis in Pisum sativum by thiocarbamates. Plant Physiol 53:903-906 (1974).
13. Lolle SJ, Cheung AY and Sussex IM, Fiddlehead: an Arabidopsis mutant constitutively expressing an organ fusion program that involves interactions between epidermal cells. Dev Biol 152:383-392 (1992).
14. Yephremov A, Wismann E, Huijser P, Huijser C, Wellesen K and Saedler H, Characterization of the FIDDLEHEAD Gene of Arabidopsis reveals a link between adhesion response and cell differentiation in the epidermis. Plant Cell 11:2187-2201 (1999).
15. Pruitt RE, Vielle-Calzada J-P, Ploense SE, Grossniklaus U and Lolle SJ, FIDDLEHEAD, a gene required to suppress epidermal cell interactions in Arabidopsis, encodes a putative lipid biosynthetic enzyme. Proc Natl Acad Sci USA 97:1311-1316 (2000).
16. Zhu T, Budworth P, Han B, Brown D, Chang H-S, Zou G and Wang X, Toward elucidating the global gene expression patterns of developing Arabidopsis: parallel analysis of 8 300 genes by a high-density oligonucleotide probe array. Plant Physiol Biochem (Paris) 39:221-242 (2001).
17. Altschul SF, Gish W, Miller W, Myers EW and Lipman DJ, Basic local alignment search tool. J Mol Biol 215:403-410 (http://www.ncbi.nlm.nih.gov/BLAST/) (1990).
18. Corpet F, Multiple sequence alignment with hierarchical clustering. Nucl Acid Res 16:10 881-10 890 (http://prodes.toulouse.inra.fr/multalin/multalin.html) (1988).
19. Lu, see http://bioinfo1.mbfys.lu.se/TOP/maps.html.
20. Wellesen K, Durst F, Pinot F, Benveniste I, Nettesheim K, Wisman E, Steiner-Lange S, Saedler H and Yephremov A, Functional analysis of the LACERATA gene of Arabidopsis provides evidence for different roles of fatty acid ω-hydroxylation in development. Proc Natl Acad Sci USA 98:9694-9699 (2001).
21. Hock B, Fedtke C and Schmidt RR, in: Herbizide. Entwicklung, Anwendung, Wirkungen, Nebenwirkungen, Thieme, Stuttgart (Germany), p 234 (1995) [in German].
22. Hess FD, Holmsen JD and Fedtke C, The influence of the herbicide mefenacet on cell division and cell enlargement in plants. Weed Res 30:21-27 (1990).
23. Anon (and Fedtke C), How do crop protection products work? Action of mefenacet, a grass herbicide, in rice cultivation. Courier Agrochem (Bayer AG, Leverkusen) 14-17 (1995).
24. Bieseler B, Fedtke C, Neuefeind T, Etzel W, Prade L and Reinemer P, Maize selectivity of FOE 5043. Degradation of active ingredient by glutathione-S-transferases. Pflanzenschutz-Nachrichten Bayer (Ger Ed) 50:117-142 (1997).
25. James DW Jr, Lim E, Keller J and Dooner HK, FAE1 genes encoding plant enzymes for fatty acid elongation and their use in altering patterns of plant fatty acid metabolism, PCT Internat Appl WO 9 613 582, 47 pp (1996).
26. Millar AA and Kunst L, Very-long-chain fatty acid biosynthesis is controlled through the expression and specificity of the condensing enzyme. Plant J 12:121-131 (1997).
27. Millar AA, Wrischer M and Kunst L, Accumulation of very-long-chain fatty acids in membrane glycerolipids is associated with dramatic alterations in plant morphology. Plant Cell 10:1889-1902 (1998).
28. Jaworski JG, Post-Beittenmiller MA and Todd J, Fatty acid elongases of Arabidopsis involved in the synthesis of very long chain fatty acids and the genes encoding them, PCT Internat Appl WO 9 854 954, 76 pp (1998).
29. Metz JG, Lardizabal KD and Lassner MW, Nucleic acid sequences encoding a plant cytoplasmic protein involved in fatty acyl-CoA metabolism and production of very-long-chain fatty acids and wax esters, PCT Internat Appl WO 9 515 387, 147 pp (1995).
30. Kunst L and Millar AA, Nucleic acids encoding a Arabidopsis thaliana enzyme involved in very long chain fatty acid synthesis, PCT Internat Appl WO 9 846 766, 58 pp (1998).
31. Millar AA, Clemens S, Zachgo S, Giblin EM, Taylor DC and Kunst L, CUT1, an Arabidopsis gene required for cuticular wax biosynthesis and pollen fertility, encodes a very-long-chain fatty acid condensing enzyme. Plant Cell 11:825-838 (1999).
32. Todd J, Post-Beittenmiller D and Jaworski JG, KCS1 encodes a fatty acid elongase 3-ketoacyl-CoA synthase affecting wax biosynthesis in Arabidopsis thaliana. Plant J 17:119-130 (1999).
33. Kunst L and Clemens S, Arabidopsis long chain β-ketoacyl-CoA synthase2 for modification of fatty acid composition, PCT Internat Appl WO 01 07 586, 32 pp (2001).
34. 2 perception to stomatal development. Nature (London) 408:713-716 (2000).
35. Ferrer J-L, Jez JM, Bowman ME, Noel RA and Dixon JP, Structure of chalcone synthase and the molecular basis of plant polyketide biosynthesis. Nat Struct Biol 6:775-784 (1999).
36. Huang W, Jia J, Edwards P, Dehesh K, Schneider G and Lindqvist Y, Crystal structure of β-ketoacyl-acyl carrier protein synthase II from E. coli reveals the molecular architecture of condensing enzymes. EMBO J 17:1183-1191 (1998).
37. Moche M, Schneider G, Edwards P, Dehesh K and Lindqvist Y, Structure of the complex between the antibiotic cerulenin and its target, β-ketoacyl-acyl carrier protein synthase. J Biol Chem 274:6031-6034 (1999).
38. Olsen JG, Kadziola A, Von Wettstein-Knowles P, Siggaard-Andersen M, Lindqvist Y and Larsen S, The X-ray crystal structure of β-ketoacyl (acyl carrier protein) synthase I. FEBS Lett 460:46-52 (1999).
39. Qiu X, Janson CA, Konstantinidis AK, Nwagwu S, Silverman C, Smith WW, Khandekar S, Lonsdale J and Abdel-Meguid SS, Crystal structure of β-ketoacyl-acyl carrier protein synthase III. A key condensing enzyme in bacterial fatty acid biosynthesis. J Biol Chem 274:36 465-36 471 (1999).
40. Davies C, Heath RJ, White SW and Rock CO, The 1.8.ANG. crystal structure and active-site architecture of β-ketoacylacyl carrier protein synthase III (FabH) from Escherichia coli. Structure (London) 8:185-195 (2000).
41. Von Wettstein-Knowles P, Olsen JG, McGuire KA and Larsen S, Molecular aspects of β-ketoacyl synthase (KAS) catalysis. Biochem Soc Trans 28:601-607 (2000).
42. Olsen JG, Kadziola A, Von Wettstein-Knowles P, Siggaard-Andersen M and Larsen S, Structures of β-ketoacyl-acyl carrier protein synthase I complexed with fatty acids elucidate its catalytic machinery. Structure 9:233-243 (2001).
43. Ghanevati M and Jaworski JG, Active-site residues of a plant membrane-bound fatty acid elongase β-ketoacyl-CoA synthase, FAE1 KCS. Biochim Biophys Acta 1530:77-85 (2001).
44. Ghanevati M and Jaworski JG, Engineering and mechanistic studies of the Arabidopsis FAE1 β-ketoacyl-CoA synthase, FAE1 KCS. Eur J Biochem 269:3531-3539 (2002).
45. Millar AA, Smith MA and Kunst L, All fatty acids are not equal: discrimination in plant membrane lipids. Trends Plant Sci 5:95-101 (2000).
46. Lolle SJ, Berlyn GP, Engstrom EM, Krolikowski KA, Reiter WD and Pruitt RE, Developmental regulation of cell interactions in the Arabidopsis fiddlehead-1 mutant: a role for the epidermal cell wall and cuticle. Dev Biol 189:311-321 (1997).
47. Van der Lee FM, Sijmons PC, Hetherington AM, Holroyd GH and Gray JE, Fatty acid elongase gene expression in guard cells regulates stomatal number, PCT Internat Appl WO 9 954 471, 45 pp (1999).
48. Moon H, Smith MA and Kunst L, A condensing enzyme from the seeds of Lesquerella fendleri that specifically elongates hydroxy fatty acids. Plant Physiol 127:1635-1643 (2001).
49. Rossak M, Smith M and Kunst L, Expression of the FAE1 gene and FAE1 promoter activity in developing seeds of Arabidopsis thaliana. Plant Mol Biol 46:717-725 (2001).
50. Cheong YH, Chang HS, Gupta R, Wang X, Zhu T and Luan S, Transcriptional profiling reveals novel interactions between wounding, pathogen, abiotic stress, and hormonal responses in Arabidopsis. Plant Physiol 129:661-677 (2002). Supplementary information is from the online publication http://www.plantphysiol.org/cgi/content/full/129/2/661/DC1.
51. Nishitani K, The role of endoxyloglucan transferase in the organization of plant cell walls. Internat Rev Cytol 173:157-206 (1997).
52. Wadsworth GJ, The plant aspartate aminotransferase gene family. Physiol Plantarum 100:998-1006 (1997).
53. Aarts MG, Hodge R, Kalantidis K, Florack D, Wilson ZA, Mulligan BJ, Stiekema WJ, Scott R and Pereira A, The Arabidopsis MALE STERILITY 2 protein shares similarity with reductases in elongation/condensation complexes. Plant J 12:615-623 (1997).
54. Metz JG, Pollard MR, Anderson L, Hayes TR and Lassner MW, Purification of a jojoba embryo fatty acyl-coenzyme reductase and expression of its cDNA in high erucic acid rapeseed. Plant Physiol 122:635-644 (2000).
55. Xu X, Dietrich CR, Delledonne M, Xia Y, Wen T-J, Robertson DS, Nikolau BJ and Schnable PS, Sequence analysis of the cloned glossy8 gene of maize suggests that it may code for a β-ketoacyl reductase required for the biosynthesis of cuticular waxes. Plant Physiol 115:501-510 (1997).
56. Sieber P, Schorderet M, Ryser U, Buchala A, Kolattukudy P, Metraux JP and Nawrath C, Transgenic Arabidopsis plants expressing a fungal cutinase show alterations in the structure and properties of the cuticle and postgenital organ fusions. Plant Cell 12:721-737 (2000).
57. Jablonkai I and Dutka F, Structure, alkylating reactivity and phytotoxicity relationships of chloroacetamides, Proc Brighton Crop Protect Conf - Weeds, BCPC, Farnham, Surrey, UK, pp 455-462 (1989).
58. Price AC, Choi K-H, Heath RJ, Li Z, White SW and Rock CO, Inhibition of β-ketoacyl-acyl carrier protein synthases by thiolactomycin and cerulenin. Structure and mechanism. J Biol Chem 276:6551-6559 (2001).
59. Loftus TM, Frehywot DE, Jaworsky GL, Townsend CA, Ronnett GV, Lane MD and Kuhajda FP, Reduced food intake and body weight in mice treated with fatty acid synthase inhibitors. Science (Washington) 288:2379-2381 (2000).
60. Lechelt-Kunze C, Meissner R and Tietjen K, The gene for the very long chain fatty acid elongase of Arabidopsis thaliana and the identification of herbicides acting on it, Eur Pat Appl EP 1 174 517, 22 pp (2002).
61. Lemieux B, Molecular genetics of epicuticular wax biosynthesis. Trends Plant Sci 1:312-318 (1996).
62. Post-Beittenmiller D, Biochemistry and molecular biology of wax production in plants. Annu Rev Plant Physiol Plant Mol Biol 47:405-430 (1996).
63. David D, Sundarababu S and Gerst JE, Involvement of long chain fatty acid elongation in the trafficking of secretory vesicles in yeast. J Cell Biol 143:1167-1182 (1998).
64. Doss RP, Oliver JE, Proebsting WM, Potter SW, Kuy S, Clement SL, Williamson RT, Carney JR and DeVilbiss ED, Bruchins: insect-derived plant regulators that stimulate neoplasm formation. Proc Natl Acad Sci USA 97:221-228 (2000).
65. Sinha N, The response of epidermal cells to contact. Trends Plant Sci 5:233-234 (2000).
66. Sharma VK and Fletcher JC, Maintenance of shoot and floral meristem cell proliferation and fate. Plant Physiol 129:31-39 (2002).
67. Serna L and Fenoll C, Reinforcing the idea of signalling in the stomatal pathway. Trends Genet 18:597-600 (2002).
68. Toke DA and Mart CE, Isolation and characterization of a gene affecting fatty acid elongation in Saccharomyces cerevisiae. J Biol Chem 271:18413-18422 (1996).
69. Oh CS, Toke DA, Mandala S and Martin CE, ELO2 and ELO3, homologues of the Saccharomyces cerevisiae ELO1 gene, function in fatty acid elongation and are required for sphingolipid formation. J Biol Chem 272:17 376-17 384 (1997).
70. Zank TK, Zähringer U, Lerchl J and Heinz E, Cloning and functional expression of the first plant fatty acid elongase specific for D6-polyunsaturated fatty acids. Biochem Soc Trans 28:654-658 (2000).
71. Domergue F, Casagne C and Lessire R, Acyl-CoA elongases and seeds; the other system for fatty acid synthesis. Ol Corps Gras Lipid 6:101-106 (1999).