Geographic and evolutionary diversification of glucosinolates among near relatives of Arabidopsis thaliana (Brassicaceae)

Phytochemistry

Volumn 66, Issue 11 SPEC. ISS., 2005, Pages 1321-1333

  Windsor, Aaron J ^a   Reichelt, Michael ^a   Figuth, Antje ^a   Svatoš, Aleš ^a   Kroymann, Juergen ^a   Kliebenstein, Daniel J ^a,b   Gershenzon, Jonathan ^a   Mitchell Olds, Thomas ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Arabidopsis lyrata; Brassicaceae; Evolution; Genetic constraint; Glucosinolate; Secondary metabolism

Indexed keywords

ARABIDOPSIS LYRATA; ARABIDOPSIS THALIANA; BRASSICACEAE; BRASSICALES;

EID: 20444370659     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2005.04.016     Document Type: Article

References (60)

1. I.A. Al-Shehbaz, L. Steve, and J. O'Kane Taxononmy and phylogeny of Arabidopsis (Brassicaceae) C.R. Somerville E.M. Meyerowitz The Arabidopsis Book 2002 American Society of Plant Biologists Rockville, MD 1 22
2. S. Bak, and R. Feyereisen The involvement of two p450 enzymes, CYP83B1 and CYP83A1, in auxin homeostasis and glucosinolate biosynthesis Plant Physiol. 127 2001 108 118
3. R.S. Baucom, and R. Mauricio Fitness costs and benefits of novel herbicide tolerance in a noxious weed Proc. Natl. Acad. Sci. USA 101 2004 13386 13390
4. P.D. Brown, J.G. Tokuhisa, M. Reichelt, and J. Gershenzon Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana Phytochemistry 62 2003 471 481
5. A. Castro, A. Aires, E. Rosa, E. Bloem, I. Stulen, and L.J. De Kok Distribution of glucosinolates in Brassica oleracea cultivars Phyton 44 2004 133 143
6. C.S. Charron, and C.E. Sams Glucosinolate content and myrosinase activity in rapid-cycling Brassica oleracea grown in a controlled environment J. Am. Soc. Hortic. Sci. 129 2004 321 330
7. S. Chen, E. Glawischnig, K. Jorgensen, P. Naur, B. Jorgensen, B. Jorgensen, C.-E. Olsen, C.H. Hansen, H. Rasmussen, J.A. Pickett, and B.A. Halkier CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis Plant J. 33 2003 923 937
8. M.E. Daxenbichler, G.F. Spencer, D.G. Carlson, G.B. Rose, A.M. Brinker, and R.G. Powell Glucosinolate composition of seeds from 297 species of wild plants Phytochemistry 30 1991 2623 2638
9. K.J. Doughty, A.J.R. Porter, A.M. Morton, G. Kiddle, C.H. Bock, and R. Wallsgrove Variation in the glucosinolate content of oilseed rape Brassica-Napus L. leaves II. Response to infection by Alternaria-Brassicae Berk. Sacc Ann. Appl. Biol. 118 1991 469 478
10. S. Eriksson, B. Ek, J. Xue, L. Rask, and J. Meijer Identification and characterization of soluble and insoluble myrosinase isoenzymes in different organs of Sinapis alba Physiol. Plantarum 111 2001 353 364
11. J.W. Fahey, A.T. Zalcmann, and P. Talalay The chemical diversity and distribution of glucosinolates and isothiocyanates among plants Phytochemistry 56 2001 5 51
12. B. Field, G. Cardon, M. Traka, J. Botterman, G. Vancanneyt, and R. Mithen Glucosinolate and amino acid biosynthesis in Arabidopsis Plant Physiol. 135 2004 828 839
13. R. Font, M. Del Rio, J.M. Fernandez-Martinez, and A. de Haro-Bailon Use of near-infrared spectroscopy for screening the individual and total glucosinolate contents in Indian mustard seed (Brassica juncea L. Czern. & Coss.) J. Agric. Food Chem. 52 2004 3563 3569
14. M. Gao, G. Li, B. Yang, W.R. McCombie, and C.F. Quiros Comparative analysis of a Brassica BAC clone containing several major aliphatic glucosinolate genes with its corresponding Arabidopsis sequence Genome 47 2004 666 679
15. N. Geshi, E. Andreasson, J. Meijer, L. Rask, and A. Brandt Co-localization of myrosinase- and myrosinase-binding proteins in grains of myrosin cells in cotyledon of Brassica napus seedlings Plant Physiol. Biochem. 36 1998 583 590
16. G. Graser, N.J. Oldham, P.D. Brown, U. Temp, and J. Gershenzon The biosynthesis of benzoic acid glucosinolates esters in Arabidopsis thaliana Phytochemistry 57 2001 23 32
17. C.H. Hansen, U. Wittstock, C.E. Olsen, A.J. Hick, J.A. Pickett, and B.A. Halkier Cytochrome P450 CYP79F1 from Arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates J. Biol. Chem. 14 2001 11078 11085
18. M.R. Hemm, M.O. Ruegger, and C. Chapple The Arabidopsis ref2 mutant is defective in the gene encoding CYP83A1 and shows both phenylpropanoid and glucosinolate phenotypes Plant Cell 15 2003 179 194
19. A.K. Hull, R. Vij, and J.L. Celenza Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis Proc. Natl. Acad. Sci. USA 97 2000 2379 2384
20. H. Husebye, S. Chadchawan, P. Winge, O.P. Thangstad, and A.M. Bones Guard cell- and phloem idioblast-specific expression of thioglucoside glucohydrolase 1 (myrosinase) in Arabidopsis Plant Physiol. 128 2002 1180 1188
21. A. Kjaer Glucosinolates in the cruciferae J.G. Vaughn A.J. MacLeod B.M.G. Jones The Biology and Chemistry of the Cruciferae 1976 Academic London, UK 207 219
22. A. Kjaer, and A. Schuster Glucosinolates in seeds of Neslia-Paniculata Phytochemistry 11 1972 3045 3048
23. D.J. Kliebenstein, J. Kroymann, P. Brown, A. Figuth, D. Pedersen, J. Gershenzon, and T. Mitchell-Olds Genetic control of natural variation in Arabidopsis glucosinolate accumulation Plant Physiol. 126 2001 811 825
24. D.J. Kliebenstein, V.M. Lambrix, M. Reichelt, J. Gershenzon, and T. Mitchell-Olds Gene duplication in the diversification of secondary metabolism: tandem 2-oxoglutarate-dependent dioxygenases control glucosinolate biosynthesis in Arabidopsis Plant Cell 13 2001 681 693
25. M. Koch, B. Haubold, and T. Mitchell-Olds Molecular systematics of the Brassicaceae: evidence from coding plastidic matK and nuclear Chs sequences Am. J. Bot. 88 2001 534 544
26. J. Kroymann, and T. Mitchell-Olds Function and evolution of an Arabidopsis insect resistance QTL I. Tikhonovich B. Lugtenberg N. Provorov Biology of Molecular Plant-Microbe Interactions 2004 APS Press Saint Paul, MN 259 262
27. J. Kroymann, S. Textor, J.G. Tokuhisa, K.L. Falk, S. Bartram, J. Gershenzon, and T. Mitchell-Olds A gene controlling variation in Arabidopsis glucosinolate composition is part of the methionine chain elongation pathway Plant Physiol. 127 2001 1077 1088
28. J. Kroymann, S. Donnerhacke, D. Schnabelrauch, and T. Mitchell-Olds Evolutionary dynamics of an Arabidopsis insect resistance quantitative trait locus Proc. Natl. Acad. Sci. USA 100 2003 14587 14592
29. V. Lambrix, M. Reichelt, T. Mitchell-Olds, D.J. Kliebenstein, and J. Gershenzon The Arabidopsis epithiospecifier protein promotes the hydrolysis of glucosinolates to nitriles and influences Trichoplusia ni herbivory Plant Cell 13 2001 2793 2807
30. G. Li, and C.F. Quiros In planta side-chain glucosinolate modification in Arabidopsis by introduction of dioxygenase Brassica homolog BoGSL-ALK Theor. Appl. Genet. 106 2003 1116 1121
31. S.M. Louda, and J.E. Rodman Concentration of glucosinolates in relation to habitat and insect herbivory for the native crucifer Cardamine-Cordifolia Biochem. Syst. Ecol. 11 1983 199 208
32. C. Marazzi, and E. Staedler Arabidopsis thaliana leaf-surface extracts are detected by the cabbage root fly (Delia radicum) and stimulate oviposition Physiol. Entomol. 29 2004 192 198
33. M.D. Mikkelsen, C.H. Hansen, U. Wittstock, and B.A. Halkier Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid J. Biol. Chem. 275 2000 33712 33717
34. M.D. Mikkelsen, B.L. Petersen, C.E. Olsen, and B.A. Halkier Biosynthesis and metabolic engineering of glucosinolates Amino Acids 22 2002 279 295
35. M.D. Mikkelsen, B.L. Petersen, E. Glawischnig, A.B. Jensen, E. Andreasson, and B.A. Halkier Modulation of CYP79 genes and glucosinolate profiles in Arabidopsis by defense signaling pathways Plant Physiol. 131 2003 298 308
36. M.D. Mikkelsen, P. Naur, and B.A. Halkier Arabidopsis mutants in the C-S lyase of glucosinolate biosynthesis establish a critical role for indole-3-acetaldoxime in auxin homeostasis Plant J. 37 2004 770 777
37. T. Mitchell-Olds, I.A. Al-Shehbaz, M. Koch, and T. Sharbel Crucifer evolution in the post-genomic era R. Henry Diversity and Evolution of Plants - Genotype and Phenotype Variation in Higher Plants 2004 CABI Press Wallingford, UK 119 138
38. C.L. Moyes, and A.F. Raybould The role of spatial scale and intraspecific variation in secondary chemistry in host-plant location by Ceutorhynchus assimilis (Coleoptera: Curculionidae) P. Roy. Soc. Lond. B Biol. 268 2001 1567 1573
39. P. Naur, B.L. Petersen, M.D. Mikkelsen, S. Bak, H. Rasmussen, C.-E. Olsen, and B.A. Halkier CYP83A1 and CYP83B1, two nonredundant cytochrome P450 enzymes metabolizing oximes in the biosynthesis of glucosinolates in Arabidopsis Plant Physiol. 133 2003 63 72
40. B.L. Petersen, E. Andreasson, S. Bak, N. Agerbirk, and B.A. Halkier Characterization of transgenic Arabidopsis thaliana with metabolically engineered high levels of p-hydroxybenzylglucosinolate Planta 212 2001 612 618
41. M. Piotrowski, A. Schemenewitz, A. Lopukhina, A. Muller, T. Janowitz, E.W. Weil, and C. Oecking Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure J. Biol. Chem. 279 2004 50717 50725
42. K.A. Pivnick, B.J. Jarvis, and G.P. Slater Identification of olfactory cues used in host-plant finding by diamondback moth, Plutella xylostella (Lepidoptera: Plutellidae) J. Chem. Ecol. 20 1994 1407 1427
43. C.F. Quiros, F. Grellet, J. Sadowski, T. Suzuki, G. Li, and T. Wroblewski Arabidopsis and Brassica comparative genomics: sequence, structure and gene content in the ABI1-Rps2-Ck1 chromosomal segment and related regions Genetics 157 2001 1321 1330
44. A. Ratzka, H. Vogel, D.J. Kliebenstein, T. Mitchell-Olds, and J. Kroymann Disarming the mustard oil bomb Proc. Natl. Acad. Sci. USA 99 2002 11223 11228
45. A.F. Raybould, and C.L. Moyes The ecological genetics of aliphatic glucosinolates Heredity 87 2001 383 391
46. M. Reichelt, P.D. Brown, B. Schneider, N.J. Oldham, E. Stauber, J. Tokuhisa, D.J. Kliebenstein, Mitchell-Olds, and J. Gershenzon Benzoic acid glucosinolate esters and other glucosinolates from Arabidopsis thaliana Phytochemistry 59 2002 663 671
47. B. Reintanz, M. Lehnen, M. Reichelt, J. Gershenzon, M. Kowalczyk, G. Sandberg, M. Godde, R. Uhl, and K. Palme bus, A bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates Plant Cell 13 2001 351 367
48. J.E. Rodman, K.G. Karol, R.A. Price, and K.J. Sytsma Molecules, morphology, and Dahlgren's expanded order Capparales Syst. Bot. 21 1996 289 307
49. J.E. Rodman, P.S. Soltis, D.E. Soltis, K.J. Sytsma, and K.G. Karol Parallel evolution of glucosinolate biosynthesis inferred from congruent nuclear and plastid gene phylogenies Am. J. Bot. 85 1998 997 1006
50. M.T. Rutter, and R.A. Zufall Pathway length and evolutionary constraint in amino acid biosynthesis J. Mol. Evol. 58 2004 218 224
51. D. Schluter, E.A. Clifford, M. Nemethy, and J.S. McKinnon Parallel evolution and inheritance of quantitative traits Am. Nat. 163 2004 809 822
52. S. Textor, S. Bartram, J. Kroymann, K.L. Falk, A. Hick, J. Pickett, and J. Gershenzon Biosynthesis of methionine-derived glucosinolates in Arabidopsis thaliana: recombinant expression and characterization of methylthioalkylmalate synthase, the condensing enzyme of the chain-elongation cycle Planta 218 2004 1026 1035
53. O.P. Thangstad, B. Gilde, S. Chadchawan, M. Seem, H. Husebye, D. Bradley, and A.M. Bones Cell specific, cross-species expression of myrosinases in Brassica napus, Arabidopsis thaliana and Nicotiana tabacum Plant Mol. Biol. 54 2004 597 611
54. D. Tian, M.B. Traw, J.Q. Chen, M. Kreitman, and J. Bergelson Fitness costs of R-gene-mediated resistance in Arabidopsis thaliana Nature 423 2003 74 77
55. J. Tokuhisa, J.-W. de Kraker, S. Textor, and J. Gershenzon The biochemical and molecular origins of aliphatic glucosinolate diversity in Arabidopsis thaliana J.T. Romeo Secondary Metabolism in Model Systems 2004 Pergamon New York, NY 19 38
56. N.M. van Dam, L. Witjes, and A. Svatos Interactions between aboveground and belowground induction of glucosinolates in two wild Brassica species New Phytol. 161 2004 801 810
57. U. Wittstock, and B.A. Halkier Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. catalyzes the conversion of l-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate J. Biol. Chem. 275 2000 14659 14666
58. Y.-W. Yang, K.-N. Lai, P.-Y. Tai, and W.-H. Li Rates of nucleotide substitution in angiosperm mitochondrial DNA sequences and dates of divergence between Brassica and other angiosperm lineages J. Mol. Evol. 48 1999 597 604
59. H.-S. Yoon, and D.A. Baum Transgenic study of parallelism in plant morphological evolution Proc. Natl. Acad. Sci. USA 101 2004 6524 6529
60. R.A. Zufall, and M.D. Rausher Genetic changes associated with floral adaptation restrict future evolutionary potential Nature 428 2004 847 850