Glucosinolate metabolism and its control

Trends in Plant Science

Volumn 11, Issue 2, 2006, Pages 89-100

  Grubb, C Douglas ^a,b   Abel, Steffen ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARABIDOPSIS PROTEIN; ATR1 PROTEIN, ARABIDOPSIS; CPC PROTEIN, ARABIDOPSIS; GLUCOSINOLATE; INDOLEACETIC ACID DERIVATIVE; MYB PROTEIN, PLANT; PROTEIN C MYB; VEGETABLE PROTEIN;

ARABIDOPSIS; BIOSYNTHESIS; METABOLISM; PLANT; REVIEW; SIGNAL TRANSDUCTION;

ARABIDOPSIS; ARABIDOPSIS PROTEINS; GLUCOSINOLATES; INDOLEACETIC ACIDS; PLANT PROTEINS; PLANTS; PROTO-ONCOGENE PROTEINS C-MYB; SIGNAL TRANSDUCTION;

ARABIDOPSIS; ARABIDOPSIS THALIANA;

EID: 32544436982     PISSN: 13601385     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tplants.2005.12.006     Document Type: Review

References (107)

1. A. Bussy Sur la formation de l'huile essentielle de moutarde J. Pharmacol. 27 1840 464 471
2. D.J. Kliebenstein The glucosinolate-myrosinase system in an ecological and evolutionary context Curr. Opin. Plant Biol. 8 2005 264 271
3. A.W. Woodward, and B. Bartel Auxin: regulation, action, and interaction Ann. Bot. (Lond.) 95 2005 707 735
4. R. Mithen The nutritional significance, biosynthesis and bioavailability of glucosinolates in human foods J. Sci. Food Agric. 80 2000 967 984
5. P. Talalay, and J.W. Fahey Phytochemicals from cruciferous plants protect against cancer by modulating carcinogen metabolism J. Nutr. 131 2001 3027S 3033S
6. Y.S. Keum Chemoprevention by isothiocyanates and their underlying molecular signaling mechanisms Mutat. Res. 555 2004 191 202
7. J.W. Fahey The chemical diversity and distribution of glucosinolates and isothiocyanates among plants Phytochemistry 56 2001 5 51
8. U. Wittstock, and B.A. Halkier Glucosinolate research in the Arabidopsis era Trends Plant Sci. 7 2002 263 270
9. P.J. Kelly Sub-cellular immunolocalization of the glucosinolate sinigrin in seedlings of Brassica juncea Planta 206 1998 370 377
10. E. Andreasson Different myrosinase and idioblast distribution in Arabidopsis and Brassica napus Plant Physiol. 127 2001 1750 1763
11. H. Husebye Guard cell- and phloem idioblast-specific expression of thioglucoside glucohydrolase 1 (myrosinase) in Arabidopsis Plant Physiol. 128 2002 1180 1188
12. B. Lüthy, and P. Matile The mustard oil bomb: rectified analysis of the subcellular organization of the myrosinase system Biochem. Physiol. Pflanz. 179 1984 5 12
13. A. Ratzka Disarming the mustard oil bomb Proc. Natl. Acad. Sci. U. S. A. 99 2002 11223 11228
14. G. Brader Jasmonate-dependent induction of indole glucosinolates in Arabidopsis by culture filtrates of the nonspecific pathogen Erwinia carotovora Plant Physiol. 126 2001 849 860
15. K.F. Tierens Study of the role of antimicrobial glucosinolate-derived isothiocyanates in resistance of Arabidopsis to microbial pathogens Plant Physiol. 125 2001 1688 1699
16. V. Lambrix The Arabidopsis epithiospecifier protein promotes the hydrolysis of glucosinolates to nitriles and influences Trichoplusia ni herbivory Plant Cell 13 2001 2793 2807
17. D.J. Kliebenstein Comparative analysis of quantitative trait loci controlling glucosinolates, myrosinase and insect resistance in Arabidopsis thaliana Genetics 161 2002 325 332
18. A.A. Agrawal, and N.S. Kurashige A role for isothiocyanates in plant resistance against the specialist herbivore Pieris rapae J. Chem. Ecol. 29 2003 1403 1415
19. U. Wittstock Successful herbivore attack due to metabolic diversion of a plant chemical defense Proc. Natl. Acad. Sci. U. S. A. 101 2004 4859 4864
20. M.D. Mikkelsen Biosynthesis and metabolic engineering of glucosinolates Amino Acids 22 2002 279 295
21. E.W. Underhill Glucosinolates E.A. Bell B.V. Charlwood Encyclopedia of Plant Physiology 1980 Springer 493 511
22. Poulton, J.E. and Møller, B.L. (1993) Glucosinolates. In Methods in Plant Biochemistry (Vol 9) (Lea, P.J., ed.), pp. 209-237, Academic Press
23. E. Glawischnig Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis Proc. Natl. Acad. Sci. U. S. A. 101 2004 8245 8250
24. B.G. Hansen, and B.A. Halkier New insight into the biosynthesis and regulation of indole compounds in Arabidopsis thaliana Planta 221 2005 603 606
25. B.L. Petersen Characterization of transgenic Arabidopsis thaliana with metabolically engineered high levels of p-hydroxybenzylglucosinolate Planta 212 2001 612 618
26. C.H. Hansen CYP83B1 is the oxime-metabolizing enzyme in the glucosinolate pathway in Arabidopsis J. Biol. Chem. 276 2001 24790 24796
27. 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
28. S. Bak CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis Plant Cell 13 2001 101 111
29. M.D. Mikkelsen 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
30. P. Naur CYP83A1 and CYP83B1, two nonredundant cytochrome P450 enzymes metabolizing oximes in the biosynthesis of glucosinolates in Arabidopsis Plant Physiol. 133 2003 63 72
31. M.R. Hemm The Arabidopsis ref2 mutant is defective in the gene encoding CYP83A1 and shows both phenylpropanoid and glucosinolate phenotypes Plant Cell 15 2003 179 194
32. W. Walter, and E. Schaumann The chemistry of thiohydroxamic acids Synthesis 1971 1971 111 130
33. D. Bowles Glycosyltransferases: managers of small molecules Curr. Opin. Plant Biol. 8 2005 254 263
34. E.F. Marillia Molecular cloning of a Brassica napus thiohydroximate S-glucosyltransferase gene and its expression in Escherichia coli Physiol. Plant. 113 2001 176 184
35. C.D. Grubb Arabidopsis glucosyltransferase UGT74B1 functions in glucosinolate biosynthesis and auxin homeostasis Plant J. 40 2004 893 908
36. C.M. Gachon Transcriptional co-regulation of secondary metabolism enzymes in Arabidopsis: functional and evolutionary implications Plant Mol. Biol. 58 2005 229 245
37. M. Piotrowski Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure J. Biol. Chem. 279 2004 50717 50725
38. G. Graser The biosynthesis of benzoic acid glucosinolate esters in Arabidopsis thaliana Phytochemistry 57 2001 23 32
39. G. Graser The methionine chain elongation pathway in the biosynthesis of glucosinolates in Eruca sativa (Brassicaceae) Arch. Biochem. Biophys. 378 2000 411 419
40. S. Textor 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
41. K.L. Falk Glucosinolate biosynthesis: demonstration and characterization of the condensing enzyme of the chain elongation cycle in Eruca sativa Phytochemistry 65 2004 1073 1084
42. B. Field Glucosinolate and amino acid biosynthesis in Arabidopsis Plant Physiol. 135 2004 828 839
43. B. Reintanz Bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates Plant Cell 13 2001 351 367
44. S. Chen CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis Plant J. 33 2003 923 937
45. J. Kroymann Evolutionary dynamics of an Arabidopsis insect resistance quantitative trait locus Proc. Natl. Acad. Sci. U. S. A. 100 Suppl. 2 2003 14587 14592
46. J. Kroymann A gene controlling variation in Arabidopsis glucosinolate composition is part of the methionine chain elongation pathway Plant Physiol. 127 2001 1077 1088
47. A.J.P. Brudenell The phloem mobility of glucosinolates J. Exp. Bot. 50 1999 745 756
48. D.J. Kliebenstein Genetic control of natural variation in Arabidopsis glucosinolate accumulation Plant Physiol. 126 2001 811 825
49. D.J. Kliebenstein Gene duplication in the diversification of secondary metabolism: tandem 2-oxoglutarate-dependent dioxygenases control glucosinolate biosynthesis in Arabidopsis Plant Cell 13 2001 681 693
50. M. Gao Comparative analysis of a Brassica BAC clone containing several major aliphatic glucosinolate genes with its corresponding Arabidopsis sequence Genome 47 2004 666 679
51. 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
52. D.J. Kliebenstein Genetic architecture of plastic methyl jasmonate responses in Arabidopsis thaliana Genetics 161 2002 1685 1696
53. D.J. Kliebenstein Comparative quantitative trait loci mapping of aliphatic, indolic and benzylic glucosinolate production in Arabidopsis thaliana leaves and seeds Genetics 159 2001 359 370
54. W. Boerjan superroot, a recessive mutation in Arabidopsis, confers auxin overproduction Plant Cell 7 1995 1405 1419
55. J.J. King A mutation altering auxin homeostasis and plant morphology in Arabidopsis Plant Cell 7 1995 2023 2037
56. J.L. Celenza Jr A pathway for lateral root formation in Arabidopsis thaliana Genes Dev. 9 1995 2131 2142
57. A. Lehman HOOKLESS1, an ethylene response gene, is required for differential cell elongation in the Arabidopsis hypocotyl Cell 85 1996 183 194
58. M. Delarue Sur2 mutations of Arabidopsis thaliana define a new locus involved in the control of auxin homeostasis Plant J. 14 1998 603 611
59. I. Barlier The SUR2 gene of Arabidopsis thaliana encodes the cytochrome P450 CYP83B1, a modulator of auxin homeostasis Proc. Natl. Acad. Sci. U. S. A. 97 2000 14819 14824
60. G. Smolen, and J. Bender Arabidopsis cytochrome P450 cyp83B1 mutations activate the tryptophan biosynthetic pathway Genetics 160 2002 323 332
61. U. Hoecker The photomorphogenesis-related mutant red1 is defective in CYP83B1, a red light-induced gene encoding a cytochrome P450 required for normal auxin homeostasis Planta 219 2004 195 200
62. J.D. Cohen Two genetically discrete pathways convert tryptophan to auxin: more redundancy in auxin biosynthesis Trends Plant Sci. 8 2003 197 199
63. M.D. Mikkelsen 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
64. Y. Zhao Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3 Genes Dev. 16 2002 3100 3112
65. K. Ljung Sites and regulation of auxin biosynthesis in Arabidopsis roots Plant Cell 17 2005 1090 1104
66. Y. Zhao A role for flavin monooxygenase-like enzymes in auxin biosynthesis Science 291 2001 306 309
67. K. Ljung Biosynthesis, conjugation, catabolism and homeostasis of indole-3-acetic acid in Arabidopsis thaliana Plant Mol. Biol. 49 2002 249 272
68. R. Tobena-Santamaria FLOOZY of petunia is a flavin mono-oxygenase-like protein required for the specification of leaf and flower architecture Genes Dev. 16 2002 753 763
69. S. Pollmann Occurrence and formation of indole-3-acetamide in Arabidopsis thaliana Planta 216 2002 155 161
70. S. Vorwerk Enzymatic characterization of the recombinant Arabidopsis thaliana nitrilase subfamily encoded by the NIT2/NIT1/NIT3-gene cluster Planta 212 2001 508 516
71. A. Kutz A role for nitrilase 3 in the regulation of root morphology in sulphur-starving Arabidopsis thaliana Plant J. 30 2002 95 106
72. S. Grsic-Rausch Expression and localization of nitrilase during symptom development of the clubroot disease in Arabidopsis Plant Physiol. 122 2000 369 378
73. M. Seo Higher activity of an aldehyde oxidase in the auxin-overproducing superroot1 mutant of Arabidopsis thaliana Plant Physiol. 116 1998 687 693
74. T. Tantikanjana Control of axillary bud initiation and shoot architecture in Arabidopsis through the SUPERSHOOT gene Genes Dev. 15 2001 1577 1588
75. T. Tantikanjana Functional analysis of the tandem-duplicated P450 genes SPS/BUS/CYP79F1 and CYP79F2 in glucosinolate biosynthesis and plant development by Ds transposition-generated double mutants Plant Physiol. 135 2004 840 848
76. M. Fontecave S-adenosylmethionine: nothing goes to waste Trends Biochem. Sci. 29 2004 243 249
77. H. Hesse, and R. Hoefgen Molecular aspects of methionine biosynthesis Trends Plant Sci. 8 2003 259 262
78. P.D. Brown Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana Phytochemistry 62 2003 471 481
79. B.L. Petersen Composition and content of glucosinolates in developing Arabidopsis thaliana Planta 214 2002 562 571
80. O.A. Koroleva Identification of a new glucosinolate-rich cell type in Arabidopsis flower stalk Plant Physiol. 124 2000 599 608
81. J. Bender, and G.R. Fink A Myb homologue, ATR1, activates tryptophan gene expression in Arabidopsis Proc. Natl. Acad. Sci. U. S. A. 95 1998 5655 5660
82. M. Levy Arabidopsis IQD1, a novel calmodulin-binding nuclear protein, stimulates glucosinolate accumulation and plant defense Plant J. 43 2005 79 96
83. S. Chen Long-distance phloem transport of glucosinolates in Arabidopsis Plant Physiol. 127 2001 194 201
84. S. Chen, and B.A. Halkier Characterization of glucosinolate uptake by leaf protoplasts of Brassica napus J. Biol. Chem. 275 2000 22955 22960
85. O.P. Thangstad Microautoradiographic localisation of a glucosinolate precursor to specific cells in Brassica napus L. embryos indicates a separate transport pathway into myrosin cells Planta 213 2001 207 213
86. I. Mewis Major signaling pathways modulate Arabidopsis glucosinolate accumulation and response to both phloem-feeding and chewing insects Plant Physiol. 138 2005 1149 1162
87. M.Y. Hirai Elucidation of gene-to-gene and metabolite-to-gene networks in Arabidopsis by integration of metabolomics and transcriptomics J. Biol. Chem. 280 2005 25590 25595
88. A. Maruyama-Nakashita Transcriptome profiling of sulfur-responsive genes in Arabidopsis reveals global effects of sulfur nutrition on multiple metabolic pathways Plant Physiol. 132 2003 597 605
89. P. Reymond A conserved transcript pattern in response to a specialist and a generalist herbivore Plant Cell 16 2004 3132 3147
90. M.D. Mikkelsen Modulation of CYP79 genes and glucosinolate profiles in Arabidopsis by defense signaling pathways Plant Physiol. 131 2003 298 308
91. D. Cipollini Salicylic acid inhibits jasmonic acid-induced resistance of Arabidopsis thaliana to Spodoptera exigua Mol. Ecol. 13 2004 1643 1653
92. M.B. Traw Negative cross-talk between salicylate- and jasmonate-mediated pathways in the Wassilewskija ecotype of Arabidopsis thaliana Mol. Ecol. 12 2003 1125 1135
93. J.L. Celenza The Arabidopsis ATR1 Myb transcription factor controls indolic glucosinolate homeostasis Plant Physiol. 137 2005 253 262
94. J.H. Kim Characterization of the Arabidopsis TU8 glucosinolate mutation, an allele of TERMINAL FLOWER2 Plant Mol. Biol. 54 2004 671 682
95. R.N. Bennett The tu8 mutation of Arabidopsis thaliana encoding a heterochromatin protein 1 homolog causes defects in the induction of secondary metabolite biosynthesis Plant Biol. 7 2005 348 357
96. S. Wakao, and C. Benning Genome-wide analysis of glucose-6-phosphate dehydrogenases in Arabidopsis Plant J. 41 2005 243 256
97. M. Mizutani, and D. Ohta Two isoforms of NADPH:cytochrome P450 reductase in Arabidopsis thaliana. Gene structure, heterologous expression in insect cells, and differential regulation Plant Physiol. 116 1998 357 367
98. K. Jorgensen Metabolon formation and metabolic channeling in the biosynthesis of plant natural products Curr. Opin. Plant Biol. 8 2005 280 291
99. C. Kristensen Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome Proc. Natl. Acad. Sci. U. S. A. 102 2005 1779 1784
100. L. Rask Myrosinase: gene family evolution and herbivore defense in Brassicaceae Plant Mol. Biol. 42 2000 93 113
101. T. Zabala Mde Characterisation of recombinant epithiospecifier protein and its over-expression in Arabidopsis thaliana Phytochemistry 66 2005 859 867
102. 14C] desulfophenethylglucosinolate in Nasturtium officinale Phytochemistry 44 1997 1251 1255
103. J. Vercammen Monitoring of isothiocyanates emanating from Arabidopsis thaliana upon paraquat spraying J. Chromatogr. A. 912 2001 127 134
104. R. Mithen Development of isothiocyanate-enriched broccoli, and its enhanced ability to induce phase 2 detoxification enzymes in mammalian cells Theor. Appl. Genet. 106 2003 727 734
105. K. Faulkner Selective increase of the potential anticarcinogen 4-methylsulphinylbutyl glucosinolate in broccoli Carcinogenesis 19 1998 605 609
106. W.P. Burmeister High resolution X-ray crystallography shows that ascorbate is a cofactor for myrosinase and substitutes for the function of the catalytic base J. Biol. Chem. 275 2000 39385 39393
107. A. Bourderioux The glucosinolate-myrosinase system. New insights into enzyme-substrate interactions by use of simplified inhibitors Org. Biomol. Chem. 3 2005 1872 1879