Regulation of plant glucosinolate metabolism

Andreasson E, Jørgensen LB, Hoglund AS, Rask L, Meijer J (2001) Different myrosinase and idioblast distribution in Arabidopsis and Brassica napus. Plant Physiol 127:1750–1763

Apel K, Hirt H (2004) Reactive oxygen species: metabolism, oxidative stress and signal transduction. Annu Rev Plant Biol 55:373–399

Armengaud P, Breitling R, Amtmann A (2004) The potassium-dependent transcriptome of Arabidopsis reveals a prominent role of jasmonic acid in nutrient signaling. Plant Physiol 136:2556–2576

Bak S, Feyereisen R (2001) The involvement of two P450 enzymes CYP83B1 and CYP83A1 in auxin homeostasis and glucosinolate biosynthesis. Plant Physiol 127:108–118

Barlier I, Kowalczyk M, Marchant A, Ljung K, Bhalerao M (2000) The SUR2 gene of Arabidopsis thaliana encodes the cytochrome P450 CYP83B1, a modulator of auxin homeostasis. Proc Natl Acad Sci USA 97:14819–14824

Barth C, Jander G (2006) Arabidopsis myrosinases TGG1 and TGG2 have redundant function in glucosinolate breakdown and insect defense. Plant J 46:549–562

Bartlet E, Kiddle G, Williams I, Wallsgrove R (1999) Wound-induced increases in the glucosinolate content of oilseed rape and their effect on subsequent herbivory by a crucifer specialist. Entomol Exp Appl 91:163–167

Bodnaryk (1992) Effects of wounding on the glucosinolates in the cotyledons of oilseed rape and mustard. Phytochem 31:2671–2677

Boerjan W, Cervera MT, Delarue M, Beeckman T, Dewitte W, Bellini C, Caboche M, Van Onckelen H, Van Montagu M, Inze D (1995) Superroot, a recessive mutation in Arabidopsis, confers auxin overproduction. Plant Cell 7:1405–1419

Brader G, Tas E, Palva ET (2001) Jasmonate-dependent induction of indole glucosinolates in Arabidopsis by culture filtrates of the nonspecific pathogen Erwinia carotovora. Plant Physiol 126:849–860

Burow M, Bergner A, Gershenzon J, Wittstock U (2007) Glucosinolate hydrolysis in Lepidium sativum-identification of the thiocyanate-forming protein. Plant Mol Biol 63:49–61

Carter C, Pan S, Zouhar J, Avila EL, Girke T, Raikhel NV (2004) The vegetative vacuole proteome of Arabidopsis thaliana reveals predicted and unexpected proteins. Plant Cell 16:3285–3303

Champoliver L, Merrien A (1996) Effects of water stress applied at different growth stages to Brassica napus L. var. oleifera on yield, yield components and seed quality. Eur J Agr 5:153–160

Celenza JL, Quiel JA, Smolen GA, Merrikh H, Silvestro AR, Normanly J, Bender J (2005) The Arabidopsis ATR1 Myb transcription factor controls indolic glucosinolate homeostasis. Plant Physiol 137:253–262

Chen S, Andreasson E (2001) Update on glucosinolate metabolism and transport. Plant Physiol Biochem 39:743–758

Chen S, Harmon A (2006) Advances in plant proteomics. Proteomics 6:5504–5516

Chen S, Glawischnig E, Jørgensen K, Naur P, Jørgensen B, Olsen CE, Hansen CH, Rasmussen H, Pickett J, Halkier BA (2003a) CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis. Plant J 33:923–937

Chen S, Hofius D, Sonnewald U, Bornke F (2003b) Temporal and spatial control of gene silencing in transgenic plants by inducible expression of double-stranded RNA. Plant J 36:731–740

Desikan R, Clarke A, Hancock JT, Neill SJ (1999) H2O2 activates a MAP kinase-like enzyme in Arabidopsis thaliana suspension cultures. J Exp Bot 50:1863–1866

Desikan R, A-H-Mackerness S, Hancock JT, Neill SJ (2001) Regulation of the Arabidopsis transcriptome by oxidative stress. Plant Physiol 127:159–172

Engelen-Eigles G, Holden G, Cohen JD, Gardner G (2006) The effect of temperature, photoperiod, and light quality on gluconasturtiin concentration in watercress (Nasturtium officinale R. Br.). J Agric Food Chem 54:328–334

Felice AD, Tran DH, Jorstad TS, Rossiter JT, Bones AM (2006) Glucosinolates in Arabidopsis thaliana rosette leaves show oscillatory tendencies throughout a diurnal cycle. In: Abstract of the first international conference on glucosinolate, Jena, Germany, pp 29

Gao M, Li G, Yang B, McCombie WR, Quiros CF (2004) Comparative analysis of a Brassica BAC clone containing several major aliphatic glucosinolate genes with its corresponding Arabidopsis sequence. Genome 47:666–679

Giamoustaris A, Mithen R (1995) The effect of modifying the glucosinolate content of oilseed rape (Brassica napus ssp oleifera) on its interaction with specialist and generalist pests. Ann Appl Biol 126:347–363

Giamoustaris A, Mithen R (1996) Genetics of aliphatic glucosinolates: 4. Side-chain modification in Brassica oleracea. Theor Appl Genet 93:1006–1010

Giamoustaris A, Mithen R (1997) Glucosinolates and disease resistance in oilseed rape (Brassica napus ssp. oleifera). Plant Pathol 46:271–275

Gigolashvili T, Berger B, Mock HP, Muller C, Weisshaar B, Flugge UI (2007) The transcription factor HIG1/MYB51 regulates indolic glucosinolate biosynthesis in Arabidopsis thaliana. Plant J 50:886–901

Glazebrook J, Chen W, Esters B, Chang HS, Nawrath C, Metraux JP, Zhu T, Katagiri F (2003) Topology of the network integrating salicylate and jasmonate signal transduction derived from global expression phenotyping. Plant J 34:217–228

Grubb CD, Abel S (2006) Glucosinolate metabolism and its control. Trends Plant Sci 11:89–100

Grubb CD, Zipp BJ, Muller JL, Masuno MN, Molinski TF, Abel S (2004) Arabidopsis glucosyltransferase UGT74B1 functions in glucosinolate biosynthesis and auxin homeostasis. Plant J 40:893–908

Gygi SP, Rochon Y, Franza BR, Aebersold R (1999) Correlation between protein and mRNA abundance in yeast. Mol Cell Biol 19:1720–1730

Halkier BA, Gershenzon J (2006) Biology and biochemistry of glucosinolates. Ann Rev Plant Biol 57:303–333

Hall C, McCallum D, Prescott A, Mithen R (2001) Biochemical genetics of glucosinolate modification in Arabidopsis and Brassica. Theor Appl Genet 102:369–374

Hansen CH, Wittstock U, Olsen CE, Hick AJ, Pickett JA, Halkier BA (2001) 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 276:11078–11085

Hansen BG, Kliebenstein DJ, Halkier BA (2007) Identification of a flavin-monooxygenase as the S-oxygenating enzyme in aliphatic glucosinolate biosynthesis in Arabidopsis. Plant J 50:902–910

Hemm MR, Ruegger MO, Chapple C (2003) The Arabidopsis ref2 mutant is defective in the gene encoding CYP83A1 and shows both phenylpropanoid and glucosinolate phenotypes. Plant Cell 15:179–194

Hirai MY, Yano M, Goodenowe DB, Kanaya S, Kimura T, Awazuhara M, Arita M, Fujiwara T, Saito K (2004) Integration of transcriptomics and metabolomics for understanding of global responses to nutritional stresses in Arabidopsis thaliana. Proc Natl Acad Sci USA 101:10205–10210

Hirai MY, Sugiyama K, Sawada Y, Tohge T, Obayashi T, Suzuki A, Araki R, Sakurai N, Suzuki H, Aoki K, Goda H, Nishizawa OI, Shibata D, Saito K (2007) Omics-based identification of Arabidopsis Myb transcription factors regulating aliphatic glucosinolate biosynthesis. Proc Natl Acad Sci USA 104:6478–6483

Hopkins RJ, Griffiths DW, Birch ANE, McKinlay RG (1998) Influence of increasing herbivore pressure on modification of glucosinolate content of Swedes (Brassica napus ssp rapifera). J Chem Ecol 24:2003–2019

Hull AK, Vij R, Celenza JL (2000) Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis. Proc Natl Acad Sci USA 97:2379–2384

Husebye H, Chadchawan S, Winge P, Thangstad OP, Bones AM (2002) Guard cell- and phloem idioblast-specific expression of thioglucoside glucohydrolase 1 (myrosinase) in Arabidopsis. Plant Physiol 128:1180–1188

Jones AME, Thomas V, Bennett MH, Mansfield J, Grant M (2006) Modifications to Arabidopsis defence proteome occur prior to significant transcription change in response to inoculation with Pseudomonas syringae. Plant Physiol 142:1603–1620

Keck AS, Finley JW (2004) Cruciferous vegetables: cancer protective mechanisms of glucosinolate hydrolysis products and selenium. Integr Cancer Ther 3:5–12

Keurentjes JJB, Fu J, de Vos CHR, Lommen A, Hall RD, Bino RJ, van der Plas LHW, Jansen RC, Vreugdenhil D, Koornneef M (2006) The genetics of plant metabolism. Nature Genet 38:842–849

Kim SJ, Matsuo T, Watannabe M, Watannabe Y (2002) Effect of nitrogen and sulphur application on the glucosinolate concentration in vegetable turnip rape (Brassica rapa L). Soil Sci Plant Nutr 48:43–49

Kliebenstein DJ, Kroymann J, Brown P, Figuth A, Pedersen D, Gershenzon J, Mitchell-Olds T (2001) Genetic control of natural variation in Arabidopsis glucosinolate accumulation. Plant Physiol 126:811–825

Koroleva OA, Davies A, Deeken R, Thorpe MR, Tomos AD, Hedrich R (2000) Identification of a new glucosinolate-rich cell type in Arabidopsis flower stalk. Plant Physiol 124:599–608

Kroymann J, Textor S, Tokuhisa JG, Falk KL, Bartram S, Gershenzon J, Mitchell-Olds T (2001) A gene controlling variation in Arabidopsis glucosinolate composition is part of the methionine chain elongation pathway. Plant Physiol 127:1077–1088

Kroymann J, Donnerhacke S, Schnabelrauch D, Mitchell-Olds T (2003) Evolutionary dynamics of an Arabidopsis resistance quantitative trait locus. Proc Natl Acad Sci USA 100:14587–14592

Krumbein A, Schonhof I, Ruhlmann J, Widell S (2002) Influence of sulfur and nitrogen supply on flavour and health-affecting compounds in Brassicaceae. Plant Nutr 92:294–295

Kutz A, Müller A, Hennig P, Kaiser WM, Piotrowski M, Weiler EW (2002) A role for nitrilase 3 in the regulation of root morphology in sulphur-starving Arabidopsis thaliana. Plant Cell 30:95–106

Lambrix V, Reichelt M, Mitchell-Olds T, Kliebenstein DJ, Gershenzon J (2001) The Arabidopsis epithiospecifier protein promotes the hydrolysis of glucosinolates to nitriles and influences Trichoplusia ni herbivory. Plant Cell 13:2793–2807

Lee K, Lee J, Kim Y, Bae Y, Kang KY, Lim D (2004) Defining the plant disulfide proteome. Electrophoresis 25:532–541

Levy M, Wang Q, Kaspi R, Parrella MP, Abel S (2005) Arabidopsis IQD1, a novel calmodulin-binding nuclear protein, stimulates glucosinolate accumulation and plant defense. Plant J 43:79–96

Li Y, Kiddle GA, Bennett RN, Wallsgrove RM (1999) Local and systemic changes in glucosinolates in Chinese and European cultivars of oilseed rape (Brassica napus) after inoculation with Sclerotinia sclerotiorum (stem rot). Ann Appl Biol 134:45–58

Li J, Brader G, Kariola T, Palva ET (2006) WRKY70 modulates the selection of signaling pathways in plant defense. Plant J 46:477–491

Ludwig-Muller J, Krishna P, Forreiter C (2000) A glucosinolate mutant of Arabidopsis is thermosensitive and defective in cytosolic Hsp 90 expression after heat stress. Plant Physiol 123:949–958

Maruyama-Nakashita A, Inoue E, Watanabe-Takahashi A, Yamaya T, Takahashi H (2003) Transcriptome profiling of sulfur-responsive genes in Arabidopsis reveals global effects of sulfur nutrition on multiple metabolic pathways. Plant Physiol 132:597–605

Maruyama-Nakashita A, Nakamura Y, Tohge T, Saito K, Takahashi H (2006) Arabidopsis SLIM1 is a central transcriptional regulator of plant sulfur response and metabolism. Plant Cell 18:3235–3251

Mathys W (1977) The role of malate, oxalate and mustard oil glucosides in the evolution of zinc resistance in herbage plants. Physiol Plant 40:130–136

Mayton HS, Oliver C, Vaughn SF, Loria R (1996) Correlation of fungicidal activity of Brassica species with allyl isothiocyanate production in macerated leaf tissue. Phytopathology 86:267–271

Mewis I, Appel HM, Hom A, Raina R, Schultz JC (2005) Major signaling pathways modulate Arabidopsis glucosinolate accumulation and response to both phloem-feeding and chewing insects. Plant Physiol 138:1149–1162

Mikkelsen MD, Hansen CH, Wittstock U, Halkier BA (2000) 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 275:33712–33717

Mikkelsen MD, Petersen BL, Glawischnig E, Jensen AB, Andreasson E, Halkier BA (2003) Modulation of CYP79 genes and glucosinolate profiles in Arabidopsis by defense signaling pathways. Plant Physiol 131:298–308

Mikkelsen MD, Naur P, Halkier BA (2004) Arabidopsis mutants in the C-S lyase of glucosinolate biosynthesis establish a critical role for indole-3-acetaldoxime in auxin homeostasis. Plant J 37:770–777

Nikiforova V, Kopka J, Tolstikov V, Fiehn O, Hopkins L, Hawkesford MJ, Hesse H, Hoefgen R (2005) Systems rebalancing of metabolism in response to sulfur deprivation, as revealed by metabolome analysis of Arabidopsis plants. Plant Physiol 138:304–318

Nafisi M, Goregaoker S, Botanga CJ, Glawischnig E, Olsen CE, Halkier BA, Glazebrook J (2007) Arabidopsis cytochrome P450 monooxygenase 71A13 catalyzes the conversion of indole-3-acetaldoxime in camalexin synthesis. Plant Cell (in press)

Noret N, Meerts P, Vanhaelen M, Santos AD, Escarré J (2007) Do metal-rich plants deter herbivores? A field test of the defence hypothesis. Oecologia 152:92–100

Paget MSB, Buttner MJ (2003) Thiol-based regulatory switches. Annu Rev Genet 37:91–121

Pandey A, Mann M (2000) Proteomics to study genes and genomes. Nature 405:837–846

Petersen BL, Andreasson E, Bak S, Agerbirk N, Halkier BA (2001) Characterization of transgenic Arabidopsis thaliana with metabolically engineered high levels of p-hydroxybenzylglucosinolate. Planta 212:612–618

Petersen BL, Chen S, Hansen CH, Halkier BA (2002) Composition and content of glucosinolates in developing Arabidopsis thaliana. Planta 214:562–571

Piotrowski M, Schemenewitz A, Lopukhina A, Iler AM, Janowitz T, Weiler EW, Oecking C (2004) Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure. J Biol Chem 279:50717–50725

Rask L, Andreasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J (2000) Myrosinase: gene family evolution and herbivore defense in Brassicaceae. Plant Mol Biol 42:93–113

Reintanz B, Lehnen M, Reichelt M, Gershenzon J, Kowalczyk M, Sandberg G, Godde M, Uhl R, Pame K (2001) bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates. Plant Cell 13:351–367

Reymond P, Bodenhausen N, Van Poecke RMP, Krishnamurthy V, Dicke M, Farmer EE (2004) A conserved transcript pattern in response to a specialist and a generalist herbivore. Plant Cell 16:3132–3147

Schenk PM, Kazan K, Wilson I, Anderson JP, Richmond T, Somerville SC, Manners JM (2000) Coordinated plant defense responses in Arabidopsis revealed by microarray analysis. Proc Natl Acad Sci USA 97:11655–11660

Schnug E (1990) Sulphur nutrition and quality of vegetables. Sulfur Agric 14:3–7

Schnug E, Haneklaus S, Murphy D (1993) Impact of sulfur fertilization on fertilizer nitrogen efficiency. Sulfur Agr 17:8–12

Schonhof I, Klaring HP, Krumbein A, Schreiner M (2007a) Interaction between atmospheric CO2 and glucosinolates in broccoli. J Chem Ecol 33:105–114

Schonhof I, Blankenburg D, Muller S, Krumbein A (2007b) Sulfur and nitrogen supply influence growth, product appearance, and glucosinolate concentration of broccoli. J Plant Nutr Soil Sci 170:65–72

Schuhegger R, Nafisi M, Mansourova M, Petersen BL, Olsen CE, Svatos A, Halkier BA, Glawischnig E (2006) CYP71B15 (PAD3) catalyzes the final step in camalexin biosynthesis. Plant Physiol 141:1248–1256

Siemens DH, Mitchell-Olds T (1998) Evolution of pest-induced defenses in Brassica plants: tests of theory. Ecol 79:632–646

Skirycz S, Reichelt M, Burow M, Birkemeyer C, Rolcik J, Kopka J, Zanor MI, Gershenzon J, Strnad M, Szopa J, Mueller-Roeber B, Witt I (2006) DOF transcription factor AtDof1.1 (OBP2) is part of a regulatory network controlling glucosinolate biosynthesis in Arabidopsis. Plant J 47:10–24

Tantikanjana T, Mikkelsen MD, Hussain M, Halkier BA, Sundaresan V (2004) 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 135:840–848

Textor S, de Kraker JW, Hause B, Gershenzon J, Tokuhisa JG (2007) MAM3 catalyzes the formation of all aliphatic glucosinolate chain lengths in Arabidopsis. Plant Physiol 144:60–71

Tierens K, Thomma BPH, Brouwer M, Schmidt J, Kistner K, Porzel A, Mauch-Mani B, Cammue BPA, Broekaert WF (2001) Study of the role of antimicrobial glucosinolate-derived isothiocyanates in resistance of Arabidopsis to microbial pathogens. Plant Physiol 125:1688–1699

Tolra RP, Poschenrieder C, Alonso R, Barcelo D, Barcelo J (2001) Influence of zinc hyperaccumulation on glucosinolates in Thlaspi caerulescens. New Phytol 151:621–626

Ueda H, Nishiyama C, Shimada T, Koumoto Y, Hayahi Y, Kondo M, Takahashi T, Ohtomo I, Nishimura M, Hara-Nishimura I (2006) AtVAM3 is required for normal specification of idioblasts, myrosin cells. Plant Cell Physiol 47:164–175

Velasco P, Cartea ME, Gonzalez C, Vilar M, Ordas A (2007) Factors affecting the glucosinolate content of kale (Brassica oleracea acephala group). J Agric Food Chem 55:955–962

Wittstock U, Halkier BA (2000) Cytochrome P450 CYP79A2 from Arabidopsis thaliana catalyzes the conversion of l-phenylalanine to phenylacetaldoxime in the biosynthesis of the benzylglucosinolate. J Biol Chem 275:14659–14666

Zhang Z, Ober JA, Kliebenstein DJ (2006) The gene controlling the quantitative trait locus epithiospecifier modifier 1 alters glucosinolate hydrolysis and insect resistance in Arabidopsis. Plant Cell 18:1524–1536

Zhao F, Evans E, Bilsborrow PE, Syers JK (1994) Influence of nitrogen and sulphur on the glucosinolate profile of rapeseed (Brassica napus L). J Sci Food Agric 64:295–304

Zhao Y, Hull AK, Gupta N, Goss KA, Alonso J, Ecker JR, Normanly J, Chory J, Celenza JL (2002) Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3. Genes Dev 16:3100–3112