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N Use By Plants
Nitrate Assimilation
Ammonia Assimilation
Glu, Gln, Asn, Gly, Ser
Aminotransferases
Asp, Ala, GABA
Val, Leu, Ileu, Thr, Lys
Pro, Arg, Orn
Polyamines
Non-protein AAs
Alkaloids
Sulfate Assimilation
Cys, Met, AdoMet, ACC
His, Phe, Tyr, Tryp
Secondary Products
Onium Compounds
Enzymes
Methods
Simulation
References
HORT640 - Metabolic Plant Physiology

References, myrosinase

Alvarez S, He Y, Chen S. Comparative investigations of the glucosinolate-myrosinase system in Arabidopsis suspension cells and hypocotyls. Plant Cell Physiol. 49: 324-333 (2008).

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

Andreasson E, Taipalensuu J, Rask L, Meijer J. Age-dependent wound induction of a myrosinase-associated protein from oilseed rape (Brassica napus). Plant Mol. Biol. 41: 171-180 (1999).

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

Bennett R, Mellon F, Botting N, Eagles J, Rosa E, Williamson G. Identification of the major glucosinolate (4-mercaptobutyl glucosinolate) in leaves of Eruca sativa L. (salad rocket). Phytochemistry 61: 25 (2002).

Bennett RN, Wenke T, Freudenberg B, Mellon FA, Ludwig-Muller J. The tu8 mutation of Arabidopsis thaliana encoding a heterochromatin protein 1 homolog causes defects in the induction of secondary metabolite biosynthesis. Plant Biol. (Stuttg.) 7: 348-357 (2005).

Bones AM, Rossiter JT. The enzymic and chemically induced decomposition of glucosinolates. Phytochemistry 67: 1053-1067 (2006).

Botti MG, Taylor MG, Botting NP. Studies on the mechanism of myrosinase. Investigation of the effect of glycosyl acceptors on enzyme activity. J. Biol. Chem. 270: 20530-20535 (1995).

Bridges M, Jones AME, Bones AM, Hodgson C, Cole R, Bartlet E, Wallsgrove R, Karapapa VK, Watts N, Rossiter JT. Spatial organization of the glucosinolate-myrosinase system in brassica specialist aphids is similar to that of the host plant. Proc. Roy. Soc. Lond. B. Biol. Sci. 269: 187-191 (2002).

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

Burow M, Losansky A, Muller R, Plock A, Kliebenstein DJ, Wittstock U. The genetic basis of constitutive and herbivore-induced ESP-independent nitrile formation in Arabidopsis thaliana. Plant Physiol. 149: 561-574 (2009).

Burow M, Rice M, Hause B, Gershenzon J, Wittstock U. Cell- and tissue-specific localization and regulation of the epithiospecifier protein in Arabidopsis thaliana. Plant Mol. Biol. 64: 173-185 (2007).

Burow M, Zhang ZY, Ober JA, Lambrix VM, Wittstock U, Gershenzon J, Kliebenstein DJ. ESP and ESM1 mediate indol-3-acetonitrile production from indol-3-ylmethyl glucosinolate in Arabidopsis. Phytochemistry 69: 663-671 (2008).

Capella AN, Menossi M, Arruda P, Benedetti CE. COI1 affects myrosinase activity and controls the expression of two flower-specific myrosinase-binding protein homologues in Arabidopsis. Planta 213: 691-699 (2001).

Celenza JL. Metabolism of tyrosine and tryptophan - new genes for old pathways. Curr. Opin. Plant Biol. 4: 234-240 (2001).

Cottaz S, Henrissat B, Driguez H. Mechanism-based inhibition and stereochemistry of glucosinolate hydrolysis by myrosinase. Biochemistry 35: 15256-15259 (1996).

Du L, Halkier BA. Isolation of a microsomal enzyme system involved in glucosinolate biosynthesis from seedlings of Tropaeolum majus L. Plant Physiol. 111: 831-837 (1996).

Du L, Lykkesfeldt J, Olsen CE, Halkier BA. Involvement of cytochrome P450 in oxime production in glucosinolate biosynthesis as demonstrated by an in vitro microsomal enzyme system isolated from jasmonic acid-induced seedlings of Sinapis alba L. Proc. Natl. Acad. Sci. U.S.A. 92: 12505-12509 (1995).

Eriksson S, Andreasson E, Ekbom B, Graner G, Pontoppidan B, Taipalensuu J, Zhang J, Rask L, Meijer J. Complex formation of myrosinase isoenzymes in oilseed rape seeds are dependent on the presence of myrosinase-binding proteins. Plant Physiol. 129: 1592-1599 (2002).

Fahey JW, Zalcmann AT, Talalay P. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56: 5-51 (2001).

Fahey JW, Zhang Y, Talalay P. Broccoli sprouts: an exceptionally rich source of inducers of enzymes that protect against chemical carcinogens. Proc. Natl. Acad. Sci. U.S.A. 94: 10367-10372 (1997).

Falk A, Taipalensuu J, Ek B, Lenman M, Rask L. Characterization of rapeseed myrosinase-binding protein. Planta 195: 387-395 (1995).

Francis F, Lognay G, Wathelet JP, Haubruge E. Characterisation of aphid myrosinase and degradation studies of glucosinolates. Arch. Insect Biochem. Physiol. 50: 173-182 (2002).

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

Hansen BG, Halkier BA. New insight into the biosynthesis and regulation of indole compounds in Arabidopsis thaliana. Planta 221: 603-606 (2005).

Hayes JD, Kelleher MO, Eggleston IM. The cancer chemopreventive actions of phytochemicals derived from glucosinolates. Eur. J. Nutr. 47 Suppl. 2: 73-88 (2008).

Heiss S, Schafer HJ, Haag-Kerwer A, Rausch T. Cloning sulfur assimilation genes of Brassica juncea L.: cadmium differentially affects the expression of a putative low-affinity sulfate transporter and isoforms of ATP sulfurylase and APS reductase. Plant Mol. Biol. 39: 847-857 (1999).

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

Iori R, Rollin P, Streicher H, Thiem J, Palmieri S. The myrosinase-glucosinolate interaction mechanism studied using some synthetic competitive inhibitors. FEBS Lett. 385: 87-90 (1996).

Johnson IT. Glucosinolates: Bioavailability and importance to health. Int. J. Vitam. Nutr. Res. 72: 26-31 (2002).

Jones AME, Winge P, Bones AM, Cole R, Rossiter JT. Characterization and evolution of a myrosinase from the cabbage aphid Brevicoryne brassicae. Insect Biochem. Mol. Biol. 32: 275-284 (2002).

Kelly PJ, Bones A, Rossiter JT. Sub-cellular immunolocalization of the glucosinolate sinigrin in seedlings of Brassica juncea. Planta 206: 370-377 (1998).

Kim HJ, Chen F, Wang X, Choi JH. Effect of methyl jasmonate on phenolics, isothiocyanate, and metabolic enzymes in radish sprout (Raphanus sativus L.). J. Agric. Food Chem. 54: 7263-7269 (2006).

Kim JH, Jander G. Myzus persicae (green peach aphid) feeding on Arabidopsis induces the formation of a deterrent indole glucosinolate. Plant J. 49: 1008-1019 (2007).

Kim JH, Lee BW, Schroeder FC, Jander G. Identification of indole glucosinolate breakdown products with antifeedant effects on Myzus persicae (green peach aphid). Plant J. 54: 1015-1026 (2008).

Kliebenstein D, Pedersen D, Barker B, Mitchell-Olds T. Comparative analysis of quantitative trait loci controlling glucosinolates, myrosinase and insect resistance in Arabidopsis thaliana. Genetics 161: 325-332 (2002).

Kliebenstein DJ, Kroymann J, Mitchell-Olds T. The glucosinolate-myrosinase system in an ecological and evolutionary context. Curr. Opin. Plant Biol. 8: 264-271 (2005).

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

Krul C, Humblot C, Philippe C, Vermeulen M, van Nuenen M, Havenaar R, Rabot S. Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic in vitro large-intestinal model. Carcinogenesis 23: 1009-1016 (2002).

Kusnierczyk A, Winge P, Midelfart H, Armbruster WS, Rossiter JT, Bones AM. Transcriptional responses of Arabidopsis thaliana ecotypes with different glucosinolate profiles after attack by polyphagous Myzus persicae and oligophagous Brevicoryne brassicae. J. Exp. Bot. 58: 2537-2552 (2007).

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

Lefoix M, Tatibouet A, Cottaz S, Driguez H, Rollin P. Carba-glucotropaeolin: the first non-hydrolyzable glucosinolate analogue, to inhibit myrosinase. Tetrahedron Lett. 43: 2889-2890 (2002).

Lenman M, Falk A, Rodin J, Hoglund AS, Ek B, Rask L. Differential expression of myrosinase gene families. Plant Physiol. 103: 703-711 (1993).

Leoni O, Iori R, Palmieri S, Esposito E, Menegatti E, Cortesi R, Nastruzzi C. Myrosinase-generated isothiocyanate from glucosinolates: isolation, characterization and in vitro antiproliferative studies. Bioorg. Med. Chem. 5: 1799-1806 (1997).

Ludikhuyze L, Rodrigo L, Hendrickx M. The activity of myrosinase from broccoli (Brassica oleracea L. cv. Italica): influence of intrinsic and extrinsic factors. J. Food Prot. 63: 400-403 (2000).

Matusheski NV, Jeffery EH. Comparison of the bioactivity of two glucoraphanin hydrolysis products found in broccoli, sulforaphane and sulforaphane nitrile. J. Agric. Food Chem. 49: 5743-5749 (2001).

Matusheski NV, Juvik JA, Jeffery EH. Heating decreases epithiospecifier protein activity and increases sulforaphane formation in broccoli. Phytochemistry 65: 1273-1281 (2004).

Mithen R. Glucosinolates - biochemistry, genetics and biological activity. Plant Growth Regul. 34: 91-103 (2001).

Muller C, Agerbirk N, Olsen CE, Boeve JL, Schaffner U, Brakefield PM. Sequestration of host plant glucosinolates in the defensive hemolymph of the sawfly Athalia rosae. J. Chem. Ecol. 27: 2505-2516 (2001).

Mumm R, Burow M, Bukovinszkine'kiss G, Kazantzidou E, Wittstock U, Dicke M, Gershenzon J. Formation of simple nitriles upon glucosinolate hydrolysis affects direct and indirect defense against the specialist herbivore, Pieris rapae. J. Chem. Ecol. 34: 1311-1321 (2008).

Nakamura Y, Nakamura K, Asai Y, Wada T, Tanaka K, Matsuo T, Okamoto S, Meijer J, Kitamura Y, Nishikawa A, Park EY, Sato K, Ohtsuki K. Comparison of the glucosinolate-myrosinase systems among daikon (Raphanus sativus, Japanese white radish) varieties. J. Agric. Food Chem. 56: 2702-2707 (2008).

Perocco P, Iori R, Barillari J, Broccoli M, Sapone A, Affatato A, Paolini M. In vitro induction of benzo(a)pyrene cell-transforming activity by the glucosinolate gluconasturtiin found in cruciferous vegetables. Cancer Lett. 184: 65-71 (2002).

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

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

Prestera T, Fahey JW, Holtzclaw WD, Abeygunawardana C, Kachinski JL, Talalay P. Comprehensive chromatographic and spectroscopic methods for the separation and identification of intact glucosinolates. Anal. Biochem. 239: 168-179 (1996).

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

Ratzka A, Vogel H, Kliebenstein DJ, Mitchell-Olds T, Kroymann J. Disarming the mustard oil bomb. Proc. Natl. Acad. Sci. U.S.A. 99: 11223-11228 (2002).

Reifenrath K, Muller C. Species-specific and leaf-age dependent effects of ultraviolet radiation on two Brassicaceae. Phytochemistry 68: 875-885 (2007).

Sakorn P, Rakariyatham N, Niamsup H, Nongkunsarn P. Rapid detection of myrosinase-producing fungi: a plate method based on opaque barium sulphate formation. World J. Microbiol. Biotechnol. 18: 73-74 (2002).

Serra B, Rosa E, Iori R, Barillari J, Cardoso A, Abreu C, Rollin P. In vitro activity of 2-phenylethyl glucosinolate, and its hydrolysis derivatives on the root-knot nematode Globodera rostochiensis (Woll.). Sci. Hortic. 92: 75-81 (2002).

Sexton AC, Kirkegaard JA, Howlett BJ. Glucosinolates in Brassica juncea and resistance to Australian isolates of Leptosphaeria maculans, the blackleg fungus. Australasian Plant Pathol. 28: 95-102 (1999).

Shapiro TA, Fahey JW, Wade KL, Stephenson KK, Talalay P. Human metabolism and excretion of cancer chemoprotective glucosinolates and isothiocyanates of cruciferous vegetables. Cancer Epidemiol. Biomarkers Prev. 7: 1091-1100 (1998).

Sherameti I, Venus Y, Drzewiecki C, Tripathi S, Dan VM, Nitz I, Varma A, Grundler FM, Oelmüller R. PYK10, a beta-glucosidase located in the endoplasmatic reticulum, is crucial for the beneficial interaction between Arabidopsis thaliana and the endophytic fungus Piriformospora indica. Plant J. 54: 428-439 (2008).

Shikita M, Fahey JW, Golden TR, Holtzclaw WD, Talalay P. An unusual case of 'uncompetitive activation' by ascorbic acid: purification and kinetic properties of a myrosinase from Raphanus sativus seedlings. Biochem. J. 341: 725-732 (1999).

Shroff R, Vergara F, Muck A, Svatos A, Gershenzon J. Nonuniform distribution of glucosinolates in Arabidopsis thaliana leaves has important consequences for plant defense. Proc. Natl. Acad. Sci. U.S.A. 105: 6196-6201 (2008).

Siemens DH, Garner SH, Mitchell-Olds T, Callaway RM. Cost of defense in the context of plant competition: Brassica rapa may grow and defend. Ecology 83: 505-517 (2002).

Smiechowska A, Bartoszek A, Namiesnik J. Cancer chemopreventive agents: glucosinolates and their decomposition products in white cabbage (Brassica oleracea var. capitata). Postepy. Hig. Med. Dosw. (Online) 62: 125-140 (2008).

Taipalensuu J, Andreasson E, Eriksson S, Rask L. Regulation of the wound-induced myrosinase-associated protein transcript in Brassica napus plants. Eur. J. Biochem. 247: 963-971 (1997).

Taipalensuu J, Falk A, Rask L. A wound- and methyl jasmonate-inducible transcript coding for a myrosinase-associated protein with similarities to an early nodulin. Plant Physiol. 110: 483-491 (1996).

Takechi K, Sakamoto W, Utsugi S, Murata M, Motoyoshi F. Characterization of a flower-specific gene encoding a putative myrosinase binding protein in Arabidopsis thaliana. Plant Cell Physiol. 40: 1287-1296 (1999).

Takeda M, Sugimori N, Torizawa T, Terauchi T, Ono AM, Yagi H, Yamaguchi Y, Kato K, Ikeya T, Jee J, Guntert P, Aceti DJ, Markley JL, Kainosho M. Structure of the putative 32 kDa myrosinase-binding protein from Arabidopsis (At3g16450.1) determined by SAIL-NMR. FEBS J. 275: 5873-5884 (2008).

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

van Poppel G, Verhoeven DT, Verhagen H, Goldbohm RA. Brassica vegetables and cancer prevention. Epidemiology and mechanisms. Adv. Exp. Med. Biol. 472: 159-68 (1999).

Vergara F, Wenzler M, Hansen BG, Kliebenstein DJ, Halkier BA, Gershenzon J, Schneider B. Determination of the absolute configuration of the glucosinolate methyl sulfoxide group reveals a stereospecific biosynthesis of the side chain. Phytochemistry 69: 2737-2742 (2008).

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Wallace SK, Eigenbrode SD. Changes in the glucosinolate-myrosinase defense system in Brassica juncea cotyledons during seedling development. J. Chem. Ecol. 28: 243-256 (2002).

Warton B, Matthiessen JN, Shackleton MA. Glucosinolate content and isothiocyanate evolution - Two measures of the biofumigation potential of plants. J. Agric. Food Chem. 49: 5244-5250 (2001).

Wentzell AM, Kliebenstein DJ. Genotype, age, tissue, and environment regulate the structural outcome of glucosinolate activation. Plant Physiol. 147: 415-428 (2008).

Williams DJ, Critchley C, Pun S, Nottingham S, O'Hare TJ. Epithiospecifier protein activity in broccoli: the link between terminal alkenyl glucosinolates and sulphoraphane nitrile. Phytochemistry 69: 2765-2773 (2008).

Wittstock U, Halkier BA. Glucosinolate research in the Arabidopsis era. Trends Plant Sci. 7: 263-270 (2002).

Xue JP, Lenman M, Falk A, Rask L. The glucosinolate-degrading enzyme myrosinase in Brassicaceae is encoded by a gene family. Plant Mol. Biol. 18: 387-398 (1992).

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Zhang JM, Pontoppidan B, Xue JP, Rask L, Meijer J. The third myrosinase gene TGG3 in Arabidopsis thaliana is a pseudogene specifically expressed in stamen and petal. Physiol. Plant. 115: 25-34 (2002).

Zhang Z, Ober JA, Kliebenstein DJ. The gene controlling the quantitative trait locus EPITHIOSPECIFIER MODIFIER1 alters glucosinolate hydrolysis and insect resistance in Arabidopsis. Plant Cell 18: 1524-1536 (2006).

Zhao Z, Zhang W, Stanley BA, Assmann SM. Functional proteomics of Arabidopsis thaliana guard cells uncovers new stomatal signaling pathways. Plant Cell 20: 3210-3226 (2008).

Number of references = 85

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Last Update: 10/01/09