Biology and biochemistry of glucosinolates

Annual Review of Plant Biology

Volumn 57, Issue , 2006, Pages 303-333

  Halkier, Barbara Ann ^a   Gershenzon, Jonathan ^b  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

Biosynthesis; Defense; Degradation; Metabolic engineering; Regulation; Transport

Indexed keywords

GLUCOSINOLATE;

BIOSYNTHESIS; CHEMISTRY; METABOLISM; PLANT; REVIEW;

GLUCOSINOLATES; PLANTS;

ARABIDOPSIS;

EID: 33745218882     PISSN: 15435008     EISSN: None     Source Type: Book Series    
DOI: 10.1146/annurev.arplant.57.032905.105228     Document Type: Review

References (179)

1. Agerbirk N, Olsen CE, Soerensen H. 1998. Initial and final products, nitriles, and ascorbigens produced in myrosinase-catalyzed hydrolysis of indole glucosinolates. J. Agric. Food Chem. 46:1563-71
2. Agrawal AA, Conner JK, Johnson MTJ, Wallsgrove R. 2002. Ecological genetics of an induced plant defense against herbivores: additive genetic variance and costs of phenotypic plasticity. Evolution 56:2206-13
3. Agrawal AA, Kurashige NS. 2003. A role for isothiocyanates in plant resistance against the specialist herbivore Pieris rapae. J. Chem. Ecol. 29:1403-15
4. Aliabadi A, Renwick JAA, Whitman DW. 2002. Sequestration of glucosinolates by harlequin bug Murgantia histrionica. J. Chem. Ecol. 28:1749-62
5. Andersen MD, Busk PK, Svendsen I, Moller BL. 2000. Cytochromes P-450 from cassava (Manihot esculenta Crantz) catalyzing the first steps in the biosynthesis of the cyanogenic glucosides linamarin and lotaustralin-cloning, functional expression in Pichia pastoris, and substrate specificity of the isolated recombinant enzymes. J. Biol. Chem. 275:1966-75
6. Andreasson E, Jorgensen LB, Hoglund AS, Rask L, Meijer J. 2001. Different myrosinase and idioblast distribution in Arabidopsis and Brassica napus. Plant Physiol. 127:1750-63
7. Andreasson E, Taipalensuu J, Rask L, Meijer J. 1999. Age-dependent wound induction of a myrosinase-associated protein from oilseed rape (Brassica napus). Plant Mol. Biol. 41:171-80
8. Bak S, Feyereisen R. 2001. The involvement of two P450 enzymes, CYP83B1 and CYP83A1, in auxin homeostasis and glucosinolate biosynthesis. Plant Physiol. 127:108-18
9. Bak S, Kahn RA, Nielsen HL, Moller BL, Halkier BA. 1998. Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moech by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin. Plant Mol. Biol. 36:393-405
10. Bak S, Olsen CE, Petersen BL, Moller BL, Halkier BA. 1999. Metabolic engineering of p-hydroxybenzylglucosinolate in Arabidopsis by expression of the cyanogenic CYP79A1 from Sorghum bicolor. Plant J. 20:663-71
11. Bak S, Tax FE, Feldmann KA, Galbraith DW, Feyereisen R. 2001. CYP83B1, a cytochrome P450 at the metabolic branch paint in auxin and indole glucosinolate biosynthesis in Arabidopsis. Plant Cell 13:101-11
12. Barlier I, Kowalczyk M, Marchant A, Ljung K, Bhalerao R, et al. 2000. The SUR2 gene of Arabidopsis thaliana encodes the cytochrome P450 CYP83B1, a modulator of auxin homeostasis. Proc. Natl. Acad. Sci. USA 97:14819-24
13. Bender J, Fink GR. 1998. A Myb homologue, ATR1, activates tryptophan gene expression in Arabidopsis. Proc. Natl. Acad. Sci. USA 95:5655-60
14. Bernardi R, Finiguerra MG, Rossi AA, Palmieri S. 2003. Isolation and biochemical characterization of a basic myrosinase from ripe Crambe abyssinica seeds, highly specific for epi-progoitrin. J. Agric. Food Chem. 51:2737-44
15. Bernardi R, Negri A, Ronchi S, Palmieri S. 2000. Isolation of the epithiospecifier protein from oil-rape (Brassica napus ssp oleifera) seed and its characterization. FEBS Lett. 467:296-98
16. Bodnaryk RP. 1992. Effects of wounding on glucosinolates in the cotyledons of oilseed rape and mustard. Phytochemistry 31:2671-77
17. Bodnaryk RP. 1994. Potent effect of jasmonates on indole glucosinolates in oilseed rape and mustard. Phytochemistry 35:301-5
18. Boerjan W, Cervera MT, Delarue M, Beeckman T, Dewitte W, et al. 1995. Superroot, a recessive mutation in Arabidopsis, confers auxin overproduction. Plant Cell 7:1405-19
19. Bones AM, Rossiter JT. 1996. The myrosinase-glucosinolate system, its organisation and biochemistry. Physiol. Plant. 97:194-208
20. 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. 126:849-60
21. Bridges M, Jones AME, Bones AM, Hodgson C, Cole R, et al. 2002. Spatial organization of the glucosinolate-myrosinase system in Brassica specialist aphids is similar to that of the host plant. Proc. R. Soc. London Sci. Ser. B 269:187-91
22. Brown PD, Morra MJ. 1995. Glucosinolate-containing plant tissues as bioherbicides. J. Agric. Food Chem. 43:3070-74
23. Brown PD, Tokuhisa JG, Reichelt M, Gershenzon J. 2003. Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana. Phytochemistry 62:471-81
24. Brudenell AJP, Griffiths H, Rossiter JT, Baker DA. 1999. The phloem mobility of glucosinolates. J. Exp. Bot. 50:745-56
25. Burmeister WP, Cottaz S, Driguez H, Iori R, Palmieri S, Henrissat B. 1997. The crystal structures of Sinapis alba myrosinase and a covalent glycosyl-enzyme intermediate provide insights into the substrate recognition and active-site machinery of an S-glycosidase. Structure 5:663-75
26. Burmeister WP, Cottaz S, Rollin P, Vasella A, Henrissat B. 2000. 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. 275:39385-93
27. Buskov S, Olsen CE, Sorensen H, Sorensen S. 2000. Supercritical fluid chromatography as basis for identification and quantitative determination of indol-3-ylmethyl oligomers and ascorbigens. J. Biochem. Biophys. Methods 43:175-95
28. Buskov S, Serra B, Rosa E, Soerensen H, Soerensen JC. 2002. Effects of intact glucosinolates and products produced from glucosinolates in myrosinase-catalyzed hydrolysis on the potato cyst nematode (Globodera rostochiensis cv. Woll). J. Agric. Food Chem. 50:690-95
29. Campos de Quiros HC, Magrath R, McCallum D, Kroymann J, Schnabelrauch D, et al. 2000. Alpha-keto acid elongation and glucosinolate biosynthesis in Arabidopsis thaliana. Theor. Appl. Genet. 101:429-37
30. Celenza JL, Grisafi PL, Fink GR. 1995. A pathway for lateral root-formation in Arabidopsis thaliana. Genes Dev. 9:2131-42
31. Celenza JL, Quiel JA, Smolen GA, Merrikh H, Silvestro AR, et al. 2005. The Arabidopsis ATR1 Myb transcription factor controls indolic glucosinolate homeostasis. Plant Physiol. 137:253-62
32. Chapple CCS, Decicco C, Ellis BE. 1988. Biosynthesis of 2-(2′-methylthio)ethylmalate in Brassica carinata. Phytochemistry 27:3461-63
33. Chapple CCS, Glover JR, Ellis BE. 1990. Purification and characterization of methionine: glyoxylate aminotransferase from Brassica napus. Plant Physiol. 94:1887-96
34. Chen S, Glaswischnig E, Jorgensen K, Naur P, Jorgensen B, et al. 2003. CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis. Plant J. 33:923-37
35. Chen S, Petersen BL, Olsen CE, Schulz A, Halkier BA. 2001. Long-distance phloem transport of glucosinolates in Arabidopsis. Plant Physiol. 127:194-201
36. Chen SX, Halkier BA. 1999. Functional expression and characterization of the myrosinase MYR1 from Brassica napus in Saccharomyces cerevisiae. Protein Expr. Purif. 17:414-20
37. Chen SX, Halkier BA. 2000. Characterization of glucosinolate uptake by leaf protoplasts of Brassica napus. J. Biol. Chem. 275:22955-60
38. Chew FS. 1988. Biological effects of glucosinolates. In Biologically Active Natural Products, ed. HG Cutler, pp. 155-81. Washington, DC: ACS
39. 14 and related compounds to horseradish. Can. J. Biochem. 42:1033-40
40. Cole R. 1976. Isothiocyanates, nitriles and thiocyanates as products of autolysis of glucosinolates in Cruciferae. Phytochemistry 15:759-62
41. de Jong R, Maher N, Patrian B, Stadler E, Winkler T. 2000. Rutabaga roots, a rich source of oviposition stimulants for the cabbage root fly. Chemoecology 10:205-9
42. Delarue M, Prinsen E, Van Onckelen H, Caboche M, Bellini C. 1998. Sur2 mutations of Arabidopsis thaliana define a new locus involved in the control of auxin homeostasis. Plant J. 14:603-11
43. 3 mustard oil glucoside. Can. J. Biochem. 52:916-21
44. Doughty KJ, Kiddle GA, Pye BJ, Wallsgrove RM, Pickett JA. 1995. Selective induction of glucosinolates in oilseed rape leaves by methyl jasmonate. Phytochemistry 38:347-50
45. Du LC, Halkier BA. 1998. Biosynthesis of glucosinolates in the developing silique walls and seeds of Sinapis alba. Phytochemistry 48:1145-50
46. Engel E, Baty C, le Corre D, Souchon I, Martin N. 2002. Flavor-active compounds potentially implicated in cooked cauliflower acceptance. J. Agric. Food Chem. 50:6459-67
47. Eriksson S, Andreasson E, Ekbom B, Graner G, Pontoppidan B, et al. 2002. Complex formation of myrosinase isoenzymes in oilseed rape seeds are dependent on the presence of myrosinase-binding proteins. Plant Physiol. 129:1592-99
48. Fahey JW, Haristoy X, Dolan PM, Kensler TW, Scholtus I, et al. 2002. Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors. Proc. Natl. Acad. Sci. USA 99:7610-15
49. Fahey JW, Zalcmann AT, Talalay P. 2001. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56:5-51
50. Falk KL, Vogel C, Textor S, Bartram S, Hick A, et al. 2004. Glucosinolate biosynthesis: demonstration and characterization of the condensing enzyme of the chain elongation cycle in Eruca sativa. Phytochemistry 65:1073-84
51. Field B, Cardon G, Traka M, Botterman J, Vancanneyt G, Mithen R. 2004. Glucosinolate and amino acid biosynthesis in Arabidopsis. Plant Physiol. 135:828-39
52. Foo HL, Gronning LM, Goodenough L, Bones AM, Danielsen BE, et al. 2000. Purification and characterisation of epithiospecifier protein from Brassica napus: enzymic intramolecular sulphur addition within alkenyl thiohydroximates derived from alkenyl glucosinolate hydrolysis. FEBS Lett. 468:243-46
53. Gabrys B, Tjallingii WF. 2002. The role of sinigrin in host plant recognition by aphids during initial plant penetration. Entomol. Exp. Appl. 104:89-93
54. Galletti S, Bernardi R, Leoni O, Rollin P, Palmieri S. 2001. Preparation and biological activity of four epiprogoitrin myrosinase-derived products. J. Agric. Food Chem. 49:471-76
55. Gao MQ, Li GY, 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 47:666-79
56. Giamoustaris A, Mithen R. 1996. Genetics of aliphatic glucosinolates. 4. Side-chain modification in Brassica oleracea. Theor. Appl. Genet. 93:1006-10
57. Gijzen M, McGregor I, Seguinswartz G. 1989. Glucosinolate uptake by developing rape-seed embryos. Plant Physiol. 89:260-63
58. Gil V, MacLeod AJ. 1980. The effects of pH on glucosinolate degradation by a thioglucoside glucohydrolase preparation. Phytochemistry 19:2547-51
59. Glawischnig E, Hansen BG, Olsen CE, Halkier BA. 2004. Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis. Proc. Natl. Acad. Sci. USA 101:8245-50
60. Glover JR, Chapple CCS, Rothwell S, Tober I, Ellis BE. 1988. Allylglucosinolate biosynthesis in Brassica carinata. Phytochemistry 27:1345-48
61. Graser G, Oldham NJ, Brown PD, Temp U, Gershenzon J. 2001. The biosynthesis of benzoic acid glucosinolate esters in Arabidopsis thaliana. Phytochemistry 57:23-32
62. Graser G, Schneider B, Oldham NJ, Gershenzon J. 2000. The methionine chain elongation pathway in the biosynthesis of glucosinolates in Eruca sativa (Brassicaceae). Arch. Biochem. Biophys. 378:411-19
63. Griffiths DW, Birch ANE, Hillman JR. 1998. Antinutritional compounds in the Brassicaceae-Analysis, biosynthesis, chemistry and dietary effects. J. Hort. Sci. Biotech. 73:1-18
64. Griffiths DW, Deighton N, Birch ANE, Patrian B, Baur R, Stadler E. 2001. Identification of glucosinolates on the leaf surface of plants from the Cruciferae and other closely related species. Phytochemistry 57:693-700
65. Grubb CD, Zipp BJ, Ludwig-Muller J, Masuno MN, Molinski TF, Abel S. 2004. Arabidopsis glucosyltransferase UGT74B1 functions in glucosinolate biosynthesis and auxin homeostasis. Plant J. 40:893-908
66. Halkier BA, Hansen CH, Mikkelsen MD, Naur P, Wittstock U. 2002. The role of cytochromes P450 in biosynthesis and evolution of glucosinolates. In Phytochemistry in the Genomics and Post-genomics Eras, ed. JT Romeo, RA Dixon, pp. 223-48. Amsterdam: Elsevier
67. Hall C, McCallum D, Prescott A, Mithen R. 2001. Biochemical genetics of glucosinolate modification in Arabidopsis and Brassica. Theor. Appl. Genet. 102:369-74
68. Hansen CH, Du LC, Naur P, Olsen CE, Axelsen KB, et al. 2001. CYP83B1 is the oxime-metabolizing enzyme in the glucosinolate pathway in Arabidopsis. J. Biol. Chem. 276:24790-96
69. 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. 276:11078-85
70. Hasapis X, MacLeod AJ. 1982. Benzylglucosinolate degradation in heat-treated Lepidium sativum seeds and detection of a thiocyanate-forming factor. Phytochemistry 21:1009-13
71. 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 15:179-94
72. Hirai MY, Klein M, Fujikawa Y, Yano M, Goodenowe DB, et al. 2005. Elucidation of gene-to-gene and metabolite-to-gene networks in Arabidopsis by integration of metabolomics and transcriptomics. J. Biol. Chem. 280:25590-95
73. 72b. Holst B, Williamson G. 2004. A critical review of the bioavailability of glucosinolates and related compounds. Nat. Prod. Rep. 21:425-47
74. 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 97:2379-84
75. 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. 128:1180-88
76. Iqbal MCM, Moellers C. 2003. Uptake and distribution of sinigrin in microspore derived embryos of Brassica napus L. J. Plant Physiol. 160:961-66
77. Ishimoto H, Fukushi Y, Yoshida T, Tahara S. 2000. Rhizopus and Fusarium are selected as dominant fungal genera in rhizospheres of Brassicaceae. J. Chem. Ecol. 26:2387-99
78. Jones AME, Winge P, Bones AM, Cole R, Rossiter JT. 2002. Characterization and evolution of a myrosinase from the cabbage aphid Brevicoryne brassicae. Insect Biochem. Mol. Biol. 32:275-84
79. Jones PR, Andersen MD, Nielsen JS, Hoj PB, Moller BL. 2000. The biosynthesis, degradation, transport and possible function of cyanogenic glucosides. In Evolution of Metabolic Pathways, ed. JT Romeo, R Ibrahim, L Varin, pp. 191-247. Amsterdam: Elsevier
80. Kawakishi S, Kaneko T. 1987. Interaction of proteins with allyl isothiocyanate. J. Agric. Food Chem. 35:85-88
81. Kelly PJ, Bones A, Rossiter JT. 1998. Sub-cellular immunolocalization of the glucosinolate sinigrin in seedlings of Brassica juncea. Planta 206:370-77
82. Keum YS, Jeong WS, Kong ANT. 2004. Chemoprevention by isothiocyanates and their underlying molecular signaling mechanisms. Mutat. Res. Fundam. Mol. Mech. Mutagen. 555:191-202
83. Kiddle GA, Doughty KJ, Wallsgrove RM. 1994. Salicylic acid-induced accumulation of glucosinolates in oilseed rape (Brassica napus L) leaves. J. Exp. Bot. 45:1343-46
84. King JJ, Stimart DP, Fisher RH, Bleecker AB. 1995. A mutation altering auxin homeostasis and plant morphology in Arabidopsis. Plant Cell 7:2023-37
85. Kliebenstein DJ, Figuth A, Mitchell-Olds T. 2002. Genetic architecture of plastic methyl jasmonate responses in Arabidopsis thaliana. Genetics 161:1685-96
86. Kliebenstein DJ, Gershenzon J, Mitchell-Olds T. 2001. Comparative quantitative trait loci mapping of aliphatic, indolic and benzylic glucosinolate production in Arabidopsis thaliana leaves and seeds. Genetics 159:359-70
87. Kliebenstein DJ, Kroymann J, Brown P, Figuth A, Pedersen D, et al. 2001. Genetic control of natural variation in Arabidopsis glucosinolate accumulation. Plant Physiol. 126:811-25
88. Kliebenstein DJ, Lambrix VM, Reichelt M, Gershenzon J, Mitchell-Olds T. 2001. Gene duplication in the diversification of secondary metabolism: tandem 2-oxoglutarate-dependent dioxygenases control glucosinolate biosynthesis in Arabidopsis. Plant Cell 13:681-93
89. 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
90. Kroumova AB, Wagner GJ. 2003. Different elongation pathways in the biosynthesis of acyl groups of trichome exudate sugar esters from various solanaceous plants. Planta 216:1013-21
91. Kroymann J, Donnerhacke S, Schnabelrauch D, Mitchell-Olds T. 2003. Evolutionary dynamics of an Arabidopsis insect resistance quantitative trait locus. Proc. Natl. Acad. Sci. USA 100:14587-92
92. Kroymann J, Textor S, Tokuhisa JG, Falk KL, Bartram S, et al. 2001. A gene controlling variation in Arabidopsis glucosinolate composition is part of the methionine chain elongation pathway. Plant Physiol. 127:1077-88
93. Krul C, Humblot C, Philippe C, Vermeulen M, van Nuenen M, et al. 2002. Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic in vitro large-intestinal model. Carcinogenesis 23:1009-16
94. Kutz A, Muller 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 J. 30:95-106
95. 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 13:2793-807
96. Latxague L, Gardrat C, Coustille JL, Viaud MC, Rollin P. 1991. Identification of enzymatic degradation products from synthesized glucobrassicin by gas chromatography-mass spectrometry. J. Chromatogr. 586:166-70
97. Lazzeri L, Curto G, Leoni O, Dallavalle E. 2004. Effects of glucosinolates and their enzymatic hydrolysis products via myrosinase on the root-knot nematode Meloidogyne incognita (Kofoid et White) Chitw. J. Agric. Food Chem. 52:6703-7
98. 15N]-2-amino-6-(methylthio)caproic acid in progoitrin biosynthesis. Biochemistry 9:2068-71
99. Lehman A, Black R, Ecker JR. 1996. HOOKLESS1, an ethylene response gene, is required for differential cell elongation in the Arabidopsis hypocotyl. Cell 85:183-94
100. Lenman M, Falk A, Roedin J, Hoeglund A-S, Ek B, Rask L. 1993. Differential expression of myrosinase gene families. Plant Physiol. 103:703-11
101. Li G, Riaz A, Goyal S, Abel S, Quiros CF. 2001. Inheritance of three major genes involved in the synthesis of aliphatic glucosinolates in Brassica oleracea. J. Am. Soc. Hortic. Sci. 126:427-31
102. Li Q, Eigenbrode SD, Stringam GR, Thiagarajah MR. 2000. Feeding and growth of Plutella xylostella and Spodoptera eridania on Brassica juncea with varying glucosinolate concentrations and myrosinase activities. J. Chem. Ecol. 26:2401-19
103. 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
104. Ljung K, Hull AK, Celenza JL, Yamada M, Estelle M, et al. 2005. Sites and regulation of auxin biosynthesis in Arabidopsis roots. Plant Cell 17:1090-104
105. Louda S, Mole S. 1991. Glucosinolates: chemistry and ecology. In Herbivores, Their Interactions with Secondary Plant Metabolites, ed. GA Rosenthal, MR Berenbaum, pp. 123-64. San Diego: Academic
106. Ludwig-Muller J, Hilgenberg W. 1988. A plasma membrane-bound enzyme oxidizes L-tryptophan to indole-3-acetaldoxime. Physiol. Plant. 74:240-50
107. Ludwig-Muller J, Rausch T, Langa S, Hilgenberg W. 1990. Plasma membrane bound high pI peroxidase isoenzymes convert tryptophan to indole-3-acetaldoxime. Phytochemistry 29:1397-400
108. Lund E. 2003. Non-nutritive bioactive constituents of plants: dietary sources and health benefits of glucosinolates. Int. J. Vitam. Nutr. Res. 73:135-43
109. Luthy B, Matile P. 1984. The mustard oil bomb: rectified analysis of the subcellular organization of the myrosinase system. Biochem. Physiol. Pflanz. 179:5-12
110. MacLeod AJ, Rossiter JT. 1985. The occurence and activity of epithiospecifier protein in some Cruciferae seeds. Phytochemistry 24:1895-98
111. MacLeod AJ, Rossiter JT. 1986. Isolation and examination of thioglucoside glucohydrolase from seeds of Brassica napus. Phytochemistry 25:1047-52
112. Magrath R, Bano F, Parkin I, Sharpe A, Lister C, et al. 1994. Genetics of aliphatic glucosinolates. I. Side chain elongation in Brassica napus and Arabidopsis thaliana. Heredity 72:290-99
113. Marazzi C, Stadler E. 2004. Arabidopsis thaliana leaf-surface extracts are detected by the cabbage root fly (Delia radicum) and stimulate oviposition. Physiol. Entomol. 29:192-98
114. Mari M, Leoni O, Iori R, Cembali T. 2002. Antifungal vapour-phase activity of allylisothiocyanate against Penicillium expansum on pears. Plant Pathol. 51:231-36
115. Merritt SZ. 1996. Within-plant variation in concentrations of amino acids, sugar, and sinigrin in phloem sap of black mustard, Brassica nigra (L) Koch (Cruciferae). J. Chem. Ecol. 22:1133-45
116. Mewis I, Apple 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. 138:1149-62
117. Mewis IZ, Ulrich C, Schnitzler WH. 2002. The role of glucosinolates and their hydrolysis products in oviposition and host-plant finding by cabbage webworm, Hellula undalis. Entomol. Exp. Appl. 105:129-39
118. 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. 275:33712-17
119. 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. 37:770-77
120. 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
121. Mikkelsen MD, Petersen BL, Olsen CE, Halkier BA. 2002. Biosynthesis and metabolic engineering of glucosinolates. Amino Acids 22:279-95
122. Miles CI, del Campo M, Renwick JAA. 2005. Behavioral and chemosensory responses to a host recognition cue by larvae of Pieris rapae. J. Comp. Phys. A 191:147-55
123. Mithen R, Campos H. 1996. Genetic variation of aliphatic glucosinolates in Arabidopsis thaliana and prospects for map based gene cloning. Entomol. Exp. Appl. 80:202-5
124. Mithen R, Clarke J, Lister C, Dean C. 1995. Genetics of aliphatic glucosinolates. 3. Side chain structure of aliphatic glucosinolates in Arabidopsis thaliana. 74:210-15
125. Mueller C, Agerbirk N, Olsen CE. 2003. Lack of sequestration of host plant glucosinolates in Pieris rapae and P. brassicae. Chemoecology 13:47-54
126. Mueller C, Agerbirk N, Olsen CE, Boeve JL, Schaffner U, Brakefield PM. 2001. Sequestration of host plant glucosinolates in the defensive hemolymph of the sawfly Athalia rosae. J. Chem. Ecol. 27:2505-16
127. Mueller C, Boeve JL, Brakefield P. 2002. Host plant derived feeding deterrence towards ants in the turnip sawfly Athalia rosae. Entomol. Exp. Appl. 104:153-57
128. Deleted in proof
129. Naur P, Petersen BL, Mikkelsen MD, Bak S, Rasmussen H, et al. 2003. CYP83A1 and CYP83B1, two nonredundant cytochrome P450 enzymes metabolizing oximes in the biosynthesis of glucosinolates in Arabidopsis. Plant Physiol. 133:67-72
130. Nielsen JK, Hansen ML, Agerbirk N, Petersen BL, Halkier BA. 2001. Responses of the flea beetles Phyllotreta nemorum and P. cruciferae to metabolically engineered Arabidopsis thaliana with an altered glucosinolate profile. Chemoecology 11:75-83
131. Nielsen KA, Møller BL. 2005. Cytochrome P450s in plants. In Cytochrome P450: Structure, Mechanism, and Biochemistry, ed. P Ortiz de Montellano, pp. 553-83. Kluwer Academic/Plenum
132. Noret N, Meerts P, Poschenrieder C, Barcelo J, Escarre J. 2005. Palatability of Thlaspi caerulescens for snails: influence of zinc and glucosinolates. New Phytol. 165:763-72
133. Parkin I, Magrath R, Keith D, Sharpe A, Mithen R, Lydiate D. 1994. Genetics of aliphatic glucosinolates. II. Hydroxylation of alkenyl glucosinolates in Brassica napus. Heredity 72:594-98
134. Pedras MSC, Montaut S, Xu Y, Khan AQ, Loukaci A. 2001. Assembling the biosynthetic puzzle of crucifer metabolites: Indole-3-acetaldoxime is incorporated efficiently into phytoalexins but glucobrassicin is not. Chem. Comm. 17:1572-73
135. Pedras MSC, Nycholat CM, Montaut S, Xu YM, Khan AQ. 2002. Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. Phytochemistry 59:611-25
136. Petersen BL, Chen SX, Hansen CH, Olsen CE, Halkier BA. 2002. Composition and content of glucosinolates in developing Arabidopsis thaliana. Planta 214:562-71
137. Piotrowski M, Schemenewitz A, Lopukhinat A, Mueller A, Janowitz T, et al. 2004. Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure. J. Biol. Chem. 279:50717-25
138. Pontoppidan B, Hopkins R, Rask L, Meijer J. 2003. Infestation by cabbage aphid (Brevicoryne brassicae) on oilseed rape (Brassica napus) causes a long lasting induction of the myrosinase system. Entomol. Exp. Appl. 109:55-62
139. Pontoppidan B, Hopkins R, Rask L, Meijer J. 2005. Differential wound induction of the myrosinase system in oilseed rape (Brassica napus): contrasting insect damage with mechanical damage. Plant Sci. 168:715-22
140. Prescott AG, John P. 1996. Dioxygenases-molecular structure and role in plant metabolism. Annu. Rev. Plant Physiol. Plant Mol. Biol. 47:245-71
141. 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
142. Ratzka A, Vogel H, Kliebenstein DJ, Mitchell-Olds T, Kroymann J. 2002. Disarming the mustard oil bomb. Proc. Natl. Acad. Sci. USA 99:11223-28
143. Reddy GVP, Guerrero A. 2000. Behavioral responses of the diamondback moth, Plutella xylostella, to green leaf volatiles of Brassica oleracea subsp. capitata. J. Agric. Food Chem. 48:6025-29
144. Reintanz B, Lehnen M, Reichelt M, Gershenzon J, Kowalczyk M, et al. 2001. Bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates. Plant Cell 13:351-67
145. Rodman JE, Karol KG, Price RA, Sytsma KJ. 1996. Molecules, morphology, and Dahlgrens expanded order Capparales. Syst. Bot. 21:289-307
146. Rojas JC. 1999. Electrophysiological and behavioral responses of the cabbage moth to plant volatiles. J. Chem. Ecol. 25:1867-83
147. Rouzaud G, Young SA, Duncan AJ. 2004. Hydrolysis of glucosinolates to isothiocyanates after ingestion of raw or microwaved cabbage by human volunteers. Cancer Epidemiol. Biomarkers Prev. 13:125-31
148. Sarwar M, Kirkegaard JA, Wong PTW, Desmarchelier JM. 1998. Biofumigation potential of Brassicas - III. In vitro toxicity of isothiocyanates to soil-borne fungal pathogens. Plant Soil 201:103-12
149. Smith BJ, Kirkegaard JA. 2002. In vitro inhibition of soil microorganisms by 2-phenylethyl isothiocyanate. Plant Pathol. 51:585-93
150. Smolen G, Bender J. 2002. Arabidopsis cytochrome p450 cyp83B1 mutations activate the tryptophan biosynthetic pathway. Genetics 160:323-32
151. Tantikanjana T, Yong JWH, Letham DS, Griffith M, Hussain M, et al. 2001. Control of axillary bud initiation and shoot architecture in Arabidopsis through the SUPERSHOOT gene. Genes Dev. 15:1577-88
152. Tattersall DB, Bak S, Jones PR, Olsen CE, Nielsen JK, et al. 2001. Resistance to an herbivore through engineered cyanogenic glucoside synthesis. Science 293:1826-28
153. Textor S, Bartram S, Kroymann J, Falk KL, Hick A, et al. 2004. Biosynthesis of methionine-derived glucosinolates in Arabidopsis thaliana: recombinant expression and characterization of methylthioalkylmalate synthase, the condensing enzyme of the chain-elongation cycle. Planta 218:1026-35
154. Thangstad OP, Bones AM. 2001. Microautoradiographic localisation of a glucosinolate precursor to specific cells in Brassica napus L. embryos indicates a separate transport pathway into myrosin cells. Planta 213:207-13
155. Thangstad OP, Gilde B, Chadchawan S, Seem M, Husebye H, et al. 2004. Cell specific, cross-species expression of myrosinases in Brassica napus, Arabidopsis thaliana and Nicotiana tabacum. Plant Mol. Biol. 54:597-611
156. Thornalley PJ. 2002. Isothiocyanates: mechanism of cancer chemopreventive action. Anti-Cancer Drugs 13:331-38
157. Tierens K, Thomma BPH, Brouwer M, Schmidt J, Kistner K, et al. 2001. Study of the role of antimicrobial glucosinolate-derived isothiocyanates in resistance of Arabidopsis to microbial pathogens. Plant Physiol. 125:1688-99
158. Tookey HL. 1973. Crambe thioglucoside glucohydrolase (EC 3.2.3.1): separation of a protein required for epithiobutane formation. Can. J. Biochem. 51:1654-60
159. Toroser D, Griffiths H, Wood C, Thomas DR. 1995. Biosynthesis and partitioning of individual glucosinolates between pod walls and seeds and evidence for the occurrence of PAPS:desulphoglucosinolate sulphotransferase in seeds of oilseed rape (Brassica napus L.). J. Exp. Bot. 46:1753-60
160. Toroser D, Thormann CE, Osborn TC, Mithen R. 1995. RFLP mapping of quantitative trait loci controlling seed aliphatic-glucosinolate content in oilseed rape (Brassica napus L.). Theor. Appl. Genet. 91:802-8
161. Traw MB. 2002. Is induction response negatively correlated with constitutive resistance in black mustard? Evolution 56:2196-205
162. Ulmer B, Gillott C, Erlandson M. 2001. Feeding preferences, growth, and development of Mamestra configurata (Lepidoptera: Noctuidae) on Brassicaceae. Can. Entomol. 133:509-19
163. Uzunova M, Ecke W, Weissleder K, Robbelen G. 1995. Mapping the genome of rapeseed (Brassica napus L). 1. Construction of an RFLP linkage map and localization of QTLS for seed glucosinolate content. Theor. Appl. Genet. 90:194-204
164. van Dam NM, Raaijmakers CE, van der Putten WH. 2005. Root herbivory reduces growth and survival of the shoot feeding specialist Pieris rapae on Brassica nigra. Entomol. Exp. Appl. 115:161-70
165. Vaughn SF, Isbell TA, Weisleder D, Berhow MA. 2005. Biofumigant compounds released by field pennycress (Thlaspi arvense) seedmeal. J. Chem. Ecol. 31:167-77
166. Vlieger L, Brakefield PM, Muller C. 2004. Effectiveness of the defence mechanism of the turnip sawfly, Athalia rosae (Hymenoptera: Tenthredinidae), against predation by lizards. Bull. Entomol. Res. 94:283-89
167. Wetter LR, Chisholm MD. 1968. Sources of sulfur in thioglucosides of various higher plants. Can. J. Biochem. 46:931-35
168. Wittstock U, Agerbirk N, Stauber EJ, Olsen CE, Hippler M, et al. 2004. Successful herbivore attack due to metabolic diversion of a plant chemical defense. Proc. Natl. Acad. Sci. USA 101:4859-64
169. Wittstock U, Halkier BA. 2000. Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. catalyzes the conversion of L-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate. J. Biol. Chem. 275:14659-66
170. Wittstock U, Halkier BA. 2002. Glucosinolate research in the Arabidopsis era. Trends Plant Sci. 7:263-70
171. Wittstock U, Kliebenstein DJ, Lambrix VM, Reichelt M, Gershenzon J. 2003. Glucosinolate hydrolysis and its impact on generalist and specialist insect herbivores. In Integrative Phytochemistry: from Ethnobotany to Molecular Ecology, ed. JT Romeo, pp. 101-25. Amsterdam: Elsevier
172. Xu Z, Escamilla-Trevino LL, Zeng L, Lalgondar M, Bevan DR, et al. 2004. Functional genomic analysis of Arabidopsis thaliana glycoside hydrolase family 1. Plant Mol. Biol. 55:343-67
173. Xue J, Pihlgren U, Rask L. 1993. Temporal, cell-specific, and tissue-preferential expression of myrosinase genes during embryo and seedling development in Sinapis alba. Planta 191:95-101
174. Xue JP, Jorgensen M, Pihlgren U, Rask L. 1995. The myrosinase gene family in Arabidopsis thaliana - gene organization, expression and evolution. Plant Mol. Biol. 27:911-22
175. Zasada IA, Ferris H. 2004. Nematode suppression with Brassicaceous amendments: application based upon glucosinolate profiles. Soil Biol. Biochem. 36:1017-24
176. Zeng RS, Mallik AU, Setliff E. 2003. Growth stimulation of ectomycorrhizal fungi by root exudates of Brassicaceae plants: Role of degraded compounds of indole glucosinolates. J. Chem. Ecol. 29:1337-55
177. Zhang Y, Talalay P, Cho C-G, Posner GH. 1992. A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc. Natl. Acad. Sci. USA 89:2399-403
178. Zhao Y, Christensen SK, Fankhauser C, Cashman JR, Cohen JD, et al. 2001. A role for flavin monooxygenase-like enzymes in auxin biosynthesis. Science 291:306-9
179. Zhao Y, Hull AK, Gupta NR, Goss KA, Alonso J, et al. 2002. Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3. Genes Dev. 16:3100-12