Skip to main content
Log in

Glucosinolates – biochemistry, genetics and biological activity

  • Published:
Plant Growth Regulation Aims and scope Submit manuscript

Abstract

This paper provides a brief overview of the biochemistry, genetics andbiological activity of glucosinolates and their degradation products.These compounds are found in vegetative and reproductive tissues of16 plant families, but are most well known as the major secondarymetabolites in the Brassicaceae. Following tissue disruption, theyare hydrolysed to a variety of products of which isothiocyanates(`mustard oils') are the most prominent. The majority of geneticstudies have concentrated on reducing the levels of these compoundsin the seeds of oilseed Brassica crops due to antinutritionalfactors associated with 2-hydroxy-3-butenyl glucosinolate. However,current interest is concerned with the anticarcinogenic activity ofisothiocyanates derived from cruciferous vegetables and salad crops.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Olsen O and Sørensen H (1979) Isolation of glucosinolates and the identification of o-(?-L-Rhamnopylransoyloxy)-benzylglucosinolate from Reseda odorata. Phytochem 18:1547

    Google Scholar 

  2. Linscheid M, Wendisch D and Strack D (1980) The structure of sinapic acid esters and their metabolism in cotyledons of Raphanus sativus. Z Naturforsch 35c: 907

    Google Scholar 

  3. Halkier BA (1999) Glucosinolates in Naturally occuring glycosides. In: Khan R (ed) Chemistry, Distribution and Biological Properties. John Wiley and Sons Ltd, pp 193–223

  4. Halkier BA and Du L (1997) The biosynthesis of glucosinolates. Trends in Plant Sci 2: 425–431

    Google Scholar 

  5. Underhill EW Chisholm MD and Wetter LR (1962) Biosynthesis of mustard oil glucosides. Administration of 14C-labelled compounds to horseradish, nasturtium and watercress. Can J Biochem Physiol 40: 1505–1514

    Google Scholar 

  6. Chisholm MD and Wetter LR (1964) Biosynthesis of mustard oil glucosides IV. The administration of methionine-14C and related compounds to horseradish. Can J Biochem 42: 1033–1040

    Google Scholar 

  7. Chapple CCS, Glover JR and Ellis BE (1990) Purification and characterisation of methionine-glyoxalate aminotransferase from Brassica carinata and Brassica napus. Plant Physiol 94:1887–1896

    Google Scholar 

  8. Strassman M and Ceci LN (1963) Enzymic formation of ?-isopropylmalic acid, an intermediate in leucine biosynthesis. J Biol Chem 238: 2445–2452

    Google Scholar 

  9. Umbarger HE (1997). Biosynthesis of branched-chain amino acids. In: Neidhardt FC (ed) Escherichia coli and Salmonella Cellular and Molecular Biology, Vol. 1, 2nd edn. Washington DC: ASM Press, pp 422–456

    Google Scholar 

  10. Du L, Lykkesfeldt J, Olsen CE and Halkier BA (1995) Involvment of cytochrome P450) in oxime production in glucosinolate biosynthesis as demonstrated by an in vitro microsomal enzyme system isolated from jasmonic acidinduced seedlings of Sinapis alba. Proc Natl Acad Sci USA 92: 12505–2509

    Google Scholar 

  11. Du L and Halkier BA (1996) Isolation of a microsomal enzyme system involved in glucosinolate biosynthesis from seedlings of Tropaeolum majus L. Plant Pysiol 111: 831–837

    Google Scholar 

  12. Halkier BA and Møller PL (1991) Involvment of cytochrome P450 in the biosynthesis of dhurrin in Sorghum bicolor. Plant Physiol 96: 10–17

    Google Scholar 

  13. Bennett RN, Kiddle G, Hick AJ, Dawson GW and Wallsgrove RM (1996) Distribution and activity of microsomal NADPH-dependent monooxygenase activity and amino acid decarboxylases in cruciferous and non-cruciferous plants, and their relationship to foliar glucosinolate content. Plant Cell Environ 19: 801–812

    Google Scholar 

  14. Bennett RN, Kiddle G and Wallsgrove RM (1997) Involvment of cytochrome P450 in glucosinolate biosynthesis in white mustard. Plant Physiol.114: 1283–1291

    Google Scholar 

  15. Dawson GW, Hick AJ, Bennet RN, Donald AM and Wallsgrove RM (1993) Synthesis of glucosinolate precursors and investigations into the biosynthesis of phenylalkyl-and methylthioalkylglucosinolates. J Biol Chem: 268: 27154–27159

    Google Scholar 

  16. Bennet RN, Donald AM, Dawson GW, Hick AJ and Wallsgrove RM (1993) Aldoxime-forming microsomal enzyme systems involved in the biosynthesis of glucosinolates in oilseed rape leaves. Plant Phyiol 102: 1307–1312 102

    Google Scholar 

  17. Bennet RN, Dawson GW, Hick AJ and Wallsgrove RM (1995) Glucosinolate biosynthesis: Further characterisation of the aldoxime-forming microsomal monooxygenases in oilseed rape leaves. Plant Physiol 109: 299–305

    Google Scholar 

  18. Ludwig-Müller J and Hilgenberg W (1988) A plasma membrane-bound enzyme oxidases L-tryptophan to indole-3-acetaldoxime. Physiol Plant 74: 240–250

    Google Scholar 

  19. Ludwig-Müller J, Rausch T, Lang S and Hilgenberg W(1990) Plasma membrane-bound higher plant isoenzymes convert tryptophan to indole-3-acetaldoxime Phytochem 29: 1397–1400

    Google Scholar 

  20. Wetter LR and Chisholm MD (1968) Sources of sulphur in the thioglucosides of various higher plants. Can J Biochem 46:931–935

    Google Scholar 

  21. Matsuo M and Undehill EW (1969) Biosynthesis of mustard oil glucosides XII. A UDP-glucose thiohydroxamate glycosyltransferase from Tropaeolum majus. Biochem Biophy Res Commun 36: 18–23

    Google Scholar 

  22. Reed DW, Davin L, Jain JC, Deluca V Nelson L and Underhill EW (1993) Purification and properties of UDP-glucose:Thiohydroximate glycosyltransfrase from Brassica napus L seedlings. Arch Biochem Biophys 305: 526–532

    Google Scholar 

  23. GrootWassink JWD, Reed DW and Kolenovsky AD (1994) Immunopurifcation and immunocharacterisation of the glucosinolate biosynthesis enzyme thiohydroximate Sglucosyltransferase. Plant Physiol 105: 425–433

    Google Scholar 

  24. Jain JC, Groot Wassink JWD, Kolenovsky AD and Underhill EW (1990) Purification and properties of 3′-phosphoadenosine-5′-phophosulphate:desulphoglucosinolate sulphotransferase from Brassica juncea cell cultures. Phytochem 29: 1425–1428

    Google Scholar 

  25. Glendenning TM and Poulton JE (1990) Partial purification and characterisation of a 3′-phophoadenosine 5'phosphosulphate: desulphoglucosinolate sulphotransferase from cress. Plant Physiol 94: 811–18

    Google Scholar 

  26. Jain JC, GrootWassink JWD, Reed DW and Underhill EW (1990) Persistent copurifcation of enzymes catalyzing the sequential glucosylation and sulphation steps in glucosinolate biosynthesis. J Plant Physiol 136: 356–361

    Google Scholar 

  27. Giamoustaris A and Mithen RF (1996) Genetics of aliphatic glucosinolates IV. Side chain modifications in Brassica oleracea. Theor Appl Genet 93: 1006–1010

    Google Scholar 

  28. Rossiter JT, James DC and Atkins N (1990) Biosynthesis of 2-hydroxy-3-butenyl glucosinolate and 3-butenyl glucosinolate in Brassica napus. Phytochem 29: 2509–2512

    Google Scholar 

  29. Parkin I, Magrath R, Keith D, Sharpe A, Mithen RF and Lydiate D (1994). Genetics of aliphatic glucosinolates II. Hydroxylation of alkenyl glucosinolates in Brassica napus. Heredity 72: 594–598

    Google Scholar 

  30. Rodman JE, Soltis PS, Soltis DE, Sytsma KJ and Karol KG (1998) Parallel evolution of glucosinolate biosynthesis inferred from congruent nuclear and plastid gene phylogenies. Amer J Bot 85: 997–1006

    Google Scholar 

  31. Rodman JE (1981) Divergence, convergence and parallelism in phytochemical characters: The glucosinolate-myrosinase system. In: Young DA and Seigler DS (eds) Phytochemistry and Angiosperm Phylogeny. New York: Praeger pp 43–79

    Google Scholar 

  32. Bak S, Nielsen HL and Halkier BA (1998) The presence of CYP9 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cynaogeni glycosides and glucosinolates. Plant Mol Biol 38: 725–734

    Google Scholar 

  33. Bones AM and Rossiter JT (1996) The myrosinaseglucosinolate system, its organisation and biochemistry. Physiol Plant 97: 194–208

    Google Scholar 

  34. Thangstad OP, Inversen T-H, Slupphaug G and Bones A (1990) Immunocytochemical localisation of myrosinase in Brassica napus L. Planta 180: 245–248

    Google Scholar 

  35. Thangsatd OP, Evjen K and Bones A (1991) Immunogold-EM localisation of myrosinase in Brassicaceae. Protoplasma 161:85–93

    Google Scholar 

  36. Grob K and Matile PH (1979) Vacuolar location of glucosinolates in horseradish cell roots. Plant Sci Lett 14: 327–335

    Google Scholar 

  37. Tookey HL (1973) Seperation of a protein required for epithiobutane formation. Can J Biochem 51: 1654–1660

    Google Scholar 

  38. Uda Y, Kurata T and Arakawa N (1986) Effects of pH and ferrous ions on the degradation of glucosinolates by myrosinase. Agric Biol Chem 50: 2735–2740

    Google Scholar 

  39. Griffiths DW, Birch ANE and Hillman JR (1998). Antinutrional compounds in the Brassicaceae: Analysis, biosynthesis, chemistry and dietary effects. J Hort Sci and Biotech 73: 1–18

    Google Scholar 

  40. Fenwick GR, Heany RK and Mullin WJ (1983) Glucosinolates and their breakdown products in food and food plants. Cri Rev Food Sci Nutr 18: 123–201

    Google Scholar 

  41. Verhoeven DTH, Verhagen H, Goldbohm RA, Van den Brandt PA and Van Poppel G (1997) A review of mechanisms underlying anticarcinogenicity by Brassica vegetables. Chem Biol Int 103: 79–129

    Google Scholar 

  42. Jongen WMF (1996) Glucosinolates in Brassica: Occurrence and significance as cancer modulating agents. Proc Nutri Soc 55: 433–446

    Google Scholar 

  43. Talalay P and Zhang Y (1996) Chemoprotection against cancer by isothiocyanates and glucosinolates. Biochem Soc Trans 24: 806–810

    Google Scholar 

  44. Zhang Y, Talalay P, Cho C-G and Posner GH (1992) A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure. Proc Natl Acad Sci USA 89: 2399–2403

    Google Scholar 

  45. Smith TK, Lund EK and Johnson IT (1998) Inhibition of dimethylhydrazine-induced aberrant crypt formation and inductin of apoptosis in rat colon following oraladministration of the glucosinolate sinigrin. Carcinogenesis 19: 267–273

    Google Scholar 

  46. Glen DM, Jones H and Fieldsend JK (1990) Damage to oilseed rape seedlings by the field slug Deroceras reticulatum in relation to glucosinolate concentration. Ann Appl Biol 117:197–207

    Google Scholar 

  47. Giamoustaris A and Mithen RF (1995). The effect of modifying the glucosinolate contentof leaves of oilseed rape (Brassica napus spp oleifera) on its interaction with specialist and generalist pests. Ann Appl Biol 126: 347–363

    Google Scholar 

  48. Chew FS (1988) Biological effects of glucosinolates. In: Cutler HG (ed) Biologically Active Natural Products Potential Use in Agriculture. Washington DC: Amercian Chemcal Society, pp 155–181

    Google Scholar 

  49. Louda S and Mole S (1991). Glucosinolates: Chemistry and ecology. In: Rosenthal GA and Berenbaum MR (eds) Herbivores:Their Interactions with Secondary Metabolites, 2nd edn. Academic Press, pp 124–164

  50. Stadler E (1978) Chemoreception of host plant chemicals by ovipoisting females of Delia (Hylemia) brassicae. Entol Exp Appl 24: 711–720

    Google Scholar 

  51. Mithen RF, Raybould A and Giamoustaris A (1995) Divergent selection for secondary metabolites between wild populations of Brassica oleracea and its implication for plant-herbivore interactions. Heredity 75: 472–484 103

    Google Scholar 

  52. Mithen RF, Lewis BG and Fenwick GR (1986) In vitro activity of glucosinolates and their products against Leptosphaeria maculans. Trans Brit Mycol Soc 87: 433–440

    Google Scholar 

  53. Giamoustaris A and Mithen RF (1997) Glucosinolates and disease resistance in oilseed rape (Brassica napus spp oleifera). Plant Path 46: 271–275

    Google Scholar 

  54. Kirkegaard JA, Gardner PA, Angus JF and Koetz E (1994) Effect of Brassica crops on the growth and yield of wheat. Aust J Agric Res 45: 529–545

    Google Scholar 

  55. Angus JF, Gardner PA, Kirkegaard JA and Desmarchelier JM (1994) Biofumigation: Isothiocyanates release from Brassica roots inhibit growth of the take-all fungus. Plant Soil 162:107–112

    Google Scholar 

  56. Toroser D, Thormann CE, Osborn TC and Mithen RF (1995) RFLP mapping of quantitative trait loci controlling seed aliphatic glucosinolate content in oilseed rape (Brassica napus). Thoer Appl Genet 91: 802–808

    Google Scholar 

  57. Uzunova M, Ecke W, Weissleder K and Röbbelen G (1995) Mapping the genome of rapeseed (Brassica napus L).I. Construction of an RFLP linkage map and localisation of QTLs for seed glucosinolate content. Theor Appl Genetc 90:194–204

    Google Scholar 

  58. Magrath R, Bano F, Morgner M, Parkin I, Sharpe A, Lister C, Dean C, Lydiate D and Mithen RF (1994). Genetics of aliphatic glucosinolates I. Side chain elongation in Brassica napus and Arabidopsis thaliana. Heredity 72: 290–199

    Google Scholar 

  59. Mithen RF, Clarke J, Lister C and Dean C (1995) Genetics of aliphatic glucosinolates III. Side chain modifications in Arabidopsis thaliana. Heredity 74: 210–215

    Google Scholar 

  60. Faulkner K, Mithen RF and Williamson G (1997) Selective increase of the potential anticarcinogen 4-methylsulphinylbutyl glucosinolate in broccoli. Carcinogenesis 19:605–609

    Google Scholar 

  61. Anon (1997) Plants with reduced glucosinolate content. International Patent application number WO 97/16559

  62. Chavadej S, Brisson N, McNeil JN and DeLuca V (1994) Redirection of tryptophan leads to the production of low indole glucosinolate canola. Proc Natl Acad Sci USA 91: 2166–2170

    Google Scholar 

  63. Lefebvre DD (1990) Expression of mammalian metallothionen suppresses glucosinolate synthesis in Brassica campestris. Plant Physiol 93: 522–524

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mithen, R. Glucosinolates – biochemistry, genetics and biological activity. Plant Growth Regulation 34, 91–103 (2001). https://doi.org/10.1023/A:1013330819778

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1013330819778

Navigation