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Canola and Rapeseed pp 149–172Cite as

Glucosinolates: Structure-Properties-Function

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Abstract

Glucosinolates are plant products with a side chain (R-group) and D-glucopyranose as β-thioglucoside attached to the carbon atom (No. 0) in Z(cis)-N-hydroximine sulfate esters (Figure 9-1; Olsen and Sørenson 1981). Structural variations among the more than 100 known glucosinolates are due mainly to various side chains that have more or less structural resemblance to the side chains of the biosynthetic amino acid precursors (Bjerg et al. 1987b; Eggum and Sorensen 1989). In addition, several glucosinolates have carboxylic acids attached as esters to the thioglucose part (Figure 9-1: R2and R6; Bjerg and Sørensen 1987a) or to glycosides forming parts of the R-group in some glucosinolates (see following).

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References

  • Benn, M. 1977. Glucosinolates, in “Low molecular weight sulphur-containing natural products,” ed., J. Wrobel. Pure and Appl. Chem. 49:197–210.

    Google Scholar 

  • Bille, N.; Eggum, B. O.; Jacobsen, I.; Olsen, O.; and Sorensen, H. 1983a. Antinutritional and toxic effects in rats of individual glucosinolates (± myrosinases) added to a standard diet (1). The effect on protein utilization and organ weights. Zeitschr. Tierphysiol., Tieremährung u. Futtermittelkd. 49: 195–210.

    Article  CAS  Google Scholar 

  • Bille, N.; Eggum, B. O.; Jacobsen, I.; Olsen, O.; and Sorensen, H. 1983b. The effects of processing on antinutritional rape constituents and the nutritive value of double-low rapeseed meal. Zeitschr. Thierphysiol., Tierernährung u. Futtermittelkd. 40: 148–163.

    Google Scholar 

  • Bjerg, B.; Eggum, B. O.; Jacobsen, I.; Larsen, L. M.; Rahman, M. H.; and Sorensen, H. 1986. Emmringsmmssig kvalitet af morkskallet, dobbeltlav vrraps (Topas) og af gulskallet raps i relation til glucosinolatindhold og procesbehandling. (Nutritive quality of dark-seeded, double-low spring rape [Topas] and of yellow-seeded rape in relation to glucosinolate content and processing effects.) Statens Husdyrbrugsforsog Medd. 634: 1–4.

    Google Scholar 

  • Bjerg, B.; Eggum, B. O.; Jacobsen, I.; Otte, J.; and Sorensen, H. 1989. Antinutritional and toxic effects in rats of individual glucosinolates (± myrosinases) added to a standard diet (2), Zeitschr. Tierphysiol., Tierernährung u. Futtermittelkd. 61: 227–244.

    CAS  Google Scholar 

  • Bjerg, B.; Eggum, B. O.; Rasmussen, K. W.; and Sorensen, H. 1987a. Acceptable concentrations of glucosinolates in double low oilseed rape and possibilities of further quality improvements by processing and plant breeding, in Proc. of 7th Inter. Rapeseed Congress, Poznan, Poland. 7: 1,619–1,626.

    Google Scholar 

  • Bjerg, B.; Kachlicki, P. W.; Larsen, L. M.; and Sorensen, H. 1987b. Metabolism of glucosinolates, in Proc of 7th Inter. Rapeseed Congress, Poznan, Poland. 2: 496–506.

    Google Scholar 

  • Bjerg, B.; Larsen, L. M.; and Sorensen, H. 1987c. Reliability of analytical methods for quantitative determination of individual glucosinolates and total glucosinolate content in double low oilseed rape, in Proc. of 7th Inter Rapeseed Congress, Poznan, Poland. 6: 1,330–1,341.

    Google Scholar 

  • Bjerg, B., and Sorensen, H. 1987a. Isolation of intact glucosinolates by column chromatography and determination of their purity, in World Crops: Production, Utilization, Description. Glucosinolates in Rapeseeds: Analytical Aspects, ed. J.-P. Wathelet. Dordrecht: Martinus Nijhoff. 13: 59–75.

    Chapter  Google Scholar 

  • Bjerg, B., and Sorensen, H. 1987b. Quantitative analysis of glucosinolates in oilseed rape based on HPLC of desulfoglucosinolates and HPLC of intact glucosinolates. Ibid. 13: 125–150.

    CAS  Google Scholar 

  • Björkqvist, B., and Hase, A. 1988. Separation and determination of intact glucosinolates in rapeseed by high-performance liquid chromatography. J. Chromatogr. 435: 501–507.

    Article  Google Scholar 

  • Buchwaldt, L.; Larsen, L. M.; Plöger, A.; and Sorensen, H. 1986. FPLC isolation and characterization of plant myrosinase, β-thioglucoside glucohydrolase, isoenzymes. J. Chromatogr. 363 (1): 71–80.

    Article  CAS  Google Scholar 

  • CEC expert group (Oct. 1987) B: J.-P. Whatelet; D: R. Buchner and W. Thies; DK: B. Bjerg and H. Sorensen, F: A. Quinsac and C. Ribaillier, GB: R. K. Heaney and E. A. Spinks; NL: B. G. Muuse. Rapeseed: Determination of the content of individual glucosinolates in rapeseed using HPLC. Report to CEC.

    Google Scholar 

  • Christensen, B. W.; Kjær, A.; Madsen, J.-O; Olsen, C. E.; Olsen, O.; and Sorensen, H. 1982. Mass spectrometric characteristics of some pertrimethylsilylated desulfoglucosinolates. Tetrahedron. 38: 353–357.

    Article  Google Scholar 

  • Cole, R. A. 1976. Isothiocyanates, nitriles, and thiocyanates as products of autolysis of glucosinolates in Cruciferae. Phytochemistry. 15: 759–762.

    Article  CAS  Google Scholar 

  • Dalgaard, L.; Nawaz, R.; and Sorensen, H. 1977. 3-Methylthiopropylamine and (R)-3methylsulphinylpropylamine in Iberis amara. Phytochemistry 16:931–932.

    Google Scholar 

  • Danielak, R., and Borkowski, B. 1970. New thioglucosides from seeds of dame’s violet (Hesperis matronalis L.). Dissert. Pharm. Pharmacol. XXII 2 /3: 143–148.

    Google Scholar 

  • Danielsen, V.; Eggum, B. O.; Rasmussen, K. W.; and Sorensen, H. 1987. Long-term studies of requirements to the quality of rapeseed meal from double-low varieties used in sow diets, in Proc. of 7th Inter. Rapeseed Congress, Poznan, Poland. 7:1, 727–1, 736.

    Google Scholar 

  • Daun, J. K., and McGregor, D. I. 1983. Glucosinolate analysis of rapeseed (canola). Method of the Canadian Grain Commission Grain Research Laboratory, Winnipeg. 1981 (revised 1983).

    Google Scholar 

  • Daun, J. K. 1986. Glucosinolate levels in western Canadian rapeseed and canola. J. Am. Oil Chem. Soc. 63 (5): 639–643.

    Article  CAS  Google Scholar 

  • Daxenbichler, M. E.; Van Etten, C. H.; and Williams, P. H. 1979. Glucosinolates and derived products in cruciferous vegetables: analysis of 14 varieties of Chinese cabbage. J. Agric. Food Chem. 27: 34–37.

    Article  CAS  Google Scholar 

  • Eggum, B. O., and Sorensen, H. 1989. Chemistry and analysis of amino acids, inAbsorption and Utilization of Amino Acids, vol. 3:17, ed. M. Friedman. Boca Raton, Florida: CRC Press.

    Google Scholar 

  • Elliott, M. C., and Stowe, B. B. 1970. A novel sulphonated natural indole. Phytochemistry 9: 1, 629.

    Google Scholar 

  • Ettlinger, M. G., and Kjer, A. 1968. Sulfur compounds in plants, in Recent Advances in Phytochemistry, eds. T. J. Mabry, R. E. Alston, and V. C. Runeckles. New York: Appleton-Century-Crofts. 1: 58–144.

    Google Scholar 

  • Fenwick, G. R.; Heaney, R. K.; and Mullen, W. J. 1983. Glucosinolates and their breakdown products in foods and food plants. CRC Crit. Rev. Fd. Sci. Nutr. 18: 123–201.

    Article  CAS  Google Scholar 

  • Helboe, P.; Olsen, O.; and Sorensen, H. 1980. Separation of glucosinolates by high performance liquid chromatography. J. Chromatogr. 197: 199–205.

    Article  CAS  Google Scholar 

  • Henriksen, P.; Hillemann, G.; Mortensen, K.; and Sorensen, H. 1987. Requirements to the quality of oilseed rape which can be used without problems in diets to mink (Mustela vison Screb), in Proc of 7th International Rapeseed Congress, Poznan, Poland. 7:1, 817–1, 824.

    Google Scholar 

  • Josefsson, E. 1967. Distribution of thioglucosides in different parts of Brassica plants. Phytochemistry 6: 1,617–1,627.

    Article  CAS  Google Scholar 

  • Kjær, A. 1960. Naturally derived isothiocyanates (mustard oil) and their parent glucosides, in Progress in the Chemistry of Organic Natural Products, eds. W. Hetz, H. Grisebach, and G. W. Kirby. Berlin/New York: Springer-Verlag. 122.

    Google Scholar 

  • Kjmr, A., and Larsen, P. O. 1980. Non-protein amino acids, cyanogenic glucosides, and glucosinolates, in Biosynthesis, Specialist Periodical Report. Chemical Society London 6: ibid.; 5 (1977):120–135; 4 (1976):179–203; 2 (1973): 71–105.

    Google Scholar 

  • Larsen, L. M., and Sorensen, H. 1985. The value of oilseed rape production in Denmark and the EEC, in Advances in the Production and Utilization of Cruciferous Crops, ed. H. Sorensen. Dordrecht: Martinus Nijhoff. 11: 1–18.

    Google Scholar 

  • MacLeod, A. J.; MacLeod, G.; and Reader, G. 1989. Evidence for the occurrence of butyl-and isobutylglucosinolates in seeds of Brassica oleraceae. Phytochemistry 28(5):1, 405–1, 407.

    Google Scholar 

  • Minchinton, I. R.; Sang, J. P.; Burke, D.; and Truscott, R. J. W. 1982. Separation of desulfoglucosinolates by reversed-phase high-performance liquid chromatography. J. Chromatogr. 247: 141–148.

    Article  CAS  Google Scholar 

  • Nielsen, J. K.; Dalgaard, L.; Larsen, L. M.; and Sorensen, H. 1979. Host-plant selection of the horseradish flea beetle Phyllotreta armoraciae (Koch); Coleoptera: Crysomelidaefeeding responses to glucosinolates from several crucifers. Ent. Exp. Appl. 25: 227–239.

    Article  Google Scholar 

  • Olsen, H. S. 1988. Aqueous enzymatic extraction of oil from seeds, in Proceedings of Asian Food Conference, October 24–26, 1988, Bangkok, Thailand.

    Google Scholar 

  • Olsen, O., and Sorensen, H. 1980a. Sinalbin and other glucosinolates in seeds of double-low rape species and Brassica nap us cv. Bronowski. J. Agric. Food Chem. 28: 43–48.

    Article  CAS  Google Scholar 

  • Olsen, O., and Sorensen, H. 1980b. Quantitative analysis of individual glucosinolates in a single or a few rapeseeds, in Analytical Chemistry of Rapeseed and Its Products, eds. J. K. Daun, D. I. McGregor, and E. E. McGregor. Canola Council of Canada, Winnipeg. 71–81.

    Google Scholar 

  • Olsen, O., and Sorensen, H. 1981. Recent advances in the analysis of glucosinolates. J. Am. Oil Chem. Soc. 58: 857–865.

    Article  CAS  Google Scholar 

  • Olsen, O., and Sorensen, H. 1983. Glucosinolate analysis: limitations and possibilities of different procedures. Proc. of 6th International Rapeseed Congress, Paris. Tome II, 1356–1361.

    Google Scholar 

  • Palmieri, S.; Iori, R.; and Leoni, O. 1986. Myrosinase from Sinapis alba L.: a new method of purification for glucosinolate analyses. J. Agric. Food. Chem. 34: 138–140.

    Article  CAS  Google Scholar 

  • Rodman, J. E. 1978. Phytochemical Bulletin, Phytochemical Section. Botanical Society of America. 11(1,2):6–31.

    Google Scholar 

  • Sang, J. P.; Minchinton, I. R.; Johnstone, P. K.; and Truscott, R. J. W. 1984. Glucosinolate profiles in the seed, root, and leaf tissue of cabbage, mustard, radish, and swede. Can. J. Plant. Sci. 64: 77–93.

    Article  CAS  Google Scholar 

  • Sorensen, H. 1985. Advances in the Production and Utilization of Cruciferous Crops. Dordrecht: Martinus Nijhoff. 11:317 pp.

    Google Scholar 

  • Sorensen, H. 1985. Limitations and possibilities of different methods suitable to quantitative analysis of glucosinolates occurring in double low rapeseed and products thereof, in Advances in the Production and Utilization of Cruciferous Crops, ed. H. Sorensen. Dordrecht: Martinus Nijhoff. 11: 73–84.

    Google Scholar 

  • Sorensen, H. 1988. Analysis of glucosinolates and acceptable concentrations of glucosinolates in oilseed rape and products thereof used as feed to different animals. Groupe Consultatif International De Recherche sur le Colza, GCIRC: Bulletin 4: 17–19.

    Google Scholar 

  • Thies, W. 1976. Quantitative gas liquid chromatography of glucosinolates in a microliter scale. Fette, Seifen, Anstrichm. 78: 231–234.

    Article  CAS  Google Scholar 

  • Thies, W. 1980. Analytical Chemistry of Rapeseed and Its Products, eds. J. K. Daun, D. I. McGregor, and E. E. McGregor. Canola Council of Canada, Winnipeg. 66–71.

    Google Scholar 

  • Underhill, E. W., and Kirkland, D. F. 1971. Gas chromatography of trimethylsilylderivatives of glucosinolates. J. Chromatogr. 57: 47–54.

    Article  CAS  Google Scholar 

  • Underhill, E. W., and Kirkland, D. F. 1980. Glucosinolates, in Secondary Plant Products: Encyclopedia of Plant Physiology, new series, eds. E. A. Bell and B. V. Charlwood. Berlin: Springer-Verlag. 8: 493–511.

    Chapter  Google Scholar 

  • Van Etten, C. H., and Tookey, H. L. 1979. Chemistry and biological effects of glucosinolates, in Herbivores: Their Interaction with Secondary Plant Metabolites, eds. G. A. Rosenthal and P. H. Jansen. Academic Press. 13: 471–500.

    Google Scholar 

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Authors
  1. Hilmer Sørensen
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Editors and Affiliations

  1. Food Science Program, Department of Biochemistry, Memorial University of Newfoundland, St. John’s, Newfoundland, Canada

    Fereidoon Shahidi

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Sørensen, H. (1990). Glucosinolates: Structure-Properties-Function. In: Shahidi, F. (eds) Canola and Rapeseed. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3912-4_9

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  • DOI: https://doi.org/10.1007/978-1-4615-3912-4_9

  • Publisher Name: Springer, Boston, MA

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