Antinutritional compounds in the Brassicaceae: Analysis, biosynthesis, chemistry and dietary effects

Journal of Horticultural Science and Biotechnology

Volumn 73, Issue 1, 1998, Pages 1-18

  Griffiths, D W ^a   Birch, A N E ^a   Hillman, J R ^a  

^a SCOTTISH CROP RESEARCH INSTITUTE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSAFETY; BIOSYNTHESIS; CHEMICAL ANALYSIS; ERUCIC ACID; GLUCOSINOLATE; METHYLCYSTEINE SULFOXIDE; SECONDARY METABOLITE; TANNIN;

ANIMALIA; BRASSICACEAE;

EID: 0031981244     PISSN: 14620316     EISSN: None     Source Type: Journal    
DOI: 10.1080/14620316.1998.11510937     Document Type: Review

References (143)

1. AHLIN, K. A., EMANUELSON, M. and WIKTORRSON, H. (1994). Rapeseed products from double-low cultivars as feed for dairy cows: effects of long term feeding on thyroid function, fertility and animal health. Acta Veterinaria Scandinavica, 35, 37-53.
2. AMES, B. N., PROFET, M. and GOLD, L. S. (1990a). Dietary pesticides (99.99% all natural). Proceedings of the National Academy of Science, 87, 7777-81.
3. AMES, B. N., PROFET, M. and GOLD, L. S. (1990b). Nature's chemicals and synthetic chemicals: Comparative toxicology. Proceedings of the National Academy of Science 87, 7782-6.
4. APPELQVIST, L. A. (1976). Lipids in the cruciferae. In: The biology and chemistry of the Cruciferae. (Vaughan, J. G., Macleod, A. J. and Jones, B. M. O., Eds). Academic Press, New York, 307-40.
5. ARNOLD, W. N. and THOMPSON, J. F. (1962). The formation of (+) S-methyl-L-cysteine sulfoxide from S-methyl-L-cysteine in crucifers. Biochimica et Biophys Acta, 57, 604-6.
6. BATE-SMITH, E. C. and RIBERAU-GAYON, P. (1959). Leucoanthocyanins in seeds. Qualitas Plantarum et Materiae Vegetabiles, 5, 189-98.
7. BELL, J. M. (1993). Factors affecting the nutritional value of canola meal: A review. Canadian Journal of Animal Science, 73, 679-97.
8. BELL, J. M. (1995). Meal and by-product utilization in animal nutrition. In: Brassica oilseeds, production and utilization. (Kimber, D. S. and McGregor, D. I., Eds). CAB International, Wallingford, UK, 301-37.
9. BELL, J. M. and SHIRES, A. (1982). Composition and digestibility by pigs of hull fractions from oilseed cultivars with yellow or brown seed coats. Canadian Journal of Animal Science, 62, 557-65.
10. BENNETT, R., DONALD, A., DAWSON, G., HICK, A. and WALLSGROVE, R. (1993). Aldoxime-forming microsomal enzymes systems involved in the biosynthesis of glucosinolates in oilseed rape (Brassica napus) leaves. Plant Physiology, 102, 1307-12.
11. BENNETT, R. N., HICK, A. J., DAWSON, G. W. and WALLSGROVE, R. M. (1995a). Glucosinolate biosynthesis. Further characterization of the aldoxime-forming microsomal monooxygenases in oilseed rape leaves. Plant Physiology, 109, 299-305.
12. BENNETT, R., LUDWIG-MULLER, J., KIDDLE, G., HILGENBERG, W. and WALLSGROVE, R. M. (1995b). Developmental regulation of aldoxime formation in seedlings and mature plants of Chinese cabbage (Brassica campestris spp pekinensis) and oilseed rape (Brassica napus): Glucosinolate and IAA biosynthetic enzymes. Planta, 196, 239-44.
13. BENNETT, R. N., KIDDLE, G., HICK, A. J., DAWSON, G. W. and WALLSGROVE, R. M. (1996). Distribution and activity of microsomal NADPH-dependant monooxygenases and amino acid decarboxylases in cruciferous and non-cruciferous plants, and their relationship to foliar glucosinolate content. Plant, Cell and Environment, 19, 801-12.
14. BENNETT, R. N., KIDDLE, G. and WALLSGROVE, R. M. (1997). Biosynthesis of benzyl glucosinolate, cyanogenic glucosides, and phenylpropanoids in Carica papaya. Phytochemistry, 45, 59-66.
15. BJERG, B. and SØRENSEN, H. (1987). Isolation of intact glucosinolates by column chromatography and determination of their purity. In: World crops: Production, utilization description, glucosinolates in rapeseeds: Analytical aspects. (Wathelet, J-P., Ed.). Martinus Nijhoff, Dordrecht, The Netherlands, 59-75.
16. BLIGHT, M. M., HICK, A. J., PICKETT, J. A., SMART, L. E., WADHAMS, L. J. and WOODCOCK, C. M. (1992). Volatile plant metabolites involved in host-plant recognition by the cabbage seed weevil, Ceutrorhyncus assimilis. Proceedings of the 8th International Symposium on Insect Plant Relationships. (Menkin, S. B. J., Visser, J. H. and Harrewijn, P., Eds). Kluwer Academic Publishers, Dordrecht, The Netherlands, 105-6.
17. BOLTON, W., CARTER, T. C. and MORLEY, J. R. (1976). The hen's egg: genetics of taints in eggs from hens fed on rapeseed meal. British Poultry Science, 17, 313-20.
18. BOURDON, D., PEREZ, J. M. and BAUDET, J. J. (1985). Nutritive value and utilization by the growing-finishing pigs of new types of rapeseed oil meals with low glucosinolate content. In: Advances in the production and utilization of cruciferous crops. (Sørensen, H., Ed.). Martinas Nijhoff/Dr W. Junk Publishers, Dordrecht, The Netherlands, 177-98.
19. BUTCHER, R. D., MACFARLANE SMITH, W. H., ROBERTSON, G. W. and GRIFFITHS, D.W. (1994). The identification of potential aeroallergen/irritant(s) from oilseed rape (Brassica napus spp oleifera): volatile organic compounds emmitted during flowering progression. Clinical and Experimental Allergy, 24, 1105-14.
20. BUTLER, L. G. (1989). Effects of condensed tannins on animal nutrition. In: Chemistry and significance of condensed tannins. (Hemingway, R. W. and Karchesy, J. J., Eds). Plenum Press, New York, 391-402.
21. BUTLER, L. G. and BOS, K. D. (1993). Analysis and characterization of tannins in faba beans, cereals and other seeds. A literature review. In: Recent advances of research in antinutritional factors in legume seeds. (Van der Poel, A. F. B., Huisman, J. and Saini, H. S., Eds). Wageningen Pers, Wageningen, The Netherlands, 91-100.
22. CHAPPLE, C. C. S., GLOVER, J. R. and ELLIS, B. E. (1990). Purification and characterization of methionine: glyoxylate aminotransferase from Brassica carinata and Brassica napus. Plant Physiology, 94, 1887-96.
23. CHRISTIE, W. W. (1989) Gas chromatography and lipids, The Oily Press, Ayr, Scotland.
24. COWE, I. A. and CUTHBERTSON, D. C. (1985). Applications of NIR analysis. Annual Report of the Scottish Crop Research Institute for 1985, 140-1.
25. CREACH, A., LESSIRE, R. and CASSAGNE, C. (1993). Kinetics of C18-1 CoA elongation and transacylation in rapeseeds. Plant Physiology and Biochemistry, 31, 923-30.
26. DAUN, J. K. (1995). Seed Analysis. In: Brassica oilseeds, production and utilization. (Kimber, D. S. and McGregor, D. I., Eds). CAB International, Wallingford, UK, 243-65.
27. DAUN, J. K., CLEAR, K. M. and WILLIAMS, P. C. (1994). Comparison of three whole seed near infrared analysers for measuring quality components of canola seed. Journal of the American Oil Chemists' Society, 71, 1063-8.
28. D'MELLO, J. P. F. (1991). Toxic amino acids. In: Toxic Substances in crop plants (D'Mello, J. P. F., Duffus, C. M. and Duffus, J. H., Eds). Royal Society of Chemistry, Cambridge, UK, 108-25.
29. DU, L. and HALKIER, B. A. (1996). Isolation of a microsomal enzyme system involved in glucosinolate biosynthesis from seedlings of Tropaeolum major L. Plant Physiology, 111, 831-7.
30. DU, L., LYKKESFELDT, J., OLSEN, C. E. and HALKIER, B. A. (1995). 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. Proceedings of the National Academy of Science, 92, 12505-9.
31. DUNCAN, A. J. (1991). Glucosinolates. In: Toxic substances in crop plants. (D'Mello, J. P. F., Duffus, C. M. and Duffus, J. H., Eds), Royal Society of Chemistry, 126-47.
32. DURKEE, A. B. (1971). The nature of tannin in rapeseed (Brassica campestris). Phytochemistry, 10, 1583-5.
33. EDWARDS, S. J., MUSKER, D., COLIN, H. A. and BROTTON, G. (1994). The analysis of S-alk(en)yl-L-cysteine sulphoxides (flavour precursors) from species of Allium by high performance liquid chromatography. Phytochemical Analysis, 5, 4-9.
34. EGGUM, B. O. (1981). Nutritional problems related to double low rapeseed in animal nutrition. In: Production and utilization of protein in oilseed crops. (Bunting, E. S., Ed.). Martinus Nijhoff Publishers, The Hague, The Netherlands, 293-303.
35. EGGUM, B. O., OLE, O. and SØRENSEN, H. (1985). Effects of glucosinolates on the nutritive value of rapeseed. In: Advances in the production and utilization of cruciferous crops. (Sørensen, H., Ed.), Martinus Nijhoff/Dr W. Junk, Publishers, Dordrecht, The Netherlands, 50-60.
36. ETTLINGER, M. G. and LUNDEEN, A. J. (1956). The structure of sinigrin and sinalbin: an enzymatic rearrangement. Journal of the American Oil Chemists' Society, 78, 4172-3.
37. EVANS, E. J., BILSBORROW, P., GRANT, A., KWIATOWSKA, C. A., SPINKS, E. A., HEANEY, R. K. and FENWICK, G.R. (1989). A comparison of rapid- (X-ray fluorescence, near infrared reflectance) and glucose-release methods for the determination of the glucosinolate content of oilseed rape (Brassica oleracea). Journal of the Science of Food and Agriculture, 49, 297-305.
38. EVANS, K. A. and ALLEN-WILLIAMS, L. J. (1992). Electroantennogram responses of the cabbage seed weevil, Ceutrorhyncus assimilis, to oilseed rape, Brassica napus spp. oleifera volatiles. Journal of Chemical Ecology, 18, 1641-59.
39. FENWICK, G. R., HEANEY, R. K. and MULLIN, W. J. (1983). Glucosinolates and their breakdown products in food and food plants. CRC Critical Reviews in Food Science and Nutrition, 18, 123-201.
40. FENWICK, G. R., GRIFFITHS, N. M. and HEANEY, R. K. (1983a). Bitterness in Brussels sprouts (Brassica oleracea L. var. gemmifera): The role of glucosinolates and their breakdown products. Journal of the Science of Food and Agriculture, 34, 73-80.
41. FENWICK, G. R., HEANEY, R. K. and MAWSON, R. (1989). Glucosinolates. In: Toxicants of plant origin. Vol II. Glycosides. (Cheeke, R. R., Ed.), CRC Press, Boca Raton, Florida. USA, 1-41.
42. FOWLER, V. R., PUSZTAI, A., MCWILLIAM, R. and FRANK, R. (1987). The use of simple methods of extracting the antinutritive factors in rapeseed meal to improve the growth of pigs and rats. Animal Production, 44, 463.
43. FUJIWARA, M., ITOKAWA, Y., UCHINO, H. and INQUE, K. (1972). Anti-hypocholesterolemic effect of a sulfur containing amino acid, S-methylcysteine sulphoxide, isolated from cabbage. Experimentia, 28, 254-5.
44. GLENDENING, T. M. and POULTON, J. E. (1988). Sulfation of desulfobenzyl glucosinolate by cell free extracts of cress (Lepidum sativum L). Plant Physiology, 86, 319-21.
45. GLOVER, I. R., CHAPPLE, C. C., ROTHWELL, S., TOBER, I. and ELLIS, B. E. (1988). Allylglucosinolate biosynthesis in Brassica carinata. Phytochemistry, 27, 1345-8.
46. GOSDEN, A. F. (1978). An automated procedure for the estimation of thiocyanate in forage kale. Journal of the Science of Food and Agriculture, 29, 597-600.
47. GOSDEN, A. F. (1979). An automated procedure for the estimation of S methylcysteine sulphoxide in kale. Journal of the Science of Food and Agriculture, 30, 892-8.
48. GRIFFITHS, D. W. (1981). The polyphenolic content and enzyme inhibiting activity of testas from bean (Vicia faba) and pea (Pisum spp.) varieties. Journal of the Science of Food and Agriculture, 32, 797-804.
49. GRIFFITHS, D. W. (1984). Development and use of screening tests for important compounds in brassica breeding material. Annual Report of the Scottish Crop Research Institute for 1984, 170.
50. GRIFFITHS, D. W. (1989). Polyphenolics and their possible effect on nutritive value: In Anti-nutritional factors, potentially toxic substances in plants. Aspects of Applied Biology, 19, 93-102.
51. GRIFFITHS, D. W. (1991). Condensed tannins. In: Toxic substances in crop plants. (D'Mello, J. P. F., Duffus, C. M. and Duffus, J. H., Eds). The Royal Society of Chemistry, Cambridge, UK, 180-201.
52. GRIFFITHS, D. W. and MOSELEY, G. (1980). The effects of diets containing field beans of high and low polyphenolic content on the activity of digestive enzymes in the intestines of rats. Journal of the Science of Food and Agriculture, 31, 255-9.
53. GUO, L. and POULTON, J. E. (1994). Partial purification and characterization of Aradopsis thaliana UDPG: thiohydroximate glucosyltransferase. Phytochemistry, 36, 1133-8.
54. GURR, M. I. and HARWOOD, J. L. (1991). Lipid biochemistry, 4th Edition. Chapman and Hall, London, 379-82.
55. HARBORNE, J. B. (1988). Introduction to ecological biochemistry, 3rd Edition. Academic Press, New York.
56. HASLAM, E. (1989a). Condensed proanthocyanidins. In: Plant polyphenols and vegetable tannins revisited. (Haslam, E., Ed.). Cambridge University Press, Cambridge, 14-89.
57. HASLAM, E. (1989b). Polyphenol complexation. In: Plant polyphenols and vegetable tannins revisited. (Haslam, E., Ed.). Cambridge University Press, Cambridge, 154-219.
58. HEANEY, R. K. and FENWICK, G. R. (1980). The analysis of glucosinolates in Brassica species using gas chromatography, direct determination of the thiocyanale ion precursors, glucobrassicin and neoglucobrassicin. Journal of the Science of Food and Agriculture, 31, 593-9.
59. HEANEY, R. K. and FENWICK, G. R. (1981). A micro-column method for the rapid determination of total glucosinolate content of cuciferous material. Zeitschrift fur Pflanzenzuchtung, 87, 89-95.
60. HEANEY, R. K. and FENWICK, G. R. (1995). Natural toxins and protective factors in brassica species, including rapeseed. Natural Toxins, 3, 233-7.
61. HOGGE, L. R., REED, D. W., UNDERHILL, E. W. and HAUGHN, G. W. (1988). HPLC separation of glucosinolates from leaves and seeds of Arabidopsis thaliana and their identification by themospray liquid chromatography/mass spectrometry. Journal of Chromatographic Science. 26, 551-6.
62. JAIN, J. C., GROOTWASSINK, J. W. D., KOLENOVSKY, A. D. and UNDERHILL, E. W. (1990). Purification and properties of 3′-phosphoadenosine-5′-phosphosulphate: desulphoglucosinolate sulphotransferase from Brassica juncea cell cultures. Phytochemistry, 29, 1425-8.
63. JAKOBSEN, H. B., FRIIS, P., NEILSEN, J. K. and OLSEN, C. E. (1994). Emission of volatiles from flowers and leaves of Brassica napus in situ. Phytochemistry, 37, 695-9.
64. KJAER, A. (1976). Glucosinolates in the cruciferae. In: The biology and chemistry of the cruciferae. (Vaughan, J. G., Macleod, A. J. and Jones, B. M. G., Eds). Academic Press, New York, 207-19.
65. LANGER, R. H. M. and HILL, G. D. (1982). Cruciferae. In: Agricultural plants. (Langer, R. H. M. and Hill, G. D., Eds). Cambridge University Press, Cambridge, 165-83.
66. LARSEN, L. M., OLSEN, O. and PLOGER, A. (1983). Phenolic choline esters in rapeseed: possible factors affecting nutritive value and quality of rapeseed meal. Proceedings of 6th International Rapeseed Conference, 2, 1577-82.
67. LARYEA, M. D., JIANG, Y. F., XU, G. L. and LOMBECK, I. (1992). Fatty acid composition of blood lipids in Chinese children consuming high erucic acid rapeseed oil. Annals of Nutrition and Metabolism, 36, 273-8.
68. LILA, M. and FURSTOSS, V. (1986). Determination de longeurs d'onde specifiques pour la mesure des glucosinolates du colza par spectrophotometrie de reflexion dans la proche infrarouge. Agronomie 6, 703-7.
69. LOUDA, S. and MOLE, S. (1991). Glucosinolates: chemistry and ecology. In: Herbivores, their interactions with secondary plant metabolites. Vol. 1 The chemical participants. (Rosenthal, G. A. and Berenbaum, M. R., Eds). Academic Press, New York, 123-64.
70. MACFARLANE-SMITH, W. H. and GRIFFITHS, D. W. (1988). A time course study of glucosinolates in the ontogeny of forage rape (Brassica napus L). Journal of the Science of Food and Agriculture, 43, 121-34.
71. MACLEOD, A. J. (1976). Volatile flavour compounds of the cruciferae. In: The biology and chemistry of the Cruciferae. (Vaughan, J. G., Macleod, A. J. and Jones, B. M. G., Eds). Academic Press, New York, 307-40.
72. MAGRATH, R., HERRON, C., GIAMOUSTARIS, A. and MITHEN, R. (1993). The inheritance of aliphatic glucosinolates in Brassica napus. Plant Breeding, 111, 55-72.
73. MAKKAR, H. P. S., SINGH, B. and DAWRA, R. K. (1987). Tannin-nutrient interactions-A review. International Journal of Animal Science, 2, 127-40.
74. MARKS, H. S., HILSON, J. A., LEICHTWEISS, H. C. and STOEWSAND, G. S. (1992). S-methylcysteine sulphoxide in Brassica vegetables and formation of methyl methanethioslfinate from Brussels sprouts. Journal of Agricultural and Food Chemistry, 40, 2098-101.
75. MARQUARDT, R. R. (1989). Dietary effects of tannins, vicine and convicine. In: Recent advances of research in antinutritional factors in legume seeds. (Huisman, J., van der Poel, T. F. B. and Liener, I. E., Eds). Pudoc Press, Wageningen, The Netherlands, 141-55.
76. MAW, G. A. (1982). Biochemistry of S-methylcysteine and its principal derivatives. Sulfur Reports, 2, 1-32.
77. MAWSON, R., HEANEY, R. K., ZDUNCZYK, Z. and LOZLOWSKA, H. (1993). Rapeseed meal-glucosinolates and their anti-nutritional effects. Part II. Flavour and palatability. Die Nahrung, 37, 336-44.
78. MAWSON, R., HEANEY, R. K., ZDUNCZYK, Z. and LOZLOWSKA, H. (1994a). Rapeseed meal-glucosinolates and their anti-nutritional effects. Part 3. Animal growth and performance. Die Nahrung, 38, 167-77.
79. MAWSON, R., HEANEY, R. K., ZDUNCZYK, Z. and LOZLOWSKA, H. (1994b). Rapeseed meal-glucosinolates and their anti-nutritional effects. Part 4. Goitrogenicity and internal organs abnormalities in animals. Die Nahrung, 38, 178-91.
80. MAWSON, R., HEANEY, R. K., ZDUNCZYK, Z. and LOZLOWSKA, H. (1994c). Rapeseed meal-glucosinolates and their anti-nutritional effects. Part 5. Animal production. Die Nahrung, 38, 588-98.
81. MCDANELL, R., MCLEAN, A. E. M., HANLEY, A. B., HEANEY, R. K. and FENWICK, G. R. (1988). Chemical and biological properties of indole glucosinolates (Glucobrassicins): A Review. Food and Chemical Toxicology, 26, 59-70.
82. MCGREGOR, D. I. (1985). Determination of glucosinolates in brassica seed. Eucarpia Cruciferae Newsletter, 10, 132-6.
83. MCLEOD, M. N. (1974). Plant tannins - their role in forage quality. Nutrition Abstracts and Reviews, 44, 803-15.
84. MEHANSHO, H., BUTLER, L. and CARLSON, D. M. (1987). Dietary tannins and salivary-rich proteins: Their interactions, induction and defense mechanism. Annual Reviews in Nutrition, 1987, 423-40.
85. MEHANSHO, H., HAGERMAN, A., CLEMENTS, S., BUTLER, L., ROGLER, J. and CARLSON, D. M. (1983). Modulation of proline-rich protein biosynthesis in rat parotid glands by sorghums with high tannin levels. Proceedings of the National Academy of Science, 80, 3948-52.
86. MICHAELSON, S., MØLLER, P. and SØRENSEN, H. (1992). Factors influencing the separation and quantitation of intact and desulphoglucosinolates by micellar electrokinetic capillary chromatography. Journal of Chromatography, 608, 363-74.
87. MINCHINTON, I., SANG, J., BURKE, D. and TRUSCOTT, R. J. W. (1982). Separation of desulphoglucosinolates by reversed-phase high performance liquid chromatography. Journal of Chromatography, 247, 141-8.
88. MITARU, B. N., BLAIR, R. B., BELL, J. M. and REICHERT, R. D. (1982). Tannin and fiber contents of rapeseed and canola hulls. Canadian Journal of Animal Science, 62, 661-3.
89. MITHEN, R. F., LEWIS, B. G., HEANEY, R. K. and FENWICK, G. R. (1987). Glucosinolates of wild and cultivated Brassica species. Phytochemistry, 26, 1969-73.
90. MØLLER, P., OLSEN, O., PLOGER, A., RASMUSSEN, K. W. and SØRENSEN, H. (1985a). Quantitative analysis of individual glucosinolates in double low oilseed rape by HPLC of intact glucosinolates. In: Advances in the production and utilization of cruciferous crops. (Sørensen, H., Ed.). Martinus Nijhoff, Dordrecht, The Netherlands, 111-26.
91. MØLLER, P., PLOGER, A. and SØRENSEN, H. (1985b). Quantitative analysis of total glucosinolates content in concentrated extracts from double low rapeseed by the Pd-glucosinolate complex method. In: Advances in the production and utilization of cruciferous crops. (Sørensen, H., Ed.). Martinus Nijoff, Dordrecht, The Netherlands, 97-110.
92. MORRIS, C. J. and THOMPSON, J. F. (1956). The identification of (+)S-methylcystein sulphoxide in plants. Journal of the American Chemical Society, 78, 1605-8.
93. MUELLER, M. M., RYL, E. B., FENTON, T. and CLANDININ, D. R. (1978a). Cultivar and growing location differences on the sinapine content of rapeseed. Canadian Journal of Animal Science, 58, 579-83.
94. MUELLER, M. M., COLEMAN, R. N. and CLANDININ, D. R. (1987b). Trimethylamine production from sinapine by enteric bacteria from laying hens. Proceedings of 5th International Rapeseed Conference, Malmo, 2, 303-6.
95. NACZK, M., NICOLS, T., PINK, D. and SOSULSKI, F. (1994). Condensed tannins in canola hulls. Journal of Agricultural and Food Chemistry, 42, 2196-200.
96. PEARSON, A. W., BUTLER, E. J., CURTIS, R. F., FENWICK, G. R., HOBSONFROHOCK, A. and LAND, D. G. (1979). Effect of rapeseed meal on trimethylamine oxidase activity in the domestic fowl in relation to egg taint. Journal of the Science of Food and Agriculture, 30, 291-8.
97. PETROSKI, R. J. and TOOKEY, R. L. (1982). Interaction of thioglucoside glucohydrolase and epithiospecifier protein of cruciferous plants to form 1-cyanoepithioalkanes. Phytochemistry, 21, 1903-7.
98. 6+). Journal of the Science of Food and Agriculture, 61, 79-86.
99. PORTER, L. J., HRSTICH, L. N. and CHAN, B. G. (1986). The conversion of procyanidins and prodelphinidins to cyanidin and delphinidin. Phytochemistry, 25, 223-30.
100. PRESTERA, T., FAHEY, J. W., HOLTZCLAW, W., ABEYGUNAWARDANA, C., KACHINSKI, J. L. and TALALAY, P. (1996). Comprehensive chromatographic and spectroscopic methods for the separation and identification of intact glucosinolates. Analytical Biochemistry, 239, 168-79.
101. PUSZTAI, A. (1989). Antinutrients in rapeseeds. Nutrition Abstracts and Reviews (Series B), 59, 427-33.
102. RADHAKRISHNAN, M. R. and SIVAPRASAD, J. (1980). Tannin content of sorghum varieties and their role in iron bioavailability. Journal of Agricultural and Food Chemistry, 28, 55-7.
103. REED, D. W., DAVIN, L., JAIN, J. C., DELUCA, V., NELSON, L. and UNDERHILL, E. W. (1993). Purification and properties of UDP-glucose: thiohydroximate glucosyltransferase from Brassica napus seedlings. Archives of Biochemistry and Biophysics, 305, 526-32.
104. ROBERTSON, G. W., GRIFFITHS, D. W., MACFARLANE-SMITH, W. H. and BUTCHER, R. D. (1993). The application of thermal desorption-gas chromatography-mass spectrometry to the analyses of flower volatiles from five varieties of oilseed rape (Brassica napus spp oleifera). Phytochemical Analysis, 4, 152-7.
105. ROSSITER, J. T., JAMES, D. C. and ATKINS, N. (1990). Biosynthesis of 2-hydroxy-3-butenylglucosinolate and 3-butenylgiucosinolate in Brassica napus. Phytochemistry, 29, 2509-12.
106. 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 rapeseed, radish and swede. Canadian Journal of Plant Science, 64, 77-93.
107. SAUPE, S. G. (1981). Cyanogenic compounds and angiosperm phylogeny. In: Phytochemistry and angiosperm phylogeny. (Young, D. A. and Seigler, D. S., Eds), Praeger Press, New York, 80-116.
108. SCHONE, F., STEINBACH, G., KIRCHNER, E., HENNIG, A. and LUDKE, H. (1987). Influence of diets with rapeseedmeal containing varying amounts of goitrogenic compounds or iodine on performance, immune response and some blood serum parameters in growing pigs. Acta Veterinaria Brno, 56, 292-301.
109. SCHNUG, E. and HANEKLAUS, S. (1987a). Indirect determination of total glucosinolate content in rapeseed by X-ray fluorescence. Fresenius Zeiischrift für Analytische Chemie, 326, 441-5.
110. SCHNUG, E. and HANEKLAUS. S. (1987b). Rapid and precise determination of total glucosinolate content in rapeseed: comparison of X-ray fluorescence spectrometry with gas chromatography and high performance liquid chromatography. Fett Wissenschaft Technologie, 89, 32-6.
111. SCHNUG, E. and HANEKLAUS, S. (1988). Theoretical principles for the indirect determination of the total glucosinolate content in oilseed rape and meal quantifying the sulphur concentration via X-ray fluorescence (X-RF method). Journal of the Science of Food and Agriculture, 45, 243-54.
112. SHAHIDI, F. and NACZK, M. (1995). Phenolic compounds of major oilseeds. In: Food phenolics, sources, chemistry, effects applications. (Shahidi, F. and Naczk, M., Eds). Technomic Publishing Co. Inc., Lancaster, PA, USA, 53-73.
113. SMITH, R. H. (1974). Kale poisoning. Annual Report of the Rowett Research Institute for 1974, 112-31.
114. SMITH, T. K. and CAMPBELL, L. D. (1976). Rapeseed meal glucosinolates: metabolism and effect on performance in laying hens. Poultry Science, 55, 861-7.
115. SPENCER, K. C. and SIEGLER, D. S. (1984). Cyanogenic glycosides of Carica papaya and its phylogenetic position with respect to the Violales and Capparales. American Journal of Botany, 97, 1444-7.
116. SPINKS, E. A., SONES, K. and FENWICK, G. R. (1984). The quantitative analysis of glucosinolates in cruciferous vegetables, oilseeds and forage crops using high performance liquid chromatography. Fette Seifen Anstrichmittel, 6, 228-31.
117. SPRINGETT, M. B. and ADAMS, J. B. (1988). Identification of 1-cyano-2,3-epithiopropane in volatiles of a model system from Brussels sprouts (Brassica oleraceae L. var bullata subvar gemmifera DC). Journal of the Science of Food and Agriculture, 46, 211-9.
118. SØRENSEN, H. (1990). Glucosinolates: structure-properties-function. In: Canola and rapeseed, production, chemistry, nutrition and processing technology (Shahidi, F., Ed.). Van Nostrand Reinhold, New York, 149-72.
119. STARR, C., SUTTLE, J., MORGAN, A. and SMITH, D. (1985). A comparison of sample preparation and calibration techniques for the estimation of nitrogen, oil and glucosinolate content of rapeseed by near infrared spectroscopy. Journal of Agriculture, Cambridge, 104, 314-23.
120. STONER, G. S., GALATAI, A. J., SCHMIDT, C. J. and MORSE, M. A. (1994). Inhibition of oesophageal tumorogenesis by phenylethyl isothiocyanate. In: Food phytochemicals for cancer prevention I. Fruits and vegetables. (Huang, M. T., Osawa, T., Ho, C. T. and Rosen, R. T., Eds). American Chemical Society, Washington, 173-80.
121. TALJAARD, T. L. (1993). Cabbage poisoning in ruminants. Journal of the South African Veterinary Association, 64, 96-100.
122. TAMIR, M. and ALUMOT, E. (1969). Inhibition of digestive enzymes by condensed tannins from green and ripe carobs. Journal of the Science of Food and Agriculture, 20, 199-202.
123. THIES, W. (1979). Detection and utilisation of a glucosinolate sulphohydrolase in the edible snail, Helix pomatia. Die Naturwissenschaften, 66, 364-5.
124. THIES, W. (1982). Complex-formation between glucosinolates and tetrachloropalladate (II) and its utilization in plant breeding. Fette Seifen Anstrichmittel, 9, 338-42.
125. THOLEN, J. T., SHIFENG, S. and TRUSCOTT, R. J. W. (1989). The thymol method for glucosinolate determination. Journal of the Science of Food and Agriculture, 49, 157-65.
126. THOMPSON, J. F. and GERING, R. K. (1966). Biosynthesis of S-methyllcysteine sulfoxide in radish leaves. Plant Physiology, 41, 1301-7.
127. THOMPSON, J. F. and MOORE, D. P. (1968). Enzymatic synthesis of cysteine and S-methylcysyeine in plant extracts. Biochemical and Biophysical Research Communications, 31, 281-6.
128. TKACHUK, R. (1981). Oil and protein analysis of whole rapeseed kernals by near infrared reflectance spectroscopy. Journal of the American Oil Chemists' Society, 58, 819-22.
129. TOLLSTEN, L. and BERGSTROM, G. (1988). Headspace volatiles of whole plants and macerated plant parts of Brassica and Sinapis. Phytochemistry, 27, 4013-8.
130. UNDERHILL, E. W., WETTER, L. R. and CHISOLM, M. D. (1973). Biosynthesis of glucosinolates. Biochemical Society Symposia, 38, 303-26.
131. VAJRESWARI, A., RAO, P. S. and TULPULE, P. G. (1990). Experimental myocardial-lipodosis. Influences of genetic dependant differences in response to erucic acid. Journal of Applied Cardiology, 5, 461-6.
132. VERHOEVEN, D. T. H., VERHAGEN, H., GOLDBOHM, R. A., VANDENBRANDT, P. A. and VANPOPPEL, G. (1997). A review of mechanisms underlying anticarcinogenicity by brassica vegetables. Chemico-Biological Interactions, 103, 79-129.
133. VOGT, H. (1981). Rapeseed meal in poultry rations. In: Production and utilization of protein in oilseed crops. (Bunting, E. S., Ed.), Martinus Nijhoff Publishers, The Hague, The Netherlands, 311-43.
134. WATERMAN, P. G. and MOLE, S. (1994a). Extraction and chemical quantification. In: Analysis of phenolic plant metabolites. Blackwell Scientific Publications, London, 66-103.
135. WATERMAN, P. G. and MOLE, S. (1994b). Biochemical techniques for tannins. In: Analysis of phenolic plant metabolites. Blackwell Scientific Publications, London, 104-33.
136. WELCH, R. W. (1978). Fully automated gradient elution system for amino acid analysis. Journal of Chromatography, 152, 528-30.
137. WETTER, L. R. (1957). The estimation of substituted thiooxazolidones in rapeseed meals. Canadian Journal of Biochemistry and Physiology, 35, 293-7.
138. WHITTLE, P. J., SMITH, R. H. and MCINTOSH, A. (1976). Estimation of S methylcysteine sulphoxide (kale anaemia factor) and its distribution among brassica forage and root crops. Journal of the Science of Food and Agriculture, 27, 633-42.
139. YAPAR, Z. and CLANDININ, D. R. (1972). Effects of tannins in rapeseed meal on its nutritional value for chicks. Poultry Science, 51, 222-8.
140. ZEMAN, L., SISKE, V. and HAP, I. (1994). The effects of administration of rapeseed meal to pregnant sows on the results of efficiency in the first three litters. Zivocisna Vyroba, 39, 903-16.
141. ZIEGLER, S. J. and STICHER, O. (1989). HPLC of S-alk(en)yl-L-cysteine derivatives in garlic including quantitative determination of (+)-S-allyl-L cysteine sulphoxide. Planta Medica, 55, 372-8.
142. ZHANG, Y. S., TALALAY, P., CHO, C. G. and POSNER, G. H. (1992). A major inducer of anticarcinogenic protective enzymes from broccoli-isolation and elucidation of structure. Proceedings of the National Academy of Science, 89, 2399-403.
143. ZHAO, F., EVANS, E. J., BILSBORROW, P. E., SCHNUG, E. and SYERS, J. K. (1992). Correction for protein content in the determination of the glucosinolate content of rapeseed by the X-RF method. Journal of the Science of Food and Agriculture, 58, 431-3.