Skip to main content
SpringerLink
Log in

Phenolic Constituents of Rapeseed

  • Chapter
Plant Polyphenols

Part of the book series: Basic Life Sciences ((BLSC,volume 59))

Abstract

Phenolic compounds of oilseed products are the hydroxylated derivatives of benzoic and cinnamic acids, coumarins, flavonoids, and lignins. Phenolic acids of rapeseed are in free, esterified, and insoluble bound forms. Phenolic esters and free phenolic acids constitute up to 80 percent and 16 percent of total phenolics of rapeseed, respectively, with sinapic acid being the predominant compound. The presence of tannins in cruciferae oilseeds has been documented through the formation of cyanidin, pelargonidin, and a n-butyl derivative of cyanidin artifact in hydrolytic products of rapeseed hulls. Recently, we reported that canola meals contained 0.68–0.77 percent tannins, as compared to 0.43–0.56 percent for Midas rapeseed meals. Rapeseed tannins are reported to cause tainting of eggs in laying hens. It has been suggested that rapeseed tannins block metabolism of trimethylamine (TMA) by inhibiting TMA oxidase, an enzyme that converts TMA to odorless water-soluble TMA-oxide. However, little is known about the rapeseed/canola tannin-protein interactions and their antinutritional effect in feeds. Ammoniated methanol removed 82 percent and 50 percent of esterified and free phenolic acids originally present in the seeds, respectively, though insoluble-bound phenolics were not affected, nearly half the tannins were removed by this treatment.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.00
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Shahidi, F. Rapeseed and canola: global production and distribution. In: Shahidi, F., (ed.). Canola and rapeseed: production, chemistry, nutrition, and processing technology. Van Nostrand Reinhold, New York, pp. 3–14 (1990).

    Chapter  Google Scholar 

  2. Ohlson, R. Functional properties of rapeseed oil and protein product—a survey. Proceedings, Fifth International Rapeseed Congress, Malmo, Sweden, pp. 152-156 (1978).

    Google Scholar 

  3. Delisle, J.; Amiot, J.; Goulet, G.; Simard, C.; Brisson, G.J.; Jones, J.D. Nutritive value of protein fractions extracted from soybean, rapeseed and wheat flours in the rat. Qual. Plant.-Plant Foods Hum. Nutr. 34:243 (1984).

    Article  CAS  Google Scholar 

  4. Daun, J.K. Glucosinolate levels in Western Canadian rapeseed and canola. J. Amer. Oil Chem. Soc. 63:639 (1986).

    Article  CAS  Google Scholar 

  5. Diosady, L.L.; Rubin, L.J.; Tar, C.G.; Etkin, B. Air classification of rapeseed meal using Tervel Separator. Can. J. of Chem. Eng. 64:768 (1986).

    Article  Google Scholar 

  6. Greilsamer, B. Depeliculage-Tirage des graines de colza (Dehulling and extraction of rapeseed). In: Proceedings, Sixth International Rapeseed Conference, Vol. II, Paris, pp. 1496-1501 (1983).

    Google Scholar 

  7. Kozlowska, H.; Zadernowski, R.; Lossow, B. Polish Patent No. 37490 (1984).

    Google Scholar 

  8. Sosulski, F.W.; Zadernowski, R. Fractionation of rapeseed meal into flour and hull component. J. Am. Oil Chem. Soc. 58:96 (1981).

    Article  Google Scholar 

  9. Kozlowska, H.; Sabir, M.A.; Sosulski, F.W.; Coxworth, E. Phenolic constituents of rapeseed flour. Can. Inst. Food Sci. Technot. J. 8:160 (1975).

    CAS  Google Scholar 

  10. Sosulski, F.W. Organoleptic and nutritional effects of phenolics. Review. J. Am. Oil Chem. Soc. 56:711 (1979).

    Article  CAS  Google Scholar 

  11. Ribereau-Gayon, P. Plant phenolics. Oliver and Boyd, Edinburg, (1972).

    Google Scholar 

  12. Rubin, L.J.; Diosady, L.L.; Phillips, C.R. Solvent extraction of oil bearing seeds. US Patent 4, 406, 504 (1984).

    Google Scholar 

  13. Fenwick, G.R.; Spinks, E.A.; Wilkinson, A.P.; Heaney, R.K.; Legoy, M.A. Effect of processing on the antinutrient content of rapeseed. J. Sci. Food Agric. 37:735 (1986).

    Article  CAS  Google Scholar 

  14. Naczk, M.; Shahidi, F.; Diosady, L.L.; Rubin, L.J. Removal of glucosinolates from Midas rapeseed and mustard seed by methanol-ammonia. Can. Inst. Food Sci. Technol. J. 19:75 (1986).

    CAS  Google Scholar 

  15. Shahidi, F.; Naczk, M.; Rubin, L.J.; Diosady, L.L. A novel processing approach for rapeseed and mustard seed-removal of undesirable constituents by methanol-ammonia. J. Food Protec. 51:743 (1988).

    CAS  Google Scholar 

  16. Schlingmann, M.; Prave, P. Single cell proteine mit reduziertem nukleinsaure und fattgehalt (Single cell proteins with reduced content of nucleic acid and fat). Fette Seifen Anstrichmittel 80(7):283 (1978).

    Article  CAS  Google Scholar 

  17. Schlingmann, M.; Vortesy, L. Verfahren zur Verminderung des lipid-und nukleinsaure-gehaltes in mikrobiellen zellmassen (Reducing the lipid and nucleic acid content in microbial cell masses). Fed. Rep. of Germany Patent 26, 33, 666 (1978).

    Google Scholar 

  18. Schlingmann, M.; von Rymon Lipinski, G.W. Process for treating meals and flours of oilseeds. U.K. Patent Application 2, 030, 441A (1980).

    Google Scholar 

  19. Schlingmann, M.; von Rymon Lipinski, G.W. Process for improving the properties of meals and flours of oily seeds. Canadian Patent 1, 120, 779 (1982).

    Google Scholar 

  20. Dabrowski, K.; Sosulski, F. Extraction of phenolic compounds from Canola during protein concentration and isolation. In: Proceedings, Sixth International Rapeseed Conference, Vol. II, Paris, pp. 1338-1342 (1983).

    Google Scholar 

  21. Kozlowska, H.; Rotkiewicz, D.A.; Zadernowski, R.; Sosulski, F.W. Phenolic acids in rape-seed and mustard. J. Am. Oil Chem. Soc. 60:1119 (1983).

    Article  CAS  Google Scholar 

  22. Krygier, K.; Sosulski, F.W.; Hogge, L. Free, esterified and insoluble-bound phenolic acids. 2. Composition of phenolic acids in rapeseed flour and hulls. J. Agric. Food Chem. 30:334 (1982).

    Article  CAS  Google Scholar 

  23. Naczk, M.; Diosady, L.L.; Rubin, L.J. The phytate and complex phenol content of meals produced by alkanol-ammonia/hexane extraction of canola. Lebensm.-Wiss. u. Technol. 19:13 (1986).

    CAS  Google Scholar 

  24. Naczk, M.; Shahidi, F. The effect of methanol-ammonia-water treatment on the content of phenolic acids of canola. Food Chtm. 31:159 (1989).

    Article  CAS  Google Scholar 

  25. Kozlowska, H.; Zadernowski, B. Phenolic compounds of rapeseed as factors limiting the utilization of protein in nutrition. Presented at the Third Chemical Congress of North America, Toronto, June 5-10 (1988).

    Google Scholar 

  26. Durkee, A.B.; Thivierge, P.A. Bound phenolic acids in Brassica and Sinapis oilseeds. J. Food Sci. 40:820 (1975).

    Article  CAS  Google Scholar 

  27. Shahidi, F.; Naczk, M. Contribution of sinapic acid to the phenolic constituents of solvent extracted cruciferae oilseeds. Bulletin de Liason n 15 du Groupe Polyphenols, Narbonne, France. Compte-rendu des Jour nées Internationales d’Etude et de l’Assemblée Generale 1990, Strasbourg, France, 9–11 Juillet, pp. 236-239 (1990).

    Google Scholar 

  28. Fenton, T.W.; Leung, J.; Clandinin, D.R. Phenolic components of rapeseed meal. J. Food Sci. 45:1702 (1980).

    Article  CAS  Google Scholar 

  29. Mueller, M.M.; Ryl, Elaine; Fenton, T.W.; Clandinin, D.R. Cultivar and growing location differences on the sinapine content of rapeseed. Can. J. Animal Sci. 58:579 (1978).

    Article  CAS  Google Scholar 

  30. Kerber, E.; Buchloh, G. The sinapine content of crucifer seeds. Agntw. Bot. 54:47 (1980).

    CAS  Google Scholar 

  31. Blair, R.; Reichert, R.D. Carbohydrate and phenolic constituents in a comprehensive range of rapeseed and canola fractions: nutritional significance for animals. J. Sci. Food Agric. 35:29 (1984).

    Article  PubMed  CAS  Google Scholar 

  32. Bate-Smith, E.C.; Ribereau-Gayon, P. Leucoanthocyanins in seeds. Qualitas Plant et Materiae Vtgetabilts 5:189 (1959).

    Article  CAS  Google Scholar 

  33. Durkee, A.B. The nature of tannins in rapeseed (Brassica campestris). Phytochemistry 10:1583 (1971).

    Article  CAS  Google Scholar 

  34. Leung, J.; Fenton, T.W.; Mueller, M.M.; Clandinin, D.R. Condensed tannins of rapeseed meal. J. Food Sci. 44:1313 (1979).

    Article  CAS  Google Scholar 

  35. AOAC Official methods of analysis. 15th ed. Washington, D.C.: Association of Official Analytical Chemists (1990).

    Google Scholar 

  36. Clandinin, D.R.; Heard, J. Tannins in prepress-solvent and solvent processed rapeseed meal. Poultry Sci. 47:688 (1968).

    Article  Google Scholar 

  37. Fenwick, R.G.; Hoggan, S.A. The tannin content of rapeseed meals. Br. Poultry Sci. 17:59 (1976).

    Article  CAS  Google Scholar 

  38. Fenwick, G.R.; Curl, C.L.; Butler, E.J.; Greenwood, N.M.; Pearson, A.W. Rapeseed meal and egg taint: Effects of low glucosinolate Brassica napus meal, dehulled meal and hulls, and of neomycin. J. Sei. Food Agric. 35:749 (1984).

    Article  CAS  Google Scholar 

  39. Price, M.L.; Van Scoyoc, S.; Butler, L.G. A critical evaluation of the vanillin reaction as an assay for tannin in sorghum grain. J. Agric. Food Chtm. 26:1214 (1978).

    Article  CAS  Google Scholar 

  40. Shahidi, F.; Naczk, M. Effect of processing on the phenolic constituents of canola. Bulletin de Liason n 14 du Groupe Polyphenols, Narbonne, France. Compte-rendu des Journees Internationales d’Etude et de l’Assemblee Generale 1988. St. Catharines, Canada, 16–19 aout, pp. 89-92 (1988).

    Google Scholar 

  41. Shahidi, F.; Naczk, M. Effect of processing on the content of condensed tannins in rapeseed meals. A research note. J. Food Sci. 54:1082 (1989).

    Article  CAS  Google Scholar 

  42. Shahidi, F.; Naczk, M. Solvent extraction of tannins from canola. Presented at Fiftieth Annual IFT Meeting. June 25–29, Chicago, IL (1989).

    Google Scholar 

  43. Mitaru, B.N.; Blair, R.; Bell, J.M.; Reichert, R.D. Tannin and fiber contents of rapeseed and canola hulls. Notes. Can. J. Animal Sci. 62:661 (1982).

    Article  CAS  Google Scholar 

  44. Gupta, R.K.; Haslam, E. Vegetable tannins-structure and biosynthesis. In: Hulse, J.H., (ed.). Polyphenols in cereals and legumes. IDRC, Ottawa, pp. 15–24 (1980).

    Google Scholar 

  45. Maxon, E.D.; Rooney, I. Evaluation of methods for tannin analysis in sorghum grain. Cereal Chtm. 49:719 (1972).

    Google Scholar 

  46. Naczk, M.; Shahidi, F. A critical evaluation of quantification methods of rapeseed tannins. Presented at the Eighth International Rapeseed Congress, Saskatoon, Canada, July 9–11 (1991).

    Google Scholar 

  47. Desphande, S.S.; Cheryan, M. Determination of phenolic compounds of dry beans using vanillin, redox and precipitation assays. J. Food Sci. 52:332 (1987).

    Article  Google Scholar 

  48. Dabrowski, K. and Sosulski, F. Composition of free and hydrozylable phenolic acids in defatted flours of ten oilseeds. J. Agric. Food Chem. 32:128 (1984).

    Article  CAS  Google Scholar 

  49. Kozlowska, H.; Zademowski, R. Production of protein preparates from rapeseed. In: Proceedings, Sixth International Rapeseed Conference, Vol. II, Paris, pp. 1412-1419 (1983).

    Google Scholar 

  50. McGregor, D.I.; Blake, J.A.; Pickard, M.D. Detoxification of Brassica juncea with ammonia. In: Proceedings, Sixth International Rapeseed Conference. Vol. II, Paris, pp. 1426 (1983).

    Google Scholar 

  51. Fenwick, G.R.; Hobson-Frohock, A.; Land, D.G.; Curtis, R.F. Rapeseed meal and egg taint: treatment of rapeseed meal to reduce tainting potential. Br. Poultry Sci. 20:323 (1979).

    Article  CAS  Google Scholar 

  52. Fenwick, G.R.; Curl, C.L.; Pearson, A.W.; Butler, E.J. The treatment of rapeseed meal and its effect on the chemical composition and egg tainting potential. J. Sci. Food Agric. 35:757 (1984).

    Article  CAS  Google Scholar 

  53. Goh, Y.K.; Shires, A.R.; Robblee, A.R.; Clandinin, D.R. Effect of ammoniation of rapeseed meal on the sinapine content of the meal. Br. Poultry Sci. 23:121 (1982).

    Article  CAS  Google Scholar 

  54. Diosady, L.L.; Tar, C.G.; Rubin, L.J.; Naczk, M. Scale-up of the production of glucosinolate-free canola meal. Acta. Alimentaria 16:167 (1987).

    CAS  Google Scholar 

  55. Gandhi, V.M.; Cheriyan, K.K.; Mulky, M.J.; Menon, K.K.G. Utilization of non-traditional indigenous oil-seed meal. 2. Studies with the detoxified salseed meal. J. Oil Technol. Assoc. India (Bombay) 7:44 (1975).

    CAS  Google Scholar 

  56. Swain, T. Tannins and lignins. In: Rosenthal, G.A.J.; Janzen, D.; (eds.). Herbivores: their interaction with secondary plant metabolites. Academic Press, New York, (1979).

    Google Scholar 

  57. Arai, S.H.; Suzuki, H.; Fujimaki, M.; Sakurai, Y. Flavor components in soybean. II. Phenolic acids in defatted soybean flour. Agric. Biol. Chem. 30:364 (1966).

    Article  CAS  Google Scholar 

  58. Maga, J.A.; Lorenz, K. Taste thresholds values for phenolic acids which can influence flavor properties of certain flours, grains, and oilseeds. Cereal Sci. Today 18:326 (1973).

    CAS  Google Scholar 

  59. Maga, J.A.; Lorenz, K. Gas-liquid chromatography separation of the free phenolic acid fractions in oilseed protein sources. J. Sci. Food Agrie. 25:797 (1974).

    Article  CAS  Google Scholar 

  60. Sosulski, F.W.; Humbert, E.S.; Lin, M.J.Y.; Card, J.W. Rapeseed-supplemented wieners. Can. Insi. Food Sci. Teehnol. J. 10:9 (1977).

    Google Scholar 

  61. Appelqvist, L.-A. Chemical constituents of rapeseed. In: Appelquist, L.A.; Ohlson, R., (eds.). Rapeseed. Elsevier Publ., Amsterdam, pp. 168–180 (1972).

    Google Scholar 

  62. Butler, E.J.; Pearson, A.W.; Fenwick, G.R. Problems which limit the use of rapeseed meal as a protein source in poultry diets. J. Sci. Food Agric. 33:866 (1982).

    Article  PubMed  CAS  Google Scholar 

  63. Hobson-Frohock, A.; Land, D.G.; Griffiths, N.M.; Curtis, R.F. Egg taints: association with trimethylamine. Nature 243:303–305 (1973).

    Article  Google Scholar 

  64. Pearson, A.W.; Butler, E.J.; Fenwick, G.R. Rapeseed meal and egg taint: the role of sinapine. J. Sci. Food Agric. 31:898–904 (1980).

    Article  PubMed  CAS  Google Scholar 

  65. Smyk, B.; Drabent, R. Spectroscopic investigation of equilibria of the ionic form of sinapic acid. Analyst 114:723 (1989).

    Article  CAS  Google Scholar 

  66. Clandinin, D.R. and Robblee, A.R. Rapeseed meal in animal nutrition. II. Non-ruminant animals. J. Am. Oil Chem. Soc. 58:682 (1981).

    Article  CAS  Google Scholar 

  67. Martin-Tanguy, J.; Guillaume, J.; Kossa, A. Condensed tannins in horse bean seeds: chemical structure and apparent effects on poultry. J. Sci. Food Agric. 28:757 (1977).

    Article  CAS  Google Scholar 

  68. Kumar, R.; Singh, M. Tannins: their adverse role in ruminant nutrition. Review. J. Agric. Food Chem. 32:447 (1984).

    Article  CAS  Google Scholar 

  69. Fenwick, G.R.; Pearson, A.W.; Greenwood, N.M.; Butler, E.G. Rapeseed meal tannins and egg taint. Anim. Feed Sci. Technol. 6:421 (1981).

    Article  CAS  Google Scholar 

  70. Yapar, Z.; Clandinin, D.R. Effect of tannins in rapeseed meal on its nutritional value for chicks. Poultry Sci. 51:222 (1972).

    Article  CAS  Google Scholar 

  71. Desphande, S.S.; Cheryan, M.; Salunkhe, D.K. Tannin analysis of food products. CRC Crit. Rev. Food Sci. Nutr. 24:401 (1986).

    Article  Google Scholar 

  72. Makkar, H.P.S. Protein precipitation methods for quantification of tannins: a review. J. Agric. Food Chem. 37:1197 (1989).

    Article  CAS  Google Scholar 

  73. Hagerman, A.E.; Butler, L.G. The specifity of proanthocyanidin-protein interaction. J. Biol. Chem. 256:4494 (1981).

    PubMed  CAS  Google Scholar 

  74. Oh, H.I.; Hoff, J.E.; Armstrong, G.S.; Haff, L.A. Hydrophobie interaction in tannin-protein complexes. J. Agrie. Food Chem. 28:394 (1980).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Nutrition and Consumer Studies, St. Francis Xavier University, Antigonish, Novia Scotia, B2G 1C0, Canada

    Marian Naczk

  2. Department of Biochemistry, Memorial University of Newfoundland, St. John’s, Newfoundland, A1B 3X9, Canada

    Fereidoon Shahidi

Authors
  1. Marian Naczk
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fereidoon Shahidi
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. United States Department of Agriculture, Forest Service, Pineville, Louisiana, USA

    Richard W. Hemingway

  2. Institute of Wood Research, Houghton, Michigan, USA

    Peter E. Laks

Rights and permissions

Reprints and permissions

Copyright information

© 1992 Springer Science+Business Media New York

About this chapter

Cite this chapter

Naczk, M., Shahidi, F. (1992). Phenolic Constituents of Rapeseed. In: Hemingway, R.W., Laks, P.E. (eds) Plant Polyphenols. Basic Life Sciences, vol 59. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3476-1_53

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-3476-1_53

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-6540-2

  • Online ISBN: 978-1-4615-3476-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation