Advertisement

Nutritional Consequences of the Reactions Between Proteins and Oxidized Polyphenolic Acids

  • Richard F. Hurrell
  • Paul-André Finot
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 177)

Abstract

The chemical and enzymatic browning reactions of plant polyphenols and their effects on amino acids and proteins are reviewed. A model system of casein and oxidizing caffeic acid has been studied in more detail. The effects of pH, time, caffeic acid level and the presence or not of tyrosinase on the decrease of FDNB-reactive lysine are described. The chemical loss of lysine, methionine and tryptophan and the change in the bioavailability of these amino acids to rats has been evaluated in two systems : pH 7.0 with tyrosinase and pH 10.0 without tyrosinase. At pH 10.0, reactive lysine was more reduced. At pH 7.0 plus tyrosinase methionine was more extensively oxidized to its sulphoxide. Tryptophan was not chemically reduced under either condition. At pH 10.0 there was a decrease in the protein digestibility which was responsible for a corresponding reduction in tryptophan availability and partly responsible for lower methionine availability. Metabolic transit of casein labelled with tritiated lysine treated under the same conditions indicated that the lower lysine availability in rats was due to a lower digestibility of the lysine-caffeoquinone complexes.

Keywords

Phenolic Acid Caffeic Acid Chlorogenic Acid Protein Digestibility Quinic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Arai, S., Suzuki, H., Fujimaki, M. and Sakwiai, Y. (1966). Studies on the flavor components in soybean. Part II. Phenolic acids in defatted soybean flour. Agric. Biol. Chem., 30: 364CrossRefGoogle Scholar
  2. Bau, H.M. and Debry, G. (1980). Colourless sunflower protein isolates: chemical and nutritional evaluation of the pre-sence of phenolic compounds. J. Jed Technol. 15: 207Google Scholar
  3. Bosshard, H. (1972). Ueber die Anlagerung von Thioathern an Chinone und Chinonimine in stark sauren Medien. Helv. Chim. Acta55: 32CrossRefGoogle Scholar
  4. Cater, C.M., Gheyasuddin, S. and Mattil, K.F. (1972). The effect of chlorogenic, quinic and caffeic acids on the solubility and color of protein isolates, especially from sunflower seed. Cereal Chem. 49: 508Google Scholar
  5. Cheftel, J.C. (1979). Proteins and amino acids, in: Nutritional and safety aspects of food processing, S.R. Tannenbaum, ed., Marcel Dekker, New York, p. 153Google Scholar
  6. Cuq, J.L., Besançon, P., Chartier, L. and Cheftel, J.C. (1978). Oxidation of methionine residues of food proteins and nutritional availability of methionine sulphoxide. Food Chem. 3: 85CrossRefGoogle Scholar
  7. Eggum, B.O. and Christensen, K.D. (1975). Influence of tannin on protein utilization in feedstuffs with special reference to barley, in Breeding for seed protein improvement using nuclear techniques, p. 135, International Atomic Energy Agency, ViennaGoogle Scholar
  8. Eklund, A. (1975). Effect of chlorogenic acid in a casein diet for rats. Nutr. Metab. 18: 259Google Scholar
  9. Finley, J.W. and Lundin, R.E. (1980). Lipid hydroperoxide induced oxidation of cysteine in peptides, in Autoxidation in food and biological systems, p. 223, M.G. Simic and M. Karel, eds, Plenum Press, New YorkGoogle Scholar
  10. Ford, J.E. and Hewitt, D. (1979). Protein quality in cereals and pulses. 3. Bioassays with rats and chickens on sorghum, barley and field beans. Influence of polyethylene glycol on digestibility of the protein in high tannin grain. Bj. J. Nutr. 42: 325CrossRefGoogle Scholar
  11. Free, B.L. and Satterlee, L.D. (1975). Biochemical properties of alpha protein concentrate. J. Fd Sci. 40: 85CrossRefGoogle Scholar
  12. Horigome, T. and Kandatsu, M. (1968). Biological value of protein allowed to react with phenolic compounds in presence of o-diphenol oxidase. Agric. Biol. Chem. 32: 1093CrossRefGoogle Scholar
  13. Hurrell, R.F. (1980). Interaction of food components during processing, in Food and Health: Science and Technology, p. 369, G.G. Birch and K.J. Parker, eds., Applied Science, LondonGoogle Scholar
  14. Hurrell, R.F. and Carpenter, K.J. (1977). Maillard reactions in foods, in Physical, chemical and biological changes in food caused by thermal processing, p. 168, T. Hoyem and O. Kvale, eds., Applied Science, LondonGoogle Scholar
  15. Hurrell, R.F., Finot, P.A., Jaussan, V. and Cuq, J.L. (1981). Nutritional consequences of protein-polyphenol browning reactions. XIVth International Congress of Nutrition, San Diego, California, Abstract 260Google Scholar
  16. Hurrell, R.F., Finot, P.A. and Cuq, J.L. (1982). Protein-polyphenol reactions. 1. Nutritional and metabolic consequences of the reaction between oxidized caffeic acid and the lysine residues of casein. Br. J. Nutr. 47: 191Google Scholar
  17. Hurrell, R.F. and Finot, P.A. (1983). Food processing and storage as a determinant of protein and amino acid availability, in Nutritional Adequacy, Nutrient Availability and Needs, p. 135, J. Mauron, ed., Birhauser Verlag, BaselGoogle Scholar
  18. Kuhnau, J. (1976). The flavonoids. A class of semi-essential food components: their role in human nutrition. Wld Rev. Nutr. Diet24: 117Google Scholar
  19. Maga, J.A. and Lorenz, K. (1974). Gas-liquid chromatography separation of free phenolic acid fractions in various oilseed protein sources. J. Sci. Fd Agric. 25: 797CrossRefGoogle Scholar
  20. Marable, N.L., Todd, J.M., Korslund, M.K. and Kennedy, B.W. (1980). Human urine and/or plasma levels of methionine, methionine sulphoxide and inorganic sulphur after consumption of a soy isolate: A preliminary study. Qual. Plant PI Fds Hum. Nutr. 30: 155CrossRefGoogle Scholar
  21. Mason, H.S. (1955). Comparative biochemistry of the phenolase complex. Adv. Enzym. 16: 105Google Scholar
  22. Milic, B., Stojanovic, S., Vucurevic, N. and Turcic, M. (1968). Chlorogenic and quinic acids in sunflower meal. J. Sci. Fd Agric. 19: 108CrossRefGoogle Scholar
  23. Pierpoint, W.S. (1969a). o-Quinones formed in plant extracts. Their reaction with amino acids and peptides. Biochem. J. 112: 609Google Scholar
  24. Pierpoint, W.S. (1969b). o-Quinones formed in plant extracts. Their reaction with bovine serum albumin. Biochem. J. 112: 619Google Scholar
  25. Pierpoint, W.S. (1971). Formation and behaviour of o-quinones in some processes of agricultural importance. Rep. Rothamsted exp. Stn, part 2, p. 199Google Scholar
  26. Pomenta, J.V. and Burns, E.E. (1971). Factors effecting chlorogenic, quinic and caffeic acid levels in sunflower kernels. J. Fd Sci. 36: 490CrossRefGoogle Scholar
  27. Sabir, M.A., Sosulski, F.W. and Kernan, J.A. (1974). Phenolic constituents in sunflower flour. J. Agric. Fd Chem. 22, 512CrossRefGoogle Scholar
  28. Sodini, G. and Canella, M. (1977). Acid butanol removal of color-forming phenols from sunflower meal. J. Agric. Fd Chem. 25: 822CrossRefGoogle Scholar
  29. Synge, R.L.M. (1975). Interactions of polyphenols in plants and plant products. Qual. Plant. PI. Fds hum. Nutr. 24: 337CrossRefGoogle Scholar
  30. Vithayathil, P.J. and Murphy, G.S. (1972). New reaction of o-benzoquinone at the thioether group of methionine. Nature New Biol. 236: 101.PubMedCrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1984

Authors and Affiliations

  • Richard F. Hurrell
    • 1
  • Paul-André Finot
    • 1
  1. 1.Reseach DepartmentNestlé Products Technical Assistance Co. Ltd.La Tour de PeilzSwitzerland

Personalised recommendations