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.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
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: 364
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: 207
Bosshard, H. (1972). Ueber die Anlagerung von Thioathern an Chinone und Chinonimine in stark sauren Medien. Helv. Chim. Acta55: 32
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: 508
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. 153
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: 85
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, Vienna
Eklund, A. (1975). Effect of chlorogenic acid in a casein diet for rats. Nutr. Metab. 18: 259
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 York
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: 325
Free, B.L. and Satterlee, L.D. (1975). Biochemical properties of alpha protein concentrate. J. Fd Sci. 40: 85
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: 1093
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, London
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, London
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 260
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: 191
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, Basel
Kuhnau, J. (1976). The flavonoids. A class of semi-essential food components: their role in human nutrition. Wld Rev. Nutr. Diet24: 117
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: 797
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: 155
Mason, H.S. (1955). Comparative biochemistry of the phenolase complex. Adv. Enzym. 16: 105
Milic, B., Stojanovic, S., Vucurevic, N. and Turcic, M. (1968). Chlorogenic and quinic acids in sunflower meal. J. Sci. Fd Agric. 19: 108
Pierpoint, W.S. (1969a). o-Quinones formed in plant extracts. Their reaction with amino acids and peptides. Biochem. J. 112: 609
Pierpoint, W.S. (1969b). o-Quinones formed in plant extracts. Their reaction with bovine serum albumin. Biochem. J. 112: 619
Pierpoint, W.S. (1971). Formation and behaviour of o-quinones in some processes of agricultural importance. Rep. Rothamsted exp. Stn, part 2, p. 199
Pomenta, J.V. and Burns, E.E. (1971). Factors effecting chlorogenic, quinic and caffeic acid levels in sunflower kernels. J. Fd Sci. 36: 490
Sabir, M.A., Sosulski, F.W. and Kernan, J.A. (1974). Phenolic constituents in sunflower flour. J. Agric. Fd Chem. 22, 512
Sodini, G. and Canella, M. (1977). Acid butanol removal of color-forming phenols from sunflower meal. J. Agric. Fd Chem. 25: 822
Synge, R.L.M. (1975). Interactions of polyphenols in plants and plant products. Qual. Plant. PI. Fds hum. Nutr. 24: 337
Vithayathil, P.J. and Murphy, G.S. (1972). New reaction of o-benzoquinone at the thioether group of methionine. Nature New Biol. 236: 101.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1984 Plenum Press, New York
About this chapter
Cite this chapter
Hurrell, R.F., Finot, PA. (1984). Nutritional Consequences of the Reactions Between Proteins and Oxidized Polyphenolic Acids. In: Friedman, M. (eds) Nutritional and Toxicological Aspects of Food Safety. Advances in Experimental Medicine and Biology, vol 177. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-4790-3_20
Download citation
DOI: https://doi.org/10.1007/978-1-4684-4790-3_20
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4684-4792-7
Online ISBN: 978-1-4684-4790-3
eBook Packages: Springer Book Archive