Covalent interactions between proteins and oxidation products of caffeoylquinic acid (chlorogenic acid)

Journal of the Science of Food and Agriculture

Volumn 87, Issue 13, 2007, Pages 2502-2510

  Prigent, Stéphanie V E ^a   Voragen, Alfons G J ^a   Visser, Antonie J W G ^a   Van Koningsveld, Gerrit A ^a   Gruppen, Harry ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

lactalbumin; BSA; Chlorogenic acid; Lysozyme; Polyphenol oxidase; Quinone

Indexed keywords

BOVINAE;

EID: 35148823238     PISSN: 00225142     EISSN: 10970010     Source Type: Journal    
DOI: 10.1002/jsfa.3011     Document Type: Article

References (32)

1. Felton GW, Broadway RM and Duffey SS, Inactivation of protease inhibitor activity by plant-derived quinones: complications for host-plant resistance against noctuid herbivores. J Insect Physiol 35:981-990 (1989).
2. Siebert KJ, Effect of protein-polyphenol interactions on beverage haze, stabilization, and analysis. J Agric Food Chem 47:353-362 (1999).
3. Charlton AJ, Baxter NJ, Lokman MK, Moir AJG, Haslam E, Davies AP, et al, Polyphenol/peptide binding and precipitation. J Agric Food Chem 50:1593-1601 (2002).
4. Kroll J, Rawel HM and Rohn S, Reactions of plant phenolics with food proteins and enzymes under special consideration of covalent bonds. Food Sci Technol Res 9:205-218 (2003).
5. Arts MJTJ, Haenen GRMM, Voss H-P and Bast A, Masking of antioxidant capacity by the interaction of flavonoids with protein. Food Chem Toxicol 39:787-791 (2001).
6. Torres JL and Bobet R, New flavanol derivatives from grape (Vitis vinifera) byproducts. Antioxidant aminoethylthio-flavan-3-ol conjugates from a polymeric waste fraction used as a source of flavanols. J Agric Food Chem 49:4627-4634 (2001).
7. Gonzalez-Perez S, Merck KB, Vereijken JM, Van Koningsveld GA, Gruppen H and Voragen AGJ, Isolation and characterization of undenatured chlorogenic acid free sunflower (Helianthus annuus) proteins. J Agric Food Chem 50:1713-1719 (2002).
8. Van Koningsveld GA, Gruppen H, de Jongh HJ, Wijngaards G, van Boekel MAJS, Walstra P, et al, The solubility of potato proteins from industrial potato fruit juice as influenced by pH and various additives. J Sci Food Agric 82:134-142 (2002).
9. Sarker DK, Wilde PJ and Clark DC, Control of surfactant-induced destabilization of foams through polyphenol-mediated protein-protein interactions. J Agric Food Chem 43:295-300 (1995).
10. Strauss G and Gibson SM, Plant phenolics as cross-linkers of gelatin gels and gelatin-based coacervates for use as food ingredients. Food Hydrocoll 18:81-89 (2004).
11. Oudgenoeg G, Hilhorst R, Piersma SR, Boeriu CG, Gruppen H, Hessing M, et al, Peroxidase-mediated cross-linking of a tyrosine-containing peptide with ferulic acid. J Agric Food Chem 49:2503-2510 (2001).
12. Richard-Forget FC and Gauillard FA, Oxidation of chlorogenic acid, catechins, and 4-methylcatechol in model solutions by combinations of pear (Pyrus communis Cv. Williams) polyphenol oxidase and peroxidase; a possible involvement of peroxidase in enzymatic browning. J Agric Food Chem 45:2472-2476 (1997).
13. García P, Concepción R, Brenes M and Garrido A, Effect of metal cations on the chemical oxidation of olive o-diphenols in model systems. J Agric Food Chem 44:2101-2105 (1996).
14. Harrison CR and Hodge P, Polymer-supported periodate and iodate as oxidizing agents. J Chem Soc, Perkin Trans 1 509-511 (1982).
15. Cheynier V, Osse C and Rigaud J, Oxidation of grape juice phenolic compounds in model solutions. J Food Sci 53:1729-1732 (1988).
16. Pierpoint WS, o-Quinones formed in plant extracts. Their reaction with bovine serum albumin. Biochem J 112:619-629 (1969).
17. Rawel HM, Kroll J and Riese B, Reactions of chlorogenic acid with lysozyme: physicochemical characterization and proteolytic digestion of the derivatives. J Food Sci 65:1091-1098 (2000).
18. Rawel HM, Kroll J and Rohn S, Reactions of phenolic substances with lysozyme - physicochemical characterisation and proteolytic digestion of the derivatives. Food Chem 72:59-71 (2001).
19. Rawel HM, Rohn S, Kruse H-P and Kroll J, Structural changes induced in bovine serum albumin by covalent attachment of chlorogenic acid. Food Chem 78:443-455 (2002).
20. Prigent SVE, Gruppen H, Visser AJWG, van Koningsveld G, de Jong GAH and Voragen AGJ, Effects of non-covalent interactions with 5-O-caffeoylquinic acid (chlorogenic acid) on the heat denaturation and solubility of globular proteins. J Agric Food Chem 51:5088-5095 (2003).
21. Church FC, Swaisgood HE, Porter DH and Catignani GL, Spectrophotometric assay using o-phthaldialdehyde for determination of proteolysis in milk and isolated milk proteins. J Dairy Sci 66:1219-1227 (1983).
22. Caessens PWJR, Gruppen H, Visser S, Van Aken GA and Voragen AGJ, Plasmin hydrolysis of β-casein: foaming and emulsifying properties of the fractionated hydrolysate. J Agric Food Chem 45:2935-2941 (1997).
23. Namiki M, Yabuta G, Koizumi Y and Yano M, Development of free radical products during the greening reaction of caffeic acid esters (or chlorogenic acid) and a primary amino compound. Biosci Biotechnol Biochem 65:2131-2136 (2001).
24. Singleton VL, Oxygen with phenols and related reactions in musts, wines and model systems: observations and practical implications. Am J Enol Vitic 38:69-77 (1987).
25. Hurrell RF, Finot PA and Cuq JL, Protein-polyphenol reactions. 1. Nutritional and metabolic consequences of the reaction between oxidized caffeic acid and the lysine residues of casein. Br J Nutr 47:191-211 (1982).
26. Fujita Y, Hidaka Y and Noda Y, Thermal stability of alkylated and hydroxyalkylated lysozymes. Thermochim Acta 253:117-125 (1995).
27. Pierpoint WS, Ireland RJ and Carpenter JM, Modification of proteins during the oxidation of leaf phenols: reaction of potato virus X with chlorogenoquinone. Phytochemistry 16:29-34 (1977).
28. Kramer KJ, Kanost MR, Hopkins TL, Jiang H and Zhu YC, Oxidative conjugation of catechols with proteins in insect skeletal systems. Tetrahedron 57:385-392 (2001).
29. Penalver MJ, Rodríguez-López JN, García-Molina F, García-Cánovas F and Tudela J, Method for the determination of molar absorptivities of thiol adducts formed from diphenolic substrates of polyphenol oxidase. Anal Biochem 309:180-185 (2002).
30. Aeschbach R, Amadò R and Neukom H, Formation of dityrosine cross-links in proteins by oxidation of tyrosine residues. Biochim Biophys Acta 439:292-301 (1976).
31. Lissitzky S, Rolland M, Reynaud J and Lasry S, Oxydation de la tyrosine et de peptides ou protéines la contenant par la polyphenoloxidase de champignon. III. Propriétés des protéines oxydées et de certaines DOPA-protéines. Biochim Biophys Acta 65:481-494 (1962).
32. Oudgenoeg G, Peroxidase catalysed conjugation of peptides, proteins and polysaccharides via endogenous and exogenous phenols. PhD Thesis, Wageningen University (2004).