Effects of non-covalent interactions with 5-O-caffeoylquinic acid (chlorogenic acid) on the heat denaturation and solubility of globular proteins

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 17, 2003, Pages 5088-5095

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

^a TNO   (Netherlands)

^b WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

lactalbumin; BSA; Ionic strength; Lysozyme; PH; Phenolic compounds; Temperature

Indexed keywords

ALPHA LACTALBUMIN; BOVINE SERUM ALBUMIN; CHLOROGENIC ACID; GLOBULAR PROTEIN; LYSOZYME;

ACIDITY; ALKALINITY; ARTICLE; COVALENT BOND; ENTHALPY; FOOD; HIGH TEMPERATURE; IONIC STRENGTH; MOLECULAR INTERACTION; PROTEIN DENATURATION; SOLUBILITY; TEMPERATURE DEPENDENCE; TEMPERATURE SENSITIVITY;

CHLOROGENIC ACID; DRUG INTERACTIONS; HEAT; HYDROGEN-ION CONCENTRATION; LACTALBUMIN; MURAMIDASE; OSMOLAR CONCENTRATION; PROTEIN DENATURATION; SERUM ALBUMIN, BOVINE; SOLUBILITY; THERMODYNAMICS;

BOVINAE;

EID: 0042061110     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf021229w     Document Type: Article

References (39)

1. Bate-Smith, E. C.; Swain, In T. Comparative Biochemistry; Mason, H. S., Florkin, A. M., Eds.; Academic Press: New York, 1962; Vol. 3, p 764.
2. Siebert, K. J. Effect of protein-polyphenol interactions on beverage haze, stabilization, and analysis. J. Agric. Food Chem. 1999, 47, 353-362.
3. Van Koningsveld, G.; Gruppen, H.; de Jongh, H. J.; Wijngaards, G.; van Boekel, M. A. J. S.; Walstra, P.; Voragen, A. G. J. The solubility of potato proteins from industrial potato fruit juice as influenced by pH and various additives. J. Sci. Food Agric. 2002, 82, 134-142.
4. Sarker, D. K.; Wilde, P. J.; Clarck, D. C. Control of surfactant-induced destabilization of foams through polyphenol-mediated protein-protein interactions. J. Agric. Food Chem. 1995, 43, 295-300.
5. O'Connell, J. E.; Fox, P. F. Effect of phenolic compounds on the heat stability of milk and concentrated milk. J. Dairy Res. 1999, 66, 399-407.
6. Haslam, E. In Plant Polyphenols: Vegetable Tannins Revisited; Phillipson, J. D., Ayres, D. C., Baxter H., Eds.; Cambridge University Press: Cambridge, U.K., 1989; p 230.
7. 1H-NMR spectroscopy. Eur. J. Biochem. 1994, 219, 923-935.
8. Baxter, N. J.; Lilley, T. H.; Haslam, E.; Williamson, M. P. Multiple interactions between polyphenols and a salivary proline-rich protein repeat result in complexation and precipitation. Biochemistry 1997, 36, 5566-5577.
9. Charlton, A. J.; Baxter, N. J.; Lilley, T. H.; Haslam, E.; McDonald, C. J.; Williamson, M. P. Tannin interactions with a full-length human salivary proline-rich protein display a stronger affinity than with single proline-rich repeats. FEBS Lett. 1996, 382, 289-292.
10. Charlton, A. J.; Baxter, N. J.; Lokman, M. K.; Moir, A. J. G.; Haslam, E.; Davies, A. P.; Williamson, M. P. Polyphenol/peptide binding and precipitation. J. Agric. Food Chem. 2002, 50, 1593-1601.
11. De Freitas, V.; Mateus, N. Structural features of procyanidin interactions with salivary proteins. J. Agric. Food Chem. 2001, 49, 940-945.
12. Hagerman, A. E.; Butler, L. G. The specificity of proanthocyanidin-protein interactions. J. Biol. Chem. 1981, 256, 4494-4497.
13. Haslam, E. Natural polyphenols (vegetable tannins) as drugs: possible modes of action. J. Nat. Prod. 1996, 59, 205-215.
14. Lu, Y.; Bennick, A. Interaction of tannin with human salivary proline-rich proteins. Arch. Oral Biol. 1998, 43, 717-728.
15. Oh, H. I.; Hoff, J. E.; Armstrong, G. S.; Haff, L. A. Hydrophobic interaction in tannin-protein complexes. J. Agric. Food Chem. 1980, 28, 394-398.
16. Artz, W. E.; Bishop, P. D.; Dunker, A. K.; Schanus, E. G.; Swanson, B. G. Interaction of synthetic proanthocyanidin dimer and trimer with bovine serum albumin and purified bean globulin fraction G-1. J. Agric. Food Chem. 1987, 35, 417-421.
17. Shamanthaka Sastry, M. C.; Narasinga Rao, M. S. Binding of chlorogenic acid by the isolated polyphenol-free 11S protein of sunflower (Helianthus annuus) seed. J. Agric. Food Chem. 1990, 38, 2103-2110.
18. Bartolomé, B.; Estrella, I.; Hernández, M. T. Interaction of low molecular weight phenolics with proteins (BSA). J. Food Sci. 2000, 65, 617-621.
19. Clifford, M. N. Review. Chlorogenic acids and other cinnamates - nature, occurrence, dietary burden, absorption and metabolism. J. Sci. Food Agric. 2000, 80, 1033-1043.
20. Robards, K.; Prenzler, P. D.; Tucker, G.; Swatsitang, P.; Glover, W. Phenolics compounds and their role in oxidative processes in fruits. Food Chem. 1999, 66, 401-436.
21. Privalov, P. L. Stability of proteins. Small globular proteins. Adv. Protein Chem. 1979, 33, 167-241.
22. Scatchard, G. The attraction of proteins for small molecules and ions. Ann. N. Y. Acad. Sci. 1949, 51, 660-672.
23. Weder, H. G.; Schildknecht, J.; Lutz, R. A.; Kesselring, P. Determination of binding parameters from Scatchard plots. Theoretical and practical considerations. Eur. J. Biochem. 1974, 42, 475-481.
24. Hummel, J. P.; Dreyer, W. J. Measurement of protein-binding phenomena by gel filtration. Biochim. Biophys. Acta 1962, 63, 530-532.
25. Busch, M. H. A.; Kraak, J. C.; Poppe, H. Principles and limitations of methods available for the determination of binding constants with affinity capillary electrophoresis. J. Chromatogr. A 1997, 777, 329-353.
26. Boyes, S.; Strubi, P.; Dawes, H. Measurement of protein content in fruit juices, wine and plant extracts in the presence of endogenous organic compounds. Lebensm. Wiss. -Technol. 1997, 30, 778-785.
27. Phe binding to eukaryotic ribosomes. Biochem. J. 1997, 325, 401-404.
28. Wang, Z.-H.; Pan, X.-M. Kinetic differenciation between ligand-induced and pre-existent asymmetric models. FEBS Lett. 1996, 388, 73-75.
29. Wiseman, T.; Williston, S.; Brandts, J. F.; Lin, L.-N. Rapid measurement of binding constants and heats of binding using a new titration calorimeter. Anal. Biochem. 1989, 179, 131-137.
30. Naczk, M.; Oickle, D.; Pink, D.; Shahidi, F. Protein precipitating capacity of crude canola tannins: effect of pH, tannin, and protein concentrations. J. Agric. Food Chem. 1996, 44, 2144-2148.
31. Li-Chan, E. Hydrophobicity in food protein systems. In Encyclopedia of Food Science and Technology; Hui, Y. H., Ed.; Wiley-Interscience: New York, 1990; pp 1429-1439.
32. Relkin, P. Thermal unfolding of β-lactoglobulin, α-lactalbumin, and bovine serum albumin. A thermodynamic approach. Crit. Rev. Food Sci. Nutr. 1996, 36, 565-601.
33. Creighton, T. E. In Proteins: Structures and Molecular Properties, 2nd ed.; Freeman, Library of Congress Cataloging-in-Publication Data: New York, 1993.
34. Cooper, A.; Nutley, M. A.; Wadood, A. In Protein-Ligand Interactions: Hydrodynamics and Calorimetry. A Practical Approach; Harding, S. E., Chowdhry, B. Z., Eds.; Oxford University Press: Oxford, U.K., 2001.
35. Matheis, G.; Whitaker, J. R. Modification of proteins by polyphenol oxidase and peroxidase and their products. J. Food Biochem. 1984, 8, 137-162.
36. Rawel, H. M.; Kroll, J.; Riese, B. Reactions of chlorogenic acid with lysozyme: physicochemical characterization and proteolytic digestion of the derivatives. J. Food Sci. 2000, 65, 1091-1098.
37. Namiki, M.; Yabuta, G.; Koizumi, Y.; 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. 2001, 65, 2131-2136.
38. Rawel, H. M.; Rohn, S.; Kruse, H.-P.; Kroll, J. Structural changes induced in bovine serum albumin by covalent attachment of chlorogenic acid. Food Chem. 2002, 78, 443-455.
39. Gonzalez-Perez, S.; Merck, K. B.; Vereijken, J. M.; Van Koningsveld, G. A.; Gruppen, H.; Voragen, A. G. J. Isolation and characterization of undenatured chlorogenic acid free sunflower (Helianthus annuus) proteins. J. Agric. Food Chem. 2002, 50, 1713-1719.