A review of methods used for investigation of protein–phenolic compound interactions

International Journal of Food Science and Technology

Volumn 52, Issue 3, 2017, Pages 573-585

  Czubinski, Jaroslaw ^a   Dwiecki, Krzysztof ^a  

^a POZNA UNIVERSITY OF LIFE SCIENCES   (Poland)

Author keywords

Antioxidants; bioavailability; covalent bonds; noncovalent bonds; protein polyphenol complexes; spectroscopic methods

Indexed keywords

AGENTS; ANTIOXIDANTS; BIOCHEMISTRY; COVALENT BONDS; FOOD PRODUCTS; PHENOLS; PROTEINS; SPECTROSCOPIC ANALYSIS;

ANALYTICAL METHOD; ANTIOXIDANT CAPACITY; BIOAVAILABILITY; NONCOVALENT BOND; NUTRITIONAL AND FUNCTIONAL PROPERTIES; PHENOLIC COMPOUNDS; POLYPHENOLS; SPECTROSCOPIC METHOD;

COMPLEXATION;

EID: 85007573995     PISSN: 09505423     EISSN: 13652621     Source Type: Journal    
DOI: 10.1111/ijfs.13339     Document Type: Review

References (67)

1. Al-Hanish, A., Stanic-Vucinic, D., Mihailovic, J. et al. (2016). Noncovalent interactions of bovine α-lactalbumin with green tea polyphenol, epigalocatechin-3-gallate. Food Hydrocolloids, 61, 241–250.
2. Ali, H., Alli, I., Ismail, A. & Kermasha, S. (2012). Protein-phenolic interactions in food. Eurasian Journal of Analytical Chemistry, 7, 123–133.
3. Arts, M.J., Haenen, G.R., Voss, H.P. & Bast, A. (2001). Masking of antioxidant capacity by the interaction of flavonoids with protein. Food and Chemical Toxicology, 39, 781–791.
4. Arts, M.J.T.J., Haenen, G.R., Wilms, L.C. et al. (2002). Interactions between flavonoids and proteins: effect on the total antioxidant capacity. Journal of Agricultural and Food Chemistry, 50, 1184–1187.
5. Bae, M.-J., Ishii, T., Minoda, K. et al. (2009). Albumin stabilizes (-)-epigallocatechin gallate in human serum: binding capacity and antioxidant property. Molecular Nutrition and Food Research, 53, 709–715.
6. Bartolome, B., Estrella, I. & Hernandez, M.T. (2000). Interaction of low molecular weight phenolics with proteins (BSA). Journal of Food Science, 65, 617–621.
7. Bohin, M.C., Vincken, J.P., van der Hijden, H.T.W.M. & Gruppen, H. (2012). Efficacy of food proteins as carriers for flavonoids. Journal of Agricultural and Food Chemistry, 60, 4136–4143.
8. Bose, A. (2016). Interaction of tea polyphenols with serum albumins: a fluorescence spectroscopic analysis. Journal of Luminescence, 169, 220–226.
9. Canon, F., Paté, F., Meudec, E. et al. (2009). Characterization, stoichiometry, and stability of salivary protein-tannin complexes by ESI-MS and ESI-MS/MS. Analytical and Bioanalytical Chemistry, 395, 2535–2545.
10. Cao, G., Sofic, E. & Prior, R.L. (1996). Antioxidant capacity of tea and common vegetables. Journal of Agricultural and Food Chemistry, 44, 3426–3431.
11. Crozier, A., Jaganath, I.B. & Clifford, M.N. (2009). Dietary phenolics: chemistry, bioavailability and effects on health. Natural Product Reports, 26, 1001–1043.
12. Czubinski, J., Dwiecki, K., Siger, A. et al. (2012). Release of flavonoids from lupin globulin proteins during digestion in a model system. Journal of Agricultural and Food Chemistry, 60, 1830–1836.
13. Czubinski, J., Dwiecki, K., Siger, A., Neunert, G. & Lampart-Szczapa, E. (2014). Characterisation of different digestion susceptibility of lupin seed globulins. Food Chemistry, 143, 418–426.
14. Duarte, G.S. & Farah, A. (2011). Effect of simultaneous consumption of milk and coffee on CGAs' bioavailability in humans. Journal of Agricultural and Food Chemistry, 59, 7925–7931.
15. Dubeau, S., Samson, G. & Tajmir-Riahi, H.A. (2010). Dual effect of milk on the antioxidant capacity of green, Darjeeling and English breakfast teas. Food Chemistry, 122, 539–545.
16. Dwiecki, K., Siger, A., Czubinski, J., Nogala-Kałucka, M. & Lampart-Szczapa, E. (2012). The interactions between rapeseed lipoxygenase and native polyphenolic compounds in a model system. Journal of the American Oil Chemists' Society, 89, 379–387.
17. Friedman, M. & Jürgens, H.S. (2000). Effect of pH on the stability of plant phenolic compounds. Journal of Agricultural and Food Chemistry, 48, 2101–2110.
18. Gonzales, G.B., Smagghe, G., Grootaert, Ch, Zotti, M., Raes, K. & Van Camp, J. (2015). Flavonoid interactions during digestion, absorption, distribution and metabolism: a sequential structure-activity/property relationship-based approach in the study of bioavailability and bioactivity. Drug Metabolism Reviews, 47, 175–190.
19. He, Z., Chen, J. & Moser, S.E. (2015). Interaction of β-lactoglobulin with (−)-epigallocatechin-3-gallate under different processing conditions of pH and temperature by the fluorescence quenching method. European Food Research Technology, 241, 357–366.
20. Ishii, T., Mori, T., Tanaka, T. et al. (2008). Covalent modification of proteins by green tea polyphenol (–)-epigallocatechin-3-gallate through autoxidation. Free Radical Biology and Medicine, 45, 1384–1394.
21. Jakobek, L. (2015). Interactions of polyphenols with carbohydrates, lipids and proteins. Food Chemistry, 175, 556–567.
22. Kanakis, C.D., Hasni, I., Bourassa, P., Tarantilis, P.A., Polissiou, M.G. & Tajmir-Riahi, H.-A. (2011). Milk β-lactoglobulin complexes with tea polyphenols. Food Chemistry, 127, 1046–1055.
23. Keppler, J.K., Martin, D., Garamus, V.M. & Schwarz, K. (2015). Differences in binding behavior of (-)-epigallocatechin gallate to β-lactoglobulin heterodimers (AB) compared to homodimers (A) and (B). Journal of Molecular Recognition, 28, 656–666.
24. Kroll, J., Rawel, H.M. & Rohn, S. (2003). Reactions of plant phenolics with food proteins and enzymes under special consideration of covalent bonds. Food Science and Technology Research, 9, 205–218.
25. Lampart-Szczapa, E., Siger, A., Trojanowska, K., Nogala-Kałucka, M., Małecka, M. & Pachołek, B. (2003). Chemical composition and antibacterial activities of lupin seeds extracts. Nahrung/Food, 47, 286–290.
26. Le Bourvellec, C. & Renard, C.M.G.C. (2012). Interactions between polyphenols and macromolecules: quantification methods and mechanisms. Critical Reviews in Food Science and Nutrition, 52, 213–248.
27. Lefort, E.C. & Blay, J. (2013). Apigenin and its impact on gastrointestinal cancers. Molecular Nutrition and Food Research, 57, 126–144.
28. Liu, R.H. (2004). Potential synergy of phytochemicals in cancer prevention: mechanism of action. Journal of Nutrition, 134, 3479–3485.
29. Liu, E.H., Qi, L.W. & Li, P. (2010). Structural relationship and binding mechanisms of five flavonoids with bovine serum albumin. Molecules, 15, 9092–9103.
30. Liu, F., Wang, D., Ma, C. & Gao, Y. (2016). Conjugation of polyphenols prevents lactoferrin from thermal aggregation at neutral pH. Food Hydrocolloids, 58, 49–59.
31. Liu, F., Ma, C., McClements, D.J. & Gao, Y. (2017). A comparative study of covalent and non-covalent interactions between zein and polyphenols in ethanol-water solution. Food Hydrocolloids, 63, 625–634.
32. Martini, S., Claudia, B. & Claudio, R. (2008). Interaction of quercetin and its conjugate quercetin 3-O-β-D-glucopyranoside with albumin as determined by NMR relaxation data. Journal of Natural Products, 71, 175–178.
33. Masqsood, S., Benjakul, S., Abushelaidi, A. & Alam, A. (2014). Phenolic compounds and plant phenolic extracts as natural antioxidants in prevention of lipid oxidation in seafood: a detailed review. Comprehensive Reviews in Food Science and Food Safety, 13, 1125–1140.
34. Mekoue Nguela, J., Poncet-Legrand, C., Sieczkowski, N. & Vernhet, A. (2016). Interactions of grape tannins and wine polyphenols with a yeast protein extract, mannoproteins and β-glucan. Food Chemistry, 210, 671–682.
35. Nagy, K., Courtet-Compondu, M.-C., Williamson, G., Rezzi, S., Kussmann, M. & Rytz, A. (2012). Non-covalent binding of proteins to polyphenols correlates with their amino acid sequence. Food Chemistry, 132, 1333–1339.
36. O'Connell, J.E. & Fox, P.F. (1999). Proposed mechanism for the effect of polyphenols on the heat stability of milk. International Dairy Journal, 9, 523–536.
37. Ognjenovic, J., Stojadinovic, M., Milcic, M. et al. (2014). Interactions of epigallo-catechin 3-gallate and ovalbumin, the major allergen of egg white. Food Chemistry, 164, 36–43.
38. Ojha, H., Mishra, K., Hassan, M.I. & Chaudhury, N.K. (2012). Spectroscopic and isothermal titration calorimetry studies of binding interaction of ferulic acid with biovine serum albumin. Thermochimica Acta, 548, 56–64.
39. Ozdal, T., Capanoglu, E. & Altay, F. (2013). A review on protein-phenolic interactions and associated changes. Food Research International, 51, 954–970.
40. Pal, S., Dey, S.K. & Saha, C. (2014). Inhibition of catalase by tea catechins in free and cellular state: a biophysical approach. PLoS ONE, 9, e102460.
41. Prigent, S.V.E., Gruppen, H., Visser, A.J.W.G., Van Koningsveld, G.A. & Alfons, G.J.V. (2003). Effects of non-covalent interactions with 5-o-caffeoylquinic acid (CGA) on the heat denaturation and solubility of globular proteins. Journal of Agricultural and Food Chemistry, 51, 5088–5095.
42. Prigent, S.V., Voragen, A.G., Visser, A.J., van Koningsveld, G.A. & Gruppen, H. (2007). Covalent interactions between proteins and oxidation products of caffeoylquinic acid (chlorogenic acid). Journal of the Science of Food and Agriculture, 87, 2502–2510.
43. Prigent, S.V.E., Voragen, A.G.J., Van Koningsveld, G.A., Baron, A., Renard, C.M.G.J. & Gruppen, H. (2009). Interactions between globular proteins and procyanidins of different degrees of polymerization. Journal of Dairy Science, 92, 5843–5853.
44. Quintero-Flórez, A., Sánchez-Ortiz, A., Gaforio Martínez, J.J., Jiménez Márquez, A. & Beltrán Maza, G. (2015). Interaction between extra virgin olive oil phenolic compounds and mucin. European Journal of Lipid Science and Technology, 117, 1569–1577.
45. Rawel, H.M., Czajka, D., Rohn, S. & Kroll, J. (2002a). Interactions of different phenolic acids and flavonoids with soy proteins. International Journal of Biological Macromolecules, 30, 137–150.
46. Rawel, H.M., Rohn, S., Kruse, H.P. & Kroll, J. (2002b). Structural changes induced in bovine serum albumin by covalent attachment of chlorogenic amid. Food Chemistry, 78, 443–455.
47. Reddy, V.C., Sagar, G.V.V., Sreeramulu, D., Venu, L. & Raghunath, M. (2005). Addition of milk does not alter the antioxidant activity of black tea. Annals of Nutrition and Metabolism, 49, 189–195.
48. Rohn, S., Rawel, H.M., Röber, M. & Kroll, J. (2005). Reactions with phenolic substances can induce changes in some physico-chemical properties and activities of bromelain – the consequences for supplementary food products. International Journal of Food Science and Technology, 40, 771–782.
49. Ross, L., Barclay, C. & Vinqvist, M.R. (2003). Phenols as antioxidants. In: The Chemistry of Phenols. (edited by Z. Rappoport). Pp. 839–908 Chichester, UK: John Wiley & Sons.
50. Roura, E., Andres-Lacueva, C., Estruch, R. et al. (2007). Milk does not affect the bioavailability of cocoa powder flavonoid in healthy human. Annals of Nutrition and Metabolism, 51, 493–498.
51. Roy, A.S., Utreja, J. & Badhei, S. (2015). Characterization of the binding of fisetin and morin with chicken egg lysozyme using spectroscopic and molecular docking methods. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 81, 385–394.
52. Scafuri, B., Marabotti, A., Carbone, V., Minasi, P., Dotolo, S. & Facchiano, A. (2016). A theoretical study on predicted protein targets of apple polyphenols and possible echanisms of chemoprevention in colorectal cancer. Scientific Reports, 6, 1–13.
53. Shahidi, F., McDonald, J., Chandrasekara, A. & Zhong, Y. (2008). Phytochemicals of food, beverages and fruit vinegars: chemistry and health effects. Asia Pacific Journal of Clinical Nutrition, 17, 380–382.
54. Shen, F., Niu, F., Li, J., Su, Y., Liu, Y. & Yang, Y. (2014). Interactions between tea polyphenol and two kinds of typical egg white proteins-ovalbumin and lysozyme: effect on the gastrointestinal digestion of both proteins in vitro. Food Research International, 59, 100–107.
55. Shpigelman, A., Shoham, Y., Israeli-Lev, G. & Livney, Y.D. (2014). β-Lactoglobulin–naringenin complexes: nano-vehicles for the delivery of a hydrophobic nutraceutical. Food Hydrocolloids, 40, 214–224.
56. Stojadinovic, M., Radosavljevic, J., Ognjenovic, J. et al. (2013). Binding affinity between dietary polyphenols and beta-lactoglobulin negatively correlates with the protein susceptibility to digestion and total antioxidant activity of complexes formed. Food Chemistry, 136, 1263–1271.
57. Sun, L., Chen, W., Meng, Y., Yang, X., Yuan, L. & Guo, Y. (2016). Interactions between polyphenols in thinned young apples and porcine pancreatic α-amylase: inhibition, detailed kinetics and fluorescence quenching. Food Chemistry, 208, 51–60.
58. Thongkaew, C., Gibis, M., Hinrichs, J. & Weiss, J. (2014). Polyphenol interactions with whey protein isolate and whey protein isolate-pectin coacervates. Food Hydrocolloids, 41, 103–112.
59. Tomás-Barberán, F.A. & Andrés-Lacueva, C. (2012). Polyphenols and health: current state and progress. Journal of Agricultural and Food Chemistry, 60, 8773–8775.
60. Trombley, J.D., Loegel, T.N., Danielson, N.D. & Hagerman, A.E. (2011). Capillary electrophoresis methods for the determination of covalent polyphenol-protein complexes. Analytical and Bioanalytical Chemistry, 401, 1523–1529.
61. Tungjai, M., Poompimon, W., Loetchutinat, C., Kothan, S., Dechsupa, N. & Mankhetkorn, S. (2008). Spectrophotometric characterization of behavior and the predominant species of flavonoids in physiological buffer: determination of solubility, lipophilicity and anticancer efficacy. Open Drug Delivery Journal, 2, 10–19.
62. Vesic, J., Stambolic, I., Apostolovic, D., Milcic, M., Stanic-Vucinic, D. & Cirkovic Velickovic, T. (2015). Complexes of green tea polyphenol, epigalocatechin-3-gallate, and 2S albumins of peanut. Food Chemistry, 185, 309–317.
63. Wang, S.H., Liu, F.F., Dong, X.Y. & Sun, Y. (2012). Calorimetric and spectroscopic studies of the interactions between insulin and (-)-epigallocatechin-3-gallate. Biochemical Engineering Journal, 62, 70–78.
64. Wobst, H.J., Sharma, A., Diamond, M.I., Wanker, E.E. & Bieschke, J. (2015). The green tea polyphenol (-)-epigallocatechin gallate prevents the aggregation of tau protein into toxic oligomers at substoichiometric ratios. FEBS Letters, 589, 77–83.
65. Wu, X., He, W., Yao, L. et al. (2013). Characterization of binding interactions of (-)-epigallocatechin-3-gallate from green tea and lipase. Journal of Agricultural and Food Chemistry, 61, 8829–8835.
66. Xiao, J., Mao, F., Yang, F., Zhao, Y., Zhang, C. & Yamamoto, K. (2011). Interaction of dietary polyphenols with bovine milk proteins: molecular structure-affinity relationship and influencing bioactivity aspects. Molecular Nutrition and Food Research, 55, 1637–1645.
67. Zhao, Y.Y., Chen, L.J., Han, L.J. et al. (2013). Molecular and thermodynamic basis for EGCG-keratin interactionpart II: experimental investigation. AICHE Journal, 59, 4824–4827.