A critical review of the characterization of polyphenol–protein interactions and of their potential use for improving food quality

Current Pharmaceutical Design

Volumn 23, Issue 19, 2017, Pages 2742-2753

  Perez Gregorio, Maria Rosa ^a   Simal Gándara, Jesús ^b  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSITY OF VIGO   (Spain)

Author keywords

Anti nutritional effects; Antiaging properties; Characterization of polyphenol; Food quality; Phenolic compounds; Polyphenol; Protein interactions

Indexed keywords

ADVANCED GLYCATION END PRODUCT; POLYPHENOL; PROTEIN; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; PLANT PROTEIN; PROTEIN BINDING;

ANTIAGING ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; BINDING KINETICS; BINDING SITE; CAPILLARY ELECTROPHORESIS; CHEMICAL COMPOSITION; CHEMICAL MODIFICATION; CIRCULAR DICHROISM; COLOR; COMPUTER ANALYSIS; DRUG ACTIVITY; ELECTROSPRAY MASS SPECTROMETRY; FLAVOR; FLUORESCENCE QUENCHING; FLUORESCENCE SPECTROSCOPY; FOOD COMPOSITION; FOOD INTAKE; FOOD PROCESSING; FOOD QUALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTHERMAL TITRATION CALORIMETRY; NEUTRON SCATTERING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUTRITIONAL ASSESSMENT; PHOTON CORRELATION SPECTROSCOPY; POLYPHENOL PROTEIN INTERACTION; PRIORITY JOURNAL; PROTEIN INTERACTION; REVIEW; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY; ANIMAL; HUMAN; METABOLISM; NUCLEAR MAGNETIC RESONANCE; PHYSIOLOGY; PROCEDURES;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTIOXIDANTS; FOOD QUALITY; HUMANS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; POLYPHENOLS; PROTEIN BINDING; VEGETABLE PROTEINS;

EID: 85027881231     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/1381612823666170202112530     Document Type: Review

References (127)

1. Trombley JD, Loegel TN, Danielson ND, Hagerman AE. Capillary electrophoresis methods for the determination of covalent polyphenol-protein complexes. Anal Bioanal Chem 2011; 401(5): 1527-33.
2. Ferrer-Gallego R, Soares S, Mateus N, Rivas-Gonzalo J, Escribano-Bailón MT, De Freitas V. New Anthocyanin-Human Salivary Protein Complexes. Langmuir 2015; 31(30): 8392-401.
3. Dias R, Perez-Gregorio MR, Mateus N, De Freitas V. Interaction study between wheat-derived peptides and procyanidin B3 by mass spectrometry. Food Chem 2016; 194: 1304-12.
4. Perez-Gregorio MR, Mateus N, De Freitas V. New procyanidin B3-human salivary protein complexes by mass spectrometry. Effect of salivary protein profile, tannin concentration, and time stability. J Agri Food Chem 2014; 62(41): 10038-45.
5. Perez-Gregorio MR, Mateus N, De Freitas V. Rapid screening and identification of new soluble tannin-salivary protein aggregates in saliva by mass spectrometry (MALDI-TOF-TOF and FIA-ESI-MS). Langmuir 2014; 30(28): 8528-37.
6. Quijada-Morín N, Crespo-Expósito C, Rivas-Gonzalo JC, García-Estévez I, Escribano-Bailón MT. Effect of the addition of flavan-3- ols on the HPLC-DAD salivary-protein profile. Food Chem 2016; 207: 272-8.
7. Ferrer-Gallego R, Gonçalves R, Rivas-Gonzalo JC, Escribano-Bailón MT, De Freitas V. Interaction of phenolic compounds with bovine serum albumin (BSA) and α-amylase and their relationship to astringency perception. Food Chem 2012; 135(2): 651-8.
8. Lu Q, Chen C, Zhao S, Ge F, Liu D. Investigation of the Interaction Between Gallic Acid and α-Amylase by Spectroscopy. Int J Food Prop 2016; 19(11): 2481-94.
9. Cala O, Dufourc EJ, Fouquet E, Manigand C, Laguerre M, Pianet I. The colloidal state of tannins impacts the nature of their interaction with proteins: The case of salivary proline-rich pro-tein/procyanidins binding. Langmuir 2012; 28(50): 17410-8.
10. Lorenz K, Preston CM. Characterization of high-tannin fractions from humus by carbon-13 cross-polarization and magic-angle spinning nuclear magnetic resonance. J Env Qual 2002; 31(2): 431-6.
11. Yanamala N, Tirupula KC, Balem F, Klein-Seetharaman J. pH-dependent interaction of rhodopsin with cyanidin-3-glucoside. 1. Structural aspects. Photochem Photobiol 2009; 85(2): 454-62.
12. Dias R, Perez-Gregorio R, Mateus N, De Freitas V. The interaction between tannins and gliadin derived peptides in a celiac disease perspective. RSC Adv 2015; 5(41): 32151-8.
13. Pascal C, Poncet-Legrand C, Cabane B, Vernhet A. Aggregation of a proline-rich protein induced by epigallocatechin gallate and condensed tannins: Effect of protein glycosylation. J Agri Food Chem 2008; 56(15): 6724-32.
14. Mateus N, Carvalho E, Luís C, De Freitas V. Influence of the tannin structure on the disruption effect of carbohydrates on protein-tannin aggregates. Anal Chim Acta 2004; 513(1): 135-40.
15. McRae JM, Ziora ZM, Kassara S, Cooper MA, Smith PA. Ethanol concentration influences the mechanisms of wine tannin interactions with poly(l -proline) in model wine. J Agri Food Chem 2015; 63(17): 4345-52.
16. Zwahlen C, Pascale Legault, Sébastien JF, Vincent JG, Robert K, Lewis EK. Methods for Measurement of Intermolecular NOEs by Multinuclear NMR Spectroscopy: Application to a Bacteriophage λ N-Peptide/boxB RNA Complex. J Am Chem Soc 1997.
17. Richard T, Lefeuvre D, Descendit A, Quideau S, Monti JP. Recognition characters in peptide–polyphenol complex formation. Biochim Biophys Acta (BBA) - General Subjects 2006; 1760(6): 951-8.
18. Dias R, Perez-Gregorio MR, Mateus N, De Freitas V. Interaction study between wheat-derived peptides and procyanidin B3 by mass spectrometry. Food Chem 2016; 194: 1304-12.
19. Canon F, Paté F, Cheynier V, et al. Aggregation of the salivary proline-rich protein IB5 in the presence of the tannin EgCG. Langmuir 2013; 29(6): 1926-37.
20. Budryn G, Zaczyńska D, Pałecz B, et al. Interactions of free and encapsulated hydroxycinnamic acids from green coffee with egg ovalbumin, whey and soy protein hydrolysates. LWT - Food Sci Technol 2016; 65: 823-31.
21. Veenstra TD. "Electrospray ionization mass spectrometry in the study of biomolecular non-covalent interactions". Biophys Chem 1999; 79: 63-79.
22. Soares S, Mateus N, de Freitas V. Interaction of Different Polyphenols with Bovine Serum Albumin (BSA) and Human Salivary α-Amylase (HSA) by Fluorescence Quenching. J Agric Food Chem 2007; 55(16): 6726-35.
23. Dias R, Perez-Gregorio R, Mateus N, De Freitas V. The interaction between tannins and gliadin derived peptides in a celiac disease perspective. RSC Adv 2015; 5(41): 32151-8.
24. Soares S, Nuno Mateus, Victor de Freitas. Interaction of Different Polyphenols with Bovine Serum Albumin (BSA) and Human Salivary α-Amylase (HSA) by Fluorescence Quenching. J Agric Food Chem 2007.
25. Ulrih NP. Analytical Techniques for the Study of Polyphenol– protein Interactions. Crit Rev Food Sci Nutr 2015; 55: 2144-61.
26. Schindler CEM, de Vries SJ, Sasse A, Zacharias M. SAXS Data Alone can Generate High-Quality Models of Protein-Protein Complexes. Structure 2016; 24(8): 1387-97.
27. Li M, Hagerman AE. Role of the flavan-3-ol and galloyl moieties in the interaction of (-)-epigallocatechin gallate with serum albumin. J Agri Food Chem 2014; 62(17): 3768-75.
28. Nozaki A, Kimura T, Ito H, Hatano T. Interaction of Polyphenolic Metabolites with Human Serum Albumin: A Circular Dichroism Study. Chem Pharm Bulletin 2009; 57(9): 1019-23.
29. Ferrer-Gallego R, Brás NF, García-Estévez I, et al. Effect of flavonols on wine astringency and their interaction with human saliva. Food Chem 2016; 209: 358-64.
30. Ferrer-Gallego R, Quijada-Morín N, Brás NF, et al. Characterization of sensory properties of flavanols-A molecular dynamic approach. Chem Sens 2015; 40(6): 381-90.
31. Drynan JW, Clifford MN, Obuchowicz J, Kuhnert N. The chemistry of low molecular weight black tea polyphenols. Nat Prod Rep 2010; 27(3): 45.
32. Hagerman AE, Robbins CT. Implications of soluble-tannins protein complexes for tannin analysis and plant defense mechanism. J Chem Ecol 1987; 13(5): 1243-59.
33. Artz WE, Bishop PD, Dunker AK, Schanus E, Swanson BG. Interaction of synthetic proanthocyanidin dimers and trimers with bovine serum albumin and purified bean globulin fraction G-1. J Agric Food Chem 1987; 35(3): 417-21.
34. Haslam E, Cai Y. Plant polyphenols (Vegetable tannins): Gallic acid metabolism. Nat Prod Rep 1994; 11: 41-66.
35. Loomis WD. Overcoming problems of phenolics and quinones in the isolation of plant enzymes and organelles. Methods Enzymol 1974; 31: 528-44.
36. Oh HI, Hoff JE, GS A, LA. H. Hydrophobic interactions in tannin-protein complexes. J Agri Food Chem 1980; 28(394).
37. Brudzynski KM-Á, L. Polyphenol-protein complexes and their consequences for the redox activity, structure and function of honey. A current view and new hypothesis – a review. Pol J Food Nutr Sci 2015; 65(2): 9.
38. NJ M, MP W, TH L, E H. Study of the interaction between proline-rich proteins and a polyphenol by IH NMR Spectroscopy. Eur J Biochem 1994; 219(3): 923-35.
39. Haslam E, MP W, NJ B, AJ. C. Astringency and polyphenol protein interactions. Recent Adv Phytochem 1999; 33: 289-318.
40. Hagerman AE, Butler LG. The Specificity of Proanthocyanidin-Protein Interactions. J Biol Chem 1981; 256(9): 3.
41. Siebert KJ, Troukhanova NV, Lynn PY. Nature of Polyphenol-Protein Interactions. J Agric Food Chem 1996; 44: 5.
42. Prigent SVE, Gruppen H, Visser AJWG, Van Koningsveld GAHD, Alfons GJV. Effects of non-covalent interactions with 5-o-caffeoylquinic acid (CGA) on the heat denaturation and solubility of globular proteins. J Agric Food Chem 2003; 51: 7.
43. 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: 4.
44. Ozdal T, Capanoglu E, Altay F. A review on protein-phenolic interactions and associated changes. Food Res Int 2013; 51(2): 954-70.
45. Dubeau S, Samson G, Tajmir-Riahi HA. Dual effect of milk on the antioxidant capacity of green, Darjeeling, and English breakfast teas. Food Chem 2010; 122: 6.
46. Bartolome B. ElaHM. Interaction of low molecular weight Phenolics with protein (BSA). J Food Sci 2000; 65(4): 617-21.
47. Martini S, Claudia B, Claudio R. Interaction of quercetin and its conjugate quercetin 3-o-β-D-glucopyranoside with albumin as determined by NMR relaxation data. J Nat Prod 2008; 71: 3.
48. Tsai P, She C. Significance of phenol–protein interactions in modifying the antioxidant capacity of peas. J Agric Food Chem 2006; 54: 3.
49. Xiao J, Mao F, Yang F, Zhao Y, Zhang C, Yamamoto K. Interaction of dietary polyphenols with bovine milk proteins: molecular structure–affinity relationship and influencing bioactivity aspects. Mol Nut Food Res 2011; 55: 8.
50. Lesschaeve IN, A.C. Polyphenols: factors influencing their sensory properties and their effects on food and beverage preferences. Am J Clin Nutr 2005; 81: 5.
51. Brouillard R, Delaporte B. Chemistry of anthocyanin pigments. 2. Kinetic and thermodynamic study of proton transfer, hydration, and tautomeric reactions of malvidin 3-glucoside. J Am Chem Soc 1977; 99(26): 8461-8.
52. Brouillard R, Dubois JE. Mechanism of the structural transformations of anthocyanins in acidic media. J Am Chem Soc 1977; 99(5): 1359-64.
53. Brouillard R DO. Flavonoids and flower colour. In: Harborne JB, ed. The flavonoids: advances in research since 1986. London: Chapman and Hall 1993: 22.
54. Atanosova V FH, Le Guerenevé C, Dangles O, Cheynier V. First evidence of acetaldehyde-induced anthocyanin polymerisation.In: Hadrami I, ed Polyphenol communications 2002 Marrakech 2002.
55. Atanasova V, Fulcrand H, Cheynier V, Moutounet M. Effect of oxygenation on polyphenol changes occurring in the course of wine-making. Anal Chim Acta 2002; 458(1): 15-27.
56. Remy-Tanneau S, Le Guernevié C, Meudec E, Cheynier V. Characterization of a colorless anthocyanin-flavan-3-ol dimer containing both carbon-carbon and ether interflavanoid linkages by NMR and mass spectrometry. J Agr Food Chem 2003; 51(12): 3592-7.
57. Sastry MCSRMSM. Binding of chlorogenic acid by the isolated polyphenol-free 11S protein of sunflower (Helianthus annuus) seed. J Agri Food Chem 1990; 38(12): 2103-110.
58. Arroyo-Maya IJ, Campos-Terán J, Hernández-Arana A, McClements DJ. Characterization of flavonoid-protein interactions using fluorescence spectroscopy: Binding of pelargonidin to dairy proteins. Food Chem 2016; 213: 431-9.
59. Chung C, Rojanasasithara T, Mutilangi W, McClements DJ. Stability improvement of natural food colors: Impact of amino acid and peptide addition on anthocyanin stability in model beverages. Food Chem 2017; 218: 277-84.
60. Utrera MM, Ganhao R, Estevez M. Role of Phenolics Extracting from Rosa canina L. on Meat Protein Oxidation During Frozen Storage and Beef Patties Processing. Food Bioprocess Technol 2015; 8: 10.
61. Suppavorasatit I, Cadwallader KR. Flavor-Soy Protein Interactions. Chemistry, Texture, and Flavor of Soy. ACS Symposium Series. 1059: Am Chem Soc; 2010. p. 339-59.
62. Bandyopadhyay P, Ghosh AK, Ghosh C. Recent developments on polyphenol-protein interactions: effects on tea and coffee taste, antioxidant properties and the digestive system. Food Funct 2012; 3(6): 592-605.
63. Hufnagel JC, Hofmann T. Orosensory-Directed Identification of Astringent Mouthfeel and Bitter-Tasting Compounds in Red Wine. J Agr Food Chem 2008; 56(4): 1376-86.
64. Guerreiro JRL, Sutherland DS, De Freitas V, Sales MGF. Protein– polyphenol interaction on silica beads for astringency tests based on eye, photography or reflectance detection modes. Anal Meth 2013; 5: 9.
65. Guyot S, Pellerin P, Brillouet JM, VC. Inhibition of β-glucosidase (Amygdalae dulces) by (+)-catechin oxidation products and procyanidin dimers. Biosci Biotech Biochem 1996; 60: 4.
66. Somers TC. The polymeric nature of wine pigments. Phytochem 1971; 10: 9.
67. Cheynier V. Polyphenols in foods are more complex than often thought. Am J Cli Nut 2005; 81(1): 223S-9S.
68. Martínez-Las Heras R, Pinazo A, Heredia A, Andrés A. Evaluation studies of persimmon plant (Diospyros kaki) for physiological benefits and bioaccessibility of antioxidants by in vitro simulated gastrointestinal digestion. Food Chem 2017; 214: 478-85.
69. Jansman AJM. Tannins in feedstuffs for simple stomached animals. Nutr Res Rev 1993; 6(1): 209-36.
70. Milic B, Stojanovic S, Vucureuic N, Turcic M. Chlorogenic and quinic acids in sunflower meal. J Sci Food Agric 1968; 19: 108-113.
71. Manach CSA, Morand C, Remesy C, Jimenez L. Polyphenols: Food sources and bioavailability. Am J Clin Nutr 2004; 79: 20.
72. Sazuka MIT, Suzuki Y. Odani S, Koide T, Isemura M. Evidence for the interaction between (−)-epigallocatechin gallate and human plasma proteins fibronectin, fibrinogen, and histidine-rich glycoprotein. Biosci Biotechnol Biochem 1996; 60: 2.
73. Da Silva JMR, Darmon N, Fernandez Y, Mitjavila S. Oxygen free radical scavenger capacity in aqueous models of different procya-nidins from grape seeds. J Agr Food Chem 1991; 39(9): 1549-52.
74. Plumb GW, De Pascual-Teresa S, Santos-Buelga C, Cheynier V, Williamson G. Antioxidant properties of catechins and proanthocyanidins: Effect of polymerisation, galloylation and glycosylation. Free Rad Res 1998; 29(4): 351-8.
75. Gómez-Guillén MC, Montero MP. Polyphenol uses in seafood conservation. Am J Food Techn 2007; 2(7): 593-601.
76. Medina I, Cascante M, Torres JL, Pazos M. Natural bioactive antioxidants for the enrichment of seafood. ACS Symposium Series 2008. p 192-8.
77. Manach C, Scalbert A, Morand C, Rémésy C, Jiménez L. Polyphenols: food sources and bioavailability. Am J Clin Nut 2004; 79(5): 727-47.
78. Sazuka M, Itoi T, Suzuki Y, Odani S, Koide T, Isemura M. Evidence for the interaction between (−)-epigallocatechin gallate and human plasma proteins fibronectin, fibrinogen, and histidine-rich glycoprotein. Biosci Biotechn Biochem 1996; 60(8): 1317-9.
79. Tsai P-J, She C-H. Significance of phenol-protein interactions in modifying the antioxidant capacity of peas. J Agr Food Chem 2006; 54(22): 8491-4.
80. Asquith TN, Butler LG. Interactions of condensed tannins with selected proteins. Phytochem 1986; 25(7): 1591-3.
81. Riedl KM, Hagerman AE. Tannin−Protein Complexes as Radical Scavengers and Radical Sinks. J Agr Food Chem 2001; 49(10): 4917-23.
82. Poulsen MW, Hedegaard RV, Andersen JM, et al. Advanced glyca-tion endproducts in food and their effects on health. Food Chem Toxicol 2013; 60: 10-37.
83. Culetu A, Fernandez-Gomez B, Ullate M, del Castillo MD, And-lauer W. Effect of theanine and polyphenols enriched fractions from decaffeinated tea dust on the formation of Maillard reaction products and sensory attributes of breads. Food Chem 2016; 197: 14-23.
84. Bordenave N, Hamaker BR, Ferruzzi MG. Nature and consequences of non-covalent interactions between flavonoids and macronutrients in foods. Food Funct 2014; 5(1): 18-34.
85. Yan Y, Hu J, Yao P. Effects of Casein, Ovalbumin, and Dextran on the Astringency of Tea Polyphenols Determined by Quartz Crystal Microbalance with Dissipation. Langmuir 2009; 25(1): 397-402.
86. Lorenz M, Jochmann N, von Krosigk A, et al. Addition of milk prevents vascular protective effects of tea. Europ Heart J 2007; 28(2): 219.
87. Keogh JB, McInerney J, Clifton PM. The Effect of Milk Protein on the Bioavailability of Cocoa Polyphenols. J Food Sci 2007; 72(3): S230-S3.
88. Egert S, Tereszczuk J, Wein S, et al. Simultaneous ingestion of dietary proteins reduces the bioavailability of galloylated catechins from green tea in humans. Europ J Nutr 2013; 52(1): 281-8.
89. Wang Q LY, Sun F, Li X, et al. Tannins improve dough mixing properties through affecting physicochemical and structural properties of wheat gluten proteins. Food Res Int 2015; 69: 7.
90. Wu W, Clifford M, Howell NK. The effect of instant green tea on the foaming and rheological properties of egg albumen proteins. J Sci Food Agr 2007; 87(10): 1810-9.
91. Han J, Britten M, St-Gelais D, et al. Effect of polyphenolic ingredients on physical characteristics of cheese. Food Res Int 2011; 44(1): 494-7.
92. Vega C, Grover MK. Physicochemical Properties of Acidified Skim Milk Gels Containing Cocoa Flavanols. J Agr Food Chem 2011; 59(12): 6740-7.
93. Zanchi D, Narayanan T, Hagenmuller D, et al. Tannin-assisted aggregation of natively unfolded proteins. EPL (Europhysics Let-ters) 2008; 82(5): 58001.
94. Beveridge T, Wrolstad RE. Haze and cloud in apple juices. Crit Rev Food Sci 1997; 37(1): 75-91.
95. Esteruelas M, Kontoudakis N, Gil M, Fort MF, Canals JM, Zamora F. Phenolic compounds present in natural haze protein of Sauvignon white wine. Food Res Int 2011; 44(1): 77-83.
96. Linforth RST, Westwood K, Somani A, Doherty N, Cook DJ. Hop proanthocyanidins for the fining of beer. J Inst Brew 2015; 121(4): 490-5.
97. Asano KS, K, Hashimoto N. Characterization of haze-forming proteins of beer and their roles in chill haze formation. J Am Soc Brew Chem 1982; 40: 7.
98. McMurrough I, Hennigan GP, Loughrey MJ. Contents of simple, polymeric and complexed flavanols in worts and beers and their relationship to haze formation. J Inst Brew 1983; 89(1): 15-23.
99. Ferruzzi MG, Bordenave N, Hamaker BR. Does flavour impact function? Potential consequences of polyphenol–protein interactions in delivery and bioactivity of flavan-3-ols from foods. Physiol Behav 2012; 107: 6.
100. Rhodes BJRaMJC. Binding affinity of hydrolyzable tannins to parotid saliva and to proline-rich proteins derived from it. J Agric Food Chem 2000; 48: 5.
101. De Freitas V, Mateus N. Protein/Polyphenol Interactions: Past and Present Contributions. Mechanisms of Astringency Perception. Curr Org Chem 2012; 16: 22.
102. Boath AS, Grussu D, Stewart D, McDougall GJ. Berry Polyphenols Inhibit Digestive Enzymes: a Source of Potential Health Benefits? Food Digest 2012; 3(1): 1-7.
103. Ananingsih VK, Sharma A, Zhou W. Green tea catechins during food processing and storage: A review on stability and detection. Food Res Int 2013; 50(2): 469-79.
104. Bae MJ, TI K, Minoda Y, et al. Albumin stabilizes (-)-epigallocatechin gallate in human serum: binding capacity and antioxidant property. Mol Nutr Food Res 2009; 53: 6.
105. Liu J, Wang Q, Zhang H, Yu D, Jin S, Ren F. Interaction of chlorogenic acid with milk proteins analyzed by spectroscopic and modeling methods. Spectr Letters 2016; 49(1): 44-50.
106. Arcan I, Yemenicioğlu A. Incorporating phenolic compounds opens a new perspective to use zein films as flexible bioactive packaging materials. Food Res Int 2011; 44(2): 550-6.
107. Fang JH, Zhang SH, Yu XM, Yang Y. Effects of quercetin and melatonin in pregnant and gestational diabetic women. Lat Am J Pharm 2016; 35(6): 1420-5.
108. Janet T, Taylor JRN, Belton PS, Amanda M. Kafirin microparticle encapsulation of catechin and sorghum condensed tannins. J Agr Food Chem 2009; 57(16): 7523-8.
109. Czubinski J, Dwiecki K, Siger A, et al. Release of Flavonoids from Lupin Globulin Proteins during Digestion in a Model System. J Agric Food Chem 2012; 60(7): 1830-6.
110. Shpigelman A, Cohen Y, Livney YD. Thermally-induced β-lactoglobulin-EGCG nanovehicles: Loading, stability, sensory and digestive-release study. Food Hydrocolloids 2012; 29(1): 57-67.
111. Arts MJTJ, Haenen GRMM, Wilms LC, et al. Interactions between flavonoids and proteins: Effect on the total antioxidant capacity. J Agr Food Chem 2002; 50(5): 1184-7.
112. Stojadinovic M, Radosavljevic J, Ognjenovic J, et al. Binding affinity between dietary polyphenols and β-lactoglobulin negatively correlates with the protein susceptibility to digestion and total antioxidant activity of complexes formed. Food Chem 2013; 136(3-4): 1263-71.
113. Almajano MP, Delgado ME, Gordon MH. Albumin causes a synergistic increase in the antioxidant activity of green tea catechins in oil-in-water emulsions. Food Chem 2007; 102(4): 1375-82.
114. Roopchand DE, Kuhn P, Rojo LE, Lila MA, Raskin I. Blueberry polyphenol-enriched soybean flour reduces hyperglycemia, body weight gain and serum cholesterol in mice. Pharmac Res 2013; 68(1): 59-67.
115. Grace MH, Guzman I, Roopchand DE, et al. Stable Binding of Alternative Protein-Enriched Food Matrices with Concentrated Cranberry Bioflavonoids for Functional Food Applications. J Agr Food Chem 2013; 61(28): 6856-64.
116. Gallo M, Vinci G, Graziani G, De Simone C, Ferranti P. The interaction of cocoa polyphenols with milk proteins studied by proteomic techniques. Food Res Int 2013; 54: 11.
117. Brudzynski KS, C.; Maldonado-Álvarez, L. A new look on protein-polyphenol complexation during honey storage: is this a random or organized event with the help of dirigent-like proteins? PLoS One 2013; 8(8): 8.
118. Canon F, Paté F, Cheynier V, et al. Aggregation of the Salivary Proline-Rich Protein IB5 in the Presence of the Tannin EgCG. Langmuir 2013; 29: 11.
119. Alonso-Díaz MA, Torres-Acosta JFJ, Sandoval-Castro CA, Capeti-llo-Leal CM. Amino acid profile of the protein from whole saliva of goats and sheep and its interaction with tannic acid and tannins extracted from the fodder of tropical plants. Small Rum Res 2012; 103: 5.
120. Cala O, Dufourc EJ, Fouquet E, Manigand C, Laguerre M, Pianet I. The Colloidal State of Tannins Impacts the Nature of Their Interaction with Proteins: The Case of Salivary Proline-Rich Pro-tein/Procyanidins Binding. Langmuir 2012; 28: 8.
121. Sun-Waterhouse D, Sivam AS, Cooney J, Zhou J, Perera CO, Waterhouse GIN. Effects of added fruit polyphenols and pectin on the properties of finished breads revealed by HPLC/LC-MS and Size-Exclusion HPLC. Food Res Int 2011; 44(9): 3047-56.
122. Ali M, Homann T, Kreisel J, et al. Characterization and Modeling of the Interactions between Coffee Storage Proteins and Phenolic Compounds. J Agric Food Chem 2012; 60: 7.
123. Schilling S, Sigolotto CI, Carle R, Schieber A. Characterization of covalent addition products of chlorogenic acid quinone with amino acid derivatives in model systems and apple juice by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun in Mass Spectrom 2008; 22(4): 441-8.
124. Harbertson JF, Yuan C, Mireles MS, Hanlin RL, Downey MO. Glucose, fructose and sucrose increase the solubility of protein-tannin complexes and at high concentration, glucose and sucrose interfere with bisulphite bleaching of wine pigments. Food Chem 2013; 138(1): 556-63.
125. Haratifar S, Corredig M. Interactions between tea catechins and casein micelles and their impact on renneting functionality. Food Chem 2014; 143: 5.
126. Taddei P, Zanna N, Tozzi S. Raman characterization of the interactions between gliadins and anthocyanins. J Raman Spectrosc 2013; 44(10): 1435-9.
127. Sarni-Manchado P, Cheynier V. Study of non-covalent complexation between catechin derivatives and peptides by electrospray ionization mass spectrometry. J Mass Spectrom 2002; 37(6): 609-16.