Binding affinity between dietary polyphenols and β-lactoglobulin negatively correlates with the protein susceptibility to digestion and total antioxidant activity of complexes formed

Food Chemistry

Volumn 136, Issue 3-4, 2013, Pages 1263-1271

  Stojadinovic, Marija ^a   Radosavljevic, Jelena ^a   Ognjenovic, Jana ^a   Vesic, Jelena ^a   Prodic, Ivana ^a   Stanic Vucinic, Dragana ^a   Cirkovic Velickovic, Tanja ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Lactoglobulin; Antioxidant; Digestion; Interaction; Polyphenol; Quenching

Indexed keywords

ACIDIC PH; ANTIOXIDANT; ANTIOXIDANT ACTIVITIES; BINDING AFFINITIES; BIOLOGICAL IMPLICATIONS; EFFECT OF PH; FLUORESCENCE AND CD SPECTROSCOPY; GASTRIC CONDITIONS; GASTROINTESTINAL TRACT; IN-VITRO; INTERACTION; LACTOGLOBULIN; NEUTRAL PH; NON-COVALENT INTERACTION; NONCOVALENT BINDING; PH VALUE; PHENOLIC ACIDS; POLYPHENOL EXTRACT; POLYPHENOLS; POSITIVE CORRELATIONS; PROTEIN DECAY; PROTEIN SECONDARY STRUCTURE; RADICAL SCAVENGING ACTIVITY; TOTAL ANTIOXIDANT CAPACITY;

AGENTS; BEVERAGES; BINDING ENERGY; BIOLOGICAL MATERIALS; CIRCULAR DICHROISM SPECTROSCOPY; ORGANIC ACIDS; PH; PHENOLS; QUENCHING; SLUDGE DIGESTION;

PROTEINS;

BETA LACTOGLOBULIN; PANCREATIN; PEPSIN A; POLYPHENOL DERIVATIVE;

ACIDITY; ALPHA HELIX; ANTIOXIDANT ACTIVITY; ARTICLE; BETA SHEET; BINDING AFFINITY; CIRCULAR DICHROISM; COVALENT BOND; DIGESTION; FLUORESCENCE SPECTROSCOPY; GASTROINTESTINAL TRACT; IN VITRO STUDY; ISOLATION AND PURIFICATION; LIQUID CHROMATOGRAPHY; MOLECULAR INTERACTION; PROTEIN SECONDARY STRUCTURE; STOMACH PH;

ANTIOXIDANTS; DIGESTION; GASTROINTESTINAL TRACT; HUMANS; HYDROGEN-ION CONCENTRATION; KINETICS; LACTOGLOBULINS; MODELS, BIOLOGICAL; POLYPHENOLS; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY;

THEOBROMA CACAO;

EID: 84867896149     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.09.040     Document Type: Article

References (48)

1. R. Amorati, and L. Valgimigli Modulation of the antioxidant activity of phenols by non-covalent interactions Organic & Biomolecular Chemistry 10 21 2012 4147 4158
2. M.J. Arts, G.R. Haenen, H.P. Voss, and A. Bast Masking of antioxidant capacity by the interaction of flavonoids with protein Food and Chemical Toxicology 39 8 2001 787 791 (Pubitemid 32575245)
3. M.J.T.J. Arts, G.R.M.M. Haenen, L.C. Wilms, S.A.J.N. Beetstra, C.G.M. Heijnen, and H.-P. Voss Interactions between flavonoids and proteins: Effect on the total antioxidant capacity Journal of Agricultural and Food Chemistry 50 5 2002 1184 1187 (Pubitemid 34194077)
4. N.F. Brás, R. Gonçalves, N. Mateus, P.A. Fernandes, M.J. Ramos, and V. de Freitas Inhibition of pancreatic elastase by polyphenolic compounds Journal of Agricultural and Food Chemistry 58 19 2010 10668 10676
5. C. Cabrera, R. Artacho, and R. Giménez Beneficial effects of green tea - A review Journal of the American College of Nutrition 25 2 2006 79 99 (Pubitemid 46939847)
6. M. Caruana, T. Hogen, J. Levin, A. Hillmer, A. Giese, and N. Vassallo Inhibition and disaggregation of alpha-synuclein oligomers by natural polyphenolic compounds FEBS Letters 585 8 2011 1113 1120
7. S. Chaudhuri, S. Chakraborty, and P.K. Sengupta Probing the interactions of hemoglobin with antioxidant flavonoids via fluorescence spectroscopy and molecular modeling studies Biophysical Chemistry 154 1 2011 26 34
8. S.-Y. Chung, and E.T. Champagne Reducing the allergenic capacity of peanut extracts and liquid peanut butter by phenolic compounds Food Chemistry 115 4 2009 1345 1349
9. S.-Y. Chung, and S. Reed Removing peanut allergens by tannic acid Food Chemistry 134 3 2012 1468 1473
10. M.N. Clifford Chlorogenic acids and other cinnamates - Nature, occurrence and dietary burden Journal of the Science of Food and Agriculture 79 3 1999 362 372 (Pubitemid 29150578)
11. M.A. Dobreva, R.A. Frazier, I. Mueller-Harvey, L.A. Clifton, A. Gea, and R.J. Green Binding of pentagalloyl glucose to two globular proteins occurs via multiple surface sites Biomacromolecules 12 3 2011 710 715
12. A. Farah, T. de Paulis, L.C. Trugo, and P.R. Martin Effect of roasting on the formation of chlorogenic acid lactones in coffee Journal of Agricultural and Food Chemistry 53 5 2005 1505 1513 (Pubitemid 40322144)
13. F. Faridbod, M.R. Ganjali, B. Larijani, S. Riahi, A.A. Saboury, and M. Hosseini Interaction study of pioglitazone with albumin by fluorescence spectroscopy and molecular docking Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 78 1 2011 96 101
14. R.A. Frazier, E.R. Deaville, R.J. Green, E. Stringano, I. Willoughby, and J. Plant Interactions of tea tannins and condensed tannins with proteins Journal of Pharmaceutical and Biomedical Analysis 51 2 2010 490 495
15. E. Gudgin, R. Lopez-Delgado, and W.R. Ware The tryptophan fluorescence lifetime puzzle. A study of decay times in aqueous solution as a function of pH and buffer composition Canadian Journal of Chemistry 59 7 1981 1037 1044
16. K. Hanhineva, R. Torronen, I. Bondia-Pons, J. Pekkinen, M. Kolehmainen, and H. Mykkanan Impact of dietary polyphenols on carbohydrate metabolism International Journal of Molecular Sciences 11 4 2010 1365 1402
17. C.D. Kanakis, I. Hasni, P. Bourassa, P.A. Tarantilis, M.G. Polissiou, and H.A. Tajmir-Riahi Milk beta-lactoglobulin complexes with tea polyphenols Food Chemistry 127 3 2011 1046 1055
18. M.K. Khan, N. Rakotomanomana, C. Dufour, and O. Dangles Binding of citrus flavanones and their glucuronides and chalcones to human serum albumin Food & Function 2 10 2011 617 626
19. J.R. Lakowicz Principles of fluorescence spectroscopy 2nd ed. 1999 Kluwer/Plenum New York
20. J.D. Lambert, and R.J. Elias The antioxidant and pro-oxidant activities of green tea polyphenols: A role in cancer prevention Archives of Biochemistry and Biophysics 501 1 2010 65 72
21. S.A. Li, K.L. Huang, M. Zhong, J. Guo, W.Z. Wang, and R.H. Zhu Comparative studies on the interaction of caffeic acid, chlorogenic acid and ferulic acid with bovine serum albumin Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 77 3 2010 680 686
22. L. Liang, and M. Subirade Study of the acid and thermal stability of β-lactoglobulin-ligand complexes using fluorescence quenching Food Chemistry 132 4 2012 2023 2029
23. L. Liang, H.A. Tajmir-Riahi, and M. Subirade Interaction of β-lactoglobulin with resveratrol and its biological implications Biomacromolecules 9 1 2007 50 56
24. J. Ma, Y.M. Yin, H.L. Liu, and M.X. Xie Interactions of flavonoids with biomacromolecules Current Organic Chemistry 15 15 2011 2627 2640
25. T.F. Martínez, and F.J. Moyano Effect of tannic acid on in vitro enzymatic hydrolysis of some protein sources Journal of the Science of Food and Agriculture 83 5 2003 456 464 (Pubitemid 36391795)
26. G.J. McDougall, N.N. Kulkarni, and D. Stewart Current developments on the inhibitory effects of berry polyphenols on digestive enzymes BioFactors 34 1 2008 73 80
27. T. Niseteo, D. Komes, A. Belščak-Cvitanović, D. Horžić, and M. Budeč Bioactive composition and antioxidant potential of different commonly consumed coffee brews affected by their preparation technique and milk addition Food Chemistry 134 4 2012 1870 1877
28. M. Obanda, P.O. Owuor, and S.J. Taylor Chemical composition of some Kenyan black teas and their probable benefits to human health Tea 17 1996 20 26
29. A. Papadopoulou, and R.A. Frazier Characterization of protein-polyphenol interactions Trends in Food Science & Technology 15 3-4 2004 186 190 (Pubitemid 38300191)
30. L.J. Porter, Z. Ma, and B.G. Chan Cacao procyanidins: Major flavonoids and identification of some minor metabolites Phytochemistry 30 1991 1657 1663
31. L. Ragona, L. Confalonieri, L. Zetta, K.G. De Kruif, S. Mammi, and E. Peggion Equilibrium unfolding CD studies of bovine β-lactoglobulin and its 14-52 fragment at acidic pH Biopolymers 49 6 1999 441 450 (Pubitemid 29157356)
32. S. Rahimi Yazdi, and M. Corredig Heating of milk alters the binding of curcumin to casein micelles. A fluorescence spectroscopy study Food Chemistry 132 3 2012 1143 1149
33. D. Renard, J. Lefebvre, M.C.A. Griffin, and W.G. Griffin Effects of pH and salt environment on the association of beta-lactoglobulin revealed by intrinsic fluorescence studies International Journal of Biological Macromolecules 22 1998 41 49 (Pubitemid 28073619)
34. L.H. Riihimaki, M.J. Vainio, J.M.S. Heikura, K.H. Valkonen, V.T. Virtanen, and P.M. Vuorela Binding of phenolic compounds and their derivatives to bovine and reindeer β-lactoglobulin Journal of Agricultural and Food Chemistry 56 17 2008 7721 7729
35. A. Shpigelman, G. Israeli, and Y.D. Livney Thermally-induced protein-polyphenol co-assemblies: Beta lactoglobulin-based nanocomplexes as protective nanovehicles for EGCG Food Hydrocolloids 24 8 2010 735 743
36. K.J. Siebert, N.V. Troukhanova, and P.Y. Lynn Nature of polyphenol-protein interactions Journal of Agricultural and Food Chemistry 44 1 1996 80 85 (Pubitemid 126458542)
37. S. Soares, N. Mateus, and V. de Freitas Interaction of different polyphenols with bovine serum albumin (BSA) and human salivary α-amylase (HSA) by fluorescence quenching Journal of Agricultural and Food Chemistry 55 16 2007 6726 6735 (Pubitemid 47280052)
38. H. Tachibana Molecular basis for cancer chemoprevention by green tea polyphenol EGCG Forum of Nutrition 61 2009 156 169
39. C. Tanford, L.G. Bunville, and Y. Nozaki The reversible transformation of b-lactoglobulin at pH 7.5 Journal of American Chemical Society 81 1959 4032 4036
40. Z. Tantoush, D. Apostolovic, B. Kravic, I. Prodic, L. Mihajlovic, and D. Stanic-Vucinic Green tea catechins of food supplements facilitate pepsin digestion of major food allergens, but hampers their digestion if oxidized by phenol oxidase Journal of Functional Foods 4 3 2012 650 660
41. N. Taulier, and T.V. Chalikian Characterization of pH-induced transitions of β-lactoglobulin: Ultrasonic, densimetric, and spectroscopic studies Journal of Molecular Biology 314 4 2001 873 889 (Pubitemid 34087854)
42. E. Ulleberg, I. Comi, H. Holm, E. Herud, M. Jacobsen, and G. Vegarud Human gastrointestinal juices intended for use in in vitro digestion models Food Digestion 2 1 2011 52 61
43. G.K. Wang, L.X. Wang, W. Tang, X.X. Hao, Y.L. Wang, and Y. Lu Binding of quercetin to lysozyme as probed by spectroscopic analysis and molecular simulation Journal of Fluorescence 21 5 2011 1879 1886
44. D. Wu, Z. Guo, Z. Ren, W. Guo, and S.N. Meydani Green tea EGCG suppresses T cell proliferation through impairment of IL-2/IL-2 receptor signaling Free Radical Biology and Medicine 47 5 2009 636 643
45. J.B. Xiao, G.Y. Kai, F. Yang, C.X. Liu, X.C. Xu, and K. Yamamoto Molecular structure-affinity relationship of natural polyphenols for bovine gamma-globulin Molecular Nutrition & Food Research 55 2011 S86 S92
46. C.S. Yang, X. Wang, G. Lu, and S.C. Picinich Cancer prevention by tea: Animal studies, molecular mechanisms and human relevance Nature Reviews Cancer 9 6 2009 429 439
47. Z. Yuksel, E. Avci, and Y.K. Erdem Characterization of binding interactions between green tea flavonoids and milk proteins Food Chemistry 121 2 2010 450 456
48. R. Zorilla, L. Liang, G. Remondetto, and M. Subirade Interaction of epigallocatechin-3-gallate with beta-lactoglobulin: Molecular characterization and biological implication Dairy Science & Technology 91 5 2011 629 644