Noncovalent interactions of bovine α-lactalbumin with green tea polyphenol, epigalocatechin-3-gallate

Food Hydrocolloids

Volumn 61, Issue , 2016, Pages 241-250

  Al Hanish, Ayah ^a   Stanic Vucinic, Dragana ^a   Mihailovic, Jelena ^a   Prodic, Ivana ^a   Minic, Simeon ^a   Stojadinovic, Marija ^a   Radibratovic, Milica ^a   Milcic, Milos ^a   Cirkovic Velickovic, Tanja ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Epigallocatechin 3 gallate; Fluorescence quenching; Molecular docking; Monocyte uptake; Noncovalent interactions; Lactalbumin

Indexed keywords

EID: 84969961344     PISSN: 0268005X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodhyd.2016.05.012     Document Type: Article

References (56)

1. Almajano M.P., Delgado M.E., Gordon M.H. Changes in the antioxidant properties of protein solutions in the presence of epigallocatechin gallate. Food Chemistry 2007, 101(1):126-130.
2. Anandakrishnan R., Aguilar B., Onufriev A.V. H++3.0: automating pK prediction and the preparation of biomolecular structures for atomistic molecular modeling and simulations. Nucleic Acids Research 2012, 40(W1):W537-W541.
3. Bandyopadhyay P., Ghosh A.K., Ghosh C. Recent developments on polyphenol-protein interactions: effects on tea and coffee taste, antioxidant properties and the digestive system. Food Function 2012, 3(6):592-605.
4. Barbana C., Perez M.D., Sanchez L., Dalgalarrondo M., Chobert J.M., Haertle T. Interaction of bovine alpha-lactalbumin with fatty acids as determined by partition equilibrium and fluorescence spectroscopy. International Dairy Journal 2006, 16(1):18-25.
5. Bohin M.C., Vincken J.P., van der Hijden H.T.W.M., Gruppen H. Efficacy of food proteins as carriers for flavonoids. Journal of Agricultural and Food Chemistry 2012, 60(16):4136-4143.
6. Brooks B.R., Bruccoleri R.E., Olafson B.D., States D.J., Swaminathan S., Karplus M. CHARMM: a program for macromolecular energy, minimization, and dynamics calculations. Journal of Computational Chemistry 1983, 4(2):187-217.
7. Chakraborty S., Ittah V., Bai P., Luo L., Haas E., Peng Z.Y. Structure and dynamics of the alpha-lactalbumin molten globule: fluorescence studies using proteins containing a single tryptophan residue. Biochemistry 2001, 40(24):7228-7238.
8. Cheng H., Liu H., Bao W., Zou G. Studies on the interaction between docetaxel and human hemoglobin by spectroscopic analysis and molecular docking. Journal of Photochemistry and Photobiology B 2011, 105(2):126-132.
9. Chrysina E.D., Brew K., Acharya K.R. Crystal structures of apo- and holo-bovine alpha-lactalbumin at 2.2-A resolution reveal an effect of calcium on inter-lobe interactions. Journal of Biological Chemistry 2000, 275(47):37021-37029.
10. Delavari B., Saboury A.A., Atri M.S., Ghasemi A., Bigdeli B., Khammari A., et al. Alpha-lactalbumin: a new carrier for vitamin D-3 food enrichment. Food Hydrocolloids 2015, 45:124-131.
11. Ferruzzi M.G. The influence of beverage composition on delivery of phenolic compounds from coffee and tea. Physiology & Behavior 2010, 100(1):33-41.
12. Ferruzzi M.G., Bordenave N., Hamaker B.R. Does flavor impact function? Potential consequences of polyphenol-protein interactions in delivery and bioactivity of flavan-3-ols from foods. Physiology & Behavior 2012, 107(4):591-597.
13. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., et al. Gaussian 03, revision C.02 2004, Gaussian Inc, Wallingford CT.
14. Fu T.T., Abbott U.R., Hatzos C. Digestibility of food allergens and nonallergenic proteins in simulated gastric fluid and simulated intestinal fluid - A comparative study. Journal of Agricultural and Food Chemistry 2002, 50(24):7154-7160.
15. Fujimura Y., Tachibana H., Maeda-Yamamoto M., Miyase T., Sano M., Yamada K. Antiallergic tea catechin, (-)-epigallocatechin-3-O-(3-O-methyl)-gallate, suppresses FcepsilonRI expression in human basophilic KU812 cells. Journal of Agricultural and Food Chemistry 2002, 50(20):5729-5734.
16. Ghosh K.S., Sahoo B.K., Dasgupta S. Spectrophotometric studies on the interaction between (-)-epigallocatechin gallate and lysozyme. Chemical Physics Letters 2008, 452(1-3):193-197.
17. Hagiwara M., Matsushita K. Epigallocatechin gallate suppresses LPS endocytosis and nitric oxide production by reducing Rab5-caveolin-1 interaction. Biomedical Research 2014, 35(2):145-151.
18. Hemar Y., Gerbeaud M., Oliver C.M., Augustin M.A. Investigation into the interaction between resveratrol and whey proteins using fluorescence spectroscopy. International Journal of Food Science and Technology 2011, 46(10):2137-2144.
19. Kamau S.M., Cheison S.C., Chen W., Liu X.M., Lu R.R. Alpha-lactalbumin: its production technologies and bioactive peptides. Comprehensive Reviews in Food Science and Food Safety 2010, 9(2):197-212.
20. Kanakis C.D., Hasni I., Bourassa P., Tarantilis P.A., Polissiou M.G., Tajmir-Riahi H.A. Milk beta-lactoglobulin complexes with tea polyphenols. Food Chemistry 2011, 127(3):1046-1055.
21. Kehoe J.J., Brodkorb A. Interactions between sodium oleate and alpha-lactalbumin: the effect of temperature and concentration on complex formation. Food Hydrocolloids 2014, 34(1):217-226.
22. Keppler J., Stuhldreier M., Temps F., Schwarz K. Influence of mathematical models and correction factors on binding results of polyphenols and retinol with β-lactoglobulin measured with fluorescence quenching. Food Biophysics 2014, 1-11.
23. Kim H.S., Quon M.J., Kim J.A. New insights into the mechanisms of polyphenols beyond antioxidant properties; lessons from the green tea polyphenol, epigallocatechin 3-gallate. Redox Biology 2014, 2:187-195.
24. Laemmli U.K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970, 227(5259):680-685.
25. Lee S. Monocytes: a novel drug delivery system targeting atherosclerosis. Journal of Drug Targeting 2014, 22(2):138-145.
26. Li B., Du W.K., Jin J.C., Du Q.Z. Preservation of (-)-epigallocatechin-3-gallate antioxidant properties loaded in heat treated beta-lactoglobulin nanoparticles. Journal of Agricultural and Food Chemistry 2012, 60(13):3477-3484.
27. Livney Y.D. Milk proteins as vehicles for bioactives. Current Opinion in Colloid & Interface Science 2010, 15(1-2):73-83.
28. Maiti T.K., Ghosh K.S., Dasgupta S. Interaction of (-)-epigallocatechin-3-gallate with human serum albumin: fluorescence, fourier transform infrared, circular dichroism, and docking studies. Proteins 2006, 64(2):355-362.
29. Malinovskii V.A., Tian J., Grobler J.A., Brew K. Functional site in alpha-lactalbumin encompasses a region corresponding to a subsite in lysozyme and parts of two adjacent flexible substructures. Biochemistry 1996, 35(30):9710-9715.
30. Mohammadi F., Moeeni M. Analysis of binding interaction of genistein and kaempferol with bovine alpha-lactalbumin. Journal of Functional Foods 2015, 12:458-467.
31. Mohammadi F., Moeeni M. Study on the interactions of trans-resveratrol and curcumin with bovine alpha-lactalbumin by spectroscopic analysis and molecular docking. Materials Science and Engineering C: Materials for Biological Applications 2015, 50:358-366.
32. Mok K.H., Pettersson J., Orrenius S., Svanborg C. HAMLET, protein folding, and tumor cell death. Biochemical and Biophysical Research Communications 2007, 354(1):1-7.
33. Ognjenovic J., Stojadinovic M., Milcic M., Apostolovic D., Vesic J., Stambolic I., et al. Interactions of epigallo-catechin 3-gallate and ovalbumin, the major allergen of egg white. Food Chemistry 2014, 164:36-43.
34. Oliviero F., Sfriso P., Scanu A., Fiocco U., Spinella P., Punzi L. Epigallocatechin-3-gallate reduces inflammation induced by calcium pyrophosphate crystals in vitro. Frontiers in Pharmacology 2013, 4:1-7.
35. Ozdal T., Capanoglu E., Altay F. A review on protein-phenolic interactions and associated changes. Food Research International 2013, 51(2):954-970.
36. Pal S., Dey S.K., Saha C. Inhibition of catalase by tea catechins in free and cellular state: a biophysical approach. PLoS One 2014, 9(7).
37. Permyakov E.A., Berliner L.J. alpha-Lactalbumin: structure and function. FEBS Letters 2000, 473(3):269-274.
38. Permyakov E.A., Permyakov S.E., Deikus G.Y., Morozova-Roche L.A., Grishchenko V.M., Kalinichenko L.P., et al. Ultraviolet illumination-induced reduction of alpha-lactalbumin disulfide bridges. Proteins-Structure Function and Genetics 2003, 51(4):498-503.
39. Pike A.C.W., Brew K., Acharya K.R. Crystal structures of guinea-pig, goat and bovine alpha-lactalbumin highlight the enhanced conformational flexibility of regions that are significant for its action in lactose synthase. Structure 1996, 4(6):691-703.
40. Prigent S.V.E., Gruppen H., Visser A.J.W.G., van Koningsveld G.A., de Jong G.A.H., Voragen A.G.J. 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 2003, 51(17):5088-5095.
41. Prigent S.V.E., Voragen A.G.J., van Koningsveld G.A., Baron A., Renard C.M.G.C., Gruppen H. Interactions between globular proteins and procyanidins of different degrees of polymerization. Journal of Dairy Science 2009, 92(12):5843-5853.
42. Shpigelman A., Cohen Y., Livney Y.D. Thermally-induced beta-lactoglobulin-EGCG nanovehicles: loading, stability, sensory and digestive-release study. Food Hydrocolloids 2012, 29(1):57-67.
43. Stanic-Vucinic D., Stojadinovic M., Atanaskovic-Markovic M., Ognjenovic J., Gronlund H., van Hage M., et al. Structural changes and allergenic properties of beta-lactoglobulin upon exposure to high-intensity ultrasound. Molecular Nutrition & Food Research 2012, 56(12):1894-1905.
44. Stanic D., Radosavljevic J., Polovic N., Jadranin M., Popovic M., Vuckovic O., et al. Removal of N-terminal peptides from beta-lactoglobulin by proteolytic contaminants in a commercial phenol oxidase preparation. International Dairy Journal 2009, 19(12):746-752.
45. Takase K., Niki R., Arima S. Environment of tryptophan residues in alpha-lactalbumin. Journal of Biochemistry 1978, 83(2):371-378.
46. Trott O., Olson A.J. Software news and update autodock vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry 2010, 31(2):455-461.
47. Vesic J., Stambolic I., Apostolovic D., Milcic M., Stanic-Vucinic D., Velickovic T.C. Complexes of green tea polyphenol, epigalocatechin-3-gallate, and 2S albumins of peanut. Food Chemistry 2015, 185:309-317.
48. Wang S.H., Liu F.F., Dong X.Y., Sun Y. Calorimetric and spectroscopic studies of the interactions between insulin and (-)-epigallocatechin-3-gallate. Biochemical Engineering Journal 2012, 62:70-78.
49. Wang S.H., Sun Z.Y., Dong S.Z., Liu Y., Liu Y. Molecular interactions between (-)-epigallocatechin gallate analogs and pancreatic lipase. PLoS One 2014, 9(11).
50. Wang X.Y., Zhang J., Lei F., Liang C.X., Yuan F., Gao Y.X. Covalent complexation and functional evaluation of (-)-epigallocatechin gallate and alpha-lactalbumin. Food Chemistry 2014, 150:341-347.
51. Wu X.L., He W.Y., Wang W.P., Luo X.P., Cao H.Y., Lin L.X., et al. Investigation of the interaction between (-)-epigallocatechin-3-gallate with trypsin and alpha-chymotrypsin. International Journal of Food Science and Technology 2013, 48(11):2340-2347.
52. Wu X., He W., Yao L., Zhang H., Liu Z., Wang W., et al. Characterization of binding interactions of (-)-epigallocatechin-3-gallate from green tea and lipase. Journal of Agricultural and Food Chemistry 2013, 61(37):8829-8835.
53. 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. Molecular Nutrition & Food Research 2011, 55(11):1637-1645.
54. Yoneyama S., Kawai K., Tsuno N.H., Okaji Y., Asakage M., Tsuchiya T., et al. Epigallocatechin gallate affects human dendritic cell differentiation and maturation. Journal of Allergy and Clinical Immunology 2008, 121(1):209-214.
55. Zhang H., Yu D.D., Sun J., Guo H.Y., Ding Q.B., Liu R.H., et al. Interaction of milk whey protein with common phenolic acids. Journal of Molecular Structure 2014, 1058:228-233.
56. Zhao Y.Y., Chen L.J., Han L.J., Marzinek J.K., Mantalaris A., Pistikopoulos E.N., et al. Molecular and thermodynamic basis for EGCG-keratin interaction-part II: experimental investigation. AICHE Journal 2013, 59(12):4824-4827.