Characterization of resveratrol-milk protein interaction

Journal of Food Engineering

Volumn 167, Issue , 2015, Pages 217-225

  Ghorbani Gorji, Elham ^a   Rocchi, Elisa ^b   Schleining, Gerhard ^a   Bender Bojalil, Denisse ^c   Furtmüller, Paul G ^a   Piazza, Laura ^b   Iturri, Jagoba J ^a   Toca Herrera, José L ^a  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^b UNIVERSITY OF MILAN   (Italy)

^c UNIVERSIDAD DE LAS AMÉRICAS PUEBLA   (Mexico)

Author keywords

Bovine serum albumin; Circular dichroism; Fluorescence; Resveratrol; Transmission electron microscopy; casein; lactoglobulin

Indexed keywords

BINDING SITES; BODY FLUIDS; CASEIN; DICHROISM; ELECTRON MICROSCOPY; FLUORESCENCE; MAMMALS; POLYPHENOLIC COMPOUNDS; RESVERATROL; SURFACE PLASMON RESONANCE; TRANSMISSION ELECTRON MICROSCOPY;

ANTI-OXIDANT ACTIVITIES; BETA-LACTOGLOBULIN; BOVINE SERUM ALBUMINS; CONFORMATIONAL CHANGE; INTRINSIC FLUORESCENCE; LACTOGLOBULIN; SECONDARY STRUCTURE OF PROTEINS; STEADY STATE FLUORESCENCES;

PROTEINS;

EID: 84942295388     PISSN: 02608774     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfoodeng.2015.05.032     Document Type: Article

References (90)

1. C. Allen, D. Maysinger, and A. Eisenberg Nano-engineering block copolymer aggregates for drug delivery Colloids Surf., B 16 1-4 1999 3 27
2. J. Baur, K. Pearson, N. Price, and H. Jamieson Resveratrol improves health and survival of mice on a high-calorie diet Nature 444 7117 2006 337 342
3. J. Baur, and D. Sinclair Therapeutic potential of resveratrol: the in vivo evidence Nat. Rev. Drug Discovery 5 6 2006 493 506
4. N. Baxter, T. Lilley, E. Haslam, and M. Williamson Multiple interactions between polyphenols and a salivary proline-rich protein repeat result in complexation and precipitation Biochemistry 36 18 1997 5566 5577
5. A. Bertelli, L. Giovannini, and R. Stradi Kinetics of trans-and cis-resveratrol (3, 4', 5-trihydroxystilbene) after red wine oral administration in rats Int. J. Clin. Pharmacol. Res. 16 5-6 1996 77 81
6. P. Bourassa, and C. Kanakis Resveratrol, genistein, and curcumin bind bovine serum albumin J. Phys. Chem. B 114 9 2010 3348 3354
7. D. Boxer, H. Zhang, and D. Gourley Sensing of remote oxyanion binding at the DNA binding domain of the molybdate-dependent transcriptional regulator ModE. Org. Biomol. Chem. 2 19 2004 2829 2837
8. P. Busti, C.A. Gatti, and N.J. Delorenzi Some aspects of β-lactoglobulin studied by fluorescence quenching Int. J. Biol. Macromol. 23 1998 143 148
9. D.C. Carter, and J.X. Ho Advances in Protein Chemistry: Lipoproteins, Apolipoproteins, and Lipases 1994 Academic Press San Diego
10. A. Chakraborty, and S. Basak PH-induced structural transitions of caseins J. Photochem. Photobiol. B, Biol. 87 3 2007 191 199
11. Y. Cho, C. Batt, and L. Sawyer Probing the retinol-binding site of bovine beta-lactoglobulin J. Biol. Chem. 269 15 1994 11102 11107
12. M. Collini, L. D'Alfonso, and G. Baldini New insight on β-lactoglobulin binding sites by 1-anilinonaphthalene-8-sulfonate fluorescence decay Protein Sci. 9 10 2000 1968 1974
13. S. Das, H. Lin, P. Ho, and K. Ng The impact of aqueous solubility and dose on the pharmacokinetic profiles of resveratrol Pharm Res. 25 11 2008 2593 2600
14. S. Dauphas, N. Mouhousriou, B. Metro, A. Mackie, P. Wilde, M. Anton, and A. Riaublanc The supramolecular organisation of β-casein: effect on interfacial properties Food Hydrocolloids 19 3 2005 387 393
15. F. Diarrassouba, L. Liang, G. Remondetto, and M. Subirade Nanocomplex formation between riboflavin and β-lactoglobulin: spectroscopic investigation and biological characterization Food Res. Int. 52 2 2013 557 567
16. E. Dickinson An Introduction to Food Colloids 1992 Oxford University Press Oxford
17. E. Dickinson, and G. Stainsby Colloids in Food 1982 Applied Science Publishers London
18. Y. Ding, Y. Shu, L. Ge, and R. Guo The effect of sodium dodecyl sulfate on the conformation of bovine serum albumin Colloids Surf. A 298 3 2007 163 169
19. E. Dufour, C. Genot, and T. Haertlé β-Lactoglobulin binding properties during its folding changes studied by fluorescence spectroscopy BBA-Protein Struct. Mol. Enzymol. 1205 1 1994 3254 3263
20. A. Elzoghby, W. Samy, and N. Elgindy Albumin-based nanoparticles as potential controlled release drug delivery systems J. Controlled Release 157 2 2012 168 182
21. M. Esmaili, M. Ghaffari, Z. Moosavi-Movahedi, M.S. Atri, A. Sharifizadeh, M. Farhadi, and A.A. Moosavi-Movahedi Beta casein-micelle as a nano vehicle for solubility enhancement of curcumin; food industry application LWT-Food Sci. Technol. 40 10 2011 2166 2172
22. R. Fang, R. Hao, X. Wu, and Q. Li Bovine serum albumin nanoparticle promotes the stability of quercetin in simulated intestinal fluid J. Agric. Food Chem. 59 11 2011 6292 6298
23. Z. Fang, and B. Bhandari Encapsulation of polyphenols - a review Trends Food Sci. Technol. 10 21 2010 510 523
24. H.M.F. Farrell Jr., E.D. Wickham, J.J. Unruh, P.X. Qi, and P.D. Hoagland Secondary structural studies of bovine caseins: temperature dependence of β-casein structure as analyzed by circular dichroism and FTIR spectroscopy and correlation with micellization Food Hydrocolloids 15 4 2001 341 354
25. B. Fauconneau, P. Waffo-Teguo, and F. Huguet Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests Life Sci. 61 21 1997 2103 2110
26. S.A. Forrest, R.Y. Yada, and D. Rousseau Interactions of vitamin D3 with bovine β-lactoglobulin A and β-casein J. Agric. Food Chem. 53 20 2005 8003 8009
27. E. Frankel, J. German, J. Kinsella, E. Parks, and J. Kanner Inhibition of oxidation of human low-density lipoprotein by phenolic substances in red wine The Lancet 341 8843 1993 454 457
28. T. Gauthier, and E. Shane Fluorescence quenching method for determining equilibrium constants for polycyclic aromatic hydrocarbons binding to dissolved humic materials Environ. Sci. Technol. 20 11 1986 1162 1166
29. P.S. Given Encapsulation of flavors in emulsions for beverages Curr. Opin. Colloid Interface Sci. 14 1 2009 43 47
30. D. Graham, and M. Phillips Proteins at liquid interfaces: I. kinetics of adsorption and surface denaturation J. Colloid Interface Sci. 70 3 1979 403 414
31. D. Graham, and M. Phillips Proteins at liquid interfaces: II. adsorption isotherms J. Colloid Interface Sci. 70 3 1979 415 426
32. D. Graham, and M. Phillips Proteins at liquid interfaces: III. molecular structures of adsorbed films J. Colloid Interface Sci. 70 3 1979 403 414
33. M. Grinstaff, and K. Suslick Air-filled proteinaceous microbubbles: synthesis of an echo-contrast agent PNAS 88 17 1991 7708 7710
34. Y. Han, D. Shchukin, J. Yang, and C. Simon Biocompatible protein nanocontainers for controlled drugs release ACS Nano 4 5 2010 2838 2844
35. J.P. Hindmarsh, K.G. Hollingsworth, D.I. Wilson, and M.L. Johns An NMR study of the freezing of emulsion-containing drops J. Colloid Interface Sci. 1 275 2004 165 171
36. Y. Hu, Y. Liu, X. Shen, X. Fang, and S. Qu Studies on the interaction between 1-hexylcarbamoyl-5-fluorouracil and bovine serum albumin J. Mol. Struct. 738 1 2005 143 147
37. B. Jachimska, M. Wasilewska, and Z. Adamczyk Characterization of globular protein solutions by dynamic light scattering, electrophoretic mobility, and viscosity measurements Langmuir 12 2008 6866 6872
38. M. Jang, L. Cai, G. Udeani, and K. Slowing Cancer chemopreventive activity of resveratrol, a natural product derived from grapes Science 25 2-3 1997 65 77
39. X.Y. Jiang, W.X. Li, and H. Cao Study of the interaction between trans-resveratrol and BSA by the multi-spectroscopic method J. Solution Chem. 37 11 2008 1609 1623
40. S.N. Jimenez-Garcia, R.G. Guevara-Gonzalez, R. Miranda-Lopez, A.A. Feregrino-Perez, I. Torres-Pacheco, and M.A. Vazquez-Cruz Functional properties and quality characteristics of bioactive compounds in berries: biochemistry, biotechnology, and genomics Food Res. Int. 1 54 2012 1195 1207
41. B. Kainz, K. Steiner, M. Möller, D. Pum, C. Schäffer, U.B. Sleytr, and J.L. Toca-Herrera Steady-state fluorescence, fluorescence lifetime, and 2D self-assembly properties of engineered fluorescent S-layer fusion proteins of Geobacillus stearothermophilus Biomacromolecules 11 1 2009 207 214
42. S.M. Kelly, T.J. Jess, and N.C. Price How to study proteins by circular dichroism Biochim. Biophys. Acta 1751 2 2005 119 139
43. B. Klajnert, and M. Bryszewska Fluorescence studies on PAMAM dendrimers interactions with bovine serum albumin Bioelectrochemistry 55 1-2 2002 33 35
44. S. Ko, and S. Gunasekaran Preparation of sub-100-nm β-lactoglobulin (BLG) nanoparticles J. Microencapsulation 23 8 2006 887 898
45. G. Kontopidis, C. Holt, and L. Sawyer Invited review: β-lactoglobulin: binding properties, structure, and function J. Dairy Sci. 87 4 2004 785 796
46. J. Kühn, and X. Zhu Binding of 2-nonanone and milk proteins in aqueous model systems J. Agric. Food Chem. 55 9 2007 3599 3604
47. J. Lakowicz, and B. Masters Principles of fluorescence spectroscopy J. Biomed. Opt. 13 2 2008 9901
48. T. Lefèvre, and M. Subirade Formation of intermolecular β-sheet structures: a phenomenon relevant to protein film structure at oil-water interfaces of emulsions J. Colloid Interface Sci. 263 1 2003 59 67
49. S. Lehrer Solute perturbation of protein fluorescence. The quenching of tryptophyl fluorescence of model compounds and of lysozyme by iodide ion Biochemistry 10 17 1971 3254 3263
50. L. Liang, and M. Subirade β-Lactoglobulin/folic acid complexes: formation, characterization, and biological implication J. Phys. Chem. B 114 19 2010 6707 6712
51. L. Liang, H. Tajmir-Riahi, and M. Subirade Interaction of β-lactoglobulin with resveratrol and its biological implications Biomacromolecules 1 9 2007 50 56
52. L. Lin Characterizations of Oil-in-water (O/W) Emulsions Containing Different Types of Milk Fats Prepared Using Rhamnolipids as Emulsifiers 2009 Massey University Auckland, New Zealand
53. X. Liu, L. Shang, X. Jiang, S. Dong, and E. Wang Conformational changes of β-lactoglobulin induced by anionic phospholipid Biophys. Chem. 121 3 2006 218 223
54. Y.D. Livney Milk proteins as vehicles for bioactives Curr. Opin. Colloid Interface Sci. 1 15 2010 73 83
55. Malvern. 2015. A basic guide to particle characterization. Inform white paper < http://golik.co.il/Data/ABasicGuidtoParticleCharacterization%282%29-1962085150.pdf > (Latest access: 15.03.15).
56. Malvern. 2015. Zeta potential an introduction in 30 minutes. Zeta sizer nano series technical note, vol. 2, pp. 1-6 < http://www3.nd.edu/~rroeder/ame60647/slides/zeta.pdf > (Latest access: 15.03.15).
57. A. Matalanis, O.G. Jones, and D.J. McClements Structured biopolymer-based delivery systems for encapsulation, protection, and release of lipophilic compounds Food Hydrocolloids 8 25 2011 1865 1880
58. T. McHugh, and J. Krochta Milk-protein-based edible films and coatings Food Technol. 48 1 1994 97 103
59. D.J. McMahon, and R.J. Brown Composition, structure, and integrity of casein micelles: a review J. Dairy Sci. 3 67 1984 499 512
60. F. Mohammadi, A.-K. Bordbar, A. Divsalar, K. Mohammadi, and A.A. Saboury Analysis of binding interaction of curcumin and diacetylcurcumin with human and bovine serum albumin using fluorescence and circular dichroism spectroscopy Protein J. 28 3-4 2009 189 196
61. A. Munin, and F. Edwards-Lévy Encapsulation of natural polyphenolic compounds; a review Pharmaceutics 4 3 2011 793 829
62. C. N′Soukpoé-Kossi, C. St-Louis, M. Beauregard, M. Subirade, R. Carpentier, S. Hotchandani, and H.A. Tajmir-Riahi Resveratrol binding to human serum albumin J. Biomol. Struct. Dyn. 24 3 2006 277 283
63. C. Pace-Asciak, S. Hahn, and E. Diamandis The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against Clin. Chim. Acta 235 2 1995 207 219
64. G. Palazolo, F. RodrI, B. Farruggia, and G. Pico Heat treatment of β-lactoglobulin: structural changes studied by partitioning and fluorescence J. Agric. Food Chem. 48 9 2000 3817 3822
65. M. Papiz, L. Sawyer, and E. Eliopoulos The structure of β-lactoglobulin and its similarity to plasma retinol-binding protein Nature 324 6095 1986 383 385
66. E. Pinho, M. Grootveld, G. Soares, and M. Henriques Cyclodextrins as encapsulation agents for plant bioactive compounds Carbohydr. Polym. 101 2013 121 135
67. H.M. Rawel, S.K. Frey, K. Meidtner, J. Kroll, and F.J. Schweigert Determining the binding affinities of phenolic compounds to proteins by quenching of the intrinsic tryptophan fluorescence Mol. Nutr. Food Res. 50 8 2006 705 713
68. H. Rollema, and P. Fox Casein Association and Micelle Formation. Advanced Dairy Chemistry, Volume 1: Proteins 1992 Elsevier Science Publisher Essex
69. P.S. Roy, A. Samanta, M. Mukherjee, B. Roy, and A. Mukherjee Designing novel pH-induced Chitosan-Gum Odina complex coacervates for colon targeting Ind. Eng. Chem. Res. 52 45 2013 15728 15745
70. S.M.T. Shaikh, J. Seetharamappa, P.B. Kandagal, D.H. Manjunatha, and S. Ashoka Spectroscopic investigations on the mechanism of interaction of bioactive dye with bovine serum albumin Dyes Pigm. 74 3 2007 665 671
71. H. Singh, and A. Ye Interactions and functionality of milk proteins in food emulsions A. Thompson, M. Boland, H. Singh, Milk Proteins: From Expression to Food 2009 Elsevier, Academic Press Amsterdam
72. U. Stervbo, O. Vang, and C. Bonnesen A review of the content of the putative chemopreventive phytoalexin resveratrol in red wine Food Chem. 101 2 2007 449 457
73. C. Sun, J. Yang, X. Wu, X. Huang, F. Wang, and S. Liu Unfolding and refolding of bovine serum albumin induced by cetylpyridinium bromide Biophys. J. 88 5 2005 3518 3524
74. K. Suslick, and M. Grinstaff Protein microencapsulation of nonaqueous liquids J. Am. Chem. Soc. 112 21 1990 7807 7809
75. C.-H. Tang, and L. Shen Role of conformational flexibility in the emulsifying properties of bovine serum albumin J. Agric. Food Chem. 12 61 2013 3097 3110
76. Z. Teng, Y. Li, Y. Luo, B. Zhang, and Q. Wang Cationic β-lactoglobulin nanoparticles as a bioavailability enhancer: protein characterization and particle formation Biomacromolecules 14 8 2013 2848 2856
77. K. Teskac, and J. Kristl The evidence for solid lipid nanoparticles mediated cell uptake of resveratrol Int. J. Pharm. 1 390 2010 61 69
78. H. Visser Protein Interactions 1992 VCH New York
79. B. Wallace, and R. Janes Circular dichroism and synchrotron radiation circular dichroism spectroscopy: tools for drug discovery Biochem. Soc. Trans. 31 3 2003 631 633
80. Q. Wang, J.C. Allen, and H.E. Swaisgood Binding of vitamin D and cholesterol to β-lactoglobulin J. Dairy Sci. 80 6 1997 1054 1059
81. T. Wang, B. Xiang, Y. Wang, C. Chen, Y. Dong, H. Fang, and M. Wang Spectroscopic investigation on the binding of bioactive pyridazinone derivative to human serum albumin and molecular modeling Colloids Surf. B 65 1 2008 113 119
82. Y.-Q. Wang, H.-M. Zhang, G.-C. Zhang, W.-H. Tao, and S.-H. Tang Binding of brucine to human serum albumin J. Mol. Struct. 830 1-3 2007 40 45
83. W.W. Wilson, P. Fang, and G.D. McGinnis Disassociation of polyphenolics studied by dynamic light scattering and size exclusion chromatography J. Appl. Polym. Sci. 24 10 1979 2195 2198
84. M. Yagi, K. Sakurai, C. Kalidas, C. Batt, and Y. Goto Reversible unfolding of bovine β-lactoglobulin mutants without a free thiol group J. Biol. Chem. 278 47 2003 47009 47015
85. A. Ye, and H. Singh Formation of multilayers at the interface of oil-in-water emulsion via interactions between lactoferrin and β-lactoglobulin Food Biophys. 2 4 2007 125 132
86. B. Yedomon, H. Fessi, and C. Charcosset Preparation of bovine serum albumin (BSA) nanoparticles by desolvation using a membrane contactor: a new tool for large scale production Eur. J. Pharm. Biopharm. 85 2013 398 405
87. K. Yoshiyuki, O. Hiromichi, and A. Shigeru Effects of stilbenes on arachidonate metabolism in leukocytes BBA-Lipid Lipid Met. 834 2 1985 275 278
88. Q. Yue, T. Shen, C. Wang, C. Gao, and J. Liu Study on the interaction of bovine serum albumin with ceftriaxone and the inhibition effect of zinc (II) Int. J. Spectrosc. 2012 2012 1 9
89. W. Zhang, and Q. Zhong Microemulsions as nanoreactors to produce whey protein nanoparticles with enhanced heat stability by thermal pretreatment Food Chem. 119 4 2010 1318 1325
90. P. Zimet, Y.D.Y. Livney, E. Dickinson, and T. Nicolai β-lactoglobulin and its nanocomplexes with pectin as vehicles for ω-3 polyunsaturated fatty acids Food Hydrocolloids 23 4 2009 1120 1126