Combined spectroscopic, molecular docking and quantum mechanics study of β-casein and p-coumaric acid interactions following thermal treatment

Food Chemistry

Volumn 252, Issue , 2018, Pages 163-170

  Kaur, Jasmeet ^a   Katopo, Lita ^a   Hung, Andrew ^a   Ashton, John ^b   Kasapis, Stefan ^a  

^a RMIT UNIVERSITY   (Australia)

^b Sanitarium Health and Wellbeing   (Australia)

Author keywords

Molecular interactions; p Coumaric acid; Thermal processing; Casein

Indexed keywords

AMINO ACIDS; FLUORESCENCE QUENCHING; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN BONDS; MECHANICS; MOLECULAR INTERACTIONS; MOLECULAR MODELING; PROTEINS; QUANTUM THEORY; SPECTROSCOPIC ANALYSIS; THERMAL PROCESSING (FOODS);

ABSORBANCE SPECTRUM; COVALENT INTERACTIONS; MOLECULAR DOCKING; OPEN STRUCTURE; P-COUMARIC ACID; PEPTIDE BACKBONES; SPECTROSCOPIC METHOD; ULTRAHIGH TEMPERATURE;

CASEIN;

BETA CASEIN; PARA COUMARIC ACID; CASEIN; LIGAND; PROPIONIC ACID DERIVATIVE; TRANS-3-(4'-HYDROXYPHENYL)-2-PROPENOIC ACID;

ARTICLE; BINDING SITE; CHROMATOPHORE; CIRCULAR DICHROISM; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; ENERGY; ENTHALPY; ENTROPY; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; HIGH TEMPERATURE; INFRARED SPECTROSCOPY; MAIZE; MOLECULAR DOCKING; PROTEIN PROTEIN INTERACTION; PROTEIN SECONDARY STRUCTURE; PROTEIN STRUCTURE; QUANTUM MECHANICS; SPECTROSCOPY; STEADY STATE; CHEMISTRY; HYDROGEN BOND; METABOLISM; PROTEIN CONFORMATION; QUANTUM THEORY; TEMPERATURE; THERMODYNAMICS;

CASEINS; HYDROGEN BONDING; LIGANDS; MOLECULAR DOCKING SIMULATION; PROPIONATES; PROTEIN CONFORMATION; QUANTUM THEORY; SPECTRUM ANALYSIS; TEMPERATURE; THERMODYNAMICS;

EID: 85041429361     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2018.01.091     Document Type: Article

References (45)

1. Arrieta-Baez, D., Dorantes-Alvares, L., Martinez-Torres, R., Zepeda-Vallejo, G., Jaramillo-Flores, M.E., Ortiz-Moreno, A., Aparicio-Ozores, G., Effect of thermal sterilization on ferulic, coumaric and cinnamic acids: Dimerization and antioxidant activity. Journal of the Science and Food Agriculture 92 (2012), 2715–2720.
2. Bader, R., Atoms in molecules. Accounts of Chemical Research 18 (1985), 9–15.
3. Barth, A., Infrared spectroscopy of proteins. BBA – Bioenergetics 1767 (2007), 1073–1101.
4. Bourassa, P., Hasni, I., Tajmir-Riahi, H.A., Folic acid complexes with human and bovine serum albumins. Food Chemistry 129 (2011), 1148–1155.
5. Bourassa, P., Bariyanga, J., Tajmir-Riahi, H.A., Binding sites of resveratrol, genistein, and curcumin with milk α- and β-caseins. The Journal of Physical Chemistry B 117 (2013), 1287–1295.
6. Chakraborty, A., Basak, S., Effect of surfactants on casein structure: A spectroscopic study. Colloids and Surfaces B: Biointerfaces 63 (2008), 83–90.
7. Fletcher, R., A new approach to variable metric algorithms. Computer Journal 13 (1970), 317–322.
8. Gani, A., Wani, S.M., Masoodi, F.A., Hameed, G., Whole-grain cereal bioactive compounds and their health benefits: a review. Journal of Food Processing Technology 3 (2012), 146–156.
9. Hanwell, D.M., Curtis, E.D., Lonie, C.D., Vandermeersch, T., Zurek, E., Hutchison, R.G., Avogadro: An advanced semantic chemical editor, visualization, and analysis platform. Journal of Cheminformatics 4 (2012), 1–17.
10. Haratifar, S., Corredig, M., Interactions between tea catechins and casein micelles and their impact on renneting functionality. Food Chemistry 143 (2014), 27–32.
11. Hasni, I., Bourassa, P., Hamdani, S., Samson, G., Carpentier, R., Tajmir-Riahi, H.A., Interaction of milk α- and β-caseins with tea polyphenols. Food Chemistry 126 (2011), 630–639.
12. He, Z., Xu, M., Zeng, M., Qin, F., Chen, J., Interactions of milk α- and β-casein with malvidin-3-O-glucoside and their effects on the stability of grape skin anthocyanin extracts. Food Chemistry 199 (2016), 314–322.
13. Humphrey, W., Dalke, A., Schulten, K., VMD – visual molecular dynamics. Journal of Molecular Graphics 14 (1996), 33–38.
14. Joye, J.I., Davidov-Pardo, G., Ludescher, D.R., McClements, J.D., Fluorescence quenching study of resveratrol binding to zein and gliadin: Towards a more rational approach to resveratrol encapsulation using water-insoluble proteins. Food Chemistry 185 (2015), 261–267.
15. Kaur, J., Katopo, L., Ashton, J., Whitson, A., Kasapis, S., Molecular interactions of milk protein with phenolic components in oat-based liquid formulations following UHT treatment and prolonged storage. Journal of the Science of Food and Agriculture, 2017 in press.
16. Kowczyk-Sadowy, M., Świsłocka, R., Lewandowska, H., Piekut, J., Lewandowski, W., Spectroscopic (FT-IR, FT-Raman, 1H-and 13C-NMR), theoretical and microbiological study of trans o-coumaric acid and alkali metal o-coumarates. Molecules 20 (2015), 3146–3169.
17. Kumosinski, T.F., Brown, E.M., Farrell, H.M., Three-dimensional molecular modeling of bovine caseins: An energy-minimized β-casein structure 1. Journal of Dairy Science 76 (1993), 931–945.
18. Lakowicz, R.J., Principles of fluorescence spectroscopy. 2006, Springer, New York.
19. Lapid, H., Agmon, N., Petersen, M.K., Voth, G.A., A bond-order analysis of the mechanism for hydrated proton mobility in liquid water. The Journal of Chemical Physics, 122, 2005, 014506.
20. Liu, F., Ma, C., Mcclements, D.J., Gao, Y., A comparative study of covalent and non-covalent interactions between zein and polyphenols in ethanol-water solution. Food Hydrocolloids 63 (2017), 625–634.
21. Lu, T., Chen, F., Multiwfn: A multifunctional wavefunction analyzer. Journal of Computational Chemistry 33 (2012), 580–592.
22. Matito, E., Poater, J., Solà, M., Duran, M., Salvador, P., Comparison of the AIM delocalization index and the Mayer and fuzzy atom bond orders. The Journal of Physical Chemistry A 109 (2005), 9904–9910.
23. Mayer, I., Bond order and valence: Relations to Mulliken's population analysis. International Journal of Quantum Chemistry 26 (1984), 151–154.
24. Mehranfar, F., Bordbar, A.K., Parastar, H., A combined spectroscopic, molecular docking and molecular dynamic simulation study on the interaction of quercetin with β-casein nanoparticles. Journal of Photochemistry & Photobiology, B: Biology 127 (2013), 100–107.
25. Micsonai, A., Wien, F., Kernya, L., Lee, Y.H., Goto, Y., Réfrégiers, M., Kardos, J., Accurate secondary structure prediction and fold recognition for circular dichroism spectroscopy. Proceedings of the National Academy of Sciences 112 (2015), E3095–E3103.
26. Mohammadi, F., Bordbar, A.K., Mohammadi, K., Divsalar, A., Saboury, A.A., Circular dichroism and fluorescence spectroscopic study on the interaction of bisdemethoxycurcumin and diacetylbisdemethoxycurcumin with human serum albumin. Canadian Journal of Chemistry 88 (2010), 155–163.
27. Mudnic, I., Modun, D., Rastija, V., Vukovic, J., Brizic, I., Katalinic, V., Boban, M., Antioxidative and vasodilatory effects of phenolic acids in wine. Food Chemistry 119 (2010), 1205–1210.
28. Pu, H., Jiang, H., Chen, R., Wang, H., Studies on the interaction between vincamine and human serum albumin: A spectroscopic approach. Luminescence 29 (2014), 471–479.
29. Prigent, S.V.E., Voragen, A.G.J., Visser, A.J.W.G., van Koningsveld, G.A., Gruppen, H., Covalent interactions between proteins and oxidation products of caffeoylquinic acid (chlorogenic acid). Journal of the Science of Food and Agriculture 87 (2007), 2502–2510.
30. Rahimi Yazdi, S., Corredig, M., Heating of milk alters the binding of curcumin to casein micelles. A fluorescence spectroscopy study. Food Chemistry 132 (2012), 1143–1149.
31. Rawel, H.M., Kroll, J., Hohl, U.C., Model studies on reactions of plant phenols with whey proteins. Food / Nahrung 45 (2001), 72–81.
32. Schmidt, M., Baldridge, K., Boatz, J., Elbert, S., Gordon, M., Jensen, J., Montgomery, J., General atomic and molecular electronic structure system. Journal of Computational Chemistry 14 (1993), 1347–1363.
33. Shahlaei, M., Madadkar-Sobhani, A., Mahnam, K., Fassihi, A., Saghaie, L., Mansourian, M., Homology modeling of human CCR5 and analysis of its binding properties through molecular docking and molecular dynamics simulation. Biochimica et Biophysica Acta (BBA)-Biomembranes 1808 (2011), 802–817.
34. Sahu, A., Kasoju, N., Bora, U., Fluorescence study of the curcumin-casein micelle complexation and its application as a drug nanocarrier to cancer cells. Biomacromolecules 9 (2008), 2905–2912.
35. Sokkar, P., Mohandass, S., Ramachandran, M., Multiple templates-based homology modeling enhances structure quality of AT1 receptor: Validation by molecular dynamics and antagonist docking. Journal of Molecular Modelling 17 (2011), 1565–1577.
36. Srinivasan, M., Singh, H., Munro, P.A., Formation and stability of sodium caseinate emulsions: influence of retorting (121°C for 15 min) before or after emulsification. Food Hydrocolloids 16 (2002), 153–160.
37. Stephens, P.J., Devlin, F.J., Chabalowski, C.F., Frisch, M.J., Ab Initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. Journal of Physical Chemistry. A 98 (1994), 11623–11627.
38. Trott, O., Olson, A.J., AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry 31 (2010), 455–461.
39. Whitmore, L., Wallace, B.A., DICHROWEB, an online server for protein secondary structure analyses from circular dichroism spectroscopic data. Nucleic Acids Research 32 (2004), W668–W673.
40. Whitmore, L., Wallace, B.A., Protein secondary structure analyses from circular dichroism spectroscopy: Methods and reference databases. Biopolymers 89 (2008), 392–400.
41. Williams, M.A., Daviter, T., Protein-ligand interactions: Methods and applications. 2013, Humana Press.
42. Wu, X., Dey, R., Wu, H., Liu, Z., He, Q., Zeng, X., Studies on the interaction of -epigallocatechin-3-gallate from green tea with bovine β-lactoglobulin by spectroscopic methods and docking. International Journal of Dairy Technology 66 (2013), 7–13.
43. Yang, J., Yan, R., Roy, A., Xu, D., Poisson, J., Zhang, Y., The I-TASSER Suite: Protein structure and function prediction. Nature Methods 12 (2015), 7–8.
44. Zelik, B., Kartal, M., Orhan, I., Cytotoxicity, antiviral and antimicrobial activities of alkaloids, flavonoids, and phenolic acids. Pharmaceutical Biology 49 (2011), 396–402.
45. Zhang, G., Ma, Y., Mechanistic and conformational studies on the interaction of food dye amaranth with human serum albumin by multispectroscopic methods. Food Chemistry 136 (2013), 442–449.