Free radical scavenging potency of quercetin catecholic colonic metabolites: Thermodynamics of 2H+/2e− processes

Food Chemistry

Volumn 218, Issue , 2017, Pages 144-151

  Amić, Ana ^a   Lučić, Bono ^b   Stepanić, Višnja ^b   Marković, Zoran ^c   Marković, Svetlana ^d   Dimitrić Marković, Jasmina M ^e   Amić, Dragan ^a  

^a JOSIP JURAJ STROSSMAYER UNIVERSITY OF OSIJEK   (Croatia)

^b RUDER BO KOVI INSTITUTE   (Croatia)

^c State University of Novi Pazar   (Serbia)

^d UNIVERSITY OF KRAGUJEVAC   (Serbia)

^e UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Catecholic compounds; Colonic metabolites; Double HAT; Double SPLET; Quercetin; Radical scavenging

Indexed keywords

ATOMS; BIOMOLECULES; DENSITY FUNCTIONAL THEORY; FLAVONOIDS; FREE ENERGY; FREE RADICAL REACTIONS; GIBBS FREE ENERGY; METABOLITES; PHENOLS; THERMODYNAMICS;

CATECHOLIC COMPOUNDS; DOUBLE HAT; DOUBLE SPLET; QUERCETIN; RADICAL SCAVENGING;

FREE RADICALS;

3,4 DIHYDROXYPHENYLACETIC ACID; 4 METHYLCATECHOL; ANTIOXIDANT; CAFFEIC ACID; CATECHOL; DIHYDROCAFFEIC ACID; DRUG METABOLITE; FREE RADICAL; HYDROGEN; PROTOCATECHUIC ACID; QUERCETIN DERIVATIVE; DEUTERIUM; PROTON; QUERCETIN; SCAVENGER;

ANTIOXIDANT ACTIVITY; ARTICLE; DENSITY FUNCTIONAL THEORY; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENCY; ELECTRON TRANSPORT; THERMODYNAMICS; CHEMISTRY; METABOLISM; OXIDATION REDUCTION REACTION; PHYSIOLOGY;

DEUTERIUM; ELECTRON TRANSPORT; FREE RADICAL SCAVENGERS; FREE RADICALS; HYDROGEN; OXIDATION-REDUCTION; PROTONS; QUERCETIN; THERMODYNAMICS;

EID: 84988025491     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2016.09.018     Document Type: Article

References (40)

1. Alvarez-Diduk, R., Ramirez-Silva, M.T., Galano, A., Merkoci, A., Deprotonation mechanism and acidity constants in aqueous solution of flavonols: A combined experimental and theoretical study. Journal of Physical Chemistry B 117:41 (2013), 12347–12359.
2. Amić, A., Marković, Z., Dimitrić Marković, J.M., Stepanić, V., Lučić, B., Amić, D., Towards an improved prediction of the free radical scavenging potency of flavonoids: The significance of double PCET mechanisms. Food Chemistry 152 (2014), 578–585.
3. Aura, A.-M., Microbial metabolism of dietary phenolic compounds in the colon. Phytochemistry Reviews 7:3 (2008), 407–429.
4. Bors, W., Heller, W., Michel, C., Saran, M., Flavonoids as antioxidants: Determination of radical-scavenging efficiencies. Packer, L., Glazer, A.N., (eds.) Methods in enzymology, 1990, Academic Press, San Diego, 343–355.
5. Clifford, M.N., Diet-derived phenols in plasma and tissues and their implications for health. Planta Medica 70:12 (2004), 1103–1114.
6. Dangles, O., Antioxidant activity of plant phenols: Chemical mechanisms and biological significance. Current Organic Chemistry 16:6 (2012), 692–714.
7. Del Rio, D., Rodriguez-Mateos, A., Spencer, J.P.E., Tognolini, M., Borges, G., Crozier, A., Dietary (poly)phenolics in human health: Structures, bioavailability, and evidence of protective effects against chronic diseases. Antioxidants & Redox Signaling 18:4 (2013), 1818–1892.
8. Duenas, M., Surco-Laos, F., Gonzalez-Manzano, S., Gonzalez-Paramas, A.M., Santos-Buelga, C., Antioxidant properties of major metabolites of quercetin. European Food and Research Technology 232:1 (2011), 103–111.
9. Fiourucci, S., Golebiowski, J., Cabrol-Bass, D., Antonczak, S., DFT study of quercetin activated forms involved in antiradical, antioxidant, and prooxidant biological processes. Journal of Agricultural and Food Chemistry 55:3 (2007), 903–911.
10. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., et al. Gaussian 09, revision D.01, 2013, Gaussian Inc, Wallingford, CT.
11. Galano, A., Mazzone, G., Alvarez-Diduk, R., Marino, T., Alvarez-Idaboy, J.R., Russo, N., Food antioxidants: Chemical insights at the molecular level. Annual Review of Food Science and Technology 7 (2016), 335–352.
12. Galano, A., Perez-Gonzalez, A., On the free radical scavenging mechanism of protocatechuic acid, regeneration of the catechol group in aqueous solution. Theoretical Chemistry Accounts, 131(9), 2012, 1265.
13. Galleano, M., Verstraeten, S.V., Oteiza, P.I., Fraga, C.G., Antioxidant actions of flavonoids: Thermodynamic and kinetic analysis. Archives of Biochemistry and Biophysics 501:1 (2010), 23–30.
14. Grimme, S., Antony, J., Ehrlich, S., Krieg, H., A consistent and accurate ab initio parametrization of density functional dispersion correlation (DFT-D) for the 94 elements H-Pu. Journal of Chemical Physics, 132(15), 2010, 154104.
15. Halliwell, B., Rafter, J., Jenner, A., Health promotion by flavonoids, tocopherols, tocotrienols, and other phenols: Direct or indirect effects? Antioxidant or not?. American Journal of Clinical Nutrition 81:1 (2005), 268S–276S.
16. Hollman, P.C.H., Unravelling of the health effects of polyphenols is a complex puzzle complicated by metabolism. Archives of Biochemistry and Biophysics 559 (2014), 100–105.
17. Huang, J., de Paulis, T., May, J.M., Antioxidant effects of dihydrocaffeic acid in human EA.hy926 endothelial cells. Journal of Nutritional Biochemistry 15:12 (2004), 722–729.
18. Iuga, C., Alvarez-Idaboy, J.R., Vivier-Bunge, A., ROS initiated oxidation of dopamine under oxidative stress conditions in aqueous and lipidic environments. Journal of Physical Chemistry B 115:42 (2011), 12234–12246.
19. Jovanovic, S.V., Simic, M.G., Antioxidants in nutrition. Annals of the New York Academy of Sciences 899 (2000), 326–334.
20. Kim, D.-O., Lee, C.Y., Comprehensive study on vitamin C equivalent antioxidant capacity (VCEAC) of various polyphenolics in scavenging a free radical and its structural relationship. Critical Reviews in Food Science and Nutrition 44:4 (2004), 253–273.
21. Leon-Carmona, J.R., Alvarez-Idaboy, J.R., Galano, A., On the peroxyl scavenging activity of hydroxycinnamic acid derivatives: Mechanisms, kinetics, and importance of the acid-base equilibrium. Physical Chemistry Chemical Physics 14:36 (2012), 12534–12543.
22. Leopoldini, M., Russo, N., Toscano, M., The molecular basis of working mechanisms of natural polyphenolic antioxidants. Food Chemistry 125:2 (2011), 288–306.
23. Lespade, L., Bercion, S., Theoretical investigation of the effect of sugar substitution on the antioxidant properties of flavonoids. Free Radical Research 46:3 (2012), 346–358.
24. Lucarini, M., Pedrielli, P., Pedulli, G.F., Cabiddu, S., Fattuoni, C., Bond dissociation energies of O−H bonds in substituted phenols from equilibration studies. Journal of Organic Chemistry 61:26 (1996), 9259–9263.
25. Manach, C., Scalbert, A., Morand, C., Remesy, C., Jimenez, L., Polyphenols: Food sources and bioavailability. American Journal of Clinical Nutrition 79:5 (2004), 727–747.
26. Marenich, A.V., Cramer, C.J., Truhlar, D.G., Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. Journal of Physical Chemistry B 113:18 (2009), 6378–6396.
27. Masella, R., Santangelo, C., D'Archivio, M., Li Volti, G., Giovannini, C., Galvano, F., Protocatechuic acid and human disease prevention: Biological activities and molecular mechanisms. Current Medicinal Chemistry 19:18 (2012), 2901–2917.
28. Merfort, I., Heilmann, J., Weiss, M., Pietta, P., Gardana, C., Radical scavenger activity of three flavonoid metabolites studied by inhibition of chemiluminescence in human PMNs. Planta Medica 62:4 (1996), 289–292.
29. Musialik, M., Kuzmicz, R., Pawlowski, T.S., Litwinienko, G., Acidity of hydroxyl groups: An overlooked influence on antiradical properties of flavonoids. Journal of Organic Chemistry 74:7 (2009), 2699–2709.
30. Payton, F., Bose, R., Alworth, W.L., Kumar, A.P., Ghosh, R., 4-Methylcatechol-induced oxidative stress induces intrinsic apoptotic pathway in metastatic melanoma cells. Biochemical Pharmacology 81:10 (2011), 1211–1218.
31. Perez-Gonzalez, A., Alvarez-Idaboy, J.R., Galano, A., Free-radical scavenging by tryptophan and its metabolites through electron transfer based processes. Journal of Molecular Modeling, 21(8), 2015, 213.
32. Rechner, A.R., Smith, M.A., Kuhnle, G., Gibson, G.R., Debnam, E.S., Srai, S.K.S., et al. Colonic metabolism of dietary polyphenols: Influence of structure on microbial fermentation products. Free Radical Biology & Medicine 36:2 (2004), 212–225.
33. Rimarčik, J., Lukeš, V., Klein, E., Ilčin, M., Study of the solvent effect on the enthalpies of homolytic and heterolytic N–H bond cleavage in p-phenylenediamine and tetracyano-p-phenylenediamine. Journal of Molecular Structure (Theochem) 952:1–3 (2010), 25–30.
34. Schweigert, N., Zehnder, A.J.B., Eggen, R.I.L., Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals. Environmental Microbiology 3:2 (2001), 81–91.
35. Selma, M.V., Espin, J.C., Tomas-Barberan, F.A., Interaction between phenolics and gut microbiota: Role in human health. Journal of Agricultural and Food Chemistry 57:15 (2009), 6485–6501.
36. Taubert, D., Breitenbach, T., Lazar, A., Censarek, P., Harlfinger, S., Berkels, R., et al. Reaction rate constants of superoxide scavenging by plant antioxidants. Free Radical Biology & Medicine 35:12 (2003), 1599–1607.
37. Tu, T., Giblin, D., Gross, M.L., Structural determinant of chemical reactivity and potential health effects of quinones from natural products. Chemical Research in Toxicology 24:9 (2011), 1527–1539.
38. Vaganek, A., Rimarčik, J., Dropkova, K., Lengyel, J., Klein, E., Reaction enthalpies of O−H bonds splitting-off in flavonoids: The role of non-polar and polar solvent. Computational and Theoretical Chemistry 1050 (2014), 31–38.
39. Williamson, G., Clifford, M.N., Colonic metabolites of berry polyphenols: The missing link to biological activity?. British Journal of Nutrition 104:S3 (2010), S48–S66.
40. Zhao, Y., Schultz, N.E., Truhlar, D.G., Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. Journal of Chemical Theory and Computation 2:2 (2006), 364–382.