Towards an improved prediction of the free radical scavenging potency of flavonoids: The significance of double PCET mechanisms

Food Chemistry

Volumn 152, Issue , 2014, Pages 578-585

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

^a JOSIP JURAJ STROSSMAYER UNIVERSITY OF OSIJEK   (Croatia)

^b STATE UNIVERSITY OF NOVI PAZAR   (Serbia)

^c UNIVERSITY OF BELGRADE   (Serbia)

^d RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

BDE; Double PCET; ETE; Flavonoid; QSAR; Radical scavenging

Indexed keywords

ATOMS; CHEMICAL BONDS; ELECTRON TRANSITIONS; FREE RADICAL REACTIONS; PROTONS;

BDE; DOUBLE PCET; ETE; FLAVONOID; QSAR; RADICAL SCAVENGING;

FLAVONOIDS;

CATECHOL; FLAVONE DERIVATIVE; HYDROGEN; HYDROQUINONE; MORIN; NARINGENIN; PHENOL; QUERCETIN; RESORCINOL;

ANALYTIC METHOD; ANTIOXIDANT ACTIVITY; ARTICLE; CELL DEATH; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ELECTRON TRANSPORT; ELECTROPHILICITY; ENTHALPY; IONIZATION; ISOMERIZATION; PROTON COUPLED ELECTRON TRANSFER; PROTON TRANSPORT; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STOICHIOMETRY;

BDE; DOUBLE PCET; ETE; FLAVONOID; QSAR; RADICAL SCAVENGING;

ELECTRON TRANSPORT; ELECTRONS; FLAVONOIDS; FREE RADICAL SCAVENGERS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PROTONS;

EID: 84891537737     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2013.12.025     Document Type: Article

References (40)

1. D. Amić, and B. Lučić Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids Bioorganic and Medicinal Chemistry 18 1 2010 28 35
2. D. Amić, V. Stepanić, B. Lučić, Z. Marković, and J.M. Dimitrić Marković PM6 study of free radical scavenging mechanisms of flavonoids: Why does O-H bond dissociation enthalpy effectively represent free radical scavenging activity? Journal of Molecular Modeling 19 6 2013 2593 2603
3. E. Anouar, C.A. Calliste, P. Košinova, F. Di Meo, J.-L. Duroux, and Y. Champavier et al. Free radical scavenging properties of guaiacol oligomers: A combined experimental and quantum study of the guaiacyl-moiety role Journal of Physical Chemistry A 113 50 2009 13881 13891
4. H.M. Awad, M.G. Boersma, S. Boeren, P.J. van Bladeren, J. Vervoort, and I.M.C.M. Rietjens Structure-activity study on the quinone/quinone methide chemistry of flavonoids Chemical Research in Toxicology 14 4 2001 398 408 (Pubitemid 32367473)
5. M.G. Boersma, J. Vervoort, H. Szymusiak, K. Lemanska, B. Tyrakowska, and N. Cenas et al. Regioselectivity and reversibility of the glutathione conjugation of quercetin quinone methide Chemical Research in Toxicology 13 3 2000 185 191 (Pubitemid 30169963)
6. W. Bors, W. Heller, C. Michel, and M. Saran Flavonoids as antioxidants: Determination of radical-scavenging efficiencies L. Packer, A.N. Glazer, Methods in enzymology 1990 Academic Press San Diego 343 355 (Pubitemid 20279976)
7. S. Burda, and W. Oleszek Antioxidant and antiradical activities of flavonoids Journal of Agricultural and Food Chemistry 49 6 2001 2774 2779 (Pubitemid 32826067)
8. O. Dangles Antioxidant activity of plant phenols: Chemical mechanisms and biological significance Current Organic Chemistry 16 6 2012 692 714
9. F. Di Meo, V. Lemaur, J. Cornil, R. Lazzaroni, J.-L. Duroux, and Y. Olivier et al. Free radical scavenging by natural polyphenols: Atom versus electron transfer Journal of Physical Chemistry A 117 10 2013 2082 2092
10. Y. Feng, L. Liu, J.-T. Wang, H. Huang, and Q.-X. Guo Assessment of experimental bond dissociation energies using composite ab initio methods and evaluation of the performances of density functional methods in the calculation of bond dissociation energies Journal of Chemical Information and Computer Sciences 43 6 2003 2005 2013
11. S. Fiourucci, J. Golebiowski, D. Cabrol-Bass, and S. Antonczak 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
12. M.C. Foti, C. Daquino, G.A. DiLabio, and K.U. Ingold Kinetics of the oxidation of quercetin by 2,2-diphenyl-1-picrylhydrazyl (dpph) Organic Letters 13 18 2011 4826 4829
13. C.G. Fraga, M. Galleano, S.V. Verstraeten, and P.I. Oteiza Basic biochemical mechanisms behind the health benefits of polyphenols Molecular Aspects of Medicine 31 6 2010 435 445
14. S. Hammes-Schiffer, and A.A. Stuchebrukhov Theory of coupled electron and proton transfer reactions Chemical Reviews 110 12 2010 6939 6960
15. B.H. Havsteen The biochemistry and medical significance of the flavonoids Pharmacology & Therapeutics 96 2-3 2002 67 202 (Pubitemid 35356564)
16. S.V. Jovanovic, S. Steenken, M. Tosic, B. Marjanovic, and M.G. Simic Flavonoids as antioxidants Journal of the American Chemical Society 116 11 1994 4846 4851 (Pubitemid 24255827)
17. E. Klein, V. Lukeš, and M. Ilčin DFT/B3LYP study of tocopherols and chromans antioxidant action energetics Chemical Physics 336 1 2007 51 57
18. M. Leopoldini, N. Russo, and M. Toscano Gas and liquid phase acidity of natural antioxidants Journal of Agricultural and Food Chemistry 54 8 2006 3078 3085
19. M. Leopoldini, N. Russo, and M. Toscano The molecular basis of working mechanisms of natural polyphenolic antioxidants Food Chemistry 125 2 2011 288 306
20. G. Litwinienko, and K.U. Ingold Abnormal solvent effects on hydrogen atom abstractions. 1. The reactions of phenols with 2,2-diphenyl-1-picrylhydrazyl (dpph) in alcohols Journal of Organic Chemistry 68 9 2003 3433 3438 (Pubitemid 36520361)
21. G. Litwinienko, and K.U. Ingold Solvent effects on the rates and mechanisms of reaction of phenols with free radicals Accounts of Chemical Research 40 3 2007 222 230
22. M. Lucarini, V. Mugnaini, and G.F. Pedulli Bond dissociation enthalpies of polyphenols: The importance of cooperative effects Journal of Organic Chemistry 67 3 2002 928 931 (Pubitemid 34135698)
23. Z. Marković, D. Milenković, J. Crossed D signorović, J.M. Dimitrić Marković, V. Stepanić, and B. Lučić et al. PM6 and DFT study of free radical scavenging activity of morin Food Chemistry 134 4 2012 1754 1760
24. D.B. McPhail, R.C. Hartley, P.T. Gardner, and G.G. Duthie Kinetic and stoichiometric assessment of the antioxidant activity of flavonoids by electron spin resonance spectroscopy Journal of Agricultural and Food Chemistry 51 6 2003 1684 1690
25. A. Mohajeri, and S.S. Asemani Theoretical investigation on antioxidant activity of vitamins and phenolic acids for designing a novel antioxidant Journal of Molecular Structure 930 1-3 2009 15 20
26. MOPAC2012. Available on-line from http://openmopac.net/MOPAC2012.html.
27. P. Mulder, O.W. Saastad, and D. Griller O-H bond dissociation energies in para-substituted phenols Journal of the American Chemical Society 110 12 1988 4090 4092
28. M. Musialik, R. Kuzmicz, T.S. Pawlowski, and G. Litwinienko Acidity of hydroxyl groups: An overlooked influence on antiradical properties of flavonoids Journal of Organic Chemistry 74 7 2009 2699 2709
29. A.S. Pannala, T.S. Chan, P.J. O'Brien, and C.A. Rice-Evans Flavonoid B-ring chemistry and antioxidant activity: Fast reaction kinetics Biochemical and Biophysical Research Communications 282 5 2001 1161 1168 (Pubitemid 32912847)
30. J. Rimarčik, V. Lukeš, E. Klein, and M. Ilčin 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
31. R. Sokolova, Š. Ramešova, I. Degano, M. Hromadova, M. Gal, and J. Žabka The oxidation of natural flavonoid quercetin Chemical Communications 48 28 2012 3433 3435
32. V. Stepanić, K. Gall Trošelj, B. Lučić, Z. Marković, and D. Amić Bond dissociation free energy as a general parameter for flavonoid radical scavenging activity Food Chemistry 141 2 2013 1562 1570
33. J.J.P. Stewart Optimization of parameters for semiempirical methods VI: More modifications to the NDDO approximations and re-optimization of parameters Journal of Molecular Modeling 19 1 2013 1 32
34. T. Tu, D. Giblin, and M.L. Gross Structural determinant of chemical reactivity and potential health effects of quinones from natural products Chemical Research in Toxicology 24 9 2011 1527 1539
35. A. Vaganek, J. Rimarčik, V. Lukeš, and E. Klein On the energetics of homolytic and heterolytic O-H bond cleavage in flavonoids Computational and Theoretical Chemistry 991 2012 192 200
36. D.R. Weinberg, C.J. Gagliardi, J.F. Hull, C.F. Murphy, C.A. Kent, and B.C. Westlake et al. Proton-coupled electron transfer Chemical Reviews 112 7 2012 4016 4093
37. A.S. Woldu, and J. Mai A novel relationship between the radical-scavenging activity of flavonoids and enthalpy of formation revealed with Hartree-Fock computations and thermochemical deduction Redox Report 17 3 2012 115 130
38. J.S. Wright, E.R. Johnson, and G.A. DiLabio Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants Journal of the American Chemical Society 123 6 2001 1173 1183 (Pubitemid 32148182)
39. X.-Q. Yao, X.-J. Hou, H. Jiao, H.-W. Xiang, and Y.-W. Li Accurate calculations of bond dissociation enthalpies with density functional methods Journal of Physical Chemistry A 107 46 2003 9991 9996
40. H.-Y. Zhang Selection of theoretical parameter characterizing scavenging activity of antioxidants on free radicals Journal of the American Oil Chemists' Society 75 12 1998 1705 1709 (Pubitemid 128607934)