Evaluation of the antiradical properties of phenolic acids

International Journal of Molecular Sciences

Volumn 15, Issue 9, 2014, Pages 16351-16380

  Koroleva, Olga ^a   Torkova, Anna ^a   Nikolaev, Ilya ^a   Khrameeva, Ekaterina ^b   Fedorova, Tatyana ^a   Tsentalovich, Mikhail ^a   Amarowicz, Ryszard ^c  

^a BACH INSTITUTE OF BIOCHEMISTRY   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c INSTITUTE OF ANIMAL REPRODUCTION AND FOOD RESEARCH   (Poland)

Author keywords

Antioxidant descriptors; Antioxitant capacity; Phenolic acids; Quantum chemical calculations

Indexed keywords

2, 2' AZINOBIS (3 ETHYLBENZOTHIAZOLINE 6 SULFONIC ACID); 4 HYDROXYBENZOIC ACID; FERULIC ACID; GALLIC ACID; HYDROXYACID; P HYDROXYCINNAMIC ACID; PARA COUMARIC ACID; PEROXY RADICAL; SINAPIC ACID; SYRINGIC ACID; UNCLASSIFIED DRUG; VANILLIC ACID; 4 HYDROXYBENZOIC ACID ESTER; 4-COUMARIC ACID; 4-HYDROXYBENZOIC ACID; ANTIOXIDANT; COUMARIC ACID; HYDROXYBENZOIC ACID DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; BOND DISSOCIATION ENERGY; CHEMICAL BOND; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; COMPUTER PROGRAM; ELECTRON TRANSPORT; ELECTRONEGATIVITY; ELECTROPHILICITY; ENTHALPY; GEOMETRY; HOMO ENERGY; IONIZATION; IONIZATION POTENTIAL; KINETICS; LUMO ENERGY; MULLIKEN CHARGE; ORAC ASSAY; ORAC-FL ASSAY; PH; PROTON AFFINITY; PROTON DISSOCIATION ENTHALPY; QUANTUM CHEMISTRY; RIGIDITY; ALGORITHM; CHEMISTRY; QUANTUM THEORY;

ALGORITHMS; ANTIOXIDANTS; COUMARIC ACIDS; HYDROGEN-ION CONCENTRATION; HYDROXYBENZOATES; KINETICS; PARABENS; QUANTUM THEORY; SOFTWARE;

EID: 84907228580     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms150916351     Document Type: Article

References (68)

1. Arts, I.C.W.; Hollman, P.C.H. Polyphenols and desiase risk in epidemiologic studies. Am. J. Clin. Nutr. 2005, 81, S317-S325.
2. Skulachev, V.P. A biochemical approach to the problem of aging: "Megaproject" on membrane-penetrating ions. The first results and prospects. Biochemisty 2007, 72, 1385-1396.
3. Knasmuller, S.; Nersesyan, A.; Mišík, M.; Gerner, C.; Mikulits, W.; Ehrlich, V.; Hoelzl, C.; Szakmary, A.; Wagner, K.H. Use of conventional and -omics based methods for health claims of dietary antioxidants: A critical overview. Br. J. Nutr. 2008, 99, ES3-ES52.
4. Simin, N.; Orcic, D.; Cetojevic-Simin, D.; Mimica-Dukic, N.; Anackov, G.; Beara, I.; Mitic-Culafic, D.; Bozin, B. Phenolic profile, antioxidant, anti-inflammatory and cytotoxicactivities of small yellow onion (Allium flavum L. subsp. flavum, Alliaceae). LWT-Food Sci. Technol. 2013, 54, 139-146.
5. Stevanato, R.; Bertelle, M.; Fabris S. Photoprotective characteristics of natural antioxidant polyphenols. Regul. Toxicol. Pharmacol. 2014, 69, 71-77.
6. Roy, A.J.; Prince, P.S.M. Preventive effects of p-coumaric acid on lysosomal dysfunction and myocardial infarct size in experimentally induced myocardial infarction. Eur. J. Pharmacol. 2013, 699, 33-39.
7. Frankel, E.N.; Finley, J.W. How to standardize the multiplicity of methods to evaluate natural antioxidants. J. Agric. Food Chem. 2008, 56, 4901-4908.
8. Urbaniak, A.; Molski, M.; Szeląg, M. Quantum-chemical calculations of the antioxidant properties of trans-p-coumaric acid and trans-sinapinic acid. Comput. Methods Sci. Technol. 2012, 18, 117-128.
9. Urbaniak, A.; Szeląg, M.; Molski, M. Theoretical investigation of stereochemistry and solvent influence on antioxidant activity of ferulic acid. Comp. Theoret. Chem. 2013, 1012, 33-40.
10. Franck, T.; Mouithys-Mickalad, A.; Robert, T.; Ghitti, G.; Deby-Dupont, G.; Neven, P.; Serteyn, D. Differentiation between stoichiometric and anticatalytic antioxidant properties of benzoic acid analogues: A structure/redox potential relationship study. Chem. Biol. Int. 2013, 206, 194-203.
11. Leopoldini, M.; Russo, N.; Toscano, M. The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chem. 2011, 125, 288-306.
12. Foti, M.C.; Daquino, C.; Geraci, C. Electron-transfer reaction of cinnamic acids and their methyl esters with the DPPH radical in alcoholic solutions. J. Org. Chem. 2004, 69, 2309-2314.
13. Litwinienko, G.; Ingold, K.U.; Solvent effects on the rates and mechanisms of reaction of phenols with free radicals. Acc. Chem. Res. 2007, 40, 222-230.
14. Klein, E.; Rimarcik, J.; Lukes, V. DFT/B3LYP Study of the O-H bond dissociation enthalpies and proton affinities of para- and meta-substituted phenols in water and benzene. Acta Chim. Slovaca 2009, 2, 37-51.
15. Wright, J.S.; Johnson, E.R.; DiLabio, G.A. Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants. J. Am. Chem. Soc. 2001, 123, 1173-1183.
16. Vafiadis, A.P; Bakalbassis, E.G. A DFT study on the deprotonation antioxidant mechanistic step of ortho-substituted phenolic cation radicals. Chem. Phys. 2005, 316, 195-204.
17. Klein, E.; Lukes, V. DFT/B3LYP study of the substituent effect on the reaction enthalpies of the individual steps of sequential proton loss electron transfer mechanism of phenols antioxidant action: Correlation with phenolic C-O bond length. J. Mol. Struct. 2007, 805, 153-160.
18. Klein, E.; Lukes, V. DFT/B3LYP study of the substituent effect on the reaction enthalpies of the individual steps of single electron transfer-proton transfer and sequential proton loss electron transfer mechanisms of phenols antioxidant action. J. Phys. Chem. 2006, 110, 12312-12320.
19. Barclay, L.R.C.; Vinqvist, M.R. Phenols as Antioxidants. In The Chemistry of Phenols; Rappoport, Z., Ed.; John Wiley & Sons, Ltd.: Chichester, UK, 2003; pp. 839-908.
20. Justino, G.C.; Vieira, A.J.S.C. Antioxidant mechanisms of quercetin and myricetin in the gas phase and in solution-A comparison and validation of semi-empirical methods. J. Mol. Model. 2010, 16, 863-876.
21. Russo, N.; Toscano, M.; Ucella, N. Semiempirical molecular modeling into quercetin reactive site: Structural, conformational and electronic features. J. Agric. Food Chem. 2000, 48, 3232-3237.
22. Lemanska, K.; Szymusiak, H.; Tyrakowska, B.; Zieliński, R.; Soffers Ans, E.M.F.; Rietjens Ivonne, M.C.M. The influence of pH on antioxidant properties and the mechanism of antioxidant action of hydroxyflavones. Free Radic. Biol. Med. 2001, 31, 869-881.
23. Huang, D.; Ou, B.; Prior, R.L. The chemistry behind antioxidant capacity assay. J. Agric. Food Chem. 2005, 53, 1841-1856.
24. Moon, J.K.; Shibamoto, T. Antioxidant assays for plant and food components. J. Agric. Food. Chem. 2009, 57, 1655-1666.
25. Bors, W.; Michel, C.; Saran, M. Inhibition of the bleaching of the carotenoid crocin. A rapid test for quantifying antioxidant activity. Biochim. Biophys. Acta 1984, 796, 312-319.
26. Apak, R.; Güçlü, K.; Demirata, B.; Özyürek, M.; Çelik, S.E.; Bekta-oğlu, B.; Berker, K.I.; Özyurt, D. Comparative evaluation of various total antioxidant capacity assays applied to phenolic compounds with the CUPRAC assay. Molecules 2007, 12, 1496-1547.
27. Benzie, I.F.F.; Strain, J.J. The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power": The FRAP assay. Anal. Biochem. 1996, 239, 70-76.
28. Cao, G.; Alessio, H.M.; Cutler, R.G. Oxygen-radical absorbance capacity assay for antioxidants. Free Radic. Biol. Med. 1993, 14, 303-311.
29. Miller, N.J.; Rice-Evans, C.A.; Davies, M.J.; Gopinathan, V.; Milner, A. A novel method for measuring antioxidant capacity and its application to monitoring the antioxidant status in premature neonates. Clin. Sci. 1993, 84, 407-412.
30. Wayner, D.D.M.; Burton, G.W.; Ingold, K.U.; Locke, S. Quantitative measurement of the total, peroxyl radical-trapping antioxidant capability of human blood plasma by controlled peroxidation: The important contribution made by plasma proteins. FEBS Lett. 1985, 187, 33-37.
31. Re, R.; Pelegrini, R.; Proteggente, A.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med. 1999, 26, 1231-1237.
32. Brand-Williams, W.; Cuvelier, M.E.; Berset, C. Use of a free radical method to evaluate antioxidant activity. LWT-Food Sci. Technol. 1995, 28, 25-30.
33. Blois, M.S. Antioxidant determinations by the use of a stable free radical. Nat. Rev. Drug Discov. 1958, 181, 1199-1200.
34. Smirnoff, N.; Cumbes, Q.J. Hydroxyl radical scavenging activity of compatible solutes. Phytochemistry 1989, 28, 1057-1060.
35. Beers, J.R.F.; Sizer, I.W. Colorimetric method for estimation of catalase. J. Biol. Chem. 1952, 195, 133-140.
36. Kooy, N.W.; Royall, J.A.; Ischiropoulos, H.; Beckman, J.S. Peroxynitrite-mediated oxidation of dihydrorhodamine 123. Free Radic. Biol. Med. 1994, 16, 149-156.
37. Wilkinson, F.; Helman, W.P.; Ross, A.B. Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. J. Phys. Chem. Ref. Data 1995, 24, 663-1021.
38. Milde, J.; Elstner, E.F.; Graßmann, J. Synergistic effects of phenolics and carotenoids on human low-density lipoprotein oxidation. Mol. Nutr. Food Res. 2007, 51, 956-961.
39. Natella, F.; Nardini, M.; di Felice, M.; Scaccini, C. Benzoic and cinnamic acids derivatives as antioxidants: Structure-activity relation. J. Agric. Food Chem. 1999, 47, 1453-1459.
40. Rao, M.S.; Muralikrishna, G. Evaluation of the antioxidant properties of free and bound phenolic acids from native and malted millet (Ragi, Eleusine. coracano Indaf-15). J. Agric. Food Chem. 2002, 50, 889-892.
41. Gomez-Ruiz, J.A.; Leake D.S.; Amines, J.M. In vitro antioxidant capacity of coffee compounds and their metabolites. J. Agric. Food Chem. 2007, 55, 6962-6969.
42. Davalos, A.; Gomez-Cordoves, C.; Bartolome, B. Extending applicability of the oxygen radical absorbance capacity (ORAC-Fluorescein) assay. J. Agric. Food Chem. 2004, 52, 48-54.
43. Nenadis, N.; Lazaridou, O.; Tsimidou, M.Z. Use of reference compounds in antioxidant activity assays. J. Agric. Food Chem. 2007, 55, 5452-5460.
44. Alamed, J.; Chaiyasit, W.; McClements, D.J.; Decker, E.A. Relationships between free radical scavenging and antioxidant activity of foods. J. Agric. Food Chem. 2009, 57, 2969-2976.
45. Gismondi, A.; Canuti, L.; Grispo, M.; Canini, A. Biochemical composition and antioxidant properties of Lavandula angustifolia Miller essential oil are shielded by propolis against UV radiations. Photochem. Photobiol. 2014, 90, 702-708.
46. Yen, C.T.; Yen, G.C. Effects of phenolic acids on human phenolsulphotransferases in relation to their antioxidant capacity. J. Agric. Food Chem. 2003, 51, 1474-1479.
47. Tyrakowska, B.; Soffers, A.E.M.F.; Szymusiak, H.; Boeren, S.; Boersma, M.G.; Lemańska, K.; Vervoort, J.; Rietjens, I.M.C.M. TEAC antioxidant activity of 4-hydroxybenzoates. Free Radic. Biol. Med. 1999, 27, 1427-1436.
48. Amorati, R.; Pedulli, G.F.; Cabrini, L.; Zambonin, L.; Landi, L. Solvent and pH effects on the antioxidant activity of caffeic and other phenolic acids. J. Agric. Food Chem. 2006, 54, 2932-2937.
49. Pannala, S.A.; Chan, T.S.; O'Brien, P.J.; Catherine A. Rice-Evans, C.A. Flavanoid B-ring chemistry and antioxidant activity: Fast reaction kinetics. Biochem. Biophys. Res. Commun. 2001, 282, 1161-1168.
50. Munoz-Munoz, J.L.; Garcia-Molina, F.; Varon, R.; Tudela, J.; García-Cánovas, F.; Rodriguez-Lopez, J.N. Quantification of the antioxidant capacity of different molecules and their kinetic antioxidant efficiencies. J. Agric. Food Chem. 2010, 58, 2062-2070.
51. Gismondi, A.; Serio, M.; Canuti, L.; Canini, A. Biochemical, antioxidant and antineoplastic properties of Italian saffron (Crocus sativus L.). Am. J. Plant Sci. 2012, 3, 1573-1580.
52. Pellegrini, N.; Visioli, F.; Buratti, S.; Brighenti, F. Direct analysis of total antioxidant activity of olive oil and studies on the influence of heating. J. Agric. Food Chem. 2001, 49, 2532-2538.
53. Nenadis, N.; Wang, L.F.; Tsimidou, M.; Zhang, H.Y. Estimation of scavenging activity of phenolic compounds using the ABTS+ assay. J. Agric. Food Chem. 2004, 52, 4669-4674.
54. Martynova, K.V.; Andreeva, L.A.; Klimova, P.A.; Kirillova, U.G.; Shevchenko, V.P.; Nagaev, I.U.; Shrum, S.I.; Shvets, V.I.; Myasoedov, N.F. Structure-functional study of glycine and proline-containing peptides (gliprolinov) as potential neuroprotectors. Russ. J. Bioorg. Chem. 2009, 35, 165-171.
55. Davies, M.J.; Forni, L.G.; Wilson, R.L. Vitamin E analogue Trolox C. Biochem. J. 1988, 255, 513-522.
56. Steenken, S. Transient phenoxyl radicals: Formation and properties in aqueous Solutions. In The Chemistry of Phenols; Rappoport, Z., Ed.; John Wiley & Sons, Ltd.: Chichester, UK, 2003; pp. 1107-1151.
57. Zhan, C.G.; Nichos, J.A.; Dixon, D.A. Ionization potential, electron affinity, electronegativity, hardness, and electron excitation energy: Molecular properties from density functional theory orbital energies. J. Phys. Chem. 2003, 107, 4184-4195.
58. Correria, C.F.; Guedes, R.C.; Borges dos Santos, R.M.; Costa Cabral, B.J.; Martinho Simões, J.A. O-H bond dissociation enthalpies in hydroxyphenols; a time resolved photoacoustic calorimetry and quantum chemistry study. Phys. Chem. 2004, 6, 2109-2118.
59. Belaya, N.I.; Ovcharova, O.Y.; Nikolaevskii, A.N.; Filippenko, T.A.; Zaets, V.A. Effect of the structure of phenols on their activity in the reaction with ethylbenzene radicals. Theoret. Exp. Chem. 2004, 40, 234-240.
60. Wright, J.S.; Carpenter, D.J.; McKay, D.J.; Ingold, K.U. Theoretical calculation of substituent effects on the O-H bond strength of phenolic antioxidants related to vitamin E. J. Am. Chem. Soc. 1997, 119, 4245-4252.
61. Fazari, A.E.; Ju, Y.H. Nonaqueous solution studies on the protonation equlibria of some phenolic acids. J. Sol. Chem. 2008, 37, 1305-1319.
62. Tompson, M.J.; Zeegers, P.J. A theoretical study of the two-phase nitration of phenol. Tetrahedron 1989, 45, 191-202.
63. Klein, E. Study of gas-phase O-H bond dissociation enthalpies and ionization potentials of substituted phenols-Applicability of ab initio and DFT/B3LYP methods. Chem. Phys. 2006, 330, 515-525.
64. Ou, B.; Hampsch-Woodill, M.; Prior, R.L. Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe. J. Agric. Food Chem. 2001, 49, 4619-4626.
65. Moore, J.; Cheng, Z.; Su, L.; Yu, L. Effects of solid-state enzymatic treatments on the antioxidant properties of wheat bran. J. Agric. Food Chem. 2006, 54, 9032-9045.
66. Prior, R.L.; Hoang, H.; Gu, L.; Wu, X.; Bacchiocca, M.; Howard, L.; Hampsch-Woodill, M.; Huang, D.; Ou, B.; Jacob, R. Assays for hydrophilic and lipophilic antioxidant capacity (oxygen radical absorbance (ORACFL)) of plasma and other biological and food samples. J. Agric Food Chem. 2003, 51, 3273-3279.
67. Lide, D.A. CRC Handbook Chemistry and Physics; CRC Press Inc.: Boca Raton, FL, USA, 2004; p. 2712.
68. Tyunina, E.Yu.; Badelin, V.G. Molecular descriptors of amino acids for the evaluation of the physicochemical parameters and biological activity of peptides. Russ. J. Bioorg. Chem. 2009, 35, 453-460.