메뉴 건너뛰기




Volumn 60, Issue 14, 2012, Pages 3693-3699

DPPH radical scavenging activity of tricin and its conjugates isolated from "njavara" rice bran: A density functional theory study

Author keywords

antioxidants; bond dissociation enthalpy; density functional theory; DPPH radical scavenging activity; ionization potential; proton affinity; spin density

Indexed keywords

ANTIOXIDANTS; BOND DISSOCIATION ENTHALPIES; PROTON AFFINITY; RADICAL SCAVENGING ACTIVITY; SPIN DENSITIES;

EID: 84859571558     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf204826e     Document Type: Article
Times cited : (46)

References (45)
  • 1
    • 0030897739 scopus 로고    scopus 로고
    • Genetic and functional changes in mitochondria associated with aging
    • Ozawa, T. Genetic and functional changes in mitochondria associated with aging Physiol. Rev. 1997, 77, 425-464
    • (1997) Physiol. Rev. , vol.77 , pp. 425-464
    • Ozawa, T.1
  • 2
    • 0031916984 scopus 로고    scopus 로고
    • The free radical theory of aging matures
    • Beckman, K. B.; Ames, B. N. The free radical theory of aging matures Physiol. Rev. 1998, 78, 547-581
    • (1998) Physiol. Rev. , vol.78 , pp. 547-581
    • Beckman, K.B.1    Ames, B.N.2
  • 4
    • 0034969156 scopus 로고    scopus 로고
    • Masking of antioxidant capacity by the interaction of flavonoids with protein
    • Arts, M. J. T. J.; Haenen, G. R. M. M.; Voss, H. P.; Bast, A. Masking of antioxidant capacity by the interaction of flavonoids with protein Food Chem. Toxicol. 2001, 39, 787-791
    • (2001) Food Chem. Toxicol. , vol.39 , pp. 787-791
    • Arts, M.J.T.J.1    Haenen, G.R.M.M.2    Voss, H.P.3    Bast, A.4
  • 5
    • 0029888128 scopus 로고    scopus 로고
    • Structure-antioxidant activity relationships of flavonoids and phenolic acids
    • Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids Free Radical Biol. Med. 1996, 20, 933-956
    • (1996) Free Radical Biol. Med. , vol.20 , pp. 933-956
    • Rice-Evans, C.A.1    Miller, N.J.2    Paganga, G.3
  • 7
    • 79955064616 scopus 로고    scopus 로고
    • Isolation, characterization and quantification of tricin and flavonolignans in the medicinal rice Njavara (Oryza sativa L.), as compared to staple varieties
    • Mohanlal, S.; Parvathy, R.; Shalini, V.; Helen, A.; Jayalekshmy, A. Isolation, characterization and quantification of tricin and flavonolignans in the medicinal rice Njavara (Oryza sativa L.), as compared to staple varieties Plant Foods Hum. Nutr. 2011, 66, 91-96
    • (2011) Plant Foods Hum. Nutr. , vol.66 , pp. 91-96
    • Mohanlal, S.1    Parvathy, R.2    Shalini, V.3    Helen, A.4    Jayalekshmy, A.5
  • 8
    • 0036774226 scopus 로고    scopus 로고
    • Flavonoid antioxidants: Chemistry, metabolism and structure-activity relationships
    • Heim, K. E.; Tagliaferro, A. R.; Bobilya, D. J. Flavonoid antioxidants: Chemistry, metabolism and structure-activity relationships J. Nutr. Biochem. 2002, 13, 572-584
    • (2002) J. Nutr. Biochem. , vol.13 , pp. 572-584
    • Heim, K.E.1    Tagliaferro, A.R.2    Bobilya, D.J.3
  • 9
    • 68749089699 scopus 로고    scopus 로고
    • Dissociation energies of O-H bonds in natural antioxidants
    • Denisova, T. G.; Denisov, E. T. Dissociation energies of O-H bonds in natural antioxidants Russ. Chem. Bull. 2008, 57, 1858-1866
    • (2008) Russ. Chem. Bull. , vol.57 , pp. 1858-1866
    • Denisova, T.G.1    Denisov, E.T.2
  • 10
    • 34547106285 scopus 로고    scopus 로고
    • Evaluation of the ability of antioxidants to counteract lipid oxidation: Existing methods, new trends and challenges
    • Laguerre, M.; Lecomte, J.; Villeneuve, P. Evaluation of the ability of antioxidants to counteract lipid oxidation: Existing methods, new trends and challenges Prog. Lipid Res. 2007, 46, 244-282
    • (2007) Prog. Lipid Res. , vol.46 , pp. 244-282
    • Laguerre, M.1    Lecomte, J.2    Villeneuve, P.3
  • 11
    • 31844444029 scopus 로고    scopus 로고
    • A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: The specificity of the 3-OH site
    • Trouillas, P.; Marsal, P.; Siri, D.; Lazzaroni, R.; Duroux, J. L. A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: The specificity of the 3-OH site Food Chem. 2006, 97, 679-688
    • (2006) Food Chem. , vol.97 , pp. 679-688
    • Trouillas, P.1    Marsal, P.2    Siri, D.3    Lazzaroni, R.4    Duroux, J.L.5
  • 12
    • 0035857407 scopus 로고    scopus 로고
    • Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants
    • 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
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1173-1183
    • Wright, J.S.1    Johnson, E.R.2    Dilabio, G.A.3
  • 14
    • 3242723376 scopus 로고    scopus 로고
    • A theoretical study of the conformational behavior and electronic structure of taxifolin correlated with the free radical-scavenging activity
    • Trouillas, P.; Fagnère, C.; Lazzaroni, R.; Calliste, C.; Marfak, A.; Duroux, J. L. A theoretical study of the conformational behavior and electronic structure of taxifolin correlated with the free radical-scavenging activity Food Chem. 2004, 88, 571-582
    • (2004) Food Chem. , vol.88 , pp. 571-582
    • Trouillas, P.1    Fagnère, C.2    Lazzaroni, R.3    Calliste, C.4    Marfak, A.5    Duroux, J.L.6
  • 15
    • 84962429291 scopus 로고    scopus 로고
    • Antioxidant properties of phenolic compounds: H-atom versus electron transfer mechanism
    • Leopoldini, M.; Marino, T.; Russo, N.; Toscano, M. Antioxidant properties of phenolic compounds: H-atom versus electron transfer mechanism J. Phys. Chem. A 2004, 108, 4916-4922
    • (2004) J. Phys. Chem. A , vol.108 , pp. 4916-4922
    • Leopoldini, M.1    Marino, T.2    Russo, N.3    Toscano, M.4
  • 16
    • 34247894012 scopus 로고    scopus 로고
    • DFT study of quercetin activated forms involved in antiradical, antioxidant, and prooxidant biological processes
    • Fiorucci, S.; Golebiowski, J.; Cabrol-Bass, D.; Antonczak, S. DFT study of quercetin activated forms involved in antiradical, antioxidant, and prooxidant biological processes J. Agric. Food Chem. 2007, 55, 903-911
    • (2007) J. Agric. Food Chem. , vol.55 , pp. 903-911
    • Fiorucci, S.1    Golebiowski, J.2    Cabrol-Bass, D.3    Antonczak, S.4
  • 17
    • 34249088888 scopus 로고    scopus 로고
    • Lone pair-π and π-π interactions play an important role in proton-coupled electron transfer reactions
    • DiLabio, G. A.; Johnson, E. R. Lone pair-π and π-π interactions play an important role in proton-coupled electron transfer reactions J. Am. Chem. Soc. 2007, 129, 6199-6203
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 6199-6203
    • Dilabio, G.A.1    Johnson, E.R.2
  • 18
    • 0037039923 scopus 로고    scopus 로고
    • Bond dissociation enthalpies of polyphenols: The importance of cooperative effects
    • Lucarini, M.; Mugnaini, V.; Pedulli, G. F. Bond dissociation enthalpies of polyphenols: The importance of cooperative effects J. Org. Chem. 2002, 67, 928-931
    • (2002) J. Org. Chem. , vol.67 , pp. 928-931
    • Lucarini, M.1    Mugnaini, V.2    Pedulli, G.F.3
  • 19
    • 27444446027 scopus 로고    scopus 로고
    • Abnormal solvent effects on hydrogen atom abstraction. 3. Novel kinetics in sequential proton loss electron transfer chemistry
    • Litwinienko, G.; Ingold, K. U. Abnormal solvent effects on hydrogen atom abstraction. 3. Novel kinetics in sequential proton loss electron transfer chemistry J. Org. Chem. 2005, 70, 8982-8990
    • (2005) J. Org. Chem. , vol.70 , pp. 8982-8990
    • Litwinienko, G.1    Ingold, K.U.2
  • 20
    • 0037414534 scopus 로고    scopus 로고
    • Abnormal solvent effects on hydrogen atom abstractions. 1. The reactions of phenols with 2,2-diphenyl-1-picrylhydrazyl (dpph•) in alcohols
    • Litwinienko, G.; Ingold, K. U. Abnormal solvent effects on hydrogen atom abstractions. 1. The reactions of phenols with 2,2-diphenyl-1-picrylhydrazyl (dpph•) in alcohols J. Org. Chem. 2003, 68, 3433-3438
    • (2003) J. Org. Chem. , vol.68 , pp. 3433-3438
    • Litwinienko, G.1    Ingold, K.U.2
  • 21
    • 0034852901 scopus 로고    scopus 로고
    • Antioxidant mechanism of flavonoids. Solvent effect on rate constant for chain-breaking reaction of quercetin and epicatechin in autoxidation of methyl linoleate
    • Pedrielli, P.; Pedulli, G. F.; Skibsted, L. H. Antioxidant mechanism of flavonoids. Solvent effect on rate constant for chain-breaking reaction of quercetin and epicatechin in autoxidation of methyl linoleate J. Agric. Food Chem. 2001, 49, 3034-3040
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 3034-3040
    • Pedrielli, P.1    Pedulli, G.F.2    Skibsted, L.H.3
  • 22
    • 2442417429 scopus 로고    scopus 로고
    • Density functional computations of the energetic and spectroscopic parameters of quercetin and its radicals in the gas phase and in solvent
    • Leopoldini, M.; Marino, T.; Russo, N.; Toscano, M. Density functional computations of the energetic and spectroscopic parameters of quercetin and its radicals in the gas phase and in solvent Theor. Chem. Acc. 2004, 111, 210-216
    • (2004) Theor. Chem. Acc. , vol.111 , pp. 210-216
    • Leopoldini, M.1    Marino, T.2    Russo, N.3    Toscano, M.4
  • 23
    • 3042786057 scopus 로고    scopus 로고
    • Solvent effect on quercetin antioxidant capacity
    • Pinelo, M.; Manzocco, L.; Nuñez, M. J.; Nicoli, M. C. Solvent effect on quercetin antioxidant capacity Food Chem. 2004, 88, 201-207
    • (2004) Food Chem. , vol.88 , pp. 201-207
    • Pinelo, M.1    Manzocco, L.2    Nuñez, M.J.3    Nicoli, M.C.4
  • 24
    • 15544369623 scopus 로고    scopus 로고
    • A theoretical study of the different radical-scavenging activities of catechin, quercetin, and a rationally designed planar catechin
    • Wang, L. F.; Zhang, H. Y. A theoretical study of the different radical-scavenging activities of catechin, quercetin, and a rationally designed planar catechin Bioorg. Chem. 2005, 33, 108-115
    • (2005) Bioorg. Chem. , vol.33 , pp. 108-115
    • Wang, L.F.1    Zhang, H.Y.2
  • 26
    • 84962433222 scopus 로고    scopus 로고
    • The molecular basis of working mechanism of natural polyphenolic antioxidants
    • Leopoldini, M.; Russo, N.; Toscano, M. The molecular basis of working mechanism of natural polyphenolic antioxidants Food Chem. 2011, 125, 288-306
    • (2011) Food Chem. , vol.125 , pp. 288-306
    • Leopoldini, M.1    Russo, N.2    Toscano, M.3
  • 27
    • 0034868284 scopus 로고    scopus 로고
    • O-H bond dissociation energies of phenolic compounds are determined by field/inductive effect or resonance effect? A DFT study and its implication
    • Zhang, H. Y.; Sun, Y. M.; Chen, D. Z. O-H bond dissociation energies of phenolic compounds are determined by field/inductive effect or resonance effect? A DFT study and its implication Quant. Struct.-Act. Relat. 2001, 20, 148-152
    • (2001) Quant. Struct.-Act. Relat. , vol.20 , pp. 148-152
    • Zhang, H.Y.1    Sun, Y.M.2    Chen, D.Z.3
  • 28
    • 0037455262 scopus 로고    scopus 로고
    • Substituent effects on O-H bond dissociation enthalpies and ionization potentials of catechols: A DFT study and its implications in the rational design of phenolic antioxidants and elucidation of structure - Activity relationships for flavonoid antioxidants
    • Zhang, H. Y.; Sun, Y. M.; Wang, X. L. Substituent effects on O-H bond dissociation enthalpies and ionization potentials of catechols: A DFT study and its implications in the rational design of phenolic antioxidants and elucidation of structure-Activity relationships for flavonoid antioxidants Chem.-Eur. J. 2003, 9, 502-508
    • (2003) Chem.-Eur. J. , vol.9 , pp. 502-508
    • Zhang, H.Y.1    Sun, Y.M.2    Wang, X.L.3
  • 29
    • 42149135365 scopus 로고    scopus 로고
    • Electronic description of four flavonoids revisited by DFT method
    • Antonczak, S. Electronic description of four flavonoids revisited by DFT method J. Mol. Struct. (THEOCHEM) 2008, 856, 38-45
    • (2008) J. Mol. Struct. (THEOCHEM) , vol.856 , pp. 38-45
    • Antonczak, S.1
  • 30
    • 37849001244 scopus 로고    scopus 로고
    • 13C CP MAS NMR and GIAO-CHF/DFT calculations of flavonoids: Morin, kaempferol, tricin, genistein, formononetin and 3,7-dihydroxyflavone
    • Zielińska, A.; Paradowska, K.; Jakowski, J.; Wawer, I. 13C CP MAS NMR and GIAO-CHF/DFT calculations of flavonoids: Morin, kaempferol, tricin, genistein, formononetin and 3,7-dihydroxyflavone J. Mol. Struct. 2008, 873, 109-116
    • (2008) J. Mol. Struct. , vol.873 , pp. 109-116
    • Zielińska, A.1    Paradowska, K.2    Jakowski, J.3    Wawer, I.4
  • 31
    • 80052733789 scopus 로고    scopus 로고
    • Kinetics of the oxidation of quercetin by 2,2-diphenyl-1-picrylhydrazyl (dpph•)
    • Foti, M. C.; Daquino, C.; Dilabio, G. A.; Ingold, K. U. Kinetics of the oxidation of quercetin by 2,2-diphenyl-1-picrylhydrazyl (dpph•) Org. Lett. 2011, 13, 4826-4829
    • (2011) Org. Lett. , vol.13 , pp. 4826-4829
    • Foti, M.C.1    Daquino, C.2    Dilabio, G.A.3    Ingold, K.U.4
  • 32
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98, 5648-5652
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 33
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 1988, 37, 785-789
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 34
    • 84961983562 scopus 로고    scopus 로고
    • Analytical free energy second derivatives with respect to nuclear coordinates: Complete formulation for electrostatic continuum solvation models
    • Mennucci, B.; Cammi, R.; Tomasi, J. Analytical free energy second derivatives with respect to nuclear coordinates: Complete formulation for electrostatic continuum solvation models J. Chem. Phys. 1999, 110, 6858-6870
    • (1999) J. Chem. Phys. , vol.110 , pp. 6858-6870
    • Mennucci, B.1    Cammi, R.2    Tomasi, J.3
  • 35
    • 84961986752 scopus 로고    scopus 로고
    • New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution
    • Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution J. Chem. Phys. 2002, 117, 43-54
    • (2002) J. Chem. Phys. , vol.117 , pp. 43-54
    • Cossi, M.1    Scalmani, G.2    Rega, N.3    Barone, V.4
  • 37
    • 1542378822 scopus 로고    scopus 로고
    • A critical evaluation of the factors determining the effect of intramolecular hydrogen bonding on the O-H bond dissociation enthalpy of catechol and of flavonoid antioxidants
    • Lucarini, M.; Pedulli, G. F.; Guerra, M. A critical evaluation of the factors determining the effect of intramolecular hydrogen bonding on the O-H bond dissociation enthalpy of catechol and of flavonoid antioxidants Chem.-Eur. J. 2004, 10, 933-939
    • (2004) Chem.-Eur. J. , vol.10 , pp. 933-939
    • Lucarini, M.1    Pedulli, G.F.2    Guerra, M.3
  • 38
    • 84962419390 scopus 로고    scopus 로고
    • Gas and liquid phase acidity of natural antioxidants
    • Leopoldini, M.; Russo, N.; Toscano, M. Gas and liquid phase acidity of natural antioxidants J. Agric. Food Chem. 2006, 54, 3078-3085
    • (2006) J. Agric. Food Chem. , vol.54 , pp. 3078-3085
    • Leopoldini, M.1    Russo, N.2    Toscano, M.3
  • 40
    • 0038005812 scopus 로고    scopus 로고
    • Hydrogen-bonding effects on the properties of phenoxyl radicals. An EPR, kinetic, and computational study
    • Lucarini, M.; Mugnaini, V.; Pedulli, G. F.; Guerra, M. Hydrogen-bonding effects on the properties of phenoxyl radicals. An EPR, kinetic, and computational study J. Am. Chem. Soc. 2003, 125, 8318-8329
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 8318-8329
    • Lucarini, M.1    Mugnaini, V.2    Pedulli, G.F.3    Guerra, M.4
  • 41
    • 0033860031 scopus 로고    scopus 로고
    • Semiempirical molecular modeling into quercetin reactive site: Structural, conformational, and electronic features
    • Russo, N.; Toscano, M.; Uccella, N. Semiempirical molecular modeling into quercetin reactive site: Structural, conformational, and electronic features J. Agric. Food Chem. 2000, 48, 3232-3237
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 3232-3237
    • Russo, N.1    Toscano, M.2    Uccella, N.3
  • 42
    • 64249121215 scopus 로고    scopus 로고
    • Acidity of hydroxyl groups: An overlooked influence on antiradical properties of flavonoids
    • Musialik, M.; Kuzmicz, R.; Pawlowski, T. S.; Litwinienko, G. Acidity of hydroxyl groups: An overlooked influence on antiradical properties of flavonoids J. Org. Chem. 2009, 74, 2699-2709
    • (2009) J. Org. Chem. , vol.74 , pp. 2699-2709
    • Musialik, M.1    Kuzmicz, R.2    Pawlowski, T.S.3    Litwinienko, G.4
  • 43
    • 0035941519 scopus 로고    scopus 로고
    • Kinetic solvent effects on hydrogen-atom abstractions: Reliable, quantitative predictions via a single empirical equation
    • Snelgrove, D. W.; Lusztyk, J.; Banks, J. T.; Mulder, P.; Ingold, K. U. Kinetic solvent effects on hydrogen-atom abstractions: Reliable, quantitative predictions via a single empirical equation J. Am. Chem. Soc. 2001, 123, 469-477
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 469-477
    • Snelgrove, D.W.1    Lusztyk, J.2    Banks, J.T.3    Mulder, P.4    Ingold, K.U.5
  • 44
    • 34247143185 scopus 로고    scopus 로고
    • Solvent effects on the rates and mechanisms of reaction of phenols with free radicals
    • 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
    • (2007) Acc. Chem. Res. , vol.40 , pp. 222-230
    • Litwinienko, G.1    Ingold, K.U.2
  • 45
    • 77954335607 scopus 로고    scopus 로고
    • The inactivation of lipid peroxide radical by quercetin. A theoretical insight
    • Chiodo, S. G.; Leopoldini, M.; Russo, N.; Toscano, M. The inactivation of lipid peroxide radical by quercetin. A theoretical insight Phys. Chem. Chem. Phys. 2010, 12, 7662-7670
    • (2010) Phys. Chem. Chem. Phys. , vol.12 , pp. 7662-7670
    • Chiodo, S.G.1    Leopoldini, M.2    Russo, N.3    Toscano, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.