Flavones’ and Flavonols’ Antiradical Structure–Activity Relationship—A Quantum Chemical Study

Ray, 2012, Reactive oxygen species (ROS) homeostasis and redox regulation in cellular signaling, Cell. Signal, 24, 981, 10.1016/j.cellsig.2012.01.008

Hamanaka, 2010, Mitochondrial reactive oxygen species regulate cellular signaling and dictate biological outcomes, Trends Biochem. Sci., 35, 505, 10.1016/j.tibs.2010.04.002

Adams, 2015, Reactive nitrogen species in cellular signaling, Exp. Biol. Med., 240, 711, 10.1177/1535370215581314

Lander, 1997, An essential role for free radicals and derived species in signal transduction, FASEB J., 11, 118, 10.1096/fasebj.11.2.9039953

Breen, 1995, Reactions of oxyl radicals with DNA, Free Radic. Biol. Med., 18, 1033, 10.1016/0891-5849(94)00209-3

Pratt, 2011, Free radical oxidation of polyunsaturated lipids: New mechanistic insights and the development of peroxyl radical clocks, Acc. Chem. Res., 44, 458, 10.1021/ar200024c

Du, 2004, Proteins are major initial cell targets of hydroxyl free radicals, Int. J. Biochem. Cell Biol., 36, 2334, 10.1016/j.biocel.2004.05.012

Hulsmans, 2012, Mitochondrial reactive oxygen species and risk of atherosclerosis, Curr. Atheroscler. Rep., 14, 264, 10.1007/s11883-012-0237-0

Lorente, 2011, Free radicals in breast carcinogenesis, breast cancer progression and cancer stem cells. Biological bases to develop oxidative-based therapies, Crit. Rev. Oncol. Hematol., 80, 347, 10.1016/j.critrevonc.2011.01.004

Sies, 2017, Oxidative Stress, Annu. Rev. Biochem., 86, 715, 10.1146/annurev-biochem-061516-045037

Valko, 2007, Free radicals and antioxidants in normal physiological functions and human disease, Int. J. Biochem. Cell Biol., 39, 44, 10.1016/j.biocel.2006.07.001

Scalbert, 2005, Polyphenols: Antioxidants and beyond, Am. J. Clin. Nutr., 81, 215, 10.1093/ajcn/81.1.215S

Martin, 2015, A review of the efficacy of dietary polyphenols in experimental models of inflammatory bowel diseases, Food Funct., 6, 1773, 10.1039/C5FO00202H

Chen, 2018, Modifications of dietary flavonoids towards improved bioactivity: An update on structure–activity relationship, Crit. Rev. Food Sci. Nutr., 58, 513, 10.1080/10408398.2016.1196334

Masek, 2017, Influence of hydroxyl substitution on flavanone antioxidants properties, Food Chem., 215, 501, 10.1016/j.foodchem.2016.07.183

Musialik, 2009, Acidity of hydroxyl groups: An overlooked influence on antiradical properties of flavonoids, J. Org. Chem., 74, 2699, 10.1021/jo802716v

Heijnen, 2001, Flavonoids as peroxynitrite scavengers: The role of the hydroxyl groups, Toxicol. Vitr., 15, 3, 10.1016/S0887-2333(00)00053-9

Amorati, 2012, Modulation of the antioxidant activity of phenols by non-covalent interactions, Org. Biomol. Chem., 10, 4147, 10.1039/c2ob25174d

Lucarini, 2004, 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. A Eur. J., 10, 933, 10.1002/chem.200305311

Cano, 2002, Superoxide scavenging by polyphenols: Effect of conjugation and dimerization, Redox Rep., 7, 379, 10.1179/135100002125001153

2019, Structural characterization of kaempferol: A spectroscopic and computational study, Maced. J. Chem. Chem. Eng., 38, 49, 10.20450/mjcce.2019.1333

Lucarini, 1996, Bond dissociation energies of O-H bonds in substituted phenols from equilibration studies, J. Org. Chem., 61, 9259, 10.1021/jo961039i

Yokozawa, 1998, Study on the inhibitory effect of tannins and flavonoids against the 1,1-diphenyl-2-picrylhydrazyl radical, Biochem. Pharmacol., 56, 213, 10.1016/S0006-2952(98)00128-2

Lin, 2014, Structure-activity Relationships of Antioxidant Activity in vitro about Flavonoids Isolated from Pyrethrum Tatsienense, J. Intercult. Ethnopharmacol., 3, 123, 10.5455/jice.20140619030232

2014, Towards an improved prediction of the free radical scavenging potency of flavonoids: The significance of double PCET mechanisms, Food Chem., 152, 578, 10.1016/j.foodchem.2013.12.025

Klein, 2018, Theoretical study of the thermodynamics of the mechanisms underlying antiradical activity of cinnamic acid derivatives, Food Chem., 246, 481, 10.1016/j.foodchem.2017.11.100

Pejin, 2017, Antiradical activity of delphinidin, pelargonidin and malvin towards hydroxyl and nitric oxide radicals: The energy requirements calculations as a prediction of the possible antiradical mechanisms, Food Chem., 218, 440, 10.1016/j.foodchem.2016.09.106

Miller, 1996, Structure-antioxidant activity relationships of flavonoids and phenolic acids, Free Radic. Biol. Med., 20, 933, 10.1016/0891-5849(95)02227-9

2003, Structure-radical scavenging activity relationships of flavonoids, Croat. Chem. Acta, 76, 55

Rasulev, 2005, A Quantitative Structure-Activity Relationship (QSAR) study of the antioxidant activity of flavonoids, QSAR Comb. Sci., 24, 1056, 10.1002/qsar.200430013

Tromp, 1996, Structural aspects of antioxidant activity of flavonoids, Free Radic. Biol. Med., 20, 331, 10.1016/0891-5849(95)02047-0

Bors, 1990, Flavonoids as antioxidants: Determination of radical-scavenging efficiencies, Methods Enzymol., 186, 343, 10.1016/0076-6879(90)86128-I

Galano, 2019, Computational strategies for predicting free radical scavengers’ protection against oxidative stress: Where are we and what might follow?, Int. J. Quantum Chem., 119, 1, 10.1002/qua.25665

2016, Study of the mechanisms of antioxidative action of different antioxidants, J. Serbian Soc. Comput. Mech., 10, 135, 10.5937/jsscm1601135M

Sroka, 2015, The antiradical activity of some selected flavones and flavonols. Experimental and quantum mechanical study, J. Mol. Model., 21, 307, 10.1007/s00894-015-2848-1

Hanwell, 2012, Avogadro: An advanced semantic chemical editor, visualization, and analysis platform, J. Cheminform., 4, 17, 10.1186/1758-2946-4-17

Weininger, 1988, SMILES, a chemical language and information system. 1. Introduction to methodology and encoding rules, J. Chem. Inf. Model., 28, 31

Allouche, 2012, Software News and Updates Gabedit—A Graphical User Interface for Computational Chemistry Softwares, J. Comput. Chem., 32, 174, 10.1002/jcc.21600

Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). Gaussian 16, Gaussian, Inc.

Becke, 1993, Density-functional thermochemistry. III. The role of exact exchange, J. Chem. Phys., 98, 5648, 10.1063/1.464913

Tomasi, 2005, Quantum mechanical continuum solvation models, Chem. Rev., 105, 2999, 10.1021/cr9904009

Mennucci, 1997, Continuum solvation models: A new approach to the problem of solute’s charge distribution and cavity boundaries, J. Chem. Phys., 106, 5151, 10.1063/1.473558

Aparicio, 2010, A systematic computational study on flavonoids, Int. J. Mol. Sci., 11, 2017, 10.3390/ijms11052017

Todorova, 2013, Structure of flavones and flavonols. Part I: Role of substituents on the planarity of the system, Comput. Theor. Chem., 1017, 85, 10.1016/j.comptc.2013.05.005

Wang, 1995, Evaluation of ⟨S2⟩ in restricted, unrestricted Hartree-Fock, and density functional based theories, J. Chem. Phys., 102, 3477, 10.1063/1.468585

Tada, 2019, Spin contamination errors on spin-polarized density functional theory/plane-wave calculations for crystals of one-dimensional materials, Appl. Phys. Express, 12, 115506, 10.7567/1882-0786/ab4a37

Urbaniak, 2013, Theoretical investigation of stereochemistry and solvent influence on antioxidant activity of ferulic acid, Comput. Theor. Chem., 1012, 33, 10.1016/j.comptc.2013.02.018

Glendening, E.D., Reed, A.E., Carpenter, J.E., and Weinhold, F. NBO.

Limacher, 2011, Cross-conjugation, Wiley Interdiscip. Rev. Comput. Mol. Sci., 1, 477, 10.1002/wcms.16

Jovanovic, 1996, Which Ring in Flavonoids Is Responsible for Antioxidant Activity?, J. Chem. Soc. Perkins Trans., 2, 2497, 10.1039/p29960002497

Hatzidimitriou, 2007, Changes in the catechin and epicatechin content of grape seeds on storage under different water activity (aw) conditions, Food Chem., 105, 1504, 10.1016/j.foodchem.2007.05.032

Apak, 2010, Solvent effects on the antioxidant capacity of lipophilic and hydrophilic antioxidants measured by CUPRAC, ABTS/persulphate and FRAP methods, Talanta, 81, 1300, 10.1016/j.talanta.2010.02.025

Benzie, 1996, The Ferric Reducing Ability of Plasma (FRAP) as a Measure of “Antioxidant Power”: The FRAP Assay, Anal. Biochem., 239, 70, 10.1006/abio.1996.0292

Re, 1999, Antioxidant activity applying an improved ABTS radical cation decolorization assay, Free Radic. Biol. Med., 26, 1231, 10.1016/S0891-5849(98)00315-3

Cuvelier, 1995, Use of a free radical method to evaluate antioxidant activity, LWT Food Sci. Technol., 28, 25, 10.1016/S0023-6438(95)80008-5

Cheng, 2015, Antioxidant-capacity-based models for the prediction of acrylamide reduction by flavonoids, Food Chem., 168, 90, 10.1016/j.foodchem.2014.07.008

2018, Hydrogen atom transfer versus proton coupled electron transfer mechanism of gallic acid with different peroxy radicals, React. Kinet. Mech. Catal., 123, 215, 10.1007/s11144-017-1286-8

Milenković, D., Dorović, J., Jeremić, S., Dimitrić Marković, J.M., Avdović, E.H., and Marković, Z. (2017). Free Radical Scavenging Potency of Dihydroxybenzoic Acids. J. Chem., 2017.

2017, Importance of hydrogen bonding and aromaticity indices in QSAR modeling of the antioxidative capacity of selected (poly)phenolic antioxidants, J. Mol. Graph. Model., 72, 240, 10.1016/j.jmgm.2017.01.011

2015, QSAR of the free radical scavenging potency of selected hydroxybenzoic acids and simple phenolics, Comptes Rendus Chim., 18, 492, 10.1016/j.crci.2014.09.001

Chen, 2015, Structure-thermodynamics-antioxidant activity relationships of selected natural phenolic acids and derivatives: An experimental and theoretical evaluation, PLoS ONE, 10, 1

Arora, 1998, Structure-activity relationships for antioxidant activities of a series of flavonoids in a liposomal system, Free Radic. Biol. Med., 24, 1355, 10.1016/S0891-5849(97)00458-9

Galano, 2013, Deprotonation mechanism and acidity constants in aqueous solution of flavonols: A combined experimental and theoretical study, J. Phys. Chem. B, 117, 12347, 10.1021/jp4049617

2014, The preferred radical scavenging mechanisms of fisetin and baicalein towards oxygen-centred radicals in polar protic and polar aprotic solvents, RSC Adv., 4, 32228, 10.1039/C4RA02577F

Huang, 2005, The chemistry behind antioxidant capacity assays, J. Agric. Food Chem., 53, 1841, 10.1021/jf030723c

2014, Energy requirements of the reactions of kaempferol and selected radical species in different media: Towards the prediction of the possible radical scavenging mechanisms, Struct. Chem., 25, 1795, 10.1007/s11224-014-0453-z

Peng, 1993, Combining Synchronous Transit and Quasi-Newton Methods to Find Transition States, Isr. J. Chem., 33, 449, 10.1002/ijch.199300051

Maini, 2012, The UVA and aqueous stability of flavonoids is dependent on B-ring substitution, J. Agric. Food Chem., 60, 6966, 10.1021/jf3016128

Pearson, 2005, Chemical hardness and density functional theory, J. Chem. Sci., 117, 369, 10.1007/BF02708340

Parr, 1983, Absolute Hardness: Companion Parameter to Absolute Electronegativity, J. Am. Chem. Soc., 105, 7512, 10.1021/ja00364a005

Waki, 2012, Key role of chemical hardness to compare 2,2-diphenyl-1-picrylhydrazyl radical scavenging power of flavone and flavonol O-glycoside and C-glycoside derivatives, Chem. Pharm. Bull., 60, 37, 10.1248/cpb.60.37

Mazzone, 2016, Antioxidant properties comparative study of natural hydroxycinnamic acids and structurally modified derivatives: Computational insights, Comput. Theor. Chem., 1077, 39, 10.1016/j.comptc.2015.10.011