Abstract
A relationship between the antiradical activity of flavonoids and the molecular descriptors related to the mechanism of their antiradical action was determined by single-variable linear regression analysis in the form of a semiempirical single-variable linear equation. The predictive ability of the derived model was evaluated using a test sample; the average error of approximation was no more than 8.5%. The obtained descriptor–activity relationship underlies the prediction of the antiradical properties of flavonoids and their similar structures in aqueous solutions with a physiological pH value of the medium.
Similar content being viewed by others
REFERENCES
Vermerris, W. and Nicolson, R., Phenolic Compound Biochemistry, Dodrecht: Springer, 2006, p. 276.
Kostyuk, V.A. and Potapovich, A.I., Bioradikaly i bioantioksidanty (Bioradicals and Bioantioxidants), Minsk: Belarus State University, 2004, p. 179.
Alov, P., Tsakovska, I., and Pajeva, I., Curr. Top. Med. Chem., 2015, vol. 15, p. 85.
Lagunin, A., Zakharov, A., Filimonov, D., and Poroikov, V., Mol. Inf., 2011, vol. 30, nos. 2–3, p. 241.
Javan, A.J., Food Chem. 2014, vol. 165, p. 451.
Vaganek, A., Rimarčik, J., Dropkova, K., Lengyel, J., and Klein, E., Comput. Theor. Chem., 2014, vol. 1050, p. 31.
Rabinovich, V.A. and Khavin, Z.Ya., Kratkii khimicheskii spravochnik (Short Chemical Dictionary), Leningrad: Khimiya, 1991, p. 432.
Armarego, W.L.F. and Chai, C.L.L., Purification of Laboratory Chemicals, Burlington: Elsevier, 2003, p. 608.
Shlyapintokh, V.Ya., Karpukhin, O.N., Postnikov, L.M., Zakharov, I.P., Vichutinskii, A.A., and Tsepalov, V.F., Khemilyuminestsentnye metody issledovaniya medlennykh khimicheskikh protsessov (Chemiluminescence Methods of Study of Slow Chemical Processes), Moscow: Nauka, 1966, p. 300.
Stefek, M., Kyselova, Z., Rackova, L., and Krizanova, L., Biochim. Biophys. Acta, 2005, vol. 1741, p. 183.
Rackova, L., Stefek, M., and Majekova, M., Redox Rep., 2002, vol. 7, p. 207.
Belyakov, V.A., Vasil’ev, R.F., and Fedorova, G.F., Kinet. Catal., 2004, vol. 45, no. 3, p. 329.
Yuzhakov, V.I. and Pashchenko, V.Z., Kvantovaya Elektron., 1980, vol. 7, no. 3, p. 613.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., and Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J. Gaussian 09, Revision B.01 Gaussian, Wallingford, 2010.
Weinberg, D.R., Gagliardi, C.J., Hull, J.F., Murphy, C.F., Kent, C.A., Westlake, B., Paul, A., Ess, D.H., McCafferty, G.D., and Meyer, T.J., Chem. Rev., 2007, vol. 107, no. 11, p. 5004.
Belaya, N.I, Belyi, A.V., Zarechnaya, O.M., Shcherbakov, I.N., Mikhal’chuk, V.M., and Doroshkevich, V.S., Russ. J. Gen. Chem., 2017, vol. 87, no. 4, p. 690.
Tomasi, J., Mennucci, B., and Cammi, R., Chem. Rev., 2005, vol. 105, no. 8, p. 2999.
Rappe, A.K., Casewit, C.J., Colwell, K.S., Goddard, W.A., and Skiff, W.M., J. Am. Chem. Soc., 1992, vol. 114, no. 25, p. 10024.
Marvin 18.14.0. ChemAxon. https://www.chemaxon.com.
Elyashberg, M., Williams, A., and Blinov, K., Contemporary Computer-Assisted Approaches to Molecular Structure Elucidation, Cambridge: RSC, 2012, p. 469.
Alekseev, A.V., Proskurnina, E.V., and Vladimirov, Yu.A., Moscow Univ. Chem. Bull., 2012, vol. 67, no. 3, p. 127.
Veprintsev, T.L., Naumov, V.V., and Trofimov, A.V., Butlerov. Soobshch., 2011, vol. 25, no. 5, p. 96.
Vasil’ev, R.F., Veprintsev, T.L., Dolmatova, L.S., Naumov, V.V., Trofimov, A.V., and Tsaplev, Yu.B., Kinet. Catal., 2014, vol. 55, no. 2, p. 148.
Roginskii, V.A., Fenol’nye antioksidanty. Reaktsionnaya sposobnost' i effektivnost' (Phenolic Antioxidants. Reactivity and Efficiency), Moscow: Nauka, 1988, p. 247.
Galano, A., Mazzone, G., Alvarez-Diduk, R., Marino, T., Alvarez-Idaboy, J.R., and Russo, N., Annu. Rev. Food Sci. Technol., 2016, vol. 7, p. 335.
Mazzone, G., Russo, N., and Toscano, M., Comput. Theor. Chem., 2016, vol. 1077, p. 39.
Litwinienko, G. and Ingold, K.U., Acc. Chem. Res., 2007, vol. 40, no. 3, p. 222.
Volkov, V.A. and Misin, V.M., Kinet. Catal., 2015, vol. 56, no. 1, p. 43.
Mazzone, G., Russo, N., and Toscano, M., Comput. Theor. Chem., 2016, vol. 1077, p. 39.
Belaya, N.I., Belyi, A.V., Zarechnaya, O.M., Shcherbakov, I.N., and Doroshkevich, V.S., Russ. J. Gen. Chem., 2018, vol. 88, no. 7, p. 1351.
Marković, Z., Đorović, J., and Petrović, Z.D., J. Mol. Model., 2015, vol. 21, p. 293.
Pérez-González, A., Galano, A., and Alvarez-Idaboy, J.R., New J. Chem., 2014, vol. 38, p. 2639.
Chernikov, D.A., Pal’shin, V.A., Bazhenov, B.N., and Safronov, A.V., Izv. Vyssh. Uchebn. Zaved.,Khim. Khim. Tekhnol., 2012, vol. 55, no. 8, p. 43.
Derffel’, K., Statistika v analiticheskoi khimii (Statistics in Analytical Chemistry), Moscow: Mir, 1994, p. 268.
ACKNOWLEDGMENTS
The DFT calculations were performed at the High-Performance Computations Center for Shared Use of Scientific Equipment, Southern Federal University, Rostov-on-Don, Russia.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interest.
Additional information
Translated by V. Glyanchenko
Abbreviation: ARA, antiradical activity, APOO•, 2-amidinopropane-2-peroxyl radical; AAPH, 2,2'-azo-bis-(2-amidinopropane) dihydrochloride; DFT, density functional theory; ET–PT, electron transfer–proton transfer; FlavOH, flavonoids; Rd6G, Rhodamine 6G; CL, chemiluminescence; QSAR/QSPR, quantitative structure–activity/property relationships; SPLET, sequential proton loss electron transfer.
Rights and permissions
About this article
Cite this article
Belaya, N.I., Belyi, A.V. & Shcherbakov, I.N. Predictive Model of the Relationship of the Antiradical Activity and the Ionization Potential of Molecules and Ions of Flavonoids. Kinet Catal 61, 360–368 (2020). https://doi.org/10.1134/S0023158420030040
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0023158420030040