A DFT Study on the Structural and Antioxidant Properties of Three Flavonols

Food Biophysics

Volumn 8, Issue 2, 2013, Pages 90-94

  Rong, Yu Zhi ^a   Wang, Zheng Wu ^a   Zhao, Bo ^b  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

^b NANJING NORMAL UNIVERSITY   (China)

Author keywords

Antioxidant; Bond dissociation enthalpy; Density functional; Flavonols; Free radicals; Ionization potential

Indexed keywords

ANTIOXIDANTS; ATOMS; CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ELECTRON TRANSITIONS; ENTHALPY; FLAVONOIDS; FREE RADICAL REACTIONS; FREE RADICALS; HYDROGEN; IONIZATION OF LIQUIDS; PLANTS (BOTANY);

ANTI-OXIDANT ACTIVITIES; ANTIOXIDANT PROPERTIES; BOND DISSOCIATION ENTHALPIES; DENSITY FUNCTIONALS; DENSITY-FUNCTIONAL LEVEL; FLAVONOLS; HYDROGEN-ATOM TRANSFER; SINGLE ELECTRON TRANSFER;

IONIZATION POTENTIAL;

EID: 84962467960     PISSN: 15571858     EISSN: 15571866     Source Type: Journal    
DOI: 10.1007/s11483-012-9276-x     Document Type: Article

References (28)

1. K. L. Wolfe, R. H. Liu, Structure-activity relationships of flavonoids in the cellular antioxidant activity assay. J. Agric. Food Chem. 56, 8404-8411 (2008).
2. R. H. Liu, Potential synergy of phytochemicals in cancer prevention: mechanism of action. J. Nutr. 134, 3479S-3485S (2004).
3. K. L. Wolfe, R. H. Liu, Cellular antioxidant activity (CAA) assay for assessing antioxidants, foods, and dietary supplements. J. Agric. Food Chem. 55, 8896-8907 (2007).
4. K. L. Wolfe, X. Kang, X. He, M. Dong, Q. Y. Zhang, R. H. Liu, Cellular antioxidant activity of common fruits. J. Agric. Food Chem. 56, 8418-8426 (2008).
5. F. Ko, C. Chu, C. Lin, C. Chang, C. Teng, Isoorientin-6-Oglucoside, a water-soluble antioxidant isolated from Gentiana arisanensis. Biochem. Biophys. Acta 1389, 81-90 (1998).
6. M. Novic, Z. Nikolovska, T. Solmajer, Quantitative structureactivity relationship of flavonoid p56lck protein tyrosine kinase inhibitors. A neural network approach. J. Chem. Inf. Comput. Sci. 37, 990-998 (1997).
7. D. Amic, D. Davidovic, A. Juric, B. Lucic, N. Trinajstic, Structure-activity correlation of flavone derivatives for inhibition of cAMP phosphodiesterase. J. Chem. Inf. Comput. Sci. 35, 1034-1038 (1995).
8. Y. Uda, K. Price, G. Williamson, M. Rhodes, Induction of the anticarcinogenic marker enzyme, quinone reductase, in murine hepatoma cells in vitro by flavonoids. Cancer Lett. 120, 213-216 (1997).
9. S. Tahara, Y. Katagiri, J. Ingham, J. Mizutani, Prenylated flavonoids in the root of yellow lupin. Phytochemistry 36, 1261-1271 (1994).
10. M. Amoros, C. M. O. Simoes, L. Girre, F. Sauvager, M. Cormier, Synergistic effect of flavones and flavonols against herpes simplex virus type 1 in cell culture. Comparison with the antiviral activity of propolis. J. Nat. Prod. 55, 1732-1740 (1992).
11. A. J. Miller, Antioxidant flavonoids: structure, function, and clinical usage. Altern. Med. ReV. 1, 103-111 (1996).
12. S. D. Skaper, M. Fabris, V. Q. Ferrari, Quercetin protects cutaneous tissue-associated cell types including sensory neurons from oxidative stress induced by glutathione depletion: cooperative effects of ascorbic acid. Free Radic. Biol. Med. 22, 669-678 (1997).
13. R. D. Loggia, E. Ragazzi, A. Tubaro, Anti-inflammatory activity of benzoppyrones that are inhibitors of cyclo- and lipooxygenase. Pharmacol. Res. Commun. 20, S91-S94 (1988).
14. H. P. Kim, I. Mani, V. A. Ziboh, Effects of naturally-occurring flavonoids and biflavonoids on epiderman cyclooxygenase from guinea pigs. Prostaglandins Leukot. Essent. Fat. Acids 58, 17-24 (1998).
15. J. S. Wright, E. R. Johnson, G. A. D. Labio, Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects and application to major families of antioxidants. J. Am. Chem. Soc. 123, 1173-1183 (2001).
16. M. Leopoldini, I. Prieto Pitarch, N. Russo, M. Toscano, Structure, conformation and electronic properties of apigenin, luteolin and taxifolin antioxidants. A first principle theoretical study. J. Phys. Chem. B 108, 92-96 (2004).
17. M. Leopoldini, T. Marino, N. Russo, M. Toscano, Antioxidant properties of phenolic compounds. H-atom versus electron transfer mechanism. J. Phys. Chem. B 108, 4916-4922 (2004).
18. M. Leopoldini, T. Marino, N. Russo, M. Toscano, Density functional computations of the energetic and spectroscopic parameters of quercetin and its radicals in the gas phase and in solvent. Theor. Chem. Acc. 111, 210-216 (2004).
19. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B. 05 (Gaussian, Inc, Pittsburgh, 2003).
20. A. D. Becke, Density-functional thermochemistry III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652 (1993).
21. C. Lee, W. Yang, R. G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. ReV. B 37, 785-789 (1988).
22. R. Ditchfield, W. J. Hehre, J. A. Pople, Self-consistent molecularorbital methods: IX. An extended Gaussian-type basis for molecular-orbital studies of organic molecules. J. Chem. Phys. 54, 724-728 (1971).
23. W. J. Hehre, R. Ditchfield, J. A. Pople, Self-consistent molecular orbital methods: XII. Further extensions of Gaussian-type basis sets for use in molecular orbital studies of organic molecules. J. Chem. Phys. 56, 2257-2261 (1972).
24. S. Miertus, E. Scrocco, J. Tomasi, Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Chem. Phys. 55, 117-129 (1981).
25. S. Miertus, J. Tomasi, Approximate evaluations of the electrostatic free energy and internal energy changes in solution processes. Chem. Phys. 65, 239-245 (1982).
26. M. Cossi, V. Barone, R. Cammi, J. Tomasi, Ab initio study of solvated molecules: a new implementation of the polarizable continuum model. Chem. Phys. Lett. 255, 327-335 (1996).
27. V. Barone, M. Cossi, J. Tomasi, A new definition of cavities for the computation of solvation free energies by the polarizable continuum model. J. Chem. Phys. 107, 3210-3221 (1997).
28. 3OO*. An upper limit for the heat of formation of the methylperoxy radical. J. Phys. Chem. 88, 6675-6680 (1984).