Density functional study of the antioxidant activity of some recently synthesized resveratrol analogues

Food Chemistry

Volumn 141, Issue 3, 2013, Pages 2017-2024

  Mazzone, Gloria ^a   Malaj, Naim ^a   Russo, Nino ^a   Toscano, Marirosa ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

Antioxidant mechanism; Bond dissociation energy (BDE) and ionization potential (IP); Cis Resveratrol analogues; UV Vis characterization

Indexed keywords

AGENTS; ANTIOXIDANTS; BOND STRENGTH (CHEMICAL); CARBON; DISSOCIATION; FREE RADICAL REACTIONS; FREE RADICALS; IONIZATION; RESVERATROL;

ANTI-OXIDANT ACTIVITIES; ANTIOXIDANT MECHANISMS; BOND DISSOCIATION ENERGIES; CIS-RESVERATROL ANALOGUES; DEGREE OF CONJUGATIONS; DENSITY-FUNCTIONAL STUDY; SINGLE ELECTRON TRANSFER; STABILIZING EFFECTS;

IONIZATION POTENTIAL;

ANTIOXIDANT; CATECHOL; METHANOL; RESVERATROL;

ANTIOXIDANT ACTIVITY; ARTICLE; CONJUGATION; ELECTRON TRANSPORT; IONIZATION;

EID: 84879043123     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2013.05.071     Document Type: Article

References (34)

1. Amorati, R., Lucarini, M., Mugnaini, V., Pedulli, G. F., Roberti, M., & Pizzirani, D. (2004). Antioxidant activity of hydroxystilbene derivatives in homogeneous solution. The Journal (Pubitemid 39363006)
2. Becke, A. D. J. (1993). Density-functional thermochemistry 3. The role of exact exchange. Chemical Physics, 98(7), 5648-5652.
3. Burns, J., Yokota, T., Ashihara, H., Lean, M. E. J., & Crozier, A. (2002). Plant foods and herbal sources of resveratrol. Journal of Agricultural and Food Chemistry, 50, 3337-3340. (Pubitemid 34533643)
4. Callahan, M. P., Gengeliczki, Z., & de Vries, M. S. (2008). Resonant two-photon ionization mass spectrometry of jet-cooled phenolic acids and polyphenols. Analytical Chemistry, 80, 2199-2203. (Pubitemid 351458071)
5. Cao, H., Pan, X., Li, C., Zhou, C., Deng, F., & Li, T. (2003). Density functional theory calculations for resveratrol. Bioorganic Medicinal Chemistry Letters, 13, 1869-1871. (Pubitemid 36577131)
6. Caruso, F., Tanski, J., Villegas-Estrada, A., & Rossi, M. (2004). Structural basis for antioxidant activity of trans-resveratrol: Ab initio calculations and crystal and molecular structure. Journal of Agricultural and Food Chemistry, 52, 7279-7285.
7. Casida, M. E. (1995). Time-dependent density functional response theory for molecules. In D. P. Chong (Ed.). Recent advances in density functional methods (1st ed.) (Vol. 1, pp. 155-192). Singapore, Singapore: Word Scientific.
8. Cossi, M., Rega, N., Scalmani, G., & Barone, V. (2003). Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. Journal of Computational Chemistry, 24, 669-681.
9. Ding, D. J., Cao, X. Y., Dai, F., Li, X. Z., Liu, G. Y., Lin, D., et al. (2012). Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues. Food Chemistry, 135, 1011-1019.
10. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, Jr., J. A., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., 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., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., Pople, J. A. (2004). Wallingford, CT: Gaussian 03, revision C.02; Gaussian, Inc.
11. Galano, A. (2011). On the direct scavenging activity of melatonin towards hydroxyl and a series of peroxyl radicals. Physical Chemistry Chemical Physics: PCCP, 13, 7147-7157.
12. Iuga, C., Alvarez-Idaboy, J. R., & Russo, N. (2012). Antioxidant activity of transresveratrol toward hydroxyl and hydroperoxyl radicals: A quantum chemical and computational kinetics study. Journal of Organic Chemistry, 77, 3868-3877.
13. Jacquemin, D., Perpete, E. A., Ciofini, I., & Adamo, C. (2009). Accurate simulation of optical properties in dyes. Accounts of Chemical Research, 42, 326.
14. Jovanović, S. V., Steenken, S., Simić, M. G., & Hara, Y. (1998). Antioxidant properties of flavonoids: Reduction potentials and electron transfer reactions of flavonoids radicals. In C. Rice-Evans & L. Packer (Eds.), Flavonoids in health and disease (pp. 137-161). New York: Marcel Dekker.
15. Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation - Energy formula into a functional of the electron density. Physical Review B, 37(2), 785-789.
16. Leopoldini, M., Chiodo, S. G., Russo, N., & Toscano, M. (2011). Detailed investigation of the OH radical quenching by natural antioxidant caffeic acid studied by quantum mechanical models. Journal of Chemical Theory and Computation, 7, 4218-4233.
17. Leopoldini, M., Marino, T., Russo, N., & Toscano, M. (2004a). Antioxidant properties of phenolic compounds: H-atom versus electron transfer mechanism. The Journal of the Physical Chemistry A, 108(22), 4916-4922.
18. Leopoldini, M., Marino, T., Russo, N., & Toscano, M. (2004b). Density functional computations of the energetic and spectroscopic parameters of quercetin and its radicals in the gas phase and in solvent. Theoretical Chemistry Accounts, 111(2-6), 210-216. (Pubitemid 38650546)
19. Leopoldini, M., Russo, N., & Toscano, M. (2006). Gas and liquid phase acidity of natural antioxidants. Journal of Agriculture and Food Chemistry, 54(8), 3078-3085.
20. Leopoldini, M., Russo, N., & Toscano, M. (2011). The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chemistry, 125, 288-306.
21. Marsh, N. D., Mikolajczak, C. J., & Wornat, M. J. (2000). The effect of ethynyl substitution and cyclopenta fusion on the ultraviolet visible absorption spectra of polycyclic aromatic hydrocarbons. Spectrochimica Acta Part A, 56, 1499-1511.
22. Mikulski, D., Górniak, R., & Molski, M. (2010). A theoretical study of the structure radical scavenging activity of trans-resveratrol analogues and cis-resveratrol in gas phase and water environment. European Journal of Medicinal Chemistry, 45, 1015-1027.
23. Pérez-González, A., & Galano, A. (2012). On the outstanding antioxidant capacity of edaravone derivatives through single electron transfer reactions. The Journal of Physical Chemistry B, 116, 1180-1188.
24. Queiroz, A. N., Gomes, B. A. Q., Moraes, W. M., Jr., & Borges, R. S. (2009). A theoretical antioxidant pharmacophore for resveratrol. European Journal of Medicinal Chemistry, 44, 1644-1649.
25. Siemann, E. H., & Creasy, L. L. (1992). Concentration of the phytoalexin resveratrol in wine. American Journal of Enology and Viticulture, 43, 49-52.
26. Silva, C. G., Monteiro, J., Marques, R. R., Silva, A. M., Martínez, C., Canle, L. M., et al. (2013). Photochemical and photocatalytic degradation of trans-resveratrol. Photochemical & Photobiological Sciences. http://dx.doi.org/10.1039/C2PP25239B.
27. Smoliga, J. M., Baur, J. A., & Hausenblas, H. A. (2011). Resveratrol and health - A comprehensive review of human clinical trials. Molecular Nutrition and Food Research, 55, 1129-1141.
28. Stojanović, S., & Brede, O. (2002). Elementary reactions of the antioxidant action of trans-stilbene derivatives: Resveratrol, pinosylvin and 4-hydroxystilbene. Physical Chemistry Chemical Physics, 4, 757-764.
29. Stratmann, R. E., Scuseria, G. E., & Frisch, M. J. (1998). An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules. The Journal of Chemical Physics, 109, 8218-8224. (Pubitemid 128672179)
30. Trela, B. C., & Waterhouse, A. L. (1996). Resveratrol: Isomeric molar absorptivities and stability. Journal of Agriculture and Food Chemistry, 44, 1253-1257. (Pubitemid 126467853)
31. van Acker, S. A., de Groot, M. J., van den Berg, D. J., Tromp, M. N., den Donnè-Op Kelder, G., van der Vijgh, W. J., et al. (1996). A quantum chemical explanation of the antioxidant activity of flavonoids. Chemical Research in Toxicology, 9(8), 1305-1312. (Pubitemid 26403836)
32. van Acker, S. A., van den Berg, D. J., Tromp, M. N., Griffioen, D. H., van Bennekom, W. P., van der Vijgh, W. J., et al. (1996). Structural aspects of antioxidant activity of flavonoids. Free Radical Biology and Medicine, 20(3), 331-342. (Pubitemid 26077855)
33. Wang, M., Jin, Y., & Ho, C. T. (1999). Evaluation of resveratrol derivatives as potential antioxidants and identification of a reaction product of resveratrol and 2,2- diphenyl-1-picryhydrazyl radical. Journal of Agricultural and Food Chemistry, 47, 3974-3977. (Pubitemid 29506186)
34. Wright, J. S., Johnson, E. R., & DiLabio, G. A. (2001). Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants. Journal of the American Chemical Society, 123(6), 1173-1183. (Pubitemid 32148182)