Theoretical investigation on the antioxidative activity of anthocyanidins: A DFT/B3LYP study

Dyes and Pigments

Volumn 103, Issue , 2014, Pages 175-182

  Lu, Lilin ^a   Qiang, Min ^a   Li, Faliang ^a   Zhang, Haijun ^a   Zhang, Shaowei ^a  

^a WUHAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Anthocyanidins; Antioxidative activity; Density functional theory; Mechanism; Structure activity relationship; Substituent effect

Indexed keywords

ANTHOCYANIDINS; ANTI OXIDATIVE ACTIVITY; ANTIOXIDATIVE PROPERTY; ELECTRON TRANSFER; SINGLE ELECTRON TRANSFER; STRUCTURE ACTIVITY RELATIONSHIPS; SUBSTITUENT EFFECT; THEORETICAL INVESTIGATIONS;

CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; GASES; IONIZATION POTENTIAL; MECHANISMS; NEGATIVE IONS; PROTONS;

ELECTRON TRANSITIONS;

EID: 84891697674     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.12.015     Document Type: Article

References (47)

1. G. Duthie, S. Duthie, and J. Kyle Plant polyphenols in cancer and heart disease: implications as nutritional antioxidants Nutr Res Rev 13 2000 79 106 (Pubitemid 30495755)
2. S. Quideau, D. Deffieux, C. Douat-Casassus, and L. Pouysegu Plant polyphenols: chemical properties, biological activities, and synthesis Angew Chem Int Ed 50 2011 586 621
3. Y. Zhang, S.K. Vareed, and M.G. Nair Human tumor cell growth inhibition by nontoxic anthocyanidins, the pigments in fruits and vegetables Life Sci 76 2005 1465 1472 (Pubitemid 40164775)
4. M.N. Clifford Anthocyanins-nature, occurrence and dietary burden J Sci Food Agric 80 2000 1063 1072
5. N. Malaj, B.C.D. Simone, A.D. Quartarolo, and N. Russo Spectrophotometric study of the copigmentation of malvidin 3-O-glucoside with p-coumaric, vanillic and syringic acids Food Chem 141 2013 3614 3620
6. Y. Noda, T. Kaneyuki, A. Mori, and L. Packer Antioxidant activities of pomegranate fruit extract and its anthocyanidins: delphinidin, cyanidin, and pelargonidin J Agric Food Chem 50 2002 166 171 (Pubitemid 34038526)
7. J. Lachman, K. Hamouz, M. Sulc, M. Orsak, V. Pivec, and A. Hejtmankova et al. Cultivar differences of total anthocyanins and anthocyanidins in red and purple-fleshed potatoes and their relation to antioxidant activity Food Chem 114 2009 836 843
8. H. Li, Z. Deng, H. Zhu, C. Hu, R. Liu, and J.C. Young et al. Highly pigmented vegetables: anthcyanin compositions and their role in antioxidant activities Food Res Int 46 2012 250 259
9. J. Azevedo, I. Fernandes, A. Faria, J. Oliveira, A. Fernandes, and V. Freitas et al. Antioxidant properties of anthocyanidins, anthocyanidin-3- glucosides and respective portisins Food Chem 119 2010 518 523
10. D. Bagchi, A. Garg, R.L. Krohn, M. Bagchi, D.J. Bagchi, and J. Balmoori et al. Protective effects of grape seed proanthocyanidins and selected antioxidants against TPA-induced hepatic and brain lipid peroxidation and DNA fragmentation, and peritoneal macrophage activation in mice Gen Pharmacol Vasc Syst 30 1998 771 776
11. Z.Y. Chen, P.T. Chan, K.Y. Ho, K.P. Fung, and J. Wang Antioxidant activity of natural flavonoids is governed by number and location of their aromatic hydroxyl groups Chem Phys Lipids 79 1996 157 163 (Pubitemid 26143737)
12. H. Kamei, T. Kojima, M. Hasegawa, T. Koide, T. Umeda, and T. Yukawa et al. Suppression of tumor cell growth by anthocyanins in vitro Cancer Invest 13 1995 590 594
13. B. Halliwell, R. Aeschbach, J. Loliger, and O.I. Arouma The characterization of anitoxidants Food Chem Toxicol 33 1995 601 617
14. E. Middleton Jr., C. Kandaswami, and T.C. Theoharides The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer Pharmacol Rev 52 2000 673 751
15. C.S. Yang, J.M. Landau, M.T. Huang, and H.L. Newmark Inhibition of carcinogenesis by dietary polyphenolic compounds Annu Rev Nutr 21 2001 381 406 (Pubitemid 32695277)
16. Y. Sakihama, M.F. Cohen, S.C. Grace, and H. Yamasaki Plant phenolic antioxidant and prooxidant activities: phenolics-induced oxidative damage mediated by metals in plants Toxicology 177 2002 67 80 (Pubitemid 34786245)
17. W. Ren, Z. Qiao, H. Wang, L. Zhu, and L. Zhang Flavonoids: promising anticancer agents Med Res Rev 23 2003 519 534 (Pubitemid 36706514)
18. L.R. Ferguson Role of plant polyphenols in genomic stability Mutat Res 475 2001 89 111 (Pubitemid 32280805)
19. W.E. Kurtin, and P.S. Song Electronic structures and spectra of some natural products of theoretical interest-I: molecular orbital studies of anthocyanidins Tetrahedron 24 1968 2255 2267
20. K. Sakata, N. Saito, and T. Honda Ab initio study of molecular structures and excited states in anthocyanidins Tetrahedron 62 2006 3721 3731
21. J.N. Woodford A DFT investigation of anthocyanidins Chem Phys Lett 410 2005 182 187 (Pubitemid 40929397)
22. E.H. Anouar, J. Gierschner, J.L. Duroux, and P. Trouillas UV/Visible spectra of natural polyphenols: a time-dependent density functional theory study Food Chem 131 2012 79 89
23. L. Estévez, and R.A. Mosquera A density functional theory study on pelargonidin J Phys Chem A 111 2007 11100 11109 (Pubitemid 350097568)
24. L. Estévez, and R.A. Mosquera Conformational and substitution effects on the electron distribution in a series of anthocyanidins J Phys Chem A 113 2009 9908 9919
25. M. Leopoldini, N. Russo, and M. Toscano The molecular basis of working mechanism of natural polyphenolic antioxidants Food Chem 125 2011 288 306
26. G. Mazzone, N. Malaj, N. Russo, and M. Toscano Density functional study of the antioxidant activity of some recently synthesized resveratrol analogues Food Chem 141 2013 2017 2024
27. M.E. Alberto, N. Russo, A. Grand, and A. Galano A physicochemical examination of the free radical scavenging activity of trolox: mechanism, kinetics and influence of the environment Phys Chem Chem Phys 15 2013 4642 4650
28. A.D. Quartarolo, and N. Russo A computational study (TDDFT and RICC2) of the electronic spectra of pyranoanthocyanins in the gas phase and solution J Chem Theor Comput 7 2011 1073 1081
29. M. Leopoldini, F. Rondinelli, N. Russo, and M. Toscano Pyranoanthocyanins: a theoretical investigation on their antioxidant activity J Agric Food Chem 58 2010 8862 8871
30. C. Iuga, J.R. Alvarez-Idaboy, and N. Russo Antioxidant activity of trans-resveratrol toward hydroxyl and hydroperoxyl radicals: a quantum chemical and computational kinetics study J Org Chem 77 2012 3868 3877
31. R. Guzmán, C. Santiago, and M. Sánchez A density functional study of antioxidant properties on anthocyanidins J Mol Struct 935 2009 110 114
32. L. Estévez, and R.A. Mosquera Molecular structure and antioxidant properties of delphinidin J Phys Chem A 112 2008 10614 10623
33. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman et al. Gaussian 03, revision B.05 2003 Gaussian, Inc. Pittsburgh PA
34. A.D. Becke Density-functional thermochemistry. â...¢. The role of exact exchange J Chem Phys 98 1993 5648 5652
35. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys Rev B 37 1988 785 789
36. J.S. Wright, E.R. Johnson, and G.A. DiLabio Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effect, and application to major families of antioxidants J Am Chem Soc 123 2001 1173 1183 (Pubitemid 32148182)
37. A. Martínez, R. Vargas, and A. Galano What is important to prevent oxidative stress? A theoretical study on electron-transfer reactions between carotenoids and free radicals J Phys Chem B 113 2009 12113 12120
38. A. Martínez Donator acceptor map of psittacofulvins and anthocyanins: are they good antioxidant substances? J Phys Chem B 113 2009 4915 4921
39. A. Martínez, E. Hernández-Marin, and A. Galano Xanthones as antioxidants: a theoretical study on the thermodynamics and kinetics of the single electron transfer mechanism Food Funct 3 2012 442 450
40. L. Lu, S. Zhu, H. Zhang, and S. Zhang Improvement of antioxidative activity of resveratrol by elongating conjugated chain: a DFT theoretical study Comp Theor Chem 1019 2013 39 47
41. G. Rastelli, L. Costantino, and A. Albasini Physico-chemical properties of anthocyanidins. Part 1. Theoretical evaluation of the stability of the neutral and anionic tautomeric forms J Mol Struct (Theochem) 279 1993 157 166
42. G.K. Pereira, P.M. Donate, and S.E. Galembeck Electronic structure of hydroxylated derivatives of the flavylium cation J Mol Struct 363 1996 87 96 (Pubitemid 126392749)
43. M. Meyer Ab initio study of flavonoids Int J Quant Chem 76 2000 724 732
44. H. Wang, G. Cao, and R.L. Prior Oxygen radical absorbing capacity of anthocyanins J Agric Food Chem 45 1997 304 309 (Pubitemid 127485925)
45. G. Litwinienko, and K.U. Ingold Solvent effects on the rates and mechanisms of reaction of phenols with free radicals Acc Chem Res 40 2007 222 230
46. T. Borkowski, H. Szymusiak, A. Gliszczynska-Swiglo, I.M.C.M. Rietjens, and B. Tyrakowska Radical scavenging capacity of wine anthocyanins is strongly pH-dependent J Agric Food Chem 53 2005 5526 5534 (Pubitemid 41022441)
47. A.N. Queiroz, B.A.Q. Gomes, W.M. Moraes Jr., and R.S. Borges A theoretical antioxidant pharmacophore for resveratrol Eur J Med Chem 44 2009 1644 1649