Iron complexes of dietary flavonoids: Combined spectroscopic and mechanistic study of their free radical scavenging activity

Food Chemistry

Volumn 129, Issue 4, 2011, Pages 1567-1577

  Dimitrić Marković, Jasmina M ^a   Marković, Zoran S ^b   Brdarić, Tanja P ^c   Pavelkić, Vesna M ^c   Jadranin, Milka B ^d  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b State University of Novi Pazar   (Serbia)

^c Institute Kirilo Savic   (Serbia)

^d UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

B3LYP 6 31G (d, p) level of theory; Baicalein; DPPH test; Electronic, mass and Raman spectra; Iron(III) complex formation; Quercetin

Indexed keywords

ANTIOXIDANT ACTIVITIES; ANTIRADICAL ACTIVITIES; B3LYP/6-31G; B3LYP/6-31G (D, P) LEVEL OF THEORY; BAICALEIN; BUFFERED SOLUTIONS; CHELATING SITES; COMPLEX STRUCTURE; DPPH TEST; EQUILIBRIUM GEOMETRIES; FREE RADICAL SCAVENGING ACTIVITY; FREE STATE; HYDROXY GROUPS; IRON COMPLEX; LIGAND MOLECULES; MECHANISTIC STUDIES; PH-DEPENDENT; QUERCETIN; REACTION STOICHIOMETRY; STRUCTURAL FEATURE; STRUCTURAL MODIFICATIONS; THEORETICAL APPROACH; THEORETICAL CALCULATIONS; THEORETICAL RESULT; VIBRATIONAL ANALYSIS;

CARBONYLATION; CHELATION; COMPLEXATION; FATTY ACIDS; FREE RADICALS; IRON; PHENOLS; RAMAN SPECTROSCOPY; STOICHIOMETRY;

IRON COMPOUNDS;

1,1 DIPHENYL 2 PICRYLHYDRAZYL; BAICALEIN; FREE RADICAL; IRON COMPLEX; QUERCETIN;

ANTIOXIDANT ACTIVITY; AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; MASS SPECTROMETRY; NONHUMAN; PH MEASUREMENT; RAMAN SPECTROMETRY; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION; ULTRAVIOLET SPECTROSCOPY;

EID: 80051795142     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2011.06.008     Document Type: Article

References (35)

1. J.L. Beard, H. Dawson, and D.J. Pinero Iron metabolism: a comprehensive review Nutrition Reviews 54 10 1996 295 317 (Pubitemid 27129673)
2. A.D. Becke Density-functional thermochemistry. II. The role of exact exchange Journal of Chemical Physics 98 1993 5648 5652
3. M.E. Bodini, G. Copia, R. Tapia, F. Leighton, and L. Herrera Iron complexes of quercetin in aprotic medium. Redox chemistry and interaction with superoxide anion radical Polyhedron 18 1999 2233 2239
4. W. Brand-Williams, M.E. Cuvelier, and C. Berset Use of a free radical method to evaluate antioxidant activity Lebensmittel-Wissenschaft und -Technologie 28 1995 25 30
5. M.E. Casida, C. Jamorski, K.C. Casida, and D.R. Salahub Density functional theory, lecture notes in physics Journal of Chemical Physics 108 1998 4439 4450
6. N.C. Cook, and S. Samman Flavonoids-chemistry, metabolism cardioprotective effects and dietary source Journal of Nutritional Biochemistry 7 1996 66 76
7. C. Duen-Suey, J.J. Lee, G. Hsiao, C.Y. Hsieh, Y.J. Tsai, and T.F. Chen Baicalein Induction of hydroxyl radical formation via 12-lipoxygenase in human platelets: An ESR study Journal of Agricultural and Food Chemistry 55 2007 649 655
8. M. Fernandez, T.M. Lurdes, M.H. Florencio, and K.R. Jennings Iron and copper chelation by flavonoids: An electrospray mass spectrometry study Journal of Inorganic Biochemistry 92 2002 105 111 (Pubitemid 35190339)
9. I. Fridovich Science 20 1978 875 880
10. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 09, Revision A.1-SMP 2009 Gaussian Inc. Wallingford CT
11. M. Guo, C. Perez, Y. Wei, E. Rapoza, G. Su, and F. Bou-Abdallah Iron-binding properties of plant phenolics and cranberry's bio-effects Dalton Transactions 2007 4951 4961 (Pubitemid 350015420)
12. H. Hajji, E. Nkhili, V. Tomao, and O. Dangles Interactions of quercetin with iron and copper ions: Complexation and autoxidation Free Radical Research 40 3 2006 303 320 (Pubitemid 43245446)
13. Z. Jurasekova, J.V. Garcia-Ramos, C. Domingo, and S. Sanchez-Cortes Surface-enhanced Raman scattering of flavonoids Journal of Raman Specroscopy 37 2006 1239 1241
14. Z. Jurasekova, A. Torreggiani, M. Tamba, S. Sanchez-Cortes, and J.V. Garcia-Ramos Raman and surface-enhanced Raman scattering (SERS) investigation of the quercetin interaction with metals: Evidence of structural changing processes in aqueous solution and on metal nanoparticles Journal of Molecular Structure 918 2009 129 137
15. M. Leopoldini, I.P. Pitarch, N. Russo, and M. Toscano Structure, conformation, and electronic properties of apigenin, luteolin, and taxifolin antioxidants. A first principle theoretical study Journal of Physical Chemistry A 108 2004 92 96
16. M. Leopoldini, N. Russo, S. Chiodo, and M. Toscano Iron chelation by the powerful antioxidant flavonoid quercetin Journal of Agricultural and Food Chemistry 54 2006 6343 6351 (Pubitemid 44375792)
17. M. Leopoldini, N. Russo, and M. Toscano The molecular basis of working mechanism of natural polyphenolic antioxidants Food Chemistry 125 2011 288 306
18. A.E. Martell, and R.D. Hancock Metal Complexes in Aqueous Solutions 1996 Plenum Publishing Corporation New York
19. L. Mira, M.T. Fernandez, M. Santos, R. Rocha, H. Florencio, and K.R. Jennings Interactions of flavonoids with iron and copper ions: A mechanism for their antioxidant activity Free Radical Research 36 11 2002 1199 1208 (Pubitemid 35230240)
20. C.A. Perez, Y. Wei, and M. Guo Iron-binding and anti-Fenton properties of baicalein and baicalin Journal of Inorganic Biochemistry 103 2009 326 332
21. Pietta, P.G. (1997). Flavonoids in health and disease. In C. A. Rice-Evans, L. Packer, & M. Dekker (Eds.), New York.
22. Pryor, W. A. (1976). Free Radicals in Biology, In W. A. Pryor (Ed.) Academic Press, New York.
23. W. Ren, Z. Qian, H. Wang, L. Zhu, and L. Zhang Flavonoids: Promising anticancer agents Medicinal Chemistry Research 23 4 2003 519 534 (Pubitemid 36706514)
24. C. Rice-Evans, and N. Miller Antioxidant activities of flavonoids as bioactive components of food Biochemical Society Transactions 1996 790 795 (Pubitemid 26306300)
25. M. Suenaga Facio 3D-Graphic program for molecular modeling an visualization of quantum chemical calculations Journal of Comparative Chemistry Japan 4 1 2005 25 32
26. T. Teslova, C. Corredor, R. Livingstone, T. Spataru, R.L. Birke, and J.R. Lombardi Raman and surface-enhanced Raman spectra of flavone and several hydroxy derivatives Journal of Raman Specroscopy 38 2007 802 818
27. J. Tomasi, and M. Persico Molecular interactions in solution: An overview of methods based on continuous distributions of the solvent Chemical Reviews 94 1994 2027 2094 (Pubitemid 124000195)
28. A. Torreggiani, Z. Jurasekova, S. Sanchez-Cortes, and M. Tamba Spectroscopic and pulse radiolysis studies of the antioxidant properties of (+)catechin: metal chelation and oxidizing radical scavenging Journal of Raman Specroscopy 39 2008 265 275
29. A. Torreggiani, M. Tamba, A. Trinchero, and S. Bonora Copper(II)-quercetin complexes in aqueous solutions: Spectroscopic and kinetic properties Journal of Molecular Structure 759 2005 744 747
30. A. Torreggiani, A. Trinchero, M. Tamba, and P. Taddei Raman and pulse radiolysis studies of the antioxidant properties of quercetin: Cu(II) chelation and oxidizing radical scavenging Journal of Raman Specroscopy 36 2005 380 388 (Pubitemid 40717257)
31. P. Trouillas, P. Marsal, D. Siri, R. Lazzaroni, and J.L. Duroux A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: The specificity of the 3-OH site Food Chemistry 97 2006 679 688 (Pubitemid 43181665)
32. G. Varsanayi Assigments for Vibrational Spectra of 700 Benzene Derivates 1974 Adam Hilger London
33. M. Wang, T. Teslova, F. Xu, T. Spataru, J.R. Lombardi, and R.L. Birke Raman and surface enhanced Raman scattering of 3-hydroxyflavone Journal of Physical Chemistry C 111 2007 3038 3043 (Pubitemid 46384315)
34. M. Yoshino, and K. Murakami Interaction of iron with polyphenolic compounds: Application to antioxidant characterization Analytical Biochemistry 257 1998 40 44 (Pubitemid 28117340)
35. Zhurko, G. A.; Zhurko, D. A. (2008). Chemcraft graphical program for working with quantum chemistry results, Chemcraft 1.6, Available from: < http://www.chemcraftprog.com >.