Czech J. Food Sci., 2012, 30(2):153-163 | DOI: 10.17221/447/2010-CJFS

Antioxidant activity coefficient, mechanism, and kinetics of different derivatives of flavones and flavanones towards superoxide radical

Safeer AHMED, Faria SHAKEEL
Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan

A systematic investigation of the electrochemically generated superoxide radical (O2●-) has been conducted in the presence of some flavonoids. Cyclic voltammetry was used to generate O2●- by reducing the molecular oxygen in DMSO at room temperature. The scavenging of the radical was monitored by the decrease in anodic or/and cathodic currents while linearly increasing the concentration of the flavonoid. The strength of interaction was quantified in terms of the binding constant (Kb)values ranging from 1 × 102 and 5 × 103M-1. The antioxidant activity coefficient (Kao) was calculated from the linear part of the plot of 'current decrease vs. flavonoid concentration'. Radical scavenging mechanism of the antioxidant was proposed and discussed in terms of the structure activity relationship. Nicholson-Shain method was employed to estimate the bimolecular homogeneous kinetics and on this basis control use of antioxidant is pointed out.

Keywords: antioxidant activity coefficient; flavonoids; binding constant; homogeneous kinetics; cyclic voltammetry

Published: April 30, 2012  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
AHMED S, SHAKEEL F. Antioxidant activity coefficient, mechanism, and kinetics of different derivatives of flavones and flavanones towards superoxide radical. Czech J. Food Sci. 2012;30(2):153-163. doi: 10.17221/447/2010-CJFS.
Share...
Download citation
  • BibTeX (.bib)
  • Bookends (.ris)
  • EasyBib (.ris)
  • EndNote (.enw)
  • EndNote 8 (.xml)
  • ISI WoS (.isi)
  • Medlars (.medlars)
  • Mendeley (.ris)
  • MODS (.xml)
  • Papers (.ris)
  • RefWorks (.txt)
  • RefManager (.ris)
  • RIS (.ris)
  • MS Word (.xml)
  • Zotero (.ris)
    • Open full article

    References

    1. Ahmed S., Khan A.Y., Qureshi R. Subhani M.S. (2007): Hydrogen bonding association in the electroreduced intermediates of benzoquinones and naphthoquinones. Russian Journal of Electrochemistry, 43: 811-819. Go to original source...
    2. Arshad N., Janjua N.K., Ahmed S., Khan A.Y., Skibsted L.H. (2009): Electrochemical investigations of antioxidant interactions with radical anion and dianion of 1,3-dinitrobenzene. Electrochimica Acta, 54: 6184-6189. Go to original source...
    3. Bourvellec C.L. Hauchard D., Darchen A., Burgot J.L., Abasq M.L. (2008): Validation of new method using the reactivity of electrogenerated superoxide radical in the antioxidant capacity determination of flavonoids. Talanta, 75: 1098-1103. Go to original source... Go to PubMed...
    4. Collins C.M., Leventis C.S., Canalas M.T., Leventis N. (2000): A cyclic voltammetric study of the proton abstraction from selected aromatic ketones by superoxide. Electrochimica Acta, 45: 2049-2059. Go to original source...
    5. Edenharder R., Grünhage D. (2003): Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102. Mutation Research, 540: 1-18. Go to original source... Go to PubMed...
    6. Evans C.R. (2004): Flavonoids and isoflavones: absorption, metabolism, and bioactivity. Free Radical Biology and Medicine, 36: 827-828. Go to original source... Go to PubMed...
    7. Feng Q., Li N. Q., Jiang Y.Y. (1997): Electrochemical studies of porphyrin interacting with DNA and determination of DNA. Analytica Chimica Acta, 344: 97-104. Go to original source...
    8. Feroci, G., Fini, A. (2007): Voltammetric investigation of the interactions between superoxide ion and some sulfur amino acids. Inorganica Chemica Acta, 360: 1023-1031. Go to original source...
    9. Gao, Z. Huang K., Yang X., Xu H. (1999): Free radical scavenging and antioxidant activities of flavonoids extracted from the radix of Scutellaria baicalensis Georgi. Biochimica et Biophysica Acta, 1472: 643-650. Go to original source... Go to PubMed...
    10. Harborne J.B. (1994): The Flavonoids Advances in ReSearch Since 1986, Chapmann and Hall, New York. Go to original source...
    11. Harold E.M., Rigelhof, F., Marquart L., Prakash A., Kanter M., Aruna P., Kanter M. (2000): Antioxidant content of whole grain breakfast cereals, fruits and vegetables. Journal of the American College of Nutrition, 19: 312S-319S. Go to original source... Go to PubMed...
    12. Heim K.E., Tagliaferro A.R., Bobilya D.J. (2002): Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. Journal of Nutritional Biochemistry, 13: 572-584. Go to original source... Go to PubMed...
    13. Kohen R., Vellaichamy E., Hrbac J., Gati I., Tirosh O. (2000): Quantification of the overall reactive oxygen species scavenging capacity of biological fluids and tissues. Free Radical Biology and Medicine, 28: 871-879. Go to original source... Go to PubMed...
    14. Korotkova E.I., Karbainov Y.A., Avramchik O.A. (2003): Investigation of antioxidant and catalytic properties of some biological active substances by voltammetry. Analytical and Bioanalytical Chemistry, 375: 465-468. Go to original source... Go to PubMed...
    15. Koyama J., Morita I., Kobayashi N., Konoshima T., Takasaki, M., Osakai T., Tokuda H. (2008): Correlation between oxidation potentials and inhibitory effects on Epstein-Barr virus activation of flavonoids. Cancer Letters, 263: 61-66. Go to original source... Go to PubMed...
    16. Macias-Ruvalcaba N.A., Gonzalez I., Martinez M.A. (2004): Evolution from hydrogen bond to proton transfer pathways in the electroreduction of α-NH-quinones in acetonitrile. Journal of Electrochemical Society, 151: E110-E118. Go to original source...
    17. Madsen H.L., Nielsen B.R., Bertelsen G., Skibsted L.H. (1996): Screening of antioxidative activity of spices. A comparison between assays based on ESR spin trapping and electrochemical measurement of oxygen consumption. Food Chemistry, 57: 331-337. Go to original source...
    18. Mohammad M., Khan A. Y., Subhani M.S., Bibi N., Ahmed S., Saleemi S. (2001): Kinetics and electrochemical studies on superoxide. Research on Chemical Intermediates. 27: 259-267. Go to original source...
    19. Moure A., Cruz J.M., Franco D., Sineiro J., Parajo J.C. (2001): Natural antioxidants from residual sources. Food Chemistry, 72: 145-171. Go to original source...
    20. Nanni E.D., Jr., Stallings M.D., Sawyer D.T. (1980): Does superoxide ion oxidize catechol α-tochopherol, and ascorbic acid by direct electron transfer? Journal of the American Chemical Society, 102: 4481-4485. Go to original source...
    21. Nicholson R.S., Shain I. (1964): Theory of stationary electrode polarography single scan and cyclic methods applied to reversible, irreversible, and kinetic systems. Journal of Analytical Chemistry, 36: 706-723. Go to original source...
    22. Ortiz M.E., Nunez-Vergara L.J., Squella J.A. (2002): Cyclic voltammetric behaviour of the O2/O2▪- redox couple at a HMDE and its interaction with nisoldipine. Journal of Electroanalytical Chemistry, 519: 46-52. Go to original source...
    23. Shakeel F. (2010): Antioxidant behaviour of some flavonoids and plant extracts towards superoxide radical. [M.Phil Thesis.] Department of Chemistry, Quaid-iAzam University, Islamabad.
    24. Suna T., Xieb W., Xu P. (2004): Superoxide anion scavenging activity of graft chitosan derivatives. Carbohydrate Polymers, 58: 379-382. Go to original source...
    25. Temraz A., Eltantawy W. (2008): Characterization of antioxidant activity of extract from Artemisia vulgaris. Pakistan Journal of Pharmaceutical Sciences, 21: 321-326.
    26. Trombino S., Serini S., Nicuolo F.D., Celleno L., Ando S., Picci N., Calviello G., Palozza P. (2004): Antioxidant effect of ferulic acid in isolated membranes and intact cells: synergistic interactions with α-tocopherol, β-carotene, and ascorbic acid. Journal of Agriculture and Food Chemistry, 52: 2411-2420. Go to original source... Go to PubMed...
    27. Tsushima M., Tokuda K., Ohsaka T. (1994): Use of hydrodynamic chronocoulometry for simultaneous determination of diffusion coefficients and concentration of dioxygen in various media. Analytical Chemistry, 66: 4551-4556. Go to original source...
    28. Vasudevan D., Wendt H. (1995): Electroreduction of oxygen in aprotic media. Journal of Electroanalytical Chemistry, 392: 69-74. Go to original source...
    29. Weber M.L. (2009): New therapeutic aspects of flavones: The anticancer properties of Scutellaria and its main active constituents Wogonin, Baicalein and Baicalin. Cancer Treatment Reviews, 35: 57-68. Go to original source... Go to PubMed...
    30. Ziyatdinova G.K., Gil'metdinova D.M., Budnikov G.K. (2005): Reactions of superoxide anion radical with antioxidants and their use in voltammetry. Journal of Analytical Chemistry, 60: 56-59. Go to original source...

    This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY NC 4.0), which permits non-comercial use, distribution, and reproduction in any medium, provided the original publication is properly cited. No use, distribution or reproduction is permitted which does not comply with these terms.


    Return to the content