Russian Journal of Physical Chemistry A

, Volume 93, Issue 13, pp 2656–2660 | Cite as

The Study of Mg(II) Ion Influence on Catechol Autoxidation in Weakly Alkaline Aqueous Solution

  • G. M. NikolićEmail author
  • S. C. Živanović
  • N. S. Krstić
  • M. G. Nikolić


High performance liquid chromatography with diode array detection (HPLC-DAD) and electron spin resonance (ESR) spectroscopy were used to study Mg(II) ion influence on the autoxidation of catechol in weakly alkaline solution. The presence of Mg(II) ions greatly enhanced the catechol autoxidation rate and probably influenced the mechanism of reaction thus enabling formation of reaction products not obtained in the absence of metal ions. Consecutive formation of 1,2-benzoquinone, 2,3-oxanthrenediol, and 2,3-oxanthrenedione with intermediate o-semiquinone anion radicals during the initial stages of catechol autoxidation was suggested based on the detailed analysis of experimental HPLC-DAD and ESR data. The results of this study may help in better understanding of autoxidation of some biologically important catecholic molecules in real systems, where Mg(II) ions are ubiquitously present. Because of the possible toxicity of simple quinone molecules, it is important that the formation of relatively stable quinoid autoxidation products were detected in this study.


catechol autoxidation magnesium ion 



This work was partially supported by the Ministry for Science and Technological Development of the Republic of Serbia (grant no. 172044).


  1. 1.
    S. Quideau, D. Deffieux, C. Douat-Casassus, and L. Pouységu, Angew. Chem. Int. Ed. 50, 586 (2011).CrossRefGoogle Scholar
  2. 2.
    D. P. Yang, H. F. Ji, G. Y. Tang, W. Ren, and H. Y. Zhang, Molecules 12, 578 (2007).Google Scholar
  3. 3.
    G. P. Maier, C. M. Bernt, and A. Butler, Biomater. Sci. 6, 332 (2018).CrossRefGoogle Scholar
  4. 4.
    M. Friedman and H. S. Jürgens, J. Agric. Food Chem. 48, 2101 (2000).CrossRefGoogle Scholar
  5. 5.
    J. Balla, T. Kiss, and R. F. Jameson, Inorg. Chem. 31, 58 (1992).CrossRefGoogle Scholar
  6. 6.
    P. García, C. Romero, M. Brenes, and A. Garrido, J. Agric. Food Chem. 44, 2101 (1996).CrossRefGoogle Scholar
  7. 7.
    G. M. Nikolić, P. I. Premović, and R. S. Nikolić, Spectrosc. Lett. 31, 327 (1998).CrossRefGoogle Scholar
  8. 8.
    A. V. Lebedev, M. V. Ivanova, A. A. Timoshin, and E. K. Ruuge, ChemPhysChem 8, 1863 (2007).CrossRefGoogle Scholar
  9. 9.
    E. Nikhili, M. Loonis, S. Mihai, H. El Hajji, and O. Dangles, Food Funct. 5, 1186 (2014).CrossRefGoogle Scholar
  10. 10.
    C. P. Monteiro, C. N. Matias, M. Bicho, H. Santa-Clara, and M. J. Laires, Magnes. Res. 29, 161 (2016).PubMedGoogle Scholar
  11. 11.
    S. C. Živanović, R. S. Nikolić, and G. M. Nikolić, Acta Fac. Med. Naiss. 33, 163 (2016).Google Scholar
  12. 12.
    S. C. Živanovic, R. S. Nikolić, D. A. Kostic, and G. M. Nikolić, Oxid. Commun. 40, 581 (2017).Google Scholar
  13. 13.
    S. C. Živanović, A. M. Veselinović, Ž. J. Mitić, and G. M. Nikolić, New J. Chem. 42, 6256 (2018).CrossRefGoogle Scholar
  14. 14.
    L. V. Volod’ko, A. I. Komyak, A. A. Min’ko, B. A. Tatarinov, and P. A. Matusevich, J. Appl. Spectrosc. 24, 717 (1976).CrossRefGoogle Scholar
  15. 15.
    R. Hoskins, J. Chem. Phys. 23, 1975 (1955).CrossRefGoogle Scholar
  16. 16.
    D. R. Eaton, Inorg. Chem. 3, 1268 (1964).CrossRefGoogle Scholar
  17. 17.
    C. C. Felix and R. C. Sealy, J. Am. Chem. Soc. 104, 1555 (1982).CrossRefGoogle Scholar
  18. 18.
    W. G. C. Forsyth, V. C. Quesnel, and J. B. Roberts, Biochim. Biophys. Acta 37, 322 (1960).CrossRefGoogle Scholar
  19. 19.
    M. B. McBride and F. J. Sikora, J. Inorg. Biochem. 39, 247 (1990).CrossRefGoogle Scholar
  20. 20.
    A. Naidja, P. M. Huang, and J.-M. Bollag, Soil Sci. Soc. Am. J. 62, 188 (1998).CrossRefGoogle Scholar
  21. 21.
    F. Solano, New J. Sci. 2014, 498276 (2014).CrossRefGoogle Scholar
  22. 22.
    J. L. Bolton and T. Dunlap, Chem. Res. Toxicol. 30, 13 (2017).CrossRefGoogle Scholar
  23. 23.
    T. M. Penning, Toxicol. Res. 6, 740 (2017).CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • G. M. Nikolić
    • 1
    Email author
  • S. C. Živanović
    • 2
  • N. S. Krstić
    • 3
  • M. G. Nikolić
    • 3
  1. 1.Department of Chemistry, Faculty of Medicine, University of NišNišSerbia
  2. 2.Research Center for Biomedicine, Faculty of Medicine, University of NišNišSerbia
  3. 3.Department of Chemistry, Faculty of Sciences and Mathematics, University of NišNišSerbia

Personalised recommendations