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Theoretical Chemistry Accounts

, Volume 127, Issue 1–2, pp 69–80 | Cite as

Mechanistic pathways for the reaction of quercetin with hydroperoxy radical

  • Zoran S. Marković
  • Jasmina M. Dimitrić MarkovićEmail author
  • Ćemal B. Doličanin
Regular Article

Abstract

The extensive theoretical study of the interaction of one of the most abundant and reactive flavonols, quercetin, with hydroperoxy radical (HOO·), using the M052X/6-31 + Gd, p level of theory, was performed. Results indicating that quercetin is not a planar molecule are in accord with the X-ray analysis. The applied method successfully reproduces the bond dissociation enthalpy, and reveals that the reaction of quercetin with the hydroperoxy radical is governed by a hydrogen atom transfer mechanism. It is confirmed that the 3′OH and 4′OH are the most reactive sites, and that the reaction in the 3′OH position is faster than that in the 4′OH position.

Keywords

Quercetin DFT M052X Hydroperoxy radical 

Notes

Acknowledgments

The authors acknowledge financial support by the Ministry of Science and Environmental of Republic of Serbia (Grant No. 142025). Authors would like to thank all the Referees, especially to the anonymous Referee 2, for the detailed and critical reading of our manuscript.

Supplementary material

214_2009_706_MOESM1_ESM.doc (279 kb)
Supplementary material 1 (DOC 279 kb)

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Copyright information

© Springer-Verlag 2009

Authors and Affiliations

  • Zoran S. Marković
    • 1
  • Jasmina M. Dimitrić Marković
    • 2
    Email author
  • Ćemal B. Doličanin
    • 1
  1. 1.Department of Bio-chemical and Medical SciencesState University of Novi PazarNovi PazarRepublic of Serbia
  2. 2.Faculty of Physical ChemistryUniversity of BelgradeBelgradeRepublic of Serbia

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