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Interaction of quercetin with copper ions: complexation, oxidation and reactivity towards radicals

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Abstract

Quercetin, one of the most common dietary flavonols, was investigated in the presence of Cu(II) ions in methanolic solution in order to obtain some explanation on the mechanism interaction and its action against free radical-mediated damage. The spectroscopic studies (UV–VIS, IR, ESI–MS) were used to assess the extent to which it undergo complex formation through chelation or modification through oxidation. The reaction of quercetin with Cu(II) resulted in the formation of 1:1 metal–ligand complex (λmax = 436 nm) through the carbonyl oxygen and 3-OH group in C ring. Then quercetin is oxidized to the benzoquinone type products. The addition of EDTA destroyed the complex but did not regenerate the whole original spectrum of quercetin. From the other hand, the presence of EDTA inhibits formation of copper–quercetin complex and quercetin oxidation. The antioxidant activity of the Q + Cu solutions was evaluated by using 2,2-diphenyl-1-picrylhydrazyl radical (DPPH∙) radical scavenging method and from an electrochemical point of view. The complex is much more effective as free radical scaveninger than the free flavonoid.

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Acknowledgments

The authors would like to thank the Structural Research Laboratory at the Department of Chemistry, University of Warsaw for using HPLC–MS. SRL has been established with financial support from European Regional Development Found in the Sectorial Operational Programme “Improvement of the competitiveness of Enterprises” project No. WPK-1/1.4.3./1/2004/72/72/165/2005/U.

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  1. Department of Chemistry, University of Warsaw, Warsaw, Poland

    Anna Pękal, Magdalena Biesaga & Krystyna Pyrzynska

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  1. Anna Pękal
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  2. Magdalena Biesaga
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  3. Krystyna Pyrzynska
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Correspondence to Krystyna Pyrzynska.

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Pękal, A., Biesaga, M. & Pyrzynska, K. Interaction of quercetin with copper ions: complexation, oxidation and reactivity towards radicals. Biometals 24, 41–49 (2011). https://doi.org/10.1007/s10534-010-9372-7

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  • DOI: https://doi.org/10.1007/s10534-010-9372-7

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