The antioxidant potential of modified quercetins and quercetin-metal complexes

Corinne M. Spickett, Agnieszka Wojton, Maria Kopacz, Barbara Oleksyn

Research output: Contribution to journalConference abstract

Abstract

Quercetin is a naturally occurring polyphenol compound present in grapes, red wine, tea, apples and some vegetables. Like other flavonoids, it has been found to have antioxidant activity in studies in vitro, although there is still much debate about the bioavailability of flavonoids in the diet and their in vivo antioxidant activity. In general, it is thought that the antioxidant efficiency of polyphenols increases with increasing hydroxylation of the rings, but there have been few studies of other substitutions. We have prepared several derivatives of quercetin, to test the effect of modification on their antioxidant potential. Sodium salts of quercetin-5-sulfonate and quercetin-5,8-sulfonate, and transition metal complexes of quercetin-5-sulfonate were analysed for their total antioxidant potential using the FRAP assay, and compared to unmodified quercetin. It was found that quercetin-5-sulfonate complexes with Zn, Cu(II), Fe(II) and Mg were all significantly better antioxidants than quercetin, quercetin-5-sulfonate was comparable to quercetin, whereas the sodium salt of quercetin-5,8-sulfonate had a decreased total antioxidant potential. Kinetic studies of the FRAP reaction showed no significant differences between quercitin and any of the derivatives. The reaction of all the quercetins in the FRAP assay was found to be slower to reach completion than ascorbate, and appeared to have biphasic
characteristics. These results suggest that transition metal ions may facilitate the transfer of electrons from the polyphenol ring system to the oxidant, while substitution with S03 is electron-withdrawing and destabilizes the ring system. This is important both for understanding the antioxidant ability of flavonoids, and for the design of novel antioxidant compounds. Further work is being carried out to assess the ability of the quercetin complexes to protect cultured cells from oxidative stress.
Original languageEnglish
Article number556
Pages (from-to)S209-S210
Number of pages2
JournalFree Radical Biology and Medicine
Volume33
Issue number2, Suppl.1
Early online date29 Jun 2002
DOIs
Publication statusPublished - 15 Jul 2002
Event11th Meeting of the Society for Free Radical Research International - Paris, France
Duration: 16 Jul 2002 → …

Keywords

  • antioxidant potential
  • modified quercetins
  • quercetin-metal complexes
  • Pharmacy and materia medica

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  • Phagocyte oxidation of phospholipids: comparison of hydroperoxide, chlorohydrin and epoxyisoprostane formation by LC-MS

    Spickett, C. M., Jerlich, A., Schaur, R. J. & Pitt, A. R., 15 Jul 2002, In : Free Radical Biology and Medicine. 33, 2, Suppl.1, p. S145 1 p., 379.

    Research output: Contribution to journalConference abstract

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