title: The antiradical activity of some selected flavones and flavonols. Experimental and quantum mechanical study.
abstract: The aim of the study was to examine the antiradical and antioxidant activity of some flavones and flavonols with different models of hydroxylation and methoxylation. Antiradical activity was measured using ABTS and DPPH radicals and ferric ions (FRAP test). The reduction potential of the compounds was also investigated by determination of minimal hydrogen abstraction energy for each of the hydroxyl hydrogens of all compounds using quantum chemistry methods. Quercetin appeared to be a strong antioxidant when the FRAP test was performed and the strongest for ABTS and DPPH tests whereas genkwanin was the weakest antioxidant for three tests (FRAP, ABTS, and DPPH). Flavonols appeared to have much stronger antiradical activity than flavones. An exception was luteolin, which belongs to flavones but exhibited antiradical activity comparable to that of flavonols, probably due to the presence of a hydroxyl group in the B ring at the 3' position next to another hydroxyl group at position 4'. The study using UB3LYP/6-31G(d,p) model chemistry of density functional theory (DFT) showed the lowest hydrogen abstraction energy (HAE) for the hydroxyl group situated at 3' or 5' of myricetin. Based on the experimental results and computational studies, we conclude that the hydroxyl group situated at 4' in the B ring in flavonoids, and to a lesser at the 3' and 3 position in flavonols is the most important for antioxidant activity of flavonoids. We observe strong negative Spearman's rank order correlations between minimal HAE and antiradical activity of flavonoids in all three tests and double-tailed rejection P values are less than 0.001.
authors.affiliation: Department of Pharmacognosy, Wrocław Medical University, ul. Borowska 211, 50-556, Wroclaw, Poland. z.g.sroka@gmail.com.
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Sroka
authors.affiliation: Department of Pharmacognosy, Wrocław Medical University, ul. Borowska 211, 50-556, Wroclaw, Poland.
authors.forename: Beata
authors.initials: B
authors.lastname: Żbikowska
authors.affiliation: Department of Physical Chemistry, Wrocław Medical University, ul. Borowska 211, 50-556, Wroclaw, Poland.
authors.forename: Jerzy
authors.initials: J
authors.lastname: Hładyszowski
mesh_terms: D000975:Antioxidants / Q000737:chemistry*; D047309:Flavones / Q000737:chemistry*; D044948:Flavonols / Q000737:chemistry*; D008956:Models, Chemical; D011789:Quantum Theory; D013329:Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D047309:Flavones; D044948:Flavonols
keywords: Antioxidants; Density functional theory; Flavones; Flavonols; Minimal hydrogen abstraction energy