DFT study of quercetin activated forms involved in antiradical, antioxidant, and prooxidant biological processes.
Quercetin, one of the most representative flavonoid compounds, is involved in antiradical, antioxidant, and prooxidant biological processes. Despite a constant increase of knowledge on both positive and negative activities of quercetin, it is unclear which activated form (quinone, semiquinone, or deprotonated) actually plays a role in each of these processes. Structural, electronic, and energetic characteristics of quercetin, as well as the influence of a copper ion on all of these parameters, are studied by means of quantum chemical electronic structure calculations. Introduction of thermodynamic cycles together with the role of coreactive compounds, such as reactive oxygen species, gives a glimpse of the most probable reaction schemes. Such a theoretical approach provides another hint to clarify which reaction is likely to occur within the broad range of quercetin biological activities.
Fiorucci
Sébastien
S
Laboratoire de Chimie des Molécules Bioactives et des Arômes, UMR-CNRS 6001, Faculté des Sciences,Université de Nice-Sophia Antipolis, 06108 Nice Cedex 2, France.
Golebiowski
Jérôme
J
Cabrol-Bass
Daniel
D
Antonczak
Serge
S
D000975:Antioxidants; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003300:Copper / Q000494:pharmacology; D016166:Free Radical Scavengers; D016877:Oxidants; D011794:Quercetin / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013816:Thermodynamics
D000975:Antioxidants; D016166:Free Radical Scavengers; D016877:Oxidants; D003300:Copper; D011794:Quercetin