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Who Is the King? The α ‐Hydroxy‐ β ‐oxo‐ α , β ‐enone Moiety or the Catechol B Ring: Relationship between the Structure of Quercetin Derivatives and Their Pro‐Oxidative Abilities
Author(s) -
Liu PeiYan,
Li Kun,
Zhang Ji,
Zhang DaWei,
Lin HongHui,
Yu XiaoQi
Publication year - 2010
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200900032
Subject(s) - chemistry , moiety , quercetin , catechol , stereochemistry , oxidative phosphorylation , dna , antioxidant , biochemistry
Quercetin and other flavonoids have been reported to exhibit both antioxidant and pro‐oxidant properties. Most studies about the pro‐oxidative ability were conducted in the presence of metal ions, and the essential functional moiety of quercetin responsible for the pro‐oxidative effect is still unclear. In this study, we evaluated the pro‐oxidative abilities in the absence of metal ions of two quercetin derivatives, i.e. , quercetin‐3′‐O‐ β ‐ D ‐glucoside ( 1 ) and quercetin‐3‐ O ‐ β ‐ D ‐glucoside ( 2 ), by assessing DNA cleavage and HO . ‐radical production. The binding mode between these compounds and DNA was studied by fluorescence and viscometric titrations. The results showed that 1 can efficiently induce oxidative damage to plasmid DNA, while 2 shows poor activity. Both 1 and 2 bind to DNA via groove‐binding. These results proved that the α ‐hydroxy‐ β ‐oxo‐ α , β ‐enone moiety contributes to the pro‐oxidative activity of quercetin.