Journal
FOOD CHEMISTRY
Volume 131, Issue 2, Pages 508-512Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.foodchem.2011.09.014
Keywords
Quercetin derivative; Courmaric acid derivative; Quantitative structure-activity relationship; Prooxidant activity
Funding
- National Natural Science Foundation of China [31071638]
- Chinese Academy of Sciences [KSCX2-EW-J-28, 201014, 2009B040600004]
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In this work, quercetin, p-courmaric acid and their derivatives were chosen to evaluate the prooxidant activity in NADPH/peroxidase/H(2)O(2) and DNA cleavage systems. The balance between antioxidant and prooxidant effect was not apparent. The number of hydroxyl groups, hydrophilicity, steric hindrance, concentration and affinity to peroxidase were critical for the prooxidation behaviour of tested compounds. Ortho-methoxy substitution led to a decreased prooxidant activity for p-courmaric acid. The DNA cleavage activity was in a decreasing order, quercetin = rutin > p-courmaric acid > ferulic acid > quercetin 3-O-glucoside. By calculation of Delta E((LUMO-HOMO)) and Delta HOF, the reactivity of forming phenoxyl radicals was quercetin > rutin > quercetin 3-O-glucoside, which was in agreement with their DNA cleavage activities. The prooxidant activity order of p-courmaric acid and ferulic acid was in contrast to their reactivities of forming phenoxyl radical. The logP difference should play a critical role in the prooxidation behaviour. (C) 2011 Elsevier Ltd. All rights reserved.
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