Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 15, Issue 22, Pages 7058-7065Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2007.07.013
Keywords
antioxidarit; hydroquinone; electron spin resonance spectroscopy; kinetics
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This study was undertaken to investigate the free radical -scavenging and antioxidant activities of various structurally related hydroquinones including hydroxynaplithalenones and dihydroxyanthracenones. Electron spin resonance spectroscopy and spin trapping techniques were used to evaluate the ability of hydroquinones to scavenge hydroxyl, diphenylpicrylhydrazyl. and galvinoxyl radicals. In addition, the oxygen radical absorbing capacity assay using fluorescein (ORAC-FL) was used to obtain the relative antioxidant capacity of these radicals. The rate constants of the first H atom abstraction by 2,2-diphenyl-2-picrylhydrazyl (k(2)), were obtained tinder pseudo-first-order conditions. The free radical-scavenging activities and k(2), values discriminate well between hydroxynaphthalenones and dihydroxyanthracenones, showing that the latter have better antioxidant properties. The aforementioned experimental data agree with quanturn-chemical results demonstrating the relevance of intramolecular H bonding to radical-scavenging activities. (C) 2007 Elsevier Ltd. All rights reserved.
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