Antioxidant Properties of Kynurenines: Density Functional Theory Calculations.
作者： Aleksandr V. Zhuravlev , Gennady A. Zakharov , Boris F. Shchegolev , Elena V. Savvateeva-Popova
DOI: 10.1371/JOURNAL.PCBI.1005213
关键词:
摘要: Kynurenines, the main products of tryptophan catabolism, possess both prooxidant and anioxidant effects. Having multiple neuroactive properties, kynurenines are implicated in development neurological cognitive disorders, such as Alzheimer's, Parkinson's, Huntington's diseases. Autoxidation 3-hydroxykynurenine (3HOK) its derivatives, 3-hydroxyanthranilic acid (3HAA) xanthommatin (XAN), leads to hyperproduction reactive oxygen species (ROS) which damage cell structures. At same time, 3HOK 3HAA have been shown be powerful ROS scavengers. Their ability quench free radicals is believed result from presence aromatic hydroxyl group able easily abstract an electron H-atom. In this study, redox properties for several natural synthetic antioxidants calculated at different levels density functional theory gas phase water solution. Hydroxyl bond dissociation enthalpy (BDE) ionization potential (IP) appear lower than xanthurenic (XAA), phenolic antioxidants, ascorbic acid. BDE IP compounds with their precursors without group. The reaction rate H donation *O-atom phenoxyl radical (Ph-O*) methyl peroxy (Met-OO*) decreases following rankings: ~ > XAAOXO XAAENOL. absolute value Met-OO* addition ring antioxidant increases 3HAA* < 3HOK* XAAOXO* XAAENOL*. Thus, high scavenging activity can explained by easiness H-atom abstraction transfer O-atom radical, rather kynurenine radical.
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