Theoretical Study of the Antioxidant Properties of Pyridoxine

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• 作者：Jon M. Matxain ; Mikael Ristil&auml ; &Aring ; ke Strid ; Leif A. Eriksson
• 刊名：Journal of Physical Chemistry A
• 出版年：2006
• 出版时间：December 7, 2006
• 年：2006
• 卷：110
• 期：48
• 页码：13068 - 13072
• 全文大小：134K
• 年卷期：v.110,no.48(December 7, 2006)
• ISSN：1520-5215

文摘

Molecules acting as antioxidants capable of scavenging reactive oxygen species (ROS) are of utmost importancein the living cell. The antioxidative properties of pyridoxine (vitamin B₆) have recently been discovered. Inthis study, we have analyzed the reactivity of pyridoxine toward the ROS ^{ges/entities/bull.gif">}OH, ^{ges/entities/bull.gif">}OOH, and ^{ges/entities/bull.gif">}O₂^- at the densityfunctional theory level (functionals B3LYP and MPW1B95). Two reaction types have been studied asfollows: addition to the aromatic ring atoms and hydrogen/proton abstraction. Our results show that ^{ges/entities/bull.gif">}OH isthe most reactive species, while ^{ges/entities/bull.gif">}OOH displays low reactivity and ^{ges/entities/bull.gif">}O₂^- does not react at all with pyridoxine.The most exergonic reactions are those where ^{ges/entities/bull.gif">}H is removed from the CH₂OH groups or the ring-bound OHgroup and range from -33 to -39 kcal/mol. The most exergonic addition reactions occur by attacking thecarbon atoms bonded to nitrogen but with an energy gain of only 6 kcal/mol.