Theoretical study of the antioxidant properties of pyridoxine.
Theoretical study of the antioxidant properties of pyridoxine.
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DOI：
10.1021/jp065115p
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发表时间：
2006-11
期刊：
影响因子：
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通讯作者：
J. M. Matxain;Mikael Ristilä;Å. Strid;L. Eriksson
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文献类型：
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作者：
J. M. Matxain;Mikael Ristilä;Å. Strid;L. Eriksson
作为能够清除活性氧（ROS）的抗氧化剂的分子在活细胞中至关重要。最近发现了吡哆醇（维生素 B6）的抗氧化特性。在本研究中，我们在密度泛函理论水平（泛函 B3LYP 和 MPW1B95）分析了吡哆醇对 ROS (.-)OH、(.-)OOH 和 (.-)O(2)- 的反应性。已经研究了两种反应类型如下：芳香环原子的加成反应和氢/质子夺取。我们的结果表明，(.-)OH 是最具反应性的物质，而 (.-)OOH 显示出低反应性，并且 (.-)O2(-) 根本不与吡哆醇发生反应。最放能的反应是那些从 CH(2)OH 基团或环键 OH 基团中除去 (.-)H 的反应，范围为 -33 至 -39 kcal/mol。最放能的加成反应是通过攻击与氮键合的碳原子而发生的，但能量增益仅为 6 kcal/mol。
Molecules acting as antioxidants capable of scavenging reactive oxygen species (ROS) are of utmost importance in the living cell. The antioxidative properties of pyridoxine (vitamin B6) have recently been discovered. In this study, we have analyzed the reactivity of pyridoxine toward the ROS (.-)OH, (.-)OOH, and (.-)O(2)- at the density functional theory level (functionals B3LYP and MPW1B95). Two reaction types have been studied as follows: addition to the aromatic ring atoms and hydrogen/proton abstraction. Our results show that (.-)OH is the most reactive species, while (.-)OOH displays low reactivity and (.-)O2(-) does not react at all with pyridoxine. The most exergonic reactions are those where (.-)H is removed from the CH(2)OH groups or the ring-bound OH group and range from -33 to -39 kcal/mol. The most exergonic addition reactions occur by attacking the carbon atoms bonded to nitrogen but with an energy gain of only 6 kcal/mol.