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New aspects of the antioxidant properties of phenolic acids: a combined theoretical and experimental approach

机译:酚酸抗氧化性能的新方面:理论和实验相结合的方法

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Ferulic acid is widely distributed in the leaves and seeds of cereals as well as in coffee, apples, artichokes, peanuts, oranges and pineapples. Like numerous other natural polyphenols it exhibits antioxidant properties. It is known to act as a free radical scavenger by H atom transfer from the phenolic OH group. In the present joint experimental and theoretical studies we studied a new mechanism to explain such activities. Ferulic acid can indeed act by radical addition on the α,β-double bond. On the basis of the identification of metabolites formed in an oxidative radiolytic solution and after DFT calculations, we studied the thermodynamic and kinetic aspects of this reaction. Addition and HAT reactions were treated as competitive reactions. The possibility of dimer formation was also investigated from a theoretical point of view; the high barriers we obtained contribute to explaining why we did not observe those compounds as major radiolytic compounds. The DPPH free radical scavenging capacity of ferulic acid and the oxidative products was measured and is discussed on the basis of DFT calculations (BDEs and spin densities).
机译:阿魏酸广泛分布在谷物的叶子和种子中以及咖啡,苹果,朝鲜蓟,花生,橙子和菠萝中。像许多其他天然多酚一样,它具有抗氧化性能。已知通过从酚式OH基团转移H原子起自由基清除剂的作用。在目前的联合实验和理论研究中,我们研究了解释这种活动的新机制。阿魏酸确实可以通过在α,β-双键上加成自由基来起作用。在鉴定氧化辐射溶液中形成的代谢物并进行DFT计算后,我们研究了该反应的热力学和动力学方面。加和HAT反应被视为竞争反应。还从理论角度研究了二聚体形成的可能性。我们获得的高壁垒有助于解释为什么我们没有观察到这些化合物是主要的辐射分解化合物。测量了阿魏酸和氧化产物的DPPH自由基清除能力,并在DFT计算(BDE和自旋密度)的基础上进行了讨论。

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