Density functional study of the antioxidant activity of some recently synthesized resveratrol analogues
Density functional study of the antioxidant activity of some recently synthesized resveratrol analogues
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DOI：
10.1016/j.foodchem.2013.05.071
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发表时间：
2013-12-01
期刊：
影响因子：
8.8
通讯作者：
Toscano, Marirosa
中科院分区：
文献类型：
--
作者：
Mazzone, Gloria;Malaj, Naim;Toscano, Marirosa
在本文中，我们研究了两个主要的工作机制（氢原子和单电子转移）的五个新的潜在的抗氧化剂类似物顺式白藜芦醇。计算了甲醇中O-H键的离解能和电离势。得到的结果表明，所有的检查化合物是更有效的抗氧化剂比它们所衍生的分子，主要是由于它们的共轭度较高，并有能力离域的it-电子，这有助于稳定的自由基物种。这些稳定作用的增强部分是由于在顺式-白藜芦醇的C2'和C6碳原子之间引入单键，其产生新的中心芳环。然而，羟基的数量，特别是儿茶酚部分的存在仍然是决定自由基清除潜力的顺序的最重要的特征。还报道和讨论了光谱UV-Vis表征。(C)2013爱思唯尔有限公司保留所有权利。
In this paper we have investigated the two main working mechanisms (H atom and single-electron transfer) of five new potential antioxidant analogues of cis-resveratrol. The O-H bond dissociation energy (BDE) and ionization potential (IP) key parameters were computed in methanol. Results obtained indicate that all the examined compounds are more efficient antioxidants than the molecule from which they derive, mainly due to their higher degree of conjugation and the capability to delocalize the it-electrons which contribute to the stabilization of the radical species. The enhancement of these stabilizing effects is in part a result of the introduction of a single bond between the C2' and C6 carbon atoms of cis-resveratrol that generates a new central aromatic ring. However, the number of hydroxyl groups and in particular the presence of the catechol moiety remains the most significant features in determining the order of radical scavenging potentiality. Spectroscopic UV-Vis characterization is also reported and discussed. (C) 2013 Elsevier Ltd. All rights reserved.