Department of Chemistry, Faculty of Science, Alzahra University, PO Box: 19835-389, Vanak, Tehran, Iran.
Carbohydr Res. 2011 May 1;346(6):739-44. doi: 10.1016/j.carres.2011.01.021. Epub 2011 Jan 28.
A quantum mechanical approach has been used to shed light on the antioxidative mechanism for scavenging hydroxyl radicals (()OH) and superoxide radicals (O2-) by rutin in the solution phase. Density-functional theory (DFT) using B(3)LYP and UB(3)LYP functional and split-valance 6-311+G(∗∗) basis sets were used to optimize rutin and its different radical forms. Analysis of the theoretical bond dissociation enthalpy (BDE) values for all OH sites of rutin in solution clearly shows the importance of the B-ring and the 3'-OH and 4'-OH groups in the antioxidant activity. We have also investigated the spin density of the radicals to determine the delocalization possibilities. The results of the calculations showed that the oxidation of rutin by both the hydroxyl radical and superoxide radical is an exothermic reaction. In all calculations solvent effects were considered using a polarized continuum model (PCM).
一种量子力学方法被用来阐明芦丁在溶液相中清除羟基自由基(()OH)和超氧自由基(O2-)的抗氧化机制。使用 B(3)LYP 和 UB(3)LYP 函数以及分裂价 6-311+G(∗∗)基组的密度泛函理论 (DFT) 用于优化芦丁及其不同的自由基形式。对芦丁在溶液中所有 OH 位的理论键离解焓 (BDE) 值的分析清楚地表明了 B 环以及 3'-OH 和 4'-OH 基团在抗氧化活性中的重要性。我们还研究了自由基的自旋密度，以确定离域的可能性。计算结果表明，芦丁被羟基自由基和超氧自由基氧化都是放热反应。在所有计算中，使用极化连续模型 (PCM) 考虑了溶剂效应。
