Structure-antioxidant activity relationship of ferulic acid derivatives: Effect of carbon side chain characteristic groups
Structure-antioxidant activity relationship of ferulic acid derivatives: Effect of carbon side chain characteristic groups
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DOI：
10.1021/jf0261452
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发表时间：
2003-03-26
影响因子：
6.1
通讯作者：
Tsimidou, MZ
中科院分区：
文献类型：
--
作者：
Nenadis, N;Zhang, HY;Tsimidou, MZ
采用实验和计算方法研究了阿魏酸衍生物碳侧链末端特征基团（-COOH、-CHO、-CH_2 OH、-CH_3和-COOC_2 H_5）诱导的生物合成相关阿魏酸衍生物抗氧化活性的差异。对DPPH自由基的清除活性的相对顺序是异丁香酚类似于松柏醇远远大于阿魏酸类似于松柏醛类似于阿魏酸乙酯。在散装油自动氧化（45 ℃）的活性得到了相同的顺序。在O/W乳液自氧化，亲脂性的酚类是决定因素，因为最小极性的化合物轴承-CH 3和-COOC 2 H5是最有效的。基于密度泛函理论（DFT）计算的O-H键离解焓（BIDE）和电离势（IP）值的活性顺序与实验的自由基清除顺序和特征基团的给/吸电子性质一致。其他分子描述符不能补充实验结果。
Differences in the antioxidant activity of some biosynthetically related ferulic acid derivatives induced by the presence of characteristic groups (-COOH, -CHO, -CH2OH, -CH3, and -COOC2H5) at the end of their carbon side chain were investigated using both experimental and computational methods. The relative order of the scavenging activity toward the DPPH radical derived from kinetic studies was isoeugenol similar to coniferyl alcohol much greater than ferulic acid similar to coniferyl aldehyde similar to ethyl ferulate. In bulk oil autoxidation (45 degreesC) the same order of activity was obtained. In the o/w emulsion autoxidation, lipophilicity of the phenols was the determining factor because the least polar compounds bearing -CH3 and -COOC2H5 were the most effective ones. The order of activity based on the O-H bond dissociation enthalpy (BIDE) and ionization potential (IP) values, calculated by the density functional theory (DFT) method, was in accordance with the experimental radical scavenging order and with the electron-donating/withdrawing properties of the characteristic groups. Other molecular descriptors could not complement the experimental findings.