Department of Chemistry, Josip Juraj Strossmayer University of Osijek, Cara Hadrijana 8a, 31000 Osijek, Croatia.
Department of Chemical-Technological Sciences, State University of Novi Pazar, Vuka Karadžića bb, 36300 Novi Pazar, Serbia.
Food Chem. 2018 Apr 25;246:481-489. doi: 10.1016/j.foodchem.2017.11.100. Epub 2017 Dec 2.
The role of antiradical moieties (catechol, guaiacyl and carboxyl group) and molecular conformation in antioxidative potency of dihydrocaffeic acid (DHCA) and dihydroferulic acid (DHFA) was investigated by density functional theory (DFT) method. The thermodynamic preference of different reaction paths of double (2H/2e) free radical scavenging mechanisms was estimated. Antiradical potency of DHCA and DHFA was compared with that exerted by their unsaturated analogs - caffeic acid (CA) and ferulic acid (FA). Cis/trans and anti-isomers of studied cinnamic acid derivatives may scavenge free radicals via double processes by involvement of catechol or guaiacyl moiety. Carboxyl group of syn-isomers may also participate in the inactivation of free radicals. Gibbs free energies of reactions with various free radicals indicate that syn-DHCA and syn-DHFA, colon catabolites that could be present in systemic circulation in low μM concentrations, have a potential to contribute to health benefits by direct free radical scavenging.
通过密度泛函理论（DFT）方法研究了二氢咖啡酸（DHCA）和二氢阿魏酸（DHFA）中抗自由基部分（儿茶酚、愈创木基和羧基）和分子构象在抗氧化活性中的作用。估计了双（2H/2e）自由基清除机制不同反应途径的热力学偏好。将 DHCA 和 DHFA 的抗自由基能力与它们的不饱和类似物-咖啡酸（CA）和阿魏酸（FA）进行了比较。研究的肉桂酸衍生物的顺/反式和反式异构体可以通过儿茶酚或愈创木基部分的双过程清除自由基。顺式异构体的羧基也可以参与自由基的失活。与各种自由基的反应吉布斯自由能表明，在低μM 浓度下可能存在于全身循环中的结肠代谢物 syn-DHCA 和 syn-DHFA，通过直接清除自由基具有对健康有益的潜力。
