Improvement of Antioxidative Activity of Resveratrol by Calix[4]arene-like Tetramer: A Theoretical Study

Publication date: Available online 17 December 2018Source: Computational and Theoretical ChemistryAuthor(s): Lilin Lu, Zhuhua Ruan, Jiaqi Ni, Jun Chen, Hongfei Shu, Yanqun Wang, Yi LiuAbstractResveratrol is a natural antioxidant in a wide variety of plant species, developing an effective strategy to further improve its antioxidative activity has attracted enormous research attention in recent years. In this work, tetra-(3,5-dihydroxy)styryl-calix[4]arene (TSC, a calix[4]arene-like tetramer of resveratrol) has been theoretically studied at the DFT-BP86/6-311+G(d,p) level of theory. The results demonstrates that TSC has highly symmetrical molecular geometry with four equivalent resveratrol units, the 4’-O-H and 4’-C-O bonds were elongated and distinct deviation from planarity was observed in four resveratrol units in TSC. More interestingly, TSC has remarkably lower 4’-OH BDE, IP, and PA of 4’-phenolate than those of resveratrol, indicating that TSC exhibits much more excellent antioxidative activities than resveratrol. Spin density in 4’-phenoxyl radical and cation radical are delocalized over whole molecular skeleton of TSC, thus leading to more stable radical species than that of resveratrol. The topologies analysis of unpaired electron occupying orbitals reveals that calix[4]arene skeleton plays very important role in delocalization of unpaired electron. Molecular simplification studies proved that the synergistic effect of calix[4]arene skeleton, the A benzene ri...
Source: Computational and Theoretical Chemistry - Category: Chemistry Source Type: research