Department of Chemistry, Yuquan Campus, Zhejiang University, No. 38, Zheda Road, Hangzhou 310027, Zhejiang, PR China.
Bioorg Med Chem Lett. 2012 Sep 1;22(17):5744-7. doi: 10.1016/j.bmcl.2012.06.026. Epub 2012 Jul 6.
Twenty five Imine resveratrol analogues (IRAs) were synthesized, replacing the C=C bond in resveratrol with CN bond, as well as substitution modifications on aromatic rings. Radical scavenging activities against DPPH, along with singlet oxygen quenching capacities were evaluated, and further confirmed using density functional theory calculations (DFT). It was found that IRAs bearing ortho-OH on B ring have better radical scavenging activities against DPPH than resveratrol, these compounds were also found to be effective (1)O(2) quenchers. Theoretical studies on the reaction mechanism of these compounds with (1)O(2) suggest that the 1,3-addition to a double bond with a -OH group with the formation of allylic hydroperoxide is the most probable reaction route.
合成了 25 种亚胺白藜芦醇类似物（IRAs），用 CN 键取代白藜芦醇中的 C=C 键，并对芳环进行取代修饰。评估了它们对 DPPH 的清除自由基活性以及单线态氧猝灭能力，并进一步通过密度泛函理论计算（DFT）进行了验证。结果发现，B 环上带有邻位-OH 的 IRAs 对 DPPH 的清除自由基活性优于白藜芦醇，这些化合物也被证明是有效的（1）O2 猝灭剂。这些化合物与（1）O2 的反应机制的理论研究表明，与 -OH 基团形成烯丙基过氧化物的双键的 1,3-加成是最可能的反应途径。
