School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300401, China.
Molecules. 2022 Oct 13;27(20):6875. doi: 10.3390/molecules27206875.
A series of oxazinyl flavonoids were synthesized on the basis of flavone. The structures of all target compounds were characterized by H NMR, C NMR, and HRMS. The effect of the different substituent on the N-position of oxazinyl flavonoids against tobacco mosaic virus (TMV) activities and plant pathogen activities was systematically investigated. In vivo anti-TMV activity showed that most of the compounds showed moderate-to-excellent antiviral activities against TMV at 500 μg/mL. Compounds , , -, and - showed better antiviral activities than ribavirin (a commercially available antiviral agent) and apigenin. In particular, compounds and even displayed slightly higher activities than ningnanmycin, which were expected to become new antiviral candidates. Antiviral mechanism research by molecular docking exhibited that compounds and could interact with TMV CP and inhibit virus assembly. Then, the antifungal activities of these compounds against six kinds of plant pathogenic fungi were tested, and the results showed that these oxazinyl flavonoids had broad-spectrum fungicidal activities. Compounds exhibited antifungal activity of up to 91% against and might become a candidate drug for new fungicides.
基于黄酮类化合物，合成了一系列恶嗪基黄酮类化合物。所有目标化合物的结构均通过 1H NMR、13C NMR 和高分辨质谱（HRMS）进行了表征。系统研究了不同取代基在恶嗪基黄酮的 N 位上对烟草花叶病毒（TMV）活性和植物病原菌活性的影响。体内抗 TMV 活性表明，大多数化合物在 500μg/mL 时对 TMV 表现出中等至优异的抗病毒活性。化合物 、 、 、 对 TMV 的抗病毒活性优于利巴韦林（一种市售抗病毒药物）和芹菜素。特别是，化合物 和 甚至表现出略高于宁南霉素的活性，有望成为新的抗病毒候选药物。分子对接的抗病毒机制研究表明，化合物 和 可以与 TMV CP 相互作用并抑制病毒组装。然后，测试了这些化合物对 6 种植物病原菌的抑菌活性，结果表明这些恶嗪基黄酮类化合物具有广谱的杀菌活性。化合物 对 具有高达 91%的抑菌活性，可能成为新型杀菌剂的候选药物。
