An Jiansong, Pan Nianjuan, Liu Chunyi, Chen Haijiang, Fei Qiang, Gan Xiuhai, Wu Wenneng
School of Food Science and Engineering, Guiyang University Guiyang 550005 China
National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University Guiyang 550025 China.
RSC Adv. 2024 May 20;14(23):16218-16227. doi: 10.1039/d4ra01765j. eCollection 2024 May 15.
In this study, 24 novel ferulic acid derivatives containing 1,3,4-oxadiazole thioether and trifluoromethyl pyrimidine were designed and synthesized. Bioactivity assay showed that some of the target compounds exhibited moderate to good antifungal activity against BD), sp. (PS), (BC), spp. (FS), (FG), and sp. (CS). Especially, compound 6f demonstrated superior antifungal activity against sp., with an EC value of 12.64 μg mL, outperforming pyrimethanil (35.16 μg mL) and hymexazol (27.01 μg mL). Meanwhile, compound 6p showed strong antibacterial activity against pv. citri (XAC) , with an inhibition ratio of 85.76%, which was higher than thiodiazole copper's 76.59% at 100 μg mL. Furthermore, molecular docking simulations elucidated that compound 6f engaged in hydrogen bonding with the succinate dehydrogenase (SDH) enzyme at SER-17, SER-39, ARG-14 and ARG-43 sites, clarifying its mode of action. This study highlights the potential of these novel ferulic acid derivatives as promising agents for controlling fungal and bacterial threats to plant health. To the best of our knowledge, this study represents the first report on the antifungal and antibacterial properties of ferulic acid derivatives containing 1,3,4-oxadiazole thioether and trifluoromethyl pyrimidine skeleton.
在本研究中，设计并合成了24种含1,3,4-恶二唑硫醚和三氟甲基嘧啶的新型阿魏酸衍生物。生物活性测定表明，部分目标化合物对灰葡萄孢（Botrytis cinerea，BC）、尖孢镰刀菌（Fusarium oxysporum，FO）、瓜果腐霉（Pythium aphanidermatum，PA）、立枯丝核菌（Rhizoctonia solani，RS）、终极腐霉（Pythium ultimum，PU）和核盘菌（Sclerotinia sclerotiorum，SS）表现出中等至良好的抗真菌活性。特别是，化合物6f对核盘菌表现出优异的抗真菌活性，其EC50值为12.64 μg/mL，优于嘧霉胺（35.16 μg/mL）和恶霉灵（27.01 μg/mL）。同时，化合物6p对柑橘溃疡病菌（Xanthomonas axonopodis pv. citri，XAC）表现出较强的抗菌活性，抑制率为85.76%，高于100 μg/mL时噻菌铜的76.59%。此外，分子对接模拟表明化合物6f在SER-17、SER-39、ARG-14和ARG-43位点与琥珀酸脱氢酶（SDH）酶形成氢键，阐明了其作用方式。本研究突出了这些新型阿魏酸衍生物作为控制植物健康面临的真菌和细菌威胁的有前景药剂的潜力。据我们所知，本研究是关于含1,3,4-恶二唑硫醚和三氟甲基嘧啶骨架的阿魏酸衍生物的抗真菌和抗菌性能的首次报道。
