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Discovery of Novel Acethydrazide-Containing Flavonol Derivatives as Potential Antifungal Agents
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-07-25 , DOI: 10.1021/acs.jafc.4c02654 Hongyi Chen 1 , Zunyun Jiang 1 , He Tong 1 , Ziyun Mai 1 , Ren Kong 2 , Weihua Zhang 1 , Ming-Zhi Zhang 1 , Kang Chen 1 , Yingguang Zhu 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-07-25 , DOI: 10.1021/acs.jafc.4c02654 Hongyi Chen 1 , Zunyun Jiang 1 , He Tong 1 , Ziyun Mai 1 , Ren Kong 2 , Weihua Zhang 1 , Ming-Zhi Zhang 1 , Kang Chen 1 , Yingguang Zhu 1
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In this study, a series of novel hydrazide-containing flavonol derivatives was designed, synthesized, and evaluated for antifungal activity. In the in vitro antifungal assay, most of the target compounds exhibited potent antifungal activity against seven tested phytopathogenic fungi. In particular, compound C32 showed the best antifungal activity against Rhizoctonia solani (EC50 = 0.170 μg/mL), outperforming carbendazim (EC50 = 0.360 μg/mL) and boscalid (EC50 = 1.36 μg/mL). Compound C24 exhibited excellent antifungal activity against Valsa mali, Botrytis cinerea, and Alternaria alternata with EC50 values of 0.590, 0.870, and 1.71 μg/mL, respectively. The in vivo experiments revealed that compounds C32 and C24 were potential novel agricultural antifungals. 3D quantitative structure–activity relationship (3D-QSAR) models were used to analyze the structure–activity relationships of these compounds. The analysis results indicated that introducing appropriate electronegative groups at position 4 of a benzene ring could effectively improve the anti-R. solani activity. In the antifungal mechanism study, scanning electron microscopy and transmission electron microscopy analyses revealed that C32 disrupted the normal growth of hyphae by affecting the structural integrity of the cell membrane and cellular respiration. Furthermore, compound C32 exhibited potent succinate dehydrogenase (SDH) inhibitory activity (IC50 = 8.42 μM), surpassing that of the SDH fungicide boscalid (IC50 = 15.6 μM). The molecular dynamics simulations and docking experiments suggested that compound C32 can occupy the active site and form strong interactions with the key residues of SDH. Our findings have great potential for aiding future research on plant disease control in agriculture.
中文翻译：
新型含乙酰肼黄酮醇衍生物作为潜在抗真菌剂的发现
在本研究中，设计、合成了一系列新型含酰肼黄酮醇衍生物，并评估了其抗真菌活性。在体外抗真菌测定中，大多数目标化合物对七种测试的植物病原真菌表现出有效的抗真菌活性。特别是，化合物C32对立枯丝核菌表现出最佳的抗真菌活性 (EC 50 = 0.170 μg/mL)，优于多菌灵 (EC 50 = 0.360 μg/mL) 和啶酰菌胺 (EC 50 = 1.36 μg/mL)。化合物C24对苹果腐烂病菌、灰葡萄孢和链格孢菌表现出优异的抗真菌活性，EC 50值分别为0.590、0.870和1.71 μg/mL。体内实验表明化合物C32和C24是潜在的新型农用抗真菌剂。 3D定量构效关系（3D-QSAR）模型用于分析这些化合物的构效关系。分析结果表明，在苯环4位引入适当的电负性基团可有效提高抗茄病菌活性。在抗真菌机制研究中，扫描电镜和透射电镜分析表明， C32通过影响细胞膜的结构完整性和细胞呼吸来破坏菌丝的正常生长。此外，化合物C32表现出有效的琥珀酸脱氢酶（SDH）抑制活性（IC 50 = 8.42 μM），超过SDH杀菌剂啶酰菌胺（IC 50 = 15.6 μM）。 分子动力学模拟和对接实验表明，化合物C32可以占据活性位点，并与SDH的关键残基形成强相互作用。我们的研究结果对于帮助未来农业植物病害控制研究具有巨大潜力。
更新日期：2024-07-25
中文翻译：
新型含乙酰肼黄酮醇衍生物作为潜在抗真菌剂的发现
在本研究中，设计、合成了一系列新型含酰肼黄酮醇衍生物，并评估了其抗真菌活性。在体外抗真菌测定中，大多数目标化合物对七种测试的植物病原真菌表现出有效的抗真菌活性。特别是，化合物C32对立枯丝核菌表现出最佳的抗真菌活性 (EC 50 = 0.170 μg/mL)，优于多菌灵 (EC 50 = 0.360 μg/mL) 和啶酰菌胺 (EC 50 = 1.36 μg/mL)。化合物C24对苹果腐烂病菌、灰葡萄孢和链格孢菌表现出优异的抗真菌活性，EC 50值分别为0.590、0.870和1.71 μg/mL。体内实验表明化合物C32和C24是潜在的新型农用抗真菌剂。 3D定量构效关系（3D-QSAR）模型用于分析这些化合物的构效关系。分析结果表明，在苯环4位引入适当的电负性基团可有效提高抗茄病菌活性。在抗真菌机制研究中，扫描电镜和透射电镜分析表明， C32通过影响细胞膜的结构完整性和细胞呼吸来破坏菌丝的正常生长。此外，化合物C32表现出有效的琥珀酸脱氢酶（SDH）抑制活性（IC 50 = 8.42 μM），超过SDH杀菌剂啶酰菌胺（IC 50 = 15.6 μM）。 分子动力学模拟和对接实验表明，化合物C32可以占据活性位点，并与SDH的关键残基形成强相互作用。我们的研究结果对于帮助未来农业植物病害控制研究具有巨大潜力。
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