Wu Lulu, Shi Lijun, Fan Liangxin, Pan Zhenliang, Zhao Zhonglin, Su Hui, Wang Caixia, Yang Nan, Xu Cuilian, Yang Guoyu
College of Sciences, Henan Agricultural University, Zhengzhou, 450002, P. R. China.
Henan Province Tobacco Company Pingdingshan Company, Pingdingshan, 467000, P. R. China.
Chem Biodivers. 2024 Nov;21(11):e202401052. doi: 10.1002/cbdv.202401052. Epub 2024 Sep 26.
A series of diversified glucosamine derivatives (3a-3y) was synthesized and their antifungal activity was examined against four kinds of phytopathogens, Fusarium graminearum (F. graminearum), Fusarium moniliforme (F. moniliforme), Curvularia. lunata (C. lunata), and Rhizoctonia solani (R. solani) which cause seriously economic losses worldwide by affecting crops. The compound 3o showed remarkable antifungal activity against F. graminearum with EC value of 3.96 μg/mL, compared to the standard drug triadimefon (10.1 μg/mL). 3D-QSAR model with the statistically recommended values (r=0.915, q=0.872) showed that positive charge group or bulky group in the benzyl ring was favorable for the antifungal activity. Enzyme activity assays confirmed that 3o had a moderate inhibition of trehalase with inhibition rate of 51.4 % at 5 μg/mL, which is comparable to those of commercial inhibitor validamycin A with inhibition rate of 83.3 %. Molecular docking analysis revealed that 3o also had a hydrogen bond interaction with key amino acid residue compared to validoxylamine.
合成了一系列多样化的氨基葡萄糖衍生物（3a - 3y），并检测了它们对四种植物病原体的抗真菌活性，这四种病原体分别是禾谷镰刀菌（F. graminearum）、串珠镰刀菌（F. moniliforme）、新月弯孢菌（C. lunata）和立枯丝核菌（R. solani），它们通过影响农作物在全球范围内造成严重的经济损失。与标准药物三唑酮（10.1 μg/mL）相比，化合物3o对禾谷镰刀菌表现出显著的抗真菌活性，其EC值为3.96 μg/mL。具有统计学推荐值（r = 0.915，q = 0.872）的3D - QSAR模型表明，苄环上的正电荷基团或庞大基团有利于抗真菌活性。酶活性测定证实，3o对海藻糖酶有中度抑制作用，在5 μg/mL时抑制率为51.4%，与商业抑制剂井冈霉素A的抑制率83.3%相当。分子对接分析表明，与井冈霉胺相比，3o还与关键氨基酸残基存在氢键相互作用。
