Natural Sesquiterpene Lactone as Source of Discovery of Novel Fungicidal Candidates: Structural Modification and Antifungal Activity Evaluation of Xanthatin Derived from Xanthium strumarium L

作者：Chun Yang, Y. Li, Yuan Zhang, Qiang Hu, Ying Liu, Yangfan Li, Hongcheng Shi, Lili Song, Cao Hui, Xiaojuan Hao, Xiaoyan Zhi · 发表于：Journal of Agricultural and Food Chemistry · 年份：2023 · DOI：10.1021/acs.jafc.3c02435 · 被引用次数：22 · 研究领域：Sesquiterpenes and Asteraceae Studies、Essential Oils and Antimicrobial Activity、Fungal Biology and Applications

As part of our ongoing efforts to discover novel agricultural fungicidal candidates from natural sesquiterpene lactones, in the present work, sixty-three xanthatin-based derivatives containing a arylpyrazole, arylimine, thio-acylamino, oxime, oxime ether, or oxime ester moiety were synthesized. Their structures were well characterized by 1 H and 13 C nuclear magnetic resonance and high-resolution mass spectrometry, while the absolute configurations of compounds 5′ and 6a were further determined by single-crystal X-ray diffraction. Meanwhile, the antifungal activities of the prepared compounds against several phytopathogenic fungi were investigated using the spore germination method and the mycelium growth rate method in vitro . The bioassay results illustrated that compounds 5, 5′, and 15 exhibited excellent inhibitory activity against the tested fungal spores and displayed remarkable inhibitory effects on fungal mycelia. Compounds 5 and 5′ exhibited more potent inhibitory activity (IC 50 = 1.1 and 24.8 μg/mL, respectively) against the spore of Botrytis cinerea than their precursor xanthatin (IC 50 = 37.6 μg/mL), wherein the antifungal activity of compound 5 was 34-fold higher than that of xanthatin and 71-fold higher than that of the positive control, difenoconazole (IC 50 = 78.5 μg/mL). Notably, compound 6′a also demonstrated broad-spectrum inhibitory activity against the four tested fungal spores. Meanwhile, compounds 2, 5, 8, and 15 showed prominent inhibitory activity ag...