European Journal of Medicinal Chemistry ( IF 6.7 ) Pub Date : 2020-03-20 , DOI: 10.1016/j.ejmech.2020.112253 Guan-Zhou Yang , Jian Zhang , Jing-Wen Peng , Zhi-Jun Zhang , Wen-Bin Zhao , Ren-Xuan Wang , Kun-Yuan Ma , Jun-Cai Li , Ying-Qian Liu , Zhong-Min Zhao , Xiao-Fei Shang
The prevention and control of plant diseases and insect pests is the most crucial issue facing crop protection. To discover novel pesticide candidates with diverse chemical structures from natural products, a series of luotonin A analogues were designed, synthesized and evaluated for their antifungal and insecticidal activities. Most of these compounds exhibited potent activity against Botrytis cinerea, Magnaporthe oryzae and Aphis craccivora. Among them, the antifungal activity of compound 10s against B. cinerea was comparable to azoxystrobin (EC50 = 0.09 mM) and against M. oryzae (EC50 = 0.19 mM) was slightly weaker than that of azoxystrobin (EC50 = 0.17 mM). Compounds 10k and 10o are the most active compounds against A. craccivora having identical mortality value of 42.05% at 50 μg/mL, respectively, which were slightly lower than pymetrozine (51.14%) at the same concentration. Revealed morphological changes of the fungal cell surface by scanning electron microscopy indicated that luotonin A analogues might exert their antifungal activity by destroying fungal cell membrane and cell wall. Furthermore, the results of the in vivo protective and curative activities of the compound 10s against S. sclerotiorum and B. cinerea showed that the curative effect was stronger than its protective effect and the curative effects reached 67.17% and 73.82% at 80 μg/mL respectively. The above results further demonstrated the potential of luotonin A analogues as novel fungicides and insecticides.
中文翻译:
发现作为有效杀菌剂和杀虫剂的褪黑素A类似物:受天然生物碱启发的设计,合成和生物学评估
预防和控制植物病虫害是作物保护面临的最关键问题。为了从天然产物中发现具有多种化学结构的新型农药候选物,设计,合成并评估了一系列的褪黑素A类似物的抗真菌和杀虫活性。这些化合物大多数显示出对灰葡萄孢,稻瘟病菌和蚜虫的有效活性。其中,化合物10s对灰葡萄孢的抗真菌活性可与嘧菌酯(EC 50 = 0.09 mM)相媲美,而对米曲霉(EC 50 = 0.19 mM)的抗真菌活性则比嘧菌酯(EC50 = 0.17 mM)。化合物10k和10o是针对曲霉的最具活性的化合物,在50μg/ mL下的死亡率相同,分别为42.05%,略低于在相同浓度下的pymetrozine(51.14%)。扫描电子显微镜显示的真菌细胞表面形态变化表明,褪黑素A类似物可能通过破坏真菌细胞膜和细胞壁发挥其抗真菌活性。此外,化合物10s对葡萄球菌和灰葡萄孢菌的体内保护和治疗活性的结果结果表明,在80μg/ mL下,治疗效果强于保护作用,分别达到67.17%和73.82%。上述结果进一步证明了褪黑素A类似物作为新型杀真菌剂和杀虫剂的潜力。