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含二异丙醇胺结构的杨梅素衍生物的设计、合成及生物活性研究。

Design, Synthesis, and Biological Activity Studies of Myricetin Derivatives Containing a Diisopropanolamine Structure.

机构信息

State Key Laboratory of Green Pesticide, Center for R&D of Fine Chemicals, Guizhou University, Guiyang 550025, P. R. China.

出版信息

J Agric Food Chem. 2024 Nov 13;72(45):25034-25044. doi: 10.1021/acs.jafc.4c08663. Epub 2024 Nov 5.

Abstract

A series of myricetin derivatives containing diisopropanolamine were designed and synthesized. The in vitro inhibitory effects of the target compounds on 9 fungal pathogens and 3 bacterial pathogens were also evaluated. had the best inhibitory effect against (), with an EC value of 4.9 μg/mL, which was better than zinc-thiazole (ZT: EC = 7.3 μg/mL) and thiodiazole-copper (TC: EC = 65.5 μg/mL); had the best inhibitory effect against . (), with an EC value of 17.2 μg/mL, which was better than azoxystrobin (Az: EC = 22.3 μg/mL). In vivo inhibition tests were performed on kiwifruit for and rice leaves for . At 200 μg/mL, the curative activity of against rice leaf blight was 40.7%, which was better than that of ZT (37.2%) and TC (32.9%), and the protective activity of was 44.8%, which was better than that of ZT (39.5%) and TC (34.6%). The curative activity of against kiwi soft rot disease was 70.1%, which was better than that of Az (62.8%). Preliminary elucidation of the possible mechanisms of action was carried out by experiments on fluorescence microscopy, scanning electron microscopy, formation of biofilms, density functional theory calculations, and so on.

摘要

设计并合成了一系列含有二异丙醇胺的杨梅素衍生物。还评估了目标化合物对 9 种真菌病原体和 3 种细菌病原体的体外抑制作用。

对 ()抑制效果最好,EC 值为 4.9 μg/mL,优于锌噻唑(ZT:EC = 7.3 μg/mL)和噻二唑铜(TC:EC = 65.5 μg/mL);对 ()抑制效果最好,EC 值为 17.2 μg/mL,优于肟醚菌胺(Az:EC = 22.3 μg/mL)。在猕猴桃上进行了活体抑制试验,在水稻叶片上进行了 。在 200 μg/mL 时,化合物 对水稻稻瘟病的治疗活性为 40.7%,优于 ZT(37.2%)和 TC(32.9%),保护活性为 44.8%,优于 ZT(39.5%)和 TC(34.6%)。化合物 对猕猴桃软腐病的治疗活性为 70.1%,优于肟醚菌胺(Az:62.8%)。通过荧光显微镜、扫描电子显微镜、生物膜形成、密度泛函理论计算等实验初步阐明了可能的作用机制。

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