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含哌嗪磺酰基的基于抗烟草花叶病毒活性的黄酮醇衍生物:设计、合成及作用机制研究

Anti-TMV activity based flavonol derivatives containing piperazine sulfonyl: Design, synthesis and mechanism study.

作者信息

Sun Zhiling, Zeng Wei, Qiu Yujiao, Hu Yuzhi, Zhou Qing, Hu Chunmei, Wang Yuhong, Xue Wei

机构信息

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

出版信息

Mol Divers. 2025 Jan 22. doi: 10.1007/s11030-025-11109-6.

DOI:10.1007/s11030-025-11109-6
PMID:39841318
Abstract

A series of flavonoid derivatives containing piperazine sulfonate were designed and synthesized. The results of antiviral experiments in vivo showed that some target compounds had good inhibitory effect on tobacco mosaic virus (TMV). The EC values of S15 and S19 curative activity were 174.5 and 110.4 μg/mL, respectively, which were better than 253.7 μg/mL of Ningnanmycin (NNM). The EC values of S4 and S19 protection activity were 140.3 and 116.1 μg/mL, respectively, better than that of NNM (247.1 μg/mL). Microscale thermophoresis (MST) and molecular docking experiments showed that S19 had a good molecular binding force with TMV. Transmission electron microscopy (TEM) results show that S19 can fracture TMV particles and affect self-assembly. S19 treatment had almost no effect on the growth of seeds and seedlings, and can change the content of chlorophyll malondialdehyde (MDA) and superoxide dismutase (SOD) in tobacco to a certain extent, and improve the disease resistance of tobacco.

摘要

设计并合成了一系列含哌嗪磺酸盐的黄酮类衍生物。体内抗病毒实验结果表明,部分目标化合物对烟草花叶病毒(TMV)具有良好的抑制作用。S15和S19治疗活性的EC值分别为174.5和110.4μg/mL,优于宁南霉素(NNM)的253.7μg/mL。S4和S19保护活性的EC值分别为140.3和116.1μg/mL,优于NNM(247.1μg/mL)。微量热泳动(MST)和分子对接实验表明,S19与TMV具有良好的分子结合力。透射电子显微镜(TEM)结果显示,S19可使TMV颗粒断裂并影响其自组装。S19处理对种子和幼苗的生长几乎没有影响,且能在一定程度上改变烟草中叶绿素、丙二醛(MDA)和超氧化物歧化酶(SOD)的含量,提高烟草的抗病性。

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