杂环取代的 α-亚甲基-γ-丁内酯衍生物的合成、抗真菌活性和 3D-QSAR,Journal of Agricultural and Food Chemistry

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杂环取代的 α-亚甲基-γ-丁内酯衍生物的合成、抗真菌活性和 3D-QSAR
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-07-11 , DOI: 10.1021/acs.jafc.3c02117
Luwei Li _{1,

2} , Deyou Yang _{1,

2} , Heng Li ₁ , Guangyou Chen _{1,

2} , Peng Lei _{1,

2} , Yanqing Gao _{1,

2} , Juntao Feng _{1,

2,

3}

Affiliation

利用活性植物骨架开发杀菌剂是应对植物病原菌抗性的有效方法之一。基于我们前期的发现，根据首次在植物Carpesium macrocephalum中发现的抗真菌分子carabrone，设计了一系列含有杂环和苯环的新型α-亚甲基-γ-丁内酯（MBL）衍生物。合成了目标化合物，并系统研究了其对病原真菌的抑制活性及其作用机制。几种化合物对多种真菌表现出有希望的抑制活性。最有效的化合物38对苹果腐霉( V. mali )的EC ₅₀值为0.50 mg/L ，比商业杀菌剂恶唑菌酮更有效。化合物38对苹果枝条的苹果小叶弧菌的保护作用优于恶唑菌酮，50 mg/L时抑制率为47.9%。生理生化结果表明，化合物38通过引起细胞变形和收缩、减少细胞内线粒体数量、增厚细胞壁以及增加细胞膜的通透性来抑制V. mali 。基于三维定量构效关系（3D-QSAR）分析表明，大体积且带负电的基团的引入有利于新型MBL衍生物的抗真菌活性。这些发现表明化合物38可能是值得进一步研究的新型杀菌剂的潜在候选者。

"点击查看英文标题和摘要"

Heterocycle-Substituted α-Methylene-γ-Butyrolactones Derivatives Synthesis, Antifungal Activity, and 3D-QSAR

Developing fungicides from active botanical skeletons is one of the effective methods to tackle the resistance of plant pathogens. Based on our previous discoveries, a series of novel α-methylene-γ-butyrolactone (MBL) derivatives containing heterocycles and phenyl rings were designed according to the antifungal molecule carabrone first discovered in plant Carpesium macrocephalum. The target compounds were synthesized, and the inhibitory activity against pathogenic fungi as well as the mechanism of action were then systematically investigated. Several compounds showed promising inhibitory activities against a variety of fungi. The most potent compound 38 exhibited the EC₅₀ value of 0.50 mg/L against Valsa mali (V. mali), which was more effective than that of commercial fungicide famoxadone. The protective effect of compound 38 against V. mali on apple twigs was superior to that of famoxadone, with an inhibition rate of 47.9% at 50 mg/L. The physiological and biochemical results showed that compound 38 inhibits V. mali by causing cell deformation and contraction, reducing the number of intracellular mitochondria, thickening the cell wall, as well as increasing the permeability of the cell membrane. Based on three-dimensional quantitative structure–activity relationship (3D-QSAR) analyses, it was shown that the introduction of the bulky and negatively charged groups favored the antifungal activity of the novel MBL derivatives. These findings suggest that compound 38 can be a potential candidate for novel fungicides worthy of further investigation further.

更新日期：2023-07-11

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