含羟基苯甲酸甲酯的顺、反丁烯二酸酯类化合物的合成及抑菌活性

Synthesis and Antimicrobial Activity of Novel cis/trans-But-2-Enedioic Acid Esters Containing a Hydroxybenzoic Acid Methyl Ester Moiety

以顺、反丁烯二酸单酯和o,m,p-羟基苯甲酸甲酯为起始原料合成了6种新型的含羟基苯甲酸甲酯单元的顺、反丁烯二酸酯类化合物,目的在于发现新的具有抑制食品相关细菌和真菌生长能力的生物活性分子。产物结构经液相色谱-质谱联用(liquid chromatography mass spectrometer,LC-MS)、核磁共振(nuclear magnetic resonance,NMR)表征和元素分析。体外抑菌活性实验结果表明,所有合成的化合物对8种供试菌有着较好的抑菌效果,化合物4a的抑菌活性最强(最低抑菌浓度(minimum inhibitory concentration,MIC)≤75μg/mL),化合物4a对酿酒酵母、黄曲霉和产黄青霉的MIC分别为25、37.5、37.5μg/mL。

Six novel cis/trans-but-2-enedioic acid esters containing a hydroxybenzoic acid methyl ester moiety weresynthesized as potential food preservatives, aiming to discover the new bioactive molecules that can kill food-related bacteria and fungi, and their structures were characterized by liquid chromatography-mass spectrometry(LC-MS), nuclear magnetic resonance(NMR) and elemental analysis. The antimicrobial activity assays in vitro showed that these compounds had strong bioactivity against all eight microorganisms tested. Among the most promising antibacterial and antifungal compounds, 4-(methoxycarbonyl) phenyl methyl fumarate(4a) showed the best antimicrobial activity, and it was effective against S. cerevisiae, A. flavus and P. chrysogenum with minimal inhibition concentration(MIC) of 25, 37.5 and 37.5 μg/mL, respectively.