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Synthesis and antimicrobial activities of novel sorbic and benzoic acid amide derivatives
Food Chemistry ( IF 8.5 ) Pub Date : 2018-06-18 , DOI: 10.1016/j.foodchem.2018.06.071
Qingyi Wei , Xiaomei Wang , Jun-Hu Cheng , Guangxiang Zeng , Da-Wen Sun

A series of sorbic and benzoic acid amide derivatives were synthesized by conjugating sorbic acid (SAAD, a1a7) or benzoic acid (BAAD b1b6) with amino acid esters and their antimicrobial activities were investigated against Escherichia coli, Bacillus subtilis and Staphylococcus aureus, mixed bacteria from rancid milk, Saccharomyces cerevisiae, and Aspergillus niger. The antimicrobial activity of sorbic acid amides was better than that of benzoic acid amides. The minimum inhibitory concentrations (MIC) of compound isopropyl N-[1-oxo-2, 4-hexadien-1-yl]-L-phenylalaninate (a7) were 0.17 mM against B. subtilis, and 0.50 mM against S. aureus, while the MIC values of sorbic acid were more than 2 mM respectively. Also, compound a7 displayed pH-independent antimicrobial activity in the range of pH 5.0–9.0 and was effective at pH 9.0. These results demonstrated that the conjugation of sorbic acid with amino acid esters led to significant improvement of in vitro antimicrobial attributes, but little effect was observed for benzoic acid amide derivatives.



中文翻译:

新型山梨酸和苯甲酸酰胺衍生物的合成和抑菌活性

通过将山梨酸(SAAD,a 1a 7)或苯甲酸(BAAD b 1b 6)与氨基酸酯缀合来合成一系列山梨酸和苯甲酰胺衍生物,并研究了它们对大肠杆菌芽孢杆菌的抗菌活性。枯草芽孢杆菌金黄色葡萄球菌,腐乳,酿酒酵母黑曲霉中的混合细菌。山梨酰胺的抗菌活性优于苯甲酰胺。化合物的最小抑制浓度(MIC)异丙基N- [1-氧代-2,4-己二烯-1-基] -L-苯基丙氨酸甲酯(一个7)为0.17毫针对枯草芽孢杆菌,和0.50毫摩尔对金黄色葡萄球菌,而山梨酸的MIC值分别大于2 mM。同样,化合物a 7在pH 5.0-9.0的范围内表现出与pH无关的抗菌活性,并且在pH 9.0时有效。这些结果表明,山梨酸与氨基酸酯的缀合导致体外显着改善。 抗菌特性,但对苯甲酰胺衍生物几乎没有观察到作用。

更新日期:2018-06-18
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