新型山梨酸和苯甲酸酰胺衍生物的合成及抗菌活性。
Synthesis and antimicrobial activities of novel sorbic and benzoic acid amide derivatives.
机构信息
School of Food Science and Engineering, South China University of Technology, Guangzhou 510641, PR China; Academy of Contemporary Food Engineering, South China University of Technology, Guangzhou Higher Education Mega Center, Guangzhou 510006, PR China; Engineering and Technological Research Centre of Guangdong Province on Intelligent Sensing and Process Control of Cold Chain Foods, Guangzhou Higher Education Mega Centre, Guangzhou 510006, PR China.
School of Food Science and Engineering, South China University of Technology, Guangzhou 510641, PR China; Academy of Contemporary Food Engineering, South China University of Technology, Guangzhou Higher Education Mega Center, Guangzhou 510006, PR China; Engineering and Technological Research Centre of Guangdong Province on Intelligent Sensing and Process Control of Cold Chain Foods, Guangzhou Higher Education Mega Centre, Guangzhou 510006, PR China; Food Refrigeration and Computerized Food Technology (FRCFT), Agriculture and Food Science Centre, University College Dublin, National University of Ireland, Belfield, Dublin 4, Ireland.
出版信息
Food Chem. 2018 Dec 1;268:220-232. doi: 10.1016/j.foodchem.2018.06.071. Epub 2018 Jun 18.
A series of sorbic and benzoic acid amide derivatives were synthesized by conjugating sorbic acid (SAAD, a-a) or benzoic acid (BAAD b-b) 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 (a) 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 a 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.
一系列山梨酸和苯甲酸酰胺衍生物通过将山梨酸（SAAD，a-a）或苯甲酸（BAAD，b-b）与氨基酸酯结合合成，并研究了它们对大肠杆菌、枯草芽孢杆菌和金黄色葡萄球菌、酸败牛奶中的混合细菌、酿酒酵母和黑曲霉的抗菌活性。山梨酸酰胺的抗菌活性优于苯甲酸酰胺。化合物异丙基 N-[1-氧代-2,4-己二烯-1-基]-L-苯丙氨酸酯（a）对枯草芽孢杆菌的最小抑菌浓度（MIC）为 0.17mM，对金黄色葡萄球菌的 MIC 值为 0.50mM，而山梨酸的 MIC 值均大于 2mM。此外，化合物 a 在 pH 5.0-9.0 范围内表现出 pH 独立的抗菌活性，在 pH 9.0 时也具有效果。这些结果表明，山梨酸与氨基酸酯的结合导致体外抗菌特性显著改善，但苯甲酸酰胺衍生物的效果很小。
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