Journal
FOOD CHEMISTRY
Volume 268, Issue -, Pages 220-232Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.foodchem.2018.06.071
Keywords
Antimicrobial activity; Synthesis; Sorbic acid derivatives; Benzoic acid derivatives; Amino acid esters
Funding
- Fundamental Research Funds for the Central Universities, SCUT, China [2017MS075]
- National Key R&D Program of China, China [2017YFD0400404]
- Collaborative Innovation Major Special Projects of Guangzhou City, China [201604020007]
- Guangdong Provincial Science and Technology Plan Projects, China [2015A020209016, 2016A040403040]
- International and Hong Kong - Macau - Taiwan Collaborative Innovation Platform of Guangdong Province on Intelligent Food Quality Control and Process Technology & Equipment, China [2015KGJHZ001]
- Guangdong Provincial R & D Centre for the Modern Agricultural Industry on Non-destructive Detection and Intensive Processing of Agricultural Products
- Common Technical Innovation Team of Guangdong Province on Preservation and Logistics of Agricultural Products [2016LM2154]
- Innovation Centre of Guangdong Province for Modern Agricultural Science and Technology on Intelligent Sensing and Precision Control of Agricultural Product Qualities
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A series of sorbic and benzoic acid amide derivatives were synthesized by conjugating sorbic acid (SAAD, a(l)-a(7)) or benzoic acid (BAAD b(1)-b(6)) with amino acid esters and their antimicrobial activities were investigated against Escherichia coll., 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(7)) 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(7) 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.
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