Synthesis and antimicrobial activities of novel sorbic and benzoic acid amide derivatives. 2018

Qingyi Wei, and Xiaomei Wang, and Jun-Hu Cheng, and Guangxiang Zeng, and Da-Wen Sun
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.

A series of sorbic and benzoic acid amide derivatives were synthesized by conjugating sorbic acid (SAAD, a1-a7) or benzoic acid (BAAD b1-b6) 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.

UI MeSH Term Description Entries
D008826 Microbial Sensitivity Tests Any tests that demonstrate the relative efficacy of different chemotherapeutic agents against specific microorganisms (i.e., bacteria, fungi, viruses). Bacterial Sensitivity Tests,Drug Sensitivity Assay, Microbial,Minimum Inhibitory Concentration,Antibacterial Susceptibility Breakpoint Determination,Antibiogram,Antimicrobial Susceptibility Breakpoint Determination,Bacterial Sensitivity Test,Breakpoint Determination, Antibacterial Susceptibility,Breakpoint Determination, Antimicrobial Susceptibility,Fungal Drug Sensitivity Tests,Fungus Drug Sensitivity Tests,Sensitivity Test, Bacterial,Sensitivity Tests, Bacterial,Test, Bacterial Sensitivity,Tests, Bacterial Sensitivity,Viral Drug Sensitivity Tests,Virus Drug Sensitivity Tests,Antibiograms,Concentration, Minimum Inhibitory,Concentrations, Minimum Inhibitory,Inhibitory Concentration, Minimum,Inhibitory Concentrations, Minimum,Microbial Sensitivity Test,Minimum Inhibitory Concentrations,Sensitivity Test, Microbial,Sensitivity Tests, Microbial,Test, Microbial Sensitivity,Tests, Microbial Sensitivity
D000577 Amides Organic compounds containing the -CO-NH2 radical. Amides are derived from acids by replacement of -OH by -NH2 or from ammonia by the replacement of H by an acyl group. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amide
D000890 Anti-Infective Agents Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. Anti-Infective Agent,Anti-Microbial Agent,Antimicrobial Agent,Microbicide,Microbicides,Anti-Microbial Agents,Antiinfective Agents,Antimicrobial Agents,Agent, Anti-Infective,Agent, Anti-Microbial,Agent, Antimicrobial,Agents, Anti-Infective,Agents, Anti-Microbial,Agents, Antiinfective,Agents, Antimicrobial,Anti Infective Agent,Anti Infective Agents,Anti Microbial Agent,Anti Microbial Agents
D013011 Sorbic Acid Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses. Hexadienoic Acid,Propenylacrylic Acid,Potassium Sorbate,Sodium Sorbate,Acid, Hexadienoic,Acid, Propenylacrylic,Acid, Sorbic,Sorbate, Potassium,Sorbate, Sodium
D013211 Staphylococcus aureus Potentially pathogenic bacteria found in nasal membranes, skin, hair follicles, and perineum of warm-blooded animals. They may cause a wide range of infections and intoxications.
D019817 Benzoic Acid A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. Potassium Benzoate,Ucephan,Acid, Benzoic,Benzoate, Potassium

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