Efficacy of fatty acid amide derivatives against listeria monocytogenes

Authors: Yosief, Hailemichael; HUSSAIN, SYED - Oak Ridge Institute For Science And Education (ORISE); Sarker, Majher; Annous, Bassam

Submitted to: ChemistrySelect
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 10/7/2020
Publication Date: 10/22/2020
Citation: Yosief, H.O., Hussain, S.A., Sarker, M.I., Annous, B.A. 2020. Efficacy of fatty acid amide derivatives against listeria monocytogenes. ChemistrySelect. https://doi.org/10.1002/slct.202003501.
DOI: https://doi.org/10.1002/slct.202003501

Interpretive Summary: Fatty acids are naturally abundant compounds with diverse and potent biological activities. In this work, the lauric acid, myristic acid and palmitic acid were chemically modified to generate pyrrolidine fatty acid amide derivatives which were then evaluated for their antibacterial activity against a common food-borne harmful bacterial called Listeria monocytogenes (LMC). Chemically synthesized amide derivative of Lauric (LAPY) and myristic (MYPY) acids exhibited time and concentration dependent inhibitory activity against LMC. Treatment with 15 ppm of LAPY for 4 to 10 min completely inhibited the growth of LMC. Similarly, treating LMC with MYPY resulted in significant reduction to the best of our knowledge, this is the first study to demonstrate that the aforementioned amide derivative of lauric and myristic acids have excellent inhibitory activity against LMC strains. Therefore, this amide derivatives of lauric acid and myristic acid could be considered as alternative antibacterial agents to control listeria growth in food products.

Technical Abstract: Fatty acids are naturally abundant molecules with diverse and potent biological activities. Taking advantage of the double bond and the carboxylic acid functional groups present in fatty acids, chemical modifications are commonly performed to explore or enhance their novel biological activities. In this work, the carboxylic acid functional group of lauric acid, myristic acid and palmitic acid was modified with heterocyclic amines to generate fatty acid amide derivatives which were then evaluated for their antibacterial activity against the cocktail of four different Listeria monocytogenes (LMC) strains. Pyrrolidine amide derivative of Lauric (LAPY) and myristic (MYPY) acids exhibited time and concentration dependent activity against LMC strains. Treatment with 15 ppm of LAPY for 2 min reduced the LMC population by average of 4.0 log CFU/ml, whereas 4, 6 and 10 min treatment completely inhibited the growth. Similarly, treating LMC strains with MYPY resulted in significant log reduction but higher concentration was required compared to LAPY. Treatment of LMC strains with 250 ppm of MYPY for 4, 6 and 10 min resulted in >4 log CFU/ml reduction. Both LAPY and MYPY demonstrated remarkable inhibitory activity against LMC strains compared to lauric acid which was previously reported to be active against Listeria and other gram-positive bacterial strains. However, treating LMC strains with pyrrolidine amide derivative of palmitic acid (PAPY) did not result in significant log reduction. To the best of our knowledge, this is the first study to demonstrate that pyrrolidine amide derivative of lauric and myristic acids have excellent inhibitory activity against LMC strains.