Antibacterial and Antifungal Activity of Three Monosaccharide Monomyristate Derivatives

Abstract

Microbial infections remains a serious challenge in food industries due to their resistance to some of the well-known antibacterial and antifungal agents. In this work, a novel monomyristoyl ester (fructosyl monomyristate) and two other derivatives (i.e., glucosyl and galactosyl monomyristates) were successfully synthesized from myristic acid and monosaccharides in two-step reactions. First, the myristic acid was converted to myristoyl chloride, and then the myristoyl chloride was reacted with fructose, glucose and galactose separately to produce the corresponding monosaccharide monomyristate derivatives. The structures of the synthesized products were confirmed by Fourier transform infrared (FTIR), proton and carbon nuclear magnetic resonance (1H- and 13C-NMR), and mass spectral (MS) data. The monomyristates esters were obtained in reaction yields of 45.80%–79.49%. The esters were then evaluated for their antimicrobial activity using the disc diffusion test. It was found that the esters exhibited a medium antibacterial activity against gram-positive bacteria; however, they showed a weak antibacterial activity against gram-negative bacteria. Amongst the esters, galactosyl myristate yielded the highest antibacterial activity against Salmonella typhimurium, Staphylococcus aureus and Bacillus subtilis, while glucosyl monomyristate exhibited the highest antibacterial activity only against Escherichia coli. Additionally, all products showed remarkable antifungal activity against Candida albicans. These findings demonstrate that monosaccharide monomyristate derivatives are promising for use as biocompatible antimicrobial agents in the future.

Lactobacillus crispatus BC1 Biosurfactant Counteracts the Infectivity of Chlamydia trachomatis Elementary Bodies

“…Conversely, the functionality of medium- and long-chain fatty acids on the microbial cells has been only partially explored. Medium- and long-chain free fatty acids have been found to have a broad spectrum of microbicidal in vitro activity against various bacteria, including some pathogens responsible for urogenital and sexually transmitted infections [ 31 , 32 , 33 , 34 , 35 , 36 ]. However, their antimicrobial effects varied greatly depending not only on fatty acid concentration and structure (length of fatty acid chain and type of derivatives), but also on the microorganism and bacterial species tested.…”

Nutritional Composition of Apis mellifera Drones from Korea and Denmark as a Potential Sustainable Alternative Food Source: Comparison Between Developmental Stages

“…Vitamin C (Sigma Co., St. Louis, MO, USA) was used as a positive control. [39]. A volume of 100 µL of each preculture was spread on agar plates; filter paper (Whatman No.2) soaked with 5 µL of bee extracts was loaded on the agar plate.…”

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

“…Finally, although some of the sugar-based esters here presented have already been published for other applications and also as possible antibacterial agents [22][23][24][29][30][31][32][33], a detailed comparative study concerning the properties of a relative large number of both aliphatic and aromatic amphiphilic carbohydrate esters as antimicrobial (Gram-positive, Gram-negative, and fungi) and mostly antibiofilm agents is still lacking.…”