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Antibacterial and Antifungal Activity of Three Monosaccharide Monomyristate Derivatives
Jumina Jumina1, Mutmainah Mutmainah2, Bambang Purwono3
1Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281, Indonesia. jumina@ugm.ac.id.
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.
Insights
Novel monomyristoyl esters synthesized from myristic acid and monosaccharides show promising antimicrobial activity. These biocompatible derivatives offer potential as natural agents against foodborne microbial infections.
Area of Science:
- Food Science
- Organic Chemistry
- Microbiology
Background:
- Microbial infections pose significant challenges in the food industry due to antimicrobial resistance.
- Existing antibacterial and antifungal agents face limitations in efficacy and safety.
Purpose of the Study:
- To synthesize novel monomyristoyl esters from myristic acid and monosaccharides.
- To evaluate the antimicrobial and antifungal activities of these synthesized esters.
Main Methods:
- Two-step synthesis involving myristoyl chloride formation and reaction with fructose, glucose, and galactose.
- Structural confirmation using Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR), and mass spectrometry (MS).
- Antimicrobial activity assessed via disc diffusion tests against gram-positive and gram-negative bacteria and fungi.
Main Results:
- Successfully synthesized fructosyl, glucosyl, and galactosyl monomyristates with yields ranging from 45.80% to 79.49%.
- Esters demonstrated moderate antibacterial activity against gram-positive bacteria and weak activity against gram-negative bacteria.
- Significant antifungal activity was observed against Candida albicans; galactosyl monomyristate showed broad-spectrum antibacterial action.
Conclusions:
- Monosaccharide monomyristate derivatives are effective antimicrobial agents.
- These compounds show potential as biocompatible alternatives for controlling microbial contamination in food.
- Further research into these novel esters could lead to new food preservation strategies.
