Monomyristin and Monopalmitin Derivatives: Synthesis and Evaluation as Potential Antibacterial and Antifungal Agents

Abstract

In the present work, monoacylglycerol derivatives, i.e., 1-monomyristin, 2-monomyristin, and 2-monopalmitin were successfully prepared from commercially available myristic acid and palmitic acid. The 1-monomyristin compound was prepared through a transesterification reaction between ethyl myristate and 1,2-O-isopropylidene glycerol, which was obtained from the protection of glycerol with acetone, then followed by deprotection using Amberlyst-15. On the other hand, 2-monoacylglycerol derivatives were prepared through enzymatic hydrolysis of triglycerides in the presence of Thermomyces lanuginosa lipase enzymes. The synthesized products were analyzed using fourier transform infrared (FTIR) spectrophotometer, gas or liquid chromatography-mass spectrometer (GC-MS or LC-MS), and proton and carbon nuclear magnetic resonance (1H- and 13C-NMR) spectrometers. It was found that monomyristin showed high antibacterial and antifungal activities, while 2-monopalmitin did not show any activity at all. The 1-monomyristin compound showed higher antibacterial activity against Staphylococcus aureus and Aggregatibacter actinomycetemcomitans and also higher antifungal activity against Candida albicans compared to the positive control. Meanwhile, 2-monomyristin showed high antibacterial activity against Escherichia coli. The effect of the acyl position and carbon chains towards antibacterial and antifungal activities was discussed.

Preparation of Monoacylglycerol Derivatives from Indonesian Edible Oil and Their Antimicrobial Assay against Staphylococcus aureus and Escherichia coli

“…The other chemicals such as urea, potassium hydroxide, sulfuric acid, Amberlyst-15 and Thermomyces Lanuginosa as Lipase enzyme were purchased in pro analytic grade and used without further purification. The synthesis of 1,2- O -isopropylidene glycerol has been carried out in a similar procedure to the previously described 25 .…”

“…The antimicrobial assay of the synthesized products was carried out at Microbiology Laboratory of Faculty of Veterinary Medicine, Universitas Gadjah Mada by using a well-diffusion method as previously reported 25,27 . S. aureus FNCC 0047 was used as a representative of gram-positive bacteria while E. coli FNCC 0091 was used as a representative of gram-negative bacteria.…”

Antibacterial and Antifungal Activity of Three Monosaccharide Monomyristate Derivatives

“…The antibacterial and antifungal activity assays were conducted to evaluate the biological activity of the synthesized product according to the method that has been previously described [24]. The bacteria used were S. aureus and B. subtilis for the gram-positive bacteria, and S. typhimurium and E. coli for the gram-negative bacteria, while C. albicans was selected for antifungal assay.…”

“…In our previous study, monomyristin derivatives of sugars show higher antibacterial activities against S. aureus , E. coli , B. subtilis and Aggregatibacter actinomycetemcomitans ( A. actinomycetemcomitans ). It was found that a 1-monomyristin derivative exhibits higher antifungal activity against C. albicans than a monopalmitin derivative [24]. Furthermore, the lauric esters of monosaccharide also exhibited medium antifungal and antibacterial activity against gram-positive bacteria [25].…”

Spectroscopy Study of Honey Pineapple Peels Extracted in Different Solvents

“…As Indonesia has 10% of world plant species in 90 ecosystems [3], Indonesia becomes the second largest mega biodiversity country in the world. Because of these abundant natural resources, researches on the isolation and application of tropical plants and fruits have gained a lot of interest [4][5][6].…”