{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,13]],"date-time":"2026-01-13T09:50:52Z","timestamp":1768297852246,"version":"3.49.0"},"reference-count":31,"publisher":"MDPI AG","issue":"20","license":[{"start":{"date-parts":[[2019,10,14]],"date-time":"2019-10-14T00:00:00Z","timestamp":1571011200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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%\u201379.49%. 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.<\/jats:p>","DOI":"10.3390\/molecules24203692","type":"journal-article","created":{"date-parts":[[2019,10,14]],"date-time":"2019-10-14T12:14:05Z","timestamp":1571055245000},"page":"3692","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":32,"title":["Antibacterial and Antifungal Activity of Three Monosaccharide Monomyristate Derivatives"],"prefix":"10.3390","volume":"24","author":[{"given":"Jumina","family":"Jumina","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281, Indonesia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mutmainah","family":"Mutmainah","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281, Indonesia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bambang","family":"Purwono","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281, Indonesia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4547-239X","authenticated-orcid":false,"given":"Yehezkiel Steven","family":"Kurniawan","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281, Indonesia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yana Maolana","family":"Syah","sequence":"additional","affiliation":[{"name":"Faculty of Mathematics and Natural Sciences, Institut Teknologi Bandung, Bandung 40132, Indonesia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,10,14]]},"reference":[{"key":"ref_1","first-page":"1","article-title":"Drug combinations: A strategy to extend the life of antibiotics in the 21st century","volume":"7","author":"Tyers","year":"2019","journal-title":"Nature Rev. Microbiol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1038\/nrd.2017.46","article-title":"The antifungal pipeline: A reality check","volume":"16","author":"Perfect","year":"2017","journal-title":"Nature Rev. Drug Discov."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"174","DOI":"10.1177\/003335490512000211","article-title":"Escherichia coli O157:H7 outbreak associated with consumption of ground beef","volume":"120","author":"Vogt","year":"2005","journal-title":"Public Health Rep."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1128\/CMR.00134-14","article-title":"Staphylococcus aureus infections: Epidemiology, pathophysiology, clinical manifestations, and management","volume":"28","author":"Tong","year":"2015","journal-title":"Clin. Microbiol. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1038\/nrmicro.2016.157","article-title":"Candida albicans cell-type switching and functional plasticity in the mammalian host","volume":"15","author":"Noble","year":"2017","journal-title":"Nat. Rev. Microbiol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"8661","DOI":"10.3390\/molecules17078661","article-title":"Synthesis, characterization, antibacterial and antifungal evaluation of novel monosaccharide esters","volume":"17","author":"Shen","year":"2012","journal-title":"Molecules"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Hong, J., Zeng, X.A., Brennan, C.S., Brennan, M., and Han, Z. (2016). Recent advances in techniques for starch esters and the appications: A review. Foods, 5.","DOI":"10.3390\/foods5030050"},{"key":"ref_8","first-page":"1","article-title":"Lactose esters: Synthesis and biotechnological applications","volume":"38","author":"Staro","year":"2018","journal-title":"Crit. Rev. Biotechnol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"595","DOI":"10.1080\/10408398.2012.667461","article-title":"Sugar ester surfactants: Enzymatic synthesis and applications in food industry","volume":"55","author":"Neta","year":"2015","journal-title":"Crit. Rev. Food. Sci."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"4803","DOI":"10.1016\/j.bmc.2011.06.078","article-title":"Synthesis, gp120 binding and anti-HIV activity of fatty acid esters of 1,1-linked disaccharides","volume":"19","author":"Bachan","year":"2011","journal-title":"Bioorg. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1016\/j.lwt.2014.07.050","article-title":"High intensity ultrasound assisted heating to improve solubility, antioxidant and antibacterial properties of chitosan-fructose Maillard reaction products","volume":"60","author":"Zhang","year":"2015","journal-title":"LWT Food Sci. Technol."},{"key":"ref_12","unstructured":"Ahmad, M.U. (2017). Synthesis of sugar fatty acid ester and their industrial utilizations. Fatty Acids, Elsevier."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"2557","DOI":"10.1016\/j.carres.2008.07.012","article-title":"Synthesis and antimicrobial evaluation of carbohydrate and polyhydroxylated non-carbohydrate fatty acid ester and ether derivatives","volume":"343","author":"Smith","year":"2008","journal-title":"Carbohydr. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/j.ejpb.2016.06.022","article-title":"Unsaturated fatty acids lactose esters: Cytotoxicity, permeability enhancement and antimicrobial activity","volume":"107","author":"Lucarini","year":"2016","journal-title":"Eur. J. Pharm. Biopharm."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.ijadhadh.2018.09.009","article-title":"Methacrylate saccharide-based monomers for dental adhesive systems","volume":"87","author":"Andre","year":"2018","journal-title":"Int. J. Adhes. Adhes."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"7081","DOI":"10.1021\/jf4017509","article-title":"NF-KB inhibitory activity of sucrose fatty acid esters and related constituents from Astragalus membranaceus","volume":"61","author":"Li","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"508","DOI":"10.1016\/j.foodchem.2018.06.051","article-title":"Synthesis and characterization of lactose fatty acid ester biosurfactants using free and immobilized lipases in organic solvents","volume":"266","author":"Enayati","year":"2018","journal-title":"Food Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"765","DOI":"10.1016\/j.bmc.2017.12.038","article-title":"One step synthesis of carbohydrate esters as antibacterial and antifungal agent","volume":"26","author":"Alfindee","year":"2018","journal-title":"Bioorg. Med. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"17339","DOI":"10.3390\/molecules200917339","article-title":"Biological and nutritional properties of palm oil and palmitic acid: Effects on health","volume":"20","author":"Mancini","year":"2015","journal-title":"Molecules"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"135","DOI":"10.4028\/www.scientific.net\/MSF.901.135","article-title":"New lubricant from used cooking oil: Cyclic ketal of ethyl 9,10-dihydroxyoctadecanoate","volume":"901","author":"Kurniawan","year":"2017","journal-title":"Mater. Sci. Forum"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2289","DOI":"10.1007\/s13197-012-0677-0","article-title":"Essential fatty acids as functional components of foods- a review","volume":"51","author":"Kaur","year":"2014","journal-title":"J. Food Sci. Technol."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Torres, J.D.J.M., Franco, J.A.S., Moreno, E.R., Cansino, N.D.S.C., Ortega, J.A.A., and Valencia, J.M.T. (2016). Effect on thermoultrasound on the antioxidant compounds and fatty acid profile of blackberry (Rubus fructicosus spp.) juice. Molecules, 21.","DOI":"10.3390\/molecules21121624"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"e00861","DOI":"10.1016\/j.heliyon.2018.e00861","article-title":"Chemical synthesis and cytotoxicity of neo-glycolipids; rare sugar-glycerol-lipid compounds","volume":"4","author":"Hirata","year":"2018","journal-title":"Heliyon"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Nurmala, A., Fitria, A., Pranowo, D., Sholikhah, E.N., Kurniawan, Y.S., and Kuswandi, B. (2018). Monomyristin and monopalmitin derivatives: Synthesis and evaluation as potential antibacterial and antifungal agents. Molecules, 23.","DOI":"10.3390\/molecules23123141"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"63","DOI":"10.4028\/www.scientific.net\/MSF.948.63","article-title":"Chemical synthesis of monosaccharide lauric acid esters as antibacterial and antifungal agents","volume":"948","author":"Mutmainah","year":"2019","journal-title":"Mater. Sci. Forum"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"9","DOI":"10.3109\/10242429409034373","article-title":"Facile chemo-enzymatic synthesis of monosaccharide fatty acid esters","volume":"11","author":"Fregapane","year":"1994","journal-title":"Biocatalysis"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3817","DOI":"10.1016\/S0040-4020(01)80906-6","article-title":"Sugar chemistry without protecting groups-III. A facile chemical synthesis of 6-O-acyl-D-glycopyranoses and methyl-6-O-acyl-d-glycopyranosides","volume":"47","author":"Baczko","year":"1991","journal-title":"Tetrahedron"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"370","DOI":"10.1016\/j.foodchem.2015.04.108","article-title":"In vitro antibacterial activities and mechanism of sugar fatty acid esters against five food-related bacteria","volume":"187","author":"Zhao","year":"2015","journal-title":"Food Chem."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Yoon, B.K., Jackman, J.A., Valle-Gonzalez, E.R., and Cho, N.J. (2018). Antibacterial free fatty acids and monoglycerides: Biological activities, experimental testing, and therapeutic applications. Int. J. Mol. Sci., 19.","DOI":"10.3390\/ijms19041114"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"10941","DOI":"10.1038\/s41598-019-47373-4","article-title":"Preparation of monoacylglycerol derivatives from Indonesian edible oil and their antimicrobial assay against Staphylococcus aureus and Escherichia coli","volume":"9","author":"Jumina","year":"2019","journal-title":"Sci. Rep."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"272","DOI":"10.1016\/S0966-842X(03)00117-3","article-title":"Antifungal agents: Mechanism of action","volume":"6","author":"Odds","year":"2003","journal-title":"Trends Microbiol."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/20\/3692\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T13:26:10Z","timestamp":1760189170000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/20\/3692"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,10,14]]},"references-count":31,"journal-issue":{"issue":"20","published-online":{"date-parts":[[2019,10]]}},"alternative-id":["molecules24203692"],"URL":"https:\/\/doi.org\/10.3390\/molecules24203692","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,10,14]]}}}