Antimicrobial properties of 1‐monoacylglycerols prepared from undecanoic (C11:0) and undecenoic (C11:1) acid

Abstract

Antimicrobial activity of monoacylglycerols (MAG) with odd number of carbons prepared from undecanoic (MAG C11:0) and undecenoic (MAG C11:1) was investigated. Data showed that both studied substances successfully inhibited Gram-positive cocci (Staphylococcus aureus) and spore-forming rods (Bacillus cereus). Gram-negative bacteria were highly resistant against MAG C11:0 and showed considerable tolerance against MAG C11:1. Minimum inhibitory concentration (MIC) of MAG C11:1 was possible to determine for Escherichia coli only. Complete inhibition of three fungi genera (Alternaria, Cladosporium, Trichothecium) was achieved using MAG C11:1 with a concentration higher than 750 mg/ mL. The growth of Aspergillus niger, Mucor racemosus, Phoma, Scopulariopsis, Trichoderma was significantly reduced. Generally, MAG C11:1 was more efficient than MAG C11:0 against all tested microorganisms. Due to a rich production of degradation enzymes, some fungi species surprisingly adapted their metabolism during growth and were even able to utilise tested MAG as a source of carbon.Practical applications: MAG composed of fatty acids with odd number of carbons in molecule are a promising group of substances applicable in food industry and cosmetics. They represent materials with broad spectrum of antimicrobial activity, especially against Gram-positive bacteria. More efficient MAG C11:1 with a double bond in molecule can be recommended for reduction of S. aureus that cause food enterotoxicosis.

Synthesis, characterization and evaluation of 1-monoacylglycerols of unsaturated fatty acids as potential bioactive lipids

“…In this study, the MAG of undecenoic acid was found to be active against two Gram-positive and one Gram-negative bacterial strains. The MIC value of UDA-MAG against Staphylococcus aureus in the present study was 150 µg/mL, which was comparable to the value determined in a previously reported study (Dolezalova et al, 2010). It was reported that undecenoic acid was better known for its antifungal activity rather than antibacterial activity (Marijke and Stevens 2009).…”

Synthesis, characterization and evaluation of 1-monoacylglycerols of unsaturated fatty acids as potential bioactive lipids

“…In this study, the MAG of undecenoic acid was found to be active against two Gram-positive and one Gram-negative bacterial strains. The MIC value of UDA-MAG against Staphylococcus aureus in the present study was 150 µg/mL, which was comparable to the value determined in a previously reported study (Dolezalova et al, 2010). It was reported that undecenoic acid was better known for its antifungal activity rather than antibacterial activity (Marijke and Stevens 2009).…”

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

“…10-Undecenoic acid was chosen as the lipid part as the derivatives of undecenoic acid have been reported to be potent bioactive compounds [12–13]. Additionally the terminal double bond of undecenoic acid provides a reactive group for further derivatization for producing potential functional derivatives.…”

Age matters: Microbiome depletion prior to repeat mild traumatic brain injury differentially alters microbial composition and function in adolescent and adult rats

“…We also identified a higher abundance of isoleucylproline and monoacylglycerols in microbiome depleted adolescent rats. Interestingly, monoacylglycerols have been associated with anti-microbial properties [ 67 , 68 ] and may be a compensatory action to reduce the abundance of opportunistic bacteria. A reduction in O-desmethylangolensin (O-DMA), a bacterial metabolite involved in the breakdown of certain soy containing foods [ 69 ], was reduced in adolescents compared to adult rats at day 30.…”

Synthesis, characterization and evaluation of 1-monoacylglycerols of unsaturated fatty acids as potential bioactive lipids

“…In this study, the MAG of undecenoic acid was found to be active against two Gram-positive and one Gram-negative bacterial strains. The MIC value of UDA-MAG against Staphylococcus aureus in the present study was 150 µg/mL, which was comparable to the value determined in a previously reported study (Dolezalova et al, 2010). It was reported that undecenoic acid was better known for its antifungal activity rather than antibacterial activity (Marijke and Stevens 2009).…”

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

“…10-Undecenoic acid was chosen as the lipid part as the derivatives of undecenoic acid have been reported to be potent bioactive compounds [12–13]. Additionally the terminal double bond of undecenoic acid provides a reactive group for further derivatization for producing potential functional derivatives.…”

Age matters: Microbiome depletion prior to repeat mild traumatic brain injury differentially alters microbial composition and function in adolescent and adult rats

“…We also identified a higher abundance of isoleucylproline and monoacylglycerols in microbiome depleted adolescent rats. Interestingly, monoacylglycerols have been associated with anti-microbial properties [ 67 , 68 ] and may be a compensatory action to reduce the abundance of opportunistic bacteria. A reduction in O-desmethylangolensin (O-DMA), a bacterial metabolite involved in the breakdown of certain soy containing foods [ 69 ], was reduced in adolescents compared to adult rats at day 30.…”

Synthesis, characterization and evaluation of 1-monoacylglycerols of unsaturated fatty acids as potential bioactive lipids

“…In this study, the MAG of undecenoic acid was found to be active against two Gram-positive and one Gram-negative bacterial strains. The MIC value of UDA-MAG against Staphylococcus aureus in the present study was 150 µg/mL, which was comparable to the value determined in a previously reported study (Dolezalova et al, 2010). It was reported that undecenoic acid was better known for its antifungal activity rather than antibacterial activity (Marijke and Stevens 2009).…”

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

“…10-Undecenoic acid was chosen as the lipid part as the derivatives of undecenoic acid have been reported to be potent bioactive compounds [12–13]. Additionally the terminal double bond of undecenoic acid provides a reactive group for further derivatization for producing potential functional derivatives.…”

Age matters: Microbiome depletion prior to repeat mild traumatic brain injury differentially alters microbial composition and function in adolescent and adult rats

“…We also identified a higher abundance of isoleucylproline and monoacylglycerols in microbiome depleted adolescent rats. Interestingly, monoacylglycerols have been associated with anti-microbial properties [ 67 , 68 ] and may be a compensatory action to reduce the abundance of opportunistic bacteria. A reduction in O-desmethylangolensin (O-DMA), a bacterial metabolite involved in the breakdown of certain soy containing foods [ 69 ], was reduced in adolescents compared to adult rats at day 30.…”