Synthesis and antimicrobial evaluation of carbohydrate and polyhydroxylated non-carbohydrate fatty acid ester and ether derivatives

Smith, Aoife; Nobmann, Patricia; Henehan, Gary; Bourke, Paula; Dunne, Julie

doi:10.1016/j.carres.2008.07.012

Cited by 55 publications

(60 citation statements)

References 29 publications

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“…The inhibitory activity of sugar esters is dependent on the sugar, the number and type of fatty acids esterified, and the degree of esterification. Smith et al (11) synthesized various carbohydrate esters and found that the carbohydrate moiety can markedly influence the microbial inhibitory activity of the fatty acid. The activity of sugar esters has been suggested to be antimicrobial (2), while others have suggested they have just bacteriostatic activity (10).…”

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confidence: 99%

Effect of Lactose Monolaurate on Pathogenic and Nonpathogenic Bacteria

Wagh

Shen

et al. 2012

Appl Environ Microbiol

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confidence: 99%

Effect of Lactose Monolaurate on Pathogenic and Nonpathogenic Bacteria

Wagh

Shen

et al. 2012

Appl Environ Microbiol

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“…These biodegradable nonionic surfactants can also be applied as emulsifiers for foodstuff, personal care products, and medical supplies (Fietcher 1992;Yan et al 1999;Godshall 2001;Polat and Linhardt 2001). Antibacterial effects of fatty acids and their derivatives were observed in connection with Listeria monocytogenes (Monk et al 1996;Nobmann et al 2009), Staphylococcus aureus (Monk et al 1996;Nobmann et al 2010), Bacillus cereus , Escherichia coli (Smith et al 2008;Karlova et al 2010), and various food spoilage microorganisms (Yang et al 2003;Nobmann et al 2009;Polakova et al 2010). Contrary to the evaluation of the effect of free fatty acids or their monoglycerides studied extensively in the past (anticlostridial effect observed for example by Timbermont et al 2010), no study on the effect of sucrose monolaurate on Clostridium perfringens has been conducted.…”

Section: Introductionmentioning

confidence: 99%

“…Microorganisms differ in their susceptibility to carbohydrate fatty acid derivatives, and Grampositive bacteria were found to be more susceptible than Gram-negatives (Smith et al 2008;Nobmann et al 2009;Karlova et al 2010). The antimicrobial activity of carbohydrate fatty acid derivatives depends on both the carbohydrate moiety (Smith et al 2008;Nobmann et al 2009) and the carbon chain length (Smith et al 2008;Polakova et al 2010).…”

Section: Introductionmentioning

confidence: 99%

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Susceptibility of Escherichia coli and Clostridium perfringens to sucrose monoesters of capric and lauric acid

Skřivanová¹,

Pražáková²,

Benada³

et al. 2014

CZECH J ANIM SCI

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ABSTRACT:The sucrose monoesters of capric and lauric acid were tested for their antibacterial activity towards two foodborne enteropathogenic bacteria -Escherichia coli (CCM 3954 -serotype O6 and E22 -serotype O103) and Clostridium perfringens (CNCTC 5459 and CIP 105178). Antibacterial activity was evaluated by the plating technique. Sucrose monocaprate significantly decreased the number of viable cells of E. coli at all tested concentrations (0.1-5 mg/ml). The overnight incubation of C. perfringens with the sucrose ester of lauric acid at 0.1-5 mg/ml reduced the number of viable cells below the detection limit (2 log 10 CFU/ml). Incubating E. coli CCM 3954 and C. perfringens CNCTC 5459 with monoesters (0.1 and 2 mg/ml) did not influence the K + permeability of the cytoplasmic membrane in cells during a 2.5-minute treatment. A 30-minute incubation of E. coli CCM 3954 and C. perfringens CNCTC 5459 with esters (0.1 and 2 mg/ml) revealed damage to cytoplasmic structures, as observed by transmission electron microscopy.

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“…[18] [19] Glycosidic conjugation also leads to better absorption [20] and penetration of drugs into the cell membranes, thus aiding delivery of drugs to the targeted site. [24] For instance, galactose and fructose laurates have demonstrated excellent antibacterial effects against both Gram-positive and Gram-negative bacteria when compared with alternative analogues of synthesized fatty acid-carbohydrate esters. [22] The ibuprofen-fructose ester showed extended stability in aqueous solution, and fewer adverse effects, enhanced tissue uptake in comparison with ibuprofen alone.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in vitro Bioactivity Evaluation of New Galactose and Fructose Ester Derivatives of 5‐Aminosalicylic Acid

Yousefi

Bayat

Rahman

et al. 2017

Chemistry & Biodiversity

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Inflammatory bowel disease (IBD) is the main risk factor for developing colorectal cancer which is common in patients of all ages. 5-Aminosalicylic acid (5-ASA), structurally related to the salicylates, is highly active in the treatment of IBD with minor side effects. In this study, the synthesis of galactose and fructose esters of 5-ASA was planned to evaluate the role of glycoconjugation on the bioactivity of the parent drug. The antibacterial activity of the new compounds were evaluated against two Gram-negative and two Gram-positive species of bacteria, with a notable effect observed against Staphylococcus aureus and Escherichia coli in comparisons with the 5-ASA. Cytotoxicity testing over HT-29 and 3T3 cell lines indicated that the toxicity of the new products against normal cells was significantly reduced compared with the original drug, whereas their activity against cancerous cells was slightly decreased. The anti-inflammatory activity test in RAW264.7 macrophage cells indicated that the inhibition of nitric oxide by both of the monosaccharide conjugated derivatives was slightly improved in comparison with the non-conjugated drug.

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Synthesis and antimicrobial evaluation of carbohydrate and polyhydroxylated non-carbohydrate fatty acid ester and ether derivatives

Cited by 55 publications

References 29 publications

Effect of Lactose Monolaurate on Pathogenic and Nonpathogenic Bacteria

Effect of Lactose Monolaurate on Pathogenic and Nonpathogenic Bacteria

Susceptibility of Escherichia coli and Clostridium perfringens to sucrose monoesters of capric and lauric acid

Synthesis and in vitro Bioactivity Evaluation of New Galactose and Fructose Ester Derivatives of 5‐Aminosalicylic Acid

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