Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties

Abstract

The lipases from Thermomyces lanuginosus (immobilized by granulation with silica) and Candida antarctica B (adsorbed on Lewatit, "Novozym 435") were comparatively assayed for the synthesis of sugar esters by transesterification of sugars with fatty acid vinyl esters in 2-methyl-2-butanol:dimethylsulfoxide mixtures. We found that lipase from C. antarctica B is particularly useful for the preparation of 6,6'-diacylsucrose, whereas T. lanuginosus lipase catalyzes selectively the synthesis of 6-Oacylsucrose. The granulated T. lanuginosus lipase retained more than 80% of its initial activity after 20 cyles of 6 hours. Both lipases were similarly effective for the regioselective synthesis of 6'-O-palmitoylmaltose and 6-O-lauroylglucose. The effect of the synthesized sugar esters on the growth in liquid medium of various microorganisms (Gram-positive, Gram-negative and yeasts) was evaluated. 6-Olauroylsucrose and 6'-O-lauroylmaltose inhibited the growth of Bacillus sp. at a concentration of 0.8 mg/ml, and of Lactobacillus plantarum at 4 mg/ml. Sucrose dilaurates and 6-O-lauroylglucose did not show antimicrobial activity, probably due to their low aqueous solubility. As regards the inhibition of yeasts, none of the tested carbohydrate esters inhibited significantly the growth of Zygosaccharomyces rouxii and Pichia jadinii.

Boosting TiO2-anatase antimicrobial activity: Polymer-oxide thin films

“…To study the antimicrobial activity of the films, a suspension containing 10 ml of microbial cells (ca. 10 9 cfu ml À1 ) suspended in 1 ml broth solution was made as described elsewhere [13]. Aliquots of 1 ml from these suspensions were added to a 4 ml quartz cubic cell containing 1 ml of sterilized water and the corresponding film under continuous stirring.…”

Lipase catalyzed ester synthesis for food processing industries

“…Maltose esters, thus synthesized could be used as alternative food emulsifiers because in addition to surfactant properties, they exhibited antimicrobial properties comparable to sucrose esters. Most sugar fatty acid esters display significant activity against several food and clinical isolates (Ferrer et al, 2005). Natural methylthioesters of short-chain fatty acids (C 3 -C 8 ) are of great interest in the flavour industry.…”

“…Sucrose fatty acid esters are used as the non-ionic surfactants in the food processing and some other acylated carbohydrates are employed as the pharmaceuticals with the antimicrobial, antitumoural and/or antibiotic activity. Silica granulated T. lanuginosa lipase served as feasible biocatalyst for the synthesis of acylsucroses or other carbohydrates esters in the polar or slightly polar solvents (Ferrer et al, 2001;Ferrer et al, 2005). Lipases from T. lanuginosus and C. antarctica B were compared in terms of activity, regioselectivity and potentially reliable catalysts for sugar ester production.…”

Antimicrobial effects of fatty acid fructose esters

“…Sugar fatty acid esters, synthesised from renewable resources such as fatty acids and carbohydrates, are biodegradable and have broad applications in the food industry. Other fields of application include cosmetics, detergents, oral-care products, and medical supplies (Ferrer et al 2005).…”