Comparative study of surface-active properties and antimicrobial activities of disaccharide monoesters.

Xi Zhang,Fei Song,Maierhaba Taxipalati,Wei Wei,Fengqin Feng,Chien-Sheng Chen

doi:10.1371/journal.pone.0114845

Xi Zhang, Fei Song + Show 4 more

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https://doi.org/10.1371/journal.pone.0114845

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Abstract

The objective of this research was to determine the effect of sugar or fatty acid in sugar ester compounds on the surface-active properties and antimicrobial activities of these compounds. Disaccharides of medium-chain fatty acid monoesters were synthesized through transesterifications by immobilized lipase (Lipozyme TLIM) to yield nine monoesters for subsequent study. Their antimicrobial activities were investigated using three pathogenic microorganisms: Staphylococcus aureus, Escherichia coli O157:H7 and Candida albicans. Their surface-active properties including air–water surface tension, critical micelle concentration, and foaming and emulsion power and stability were also studied. The results showed that all of the tested monoesters were more effective against Staphylococcus aureus (Gram-positive bacterium) than against Escherichia coli O157:H7 (Gram-negative bacterium). The results demonstrated that the carbon chain length was the most important factor influencing the surface properties, whereas degree of esterification and hydrophilic groups showed little effect.

Highlights

Fatty acid sugar esters are receiving increasing attention as odorless, nontoxic and biodegradable nonionic surfactants, which are mild to the skin
The formed vinyl alcohol tautomerized to a low-boiling-point acetaldehyde, which was conducive to the transesterification
The purity of each monoester was higher than 90% after refining with liquidliquid extraction and column chromatography, and the side-products were diesters

Summary

Introduction

Fatty acid sugar esters are receiving increasing attention as odorless, nontoxic and biodegradable nonionic surfactants, which are mild to the skin. Sucrose fatty acid esters have certification of GRAS FDA 21CFR 172.859, and could be used as food additives. They are interested by the food industry because they possess many attractive properties, such as emulsification, emulsion stabilization, foaming. Comparative Study of Disaccharides Monoesters example, sugar esters include a wide range of hydrophilic–lipophilic balance (HLB) values from 1 to 16 achieved with different degrees of esterification, and these esters are commonly employed in the food industry as emulsifying agents [1,2,3]. Habulin et al have reported that sucrose monolaurate could inhibit Bacillus cereus at concentration of 9.375 mg/mL. Habulin et al have reported that sucrose monolaurate could inhibit Bacillus cereus at concentration of 9.375 mg/mL. [6] Ferrer et al measured the effects of lauroylsucrose and lauroylmaltose against Bacillus sp. and Escherichia coli. [7] Surfactants may influence cell membranes at low concentration, which could lead to change the permeability of cell membrane, [8] with subsequent metabolic inhibition, growth arrest or cell lysis [9]

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