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Molecules 2018, 23(5), 1118; https://doi.org/10.3390/molecules23051118

Lipase-Catalyzed Synthesis of Sucrose Monolaurate and Its Antibacterial Property and Mode of Action against Four Pathogenic Bacteria

1
Zhejiang Provincial Collaborative Innovation Center of Food Safety and Nutrition, Zhejiang Gongshang University, Hangzhou 310035, China
2
School of Food Science and Biotechnology, Zhejiang Gongshang University, Hangzhou 310035, China
*
Author to whom correspondence should be addressed.
Received: 26 April 2018 / Revised: 4 May 2018 / Accepted: 7 May 2018 / Published: 8 May 2018
(This article belongs to the Special Issue Ionic Liquids for Chemical and Biochemical Applications)
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Abstract

The aim of this work was to evaluate the antibacterial activities and mode of action of sucrose monolaurate (SML) with a desirable purity, synthesized by Lipozyme TL IM-mediated transesterification in the novel ionic liquid, against four pathogenic bacteria including L. monocytogenes, B. subtilis, S. aureus, and E. coli. The antibacterial activity was determined by minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and the time–kill assay. SML showed varying antibacterial activity against tested bacteria with MICs and MBCs of 2.5 and 20 mM for L. monocytogenes, 2.5 and 20 mM for B. subtilis, 10 and 40 mM for S. aureus, respectively. No dramatic inhibition was observed for E. coli at 80 mM SML. Mechanism of bacterial inactivation caused by SML was revealed through comprehensive factors including cell morphology, cellular lysis, membrane permeability, K+ leakage, zeta potential, intracellular enzyme, and DNA assay. Results demonstrated that bacterial inactivation against Gram-positive bacteria was primarily induced by the pronounced damage to the cell membrane integrity. SML may interact with cytoplasmic membrane to disturb the regulation system of peptidoglycan hydrolase activities to degrade the peptidoglycan layer and form a hole in the layer. Then, the inside cytoplasmic membrane was blown out due to turgor pressure and the cytoplasmic materials inside leaked out. Leakage of intracellular enzyme to the supernatants implied that the cell membrane permeability was compromised. Consequently, the release of K+ from the cytosol lead to the alterations of the zeta potential of cells, which would disturb the subcellular localization of some proteins, and thereby causing bacterial inactivation. Moreover, remarkable interaction with DNA was also observed. SML at sub-MIC inhibited biofilm formation by these bacteria. View Full-Text
Keywords: ionic liquids; lipase; biocatalysis; sucrose monolaurate; antimicrobial activity; biofilm ionic liquids; lipase; biocatalysis; sucrose monolaurate; antimicrobial activity; biofilm
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Shao, S.-Y.; Shi, Y.-G.; Wu, Y.; Bian, L.-Q.; Zhu, Y.-J.; Huang, X.-Y.; Pan, Y.; Zeng, L.-Y.; Zhang, R.-R. Lipase-Catalyzed Synthesis of Sucrose Monolaurate and Its Antibacterial Property and Mode of Action against Four Pathogenic Bacteria. Molecules 2018, 23, 1118.

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