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Mass Spectrometric Analysis of Bioactive Metabolites from Lactobacilli Open Access


Other title
mass spectrometry
hydroxy fatty acid
Type of item
Degree grantor
University of Alberta
Author or creator
Black, Brenna A
Supervisor and department
Curtis, Jonathan (Agricultural, Food, and Nutritional Science)
Gänzle, Michael (Agricultural, Food, and Nutritional Science)
Examining committee member and department
Strelkov, Stephen (Agricultural, Food, and Nutritional Science)
Li, Xing-Fang (Laboratory Medicine and Pathology)
Gänzle, Michael (Agricultural, Food, and Nutritional Science)
Curtis, Jonathan (Agricultural, Food, and Nutritional Science)
Vogel, Rudi (Center of Life and Food Sciences Weihenstephan)
Department of Agricultural, Food, and Nutritional Science
Food Science and Technology
Date accepted
Graduation date
Doctor of Philosophy
Degree level
Lactobacilli are commonly used in food fermentations. Preservation and changes in food quality due to fermentation arise because of the growth, metabolism and enzymatic activity of these organisms. Enzymatic pathways of lactobacilli can also be exploited for the production of bioactive compounds. In this work, Lactobacillus spp. were used to enzymatically produce hydroxy fatty acids with anti-fungal activities and oligosaccharides with anti-adhesion properties. These bioactive compounds were found to be present as mixtures of geometric and positional isomers. In order to characterize individual isomers with minimal preparatory steps, liquid chromatography/tandem mass spectrometry (LC-MS/MS) methods were developed. Lactobacillus hammesii and Lactobacillus plantarum converted linoleic acid into a racemic mixture of anti-fungal 10-hydroxy-cis-12-octadecenoic and 10-hydroxy-trans-12-octadecenoic acid by means of hydratase enzymes. When produced in sourdough bread 10-hydroxy-12-octadecenoic acid and anti-fungal 13-hydroxy-cis-9,trans-11-octadecadienoic acid, the latter which is enzymatically formed by flour lipoxygenase in the presence of reducing agents, increased the mould-free storage-life of the bread. Results from LC-MS/MS methods allowed for conversion pathway elucidation of linoleic acid to conjugated linoleic acid by lactobacilli. Lactobacillus spp. containing galactosidase enzymes were used to form composite oligosaccharides with anti-adhesive properties. Using LC-MS/MS analysis, several novel oligosaccharides formed by β- and α-galactosidase were identified. In particular, Galβ-(1→4)-GlcNAc was formed, which is the core structure in human milk oligosaccharides and acts as a competative inhibitor to enteropathogenic Escherichia coli. The LC-MS/MS methods developed in this work proved useful in investigating structure-function relationships of anti-fungal lipids and anti-adhesive oliogsaccharides. This research can be further applied to increase the variety of bioactive compounds identified for food protection and health promotion.
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
Citation for previous publication
Black, B.A., Lee, V.S.Y., Zhao, Y.Y., Hu, Y., Curtis, J.M. and Gänzle, M.G. 2012. Structural identification of novel oligosaccharides produced by Lactobacillus bulgaricus and Lactobacillus plantarum. Journal of Agricultural and Food Chemistry, 60, 4886-4894.Black, B.A., Zannini, E., Curtis, J.M. and Gänzle, M.G. 2013. Antifungal hydroxy fatty acids produced during sourdough fermentation: microbial and enzymatic pathways, and antifungal activity in bread. Applied and Environmental Microbiology, 79, 1866-1873.Black, B.A., Sun, C., Zhao, Y.Y., Gänzle, M.G. and Curtis, J.M. 2013. Antifungal lipids produced by lactobacilli and their structural identification by normal phase LC/atmospheric pressure photoionization-MS/MS. Journal of Agricultural and Food Chemistry, 61, 5338-5346.Sun, C., Black, B.A., Zhao, Y.Y., Gänzle, M.G. and Curtis, J.M. 2013. Identification of conjugated linoleic acid isomers by silver ion - LC/in-line ozonolysis/MS. Analytical Chemistry, 85, 7345-7352.Wang, Y., Black, B.A., Curtis, J.M. and Gänzle, M.G. 2013. Characterization of α-galactooligosaccharides formed via heterologous expression of α-galactosidases from Lactobacillus reuteri in Lactococcus lactis. Applied Microbiology and Biotechnology, In press.

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