title: Antifungal lipids produced by lactobacilli and their structural identification by normal phase LC/atmospheric pressure photoionization−MS/MS.
abstract: Lactobacillus hammesii converts linoleic acid into an antifungal hydroxy fatty acid. High speed counter-current chromatography (HSCCC) using a hexane/ethyl acetate/methanol/water solvent system [3.5:1.5:3:2 (v/v/v/v)] allowed isolation of the antifungal hydroxy fatty acid. A method was developed for characterization of antifungal hydroxy fatty acids using normal phase liquid chromatography combined with atmospheric pressure photoionization-tandem mass spectrometry (LC/APPI-MS/MS). The position of unsaturations and hydroxyl groups was determined directly from crude lipid extracts and their hydroxylated derivatives. The antifungal compounds were identified as a racemic mixture of 10-hydroxy-cis-12-octadecenoic and 10-hydroxy-trans-12-octadecenoic acid. Additionally, HSCCC and LC/APPI-MS/MS methods were used to elucidate the pathway of conversion of linoleic acid by Lactobacillus sanfranciscensis , Lactobacillus plantarum , and L. hammesii to hydroxy fatty acids and conjugated linoleic acid. This study links previously reported 10-hydroxy-12-octadecenoic acid producing Lactobacillus strains to antifungal activities.
authors.affiliation: Department of Agricultural, Food and Nutritional Science, University of Alberta, 410 Agriculture/Forestry Centre, 3-60D South Academic Building, Edmonton, Alberta T6G 2P5, Canada.
authors.forename: Brenna A
authors.initials: BA
authors.lastname: Black
authors.forename: Chenxing
authors.initials: C
authors.lastname: Sun
authors.forename: Yuan Yuan
authors.initials: YY
authors.lastname: Zhao
authors.forename: Michael G
authors.initials: MG
authors.lastname: Gänzle
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: Curtis
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D001939:Bread / Q000382:microbiology; D002851:Chromatography, High Pressure Liquid; D003377:Countercurrent Distribution; D005285:Fermentation; D005520:Food Preservatives / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D006900:Hydroxylation; D007778:Lactobacillus / Q000378:metabolism*; D048191:Lactiplantibacillus plantarum / Q000378:metabolism; D015394:Molecular Structure; D009829:Oleic Acids / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification*; D055668:Photochemical Processes; D012277:Ricinoleic Acids / Q000378:metabolism; D013237:Stereoisomerism; D053719:Tandem Mass Spectrometry
chemical_list: D000935:Antifungal Agents; D005520:Food Preservatives; D009829:Oleic Acids; D012277:Ricinoleic Acids; C040430:10-hydroxy-12-octadecenoic acid; C030521:ricinoleic acid