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Characterization of Triacylglycerol Estolide Isomers Using High-Resolution Tandem Mass Spectrometry with Nanoelectrospray Ionization

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    0570636 - ÚOCHB 2024 RIV CH eng J - Journal Article
    Cudlman, Lukáš - Machara, Aleš - Vrkoslav, Vladimír - Polášek, Miroslav - Bosáková, Z. - Blanksby, S. J. - Cvačka, Josef
    Characterization of Triacylglycerol Estolide Isomers Using High-Resolution Tandem Mass Spectrometry with Nanoelectrospray Ionization.
    Biomolecules. Roč. 13, č. 3 (2023), č. článku 475. E-ISSN 2218-273X
    R&D Projects: GA MŠMT(CZ) EF16_019/0000729; GA MŠMT(CZ) EF18_053/0016940; GA MŠMT(CZ) LX22NPO5104
    Institutional support: RVO:61388963 ; RVO:61388955
    Keywords : triacylglycerol estolides * glycerol sn-regioisomers * estolide-branching isomers * collision-induced dissociation * higher-energy collisional dissociation * ozone-induced dissociation * high-resolution mass spectrometry
    OECD category: Analytical chemistry; Physical chemistry (UFCH-W)
    Impact factor: 5.5, year: 2022
    Method of publishing: Open access
    https://doi.org/10.3390/biom13030475

    Triacylglycerol estolides (TG-EST) are biologically active lipids extensively studied for their anti-inflammatory and anti-diabetic properties. In this work, eight standards of TG-EST were synthesized and systematically investigated by nanoelectrospray tandem mass spectrometry. Mass spectra of synthetic TG-EST were studied with the purpose of enabling the unambiguous identification of these lipids in biological samples. TG-EST glycerol sn-regioisomers and isomers with the fatty acid ester of hydroxy fatty acid (FAHFA) subunit branched in the ω-, α-, or 10-position were used. Ammonium, lithium, and sodium adducts of TG-EST formed by nanoelectrospray ionization were subjected to collision-induced dissociation (CID) and higher-energy collisional dissociation (HCD). Product ion spectra allowed for identification of fatty acid (FA) and FAHFA subunits originally linked to the glycerol backbone and distinguished the α-branching site of the FAHFA from other estolide-branching isomers. The ω- and 10-branching sites were determined by combining CID with ozone-induced dissociation (OzID). Lithium adducts provided the most informative product ions, enabling characterization of FA, hydroxy fatty acid (HFA), and FAHFA subunits. Glycerol sn-regioisomers were distinguished based on the relative abundance of product ions and unambiguously identified using CID/OzID of lithium and sodium adducts.
    Permanent Link: https://hdl.handle.net/11104/0341945

     
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    10.3390biom13030475.pdf12.7 MBPublisher’s postprintopen-access
     
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