A1 Refereed original research article in a scientific journal
Synthesis and enantiospecific analysis of enantiostructured triacylglycerols containing n-3 polyunsaturated fatty acids
Authors: Kalpio M, Magnússon JD, Gudmundsson HG, Linderborg KM, Kallio H, Haraldsson GG, Yang B
Publisher: Elsevier Ireland Ltd.
Publication year: 2020
Journal: Chemistry and Physics of Lipids
Journal name in source: Chemistry and physics of lipids
Journal acronym: Chem Phys Lipids
Article number: 104937
Volume: 231
Number of pages: 10
ISSN: 0009-3084
eISSN: 1873-2941
DOI: https://doi.org/10.1016/j.chemphyslip.2020.104937
Self-archived copy’s web address: https://research.utu.fi/converis/portal/detail/Publication/48475726
The stereospecific structure of triacylglycerols (TAGs) affects the bioavailability of fatty acids. Lack of enantiopure reference compounds and effective enantiospecific methods have hindered the stereospecific analysis of individual TAGs. Twelve novel enantiostructured AAB-type TAGs were synthesized containing one of the three n-3 polyunsaturated fatty acid: α-linolenic acid (ALA), eicosapentaenoic acid (EPA), or docosahexaenoic acid (DHA) in sn-1 or sn-3 position. These compounds formed six enantiomer pairs, which were separated with recycling high-performance liquid chromatography using chiral columns and UV detection. The chromatographic retention behavior of the enantiomers and the stereospecific elution order were studied. The enantiomer with an n-3 PUFA in the sn-1 position eluted faster than the enantiomer with the n-3 PUFA in the sn-3 position, regardless of the carbon chain length and number of double bonds of the PUFA. TAG enantiomers containing DHA exhibited highly different retention on the chiral column and were separated after the first column, whereas recycling was needed to separate the enantiomer pairs containing ALA or EPA. The system using two identical columns and one mobile phase, without sample derivatization, proved to be very effective also for peak purity assessment, confirming the enantiopurity of the synthesized structured TAGs being higher than 98 % (96 % ee).
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