A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Synthesis and enantiospecific analysis of enantiostructured triacylglycerols containing n-3 polyunsaturated fatty acids




Julkaisun tekijät: Kalpio M, Magnússon JD, Gudmundsson HG, Linderborg KM, Kallio H, Haraldsson GG, Yang B

Kustantaja: Elsevier Ireland Ltd.

Julkaisuvuosi: 2020

Journal: Chemistry and Physics of Lipids

Tietokannassa oleva lehden nimi: Chemistry and physics of lipids

Lehden akronyymi: Chem Phys Lipids

Volyymi: 231

Sivujen määrä: 10

ISSN: 0009-3084

eISSN: 1873-2941

DOI: http://dx.doi.org/10.1016/j.chemphyslip.2020.104937


Tiivistelmä
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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