Omega-3 fatty acids such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are essential for human health but prone to oxidation. While esterification location is known to influence the stability of omega-3 in triacylglycerols (TAGs) in oxidation trials, their oxidative behavior in the gastrointestinal tract is unknown. Synthesized ABA- and AAB-type TAGs containing DHA and EPA were submitted to static in vitro digestion for the first time. Tridocosahexaenoin and DHA as ethyl esters were similarly digested. Digesta were analyzed by gas chromatography, liquid chromatography-mass spectrometry, and nuclear magnetic resonance spectroscopy. Besides the formation of di- and monoacylglycerols, degradation of hydroperoxides was detected in ABA- and AAB-type TAGs, whereas oxygenated species increased in tridocosahexaenoin. Ethyl esters were mainly unaffected. EPA was expectedly less susceptible to oxidation prior to and during the digestion process, particularly in sn-2. These results are relevant for the production of tailored omega-3 structures to be used as supplements or ingredients.
Keywords: DHA; EPA; TAG enantiomers; ethyl ester; in vitro digestion; oxidation.