Antioxidative Effect of Dihydrosphingosine (d18:0) and α-Tocopherol on Tridocosahexaenoin (DHA-TAG)

Abstract

Sphingoid bases have shown promise as effective antioxidants in fish oils together with α-tocopherol, and the effect has been attributed to products resulting from amino−carbonyl reactions (lipation products) between the sphingoid base amine group and carbonyl compounds from lipid oxidation. In this study, the synergistic effect of dihydrosphingosine (d18:0) and αtocopherol was studied on pure docosahexaenoic acid (DHA) triacylglycerols with an omics-type liquid-and gas-chromatographic mass spectrometric approach to verify the synergistic effect, to get a comprehensive view on the effect of d18:0 on the oxidation pattern, and to identify the lipation products. The results confirmed that d18:0 rapidly reacts further in the presence of lipid oxidation products and α-tocopherol. α-Tocopherol and d18:0 showed an improved antioxidative effect after 12 h of oxidation, indicating the formation of antioxidants through carbonyl−amine reactions. Imines formed from the carbonyls and d18:0 could be tentatively identified.

Chemoenzymatic Synthesis of ABC-Type Enantiostructured Triacylglycerols by the Use of the p-Methoxybenzyl Protective Group

“…The primary role of enantiostructured TAGs as standards for the enantiospecific analysis of chiral TAGs commonly present in natural fats and oils has already been demonstrated [4,7], and similar analyses of the TAGs obtained from the current work are underway to be reported within a few months. Furthermore, the enantiostructured TAGs have also found use in various important biological activities that include bioavailability [14][15][16][17] and oxidative stability [17][18][19] studies of bioactive n-3 polyunsaturated fatty acids, with a special emphasis on their location in terms of the stereospecific positions within the TAGs.…”