Abstract
There is consistent evidence that long-chain polyunsaturated fatty acids (LCPUFA) belonging to the n-3 series, i.e., eicosapentaenoic (20:5n-3, EPA) and docosahexaenoic (22:6n-3, DHA) acids, decrease the risk of heart, circulatory and inflammatory diseases. Furthermore, the bioavailability of such fatty acids has been shown to depend on their location in triacylglycerol (TG) molecules at the sn-2 position. Consequently, great attention has been accorded to the synthesis of structured acylglycerols (sAG), which include EPA or DHA at the sn-2 position. The aim of this work was to synthesize sAG starting from deodorized refined commercial salmon oil. For this, immobilized lipase B from Candida antarctica (nonspecific) was used as a catalyst for the intra–interesterification process under CO2 supercritical conditions (CO2SC). According to the CO2SC reaction time, three different fractions including sAG compounds were obtained. The location of EPA and DHA at the sn-2 position in the resulting glycerol backbone was identified by mass spectrometry (MALDI-TOF) analysis. In all fractions obtained, a marked decrease in the starting TG content was observed, while an increase in the DHA content at the sn-2 position was detected. The fraction obtained after the longest reaction time period (2 h) led to the highest yield of sn-2 position DHA in the resulting sAG molecule.
Highlights
There is consistent evidence that n-3 long-chain polyunsaturated fatty acids (n-3 LCPUFA) produce important health benefits, evidencing their role as mediating bioactive lipids within the protective action exerted by diets rich in these compounds [1]
Values obtained for the free fatty acids (FFA) content, peroxide value (PV), p-anisidine value (AV) and total oxidation (TOTOX) (0.20 ± 0.00 g oleic acid/100 g oil; 0.40 ± 0.00 meq active oxygen/kg oil; 1.13 ± 0.02; and 1.93 ± 0.02, respectively) reveal low lipid oxidation and hydrolytic development, which agrees with previous research on different kinds of fish oils, including salmon oil [29,30,31]
It was observed that EPA is more likely to be found in the sn-2 position, while DHA is mostly located in the sn-3 position in TG of Deodorized Refined Commercial Salmon Oil (DRCSO)
Summary
There is consistent evidence that n-3 long-chain polyunsaturated fatty acids (n-3 LCPUFA) produce important health benefits, evidencing their role as mediating bioactive lipids within the protective action exerted by diets rich in these compounds [1]. A low n-6/n-3 ratio, together with the daily consumption of n-3 LCPUFA, exerts a great influence on the prevention of non-communicable diseases [3], as well as on the decrease in mortality and cardiac risk [4]. A diet rich in n-3 LCPUFA plays an important role in the last trimester of pregnancy and in child nutrition, since DHA especially influences the development and functioning of the nervous system and visual organs of fetuses and newborns [6]. In addition to the consumption of fish, other products containing n-3 LCPUFA are currently used, such as capsules and foods declared safe from a chemical, organoleptic and toxicological point of view
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