Synthesis of EPA- and DHA-Enriched Structured Acylglycerols at the sn -2 Position Starting from Commercial Salmon Oil by Enzymatic Lipase Catalysis under Supercritical Conditions

There is consistent evidence that long-chain polyunsaturated fatty acids (LCPUFA) belonging to the n -3 series, i.e., eicosapentaenoic (20:5 n -3, EPA) and docosahexaenoic (22:6 n -3, DHA) acids, decrease the risk of heart, circulatory and inflammatory diseases. Furthermore, the bioavailability of s...

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Bibliographic Details
Published in:Molecules
Main Authors: Gretel Dovale-Rosabal, Alicia Rodríguez, Alejandra Espinosa, Andrés Barriga, Santiago P. Aubourg
Format: Article in Journal/Newspaper
Language:English
Published: MDPI AG 2021
Subjects:
n -3 LCPUFA
EPA/DHA sn -2 position
salmon oil
immobilized lipase B
Candida antarctica (nonspecific)
CO 2 supercritical extraction
Organic chemistry
QD241-441
Antarc*
Antarctica
Online Access:https://doi.org/10.3390/molecules26113094
https://doaj.org/article/45bb87254168456bb8e23a5eda0ea124
Description
Summary:There is consistent evidence that long-chain polyunsaturated fatty acids (LCPUFA) belonging to the n -3 series, i.e., eicosapentaenoic (20:5 n -3, EPA) and docosahexaenoic (22:6 n -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 CO 2 supercritical conditions (CO 2 SC). According to the CO 2 SC 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.

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