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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2021
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ftdoajarticles:oai:doaj.org/article:45bb87254168456bb8e23a5eda0ea124 2023-05-15T13:56:28+02:00 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 Gretel Dovale-Rosabal Alicia Rodríguez Alejandra Espinosa Andrés Barriga Santiago P. Aubourg 2021-05-01T00:00:00Z https://doi.org/10.3390/molecules26113094 https://doaj.org/article/45bb87254168456bb8e23a5eda0ea124 EN eng MDPI AG https://www.mdpi.com/1420-3049/26/11/3094 https://doaj.org/toc/1420-3049 doi:10.3390/molecules26113094 1420-3049 https://doaj.org/article/45bb87254168456bb8e23a5eda0ea124 Molecules, Vol 26, Iss 3094, p 3094 (2021) n -3 LCPUFA EPA/DHA sn -2 position salmon oil immobilized lipase B Candida antarctica (nonspecific) CO 2 supercritical extraction Organic chemistry QD241-441 article 2021 ftdoajarticles https://doi.org/10.3390/molecules26113094 2022-12-31T09:12:13Z 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. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Molecules 26 11 3094 |
institution |
Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
n -3 LCPUFA EPA/DHA sn -2 position salmon oil immobilized lipase B Candida antarctica (nonspecific) CO 2 supercritical extraction Organic chemistry QD241-441 |
spellingShingle |
n -3 LCPUFA EPA/DHA sn -2 position salmon oil immobilized lipase B Candida antarctica (nonspecific) CO 2 supercritical extraction Organic chemistry QD241-441 Gretel Dovale-Rosabal Alicia Rodríguez Alejandra Espinosa Andrés Barriga Santiago P. Aubourg 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 |
topic_facet |
n -3 LCPUFA EPA/DHA sn -2 position salmon oil immobilized lipase B Candida antarctica (nonspecific) CO 2 supercritical extraction Organic chemistry QD241-441 |
description |
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. |
format |
Article in Journal/Newspaper |
author |
Gretel Dovale-Rosabal Alicia Rodríguez Alejandra Espinosa Andrés Barriga Santiago P. Aubourg |
author_facet |
Gretel Dovale-Rosabal Alicia Rodríguez Alejandra Espinosa Andrés Barriga Santiago P. Aubourg |
author_sort |
Gretel Dovale-Rosabal |
title |
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 |
title_short |
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 |
title_full |
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 |
title_fullStr |
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 |
title_full_unstemmed |
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 |
title_sort |
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 |
publisher |
MDPI AG |
publishDate |
2021 |
url |
https://doi.org/10.3390/molecules26113094 https://doaj.org/article/45bb87254168456bb8e23a5eda0ea124 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Molecules, Vol 26, Iss 3094, p 3094 (2021) |
op_relation |
https://www.mdpi.com/1420-3049/26/11/3094 https://doaj.org/toc/1420-3049 doi:10.3390/molecules26113094 1420-3049 https://doaj.org/article/45bb87254168456bb8e23a5eda0ea124 |
op_doi |
https://doi.org/10.3390/molecules26113094 |
container_title |
Molecules |
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26 |
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11 |
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3094 |
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1766263980258492416 |