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 (20:5n-3, EPA) and docosahexaenoic (22:6n-3, DHA) acids, decrease the risk of heart, circulatory and inflammatory diseases. Furthermore, the bioavailability of such f...
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ftunivchile:oai:repositorio.uchile.cl:2250/182390 2023-05-15T13:38:36+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 Dovale Rosabal, Gretel Rodríguez Melis, Alicia Espinosa Escalona, Berta Alejandra Barriga Pinto, Gonzalo Andrés Aubourg Martín, Santiago Pedro 2021 application/pdf https://doi.org/10.3390/molecules26113094 https://repositorio.uchile.cl/handle/2250/182390 en eng MDPI Molecules 2021, 26, 3094 doi:10.3390/molecules26113094 https://repositorio.uchile.cl/handle/2250/182390 Attribution-NonCommercial-NoDerivs 3.0 United States http://creativecommons.org/licenses/by-nc-nd/3.0/us/ CC-BY-NC-ND Molecules n-3 LCPUFA EPA/DHA sn-2 position Salmon oil Immobilized lipase B Candida antarctica (nonspecific) CO2 supercritical extraction Structured acylglycerols Intra–interesterification MALDI-TOF Artículo de revista 2021 ftunivchile https://doi.org/10.3390/molecules26113094 2021-10-30T23:48:48Z 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. Comision Nacional de Investigacion Cientifica y Tecnologica (CONICYT) CONICYT FONDECYT 1181774 Versión publicada - versión final del editor Article in Journal/Newspaper Antarc* Antarctica Universidad de Chile: Repositorio académico Molecules 26 11 3094 |
institution |
Open Polar |
collection |
Universidad de Chile: Repositorio académico |
op_collection_id |
ftunivchile |
language |
English |
topic |
n-3 LCPUFA EPA/DHA sn-2 position Salmon oil Immobilized lipase B Candida antarctica (nonspecific) CO2 supercritical extraction Structured acylglycerols Intra–interesterification MALDI-TOF |
spellingShingle |
n-3 LCPUFA EPA/DHA sn-2 position Salmon oil Immobilized lipase B Candida antarctica (nonspecific) CO2 supercritical extraction Structured acylglycerols Intra–interesterification MALDI-TOF Dovale Rosabal, Gretel Rodríguez Melis, Alicia Espinosa Escalona, Berta Alejandra Barriga Pinto, Gonzalo Andrés Aubourg Martín, Santiago Pedro 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) CO2 supercritical extraction Structured acylglycerols Intra–interesterification MALDI-TOF |
description |
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. Comision Nacional de Investigacion Cientifica y Tecnologica (CONICYT) CONICYT FONDECYT 1181774 Versión publicada - versión final del editor |
format |
Article in Journal/Newspaper |
author |
Dovale Rosabal, Gretel Rodríguez Melis, Alicia Espinosa Escalona, Berta Alejandra Barriga Pinto, Gonzalo Andrés Aubourg Martín, Santiago Pedro |
author_facet |
Dovale Rosabal, Gretel Rodríguez Melis, Alicia Espinosa Escalona, Berta Alejandra Barriga Pinto, Gonzalo Andrés Aubourg Martín, Santiago Pedro |
author_sort |
Dovale Rosabal, Gretel |
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 |
publishDate |
2021 |
url |
https://doi.org/10.3390/molecules26113094 https://repositorio.uchile.cl/handle/2250/182390 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Molecules |
op_relation |
Molecules 2021, 26, 3094 doi:10.3390/molecules26113094 https://repositorio.uchile.cl/handle/2250/182390 |
op_rights |
Attribution-NonCommercial-NoDerivs 3.0 United States http://creativecommons.org/licenses/by-nc-nd/3.0/us/ |
op_rightsnorm |
CC-BY-NC-ND |
op_doi |
https://doi.org/10.3390/molecules26113094 |
container_title |
Molecules |
container_volume |
26 |
container_issue |
11 |
container_start_page |
3094 |
_version_ |
1766108651059150848 |