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Preparation of Triacylglycerols Rich in Omega-3 Fatty Acids from Sardine Oil Using a Rhizomucor miehei Lipase: Focus in the EPA/DHA Ratio

2013-11-29Artigo científico Acesso restrito
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datacite.subject.fosCiências Naturais::Ciências Biológicas
datacite.subject.fosCiências Naturais::Ciências Químicas
datacite.subject.sdg12:Produção e Consumo Sustentáveis
datacite.subject.sdg13:Ação Climática
datacite.subject.sdg14:Proteger a Vida Marinha
dc.contributor.authorBispo, Paulo
dc.contributor.authorBatista, Irineu
dc.contributor.authorBernardino, Raul J.
dc.contributor.authorBandarra, Narcisa Maria
dc.date.accessioned2026-06-15T11:09:26Z
dc.date.available2026-06-15T11:09:26Z
dc.date.issued2013-11-29
dc.description.abstractThe increasing evidence on the differential biochemical effects of eicosapentaenoic acid (EPA)/docosahexaenoic acid (DHA) raises the need of n-3 highly unsaturated fatty acid concentrates with different amounts of these fatty acids. In the present work, physicochemical and enzymatic techniques were combined to obtain acylglycerols, mainly triacylglycerols (TAG), rich in n-3 fatty acids. Sardine oil was obtained by washing sardine (Sardina pilchardus) mince with a NaHCO3 solution, hydrolyzed in a KOH-ethanol solution, and concentrated with urea. The esterification reaction was performed in the stoichiometric proportion of substrates for re-esterification to TAG, with 10 % level of Rhizomucor miehei lipase based on the weight of substrates, without any solvent, during 48 h. This procedure led to approximately 88 % of acylglycerols, where more than 66 % were TAG and the concentration of n-3 fatty acids was higher than 60 %, the EPA and DHA ratio (EPA/DHA) was 4:1. The content of DHA in the unesterifed fraction (free fatty acids) increased from 20 to 54 %, while the EPA level in the same fraction decreased from 33 to 12.5 % (EPA/DHA ratio ≈1:4). Computational methods (density functional theory calculations) have been carried out at the B3LYP/6-31G(d,p) level to explain some of the experimental results.eng
dc.identifier.citationBispo, P., Batista, I., Bernardino, R.J. et al. Preparation of Triacylglycerols Rich in Omega-3 Fatty Acids from Sardine Oil Using a Rhizomucor miehei Lipase: Focus in the EPA/DHA Ratio. Appl Biochem Biotechnol 172, 1866–1881 (2014). https://doi.org/10.1007/s12010-013-0616-1.
dc.identifier.doi10.1007/s12010-013-0616-1
dc.identifier.eissn1559-0291
dc.identifier.issn0273-2289
dc.identifier.urihttp://hdl.handle.net/10400.8/16416
dc.language.isoeng
dc.peerreviewedyes
dc.publisherSpringer Nature
dc.relation.hasversionhttps://link.springer.com/article/10.1007/s12010-013-0616-1
dc.relation.ispartofApplied Biochemistry and Biotechnology
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectn-3HUFA
dc.subjectEPA/DHAratios
dc.subjectTriacylglycerols
dc.subjectRhizomucor miehei lipase
dc.subjectSardine oil
dc.subjectAb initio geometry optimization
dc.titlePreparation of Triacylglycerols Rich in Omega-3 Fatty Acids from Sardine Oil Using a Rhizomucor miehei Lipase: Focus in the EPA/DHA Ratioeng
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage1881
oaire.citation.issue4
oaire.citation.startPage1866
oaire.citation.titleApplied Biochemistry and Biotechnology
oaire.citation.volume172
oaire.versionhttp://purl.org/coar/version/c_970fb48d4fbd8a85
person.familyNameBernardino
person.givenNameRaul
person.identifier.ciencia-idD01B-E5E2-6040
person.identifier.orcid0000-0002-7775-0614
person.identifier.ridA-2338-2010
relation.isAuthorOfPublication915a2334-757a-4011-968c-94e7d391b7ac
relation.isAuthorOfPublication.latestForDiscovery915a2334-757a-4011-968c-94e7d391b7ac

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The increasing evidence on the differential biochemical effects of eicosapentaenoic acid (EPA)/docosahexaenoic acid (DHA) raises the need of n-3 highly unsaturated fatty acid concentrates with different amounts of these fatty acids. In the present work, physicochemical and enzymatic techniques were combined to obtain acylglycerols, mainly triacylglycerols (TAG), rich in n-3 fatty acids. Sardine oil was obtained by washing sardine (Sardina pilchardus) mince with a NaHCO3 solution, hydrolyzed in a KOH-ethanol solution, and concentrated with urea. The esterification reaction was performed in the stoichiometric proportion of substrates for re-esterification to TAG, with 10 % level of Rhizomucor miehei lipase based on the weight of substrates, without any solvent, during 48 h. This procedure led to approximately 88 % of acylglycerols, where more than 66 % were TAG and the concentration of n-3 fatty acids was higher than 60 %, the EPA and DHA ratio (EPA/DHA) was 4:1. The content of DHA in the unesterifed fraction (free fatty acids) increased from 20 to 54 %, while the EPA level in the same fraction decreased from 33 to 12.5 % (EPA/DHA ratio ≈1:4). Computational methods (density functional theory calculations) have been carried out at the B3LYP/6-31G(d,p) level to explain some of the experimental results.
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