Hydroxytyrosyl Eicosapentaenoate as a Potential Antioxidant for Omega-3 Fatty Acids: Improved Synthesis and Comparative Evaluation with Other Natural Antioxidants

Hydroxytyrosol (HT), the primary phenolic compound in virgin olive oil, has notable cardiovascular benefits, particularly in preventing low-density lipoprotein (LDL) oxidation. However, its hydrophilicity limits its solubility and integration into lipid-based formulations. This study aimed to enhanc...

Descripción completa

Detalles Bibliográficos
Autores: García Acosta, Natalia, Cert, Rosa, Jordán, Marta, Goya, Luis, Mateos, Raquel, Espartero Sánchez, José Luis
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2025
País:España
Institución:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/178836
Acceso en línea:https://hdl.handle.net/11441/178836
https://doi.org/10.3390/biom15050714
Access Level:acceso abierto
Palabra clave:Hydroxytyrosol
Omega-3 fatty acids
Antioxidant capacity
Enzymatic synthesis
Hydroxytyrosyl eicosapentaenoate
id ES_ca6d3b087dcc15f3cbd3f1df33171ba2
oai_identifier_str oai:idus.us.es:11441/178836
network_acronym_str ES
network_name_str España
repository_id_str
spelling Hydroxytyrosyl Eicosapentaenoate as a Potential Antioxidant for Omega-3 Fatty Acids: Improved Synthesis and Comparative Evaluation with Other Natural AntioxidantsGarcía Acosta, NataliaCert, RosaJordán, MartaGoya, LuisMateos, RaquelEspartero Sánchez, José LuisHydroxytyrosolOmega-3 fatty acidsAntioxidant capacityEnzymatic synthesisHydroxytyrosyl eicosapentaenoateHydroxytyrosol (HT), the primary phenolic compound in virgin olive oil, has notable cardiovascular benefits, particularly in preventing low-density lipoprotein (LDL) oxidation. However, its hydrophilicity limits its solubility and integration into lipid-based formulations. This study aimed to enhance its lipophilicity by synthesizing hydroxytyrosyl eicosapentaenoate (HT-EPA), a derivative of HT and eicosapentaenoic acid (EPA), using a one-step enzymatic catalysis with lipase B from Candida antarctica (CALB). The reaction, performed as a suspension of HT in ethyl eicosapentaenoate (Et-EPA) (1:9 molar ratio) under vacuum, achieved higher yields and shorter reaction times than previously reported, with a purity exceeding 98%, confirmed by 1H-NMR. For the first time, the antioxidant capacity of HT-EPA in comparison with other natural antioxidants was assessed using the FRAP assay, while its oxidative stability in an omega-3-rich oil matrix was evaluated via the Rancimat method. HT-EPA and hydroxytyrosyl acetate (HT-Ac) displayed antioxidant activity comparable to HT but significantly higher than α-tocopherol, a common food antioxidant. Given the scarcity of effective lipid-soluble antioxidants, HT-EPA represents a promising candidate for omega-3 nutraceuticals, offering enhanced stability and potential health benefits. This study provides a simple, efficient, and scalable strategy for developing functional lipid-based formulations with cardioprotective potential by improving HT solubility while preserving its antioxidant properties.Multidisciplinary Digital Publishing Institute (MDPI)Química Orgánica y FarmacéuticaMinisterio de Ciencia, Innovación y Universidades (MICIU). EspañaMinisterio de Ciencia e Innovación (MICIN). España2025info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfapplication/pdfhttps://hdl.handle.net/11441/178836https://doi.org/10.3390/biom15050714reponame:idUS. Depósito de Investigación de la Universidad de Sevillainstname:Universidad de Sevilla (US)InglésBiomolecules, 15 (5), 714.ID2021-125259OB-I00PRE2022-105658RE2022- 102252https://doi.org/10.3390/biom15050714info:eu-repo/semantics/openAccessoai:idus.us.es:11441/1788362026-06-17T12:51:07Z
dc.title.none.fl_str_mv Hydroxytyrosyl Eicosapentaenoate as a Potential Antioxidant for Omega-3 Fatty Acids: Improved Synthesis and Comparative Evaluation with Other Natural Antioxidants
title Hydroxytyrosyl Eicosapentaenoate as a Potential Antioxidant for Omega-3 Fatty Acids: Improved Synthesis and Comparative Evaluation with Other Natural Antioxidants
spellingShingle Hydroxytyrosyl Eicosapentaenoate as a Potential Antioxidant for Omega-3 Fatty Acids: Improved Synthesis and Comparative Evaluation with Other Natural Antioxidants
García Acosta, Natalia
Hydroxytyrosol
Omega-3 fatty acids
Antioxidant capacity
Enzymatic synthesis
Hydroxytyrosyl eicosapentaenoate
title_short Hydroxytyrosyl Eicosapentaenoate as a Potential Antioxidant for Omega-3 Fatty Acids: Improved Synthesis and Comparative Evaluation with Other Natural Antioxidants
title_full Hydroxytyrosyl Eicosapentaenoate as a Potential Antioxidant for Omega-3 Fatty Acids: Improved Synthesis and Comparative Evaluation with Other Natural Antioxidants
title_fullStr Hydroxytyrosyl Eicosapentaenoate as a Potential Antioxidant for Omega-3 Fatty Acids: Improved Synthesis and Comparative Evaluation with Other Natural Antioxidants
title_full_unstemmed Hydroxytyrosyl Eicosapentaenoate as a Potential Antioxidant for Omega-3 Fatty Acids: Improved Synthesis and Comparative Evaluation with Other Natural Antioxidants
title_sort Hydroxytyrosyl Eicosapentaenoate as a Potential Antioxidant for Omega-3 Fatty Acids: Improved Synthesis and Comparative Evaluation with Other Natural Antioxidants
dc.creator.none.fl_str_mv García Acosta, Natalia
Cert, Rosa
Jordán, Marta
Goya, Luis
Mateos, Raquel
Espartero Sánchez, José Luis
author García Acosta, Natalia
author_facet García Acosta, Natalia
Cert, Rosa
Jordán, Marta
Goya, Luis
Mateos, Raquel
Espartero Sánchez, José Luis
author_role author
author2 Cert, Rosa
Jordán, Marta
Goya, Luis
Mateos, Raquel
Espartero Sánchez, José Luis
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Química Orgánica y Farmacéutica
Ministerio de Ciencia, Innovación y Universidades (MICIU). España
Ministerio de Ciencia e Innovación (MICIN). España
dc.subject.none.fl_str_mv Hydroxytyrosol
Omega-3 fatty acids
Antioxidant capacity
Enzymatic synthesis
Hydroxytyrosyl eicosapentaenoate
topic Hydroxytyrosol
Omega-3 fatty acids
Antioxidant capacity
Enzymatic synthesis
Hydroxytyrosyl eicosapentaenoate
description Hydroxytyrosol (HT), the primary phenolic compound in virgin olive oil, has notable cardiovascular benefits, particularly in preventing low-density lipoprotein (LDL) oxidation. However, its hydrophilicity limits its solubility and integration into lipid-based formulations. This study aimed to enhance its lipophilicity by synthesizing hydroxytyrosyl eicosapentaenoate (HT-EPA), a derivative of HT and eicosapentaenoic acid (EPA), using a one-step enzymatic catalysis with lipase B from Candida antarctica (CALB). The reaction, performed as a suspension of HT in ethyl eicosapentaenoate (Et-EPA) (1:9 molar ratio) under vacuum, achieved higher yields and shorter reaction times than previously reported, with a purity exceeding 98%, confirmed by 1H-NMR. For the first time, the antioxidant capacity of HT-EPA in comparison with other natural antioxidants was assessed using the FRAP assay, while its oxidative stability in an omega-3-rich oil matrix was evaluated via the Rancimat method. HT-EPA and hydroxytyrosyl acetate (HT-Ac) displayed antioxidant activity comparable to HT but significantly higher than α-tocopherol, a common food antioxidant. Given the scarcity of effective lipid-soluble antioxidants, HT-EPA represents a promising candidate for omega-3 nutraceuticals, offering enhanced stability and potential health benefits. This study provides a simple, efficient, and scalable strategy for developing functional lipid-based formulations with cardioprotective potential by improving HT solubility while preserving its antioxidant properties.
publishDate 2025
dc.date.none.fl_str_mv 2025
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/11441/178836
https://doi.org/10.3390/biom15050714
url https://hdl.handle.net/11441/178836
https://doi.org/10.3390/biom15050714
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Biomolecules, 15 (5), 714.
ID2021-125259OB-I00
PRE2022-105658
RE2022- 102252
https://doi.org/10.3390/biom15050714
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute (MDPI)
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute (MDPI)
dc.source.none.fl_str_mv reponame:idUS. Depósito de Investigación de la Universidad de Sevilla
instname:Universidad de Sevilla (US)
instname_str Universidad de Sevilla (US)
reponame_str idUS. Depósito de Investigación de la Universidad de Sevilla
collection idUS. Depósito de Investigación de la Universidad de Sevilla
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869419478912073729
score 15,811543

Similares en LA Referencia