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Conjugates of 1,3‐ and 1,2‐Acylglycerols with Stigmasterol: Synthesis, NMR Characterization, and Impact on Lipid Bilayers

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cris.virtualsource.author-orcid307551d0-aa67-4ae6-b57b-fb099d8300e7
dc.abstract.enThe main aim of research was synthesis and spectroscopic characterization of new conjugates in which stigmasterol was linked via carbonate or succinyl linker with 1,3- and 1,2-acylglycerols of palmitic and oleic acid. Acylglycerols containing stigmasterol residue at internal position have been synthesized from 2-benzyloxypropane-1,3-diol or dihydroxyacetone. Their asymmetric counterparts containing stigmasterol residue attached to sn-3 position have been obtained from (S)-solketal. Eight synthesized conjugates were used to create the liposomes as nanocarriers of phytosterols to increase their stability and protect them from degradation during thermal-oxidative treatments. Fluorimetric and ATR-FTIR methods were used to determine the impact of synthesized conjugates on the physicochemical properties of the lipid bilayer. The results indicate that conjugates with palmitic acid are better candidates for use as the potential stigmasterol nanocarriers compared to those with oleic acid because they increase the stiffness of the lipid bilayer and temperature of the main phase transition. The obtained results are the first step in designing of stigmasterol-enriched liposomal carriers with higher thermo-oxidative stability for their potential use in the food industry.
dc.affiliationWydział Nauk o Żywności i Żywieniu
dc.affiliation.instituteKatedra Technologii Żywności Pochodzenia Roślinnego
dc.contributor.authorGładkowski, Witold
dc.contributor.authorChojnacka, Anna
dc.contributor.authorWłoch, Aleksandra
dc.contributor.authorPruchnik, Hanna
dc.contributor.authorGrudniewska, Aleksandra
dc.contributor.authorDunal, Anna
dc.contributor.authorDudek, Anita
dc.contributor.authorMaciejewska, Gabriela
dc.contributor.authorRudzińska, Magdalena
dc.date.access2025-06-10
dc.date.accessioned2025-09-19T06:07:36Z
dc.date.available2025-09-19T06:07:36Z
dc.date.copyright2023-03-30
dc.date.issued2023
dc.description.abstract<jats:title>Abstract</jats:title><jats:p>The main aim of research was synthesis and spectroscopic characterization of new conjugates in which stigmasterol was linked via carbonate or succinyl linker with 1,3‐ and 1,2‐acylglycerols of palmitic and oleic acid. Acylglycerols containing stigmasterol residue at internal position have been synthesized from 2‐benzyloxypropane‐1,3‐diol or dihydroxyacetone. Their asymmetric counterparts containing stigmasterol residue attached to <jats:italic>sn</jats:italic>‐3 position have been obtained from (<jats:italic>S</jats:italic>)‐solketal. Eight synthesized conjugates were used to create the liposomes as nanocarriers of phytosterols to increase their stability and protect them from degradation during thermal‐oxidative treatments. Fluorimetric and ATR‐FTIR methods were used to determine the impact of synthesized conjugates on the physicochemical properties of the lipid bilayer. The results indicate that conjugates with palmitic acid are better candidates for use as the potential stigmasterol nanocarriers compared to those with oleic acid because they increase the stiffness of the lipid bilayer and temperature of the main phase transition. The obtained results are the first step in designing of stigmasterol‐enriched liposomal carriers with higher thermo‐oxidative stability for their potential use in the food industry.</jats:p>
dc.description.accesstimeat_publication
dc.description.bibliographyil., bibliogr.
dc.description.financepublication_nocost
dc.description.financecost0,00
dc.description.if3,0
dc.description.number5
dc.description.points100
dc.description.versionfinal_published
dc.description.volume88
dc.identifier.doi10.1002/cplu.202300161
dc.identifier.issn2192-6506
dc.identifier.urihttps://sciencerep.up.poznan.pl/handle/item/4934
dc.identifier.weblinkhttps://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cplu.202300161
dc.languageen
dc.relation.ispartofChemPlusChem
dc.relation.pagese202300161
dc.rightsCC-BY-NC-ND
dc.sciencecloudsend
dc.share.typeOTHER
dc.subject.enacylglycerols
dc.subject.enesterification
dc.subject.enlipids
dc.subject.enliposomes
dc.subject.enphytosterols
dc.titleConjugates of 1,3‐ and 1,2‐Acylglycerols with Stigmasterol: Synthesis, NMR Characterization, and Impact on Lipid Bilayers
dc.typeJournalArticle
dspace.entity.typePublication
oaire.citation.issue5
oaire.citation.volume88