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Acylglycerols of Myristic Acid as New Candidates for Effective Stigmasterol Delivery—Design, Synthesis, and the Influence on Physicochemical Properties of Liposomes

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cris.virtualsource.author-orcid307551d0-aa67-4ae6-b57b-fb099d8300e7
dc.abstract.enNew carriers of phytosterols; acylglycerols containing natural myristic acid at sn-1 and sn-3 positions and stigmasterol residue linked to sn-2 position by carbonate and succinate linker have been designed and synthesized in three-step synthesis from dihydroxyacetone (DHA). The synthetic pathway involved Steglich esterification of DHA with myristic acid; reduction of carbonyl group of 1,3-dimyristoylpropanone and esterification of 1,3-dimyristoylglicerol with stigmasterol chloroformate or stigmasterol hemisuccinate. The structure of the obtained hybrids was established by the spectroscopic methods (NMR; IR; HRMS). Obtained hybrid molecules were used to form new liposomes in the mixture with model phospholipid and their effect on their physicochemical properties was determined, including the polarity, fluidity, and main phase transition of liposomes using differential scanning calorimetry and fluorimetric methods. The results confirm the significant effect of both stigmasterol-containing acylglycerols on the hydrophilic and hydrophobic region of liposome membranes. They significantly increase the order in the polar heads of the lipid bilayer and increase the rigidity in the hydrophobic region. Moreover, the presence of both acylglycerols in the membranes shifts the temperature of the main phase transition towards higher temperatures. Our results indicate stabilization of the bilayer over a wide temperature range (above and below the phase transition temperature), which in addition to the beneficial effects of phytosterols on human health makes them more attractive components of novel lipid nanocarriers compared to cholesterol.
dc.affiliationWydział Nauk o Żywności i Żywieniu
dc.affiliation.instituteKatedra Technologii Żywności Pochodzenia Roślinnego
dc.contributor.authorGładkowski, Witold
dc.contributor.authorWłoch, Aleksandra
dc.contributor.authorPruchnik, Hanna
dc.contributor.authorChojnacka, Anna
dc.contributor.authorGrudniewska, Aleksandra
dc.contributor.authorWysota, Agnieszka
dc.contributor.authorDunal, Anna
dc.contributor.authorRubiano Castro, Daniel
dc.contributor.authorRudzińska, Magdalena
dc.date.access2026-03-10
dc.date.accessioned2026-03-20T10:12:46Z
dc.date.available2026-03-20T10:12:46Z
dc.date.copyright2022-05-25
dc.date.issued2022
dc.description.abstract<jats:p>New carriers of phytosterols; acylglycerols containing natural myristic acid at sn-1 and sn-3 positions and stigmasterol residue linked to sn-2 position by carbonate and succinate linker have been designed and synthesized in three-step synthesis from dihydroxyacetone (DHA). The synthetic pathway involved Steglich esterification of DHA with myristic acid; reduction of carbonyl group of 1,3-dimyristoylpropanone and esterification of 1,3-dimyristoylglicerol with stigmasterol chloroformate or stigmasterol hemisuccinate. The structure of the obtained hybrids was established by the spectroscopic methods (NMR; IR; HRMS). Obtained hybrid molecules were used to form new liposomes in the mixture with model phospholipid and their effect on their physicochemical properties was determined, including the polarity, fluidity, and main phase transition of liposomes using differential scanning calorimetry and fluorimetric methods. The results confirm the significant effect of both stigmasterol-containing acylglycerols on the hydrophilic and hydrophobic region of liposome membranes. They significantly increase the order in the polar heads of the lipid bilayer and increase the rigidity in the hydrophobic region. Moreover, the presence of both acylglycerols in the membranes shifts the temperature of the main phase transition towards higher temperatures. Our results indicate stabilization of the bilayer over a wide temperature range (above and below the phase transition temperature), which in addition to the beneficial effects of phytosterols on human health makes them more attractive components of novel lipid nanocarriers compared to cholesterol.</jats:p>
dc.description.accesstimeat_publication
dc.description.bibliographyil., bibliogr
dc.description.financepublication_nocost
dc.description.financecost0,00
dc.description.if4,6
dc.description.number11
dc.description.points140
dc.description.versionfinal_published
dc.description.volume27
dc.identifier.doi10.3390/molecules27113406
dc.identifier.issn1420-3049
dc.identifier.urihttps://sciencerep.up.poznan.pl/handle/item/7833
dc.identifier.weblinkhttps://www.mdpi.com/1420-3049/27/11/3406
dc.languageen
dc.relation.ispartofMolecules
dc.relation.pagesart. 3406
dc.rightsCC-BY
dc.sciencecloudnosend
dc.share.typeOPEN_JOURNAL
dc.subject.ennew lipid nanocarriers
dc.subject.enliposomes
dc.subject.enacylglycerols
dc.subject.enstigmasterol
dc.subject.enSteglich esterification
dc.subject.enphysicochemical properties
dc.titleAcylglycerols of Myristic Acid as New Candidates for Effective Stigmasterol Delivery—Design, Synthesis, and the Influence on Physicochemical Properties of Liposomes
dc.typeJournalArticle
dspace.entity.typePublication
oaire.citation.issue11
oaire.citation.volume27