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Interactions of Oleanolic Acid, Apigenin, Rutin, Resveratrol and Ferulic Acid with Phosphatidylcholine Lipid Membranes - A Spectroscopic and Machine Learning Study

cris.virtual.author-orcid0000-0002-1438-1217
cris.virtual.author-orcid0000-0002-2535-8370
cris.virtual.author-orcid0000-0002-3604-4414
cris.virtual.author-orcid#PLACEHOLDER_PARENT_METADATA_VALUE#
cris.virtual.author-orcid#PLACEHOLDER_PARENT_METADATA_VALUE#
cris.virtualsource.author-orcid1c802429-36ee-40e7-b72f-32f16b32d8de
cris.virtualsource.author-orcid898dc715-0fc1-42af-a4d7-0bc909752fee
cris.virtualsource.author-orcid361d33cb-57c6-4034-a036-121c166e232d
cris.virtualsource.author-orcid#PLACEHOLDER_PARENT_METADATA_VALUE#
cris.virtualsource.author-orcid#PLACEHOLDER_PARENT_METADATA_VALUE#
dc.abstract.enBiologically active compounds present in the diet can interact with biological membranes (such as cell membranes), changing their properties. Their mutual interactions can influence their respective activities. In this study, we analyzed the interactions of oleanolic acid and phenolic compounds such as apigenin, rutin, resveratrol and ferulic acid with phosphatidylcholine membranes. Spectroscopic methods (fluorescence spectroscopy, dynamic light scattering) and machine learning were applied. The results of structural studies were compared with the antioxidant activity of the investigated substances in lipid membranes. In liposomes loaded with oleanolic acid, the pro-oxidant activity of resveratrol arises from changes in membrane structure, leading to an increased exposure of its hydrophilic region to external radicals. A similar mechanism may be involved in the pro-oxidant action of oleanolic acid. By contrast, apigenin, rutin and ferulic acid are present at the membrane surface. Their presence in this region protects the bilayer from radicals generated in the aqueous phase. Lower antioxidant activity observed in the case of ferulic aid is probably related to weaker interactions of this compound with the membrane, compared to the investigated flavonoids. Appropriate machine learning models for predicting oleanolic acid and phenolic compounds have been developed for the future application of intelligent predictive systems to optimizing manufacturing processes involving liposomes. The most effective regression model turned out to be the MLP 1:1-100-50-50-6:1, identifying resveratrol with a determination index of 0.83.
dc.affiliationWydział Nauk o Żywności i Żywieniu
dc.affiliation.instituteKatedra Biochemii i Analizy Żywności
dc.affiliation.instituteKatedra Mleczarstwa i Inżynierii Procesowej
dc.contributor.authorDwiecki, Krzysztof
dc.contributor.authorPrzybył, Krzysztof
dc.contributor.authorDezor, Dobrawa
dc.contributor.authorBąkowska, Ewa
dc.contributor.authorRocha, Silvia M.
dc.date.access2025-06-04
dc.date.accessioned2025-09-04T10:49:17Z
dc.date.available2025-09-04T10:49:17Z
dc.date.copyright2023-08-18
dc.date.issued2023
dc.description.abstract<jats:p>Biologically active compounds present in the diet can interact with biological membranes (such as cell membranes), changing their properties. Their mutual interactions can influence their respective activities. In this study, we analyzed the interactions of oleanolic acid and phenolic compounds such as apigenin, rutin, resveratrol and ferulic acid with phosphatidylcholine membranes. Spectroscopic methods (fluorescence spectroscopy, dynamic light scattering) and machine learning were applied. The results of structural studies were compared with the antioxidant activity of the investigated substances in lipid membranes. In liposomes loaded with oleanolic acid, the pro-oxidant activity of resveratrol arises from changes in membrane structure, leading to an increased exposure of its hydrophilic region to external radicals. A similar mechanism may be involved in the pro-oxidant action of oleanolic acid. By contrast, apigenin, rutin and ferulic acid are present at the membrane surface. Their presence in this region protects the bilayer from radicals generated in the aqueous phase. Lower antioxidant activity observed in the case of ferulic aid is probably related to weaker interactions of this compound with the membrane, compared to the investigated flavonoids. Appropriate machine learning models for predicting oleanolic acid and phenolic compounds have been developed for the future application of intelligent predictive systems to optimizing manufacturing processes involving liposomes. The most effective regression model turned out to be the MLP 1:1-100-50-50-6:1, identifying resveratrol with a determination index of 0.83.</jats:p>
dc.description.accesstimeat_publication
dc.description.bibliographyil., bibliogr.
dc.description.financepublication_nocost
dc.description.financecost0,00
dc.description.if2,5
dc.description.number16
dc.description.points100
dc.description.versionfinal_published
dc.description.volume13
dc.identifier.doi10.3390/app13169362
dc.identifier.issn2076-3417
dc.identifier.urihttps://sciencerep.up.poznan.pl/handle/item/4632
dc.identifier.weblinkhttps://www.mdpi.com/2076-3417/13/16/9362
dc.languageen
dc.relation.ispartofApplied Sciences (Switzerland)
dc.relation.pagesart. 9362
dc.rightsCC-BY
dc.sciencecloudnosend
dc.share.typeOPEN_JOURNAL
dc.subject.enoleanolic acid
dc.subject.enflavonoid
dc.subject.enresveratrol
dc.subject.enphenolic compounds
dc.subject.enantioxidant activity
dc.subject.enlipid membranes
dc.subject.enliposomes
dc.subject.enmachine learning
dc.subject.enregression
dc.subject.enmultilayer perceptron
dc.titleInteractions of Oleanolic Acid, Apigenin, Rutin, Resveratrol and Ferulic Acid with Phosphatidylcholine Lipid Membranes - A Spectroscopic and Machine Learning Study
dc.typeJournalArticle
dspace.entity.typePublication
oaire.citation.issue16
oaire.citation.volume13