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Unexpected Role of pH and Microenvironment on the Antioxidant and Synergistic Activity of Resveratrol in Model Micellar and Liposomal Systems

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dc.abstract.enExperimental and theoretical studies indicate that resveratrol (RSV, dietary polyphenol that effectively reduces cellular oxidative stress) is a good scavenger of hydroxyl, alkoxyl, and peroxy radicals in homogeneous systems. However, the role of RSV as a chain-breaking antioxidant is still questioned. Here, we describe pH dependent effectiveness of RSV as an inhibitor of peroxidation of methyl linoleate in Triton X-100 micelles and in 1,2-dimyristoylsn-glycero-3-phosphocholine (DMPC) liposomes, with the best effectiveness at pH 6 (stoichiometric factors, n, are 4.9 and 5.6, and the rate constants for reaction with peroxyl radicals, kinh, are 1200 and 3300 M−1 s−1 in micellar and liposomal systems, respectively).We propose the mechanism in which RSV-derived radicals are coupled to dimers with recovered ability to trap lipidperoxyl radicals. The formation of such dimers is facilitated due to increased local concentration of RSV at the lipid−water interface. Good synergy of RSV with α-tocopherol analogue in micelles and liposomes is in contrast to the previously reported lack of synergy in non-polar solvents; however, the increased persistency of tocopheroxyl radicals in dispersed lipid/water systems and proximal localization of both antioxidants greatly facilitate the possible recovery of α-TOH by RSV
dc.affiliationUniwersytet Warszawski
dc.contributor.authorLitwinienko, Grzegorz
dc.contributor.authorKonopko, Adrian
dc.date.accessioned2024-01-26T11:19:15Z
dc.date.available2024-01-26T11:19:15Z
dc.date.copyright2021-11-29
dc.date.issued2022
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.versionFINAL_PUBLISHED
dc.description.volume87
dc.identifier.doi10.1021/ACS.JOC.1C01801
dc.identifier.issn0022-3263
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/124177
dc.identifier.weblinkhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.1c01801
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Organic Chemistry
dc.relation.pages1698-1709
dc.rightsCC-BY
dc.sciencecloudnosend
dc.titleUnexpected Role of pH and Microenvironment on the Antioxidant and Synergistic Activity of Resveratrol in Model Micellar and Liposomal Systems
dc.typeJournalArticle
dspace.entity.typePublication