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The Impact of O-Glycosylation on Cyanidin Interaction with POPC Membranes: Structure-Activity Relationship
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SYSNO ASEP 0499172 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title The Impact of O-Glycosylation on Cyanidin Interaction with POPC Membranes: Structure-Activity Relationship Author(s) Cyboran-Mikołajczyk, S. (PL)
Jurkiewicz, Piotr (UFCH-W) RID, ORCID
Hof, Martin (UFCH-W) RID, ORCID
Kleszczyńska, H. (PL)Article number 2771 Source Title Molecules. - : MDPI
Roč. 23, č. 11 (2018)Number of pages 15 s. Language eng - English Country CH - Switzerland Keywords fluorescence depolarization ; anthocyanins ; flavonoids ; order ; chemistry ; liposomes ; laurdan ; probes ; dppc Subject RIV CF - Physical ; Theoretical Chemistry OECD category Physical chemistry R&D Projects GBP208/12/G016 GA ČR - Czech Science Foundation (CSF) Method of publishing Open access Institutional support UFCH-W - RVO:61388955 UT WOS 000451641900043 EID SCOPUS 85055591164 DOI 10.3390/molecules23112771 Annotation Cyanidin and its O-glycosides have many important physiological functions in plants and beneficial effects on human health. Their biological activity is not entirely clear and depends on the structure of the molecule, in particular, on the number and type of sugar substituents. Therefore, in this study the detailed structure-activity relationship (SARs) of the anthocyanins/anthocyanidins in relation to their interactions with lipid bilayer was determined. On the basis of their antioxidant activity and the changes induced by them in size and Zeta potential of lipid vesicles, and mobility and order of lipid acyl chains, the impact of the number and type of sugar substituents on the biological activity of the compounds was evaluated. The obtained results have shown, that 3-O-glycosylation changes the interaction of cyanidin with lipid bilayer entirely. The 3-O-glycosides containing a monosaccharide induces greater changes in physical properties of the lipid membrane than those containing disaccharides. The presence of additional sugar significantly reduces glycoside interaction with model lipid membrane. Furthermore, O-glycosylation alters the ability of cyanidin to scavenge free radicals. This alteration depends on the type of free radicals and the sensitivity of the method used for their determination. Workplace J. Heyrovsky Institute of Physical Chemistry Contact Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Year of Publishing 2019
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