Abstract
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.
Highlights
IntroductionI.e., without sugar substituents, belongs to the anthocyanins and occurs in Nature very rarely
Cyanidin as an aglycone, i.e., without sugar substituents, belongs to the anthocyanins and occurs in Nature very rarely
There is a lack of studies comparing the activity of cyanidin and its glycosides, containing various sugar substituents, that would determine the relationship between the structure and activity of these compounds in relation to lipid bilayer
Summary
I.e., without sugar substituents, belongs to the anthocyanins and occurs in Nature very rarely. The physicochemical properties of cyanidin and its glycosides depend on the number, type and position of sugars in their structures, which determine their biological activity. There is a lack of studies comparing the activity of cyanidin and its glycosides, containing various sugar substituents, that would determine the relationship between the structure and activity of these compounds in relation to lipid bilayer. This type of basic research is necessary to determine the molecular mechanism responsible for the biological activity of the compounds, because the lipid-protein membrane constitute the first barrier, which determines the interactions of different substances with organisms. On the basis of the obtained results the impact of the type and number of sugar substituent on biological activity of cyanidin was determined
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