Department of Physics and Biophysics, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.
J. Heyrovsky Institute of Physical Chemistry, Academy of Science of the Czech Republic, Dolejškova 2155/3, Prague 8, 182 23, Czech Republic.
Molecules. 2018 Oct 25;23(11):2771. doi: 10.3390/molecules23112771.
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.
矢车菊素及其 O-糖苷在植物中有许多重要的生理功能，对人类健康有益。它们的生物活性并不完全清楚，这取决于分子的结构，特别是取决于糖取代基的数量和类型。因此，在这项研究中，确定了花色苷/花色素与脂质双层相互作用的详细结构-活性关系（SAR）。基于它们的抗氧化活性以及它们对脂质囊泡大小和 Zeta 电位、脂质酰链的流动性和有序性的变化，评估了糖取代基数量和类型对化合物生物活性的影响。研究结果表明，3-O-糖苷化完全改变了矢车菊素与脂质双层的相互作用。含有单糖的 3-O-糖苷比含有二糖的糖苷更能引起脂质膜物理性质的变化。额外糖的存在显著降低了糖苷与模型脂质膜的相互作用。此外，O-糖苷化改变了矢车菊素清除自由基的能力。这种改变取决于自由基的类型和用于测定它们的方法的灵敏度。
