The interaction of flavonols with membrane components: potential effect on antioxidant activity

Show simple item record Saha, Sarmistha Panieri, Emiliano Suzen, Sibel Saso, Luciano 2020-03-07T14:28:09Z 2020-03-07T14:28:09Z 2020-02
dc.identifier.citation Saha, Sarmistha; Panieri, Emiliano; Suzen, Sibel; Saso, Luciano"The interaction of flavonols with membrane components: potential effect on antioxidant activity", The Journal of Membrane Biology, DOI: 10.1007/s00232-019-00105-1, vol. 253, no. 1, pp. 57�71, Feb. 2020. en_US
dc.identifier.issn 0022-2631
dc.identifier.issn 1432-1424
dc.description.abstract Flavonols are the most widely distributed class of dietary flavonoids with a wide range of pharmacological properties due to their potent lipid peroxidation inhibition activity. The permeability and orientation of these compounds in lipid bilayers can provide an understanding of their antioxidant and lipid-peroxidation inhibition activity based on their structures at the molecular level. For this purpose, we studied antioxidant activity and atomic-scale molecular dynamics simulations of 3-hydroxyflavone (fisetin), 5-hydroxyflavone (apigenin) and 3,5-hydroxyflavone (morin) in palmitoyloleylphosphatidylcholine (POPC) membrane models with 0 mol% and 40 mol% cholesterol concentration. In pure POPC bilayer with 0 mol% cholesterol concentration, the flavonols penetrated into bilayer with lowest free energy profiles, however, incorporation of 40% cholesterol concentration reduced the permeability of the flavonols. Higher cholesterol concentrations in the POPC lipid bilayer resulted in an increase of the bilayer thickness and corresponding decrease in the area per lipid which rationalizes the reduced partitioning of flavonols due to cholesterol. In the presence of cholesterol, the flavonols reside at the polar interfacial region of the lipid bilayer to form higher H-bonding interactions with cholesterol molecules in addition to water and lipid oxygens. Among all the selected flavonols, morin showed the highest affinity which was driven by the hydrophobic effect as also depicted by ITC (Isothermal titration calorimetry) experiments and thus, more efficient antioxidant in scavenging superoxide, nitric oxide radicals as well as lipid peroxyl radicals. Furthermore, our simulations also confirmed that the permeability of compounds is sensitive towards the cholesterol content in the membrane.
dc.description.statementofresponsibility by Sarmistha Saha, Emiliano Panieri, Sibel Suzen and Luciano Saso
dc.format.extent vol. 253, no. 1, pp. 57�71
dc.language.iso en_US en_US
dc.publisher Springer Verlag en_US
dc.title The interaction of flavonols with membrane components: potential effect on antioxidant activity en_US
dc.type Article en_US
dc.relation.journal The Journal of Membrane Biology

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