Novel O-Methylglucoside Derivatives of Flavanone in Interaction with Model Membrane and Transferrin

Abstract

Flavonoids were biotransformed using various microorganisms, in order to obtain new compounds with potentially high biological activity. The aim of this work was to determine and compare the biological activity of four novel 6-methylflavanone O-methylglucosides. The tested compounds have the same flavonoid core structure and an attached O-methylglucose and hydroxyl group at different positions of ring A or B. The studies on their biological activity were conducted in relation to phosphatidylcholine membrane, erythrocytes and their membrane, and with human transferrin. These studies determined the compounds’ toxicity and their impact on the physical properties of the membranes. Furthermore, the binding ability of the compounds to holo-transferrin was investigated. The obtained results indicate that used compounds bind to erythrocytes, change their shape and decrease osmotic fragility but do not disrupt the membrane structure. Furthermore, the used compounds ordered the area of the polar heads of lipids and increased membrane fluidity. However, the results indicate the binding of these compounds in the hydrophilic region of the membranes, like other flavonoid glycosides. The used flavanones formed complexes with transferrin without inducing conformational changes in the protein’s structure. The relationship between their molecular structure and biological activity was discussed.