Interaction between Mimic Lipid Membranes and Acylated and Nonacylated Cyanidin and Its Bioactivity.
We investigated the effects of acylated cyanidin-3-O-β-(6″-O-E-p-coumaroyl-sambubioside)-5-O-β-glucoside (C3-cs-5G) and nonacylated cyanidin, cyanidin-3,5-di-O-β-glucoside (C3,5G) and cyanidin-3-O-β-glucoside (C3G), on cell-mimic membranes (MM) that reflected the membrane lipid composition of tumor cells. The relationship between structural derivatives of cyanidin (Cy-d), membrane interactivity, their antioxidant activity, and interaction with albumin were characterized. Studies showed that Cy-d caused an increase in packing order mainly in the hydrophilic region of the membranes. Cy-d have shown high antioxidant activity against liposome oxidation induced by AAPH and ability to bind to albumin through a static quenching mechanism. The results showed that glycosylation number and the presence of aromatic acid attached to sugars affected the membrane properties, according to the sequence C3-cs-5G > C3,5G > C3G. It can be stated that Cy-d in the process of interaction with MM caused a rigidifying effect, which is fundamental for understanding their anticancer and antioxidant activity and is one of the possible pharmaceutical mechanisms.
Department of Physics and Biophysics, Wrocław University of Environmental and Life Sciences , C.K. Norwida 25, 50-375 Wrocław, Poland.
Paulina
P
Strugała
Department of Physics and Biophysics, Wrocław University of Environmental and Life Sciences , C.K. Norwida 25, 50-375 Wrocław, Poland.
Anna
A
Dudra
Department of Physics and Biophysics, Wrocław University of Environmental and Life Sciences , C.K. Norwida 25, 50-375 Wrocław, Poland.
Janina
J
Gabrielska
D000215:Acylation; D000872:Anthocyanins / Q000737:chemistry*; D000975:Antioxidants / Q000737:chemistry; D002462:Cell Membrane; D005453:Fluorescence; D005960:Glucosides / Q000737:chemistry*; D006031:Glycosylation; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008051:Lipid Bilayers / Q000737:chemistry; D008563:Membrane Lipids / Q000737:chemistry*; D015394:Molecular Structure; D009369:Neoplasms; D012709:Serum Albumin / Q000737:chemistry
D000872:Anthocyanins; D000975:Antioxidants; D005960:Glucosides; D008051:Lipid Bilayers; D008563:Membrane Lipids; D012709:Serum Albumin; C462279:cyanidin-3-O-beta-glucopyranoside; C017154:cyanidin
acylated cyanidin; anthocyanins; antioxidants activity; human albumin; lipid membrane