Interaction of selected anthocyanins with erythrocytes and liposome membranes

Abstract

Anthocyanins are one of the main flavonoid groups. They are responsible for, e.g., the color of plants and have antioxidant features and a wide spectrum of medical activity. The subject of the study was the following compounds that belong to the anthocyanins and which can be found, e.g., in strawberries and chokeberries: callistephin chloride (pelargonidin-3-O-glucoside chloride) and ideain chloride (cyanidin-3-O-galactoside chloride). The aim of the study was to determine the compounds' antioxidant activity towards the erythrocyte membrane and changes incurred by the tested anthocyanins in the lipid phase of the erythrocyte membrane, in liposomes composed of erythrocyte lipids and in DPPC, DPPC/cholesterol and egg lecithin liposomes. In particular, we studied the effect of the two selected anthocyanins on red blood cell morphology, on packing order in the lipid hydrophilic phase, on fluidity of the hydrophobic phase, as well as on the temperature of phase transition in DPPC and DPPC/cholesterol liposomes. Fluorimetry with the Laurdan and Prodan probes indicated increased packing density in the hydrophilic phase of the membrane in the presence of anthocyanins. Using the fluorescence probes DPH and TMA-DPH, no effect was noted inside the hydrophobic phase of the membrane, as the lipid bilayer fluidity was not modified. The compounds slightly lowered the phase transition temperature of phosphatidylcholine liposomes. The study has shown that both anthocyanins are incorporated into the outer region of the erythrocyte membrane, affecting its shape and lipid packing order, which is reflected in the increasing number of echinocytes. The investigation proved that the compounds penetrate only the outer part of the external lipid layer of liposomes composed of erythrocyte lipids, DPPC, DPPC/cholesterol and egg lecithin lipids, changing its packing order. Fluorimetry studies with DPH-PA proved that the tested anthocyanins are very effective antioxidants. The antioxidant activity of the compounds was comparable with the activity of Trolox ® .

Effect of chlorogenic acid on the phase transition in phospholipid and phospholipid/cholesterol membranes

“…In conclusion, one can infer that the protective action of CGA with respect to biological membranes depends on the extent of its incorporation in the hydrophilic part of the membrane, which is in agreement with the results we obtained for polyphenolic compounds [34].…”

“…Using DSC, we monitored thermal parameters which included the temperatures of the pretransition (T p ) and the main transition peak (T m ), the half-width (DT 1/2 ), and change of the enthalpy (DH) of the main transition of lipids. We used model systems of dimyristoylphosphatidylcholines, dipalmitoylphosphatidylcholines, and dipalmitoylphosphatidylcholines with cholesterol, such as multilamellar or unilamellar liposomes, as a very good platform to elucidate the effect of CGA on some physical properties of lipid membranes [18,19,[31][32][33][34][35].…”

Physicochemical composition and antioxidant activity of several pomegranate (Punica granatum L.) cultivars grown in Spain

“…Concerning cyanidin-3-O-glucoside chloride, compound that increases the fibrinolytic potency of vascular endothelial cells and may prevent thrombus formation, the Wonderful 1 cultivar was the one with the highest content (27.6 mg/l), closely followed by Wonderful 2 (26.2 mg/l). Mollar de Elche presented the highest content of pelargonidin-3-Oglucoside chloride (12.9 mg/l) that is an anthocyanin able to protect successfully membrane lipids against oxidation induced by both chemical such as AAPH (2,2′-azobis(2-methylpropionamidine) dihydrochloride) radicals and physical (UVC radiation) agents [71]. For both compounds, Valenciana and Cis 127 were the cultivars that again presented the lowest concentrations, in line with the results obtained for the monomeric anthocyanin pigment contents (Table 3).…”

Influence of cytotoxic butyltin complexes with 2-sulfobenzoic acid on the thermotropic phase behavior of lipid model membranes

“…GI \ ), where I II and I \ are fluorescence intensities observed in the direction parallel and perpendicular to the polarization direction of the exciting wave. G is an apparatus constant dependent on the emission wavelength [20]. Changes in the polar group packing arrangement of the hydrophilic part of the membrane were investigated using Laurdan and Prodan probes, on the basis of generalized polarization (GP), and were calculated with the formula GP = (I g -I l )/(I g ?…”