Interaction of the chemopreventive agent resveratrol and its metabolite, piceatannol, with model membranes

Abstract

Resveratrol and piceatannol are plant-derived polyphenols possessing extremely wide range of biological activities such as cancer chemopreventive, cardio- and neuroprotective, antioxidant, anti-inflammatory, anticancer and lifespan extending properties. Despite great interest in these stilbenes, their interactions with lipid bilayers have not been extensively studied. In the present work, the interaction of both resveratrol and piceatannol with model membranes composed of phosphatidylcholine (DMPC and DPPC) was investigated by means of fluorescence spectroscopy, differential scanning calorimetry (DSC) and electron spin resonance spectroscopy (ESR). Generalized polarization of two fluorescent probes Laurdan and Prodan measured in pure lipid and lipid:stilbene mixtures revealed that resveratrol and piceatannol changed bilayer properties in both gel-like and liquid crystalline phase and interacted with lipid headgroup region of the membrane. These findings were corroborated by DSC experiments in which the stilbene-induced decrease of lipid melting temperature and transition cooperativity were recorded. Resveratrol and piceatannol restricted also the ESR-measured mobility of spin probes GluSIN18, 5DSA and 16DSA with nitroxide group localized at different depths. Since the most pronounced effect was exerted on the spin probe located near membrane surface, we concluded that also ESR results pointed to the preferential interaction of resveratrol and piceatannol with headgroup region of lipid bilayer.

Interaction of selected anthocyanins with erythrocytes and liposome membranes

“…The compounds also protect plants against fungi and pests, against freezing and overheating, properly controlling their internal osmotic pressure, and they are also able to chelate metals [1]. The interest in these natural antioxidants is nowadays very great, as they prevent many serious diseases, connected with oxidative stress caused, among others, by lipid peroxidation [2][3][4][5][6][7]. Anthocyanins exhibit many properties that are favorable to human health, such as immunostimulation, anticancer, antibacterial, and antiinflammatory activity.…”

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

“…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].…”

Piceatannol: A Potential Futuristic Natural Stilbene as Fetal Haemoglobin Inducer

“…Piceatannol is a natural polyphenol and a structural analogue of Anti-inflammatory activity Anti-inflammatory activity [25,38] Anti-oxidant activity Anti-oxidant activity [38,39] Anti-cancer activity Anti-cancer activity [40] Anti-leukaemic activity Anti-leukaemic activity [41] [ Data mentioned in literature and research work have stated that piceatannol is a better Anti-oxidant than resveratrol. It has been proved that piceatannol has better activities than resveratrol.…”