Structure-dependent interactions of polyphenols with a biomimetic membrane system

Abstract

Polyphenols are naturally-occurring compounds, reported to be biologically active, and through their interactions with cell membranes. Although association of the polyphenols with the bilayer has been reported, the detailed mechanism of interaction is not yet well elucidated. We report on spatio-temporal real-time membrane dynamics observed in the presence of polyphenols. Two distinct membrane dynamics, corresponding to the two classes of polyphenols used, were observed. Flavonoids (epi-gallocatechin-3-gallate, gallocatechin, theaflavin and theaflavin-3-gallate) caused lipid membrane aggregation and rigidification. As simple structural modification through opening of the aromatic C-ring into an olefin bond, present in trans-stilbenes (resveratrol and picead), completely changed the membrane properties, increasing fluidity and inducing fluctuation. There were differences in the membrane transformations within the same class of polyphenols. Structure-dependent classification of membrane dynamics may contribute to a better understanding of the physicochemical mechanism involved in the bioactivity of polyphenols. In general, an increase in the number of hydrophilic side chains (galloyl, hydroxyl, glucoside, gallate) increased the reactivity of the polyphenols. Most notable was the difference observed through a simple addition of the gallate group. Unraveling the importance of these polyphenols, at a functional group level further opens the key to tailored design of bioactive compounds as potential drug candidates.

Red Chicory (Cichorium intybus) Extract Rich in Anthocyanins: Chemical Stability, Antioxidant Activity, and Antiproliferative Activity In Vitro

“…Studies have shown that flavonoids carry hydrogen bonds with the polar heads of the cell membrane phospholipids; as the polarity increases, the flavonoid interaction becomes more intense. These interactions promote greater aggregation of the phospholipids, thus reducing the membrane fluidity parameter (Phan et al., ; Wu et al., ). As anthocyanins are high‐polarity flavonoids, evidenced by the hydrophilic characteristic of this subclass of compounds, erythrocytes are protected from hypotonic hemolysis by red chicory extracts.…”

The Effects of Trifolium pratense L. Sprouts’ Phenolic Compounds on Cell Growth and Migration of MDA-MB-231, MCF-7 and HUVEC Cells

“…Biochanin A is known as strong scavenger of ROS, activator of SOD (superoxide dismutase) enzyme activity and reducer of COX-2 expression [31]. However, there is growing evidence of polyphenols' reactions with nonpolar compounds present in the hydrophobic inner membrane layer [18,32,33]. Thus, the second way of protection of the cellular Control cells were not exposed to any compound but the vehicle; values are means ± standard deviations from at least three independent experiments; statistical significance was calculated versus control cells (untreated); *** p ≤ 0.001.…”

Polytrichum commune L.ex Hedw ethyl acetate extract-triggered perturbations in intracellular Ca2+ homeostasis regulates mitochondrial-dependent apoptosis

“…And we speculate that the plasma membrane damage induced by PC-EEF may relate 25 to the interactions between PC-EEF with the membrane system (Phan et al, 2014).…”