Effect of Resveratrol-Related Stilbenoids on Biomembrane Models

Abstract

The interactions of the two resveratrol analogues 2-hydroxy-3,5,3',5'-tetramethoxystilbene (4) and 2-hydroxy-3,5,3',4'-tetramethoxystilbene (5) with model biomembranes were studied. The aim of this investigation was to highlight possible differences in the interactions with such biomembranes related to the minimal structural differences between these isomeric stilbenoids. In particular, different experiments on stilbenoid/biomembrane model systems using both differential scanning calorimetry (DSC) and Langmuir-Blodgett techniques were carried out to evaluate stilbenoid/multilamellar vesicle and stilbenoid/phospholipid monolayer interactions, respectively. Dimyristoylphosphatidylcholine was used as constituent of the biomembrane models and permitted the experiments to be carried out at 37 °C, close to body temperature. Kinetic studies were also run by DSC to evaluate the uptake of the resveratrol derivatives by the biomembrane model in an aqueous medium and when transported by a lipophilic carrier. The results indicated that both of the resveratrol analogues influenced the behavior of multilamellar vesicles and monolayers, biomembrane models, with 4 producing a larger effect than 5. These results are useful for better understanding the mechanism of action of these compounds. Moreover, the kinetic results could be of importance for future design of lipophilic delivery systems for these stilbenoids.

Interaction of β-caryophyllene and β-caryophyllene oxide with phospholipid bilayers: Differential scanning calorimetry study

“…The non perturbative technique of differential scanning calorimetry (DSC) was applied for measuring the effect of the molecules on the thermotropic behaviour of DMPC MLV [21,22]. Experiments were also carried out in order to characterize the interference of the aqueous or lipid medium with the uptake of the test substances through the biomembrane model [23].…”

Deciphering the Peculiar Behavior of β-Lapachone in Lipid Monolayers and Bilayers

“…Even in the absence of such an interfacial effect, hydrophobic/amphiphilic compounds may affect phospholipid monolayers, exhibiting characteristic π– A profiles, as seen with resveratrol or 7-ethyl-10-hydroxy-campthothecin . A similar effect was thus investigated for β-Lap at 3.5 mol % mixed with various lipids classically used in liposome preparation, namely, POPC, , DOPC, , and DPPC, ,, with or without cholesterol.…”

Resveratrol-Related Polymethoxystilbene Glycosides: Synthesis, Antiproliferative Activity, and Glycosidase Inhibition

“…The aqueous phase was extracted with CHCl 3 (3 × 8 mL); the combined organic phases were washed with H 2 O (3 × 16 mL), dried over Na 2 SO 4 , filtered, and evaporated to dryness. The crude extract was purified by column chromatography with RP-18 silica gel with a gradient of CH 3 CN in H 2 O (from 10% to 50%), affording 21 (0.0087 g, 43%): amorphous powder; R f (TLC) = 0.16 (4% CH 3 OH/CHCl 3 ); (22). Compound 19 (0.0162 g, 0.051 mmol) was dissolved in MeOH/H 2 O (45:55, 7.5 mL), and the solution was stirred with K 2 CO 3 (0.0714 g, 0.517 mmol) at room temperature for 15 min.…”

“…Polymethoxystilbenes are frequently much more antiproliferative than resveratrol , and show other promising properties such as antiangiogenic activity and VEGF inhibition, ,, inhibition of NF-kB activation, and inhibition of multidrug resistance (MDR) of tumor cells . Further studies indicate that 2 and other polymethoxystilbenes are able to interact with biomembrane models − and have a higher bioavailability than resveratrol. − Among the methoxylated stilbenes and related compounds, some cis -isomers have shown higher antiproliferative or antimetastatic activity than their trans -isomers, but they are prone to isomerization during storage and administration and during metabolism in liver microsomes …”