Study of Resveratrol’s Interaction with Planar Lipid Models: Insights into Its Location in Lipid Bilayers

Meleleo, Daniela

doi:10.3390/membranes11020132

Cited by 16 publications

(14 citation statements)

References 61 publications

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“…For example, based on molecular dynamics simulation, diarylheptanoid curcumin stays in the lipid tail region, close to the interface of the lipid head and lipid tail, most probably in parallel orientation relative to the lipid bilayer [ 29 ]. Trans-stilbene resveratrol is mainly located in a deeper region of the membrane, interacting with the lipid tails [ 35 , 37 , 118 , 119 ], but some studies support its location close to the polar headgroups [ 120 ]. Furthermore, simple phenolic oleuropein aglycone is known to be located between the hydrocarbon acyl chains of the phospholipids, although its exact locations and molecular interactions are different in different lipid systems: In the POPC/cholesterol systems, it is closer to the membrane surface, whereas it penetrates more deeply in POPC/1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol (POPG)/cholesterol systems [ 121 ].…”

Section: Understanding the Polyphenol–lipid Interactionsmentioning

confidence: 99%

Insights into Polyphenol–Lipid Interactions: Chemical Methods, Molecular Aspects and Their Effects on Membrane Structures

Karonen

2022

Plants

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Plant polyphenols have many potential applications, for example, in the fields of chemical ecology and human and animal health and nutrition. These biological benefits are related to their bioavailability, bioaccessibility and interactions with other biomolecules, such as proteins, lipids, fibers and amino acids. Polyphenol–protein interactions are well-studied, but less is known about their interactions with lipids and cell membranes. However, the affinity of polyphenols for lipid bilayers partially determines their biological activity and is also important from the usability perspective. The polyphenol–lipid interactions can be studied with several chemical tools including, among others, partition coefficient measurements, calorimetric methods, spectroscopic techniques and molecular dynamics simulation. Polyphenols can variably interact with and penetrate lipid bilayers depending on the structures and concentrations of the polyphenols, the compositions of the lipids and the ambient conditions and factors. Polyphenol penetrating the lipid bilayer can perturb and cause changes in its structure and biophysical properties. The current studies have used structurally different polyphenols, diverse model lipids and various measuring techniques. This approach provides detailed information on polyphenol–lipid interactions, but there is much variability, and the results may even be contradictory, for example, in relation to the locations and orientations of the polyphenols in the lipid bilayers. Nevertheless, by using well-characterized model polyphenols and lipids systematically and combining the results obtained with several techniques within a study, it is possible to create a good overall picture of these fascinating interactions.

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Section: Understanding the Polyphenol–lipid Interactionsmentioning

confidence: 99%

Insights into Polyphenol–Lipid Interactions: Chemical Methods, Molecular Aspects and Their Effects on Membrane Structures

Karonen

2022

Plants

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“…Resveratrol is poorly soluble in water, thus explaining its high affinity plasma membrane. While some studies show a location of Resv around the polar head region of lipids [38][39][40], others indicate a deeper positioning around hydrophobic fatty acid tails of the lipid bilayer [25,26,[41][42][43]. Ghellinck at al., f…”

Section: Discussionmentioning

confidence: 99%

Structural Changes Induced by Resveratrol in Monounsaturated and Polyunsaturated Phosphatidylcholine-Enriched Model Membranes

Hazarosova,

Momchilova,

Vitkova

et al. 2023

Membranes

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Resveratrol (Resv) is considered to exert a beneficial impact due to its radical scavenger, anti-microbial and anti-inflammatory properties through several mechanisms that could include its interaction with the cell plasma membrane. To address this issue, we investigated the influence of Resv on membrane lipid order and organization in large unilamellar vesicles composed of different lipids and ratios. The studied lipid membrane models were composed of phosphatidylcholine (PC) species (either palmitoyl-docosahexaenoyl phosphatidylcholine (PDPC) or palmitoyl-oleoyl phosphatidylcholine (POPC)), sphingomyelin (SM) and cholesterol (Chol). This study found that the addition of Resv resulted in complex membrane reorganization depending on the degree of fatty acid unsaturation at the sn-2 position, and the Lipid/Resv and SM/Chol ratios. Resv rigidified POPC-containing membranes and increased liquid-ordered (Lo) domain formation in 40/40/20 POPC/SM/Chol mixtures as this increase was lower at a 33/33/34 ratio. In contrast, Resv interacted with PDPC/SM/Chol mixtures in a bimodal manner by fluidizing/rigidifying the membranes in a dose-dependent way. Lo domain formation upon Resv addition occurred via the following bimodal mode of action: Lo domain size increased at low Resv concentrations; then, Lo domain size decreased at higher ones. To account for the variable effect of Resv, we suggest that it may act as a “spacer” at low doses, with a transition to a more “filler” position in the lipid bulk. We hypothesize that one of the roles of Resv is to tune the lipid order and organization of cell plasma membranes, which is closely linked to important cell functions such as membrane sorting and trafficking.

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“…The electrophysiological method of PLMs is a useful tool for obtaining information on the molecular mechanism of chemicals that interact with membrane lipids. Many substances (proteins, peptides, or drugs) that are active at the membrane interface promote ionic current flow across the membrane (i.e., increase membrane conductance) when they incorporate into the lipid bilayer and form conductive units [ 31 , 32 , 33 , 34 , 35 , 36 , 37 ]. Several pore models formed by different interface active compounds have been proposed and the different characteristics of the current signals have been associated with the different models, as reported by Bertrand et al [ 38 ].…”

Section: Discussionmentioning

confidence: 99%

Interaction of Quercetin, Cyanidin, and Their O-Glucosides with Planar Lipid Models: Implications for Their Biological Effects

et al. 2023

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Flavonoids are specialized metabolites produced by plants, as free aglycones or as glycosylated derivatives, which are particularly endowed with a variety of beneficial health properties. The antioxidant, anti-inflammatory, antimicrobial, anticancer, antifungal, antiviral, anti-Alzheimer’s, anti-obesity, antidiabetic, and antihypertensive effects of flavonoids are now known. These bioactive phytochemicals have been shown to act on different molecular targets in cells including the plasma membrane. Due to their polyhydroxylated structure, lipophilicity, and planar conformation, they can either bind at the bilayer interface or interact with the hydrophobic fatty acid tails of the membrane. The interaction of quercetin, cyanidin, and their O-glucosides with planar lipid membranes (PLMs) similar in composition to those of the intestine was monitored using an electrophysiological approach. The obtained results show that the tested flavonoids interact with PLM and form conductive units. The modality of interaction with the lipids of the bilayer and the alteration of the biophysical parameters of PLMs induced by the tested substances provided information on their location in the membrane, helping to elucidate the mechanism of action which underlies some pharmacological properties of flavonoids. To our knowledge, the interaction of quercetin, cyanidin, and their O-glucosides with PLM surrogates of the intestinal membrane has never been previously monitored.

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Study of Resveratrol’s Interaction with Planar Lipid Models: Insights into Its Location in Lipid Bilayers

Cited by 16 publications

References 61 publications

Insights into Polyphenol–Lipid Interactions: Chemical Methods, Molecular Aspects and Their Effects on Membrane Structures

Insights into Polyphenol–Lipid Interactions: Chemical Methods, Molecular Aspects and Their Effects on Membrane Structures

Structural Changes Induced by Resveratrol in Monounsaturated and Polyunsaturated Phosphatidylcholine-Enriched Model Membranes

Interaction of Quercetin, Cyanidin, and Their O-Glucosides with Planar Lipid Models: Implications for Their Biological Effects

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