Interaction of the antioxidant flavonoid quercetin with planar lipid bilayers

Movileanu, Liviu; Neagoe, Ioana; Flonta, Maria-Luiza

doi:10.1016/s0378-5173(00)00503-2

Cited by 136 publications

(97 citation statements)

References 32 publications

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“…Similarly, the embedding of quercetin in bilayers depends on the pH of the media. At acidic pH, quercetin is deeply embedded in planar lipid bilayers (Movileanu et al 2000), while at physiological pH it interacts with the polar head groups at the water -lipid interface (Terao et al 1994, Movileanu et al 2000, PawlikowskaPawlega et al 2003. The flavanones, naringenin and rutin, and a series of isoflavones partition in the hydrophobic portion of liposome bilayers, inducing the loss of membrane fluidity (Arora et al 2000).…”

Section: Partitioning Of Flavonoids In the Hydrophobic Portion Of Memmentioning

confidence: 99%

Flavonoid‐membrane Interactions: A Protective Role of Flavonoids at the Membrane Surface?

Oteiza

Erlejman

Verstraeten

et al. 2005

Journal of Immunology Research

324

186

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Flavonoids can exert beneficial health effects through multiple mechanisms. In this paper, we address the important, although not fully understood, capacity of flavonoids to interact with cell membranes. The interactions of polyphenols with bilayers include: (a) the partition of the more non-polar compounds in the hydrophobic interior of the membrane, and (b) the formation of hydrogen bonds between the polar head groups of lipids and the more hydrophilic flavonoids at the membrane interface. The consequences of these interactions are discussed. The induction of changes in membrane physical properties can affect the rates of membrane lipid and protein oxidation. The partition of certain flavonoids in the hydrophobic core can result in a chain breaking antioxidant activity. We suggest that interactions of polyphenols at the surface of bilayers through hydrogen bonding, can act to reduce the access of deleterious molecules (i.e. oxidants), thus protecting the structure and function of membranes.

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Section: Partitioning Of Flavonoids In the Hydrophobic Portion Of Memmentioning

confidence: 99%

Flavonoid‐membrane Interactions: A Protective Role of Flavonoids at the Membrane Surface?

Oteiza

Erlejman

Verstraeten

et al. 2005

Journal of Immunology Research

324

186

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“…The current view for the localization of the three 2 compounds correlates well with most other existing studies, which suggest localization of 3 flavonoids between the boundary of the lipid/water interface and the upper half of the 4 hydrocarbon chain region. 52,53,54,55,56,57 Notwithstanding this view, some studies suggest that the 5 flavonoids partition into the hydrophobic region of the membrane. 58,59 An NMR study has 6…”

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confidence: 99%

“…54 A FTIR study suggested the same explanation 8 for quercetin. 55 Movileanu et al, 53 proposed a pH dependent insertion of quercetin within 9 membranes. Quercetin molecules inserted between the polar head groups at alkaline pH, with 10 deeper localization at acidic pH, due to intercalation of quercetin molecules between the acyl 11 chains.…”

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confidence: 99%

Experimental Modeling of Flavonoid–Biomembrane Interactions

Sanver

Murray²,

Sadeghpour³

et al. 2016

Langmuir

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and visualization of the surface with BAM revealed a pronounced monolayer stabilization effect 10 with both quercetin and tiliroside, whereas rutin disrupted the monolayer structure rendering the 11 surface entirely smooth. SAXS showed a monotonous membrane thinning for all compounds 12 studied associated with an increase in the root mean square fluctuations of the membrane. Rutin, 13 quercetin and tiliroside decreased the bilayer thickness of DOPC by ~0.45 Å, 0.8 Å, and 1.1 Å at 14 6 mol %, respectively. In addition to the novelty of using lipid monolayers to systematically 15 characterize the structure activity relationship (SAR) of a variety of flavonoids; this is the first 16 report investigating the effect of tiliroside with biomimetic membrane models. All the flavonoids 17 studied are believed to be localized in the lipid/water interface region. Both this localization and 18 the membrane perturbations have implications for their therapeutic activity.

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“…The interaction of quercetin with planar lipid bilayers has been studied in some detail [41]. Quercetin as well as naringenin [42] have an affinity for the hydrophobic membranes and some of their biological activities may be explained by this interaction.…”

Section: Discussionmentioning

confidence: 99%

Toxicity and Cell Cycle Effects of Synthetic 8-Prenylnaringenin and Derivatives in Human Cells

Tokalov¹,

Henker²,

Schwab

et al. 2004

Pharmacology

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The estrogenic flavanone rac-8-prenylnaringenin (8-PN) and 3 derivatives (rac-7-(O-prenyl)naringenin-4′-acetate (7-O-PN), rac-5-(O-prenyl)naringenin-4′,7-diacetate (5-O-PN), and rac-6-(1,1-dimethylallyl)naringenin (6-DMAN) were prepared by chemical synthesis and analyzed with respect to their toxicity and possible cell cycle effects in human acute myeloid leukemia (HL-60) cells. With the exception of 5-O-PN, all the other naringenins showed only weak toxic effects at concentrations below 50 µmol/l. A cell cycle analysis over several cell generations up to 4 days was carried out using the fluorescent dye carboxyfluorescein diacetate N-succinimidyl ester (CFSE) followed by propidium iodide (PI) staining at the end of the experiment. The well-studied flavonol quercetin was included in the analysis as a reference substance. All flavonoids affected cell proliferation, but the extent and the resulting changes in the proliferation pattern were specific for each substance. In contrast to the radical scavenging activity of quercetin, the tested flavanones showed no anti-oxidative properties using several different test systems. Similarly, the mitochondrial membrane potential (ΔΨm) was hardly effected by these compounds, while both menadione and quercetin strongly reduced the potential after 1 h of treatment. The reported chemical modification of interesting lead substances (like the strongly estrogenic 8-PN) presents a promising approach to modulate the properties of a relevant substance in a pharmacologically desirable way. The low toxicity and weak cytostatic properties of the tested naringenin derivatives is encouraging for further studies on known naringenin target molecules.

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Interaction of the antioxidant flavonoid quercetin with planar lipid bilayers

Cited by 136 publications

References 32 publications

Flavonoid‐membrane Interactions: A Protective Role of Flavonoids at the Membrane Surface?

Flavonoid‐membrane Interactions: A Protective Role of Flavonoids at the Membrane Surface?

Experimental Modeling of Flavonoid–Biomembrane Interactions

Toxicity and Cell Cycle Effects of Synthetic 8-Prenylnaringenin and Derivatives in Human Cells

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