Differential interaction of Sophora isoflavonoids with lipid bilayers

Hendrich, Andrzej B.; Malon, Rafal; Poła, Andrzej; Shirataki, Yoshiaki; Motohashi, Noboru; Michalak, Krystyna

doi:10.1016/s0928-0987(02)00106-9

Cited by 66 publications

(56 citation statements)

References 31 publications

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“…Pretransition is very sensitive to any kind of perturbation, not only by compounds that penetrate the lipid bilayer but also by cosmotropic substances. Compounds that incorporate into the polar-unpolar region of the lipid bilayer abolish the DPPC pretransition even when used at low concentrations [33]. Additionally, the greater overall enthalpy suggests a lower ability of CGA to disrupt the bilayer structure (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…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].…”

Section: Introductionmentioning

confidence: 99%

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

Pruchnik

Bonarska-Kujawa

Kleszczyńska

2014

J Therm Anal Calorim

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Chlorogenic acid (CGA) is present in many plants, especially in green coffee, dry plums, and bilberries. It is an important bioactive polyphenol. Studies showed that CGA has an antioxidative, bacteriostatic, anticancer, antiviral, and anti-inflammatory activity. Despite great interest in this compound, its interaction with the lipid model membrane has not yet been investigated. To better understand the relationship between the biological activity of CGA and its interaction with biological membranes, the thermotropic behavior of model lipid membranes was investigated. The effect of CGA on the model lipid membrane, specifically on the lipid bilayer phase transitions, was examined by the combined methods: differential scanning calorimetry and fluorescence spectroscopy. In particular, the degree of packing order of the hydrophilic phase of the lipid bilayer was determined using the fluorimetric method with Laurdan and Prodan probes, while the fluorescence anisotropy of the hydrophobic phase with the DPH and TMA-DPH probes. The results of the study show that CGA incorporates mainly into the hydrophilic part of membrane, changing the packing order of the polar heads of lipids. No significant changes were recorded in membrane fluidity of the hydrophobic membrane region, for the fluorescence anisotropy practically did not change. One can thus infer that CGA does not penetrate deep into the hydrophobic area of the membrane.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Pruchnik

Bonarska-Kujawa

Kleszczyńska

2014

J Therm Anal Calorim

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“…Also, other flavonoids (naringenin, quercetin and hesperetin) [61] and isoflavonoids [62] were previously observed to exert similar effects on the thermotropic properties of DPPC bilayers. Such a localization of flavonoids inside the membrane could be deduced on the basis of their chemical structures: a hydrophobic ring system facilitated interaction with lipid acyl chains, while hydroxyl groups could interact with the polar headgroup region of the bilayer.…”

Section: Discussionmentioning

confidence: 79%

Perturbation of the lipid phase of a membrane is not involved in the modulation of MRP1 transport activity by flavonoids

Wesołowska

Hendrich

Łania-Pietrzak

et al. 2009

Cellular and Molecular Biology Letters

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The expression of transmembrane transporter multidrug resistance-associated protein 1 (MRP1) confers the multidrug-resistant phenotype (MDR) on cancer cells. Since the activity of the other MDR transporter, P-glycoprotein, is sensitive to membrane perturbation, we aimed to check whether the changes in lipid bilayer properties induced by flavones (apigenin, acacetin) and flavonols (morin, myricetin) were related to their MRP1 inhibitory activity. All the flavonoids inhibited the efflux of MRP1 fluorescent substrate from human erythrocytes and breast cancer cells. Morin was also found to stimulate the ATPase activity of erythrocyte ghosts. All flavonoids intercalated into phosphatidylcholine bilayers as judged by differential scanning calorimetry and fluorescence spectroscopy with the use of two carbocyanine dyes. The model of an intramembrane localization for flavones and flavonols was proposed. No clear relationship was found between the membrane-perturbing activity of flavonoids and their potency to inhibit MRP1. We concluded that mechanisms other than perturbation of the lipid phase of membranes were responsible for inhibition of MRP1 by the flavonoids.

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“…Therefore, alteration of lipid bilayer properties may result not only in antioxidant action of flavonoids but also in affecting the activity of integral proteins and hence influence transport and other membrane-related processes [28][29][30][31][32][33][34][35][36][37][38][39][40][41]. The ability of polyphenols to penetrate into lipid bilayers is undoubtedly crucial to the protection against oxidation [42].…”

Section: Introductionmentioning

confidence: 99%

“…As a model, we used liposome multi-and unilamellar vesicles formed of dimyristoylphosphatidylcholine (DMPC). This model is very well described in the literature and is known for allowing relatively easy analysis of changes in physical parameters of membrane induced by additional components [28,29,[34][35][36].…”

Section: Introductionmentioning

confidence: 99%

Interaction of skullcap (Scutellaria baicalensis Georgi) and buckwheat (Fagopyrum esculentum Moench) extracts with lipid bilayers

Pruchnik

Włoch

Żyłka

et al. 2015

J Therm Anal Calorim

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In this paper, we report the effect of skullcap (Scutellaria baicalensis Georgi) root (SR) and buckwheat (Fagopyrum esculentum Moench) husk and stalk (BH and BS) extracts on lipid organization and fluidity of model membranes, examined by monitoring of the thermotropic phase transition of dimyristoylphosphatidylcholine (DMPC) with differential scanning calorimetry, attenuated total reflection Fourier transform infrared spectroscopy (ATR-FTIR) and fluorescence spectroscopy. Despite the very high biological activity of these extracts, such a study has not been undertaken previously. Calorimetric results on the thermotropic parameters of DMPC membranes suggest that BH and BS extracts modify them to a greater extent than SR. Fluorescence and ATR-FTIR results confirm that the compounds contained in the SR extract concentrate in the hydrophilic area of the DMPC bilayer, causing an increase in the order of the polar heads of the lipid, and they do not penetrate the hydrophobic area. Compounds contained in the BS and BH extracts also concentrate in the hydrophilic area of the bilayer; however, they partially affect the hydrophobic-hydrophilic interface of the bilayer as well as the upper part of the acyl chain region.

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Differential interaction of Sophora isoflavonoids with lipid bilayers

Cited by 66 publications

References 31 publications

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

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

Perturbation of the lipid phase of a membrane is not involved in the modulation of MRP1 transport activity by flavonoids

Interaction of skullcap (Scutellaria baicalensis Georgi) and buckwheat (Fagopyrum esculentum Moench) extracts with lipid bilayers

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