Investigation of transport of genistein, daidzein and their inclusion complexes prepared with different cyclodextrins on Caco-2 cell line

Daruházi, Ágnes Emma; Kiss, Tímea; Vecsernyés, Miklós; Szente, Lajos; Szöke, Éva; Lemberkovics, Éva

doi:10.1016/j.jpba.2013.05.012

Cited by 26 publications

(14 citation statements)

References 16 publications

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“…antioxidant properties of flavonoids, metabolites previously found in this species [6,7,14,20], and is in accordance with previous studies demonstrating strong in chemico and in vitro antioxidant activity of G. tridentata extracts [6,21,22]. There are evidences in the literature that at least genistein, biochanin A, and daidzein can contribute to the observed effects [23,24]. These compounds have direct ROS scavenging activity and were also shown to increase the expression of superoxide dismutase and glutathione peroxidase, key enzymes in the protection of cell from oxidative damage [25,26].…”

Section: [μG/ml] Figsupporting

confidence: 90%

Flavonoid Profile of the Genista tridentata L., a Species Used Traditionally to Treat Inflammatory Processes

et al. 2020

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Ethnopharmacological surveys on Portuguese flora reveal that Genista tridentata L. is a shrub used in traditional medicine for the treatment of various inflammation-related health problems, although scientific support of its benefits is still necessary. In order to establish the anti-inflammatory potential of G. tridentata and support its traditional use, ethanolic extracts of three sections of the plant (root, stem, and leaves) were subjected to in vitro evaluation of anti-inflammatory activity using lipopolysaccharide (LPS)-stimulates macrophages as an inflammation model. Simultaneously, we also aimed to establish the extracts’ flavonoids profile. The ethanolic extracts, obtained by Soxhlet extraction, profile of the three sections confirmed their richness in flavonoids, being three prenylated flavonoids isolated and characterized in the root, including a new natural compound, the 3-methoxymundulin. The extracts from the three plant sections showed strong antioxidant activity at the cellular level and significantly inhibit the LPS-triggered NO production by downregulating Nos2 gene transcription and consequently iNOS expression. Additionally, root and stem extracts also decreased the LPS-induced transcription of the pro-inflammatory genes Il1b, Il6, and Ptgs2. Thus, the results support the anti-inflammatory properties attributed to G. tridentate preparations. Relevantly, the roots of the shrub, plant part not used, is an unexplored source of compounds with pharmacological and nutraceutical value.

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Section: [μG/ml] Figsupporting

confidence: 90%

Flavonoid Profile of the Genista tridentata L., a Species Used Traditionally to Treat Inflammatory Processes

et al. 2020

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“…Even if the effects of cyclodextrins were not tested on the flavone chrysin permeability, other isoflavones such as genistein and daidzein were complexed and studied on Caco-2 monolayers. HPBCD and RAMEB had better solubility enhancement on genistein and daidzein than βCD and gamma-CD (γCD), and RAMEB was the most effective to improve the permeability of daidzein [29]. Although the chemical structures of these molecules are similar, the position of the B-ring and the number and position of hydroxyl groups influence their host-guest interaction with cyclodextrins.…”

Section: Discussionmentioning

confidence: 99%

Cyclodextrin Complexation Improves the Solubility and Caco-2 Permeability of Chrysin

et al. 2020

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Chrysin is a bioflavonoid that can be found in natural products such as honey and propolis, and it possesses several biological effects such as antioxidant, anti-inflammatory, and anti-cancer activity. However, it is poorly soluble in water, and its bioavailability is limited. The aim of this research is to investigate the chrysin solubilization capacity of different β-cylcodextrin derivatives and compare their biological activities. Chrysin was complexed with β-cyclodextrin (βCD), hydroxypropyl-β-, (HPBCD) sulfobutylether-β-, (SBECD), and randomly-methylated-β-cyclodextrin (RAMEB) by the lyophilization method in 1:1 and 1:2 molar ratios. The solubilities of the chrysin–cyclodextrin complexes were tested, and the solubilization abilities of cyclodextrins were studied by phase solubility experiments. The cytotoxicity of the complexes was measured by the MTT method, and the permeability enhancement was tested on Caco-2 monolayers. The solubility study showed that the complexes formed with RAMEB had the highest solubility in water. The phase solubility experiments confirmed the strongest interaction between RAMEB and chrysin. In the viability test, none of the complexes showed cytotoxicity up to 100 µM concentration. The permeability study revealed that both at 1:1 and 1:2 ratios, the RAMEB complexes were the most effective to enhance chrysin permeability through the Caco-2 monolayers. In conclusion, cyclodextrins, especially RAMEB, are suitable for improving chrysin solubility and absorption.

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“…For GCD-GTMAC the solubilization 457 effect was noticeable although rather small while GCD-EDA 458 strongly complexed DAI and increased its concentration in an 459 aqueous solution. Similar behavior was found for b-cyclodextrin 460 which barely solubilized DAI, in contrast to its derivatives, i.e., 461 hydroxypropyl-b-cyclodextrin (HP-b-CD) and random methyl-462 b-cyclodextrin (RAMEB), which significantly enhanced DAI and 463genistein solubility[6]. Since the molar concentration of solubi-464 lized DAI was higher than the molar concentration of GCD-EDA,465 it could be concluded that one GCD-ECD molecule may complex 466 more than one DAI molecule, on the average.…”

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confidence: 54%

Enhanced delivery of daidzein into fibroblasts and neuronal cells with cationic derivatives of gamma-cyclodextrin for the control of cellular glycosaminoglycans

Kamiński

Kujdowicz

Kajta

et al. 2015

European Journal of Pharmaceutics and Biopharmaceutics

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Investigation of transport of genistein, daidzein and their inclusion complexes prepared with different cyclodextrins on Caco-2 cell line

Cited by 26 publications

References 16 publications

Flavonoid Profile of the Genista tridentata L., a Species Used Traditionally to Treat Inflammatory Processes

Flavonoid Profile of the Genista tridentata L., a Species Used Traditionally to Treat Inflammatory Processes

Cyclodextrin Complexation Improves the Solubility and Caco-2 Permeability of Chrysin

Enhanced delivery of daidzein into fibroblasts and neuronal cells with cationic derivatives of gamma-cyclodextrin for the control of cellular glycosaminoglycans

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