Spectroscopic characterization of the inclusion complexes of luteolin with native and derivatized β-cyclodextrin

Jullian, Carolina; Cifuentes, Constanza; Alfaro, Muriel; Miranda, Sebastián; Barriga, Germán; Olea‐Azar, Claudio

doi:10.1016/j.bmc.2010.05.079

Cited by 47 publications

(16 citation statements)

References 26 publications

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“…Our measurements are performed in alkaline solution where both flavonoid molecules are dissociated. In the case of quercetin the values of the stability constant of anion:β-cyclodextrin 602 M -1 (found electrochemically) or 515 M -1 (fluorescence spectroscopy) are in agreement with finding in literature by Zheng et al 12 . Zheng et al demonstrated that the stability constant of the inclusion complex of undissociated quercetin with hydroxypropyl-β-cyclodextrin (HPβ-CD) is significantly higher than the stability constants of its dissociated form (1009 M -1 ).…”

Section: The Electrochemical Propertiessupporting

confidence: 88%

“…The stability constant of inclusion complex of undissociated quercetin with β-cyclodextrin (β-CD) determined by phase solubility study at pH 3 is 1028 M -1 according to Zheng et al 11 . Values of stability constant found by fluorescence spectroscopy by Jullian et al 12 The present paper proves the protective properties of β-cyclodextrin against the oxidation process of the flavonoid dyes quercetin and luteolin. The protection properties of β-CD against the oxidation was found in case of catechin 14 , chlorogenic acid 15 , ferrocene derivatives 15,16 and chlorpromazine 17 .…”

supporting

confidence: 75%

“…In addition, cyclodextrins have been successfully immobilized by physical or chemical bonds on the surface of fibres 18,19 . Since these flavonoid dyes undergo decomposition in the alkaline aqueous solution in the presence of oxygen 12 , the study of the degradation processes of an anionic molecule of quercetin and luteolin encapsulated by β-CD under inert atmosphere of argon is proposed. Our preliminary results confirm that hydroxyl groups substituted on ring B of the flavonoids are protected against the oxidation by encapsulating by molecule of β-CD.…”

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confidence: 99%

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The influence of the host–guest interaction on the oxidation of natural flavonoid dyes

Ramešová

Sokolová

Degano

et al. 2011

Collect. Czech. Chem. Commun.

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Šárka RAMEŠOVÁ a1 , Romana SOKOLOVÁ a2, *, Ilaria DEGANO b1 , Magdaléna HROMADOVÁ a3 , Miroslav GÁL a4 , Viliam KOLIVOŠKA a5 and a special issue of CCCC devoted to "distinguished followers of the J. Heyrovský School of Polarography". This work is dedicated to Dr. L. Pospíšil on the occasion of his 70th birthday.The influence of the molecular cavity protection on degradation processes of bioorganic compounds quercetin and luteolin used as the original dyes in old tapestries was studied. The degradation processes were studied by electrochemical methods in aqueous media. The products of the exhaustive electrolysis were separated and identified by GC-MS analysis. Cyclic voltammetry characteristics indicate that the inclusion complex is formed. The inclusion affects the redox potentials of both oxidation waves related to the different dissociation forms of the flavonoid molecule. It was shown that decomposition products formed by the oxidation of quercetin are stabilized in the cavity of β-cyclodextrin, including the main oxidation product 2(3′,4′-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3(2H)-one. The formation of the 1:1 inclusion complex of luteolin with β-cyclodextrin is supported by the enhancement of fluorescence intensity. In the case of quercetin, a decrease of fluorescence intensity occurs when 1:1 inclusion complex with β-cyclodextrin is formed.

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Section: The Electrochemical Propertiessupporting

confidence: 88%

supporting

confidence: 75%

mentioning

confidence: 99%

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The influence of the host–guest interaction on the oxidation of natural flavonoid dyes

Ramešová

Sokolová

Degano

et al. 2011

Collect. Czech. Chem. Commun.

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“…The thermodynamic properties are important for the understanding and processing method optimization of βCD complex development. Several physical–chemical methods have been used to characterize the thermodynamic properties of inclusion complexes including UV spectroscopy [16, 17], NMR spectroscopy [17], as well as liquid chromatographic methods, such as thin layer chromatography [18] and high performance liquid chromatography (or High Pressure Liquid Chromatography HPLC) system [19, 20]. The difference on retention characteristics between complexed drug and neat drug [21, 22] can be used to evaluate their thermodynamic properties.…”

Section: Introductionmentioning

confidence: 99%

A thermodynamic study of the cyclodextrin-UC781 inclusion complex using a HPLC method

Yang

Parniak

Hillier

et al. 2011

J Incl Phenom Macrocycl Chem

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UC781, a very potent HIV-1 non-nucleoside reverse transcriptase inhibitor with extreme hydrophobicity and poor water solubility, is under development as a topical vaginal microbicide product to prevent HIV transmission. In this study, the thermodynamic behavior of the interaction between UC781 with three cyclodextrins (CDs): β-cyclodextrin (βCD), hydroxypropyl-β-cyclodextrin (HPβCD) and methyl-β-cyclodextrin (MβCD), was investigated using a reversed-phase HPLC method. A mobile phase consisting of acetonitrile: H2O (30:70) solution containing various CD concentrations was used. The retention time at different temperatures was determined to evaluate the inclusion process. The influence of βCDs on the solubility and hydrophobicity of UC781 was characterized by retention time values. The results showed that the inclusion capacity of cyclodextrins follows the order MβCD > βCD > HPβCD. An enthalpy–entropy compensation effect was also observed. In addition, the results revealed that the change of ΔH is greater than that of ΔS. These results suggested that the complexation of UC781 with βCDs is an enthalpy driven process. The modification on β-cyclodextrin will influence the inclusion process.

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“…In this regard, the structure of the CD derivative used as complexation agent plays a critical role. The derivatives that are able to make hydrogen bonds with the included molecule, such as HPβCD, would, in general, contribute to the increase of antioxidant activity, as observed in the case of luteolin complexes with HPβCD [36]. On the other hand, flavonoid complexation with methylated βCD derivatives (RAMEB) decreases their antioxidant activity due to the reduced ability of RAMEB to form hydrogen bonds [37].…”

mentioning

confidence: 95%

Therapeutic Potential of Hydroxypropyl-β-Cyclodextrin-Based Extract of Medicago sativa in the Treatment of Mucopolysaccharidoses

2016

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Mucopolysaccharidoses are inherited metabolic disorders resulting in the dysfunction of enzymes involved in the degradation of glycosaminoglycans, leading to severe clinical symptoms and a significantly shortened life span of patients. Flavonoids are recognized as glycosaminoglycan metabolism modulators, able to correct glycosaminoglycan cell storage. Therefore, the aim of this work was the development of an efficient and eco-friendly extraction process of phytochemicals from by simultaneous use of ultrasound extraction and hydroxypropyl--cyclodextrin complexation, and investigation of the potential of such an extract as a glycosaminoglycan metabolism modulator. The Box-Behnken design and response surface methodology were used in order to optimize the extraction process, considering hydroxypropyl--cyclodextrin concentration, ultrasonic power, and extraction time as the key parameters. The dependent variables included total phenolicand total flavonoid content, DPPH radical scavenging activity, and Fe chelating activity, due to the importance of oxidative stress in the pathology of mucopolysaccharidoses. The developed technology using hydroxypropyl--cyclodextrin led to more selective flavonoid extraction from than obtained either by the use of water or ethanol. The lyophilization of extracts resulted in products with high radical scavenging activity, suitable for further use. The application of 20 mM hydroxypropyl--cyclodextrin solution, 432 W ultrasonic power, and an extraction time of 45 min resulted in an extract with both the highest total flavonoid content and the lowest radical scavenging activity IC. This extract reduced the levels of glycosaminoglycans in skin fibroblasts of mucopolysaccharidose III patient in a dose-dependent manner. At concentrations of 3 and 6 µg/mL, the observed levels of glycosaminoglycans were reduced by 41.2 and 51.1 %, respectively, clearly demonstrating the validity of the selected approach.

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Spectroscopic characterization of the inclusion complexes of luteolin with native and derivatized β-cyclodextrin

Cited by 47 publications

References 26 publications

The influence of the host–guest interaction on the oxidation of natural flavonoid dyes

The influence of the host–guest interaction on the oxidation of natural flavonoid dyes

A thermodynamic study of the cyclodextrin-UC781 inclusion complex using a HPLC method

Therapeutic Potential of Hydroxypropyl-β-Cyclodextrin-Based Extract of Medicago sativa in the Treatment of Mucopolysaccharidoses

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