Studies on the interactions between some flavonols and cyclodextrins

Bergonzi, Maria Camilla; Bilia, Anna Rita; Bari, Lorenzo Di; Mazzi, Giovanni; Vincieri, Franco Francesco

doi:10.1016/j.bmcl.2007.08.067

Cited by 46 publications

(35 citation statements)

References 17 publications

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“…Taken together, our IR, DSC, NMR, and SEM analyses suggest the formation of a quercetin/β-cyclodextrin solid complex by physical mixture, a different method when compared to others previously described, which employ liquid or semisolid media (5,(11)(12)(13)(14)(15)(16)(17)(18)(19). According to Zheng et al (13) who elucidated the mode of interaction between quercetin and β-cyclodextrin using a molecular modeling study, the B-ring, the C-ring, and part of the A-ring (except C 6 ) of quercetin are positioned inside the β-cyclodextrin cavity.…”

Section: Scanning Electron Microscopycontrasting

confidence: 42%

“…Many studies assessing quercetin/cyclodextrin complexes (11)(12)(13)(14)16,17) using the phase-solubility technique do not mention the exact amount of quercetin added to cyclodextrin solutions; neither do they inform the influence of the operating conditions employed, such as temperature and stirring time. This lack of information about the influence temperature, stirring time, and excess amount of quercetin on quercetin/β-cyclodextrin complexation in aqueous media was the motivation of our investigation employing a 2 3 factorial design.…”

Section: Factorial Designmentioning

confidence: 99%

“…Some studies have shown that the association of quercetin with cyclodextrins to form inclusion complexes improves the aqueous solubility (5,(11)(12)(13)(14)(15)(16)(17) and dissolution rate (16) of the flavonoid. Most quercetin/β-cyclodextrin solid complexes are prepared in liquid media, (aqueous solution submitted to freeze-drying (12,14,18), co-evaporation (11,16), or thin layer (11) methods) or semisolid media (kneading method (11,14,16,19)).…”

Section: Introductionmentioning

confidence: 99%

“…Most quercetin/β-cyclodextrin solid complexes are prepared in liquid media, (aqueous solution submitted to freeze-drying (12,14,18), co-evaporation (11,16), or thin layer (11) methods) or semisolid media (kneading method (11,14,16,19)). However, no study to date has used a factorial design to assess the influence of operating conditions such as temperature, stirring time, and excess amount of quercetin on the complexation of quercetin with β-cyclodextrin.…”

Section: Introductionmentioning

confidence: 99%

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Quercetin/β-Cyclodextrin Solid Complexes Prepared in Aqueous Solution Followed by Spray-drying or by Physical Mixture

et al. 2009

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Abstract. The present study was designed to investigate the influence of operating conditions (temperature, stirring time, and excess amount of quercetin) on the complexation of quercetin with β-cyclodextrin using a 2 3 factorial design. The highest aqueous solubility of quercetin was reached under the conditions 37°C/24 h/6 mM of quercetin. The stoichiometric ratio (1:1) and the apparent stability constant (Ks=230 M −1 ) of the quercetin/β-cyclodextrin complex were determined using phase-solubility diagrams. The semi-industrial production of a 1:1 quercetin/β-cyclodextrin solid complex was carried out in aqueous solution followed by spray-drying. Although the yield of the spray-drying process was adequate (77%), the solid complex presented low concentration of quercetin (0.14%, w/w) and, thus, low complexation efficiency. The enhancement of aqueous solubility of quercetin using this method was limited to 4.6-fold in the presence of 15 mM of β-cyclodextrin. Subsequently, an inclusion complex was prepared via physical mixture of quercetin with β-cyclodextrin (molar ratio of 1:1 and quercetin concentration of 23% (w/w)) and characterized using infrared spectroscopy, differential scanning calorimetry, nuclear magnetic resonance spectroscopy, and scanning electron microscopy analyses. The enhancement of aqueous solubility of quercetin using this method was 2.2-fold, similar to that found in the complex prepared in aqueous solution before the spray-drying process (2.5-fold at a molar ratio of 1:1, i.e., 6 mM of quercetin and 6 mM of β-cyclodextrin).

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Section: Scanning Electron Microscopycontrasting

confidence: 42%

Section: Factorial Designmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quercetin/β-Cyclodextrin Solid Complexes Prepared in Aqueous Solution Followed by Spray-drying or by Physical Mixture

et al. 2009

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“…This fact is corroborated by studies using single-polyphenol solutions and β-cyclodextrin, where the molecular stoichiometry observed was 1:1 [26][27][28][29]. Thus, increased CD enabled the entrapment of more polyphenol molecules that diffused from the solid particles, leading to higher solubilization in the liquid phase [30][31][32], hence the higher Y TP .…”

Section: Resultsmentioning

confidence: 60%

Optimization of a Green Extraction/Inclusion Complex Formation Process to Recover Antioxidant Polyphenols from Oak Acorn Husks (Quercus Robur) Using Aqueous 2-Hydroxypropyl-β-Cyclodextrin/Glycerol Mixtures

et al. 2016

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Aqueous mixtures of glycerol and 2-hydroxypropyl-β-cyclodextrin (CD), two non-toxic eco-friendly substances, were used as a means of extracting antioxidant polyphenols from oak acorn (Quercur robur) husks. The process was optimized by implementing a central composite (Box-Behnken) experimental design and response surface methodology, taking into consideration the critical parameters (independent variables) of glycerol concentration (C gl ), CD concentration (C CD ) and temperature (T). The assessment of the extraction model was based on three responses: the total polyphenol yield (Y TP ), the antiradical activity (A AR ) and the reducing power (P R ). The model illustrated that Y TP depended significantly on C gl and C CD , but not on T, whereas both antioxidant properties considered (A AR and P R ) were temperature-dependent. The maximum predicted Y TP was 122.19 mg GAE per g dry husk weight, while the extract obtained under optimized conditions displayed strong antioxidant activity.

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Mass Spectrometry as a Complementary Approach for Noncovalently Bound Complexes Based on Cyclodextrins

Silion

Fifere

Lungoci

et al. 2019

Advances in Experimental Medicine and Biology

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Studies on the interactions between some flavonols and cyclodextrins

Cited by 46 publications

References 17 publications

Quercetin/β-Cyclodextrin Solid Complexes Prepared in Aqueous Solution Followed by Spray-drying or by Physical Mixture

Quercetin/β-Cyclodextrin Solid Complexes Prepared in Aqueous Solution Followed by Spray-drying or by Physical Mixture

Optimization of a Green Extraction/Inclusion Complex Formation Process to Recover Antioxidant Polyphenols from Oak Acorn Husks (Quercus Robur) Using Aqueous 2-Hydroxypropyl-β-Cyclodextrin/Glycerol Mixtures

Mass Spectrometry as a Complementary Approach for Noncovalently Bound Complexes Based on Cyclodextrins

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