Cyclodextrin encapsulated catechin: Effect of pH, relative humidity and various food models on antioxidant stability

Ho, Siyin; Thoo, Yin Yin; Young, David J.; Siow, Lee Fong

doi:10.1016/j.lwt.2017.07.028

Cited by 68 publications

(25 citation statements)

References 34 publications

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“…Among the three major kinds of CDs, the most commonly used is β-CD which matches with most of the regular guests within the molecular weight range of 200~800 g/mol and its cost is also quite reasonable (Waleczek, Marques, Hempel, & Schmidt, 2003). There were some previous works related to the complexation between CAT and CDs (Ho et al, 2017a(Ho et al, , 2017bJullian et al, 2007;Krishnaswamy, Orsat, & Thangavel, 2012;Żyżelewicz, Oracz, Kaczmarska, Budryn, & Grzelczyk, 2018). The results indicated that CAT can be encapsulated into the cavity of CDs.…”

Section: Introductionmentioning

confidence: 99%

Physicochemical properties of catechin/β-cyclodextrin inclusion complex obtained via co-precipitation

Jiang

Yang

Wang

et al. 2019

CyTA - Journal of Food

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Inclusion complex of catechin (CAT) with β-cyclodextrin (β-CD) was prepared using co-precipitation method to enhance antioxidant stability of CAT and the physicochemical properties of the inclusion complex were studied. The CAT/β-CD inclusion complex was analyzed through phase solubility study, Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), scanning electron microscopy (SEM) and X-ray diffraction (XRD). Phase solubility study indicated that CAT and β-CD formed 1:1 stoichiometric inclusion complex. Results of FT-IR indicated that CAT was stabilized in β-CD cavity by intra-molecular hydrogen bonds. Results of DSC and SEM proved that CAT/β-CD inclusion complex formed. XRD results showed that the formation of new solid crystalline phases in the CAT/β-CD inclusion complex. CAT was effectively protected through encapsulation into β-CD and the antioxidant stability of CAT was improved after encapsulation. In addition, the release behavior of CAT from the inclusion complex increased with increasing of the temperature. Propiedades fisicoquímicas del complejo de inclusión de catequina/β-ciclodextrina obtenido por coprecipitación RESUMEN En el presente estudio se obtuvo el complejo de inclusión de catequina (CAT) con β-ciclodextrina (β-CD) utilizando el método de coprecipitación con el propósito de mejorar la estabilidad antioxidante del CAT. Posteriormente se estudiaron las propiedades fisicoquímicas del complejo de inclusión resultante. Para analizar el complejo de inclusión CAT/β-CD se emplearon los siguientes estudios: estudio de solubilidad de fase, espectroscopia infrarroja transformada de Fourier (FT-IR), calorimetría diferencial de barrido (DSC), microscopía electrónica de barrido (SEM) y difracción de rayos X (DRX). El estudio de solubilidad de fase mostró que el CAT y la β-CD formaron un complejo de inclusión estequiométrica de 1:1. Por su parte, los resultados de FT-IR indicaron que en la cavidad β-CD el CAT fue estabilizado por enlaces de hidrógeno intramoleculares. Los resultados aportados por la DSC y la SEM demostraron que se formó un complejo de inclusión CAT/β-CD. Los resultados de la DRX dieron cuenta de la formación de nuevas fases cristalinas sólidas en el complejo de inclusión CAT/β-CD. El CAT se protegió eficazmente mediante la encapsulación en la β-CD y su estabilidad antioxidante mejoró después de ocurrir la encapsulación. Además, el comportamiento de liberación del CAT a partir del complejo de inclusión se incrementó con el aumento de la temperatura.

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Section: Introductionmentioning

confidence: 99%

Physicochemical properties of catechin/β-cyclodextrin inclusion complex obtained via co-precipitation

Jiang

Yang

Wang

et al. 2019

CyTA - Journal of Food

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“…HP-β-CD is modified β-CDs containing seven D-glucopyranoside fragments of hydroxypropyl in the sixth position, resulting in better solubility in water [19,20]. Researchers have studied various applications of HP-β-CD, including encapsulation of polyphenols [1,21,22]. For example, polyphenol-cyclodextrin inclusion complexes not only prevent dityrosine cross-linkage, but also reduce protein oligomerisation [23], and they can reduce the partial degradation of essential amino acids, thereby decreasing adverse interactions between proteins and polyphenols [24].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterisation of Polyphenol-HP-β-Cyclodextrin Inclusion Complex that Protects Lamb Tripe Protein against Oxidation

Lidan

Liu

et al. 2019

Molecules

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Grape seed extract (GSE) displays strong antioxidant activity, but its instability creates barriers to its applications. Herein, three HP-β-CD/GSE inclusion complexes with host–guest ratios of 1:0.5, 1:1, and 1:2 were successfully prepared by co-precipitation method to improve stability. Successful embedding of GSE in the HP-β-CD cavity was confirmed by fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), differential scanning calorimetry (DSC), and scanning electron microscopy (SEM) analyses. The Autodock Tools 1.5.6 was used to simulate the three-dimensional supramolecular structure of the inclusion complex of 2-hydroxypropyl-β-cyclodextrin and grape seed extract (HP-β-CD/GSE) by molecular docking. The MALDI-TOF-MS technology and chemical database Pubchem, and structural database PDB were combined to reconstitute the three-dimensional structure of target protein. The binding mode of the HP-β-CD/GSE inclusion complex to target protein was studied at the molecular level, and the antioxidant ability of the resulting HP-β-CD/GSE inclusion complexes was investigated by measuring 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging. The effects of HP-β-CD/GSE on myofibrillar protein from lamb tripe were also investigated under oxidative conditions. The positions and interactions of the binding sites of HP-β-CD/GSE inclusion complexes and target protein receptors were simulated by molecular docking. The results showed that HP-β-CD/GSE inclusion complexes were successfully prepared, optimally at a molar ratio of 1:2. At low (5 μmol/g) to medium (105 μmol/g) concentrations, HP-β-CD/GSE inclusion complexes decreased the carbonyl content, hydrophobicity, and protein aggregation of myofibrillar protein from lamb tripe, and increased the sulphydryl content. Furthermore, high concentration (155 μmol/g) of HP-β-CD/GSE inclusion complexes promoted protein oxidation.

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“…Alkylated CDs are also less toxic than the parent β-CD. [51] β-CD has a hydrophilic outer surface and a lipophilic central cavity to accommodate a variety of lipophilic drugs, [39] resulting in increased solubility of the incorporated drug, enhanced permeation for macromolecular drugs, [52] and inhibition of certain protease activities. [53,54] γ-CD γ-CD possesses large internal cavity size and also have the advantage to encapsulate the bigger molecules which cannot be entrapped by the α-and β-CD s. [42] γ-CD has the highest aqueous solubility than other natural cyclodextrins because of its noncoplanar and flexible structure.…”

Section: β-Cyclodextrin (β-Cd)mentioning

confidence: 99%

“…[76] The formation of inclusion complexes of catechin with β-CD s showed the higher storage stability and provided more protection against temperature, oxygen, and light. [51] Sulfamethoxazole β-CD Enhance bioavailability and dissolution rate [67] Eslicarbazepine acetate β-CD Faster onset of action and higher bioavailability [69] Polylactic acid β-CD Improve the thermal expansion stability [72] Chimonanthus praecox β-CD Enhancement of antioxidant activity and thermal stability [73] Famotidine Carboxymethyl β-CD Improvement of chemical stability, oral bioavailability, and bitter taste [75] Astaxanthin HP-β-CD Storage stability and antioxidant activity [76] Catechin β-CD Protection of antioxidants, higher storage stability against temperature, oxygen, and light [51] α-tocopherol β-CD Higher antioxidant activity and better UV-light stability.…”

Section: Storage Stabilitymentioning

confidence: 99%

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Untitled

Budhwar¹

2018

AJP

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Inclusion complexes have various applications in different fields of drug delivery and pharmaceutical industry due to their ability of complexation with guest molecules and enhancement of the physicochemical properties of guest molecules. Cyclodextrins and their derivatives have the ability to encapsulate the bioactive compounds into its cavity and protect these from the environmental conditions, improve the solubility, bioavailability, and other properties also. The aim of this review is to highlight the advantages of cyclodextrins in the enhancement of physicochemical properties of drugs (such as solubility, stability, bioavailability, permeability, and others), different methods for production and various characterization techniques used for evaluation of complexes. Applications of cyclodextrin complexes in pharmaceutical and other fields are also explained here with examples. Thus cyclodextrins, because of their continuing ability to find several novel applications in drug delivery, are expected to solve many problems accompanied with the delivery of different novel drugs through various delivery routes.

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Cyclodextrin encapsulated catechin: Effect of pH, relative humidity and various food models on antioxidant stability

Cited by 68 publications

References 34 publications

Physicochemical properties of catechin/β-cyclodextrin inclusion complex obtained via co-precipitation

Physicochemical properties of catechin/β-cyclodextrin inclusion complex obtained via co-precipitation

Preparation and Characterisation of Polyphenol-HP-β-Cyclodextrin Inclusion Complex that Protects Lamb Tripe Protein against Oxidation

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