Propyl gallate/cyclodextrin supramolecular complexes with enhanced solubility and radical scavenging capacity

Li, Qian; Pu, Hongbin; Tang, Peixiao; Tang, Bin; Sun, Qiaomei; Li, Hui

doi:10.1016/j.foodchem.2017.11.065

Cited by 41 publications

(21 citation statements)

References 32 publications

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“…"free", in the culture medium of BHSCC. These results are in agreement with the observed increase in RSA values of extracellular extracts, Figure 4b, and with literature reports, indicating an increase in the antioxidant activity of encapsulated antioxidants [26][27][28]. weeks into fresh medium.…”

Section: Effect Of Cds On the Radical Scavenging Activity Of Gallic Asupporting

confidence: 93%

“…CDs. The hypothesis is in agreement with literature reports that suggest that RSA values from complexed antioxidants are significantly higher [26][27][28]. To assess this hypothesis, we carried out a new experiment on the complexation of some representative antioxidants and investigated their radical scavenging activity in the presence of CDs.…”

Section: Radical Scavenging Activity Of Intracellular and Extracellulsupporting

confidence: 88%

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Cyclodextrin-elicited Bryophyllum Suspension Cultured Cells: Enhancement of the Production of Bioactive Compounds

García-Pérez

Losada‐Barreiro

Gallego

2019

Preprint

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The rates of production of secondary metabolites obtained by employing conventional plant breeding may be low for practical purposes. Thus, innovative approaches for increasing their rates of production are being developed. Here, we propose the use of elicited suspension plant cultured cells (PSCC) with cyclodextrins (CDs) as an alternative method for the production of bioactive compounds from Bryophyllum species. For the purpose, we analyzed the effects of methyl--cyclodextrin and 2-hydroxypropyl--cyclodextrin on cell culture growth and on the intra- and extracellular production of phenols and flavonoids. Results clearly show that CDs enhance the biosynthesis of polyphenols by PSCC favoring their accumulation outside the cells. CDs shift the homeostatic equilibrium by complexing extracellular phenolics, causing stress in cells that respond by increasing the production of intracellular phenolics. We also analyzed the radical scavenging activity of the culture medium extracts against DPPH• radical, which increased with respect to the control samples (no added CDs). Our results suggest that both the increase in the production of polyphenols and their radical scavenging activity are a consequence of their inclusion in the CD cavities. Overall, based on our findings, CDs can be employed as hosts for increasing the production of polyphenols from Bryophyllum species.

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Section: Effect Of Cds On the Radical Scavenging Activity Of Gallic Asupporting

confidence: 93%

Section: Radical Scavenging Activity Of Intracellular and Extracellulsupporting

confidence: 88%

Cyclodextrin-elicited Bryophyllum Suspension Cultured Cells: Enhancement of the Production of Bioactive Compounds

García-Pérez

Losada‐Barreiro

Gallego

2019

Preprint

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“…Phase solubility study not only can be used to analyze the stoichiometry but also to determine the binding constant (Li et al, 2018). Figure 1 shows phase solubility diagram of CAT with β-CD.…”

Section: Phase Solubility Studymentioning

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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“…FTIR provides qualitative information that can be used to estimate interactions between host and guest molecules (Abarca et al., 2016; Q. Li et al., 2018). The FTIR spectra of TP, HP‐β‐CD, the physical mixture of TP/HP‐β‐CD, and the IC are depicted in Figure 1.…”

Section: Resultsmentioning

confidence: 99%

“…The grid spacing of the docking box was 1 Å, and the entire receptor was covered by setting X , Y , and Z centers to 0.126, 0.662, and 0.109, and x , y , and z arg sizes to 16, 14, and 14 in the HP‐β‐CD box. Grid maps of various atoms of ligands and receptors were constructed using AutoGrid (Version 5.9.1, AuiltoGrid systems, Inc., Redwood City, CA), and 200 flexible ligand docking modelings were carried out to search for possible docking points and corresponding energies after grid map generation (Q. Li et al., 2018). During the docking process, the exhaustiveness parameter was set to 32, nine conformations could be generated, and other parameters were default.…”

Section: Methodsmentioning

confidence: 99%

Inclusion complexes of tea polyphenols with HP‐β‐cyclodextrin:Preparation, characterization, molecular docking, and antioxidant activity

Zhong

Lidan

et al. 2020

Journal of Food Science

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The purpose of this study was to prepare and characterize inclusion complexes between tea polyphenol (TP) and hydroxypropyl-β-cyclodextrin (HP-β-CD), and to evaluate their antioxidant properties. Freeze-drying was used to prepare the inclusion complex of TP/HP-β-CD at different component ratios (1:0.5, 1:1, and 1:2). The supermolecular structure of the TP/HP-β-CD complex was characterized by Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), and scanning electron microscopy (SEM). Molecular docking was used to simulate the positions and interactions of the binding sites of TP/HP-β-CD inclusion complexes and target protein receptors. In addition, the effects of TP/HP-β-CD inclusion complexes on myofibrillar protein (MP) from lamb tripe were observed under oxidative conditions. Results showed that TP was encapsulated in the cavity of HP-β-CD to form an optimal complex with 1:2 molar ratio of stoichiometry, while the FTIR, TGA, and SEM studies also support the inclusion process. Molecular modeling results were systematically analyzed to determine the stability of inclusion complexes and protein. Furthermore, the addition of an appropriate concentration (5 to 105 µmol/g) of TP/HP-β-CD inclusion complex decreased the carbonyl content, hydrophobicity, and protein aggregation of MP from lamb tripe, whereas it increased the sulfhydryl content. This improved antioxidant activity and bioavailability of the inclusion complexes will be beneficial for its potential applications in food.Practical Application: Tea polyphenol was an antioxidant with potential for the field of food. In this study, the unstable properties of tea polyphenols were evaluated and were improved by inclusion of HP-β-cyclodextrin. The binding mode of the inclusion complex with protein was revealed via the molecular docking method, and the application of inclusion complex to control protein oxidation was studied. Results showed that the inclusion complex could effectively inhibit protein oxidation, which can provide a reference for the application of polyphenols in meat products and the improvement of protein properties.

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Propyl gallate/cyclodextrin supramolecular complexes with enhanced solubility and radical scavenging capacity

Cited by 41 publications

References 32 publications

Cyclodextrin-elicited Bryophyllum Suspension Cultured Cells: Enhancement of the Production of Bioactive Compounds

Cyclodextrin-elicited Bryophyllum Suspension Cultured Cells: Enhancement of the Production of Bioactive Compounds

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

Inclusion complexes of tea polyphenols with HP‐β‐cyclodextrin:Preparation, characterization, molecular docking, and antioxidant activity

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