Enhancement of antioxidant activity of green tea epicatechins in β-cyclodextrin cavity: Single-crystal X-ray analysis, DFT calculation and DPPH assay

Aree, Thammarat; Jongrungruangchok, Suchada

doi:10.1016/j.carbpol.2016.05.113

Cited by 44 publications

(30 citation statements)

References 54 publications

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“…Having one glucose unit less, the cavity of β-CD is narrower and therefore the tilted structure of a flavonoid does not fit and one of the rings of the guest is positioned outside the cavity. This geometry was recently demonstrated for epigallocatechin, which has the same molecular backbone as fisetin, and features the ring B protruding from the primary rim of β-CD in the crystal structure of the β-CD·epigallocatechin inclusion compound [44]. PXRD of the rehydrated γ-CD·fisetin solid shows that the supramolecular arrangement of γ-CD·fisetin complex units is consistent with channel packing, a structure occurring frequently in solid γ-CD inclusion compounds.…”

Section: Resultssupporting

confidence: 52%

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

Pais¹,

Barroca²,

Marques³

et al. 2017

Beilstein J. Org. Chem.

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Fisetin is a natural antioxidant with a wide range of nutraceutical properties, including antidiabetic, neuroprotecting, and suppression or prevention of tumors. The present work describes the preparation of a water-soluble, solid inclusion compound of fisetin with gamma-cyclodextrin (γ-CD), a cyclic oligosaccharide approved for human consumption. A detailed physicochemical analysis of the product is carried out using elemental analysis, powder X-ray diffraction (PXRD), Raman, infrared and 13C{1H} CP-MAS NMR spectroscopies, and thermal analysis (TGA) to verify fisetin inclusion and to present a hypothetical structural arrangement for the host–guest units. The antioxidant activity of the γ-CD·fisetin inclusion compound is evaluated by the DPPH assay.

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Section: Resultssupporting

confidence: 52%

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

Pais¹,

Barroca²,

Marques³

et al. 2017

Beilstein J. Org. Chem.

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“…Cyclodextrin (CD) is a general term for a series of cyclic oligosaccharides. They have a truncated conical‐shaped cavity with a hydrophobic central cavity and hydrophilic perimeters, plus a hydrophobic binding site for complexes that include a variety of guest molecules. Due to the hydrophobic and hydrophilic characteristics of the external cavity, CD and other guest molecules are able to form inclusion complexes that are based on van der Waals' forces or hydrophobic interaction.…”

Section: Introductionmentioning

confidence: 99%

“…Cyclodextrin (CD) is a general term for a series of cyclic oligosaccharides. They have a truncated conical-shaped cavity with a hydrophobic central cavity and hydrophilic perimeters, [24] plus a hydrophobic binding site for complexes that include a variety of guest Abbreviations: HSA, human serum albumin; PDB, Protein Database Bank; SFS, synchronous fluorescence spectroscopy.…”

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confidence: 99%

Insights into the interaction of methotrexate and human serum albumin: A spectroscopic and molecular modeling approach

et al. 2017

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In this study, fluorescence spectroscopy and molecular modeling approaches were employed to investigate the binding of methotrexate to human serum albumin (HSA) under physiological conditions. From the mechanism, it was demonstrated that fluorescence quenching of HSA by methotrexate results from the formation of a methotrexate/HSA complex. Binding parameters calculated using the Stern-Volmer method and the Scatchard method showed that methotrexate binds to HSA with binding affinities in the order 10 L·mol . Thermodynamic parameter studies revealed that the binding reaction is spontaneous, and that hydrogen bonds and van der Waals interactions play a major role in the reaction. Site marker competitive displacement experiments and a molecular modeling approach demonstrated that methotrexate binds with appropriate affinity to site I (subdomain IIA) of HSA. Furthermore, we discuss some factors that influence methotrexate binding to HSA.

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“…Their structure is rich in phenolic hydroxyl groups, which can provide active hydrogen and terminate the chain reaction of free radicals (Li et al., 2012; Shao, Niu, Chen, & Sun, 2018). It is worth noting, however, that TPs are highly reactive and prone to oxidative damage when exposed to light, oxygen, and temperature (Aree & Jongrungruangchok, 2016). In addition, polyphenols can also interact with proteins via hydrogen bonds and hydrophobic interactions, and these phenomena lead to polyphenol precipitating proteins to form an insoluble state, resulting in poor functional properties and nutritional characteristics (Feng et al., 2017; Ozdal, Capanoglu, & Altay, 2013).…”

Section: Introductionmentioning

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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Enhancement of antioxidant activity of green tea epicatechins in β-cyclodextrin cavity: Single-crystal X-ray analysis, DFT calculation and DPPH assay

Cited by 44 publications

References 54 publications

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

Insights into the interaction of methotrexate and human serum albumin: A spectroscopic and molecular modeling approach

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

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