Characterization of glabridin/hydroxypropyl-β-cyclodextrin inclusion complex with robust solubility and enhanced bioactivity

Wei, Yongqin; Zhang, Jin; Zhou, Yan; Bei, Weiya; Li, Yuan; Yuan, Qipeng; Liang, Hao

doi:10.1016/j.carbpol.2016.11.093

Cited by 110 publications

(40 citation statements)

References 49 publications

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“…It is possible that when antioxidants enter the cavity of cyclodextrin, phenolic hydroxyl groups form intramolecular hydrogen bonds, while increasing the degree of hydroxylation and stability of guest molecules, which makes it easier to react with DPPH free radicals (Strazisar, Andrensek, & Smidovnik, 2008; Yuan, Du, Jin, & Xu, 2013). The same phenomena were also observed for the natural antioxidant canthaxanthin, glabridin, and their CD ICs (Gharibzahedi, Razavi, & Mousavi, 2014; Wei et al., 2017).…”

Section: Resultssupporting

confidence: 66%

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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Section: Resultssupporting

confidence: 66%

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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“…SmartPearls consisting of mesoporus silica particles have been combined also with glabridin to enhance its water solubility by a factor higher than four and therefore improve its dermal bioavailability [237]. A 20-fold increase of tyrosinase inhibition activity has also been reported for a glabridin/hydroxypropyl-β-cyclodextrin inclusion complex [238].…”

Section: New Trends In the Search For Tyrosinase Inhibitorsmentioning

confidence: 99%

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

2019

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One of the most common approaches for control of skin pigmentation involves the inhibition of tyrosinase, a copper-containing enzyme which catalyzes the key steps of melanogenesis. This review focuses on the tyrosinase inhibition properties of a series of natural and synthetic, bioinspired phenolic compounds that have appeared in the literature in the last five years. Both mushroom and human tyrosinase inhibitors have been considered. Among the first class, flavonoids, in particular chalcones, occupy a prominent role as natural inhibitors, followed by hydroxystilbenes (mainly resveratrol derivatives). A series of more complex phenolic compounds from a variety of sources, first of all belonging to the Moraceae family, have also been described as potent tyrosinase inhibitors. As to the synthetic compounds, hydroxycinnamic acids and chalcones again appear as the most exploited scaffolds. Several inhibition mechanisms have been reported for the described inhibitors, pointing to copper chelating and/or hydrophobic moieties as key structural requirements to achieve good inhibition properties. Emerging trends in the search for novel skin depigmenting agents, including the development of assays that could distinguish between inhibitors and potentially toxic substrates of the enzyme as well as of formulations aimed at improving the bioavailability and hence the effectiveness of well-known inhibitors, have also been addressed.

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“…Scanning electron microscopy was also a useful method to study the structure of the materials [ 32 , 33 ]. Figure 5 shows the SEM photographs of daidzein, HP-β-CD, their physical mixture, and their inclusion complex.…”

Section: Resultsmentioning

confidence: 99%

Studies on the Inclusion Complexes of Daidzein with β-Cyclodextrin and Derivatives

Chen

et al. 2017

Molecules

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The inclusion complexes between daidzein and three cyclodextrins (CDs), namely β-cyclodextrin (β-CD), methyl-β-cyclodextrin (Me-β-CD, DS = 12.5) and (2-hydroxy)propyl-β-cyclodextrin (HP-β-CD, DS = 4.2) were prepared. The effects of the inclusion behavior of daidzein with three kinds of cyclodextrins were investigated in both solution and solid state by methods of phase-solubility, XRD, DSC, SEM, 1H-NMR and 2D ROESY methods. Furthermore, the antioxidant activities of daidzein and daidzein-CDs inclusion complexes were determined by the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) method. The results showed that daidzein formed a 1:1 stoichiometric inclusion complex with β-CD, Me-β-CD and HP-β-CD. The results also showed that the solubility of daidzein was improved after encapsulating by CDs. 1H-NMR and 2D ROESY analyses show that the B ring of daidzein was the part of the molecule that was most likely inserted into the cavity of CDs, thus forming an inclusion complex. Antioxidant activity studies showed that the antioxidant performance of the inclusion complexes was enhanced in comparison to the native daidzein. It could be a potentially promising way to develop a new formulation of daidzein for herbal medicine or healthcare products.

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Characterization of glabridin/hydroxypropyl-β-cyclodextrin inclusion complex with robust solubility and enhanced bioactivity

Cited by 110 publications

References 49 publications

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

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

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

Studies on the Inclusion Complexes of Daidzein with β-Cyclodextrin and Derivatives

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