Characterization and antioxidant activity of the complexes of tertiary butylhydroquinone with β-cyclodextrin and its derivatives

Pu, Hongbin; Sun, Qiaomei; Tang, Peixiao; Zhao, Ludan; Li, Qi; Liu, Yuanyuan; Li, Hui

doi:10.1016/j.foodchem.2018.04.008

Cited by 73 publications

(27 citation statements)

References 35 publications

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“…The results of FTIR confirmed the formation of the HP-β-CD/GSE inclusion complex, while other methods provided further verification. The results were consistent with those of previous studies [29,30] in which HPβ-CD was used to encapsulate tertiary butylhydroquinone (TBHQ).…”

Section: Ftir Spectrasupporting

confidence: 93%

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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Section: Ftir Spectrasupporting

confidence: 93%

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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“…The K 1:1 values increase with increasing temperature. The values of K 1:1 is between 178 M −1 and 486 M −1 , which are in agreement with the ranges (between 50 M −1 and 2000 M −1 ) described by other authors [21,32]. These values indicate that ME- β -CD forms a moderate or weak inclusion complex with natamycin in aqueous solution.…”

Section: Resultssupporting

confidence: 91%

Development of Starch-Based Antifungal Coatings by Incorporation of Natamycin/Methyl-β-Cyclodextrin Inclusion Complex for Postharvest Treatments on Cherry Tomato against Botrytis cinerea

et al. 2019

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The application of natamycin as a natural fungicide in edible coatings is challenging because of its low aqueous solubility. In this study, the natamycin/methyl-β-cyclodextrin (N/ME-β-CD) inclusion complex was fabricated and incorporated into waxy corn starch-based coatings for postharvest treatments. The phase solubility of natamycin in the presence of ME-β-CD at 293.2 K, 303.2 K, and 313.2 K is determined and used to calculate the process thermodynamic parameters. The N/ME-β-CD inclusion complex was confirmed and characterized by FTIR and 1H NMR spectroscopy. The results indicated that the inclusion complex was formed and the hydrophobic part (C16-C26) of natamycin might be partially inserted into the cavity of ME-β-CD form the wide rim. The effects of N/ME-β-CD incorporated starch-based coatings (N/ME-β-CD S coatings) on postharvest treatments of cherry tomatoes were evaluated in vivo. The N/ME-β-CD S coatings could reduce weight loss, delay fruit ripening, and inhibit fruit decay caused by Botrytis cinerea in tomato fruit during storage.

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“…Cyclodextrins (CDs) are a class of water-soluble cyclic oligomers derived from starch, composed of six to eight D-glucose units linked by α-1,4-glucose bonds (often namely α-, β-, and γ-CD) 15,16 . The shape of CDs is just like a truncated cone with a hollow hydrophobic interior and a hydrophilic outer surface 17 . Due to this special structure, CDs can form inclusion complexes with a wide variety of organic molecules through the “host-guest interactions”: supramolecular self-assembly 18,19 .…”

Section: Introductionmentioning

confidence: 99%

“…Due to this special structure, CDs can form inclusion complexes with a wide variety of organic molecules through the “host-guest interactions”: supramolecular self-assembly 18,19 . β-CD is most commonly employed and studied because it is cheap 17,20 . However, its application has some limitations due to its low solubility in water, so functional groups, such as hydroxyalkyl and methyl, are often introduced to parent CDs to overcome this shortcoming 21 .…”

Section: Introductionmentioning

confidence: 99%

The mechanism of bensulfuron-methyl complexation with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin and effect on soil adsorption and bio-activity

Geng

Tian

Wang

et al. 2019

Sci Rep

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In this work, the inclusion complexes of hydrophobic herbicide bensulfuron-methyl (BSM) with β-cyclodextrin (β-CD) and (2-hydroxypropyl)-β-CD (2-HP-β-CD) were prepared and characterized. Phase solubility study showed that both β-CD and 2-HP-β-CD increased the solubility of BSM. Three-dimensional structures of the inclusion complexes were simulated by the molecular docking method. The docking results indicated that guest BSM could enter into the cavities of host CDs, folded, and centrally aligned inside the inclusion complexes. The benzene ring of the guest molecule was close to the wide rim of the host molecules; the pyrimidine ring and side chains of the guest molecule were oriented toward the narrow rim of the host molecule. The inclusion complexes were successfully prepared by the coprecipitation method. The physiochemical characterization data of 1H NMR, FT-IR, XRD, and DSC showed that the guest and host molecules were well included. BSM had lower soil adsorption and higher herbicidal activity in the complexation form with β-CD or 2-HP-β-CD than in the pure form. The present study provides an approach to develop a novel CDs-based formulation for hydrophobic herbicides.

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Characterization and antioxidant activity of the complexes of tertiary butylhydroquinone with β-cyclodextrin and its derivatives

Cited by 73 publications

References 35 publications

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

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

Development of Starch-Based Antifungal Coatings by Incorporation of Natamycin/Methyl-β-Cyclodextrin Inclusion Complex for Postharvest Treatments on Cherry Tomato against Botrytis cinerea

The mechanism of bensulfuron-methyl complexation with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin and effect on soil adsorption and bio-activity

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