Preparation, characterization, and in vitro anti-inflammatory evaluation of novel water soluble kamebakaurin/hydroxypropyl-β-cyclodextrin inclusion complex

Raza, Aun; Sun, Han‐Dong; Bano, Shumaila; Zhao, Yingying; Xu, Ximing; Tang, Jian

doi:10.1016/j.molstruc.2016.10.059

Cited by 37 publications

(22 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, the different rate ICs reveal a prominent wide absorption band of the hydroxyl group (3,345 cm −1 , 3,409 cm −1 , 3,472 cm −1 ). The C‐O tensile vibration in 1,320 to 1,200 cm −1 was obscured by the HP‐β‐CD characteristic absorption peak, which further indicated that TP had successfully drilled into the cavity of HP‐β‐CD to form the IC (Raza et al., 2017). No significant difference existed between the spectra of the physical mixture and the spectra of the single component.…”

Section: Resultsmentioning

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

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

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

View full text Add to dashboard Cite

show abstract

“…The solvent was evaporated under the vacuum, and good quality of cyclodextrin inclusion complexes was obtained. [113,121] Many essential oils (such as cinnamon, clove, [122] estragole, [123] black pepper oil, [124] thymol, [109] Kamebakaurin, [125] and chloramphenicol) [126] were encapsulated by the formation of inclusion complexes with cyclodextrins. [111] …”

Section: Freeze-drying or Lyophilizationmentioning

confidence: 99%

Untitled

Budhwar¹

2018

AJP

View full text Add to dashboard Cite

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.

show abstract

“…Several essential oils and their pure major active compounds have been encapsulated in hydroxyproply-β-cyclodextrin. These include cinnamon and clove [19], estragole (major component of basil and tarragon essential oils) [20], black pepper essential oil [21], thymol and thyme essential oil [9], kamebakaurin (kaurane diterpene) [22], ITH12674 (multitarget drug) [23] and chloramphenicol [24].…”

Section: Freeze-drying or Lyophilizationmentioning

confidence: 99%

“…[56] have pointed out that inclusion of a guest compound by cyclodextrin can prevent from hydrolytic degradation. The effect of inclusion complex formation on antimicrobial activity and antioxidant property of chlorogenic acid and its complex was also tested by [22]. No significant difference of antimicrobial activity against three bacteria; Staphylococcus aureus, Bacillus subtilis and Escherichia coli, was observed between chlorogenic acid and its complex.…”

Section: Application In Environment Protectionmentioning

confidence: 99%

Inclusion complex formation of cyclodextrin with its guest and their applications

Cheirsilp¹,

Rakmai²

2017

Biol Eng Med

View full text Add to dashboard Cite

Cyclodextrin (CD) are cyclic oligosaccharides consisting of glucopyranosyl units linked by α-(1,4) bonds. The widely used natural cyclodextrins are α-, β-and γ-cyclodextrin consisting of 6, 7 and 8 glucopyranose units, respectively. The cyclodextrin molecules have a unique structure with a hydrophobic cavity and a hydrophilic surface which can form inclusion complex with a wide variety of guests. The use of cyclodextrins and their derivatives for the encapsulation of bioactive compounds can protect the compounds from environmental conditions and improve the aqueous solubility for increasing their capacity to functionalize the products. In some cases, there is a need to enhance water solubility of β-cyclodextrin by adding the hydroxyalkyl groups on the β-cyclodextrin surface. This review aimed to summarize the method for inclusion complex formation of cyclodextrin with its guests and its applications. Table 1. The cyclodextrin molecules have a unique structure with a hydrophobic cavity and a hydrophilic surface in which a guest molecule can be entrapped. Cyclodextrin can form inclusion complex with a wide variety of solid, liquid and gaseous compounds. Complex formation is a dimensional, geometrically limited fit, between cyclodextrin cavity and the guest molecule [2].Generally, hydrophobic molecules have greater affinity for the cyclodextrin cavity when they are in water solution. Moreover, the encapsulation changes the physical and chemical properties of the guests, such as solubility and stability. Therefore, cyclodextrins are suitable for application in food and flavors, pharmaceutical products, cosmetic, agriculture and chemical industries. Cyclodextrins can link specifically to other cyclodextrins (covalent or noncovalent). Because of this property, cyclodextrins can be used as building blocks for the construction of supramolecular complexes. Building blocks which cannot be prepared by common methods can be applied, such as separation of complex mixtures of molecules and enantiomers [3]. Cyclodextrins are produced by reacting gelatinized starch with the enzyme cyclodextrin glucosyltransferase (CGTase) as a result of intramolecular transglycosylation reaction from degradation of starch. Inclusion complex formationCyclodextrins have an internal non-polar hole and hydroxyl groups placed on the surface, the inclusion of hydrophobic compounds takes place mainly by hydrophobic interactions between guest molecules and the walls of cyclodextrin cavity [5]. However, other forces, such as van der Walls and dipole-dipole interactions, may be involved in the binding of the guest. Despite the number of factors and different forces involved in the complexation with cyclodextrins, the production of complexes is a rather simple process. There are several methods to obtain cyclodextrin-guest complexes depending on the properties of the guest and the nature of the chosen cyclodextrin. Kneading methodKneading technique is suitable for poorly water-soluble guests, because the guest is dissolved slowly during the forma...

show abstract

Preparation, characterization, and in vitro anti-inflammatory evaluation of novel water soluble kamebakaurin/hydroxypropyl-β-cyclodextrin inclusion complex

Cited by 37 publications

References 35 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

Untitled

Inclusion complex formation of cyclodextrin with its guest and their applications

Contact Info

Product

Resources

About