Preparation and characterization of inclusion complexes of naringenin with β-cyclodextrin or its derivative

Yang, Lijuan; Ma, Songqi; Zhou, Shu-Ya; Wen, Cuié; Yuan, Mingwei; Yin, Yanqing; Yang, Xiaodong

doi:10.1016/j.carbpol.2013.07.010

Cited by 112 publications

(54 citation statements)

References 38 publications

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“…The complex of quercetin with common corn starch was highly amorphous, whereas the complex of genistein with Hylon VII exhibited a V6 III crystalline structure, which was ascribed to guest molecule trapped between the helices . Previous reports on the complex of naringenin with β‐cyclodextrins suggest that the phenyl ring in naringenin was more prone to entering the helix cavity, whereas the chromone moiety was oriented towards the exterior. It is hypothesized that the observed mixed crystalline structures in the present study represent a mixture of naringenin partly inside the helix and partly physically trapped between the helices inter‐dispersed among varying proportions of short and long starch chains.…”

Section: Resultsmentioning

confidence: 90%

“…Cyclodextrins and amylose form inclusion complexes, which have a hydrophilic exterior and a hydrophobic interior where apolar guest molecules are situated . The solubility of naringenin improved by at least 10‐fold when complexed with β‐cyclodextrin and its derivatives; however, concerns remain in the poor water solubility and associated toxicity of cyclodextrins . In contrast, starch chains are flexible, biodegradable, and biocompatible, although complexation is greatly affected by starch structure.…”

Section: Introductionmentioning

confidence: 99%

“…The solubility of naringenin improved by at least 10‐fold when complexed with β‐cyclodextrin and its derivatives; however, concerns remain in the poor water solubility and associated toxicity of cyclodextrins . In contrast, starch chains are flexible, biodegradable, and biocompatible, although complexation is greatly affected by starch structure. Arvisenet et al studied the retention of three aroma compounds, including isoamyl acetate, ethyl hexanoate, and linalool, in common corn and waxy maize starches and found that the three molecules were retained by both starches.…”

Section: Introductionmentioning

confidence: 99%

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Effect of Acetylation and Beta‐Amylase Treatment on Complexation of Debranched Starch with Naringenin

et al. 2018

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Starch inclusion complexation has been shown to improve solubility of water insoluble molecules. Potato starch and Hylon VII are acetylated at two levels and then debranched alone or combined with β‐amylase hydrolysis, and its complexes with naringenin are prepared in aqueous conditions and characterized in this study. Both soluble and insoluble complexes are formed with the soluble complex present in the supernatant and the insoluble complex as the precipitate after centrifugation. The recovery of the soluble complexes and the naringenin content increased when starch is acetylated, and further increased when the β‐amylase treatment is included. The naringenin contents in both complexes from Hylon VII are significantly greater than those from potato starch regardless of treatments. The insoluble complexes comprise a greater naringenin content than the soluble counterparts for both starches. FTIR spectra and thermal properties by differential scanning calorimetry confirm the molecular interaction between starch and naringenin for both complexes. This work is the first to demonstrate that starch derivatives form complexes with naringenin, and both acetylation and the beta‐amylase treatment improve their complexation.

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Section: Resultsmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Effect of Acetylation and Beta‐Amylase Treatment on Complexation of Debranched Starch with Naringenin

et al. 2018

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“…As a result of the preparation of the inclusion compound, positive modifications are provided in the properties of guest molecules, such as enhancement of the dissolution of insoluble substances [18,19], stabilization of nonstable substances against the degrading effects of light and heat [20], masking of undesired odor and taste [21], controlled release of drugs and fragrance-taste substances [22,23], and chromatographic separation [24,25]. The CDs and their inclusion complexes are therefore used as delivery systems in the food, drug, cosmetics, packaging, and textile industries.…”

Section: Introductionmentioning

confidence: 99%

An investigation into the preparation, characterization and antioxidant activity of puerarin/cyclodextrin inclusion complexes

Yue

Zhou

et al. 2015

J Incl Phenom Macrocycl Chem

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The inclusion complexes between puerarin and three cyclodextrins (CDs), namely b-cyclodextrin (b-CD), (2-hydroxy)propyl-b-cyclodextrin (HP-b-CD, DS = 4.2) and methyl-b-cyclodextrin (Me-b-CD, DS = 12.5) were prepared. The effects of the complexation on the stability of puerarin were investigated in both solution and the solid state by methods of phase solubility study, XRD, DSC and SEM. Furthermore, the antioxidant activities of puerarin and puerarin/CDs inclusion complexes were determined by reducing power and 1,1-diphenyl-2-picryl-hydrazyl methods. Results showed that puerarin formed 1:1 stoichiometric inclusion complexes with b-CD, HP-b-CD and Meb-CD. Additionally, the solubility and thermal stability of puerarin was improved after encapsulating by CDs. Antioxidant activity studies showed that the antioxidant performance of the inclusion complex was better than the native puerarin, and puerarin/Me-b-CD complex was the most effective form. It can be a potentially promising way to develop a new formulation of puerarin for herbal medicine or healthcare products.

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“…CDs are cyclic oligomers formed primarily of six to eight d-glucose monomers attached together by α-1, 4-glucose bonds. Such oligomers are characterized by a central hydrophobic core surrounded by a hydrophilic outer surface permitting the encapsulation of a wide variety of drug molecules forming host-guest complexes [31,32]. This complexation allows the reduction of the dose of the administered drug minimizing the expected side effects [33,34].…”

Section: Introductionmentioning

confidence: 99%

Effect of Methyl-Β-Cyclodextrin Complexation on the Hypoglycemic and Hypolipidemic Effects of Khellin: Experimental Study

AbouSamra

Basha

Awdan

et al. 2016

Int J Pharm Pharm Sci

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ABSRACTObjective: The present work tackled the development and evaluation of inclusion complex of khellin (KH) and methyl-β-cyclodextrin (MβCD). In addition, it tested its possible hypoglycemic and hypolipidemic effects. Methods:Inclusion complexes of KH-MβCD in the presence of water-soluble polymer were prepared by freeze drying (FD), co-evaporation (EV) and kneading methods (KN). The selected ternary complex was characterized by Fourier transform infrared spectrophotometry (FTIR), x-ray diffractometry (XRD), differential scanning calorimetry (DSC) and scanning electron microscopy [1]. Assessment of the hypoglycemic effect of the selected ternary complex versus the standard drug metformin was studied. Two different doses of the ternary complex were administered orally to streptozotocin (STZ)-induced type 2diabetic rats. Their hypoglycemic and hypolipidemic effects were evaluated by measuring the fasting blood glucose level (BGL), total cholesterol (TC) and triglycerides levels (TG) along the study period. Results:The FD complex showed the highest drug dissolution rate. All the performed characterization analysis confirmed the formation of a KH-MβCD inclusion complex. The in vivo study declared that both doses showed a marked hypoglycemic and hypolipidemic effects compared to metformin. Conclusion:In conclusion, this study points for the first time that the complexation of KH with MβCD could notably improve the dissolution rate and hence the bioavailability of KH. Moreover, this study demonstrated that this compound has a hypoglycemic and hypolipidemic effect. Thus, it can be a promising natural supportive treatment in type 2 diabetes mellitus (T2DM).

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Preparation and characterization of inclusion complexes of naringenin with β-cyclodextrin or its derivative

Cited by 112 publications

References 38 publications

Effect of Acetylation and Beta‐Amylase Treatment on Complexation of Debranched Starch with Naringenin

Effect of Acetylation and Beta‐Amylase Treatment on Complexation of Debranched Starch with Naringenin

An investigation into the preparation, characterization and antioxidant activity of puerarin/cyclodextrin inclusion complexes

Effect of Methyl-Β-Cyclodextrin Complexation on the Hypoglycemic and Hypolipidemic Effects of Khellin: Experimental Study

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