Preparation and Physicochemical Properties of the Complex of Naringenin with Hydroxypropyl-β-Cyclodextrin

Wen, Juan; Liu, Benguo; Yuan, Erdong; Ma, Yixin; Yongyi, Zhu

doi:10.3390/molecules15064401

Cited by 61 publications

(20 citation statements)

References 9 publications

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“…As reported by Zhang and coworkers [21] the solubility of naringenin gradually increases as the temperature increases; based on these results, it is expected to obtain lower extraction of these compounds during ultrasound extraction instead of that of infusion. This hypothesis can be confirmed with the results obtained by Wen et al [22] that noticed that naringenin is insoluble in water at room temperature.…”

Section: Quantification Of Polar Compoundssupporting

confidence: 91%

Determination of Polar Compounds in Guava Leaves Infusions and Ultrasound Aqueous Extract by HPLC-ESI-MS

Díaz‐de‐Cerio

Verardo

Gómez-Caravaca

et al. 2015

Journal of Chemistry

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Literature lacks publications about polar compounds content in infusion or guava leaves tea. Because of that, a comparison between different times of infusion and a conventional ultrasound aqueous extract was carried out. Several polar compounds have been identified by HPLC-ESI-MS and their antioxidant activity was evaluated by FRAP and ABTS assays. Four different classes of phenolic compounds (gallic and ellagic acid derivatives, flavonols, flavanones, and flavan-3-ols) and some benzophenones were determined. The quantification results reported that the order, in terms of concentration of the classes of polar compounds in all samples, was flavonols > flavan-3-ols > gallic and ellagic acid derivatives > benzophenones > flavanones. As expected, the aqueous extract obtained by sonication showed the highest content in the compounds studied. Significative differences were noticed about the different times of infusion and five minutes was the optimal time to obtain the highest content in polar compounds using this culinary method. All the identified compounds, except HHDP isomers and naringenin, were positively correlated with antioxidant activity.

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Section: Quantification Of Polar Compoundssupporting

confidence: 91%

Determination of Polar Compounds in Guava Leaves Infusions and Ultrasound Aqueous Extract by HPLC-ESI-MS

Díaz‐de‐Cerio

Verardo

Gómez-Caravaca

et al. 2015

Journal of Chemistry

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“…This may explain the inverse correlation between the dietary consumption of flavonoids and the incidence of hormone related breast, prostate, testicular, and colorectal cancers [368,369]. While data support the potential medicinal use of flavonoids for the treatment of ER related cancers, their low bioavailability [370], combined with the length of time it takes to run human clinical tirals, has limited their use. Flavonoids were reported to exhibit a comparable activity to that of well known P-glycoprotein [P-gp] inhibitors (e.g., verapamil and cyclosporine), without toxicity to normal cells [371].…”

Section: Natural and Dietary Substances That Block Cancer Prolifementioning

confidence: 99%

Sustained proliferation in cancer: Mechanisms and novel therapeutic targets

Feitelson

Arzumanyan

Kulathinal

et al. 2015

Seminars in Cancer Biology

502

346

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Proliferation is an important part of cancer development and progression. This is manifest by altered expression and/or activity of cell cycle related proteins. Constitutive activation of many signal transduction pathways also stimulates cell growth. Early steps in tumor development are associated with a fibrogenic response and the development of a hypoxic environment which favors the survival and proliferation of cancer stem cells. Part of the survival strategy of cancer stem cells may manifested by alterations in cell metabolism. Once tumors appear, growth and metastasis may be supported by overproduction of appropriate hormones (in hormonally dependent cancers), by promoting angiogenesis, by undergoing epithelial to mesenchymal transition, by triggering autophagy, and by taking cues from surrounding stromal cells. A number of natural compounds (e.g., curcumin, resveratrol, indole-3-carbinol, brassinin, sulforaphane, epigallocatechin-3-gallate, genistein, ellagitannins, lycopene and quercetin) have been found to inhibit one or more pathways that contribute to proliferation (e.g., hypoxia inducible factor 1, nuclear factor kappa B, phosphoinositide 3 kinase/Akt, insulin-like growth factor receptor 1, Wnt, cell cycle associated proteins, as well as androgen and estrogen receptor signaling). This data, in combination with bioinformatics analyses, will be very important for identifying signaling pathways and molecular targets that may provide early diagnostic markers and/or critical targets for the development of new drugs or drug combinations that block tumor formation and progression.

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“…The chromone ring system of naringenin (5,7-dihydroxychromone residue; rings A and C in Figure 1a) forms an angle of 77.261(4)° with the phenyl ring B and protrudes extensively from the primary rim of the host. The The inclusion of naringenin in native and modified cyclodextrins has been extensively characterized by UV-Vis, FTIR [14,15], NMR, XRD, DSC/TGA, and SEM [16,17] techniques. Moreover, computational studies of molecular docking and subsequent MD simulations have been performed [7,18].…”

Section: Naringenin/dm-β-cd Inclusion Complexmentioning

confidence: 99%

Inclusion Complexes of Naringenin in Dimethylated and Permethylated β-Cyclodextrins: Crystal Structures and Molecular Dynamics Studies

2019

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The crystal structures of the inclusion complexes of naringenin in dimethylated and permethylated β-cyclodextrin (DM-β-CD and TM-β-CD) were determined and extensively analyzed. Naringenin is found with its 4-hydroxyphenyl residue fully immersed in the DM-β-CD cavity and its chromone group protruding from the narrow rim of the open-cone shaped host. The naringenin/DM-β-CD complex units are packed in a ‘herring bone’ fashion. In the case of naringenin/TM-β-CD, the complex units are arranged in a cage-type mode, the guest naringenin is partially encapsulated in the cavity of the closed-cone shaped host, with its chromone group laying equatorially and its 4-hydroxyphenyl protruding extensively from the wide rim of the host. Furthermore, the crystallographically-determined coordinates of both complexes were employed for Molecular Dynaimics simulations in explicit water solvent and in the absence of crystal contacts. The trajectories showed that naringenin rapidly penetrates the open narrow rim of DM-β-CD but not the closed narrow rim of TM-β-CD. Thus, in the latter case, the chromone group of naringenin is accommodated shallowly in the wide rim of the host, tethered via hydrogen bonds to the secondary methoxy groups of the host. Finally, a significantly higher binding affinity for naringenin in DM-β-CD than TM-β-CD was estimated by Molecular Mechanics/Generalized Born Surface Area calculations.

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Preparation and Physicochemical Properties of the Complex of Naringenin with Hydroxypropyl-β-Cyclodextrin

Cited by 61 publications

References 9 publications

Determination of Polar Compounds in Guava Leaves Infusions and Ultrasound Aqueous Extract by HPLC-ESI-MS

Determination of Polar Compounds in Guava Leaves Infusions and Ultrasound Aqueous Extract by HPLC-ESI-MS

Sustained proliferation in cancer: Mechanisms and novel therapeutic targets

Inclusion Complexes of Naringenin in Dimethylated and Permethylated β-Cyclodextrins: Crystal Structures and Molecular Dynamics Studies

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