Enhancement of Solubility and Bioavailability of Quercetin by Inclusion Complexation with the Cavity of Mono‐6‐deoxy‐6‐aminoethylamino‐β‐cyclodextrin

Park, Kyeong Hui; Choi, Joo Hee; Cho, Eunae; Jeong, Dae‐Yong; Shinde, Vijay Vilas; Kim, Hyungsup; Choi, Youngjin; Jung, Seunho

doi:10.1002/bkcs.11192

Cited by 20 publications

(10 citation statements)

References 49 publications

(81 reference statements)

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“…2). This intriguing complicated biphasic increase in glucose uptake is speculated to involve migration and various non-covalent interactions, including hydrogen bonds, van der Waals forces, electrostatic interactions, and hydrophobic interactions in the solvent 34 . These interactions are involved in complexation of quercetin and isorhamnetin with macromolecules, which affects the solubility and absorption rate of quercetin and isorhamnetin in target tissues 35 .…”

Section: Discussionmentioning

confidence: 99%

Quercetin and its metabolite isorhamnetin promote glucose uptake through different signalling pathways in myotubes

Jiang

Yamashita

Nakamura

et al. 2019

Sci Rep

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Quercetin and its metabolite isorhamnetin elicit various beneficial effects on human health. However, their bioavailability is low. In this study, we investigated whether low concentrations in the physiological range could promote glucose uptake in L6 myotubes, as well as the underlying molecular mechanisms. We found that 0.1 nM and 1 nM quercetin or 1 nM isorhamnetin significantly increased glucose uptake via translocation of glucose transporter type 4 (GLUT4) to the plasma membrane of L6 myotubes. Quercetin principally activated the CaMKKβ/AMPK signalling pathway at these concentrations, but also activated IRS1/PI3K/Akt signalling at 10 nM. In contrast, 1 nM and 10 nM isorhamnetin principally activated the JAK/STAT pathway. Treatment with siAMPKα and siJAK2 abolished quercetin- and isorhamnetin-induced GLUT4 translocation, respectively. However, treatment with siJAK3 did not affect isorhamnetin-induced GLUT4 translocation, indicating that isorhamnetin induced GLUT4 translocation mainly through JAK2, but not JAK3, signalling. Thus, quercetin preferably activated the AMPK pathway and, accordingly, stimulated IRS1/PI3K/Akt signalling, while isorhamnetin activated the JAK2/STAT pathway. Furthermore, after oral administration of quercetin glycoside at 10 and 100 mg/kg body weight significantly induced GLUT4 translocation to the plasma membrane of skeletal muscles in mice. In the same animals, plasma concentrations of quercetin aglycone form were 4.95 and 6.80 nM, respectively. In conclusion, at low-concentration ranges, quercetin and isorhamnetin promote glucose uptake by increasing GLUT4 translocation via different signalling pathways in skeletal muscle cells; thus, these compounds may possess beneficial functions for maintaining glucose homeostasis by preventing hyperglycaemia at physiological concentrations.

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Section: Discussionmentioning

confidence: 99%

Quercetin and its metabolite isorhamnetin promote glucose uptake through different signalling pathways in myotubes

Jiang

Yamashita

Nakamura

et al. 2019

Sci Rep

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“…This was due to that, on the one hand, β‐CD might increase the solubility of SOEO. The inner hydrophobic and outer hydrophilic properties of β‐CD could make the insoluble SOEO molecules enter the inner cavities of β‐CD and form inclusion complexes, which made the solubility of SOEO increased in water . On the other hand, β‐CD might increase the bioavailability of SOEO.…”

Section: Discussionmentioning

confidence: 99%

“…β‐CD is a stable, nontoxic, or low toxic, semi‐natural product with hydrophilic rims, and hydrophobic cavities. Due to the hydrophobic property and space volume matching effect of the cavities, β‐CD can form stable host‐guest inclusion complexes with hydrophobic molecules of appropriate size and shape through noncovalent interactions . The inclusion encapsulation method here, without high temperature and cross‐linking agents, was economical, safe, and had a wide range of applications.…”

Section: Introductionmentioning

confidence: 99%

Microcapsule of Sweet Orange Essential Oil Encapsulated in Beta‐Cyclodextrin Improves the Release Behaviors In Vitro and In Vivo

Huang

et al. 2018

Euro J Lipid Sci & Tech

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To protect sweet orange essential oil (SOEO) from volatilization and oxidation, and also to expand the range of application in physiology or medicine, beta‐cyclodextrin (β‐CD) is employed to develop SOEO microcapsules via an inclusion encapsulation method in this study. An optimal encapsulating condition obtained from response surface methodology (RSM) is an SOEO mass of 5.66 g, an encapsulating time of 3.24 h, and an encapsulating temperature of 53.7 °C, which provides the greatest encapsulation efficiency (EE) of 50.31%. Particle size and scanning electron microscope (SEM) reveal that rhombus, trapezoid, and parallelogram can be found in optimized microcapsule aggregates with a particle size of 1.34 ± 0.58 µm. Fourier transform infrared spectroscopy (FT‐IR) and differential scanning calorimetry (DSC) confirm the encapsulation of SOEO in β‐CD. Furthermore, the release study in vitro suggests that SOEO in microcapsules can be better released in simulated gastric fluid (SGF) than in simulated intestinal fluid, and the study in vivo suggests that, β‐CD might increase the solubility and bioavailability of SOEO. Thus, the microcapsules have potentials to be applied to the biomedical industry. Practical Applications: The optimal encapsulating condition is attained using RSM, and SOEO is capsuled to be a stable form in optimized microcapsules. The active ingredients of SOEO can be exerted fully by microcapsules. The microcapsules have excellent potentials for use as biological or pharmaceutical products. In this study, microcapsules of SOEO are developed using RSM. The physical and chemical characterizations of SOEO microcapsules are analyzed. The release behaviors in vitro and in vivo are also researched. Though these works, the microcapsules increase the solubility and bioavailability of SOEO, which has potentials for application in the biomedical industry.

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“…Both endothermic peaks of atrazine and Cys were also detected in the DSC curve of the atrazine/Cys physical mixture. The change in the form of melting peak on the DSC curve of the physical mixture can be explained by the solid–solid [50,51]. Therefore, the change in form of melting peak on the DSC curve of the physical mixture might be affected by Cys as a solid state.…”

Section: Resultsmentioning

confidence: 99%

Solubility Enhancement of Atrazine by Complexation with Cyclosophoraose Isolated from Rhizobium leguminosarum biovar trifolii TA-1

et al. 2019

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Rhizobium leguminosarum biovar trifolii TA-1, a kind of soil bacteria, produces cyclosophoraoses (Cys). Cyclosophoraoses contain various ring sizes with degrees of polymerization ranging from 17 to 23. Atrazine is a hardly-soluble herbicide that contaminates soil and drinking water, and remains in soil for a long time. To remove this insoluble contaminant from aqueous solutions, we have enhanced the solubility of atrazine by complexation with Cys. The complex formation of Cys and atrazine was confirmed using 1H nuclear magnetic resonance (NMR), Fourier transform infrared (FT-IR) spectroscopy, differential scanning calorimetry (DSC), field emission scanning electron microscopy (FE-SEM), rotating frame nuclear overhauser spectroscopy (ROESY), and molecular modeling studies. The aqueous solubility of atrazine was enhanced 3.69-fold according to the added concentrations (20 mM) of Cys, compared to the 1.78-fold enhancements by β-cyclodextrin (β-CD). Cyclosophoraoses as an excellent solubility enhancer with long glucose chains that can effectively capture insoluble materials showed a potential application of microbial polysaccharides in the removal of hazardous hardly-soluble materials from aqueous solutions in the fields of biological and environmental industry.

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Enhancement of Solubility and Bioavailability of Quercetin by Inclusion Complexation with the Cavity of Mono‐6‐deoxy‐6‐aminoethylamino‐β‐cyclodextrin

Cited by 20 publications

References 49 publications

Quercetin and its metabolite isorhamnetin promote glucose uptake through different signalling pathways in myotubes

Quercetin and its metabolite isorhamnetin promote glucose uptake through different signalling pathways in myotubes

Microcapsule of Sweet Orange Essential Oil Encapsulated in Beta‐Cyclodextrin Improves the Release Behaviors In Vitro and In Vivo

Solubility Enhancement of Atrazine by Complexation with Cyclosophoraose Isolated from Rhizobium leguminosarum biovar trifolii TA-1

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