Publication: Drug solubilization mechanism of α-glucosyl stevia by NMR spectroscopy
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Issued Date
2014-04-25
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ISSN
18733476
03785173
03785173
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2-s2.0-84898596700
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Mahidol University
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SCOPUS
Bibliographic Citation
International Journal of Pharmaceutics. Vol.465, No.1-2 (2014), 255-261
Suggested Citation
Junying Zhang, Kenjirou Higashi, Keisuke Ueda, Kazunori Kadota, Yuichi Tozuka, Waree Limwikrant, Keiji Yamamoto, Kunikazu Moribe Drug solubilization mechanism of α-glucosyl stevia by NMR spectroscopy. International Journal of Pharmaceutics. Vol.465, No.1-2 (2014), 255-261. doi:10.1016/j.ijpharm.2014.01.035 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/34903
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Title
Drug solubilization mechanism of α-glucosyl stevia by NMR spectroscopy
Abstract
We investigated the drug solubilization mechanism of α-glucosyl stevia (Stevia-G) which was synthesized from stevia (rebaudioside-A) by transglycosylation.1H and13C NMR peaks of Stevia-G in water were assigned by two-dimensional (2D) NMR experiments including1H-1H correlation,1H-13C heteronuclear multiple bond correlation, and1H-13C heteronuclear multiple quantum coherence spectroscopies. The1H and13C peaks clearly showed the incorporation of two glucose units into rebaudioside-A to produce Stevia-G, supported by steviol glycoside and glucosyl residue assays. The concentration-dependent chemical shifts of Stevia-G protons correlated well with a mass-action law model, indicating the self-association of Stevia-G molecules in water. The critical micelle concentration (CMC) was 12.0 mg/mL at 37 °C. The aggregation number was 2 below the CMC and 12 above the CMC. Dynamic light scattering and 2D1H-1H nuclear Overhauser effect spectroscopy (NOESY) NMR experiments demonstrated that Stevia-G self-associated into micelles of a few nanometers in size with a core-shell structure, containing a kaurane diterpenoid-based hydrophobic core and a glucose-based shell. 2D1H-1H NOESY NMR measurements also revealed that a poorly water-soluble drug, naringenin, was incorporated into the hydrophobic core of the Stevia-G micelle. The Stevia-G self-assembly behavior and micellar drug inclusion capacity can achieve significant enhancement in drug solubility. © 2014 Elsevier B.V. All rights reserved.