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Please use this identifier to cite or link to this item: http://repository.li.mahidol.ac.th/dspace/handle/123456789/34903
Title: Drug solubilization mechanism of α-glucosyl stevia by NMR spectroscopy
Authors: Junying Zhang
Kenjirou Higashi
Keisuke Ueda
Kazunori Kadota
Yuichi Tozuka
Waree Limwikrant
Keiji Yamamoto
Kunikazu Moribe
Chiba University
China Pharmaceutical University
Osaka University of Pharmaceutical Sciences
Mahidol University
Keywords: Pharmacology, Toxicology and Pharmaceutics
Issue Date: 25-Apr-2014
Citation: International Journal of Pharmaceutics. Vol.465, No.1-2 (2014), 255-261
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.
URI: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84898596700&origin=inward
http://repository.li.mahidol.ac.th/dspace/handle/123456789/34903
ISSN: 18733476
03785173
Appears in Collections:Scopus 2011-2015

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