Solubility enhancement of steviol glycosides and characterization of their inclusion complexes with gamma-cyclodextrin

Int J Mol Sci. 2011;12(11):7529-53. doi: 10.3390/ijms12117529. Epub 2011 Nov 3.

Abstract

Steviol glycosidesrebaudioside (reb) A, C and D have low aqueous solubilities. To improve their aqueous solubilities, inclusion complex of steviol glycosides, reb A, C and D and gamma cyclodextrin were prepared by freeze drying method and further characterized by means of differential scanning calorimetry, Fourier transform infrared spectroscopy and Raman spectroscopy. The effect of gamma cyclodextrin on chemical shifts of the steviol glycosides was also studied in proton NMR experiments as well as in solid state (13)C CP/MAS NMR experiments. These results indicated that the steviol glycosides were clearly in inclusion complex formation with the gamma cyclodextrin which also results in solubility enhancement of these steviol glycosides. Phase solubility studies showed that amounts of soluble reb A, C and D increased with increasing amounts of gamma cyclodextrin indicating formation of 1:1 stoichiometric and higher order inclusion complexes.

Keywords: DSC; FT-IR; NMR; Raman; cyclodextrin; solubility; steviol glycoside.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Calorimetry, Differential Scanning
  • Diterpenes, Kaurane / chemistry*
  • Freeze Drying
  • Magnetic Resonance Spectroscopy
  • Solubility
  • Spectroscopy, Fourier Transform Infrared
  • Spectrum Analysis, Raman
  • gamma-Cyclodextrins / chemistry*

Substances

  • Diterpenes, Kaurane
  • gamma-Cyclodextrins
  • steviol
  • gamma-cyclodextrin