Transglycosylation to ginseng saponins by cyclomaltodextrin glucanotransferases

Biosci Biotechnol Biochem. 2001 Apr;65(4):875-83. doi: 10.1271/bbb.65.875.

Abstract

Ten new alpha-glucosylginsenosides were found to be synthesized from dextrin and four ginsenosides, -Rb1, -Rc, -Re, and -Rg1, by the successive actions of B. stearothermophilus cyclomaltodextrin glucanotransferase and Rhizopus glucoamylase. Seven of them were isolated in the pure state by extraction with n-butanol saturated with water, silica gel column chromatography, and high pressure liquid chromatography, and identified as 3-O-[alpha-D-glcp-(1-->4)-beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[beta-D-glcp-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 3-O-[beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[alpha-D-glcp-(1-->4)-beta-D-glcp-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 3-O-[alpha-D-glcp-(1-->4)-beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[alpha-L-araf-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 3-O-[beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[(4G-alpha-D-glcp)-alpha-L-araf-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 6-O-[alpha-L-rhap-(1-->2)-beta-D-glcp]-20-O-[alpha-D-glcp-(1-->4)-beta-D-glcp]-20(S)-protopanaxatriol, 6-O-[alpha-D-glcp-(1-->4)-beta-D-glcp]-20-O-(beta-D-glcp)-20(S)-protopanaxatriol, and 6-O-[alpha-D-glcp-(1-->3)-beta-D-glcp]-20-O-(beta-D-glcp)-20(S)-protopanaxatriol, by spectroscopy (FAB-MS, IR, 1H-NMR and 13C-NMR) and hydrolysis products in 50% acetic acid. The bitterness of these alpha-glucosyl-ginsenosides was less than that of ginsenosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Glucosyltransferases / chemistry*
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Panax / chemistry*
  • Plant Roots / chemistry
  • Plants, Medicinal*
  • Saponins / chemistry*
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Saponins
  • Glucosyltransferases
  • cyclomaltodextrin glucanotransferase