Transglycosylation to ginseng saponins by cyclomaltodextrin glucanotransferases.
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.
Kim
Y H
YH
Korea Ginseng and Tobacco Research Institute, Yusong-ku, Taejon.
Lee
Y G
YG
Choi
K J
KJ
Uchida
K
K
Suzuki
Y
Y
D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005964:Glucosyltransferases / Q000737:chemistry*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D005894:Panax / Q000737:chemistry*; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal; D012503:Saponins / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment
D012503:Saponins; D005964:Glucosyltransferases; C019963:cyclomaltodextrin glucanotransferase