Transglycosylation to Ginseng saponins by cyclomaltodextrin glucanotransferases

Ten new alpha -glucosylginsenosides were found to be synthesized from dextrin and four ginsenosides, -Rb-1, -Rc, -Re, and -Rg(1), by the successive actions of B, stearother- mophilus cyclomaltodextrin g: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)-protspanasadiol, 3-O-[beta -D-glcp]-(1 -->2)-beta -D-glcp]-20-O-[alpha -D-glcp-(1 -->4)-beta -D-glcp-D-glcp]-20(S)-protopanaxadiol, -t (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-[(4(G)-alpha -D-glcp)-alpha -L-araf-(1 -->6)-beta -D-glcp-(1 -->2)-topanaxadiot, 6-O-[alpha -D-glcp-(1 -->2)-beta -D-glcp]-20-O-D-gltp-(1 -->4)-1-D-glcp]-20(S)-prottjpanasatrial, S-0-[alpha -D-9rsp-(1 -->4) beta -D-glcp]-20-O-(beta -D-glcp]-20-O(S)-protopanasatriol, and 6-O-[alpha -D-glcp-(1 -->3)-beta -D-glcp]-20-O-(beta -D-glcp)-20(S)-protopanasat by spectroscopy (FAB-MS, IR, H-1-NMR and C-13-NMR) and ItSdrorysis products in 50% acetic acid. The bitterness of these alpha -glucosyl-ginsenosides was less than that of ginsenosides.