Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea.
Three 20(S)-protopanaxatriol-type saponins, ginsenoside-Rg1 (1), notoginsenoside-R1 (2), and ginsenoside-Re (3), were transformed by the fungus Absidia coerulea (AS 3.3389). Compound 1 was converted into five metabolites, ginsenoside-Rh4 (4), 3beta,2beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-beta-D-glucopyranoside (5), 20(S)-ginsenoside-Rh1 (6), 20(R)-ginsenoside-Rh1 (7), and a mixture of 25-hydroxy-20(S)-ginsenoside-Rh1 and its C-20(R) epimer (8). Compound 2 was converted into 10 metabolites, 20(S)-notoginsenoside-R2 (9), 20(R)-notoginsenoside-R2 (10), 3beta,12beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (11), 3beta,12beta-dihydroxydammar-(E)-20(22),24-diene-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (12), 3beta,12beta,20,25-tetrahydroxydammaran-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (13), and compounds 4-8. Compound 3 was metabolized to 20(S)-ginsenoside-Rg2 (14), 20(R)-ginsenoside-Rg2 (15), 3beta,12beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (16), 3beta,12beta-dihydroxydammar-(E)-20(22),24-diene-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (17), 3beta,12beta,20,25-tetrahydroxydammaran-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (18), and compounds 4-8. The structures of five new metabolites, 10-13 and 16, were established by spectroscopic methods.
Chen
Guangtong
G
Shanghai Research Center for Modernization of Traditional Chinese Medicine, Shanghai Institute of Materia Medica, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, Guo Shoujing Road, Zhangjiang, Shanghai, People's Republic of China.
Yang
Min
M
Lu
Zhiqiang
Z
Zhang
Jinqiang
J
Huang
Huilian
H
Liang
Yan
Y
Guan
Shuhong
S
Song
Yan
Y
Wu
Lijun
L
Guo
De-an
DA
D020095:Absidia / Q000378:metabolism*; D001711:Biotransformation; D036145:Ginsenosides / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D005894:Panax / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D012502:Sapogenins / Q000737:chemistry / Q000378:metabolism*; D012503:Saponins / Q000737:chemistry / Q000378:metabolism*; D014315:Triterpenes / Q000737:chemistry / Q000378:metabolism*
D036145:Ginsenosides; D012502:Sapogenins; D012503:Saponins; D014315:Triterpenes; C101280:ginsenoside Rh4; C487685:notoginsenoside R2; C081552:protopanaxatriol; C049864:ginsenoside Re; C026474:ginsenoside Rg2; C425564:ginsenoside Rh1; C035054:ginsenoside Rg1; C072936:notoginsenoside R1