title: Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea.
abstract: 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.
authors.affiliation: 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.
authors.forename: Guangtong
authors.initials: G
authors.lastname: Chen
authors.forename: Min
authors.initials: M
authors.lastname: Yang
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Lu
authors.forename: Jinqiang
authors.initials: J
authors.lastname: Zhang
authors.forename: Huilian
authors.initials: H
authors.lastname: Huang
authors.forename: Yan
authors.initials: Y
authors.lastname: Liang
authors.forename: Shuhong
authors.initials: S
authors.lastname: Guan
authors.forename: Yan
authors.initials: Y
authors.lastname: Song
authors.forename: Lijun
authors.initials: L
authors.lastname: Wu
authors.forename: De-an
authors.initials: DA
authors.lastname: Guo
mesh_terms: 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*
chemical_list: 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