Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea

J Nat Prod. 2007 Jul;70(7):1203-6. doi: 10.1021/np070053v. Epub 2007 Jul 13.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Absidia / metabolism*
  • Biotransformation
  • Ginsenosides / chemistry
  • Ginsenosides / metabolism*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Panax / chemistry*
  • Plants, Medicinal / chemistry*
  • Sapogenins / chemistry
  • Sapogenins / metabolism*
  • Saponins / chemistry
  • Saponins / metabolism*
  • Triterpenes / chemistry
  • Triterpenes / metabolism*

Substances

  • Ginsenosides
  • Sapogenins
  • Saponins
  • Triterpenes
  • ginsenoside Rh4
  • notoginsenoside R2
  • protopanaxatriol
  • ginsenoside Re
  • ginsenoside Rg2
  • ginsenoside Rh1
  • ginsenoside Rg1
  • notoginsenoside R1