Bioactive saponins and glycosides. VIII. Notoginseng (1): new dammarane-type triterpene oligoglycosides, notoginsenosides-A, -B, -C, and -D, from the dried root of Panax notoginseng (Burk.) F.H. Chen

Chem Pharm Bull (Tokyo). 1997 Jun;45(6):1039-45. doi: 10.1248/cpb.45.1039.

Abstract

The glycosidic fraction from the dried roots of Panax notoginseng (Burk.) F.H. Chen was found to show protective effect on liver injury induced by D-galactosamine and lipopolysaccharide. From the glycosidic fraction with hepatoprotective effect, nine new dammarane-type triterpene oligoglycosides, notoginsenosides-A, -B, -C, -D, -E, -G, -H, -I, and -J and an acetylenic fatty acid glycoside, notoginsenic acid beta-sophoroside, were isolated together with fourteen known dammarane-type triterpene oligoglycosides. The structures of notoginsenosides-A, -B, -C and -D were determined on the basis of chemical and physicochemical evidence, which included the chemical correlation with ginsenoside-Rb1 using photosensitized oxygenation, as follows: notoginsenoside A; 3-O-[beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] 3 beta, 12 beta,20(S),25-tetrahydroxydammar -23-ene; B; 3-O-[beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D-glucopyranosyl (1-->6)-beta-D- glucopyranosyl] 3 beta, 12 beta,20(S)-trihydroxydammar-25-en-24-one, C; 3-O-[beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D -glucopyranosyl (1-->6)-beta-D-glucopyranosyl] 3 beta,12 beta,20(S)- trihydroxy-24 zeta-hydroperoxydammar-25-ene, and D; 3-O-[beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D-xylopyranosyl (1-->6)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl]20(S)-protopanaxadiol, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbon Tetrachloride Poisoning / pathology
  • Dammaranes
  • Drugs, Chinese Herbal / chemistry*
  • Drugs, Chinese Herbal / pharmacology
  • Galactosamine / toxicity
  • Glycosides / chemistry*
  • Glycosides / pharmacology
  • Lipopolysaccharides / toxicity
  • Liver / drug effects
  • Liver / pathology
  • Male
  • Mice
  • Models, Chemical
  • Panax*
  • Plants, Medicinal*
  • Saponins / chemistry*
  • Saponins / pharmacology
  • Spectrometry, Mass, Fast Atom Bombardment
  • Steroids / chemistry*
  • Steroids / pharmacology
  • Triterpenes / chemistry*
  • Triterpenes / pharmacology

Substances

  • Drugs, Chinese Herbal
  • Glycosides
  • Lipopolysaccharides
  • Saponins
  • Steroids
  • Triterpenes
  • Galactosamine