Steroidal saponins from Hosta longipes and their inhibitory activity on tumour promoter-induced phospholipid metabolism of HeLa cells

Phytochemistry. 1996 Jul;42(4):1065-70. doi: 10.1016/0031-9422(96)00030-1.

Abstract

Three new spirostanol saponins and two new furostanol saponins were isolated from the underground parts of Hosta longipes. Their structures were determined to be (25R)-5 alpha-spirostane-2 alpha, 3 beta-diol (gitogenin) 3-O-{O-alpha-L -rhamnopyranosyl-(1-->2)-beta-D-galactopyranoside}, gitogenin 3-O-{O-alpha-L-rhamnopyranosyl-(1-->2) -O-[beta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside-, (25R)-5 alpha-spirostan-3 beta-ol (tigogenin) 3-O-{O-alpha-L-rhamnopyranosyl-(1-->2) -O-[beta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside-, 26-O-beta-D-glucopyranosyl-22-O-methyl-(25R)-5 alpha-furostane-2 alpha,3 beta, 22 xi,26-tetrol 3-O-{O-alpha-L-rhamnopyranosyl -(1-->2)-beta-D-galactopyranoside} and 26-O-beta -D-glucopyranosyl-22-O-methyl-(25R)-5 alpha-furostane-2 alpha,3 beta,22 xi,26-tetrol 3-O-{O-alpha-L -rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl -(1-->4)]-beta-D-galactopyranoside}, respectively. The isolated saponins and their derivatives were examined for inhibitory activity on 12-O-tetradecanoylphorbor-13-acetate-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to find new antitumour-promoter compounds.

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Carcinogens / antagonists & inhibitors*
  • Carcinogens / pharmacology
  • HeLa Cells
  • Humans
  • Molecular Sequence Data
  • Molecular Structure
  • Phospholipids / metabolism*
  • Plant Roots
  • Plants*
  • Saponins / chemistry*
  • Saponins / isolation & purification
  • Saponins / pharmacology*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Steroids / chemistry
  • Steroids / isolation & purification
  • Steroids / pharmacology*
  • Tetradecanoylphorbol Acetate / antagonists & inhibitors*
  • Tetradecanoylphorbol Acetate / pharmacology

Substances

  • Carcinogens
  • Phospholipids
  • Saponins
  • Steroids
  • Tetradecanoylphorbol Acetate