Novel steroidal saponins from Liriope graminifolia (Linn.) Baker with anti-tumor activities

Carbohydr Res. 2011 Feb 1;346(2):253-8. doi: 10.1016/j.carres.2010.11.015. Epub 2010 Nov 21.

Abstract

Phytochemical investigation of the underground parts of Liriope graminifolia (Linn.) Baker resulted in the isolation of two new steroidal saponins lirigramosides A (1) and B (2) along with four known compounds. The structures were determined by extensive spectral analysis, including two-dimensional (2D) NMR spectroscopy and chemical methods, to be 3-O-[β-d-xylopyranosyl-(1→3)-α-l-arabinopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranosyl-(25S)-spirost-5-ene-3β,17α-diol (1), 1-O-[α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl]-(25R)-ruscogenin (2), 1-O-β-d-xylopyranosyl-3-O-α-l-rhamnopyranosyl-(25S)-ruscogenin (3), 3-O-α-l-rhamnopyranosyl-1-O-sulfo-(25S)-ruscogenin (4), methylophiopogonanone B (5), and 5,7-dihydroxy-3-(4-methoxybenzyl)-6-methyl-chroman-4-one, (ophiopogonanone B, 6), respectively. Compound 1 has a new (25S)-spirost-5-ene-3β,17α-diol ((25S)-pennogenin) aglycone moiety. The isolated compounds were evaluated for their cytotoxic activities against Hela and SMMC-7721 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Carbohydrate Sequence
  • HeLa Cells
  • Humans
  • Liliaceae / chemistry*
  • Molecular Sequence Data
  • Saponins / chemistry*
  • Saponins / isolation & purification
  • Saponins / pharmacology*
  • Steroids / chemistry*
  • Steroids / isolation & purification
  • Steroids / pharmacology*

Substances

  • 1-O-(rhamnopyranosyl-(1-2)-xylopyranosyl)ruscogenin
  • 3-O-(xylopyranosyl-(1-3)-arabinopyranosyl-(1-2)-(rhamnopyranosyl-(1-4)-glucopyranosyl))spirost-5-ene-3,17-diol
  • Antineoplastic Agents
  • Saponins
  • Steroids