Synthesis of cholestane glycosides bearing OSW-1 disaccharide or its 1-->4-linked analogue and their antitumor activities

Bioorg Med Chem Lett. 2010 Sep 15;20(18):5439-42. doi: 10.1016/j.bmcl.2010.07.085. Epub 2010 Jul 29.

Abstract

For further structure-activity relationship (SAR) research of OSW saponins, a cholestane glycoside, namely 3beta, 16beta, 26-trihydroxycholest-5-en-22-one 16-O-(2-O-4-methoxybenzoyl-beta-D-xylopyranosyl)-(1-->3)-2-O-acetyl-alpha-L-arabinopyranoside (1) together with two 1-->4-linked disaccharide analogues (2 and 3) were synthesized. Their cytotoxic activities were evaluated by the standard MTT assay. Compound 1 showed potent cytotoxicity against five types of human tumor cells, with IC50 ranging between 1.3 and 73 nM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic / chemical synthesis
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cholestanes / chemical synthesis
  • Cholestanes / chemistry*
  • Cholestanes / pharmacology*
  • Cholestenones / chemical synthesis
  • Cholestenones / chemistry*
  • Cholestenones / pharmacology*
  • Cytotoxins / chemical synthesis
  • Cytotoxins / chemistry
  • Cytotoxins / pharmacology
  • Drug Screening Assays, Antitumor
  • Glycosides / chemical synthesis
  • Glycosides / chemistry*
  • Glycosides / pharmacology*
  • Humans
  • Models, Molecular
  • Neoplasms / drug therapy
  • Ornithogalum / chemistry
  • Saponins / chemical synthesis
  • Saponins / chemistry*
  • Saponins / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Cholestanes
  • Cholestenones
  • Cytotoxins
  • Glycosides
  • Saponins
  • OSW 1