Spirostanoids with 1,4-dien-3-one or 3β,7α-diol-5,6-ene moieties from Solanum violaceum

Bioorg Med Chem Lett. 2013 May 1;23(9):2738-42. doi: 10.1016/j.bmcl.2013.02.060. Epub 2013 Feb 26.

Abstract

Bioassay-guided fractionation of the CHCl3 layer of Solanum violaceum areal parts methanolic extract led to the isolation of four new steroidal sapogenins, indiosides L-O (1-4), along with eight known steroids, one lignin, and a coumarin. Indioside L is a rare spirostanoid possessing a 1,4-dien-3-one moiety in ring A. Moreover, compounds 3 and 4 represent rare examples of spirostene with the 3β,7α-diol-5,6-ene moiety compared to the normal 3β,7β-diol-5,6-ene derivatives. The cytotoxic activity of the isolates (5-14) was evaluated against human hepatoma (HepG2 and Hep3B), human lung carcinoma (A549), and human breast carcinoma (MDA-MB-231 and MCF-7).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / toxicity
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Drug Screening Assays, Antitumor
  • Hep G2 Cells
  • Humans
  • MCF-7 Cells
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Solanum / chemistry*
  • Spirostans / chemistry*
  • Spirostans / isolation & purification
  • Spirostans / toxicity

Substances

  • Antineoplastic Agents
  • Spirostans