Cytotoxic Furan- and Pyrrole-Containing Scalarane Sesterterpenoids Isolated from the Sponge Scalarispongia sp

Molecules. 2019 Feb 27;24(5):840. doi: 10.3390/molecules24050840.

Abstract

Three furan-containing scalarane sesterterpenoids (13) and a novel pyrrole-containing analog (4) were isolated from the sponge Scalarispongia species. Compound 3, reported in the literature as a synthetic derivative of furoscalarol 2, was for the first time isolated from a natural source. During the separation performed using a silica column in the presence of methanol, 16-methoxy derivatives (5, 6) were obtained from the unintended reaction of 2. The isolated natural products 3 and 4 and the artifact 5 showed moderate to high cytotoxicity against six human cancer cell lines, whereas compound 6, the C-16 epimer of 5, showed no cytotoxicity at a concentration of 60 μΜ.

Keywords: Scalarispongia; conjugate addition; cytotoxicity; furan; pyrrole; sesterterpenoid.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Cell Survival
  • Drug Screening Assays, Antitumor
  • Furans / chemistry*
  • Humans
  • Molecular Structure
  • Neoplasms / drug therapy
  • Neoplasms / pathology*
  • Porifera / chemistry*
  • Sesterterpenes / chemistry
  • Sesterterpenes / isolation & purification
  • Sesterterpenes / pharmacology*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Furans
  • Sesterterpenes
  • furan