Tedanolide C: a potent new 18-membered-ring cytotoxic macrolide isolated from the Papua New Guinea marine sponge Ircinia sp

J Org Chem. 2006 Mar 17;71(6):2510-3. doi: 10.1021/jo052285+.

Abstract

Cytotoxicity-guided fractionation of the crude methanol extract of a marine sponge, Ircinia sp., yielded tedanolide C (1), a new 18-membered macrolide. The structure was solved by interpreting NMR and MS data, and the relative stereochemistry was determined from a combination of homo- and heteronuclear coupling constants in conjunction with molecular modeling. Compound 1 exhibited potent cytotoxicity against HCT-116 cells in vitro. Cell cycle analysis showed that treatment of cells with compound 1 arrested cells in the S-phase.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Cell Cycle / drug effects
  • Drug Screening Assays, Antitumor
  • HCT116 Cells
  • Humans
  • Macrolides / chemistry*
  • Macrolides / isolation & purification
  • Macrolides / pharmacology*
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Molecular Conformation
  • Porifera / chemistry*
  • Reference Standards
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Macrolides
  • tedanolide C