Tausalarin C: a new bioactive marine sponge-derived nitrogenous bismacrolide

Org Lett. 2009 Aug 20;11(16):3538-41. doi: 10.1021/ol9011019.

Abstract

A novel nitrogenous bismacrolide, designated tausalarin C (1), was isolated from the Madagascar sponge Fascaplysinopsis sp. The structure of the compound was elucidated by interpretation of MS and 1D and 2D NMR spectra. It is suggested that tausalarin C is assembled from salarin A (2) and pretaumycin A. The relative configuration of the chiral centers of salarin A was determined by X-ray diffraction. Tausalarin C was found to inhibit proliferation of K562 leukemia cells. A possible biogenesis is discussed.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Humans
  • K562 Cells
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / metabolism
  • Macrolides / pharmacology
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*

Substances

  • Antineoplastic Agents
  • Macrolides
  • salarin A
  • tausalarin C