Mirabilins revisited: polyketide alkaloids from a southern Australian marine sponge, Clathria sp

Org Biomol Chem. 2010 Jan 21;8(2):407-12. doi: 10.1039/b915624k. Epub 2009 Oct 30.

Abstract

Chemical investigation of a southern Australian marine sponge, Clathria sp., yielded the known mirabilins C, F and G, together with three new analogues, mirabilins H-J. For the first time mirabilins C and F are documented as the underivatized natural products, and a complete absolute stereochemistry is assigned to mirabilin F. Mirabilin I represents the first member of this structure class to incorporate a trans-fused ring junction. Structures for all mirabilins are assigned on the basis of detailed spectroscopic analysis. A plausible polyketide origin is proposed, linking all mirabilins and related sponge alkaloids. Mirabilin cytotoxicity against several human cancer cell lines is discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • Australia
  • Cell Line, Tumor
  • Humans
  • Inhibitory Concentration 50
  • Macrolides / chemistry*
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / isolation & purification
  • Oleanolic Acid / pharmacology
  • Porifera / chemistry*
  • Saponins / chemistry*
  • Saponins / isolation & purification
  • Saponins / pharmacology*
  • Spectrum Analysis

Substances

  • Alkaloids
  • Macrolides
  • Saponins
  • mirabilin
  • Oleanolic Acid