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

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.
AuthorsMohamed El-Naggar, Melissa Conte, Robert J Capon
JournalOrganic & biomolecular chemistry (Org Biomol Chem) Vol. 8 Issue 2 Pg. 407-12 (Jan 21 2010) ISSN: 1477-0539 [Electronic] England
PMID20066277 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Alkaloids
  • Macrolides
  • Saponins
  • mirabilin
  • Oleanolic Acid
Topics
  • Alkaloids (chemistry, isolation & purification, pharmacology)
  • Animals
  • Australia
  • Cell Line, Tumor
  • Humans
  • Inhibitory Concentration 50
  • Macrolides (chemistry)
  • Oleanolic Acid (analogs & derivatives, chemistry, isolation & purification, pharmacology)
  • Porifera (chemistry)
  • Saponins (chemistry, isolation & purification, pharmacology)
  • Spectrum Analysis

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