Phylogeny-guided isolation of ethyl tumonoate A from the marine cyanobacterium cf. Oscillatoria margaritifera

J Nat Prod. 2011 Aug 26;74(8):1737-43. doi: 10.1021/np200236c. Epub 2011 Jul 13.

Abstract

The evolutionary relationships of cyanobacteria, as inferred by their SSU (16S) rRNA genes, were used as predictors of their potential to produce varied secondary metabolites. The evolutionary relatedness in geographically distant cyanobacterial specimens was then used as a guide for the detection and isolation of new variations of predicted molecules. This phylogeny-guided isolation approach for new secondary metabolites was tested in its capacity to direct the search for specific classes of new natural products from Curaçao marine cyanobacteria. As a result, we discovered ethyl tumonoate A (1), a new tumonoic acid derivative with anti-inflammatory activity and inhibitory activity of calcium oscillations in neocortical neurons.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Genes, rRNA
  • Humans
  • Marine Biology
  • Mice
  • Molecular Structure
  • Oscillatoria / chemistry*
  • Oscillatoria / genetics
  • Phylogeny*
  • Polymerase Chain Reaction
  • Proline / analogs & derivatives*
  • Proline / chemistry
  • Proline / isolation & purification*
  • Proline / pharmacology

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • ethyl tumonoate A
  • Proline