Venturamides A and B: antimalarial constituents of the panamanian marine Cyanobacterium Oscillatoria sp

J Nat Prod. 2007 Mar;70(3):397-401. doi: 10.1021/np0605790. Epub 2007 Mar 1.

Abstract

Two new modified cyclic hexapeptides, venturamides A (1) and B (2), were isolated from the marine cyanobacterium Oscillatoria sp. by antimalarial bioassay-guided fractionation. The isolation of 1 and 2 represents the first example of the identification of cyanobacterial peptides with selective antimalarial activity. The planar structures of 1 and 2 were determined by 1D and 2D NMR analyses and, in the case of venturamide A (1), comparison with the literature data for a previously reported synthetic compound. The absolute configuration of the amino acid residues was determined by selective hydrolysis in conjunction with Marfey's analysis. Compounds 1 and 2 were tested for biological activity against a range of tropical parasites.

Publication types

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

MeSH terms

  • Animals
  • Antimalarials* / chemistry
  • Antimalarials* / isolation & purification
  • Antimalarials* / pharmacology
  • Cyanobacteria / chemistry*
  • Drug Screening Assays, Antitumor
  • Humans
  • Leishmania donovani / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic* / chemistry
  • Peptides, Cyclic* / isolation & purification
  • Peptides, Cyclic* / pharmacology
  • Plasmodium falciparum / drug effects
  • Trypanosoma cruzi / drug effects
  • Tumor Cells, Cultured

Substances

  • Antimalarials
  • Peptides, Cyclic
  • venturamide A
  • venturamide B