Venturamides A and B: antimalarial constituents of the panamanian marine Cyanobacterium Oscillatoria sp.
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.
Linington
Roger G
RG
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California-San Diego, La Jolla, CA 92093, USA.
Gonzalez
José
J
Ureña
Luis-David
LD
Romero
Luz I
LI
Ortega-Barría
Eduardo
E
Gerwick
William H
WH
D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000458:Cyanobacteria / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007893:Leishmania donovani / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects; D014349:Trypanosoma cruzi / Q000187:drug effects; D014407:Tumor Cells, Cultured
D000962:Antimalarials; D010456:Peptides, Cyclic; C519248:venturamide A; C519249:venturamide B