Antimalarial peptides from marine cyanobacteria: isolation and structural elucidation of gallinamide A.
As part of a continuing program to identify novel treatments for neglected parasitic diseases, the Panama International Cooperative Biodiversity Group (ICBG) program has been investigating the antimalarial potential of secondary metabolites from Panamanian marine cyanobacteria. From over 60 strains of cyanobacteria evaluated in our biological screens, the organic extract of a Schizothrix species from a tropical reef near Piedras Gallinas (Caribbean coast of Panama) showed potent initial antimalarial activity against the W2 chloroquine-resistant strain of Plasmodium falciparum. Bioassay-guided fractionation followed by 2D NMR analysis afforded the planar structure of a new and highly functionalized linear peptide, gallinamide A. Subsequent degradation and derivatization methods were used to determine the absolute configuration at most stereogenic centers in this unusual new metabolite.
Linington
Roger G
RG
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, USA. rogerl@chemistry.ucsc.edu
Clark
Benjamin R
BR
Trimble
Erin E
EE
Almanza
Alejandro
A
Ureña
Luis-David
LD
Kyle
Dennis E
DE
Gerwick
William H
WH
D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D023181:Antimicrobial Cationic Peptides; D017691:Caribbean Region; D002738:Chloroquine / Q000494:pharmacology; D000458:Cyanobacteria / Q000737:chemistry*; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D021261:Parasitic Sensitivity Tests; D010455:Peptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010963:Plasmodium falciparum / Q000187:drug effects*
D000962:Antimalarials; D023181:Antimicrobial Cationic Peptides; D010455:Peptides; C534687:gallinamide A; D002738:Chloroquine