Viridamides A and B, lipodepsipeptides with antiprotozoal activity from the marine cyanobacterium Oscillatoria nigro-viridis.
Parallel chemical and phylogenetic investigation of a marine cyanobacterium from Panama led to the isolation of two new PKS-NRPS-derived compounds, viridamides A and B. Their structures were determined by NMR and mass spectroscopic methods, and the absolute configurations assigned by Marfey's method and chiral HPLC analysis. In addition to six standard, N-methylated amino and hydroxy acids, these metabolites contained the structurally novel 5-methoxydec-9-ynoic acid moiety and an unusual proline methyl ester terminus. Morphologically, this cyanobacterium was identified as Oscillatoria nigro-viridis, and its 16S rDNA sequence is reported here for the first time. Phylogenetic analysis of these sequence data has identified O. nigro-viridis strain OSC3L to be closely related to two other marine cyanobacterial genera, Trichodesmium and Blennothrix. Viridamide A showed antitrypanosomal activity with an IC50 of 1.1 microM and antileishmanial activity with an IC50 of 1.5 microM.
Simmons
T Luke
TL
Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, California 92093-0212, USA.
Engene
Niclas
N
Ureña
Luis David
LD
Romero
Luz I
LI
Ortega-Barría
Eduardo
E
Gerwick
Lena
L
Gerwick
William H
WH
D000818:Animals; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007894:Leishmania mexicana / Q000187:drug effects; D008386:Marine Biology; D015394:Molecular Structure; D010176:Panama; D010963:Plasmodium falciparum / Q000187:drug effects; D014349:Trypanosoma cruzi / Q000187:drug effects
D000981:Antiprotozoal Agents; D047630:Depsipeptides; C532611:viridamide A; C532612:viridamide B