Antimalarial linear lipopeptides from a Panamanian strain of the marine cyanobacterium Lyngbya majuscula.
As part of the Panama International Cooperative Biodiversity Groups (ICBG) project, two new (2, 4) and two known (1, 3) linear alkynoic lipopeptides have been isolated from a Panamanian strain of the marine cyanobacterium Lyngbya majuscula. Carmabin A (1), dragomabin (2), and dragonamide A (3) showed good antimalarial activity (IC50 4.3, 6.0, and 7.7 microM, respectively), whereas the nonaromatic analogue, dragonamide B (4), was inactive. The planar structures of all four compounds were determined by NMR spectroscopy in combination with mass spectrometry, and their stereoconfigurations were established by chiral HPLC and by comparison of their optical rotations and NMR data with literature values.
McPhail
Kerry L
KL
College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, USA. kerry.mcphail@oregonstate.edu
Correa
Jhonny
J
Linington
Roger G
RG
Gonzalez
José
J
Ortega-Barría
Eduardo
E
Capson
Todd L
TL
Gerwick
William H
WH
D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002522:Chlorocebus aethiops; D000458:Cyanobacteria / Q000737:chemistry*; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010176:Panama; D010963:Plasmodium falciparum / Q000187:drug effects*; D014709:Vero Cells
D000962:Antimalarials; D009842:Oligopeptides; C112372:carmabin A; C521547:dragomabin; C521548:dragonamide B