Coibamide A, a potent antiproliferative cyclic depsipeptide from the Panamanian marine cyanobacterium Leptolyngbya sp.
Coibamide A (1) is a new, potent antiproliferative depsipeptide which was isolated from a marine Leptolyngbya cyanobacterium collected from the Coiba National Park, Panama. The planar structure of 1 was elucidated by a combination of NMR spectroscopy and mass spectrometry. Exhaustive 1D and 2D NMR spectroscopy included natural abundance 15N and variable temperature experiments; mass spectrometry included TOF-ESI-MSn and FT-MSn experiments. Chemical degradation followed by chiral HPLC- and GC-MS analyses was used to assign the absolute configuration of 1. This highly methylated cyclized depsipeptide exhibited an unprecedented selectivity profile in the NCI 60 cancer cell line panel and appears to act via a novel mechanism.
Medina
Rebecca A
RA
College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, USA.
Goeger
Douglas E
DE
Hills
Patrice
P
Mooberry
Susan L
SL
Huang
Nelson
N
Romero
Luz I
LI
Ortega-Barría
Eduardo
E
Gerwick
William H
WH
McPhail
Kerry L
KL
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D018922:HL-60 Cells; D006801:Humans; D008175:Lung Neoplasms / Q000188:drug therapy; D051379:Mice; D019906:Nuclear Magnetic Resonance, Biomolecular; D021241:Spectrometry, Mass, Electrospray Ionization
D000970:Antineoplastic Agents; D047630:Depsipeptides; C530036:coibamide A