The Hoiamides, Structurally Intriguing Neurotoxic Lipopeptides from Papua New Guinea Marine Cyanobacteria
journal contributionposted on 27.08.2010 by Hyukjae Choi, Alban R. Pereira, Zhengyu Cao, Cynthia F. Shuman, Niclas Engene, Tara Byrum, Teatulohi Matainaho, Thomas F. Murray, Alfonso Mangoni, William H. Gerwick
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Two related peptide metabolites, one a cyclic depsipeptide, hoiamide B (2), and the other a linear lipopeptide, hoiamide C (3), were isolated from two different collections of marine cyanobacteria obtained in Papua New Guinea. Their structures were elucidated by combining various techniques in spectroscopy, chromatography, and synthetic chemistry. Both metabolites belong to the unique hoiamide structural class, characterized by possessing an acetate extended and S-adenosyl methionine modified isoleucine unit, a central triheterocyclic system comprised of two α-methylated thiazolines and one thiazole, and a highly oxygenated and methylated C-15 polyketide unit. In neocortical neurons, the cyclic depsipeptide 2 stimulated sodium influx and suppressed spontaneous Ca2+ oscillations with EC50 values of 3.9 μM and 79.8 nM, respectively, while 3 had no significant effects in these assays.