Literature DB >> 20687534

The hoiamides, structurally intriguing neurotoxic lipopeptides from Papua New Guinea marine cyanobacteria.

Hyukjae Choi1, Alban R Pereira, Zhengyu Cao, Cynthia F Shuman, Niclas Engene, Tara Byrum, Teatulohi Matainaho, Thomas F Murray, Alfonso Mangoni, William H Gerwick.   

Abstract

Two related peptide metabolites, one a cyclic depsipeptide, <span class="Chemical">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 alpha-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 Ca(2+) oscillations with EC(50) values of 3.9 microM and 79.8 nM, respectively, while 3 had no significant effects in these assays.

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Year:  2010        PMID： 20687534      PMCID： PMC3227549          DOI： 10.1021/np100468n

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


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