The Hoiamides, Structurally Intriguing Neurotoxic Lipopeptides from Papua New Guinea Marine Cyanobacteria

Title
The Hoiamides, Structurally Intriguing Neurotoxic Lipopeptides from Papua New Guinea Marine Cyanobacteria
Author(s)
최혁재Alban R. Pereira[Alban R. Pereira]Zhengyu Cao[Zhengyu Cao]Cynthia F. Shuman[Cynthia F. Shuman]Niclas Engene[Niclas Engene]Tara Byrum[Tara Byrum]Teatulohi Matainaho[Teatulohi Matainaho]Thomas F. Murray[Thomas F. Murray]Alfonso Mangoni[Alfonso Mangoni]William H. Gerwick[William H. Gerwick]
Keywords
GATED SODIUM-CHANNELS; LYNGBYA-MAJUSCULA; NEOCORTICAL NEURONS; NATURAL-PRODUCT; APRATOXIN-A; CURACIN-A; HECTOCHLORIN; SPECTROMETRY; TARGETS; POTENT
Issue Date
201008
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF NATURAL PRODUCTS, v.73, no.8, pp.1411 - 1421
Abstract
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 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 mu M and 79.8 nM, respectively, while 3 had no significant effects in these assays.
URI
http://hdl.handle.net/YU.REPOSITORY/23884http://dx.doi.org/10.1021/np100468n
ISSN
0163-3864
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약학대학 > 약학부 > Articles
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