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

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

doi:10.1021/np100468n

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

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

Department of Pharmacology and Neuroscience

Research output: Contribution to journal › Article

56 Scopus citations

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 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.

Original language	English (US)
Pages (from-to)	1411-1421
Number of pages	11
Journal	Journal of Natural Products
Volume	73
Issue number	8
DOIs	https://doi.org/10.1021/np100468n
State	Published - Aug 27 2010

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All Science Journal Classification (ASJC) codes

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

Cite this

Choi, H., Pereira, A. R., Cao, Z., Shuman, C. F., Engene, N., Byrum, T., Matainaho, T., Murray, T. F., Mangoni, A., & Gerwick, W. H. (2010). The hoiamides, structurally intriguing neurotoxic Lipopeptides from Papua New Guinea marine cyanobacteria. Journal of Natural Products, 73(8), 1411-1421. https://doi.org/10.1021/np100468n

The hoiamides, structurally intriguing neurotoxic Lipopeptides from Papua New Guinea marine cyanobacteria. / Choi, Hyukjae; Pereira, Alban R.; Cao, Zhengyu; Shuman, Cynthia F.; Engene, Niclas; Byrum, Tara; Matainaho, Teatulohi; Murray, Thomas F.; Mangoni, Alfonso; Gerwick, William H.

In: Journal of Natural Products, Vol. 73, No. 8, 27.08.2010, p. 1411-1421.

Research output: Contribution to journal › Article

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AU - Engene, Niclas

AU - Byrum, Tara

AU - Matainaho, Teatulohi

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AB - 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.

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10.1021/np100468n