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 › peer-review

77 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

All Science Journal Classification (ASJC) codes

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

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

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.",

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

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AU - Choi, Hyukjae

AU - Pereira, Alban R.

AU - Cao, Zhengyu

AU - Shuman, Cynthia F.

AU - Engene, Niclas

AU - Byrum, Tara

AU - Matainaho, Teatulohi

AU - Murray, Thomas F.

AU - Mangoni, Alfonso

AU - Gerwick, William H.

PY - 2010/8/27

Y1 - 2010/8/27

N2 - 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.

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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JF - Journal of Natural Products

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

Abstract

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