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

Research output: Contribution to journalArticle

56 Citations (Scopus)

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 languageEnglish
Pages (from-to)1411-1421
Number of pages11
JournalJournal of Natural Products
Volume73
Issue number8
DOIs
StatePublished - Aug 27 2010

Fingerprint

Depsipeptides
Lipopeptides
Papua New Guinea
Cyanobacteria
Metabolites
Polyketides
Thiazoles
Isoleucine
Chromatography
Methionine
Neurons
Assays
Spectrum Analysis
Acetates
Sodium
Spectroscopy
Peptides
C 15
hoiamide B
hoiamide C

All Science Journal Classification (ASJC) codes

  • Drug Discovery
  • Pharmacology
  • Pharmaceutical Science
  • Analytical Chemistry
  • Organic Chemistry
  • Molecular Medicine
  • Complementary and alternative medicine
  • Medicine(all)

Cite this

Choi, H., Pereira, A. R., Cao, Z., Shuman, C. F., Engene, N., Byrum, T., ... 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 journalArticle

Choi, H, Pereira, AR, Cao, Z, Shuman, CF, Engene, N, Byrum, T, Matainaho, T, Murray, TF, Mangoni, A & Gerwick, WH 2010, 'The hoiamides, structurally intriguing neurotoxic Lipopeptides from Papua New Guinea marine cyanobacteria', Journal of Natural Products, vol. 73, no. 8, pp. 1411-1421. https://doi.org/10.1021/np100468n
Choi, Hyukjae ; Pereira, Alban R. ; Cao, Zhengyu ; Shuman, Cynthia F. ; Engene, Niclas ; Byrum, Tara ; Matainaho, Teatulohi ; Murray, Thomas F. ; Mangoni, Alfonso ; Gerwick, William H. / The hoiamides, structurally intriguing neurotoxic Lipopeptides from Papua New Guinea marine cyanobacteria. In: Journal of Natural Products. 2010 ; Vol. 73, No. 8. pp. 1411-1421.
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