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

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

All Science Journal Classification (ASJC) codes

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

Fingerprint Dive into the research topics of 'The hoiamides, structurally intriguing neurotoxic Lipopeptides from Papua New Guinea marine cyanobacteria'. Together they form a unique fingerprint.

  • 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