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

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 microM and 79.8 nM, respectively, while 3 had no significant effects in these assays.

• Publication year

  2010

• Venue

  Journal of Natural Products

• Publication date

  2010-08-27

• Fields of study

  Biology, Medicine, Chemistry, Environmental Science

• Identifiers
  DOI 10.1021/np100468nPMID 20687534PMCID PMC3227549
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Hoiamide a, a sodium channel activator of unusual architecture from a consortium of two papua new Guinea cyanobacteria.

  2009cited by this paper
• New tricks from ancient algae: natural products biosynthesis in marine cyanobacteria.

  2009cited by this paper
• AWTY (are we there yet?): a system for graphical exploration of MCMC convergence in Bayesian phylogenetics

  2008cited by this paper
• Cloning and biochemical characterization of the hectochlorin biosynthetic gene cluster from the marine cyanobacterium Lyngbya majuscula.

  2007cited by this paper
• Voltage-gated ion channels and gating modifier toxins.

  2007cited by this paper
• A functional genomics approach to the mode of action of apratoxin A

  2006cited by this paper
• Biosynthesis and transformation of homoanatoxin-a in the cyanobacterium Raphidiopsis mediterranea Skuja and structures of three new homologues.

  2004cited by this paper
• MUSCLE: multiple sequence alignment with high accuracy and high throughput.

  2004cited by this paper
• Brevetoxin activation of voltage‐gated sodium channels regulates Ca2+ dynamics and ERK1/2 phosphorylation in murine neocortical neurons

  2004cited by this paper
• Spontaneous synchronized calcium oscillations in neocortical neurons in the presence of physiological [Mg(2+)]: involvement of AMPA/kainate and metabotropic glutamate receptors.

  2004cited by this paper
• MrBayes 3: Bayesian phylogenetic inference under mixed models

  2003cited by this paper
• A simple, fast, and accurate algorithm to estimate large phylogenies by maximum likelihood.

  2003cited by this paper
• The Comparative RNA Web (CRW) Site: an online database of comparative sequence and structure information for ribosomal, intron, and other RNAs

  2002cited by this paper
• Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly.

  2002cited by this paper
• Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula.

  2001cited by this paper
• Structure, function and pharmacology of voltage-gated sodium channels

  2000cited by this paper
• Voltage-gated sodium channels as therapeutic targets.

  2000cited by this paper
• Synthesis and gas chromatography/mass spectrometry analysis of stereoisomers of 2-hydroxy-3-methylpentanoic acid.

  2000cited by this paper
• Structure, Synthesis, and Biological Properties of Kalkitoxin, a Novel Neurotoxin from the Marine Cyanobacterium Lyngbya majuscula

  2000cited by this paper
• Molecular mechanisms of neurotoxin action on voltage-gated sodium channels.

  2000cited by this paper
• MODELTEST: testing the model of DNA substitution

  1998cited by this paper
• A Nonempirical Method Using LC/MS for Determination of the Absolute Configuration of Constituent Amino Acids in a Peptide: Combination of Marfey's Method with Mass Spectrometry and Its Practical Application

  1997cited by this paper
• Na+ channels as targets for neuroprotective drugs.

  1995cited by this paper
• Antillatoxin: An Exceptionally Ichthyotoxic Cyclic Lipopeptide from the Tropical Cyanobacterium Lyngbya majuscula

  1995cited by this paper
• Characterization of the interaction of the marine cyanobacterial natural product curacin A with the colchicine site of tubulin and initial structure-activity studies with analogues.

  1995cited by this paper
• Structure of Curacin A, a Novel Antimitotic, Antiproliferative and Brine Shrimp Toxic Natural Product from the Marine Cyanobacterium Lyngbya majuscula

  1994cited by this paper
• Majusculamides A and B, two epimeric lipodipeptides from Lyngbya majuscula Gomont

  1977cited by this paper

• Natural Cyclic Peptides: Synthetic Strategies and Biomedical Applications

  2025cites this paper
• K2CO3 Promoted Spirocyclopropanation of Thiazole‐Derived Oxadienes via 1,4‐Addition‐Induced Dearomatization Reaction

  2024cites this paper
• Chemical diversity of cyanobacterial natural products.

  2024cites this paper
• The potential of marine natural products and their synthetic derivatives as drugs targeting ion channels.

  2024cites this paper
• A Review of the Antimicrobial Properties of Cyanobacterial Natural Products

  2023cites this paper
• Marine Organisms as a Prolific Source of Bioactive Depsipeptides

  2023influential citation
• Recent asymmetric synthesis of natural products bearing an α-tertiary amine moiety via temporary chirality induction strategies.

  2023cites this paper
• Nanosynthesis, phycochemical constituents, and pharmacological properties of cyanobacterium Oscillatoria sp.

  2023cites this paper
• Enhancement of Anticancer, Antibacterial, and Acetylcholinesterase Inhibition Activities from Oscillatoria sancta under Starvation Conditions

  2023cites this paper
• Therapeutics from Cyanobacteria: A Review of Cyanobacteria-Derived Compounds as Anti-cancer Drug Leads

  2023cites this paper
• Special Issue in Honor of Professor William Gerwick.

  2022cites this paper
• Post-translational backbone-acyl shift yields natural product-like peptides bearing hydroxyhydrocarbon units.

  2022cites this paper
• Recent progression of cyanobacteria and their pharmaceutical utility: an update

  2022influential citation
• Anti-lung cancer properties of cyanobacterial bioactive compounds

  2022cites this paper
• Targeted Discovery of Amantamide B, an Ion Channel Modulating Nonapeptide from a South China Sea Oscillatoria Cyanobacterium.

  2022cites this paper
• A comprehensive review of chemistry and pharmacological aspects of natural cyanobacterial azoline-based circular and linear oligopeptides.

  2021cites this paper
• Potential use of nuisance cyanobacteria as a source of anticancer agents

  2021cites this paper
• A Multi-Omics Characterization of the Natural Product Potential of Tropical Filamentous Marine Cyanobacteria

  2021cites this paper
• Natural Cyclopeptides as Anticancer Agents in the Last 20 Years

  2021cites this paper
• The intriguing chemistry and biology of sulfur-containing natural products from marine microorganisms (1987–2020)

  2021cites this paper
• Mechanistic study on the NHC-catalyzed [3+4] annulation of enals and thiazolones

  2021cites this paper
• Phormidepistatin from the Cyanobacterium UIC 10484: Assessing the Phylogenetic Distribution of the Statine Pharmacophore.

  2021cites this paper
• Thiazoles

  2021cites this paper
• Odookeanynes A and B, Acetylene-Containing Lipopeptides from an Okeania sp. Marine Cyanobacterium.

  2021cites this paper
• Immunomodulating polysaccharide complexes and antioxidant metabolites from Anabaena laxa, Oscillatoria limosa and Phormidesmis molle

  2021cites this paper
• Voltage-Gated Sodium Channels: A Prominent Target of Marine Toxins

  2021cites this paper
• Cyanobacterial peptides with respect to anticancer activity: Structural and functional perspective

  2020cites this paper
• Cyanobacteria: a potential source of anticancer drugs

  2020cites this paper
• Marine Photosynthetic Microorganisms

  2020cites this paper
• The use of cyanobacterial metabolites as natural medical and biotechnological tools: review article

  2020cites this paper
• Cyanobacterial bioactive metabolites-A review of their chemistry and biology.

  2019cites this paper
• Heteroaryl Rings in Peptide Macrocycles.

  2019cites this paper
• Total Synthesis of Hoiamide A Using an Evans-Tishchenko Reaction as a Key Step.

  2019cites this paper
• Expression of Secondary Metabolite Gene Clusters and Production of Secondary Metabolites in Three Nostoc strains Subjected to Deprivation on Nutrients and Competition

  2019cites this paper
• Bifunctional Squaramide‐Catalysed Asymmetric Michael/Hemiketalization/Retro‐Aldol Reaction of Unsaturated Thiazolones with α‐Nitroketones: Synthesis of Chiral 4‐Acyloxythiazole Derivatives

  2019cites this paper
• The asymmetric construction of CF3-containing spiro-thiazolone-pyrrolidine compounds via [3 + 2] cycloaddition.

  2019cites this paper
• Cyanobacterial bioactive metabolites-A review of their chemistry and biology.

  2019cites this paper
• Enantioselective Michael addition of 3-ethyl carboxylate substituted pyrazolones to 5-alkenyl thiazolones catalyzed by squaramide organocatalyst

  2018cites this paper
• Jizanpeptins, Cyanobacterial Protease Inhibitors from a Symploca sp. Cyanobacterium Collected in the Red Sea.

  2018cites this paper
• Divergent Synthesis of Revised Apratoxin E, 30-epi-Apratoxin E, and 30S/30R-Oxoapratoxin E.

  2017cites this paper
• A Maldiisotopic Approach to Discover Natural Products: Cryptomaldamide, a Hybrid Tripeptide from the Marine Cyanobacterium Moorea producens.

  2017cites this paper
• Uncovering Potential Applications of Cyanobacteria and Algal Metabolites in Biology, Agriculture and Medicine: Current Status and Future Prospects

  2017cites this paper
• Cyanobacterial factories for the production of green energy and value-added products: An integrated approach for economic viability

  2017cites this paper
• Molecular Targets of Clinically Relevant Natural Products from Filamentous Marine Cyanobacteria

  2017cites this paper
• New Peptides Isolated from Marine Cyanobacteria, an Overview over the Past Decade

  2017cites this paper
• Investigação química e biológica de microrganismos marinhos e o uso de redes moleculares como ferramenta na busca por substâncias bioativas em cianobactérias marinhas do gênero Symploca

  2016cites this paper
• N-Heterocyclic Carbene-Catalyzed [3 + 4] Annulation of Enals and Alkenyl Thiazolones: Enantioselective Synthesis of Thiazole-Fused ε-Lactones.

  2016cites this paper
• Studies toward asymmetric synthesis of hoiamides A and B

  2016cites this paper
• Cytotoxic 1,3-Thiazole and 1,2,4-Thiadiazole Alkaloids from Penicillium oxalicum: Structural Elucidation and Total Synthesis

  2016cites this paper
• Bioactive thiazole and benzothiazole derivatives.

  2015cites this paper
• Marine Cyanobacteria Compounds with Anticancer Properties: Implication of Apoptosis

  2015cites this paper
• Biological targets and mechanisms of action of natural products from marine cyanobacteria.

  2015cites this paper
• Structures and Biological Activities of Novel Biselyngbyaside Analogs Isolated from the Marine Cyanobacterium Lyngbya sp.

  2015cites this paper
• Central Nervous System Modulators from the Oceans

  2015cites this paper
• Involvement of JNK and Caspase Activation in Hoiamide A-Induced Neurotoxicity in Neocortical Neurons

  2015cites this paper
• Caldora penicillata gen. nov., comb. nov. (Cyanobacteria), a pantropical marine species with biomedical relevance

  2015cites this paper
• Solvent effect and fluorescence response of the 7-tert-butylpyrene-dipicolylamine linkage for the selective and sensitive response toward Zn(II) and Cd(II) ions

  2015cites this paper
• Inhibition of glutamate regulated calcium entry into leukemic megakaryoblasts reduces cell proliferation and supports differentiation.

  2015cites this paper
• Biosynthesis of the 4-methyloxazoline-containing nonribosomal peptides, JBIR-34 and -35, in Streptomyces sp. Sp080513GE-23.

  2014cites this paper
• Kurahyne, an acetylene-containing lipopeptide from a marine cyanobacterial assemblage of Lyngbya sp.

  2014cites this paper
• Recent progress in neuroactive marine natural products.

  2014cites this paper
• Chapter 8 - Marine Resource: A Promising Future for Anticancer Drugs

  2013cites this paper
• Shellfish Toxins Targeting Voltage-Gated Sodium Channels

  2013influential citation
• Cyanobacteria: potential candidates for drug discovery

  2013cites this paper
• Recent advances in marine drug research.

  2013cites this paper
• Long-range proton-carbon coupling constants: NMR methods and applications.

  2013cites this paper
• Muscarine, imidaozle, oxazole and thiazole alkaloids.

  2013cites this paper
• Marine natural products.

  2013cites this paper
• Nonproteinogenic amino acid building blocks for nonribosomal peptide and hybrid polyketide scaffolds.

  2013cites this paper
• Cyanobacterial Toxins in Food-Webs: Implications for Human and Environmental Health

  2013cites this paper
• Marine Cyanobacteria: A Prolific Source of Bioactive Natural Products as Drug Leads

  2013cites this paper
• Nichtproteinogene Aminosäurebausteine für Peptidgerüste aus nichtribosomalen Peptiden und hybriden Polyketiden

  2013cites this paper
• Phylogenetic Inferences Reveal a Large Extent of Novel Biodiversity in Chemically Rich Tropical Marine Cyanobacteria

  2013cites this paper
• Santacruzamate A, a potent and selective histone deacetylase inhibitor from the Panamanian marine cyanobacterium cf. Symploca sp.

  2013cites this paper
• Marine Pharmacology in 2009–2011: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and other Miscellaneous Mechanisms of Action †

  2013cites this paper
• Isolation and structures of biselyngbyasides B, C, and D from the marine cyanobacterium Lyngbya sp., and the biological activities of biselyngbyasides

  2012cites this paper
• Microwave-assisted hydrolysis: efficient synthesis of α-substituted cysteines on multi-gram scale

  2012cites this paper
• Solvent‐Free Tandem Synthesis of 2‐Thiazolines and 2‐Oxazolines Catalyzed by a Copper Catalyst

  2012cites this paper
• Stereoselective synthesis of the common polyketide fragment of hoiamides

  2012cites this paper
• Biselyngbyolide A, a Novel Cytotoxic Macrolide from the Marine Cyanobacterium Lyngbya sp.

  2012cites this paper
• Chapter 4 - Marine Cyanobacteria: A Treasure Trove of Bioactive Secondary Metabolites for Drug Discovery

  2012cites this paper
• A review of pharmacological and toxicological potentials of marine cyanobacterial metabolites

  2012cites this paper
• Marine Cyanobacteria Compounds with Anticancer Properties: A Review on the Implication of Apoptosis

  2012influential citation
• Tetramethylenedisulfotetramine alters Ca²⁺ dynamics in cultured hippocampal neurons: mitigation by NMDA receptor blockade and GABA(A) receptor-positive modulation.

  2012cites this paper
• Marine natural products.

  2012cites this paper
• Biosynthetically intriguing chlorinated lipophilic metabolites from geographically distant tropical marine cyanobacteria.

  2012cites this paper
• Marine natural products.

  2012cites this paper
• Hoiamide D, a marine cyanobacteria-derived inhibitor of p53/MDM2 interaction.

  2012cites this paper
• A Cytotoxic Fellutamide Analogue from the Sponge-Derived Fungus Aspergillus versicolor.

  2011cites this paper
• Total synthesis of hoiamide C.

  2011cites this paper
• Five-Membered Ring Systems: With N and S (Se) Atoms

  2011cites this paper
• Biologically active secondary metabolites from marine cyanobacteria.

  2010cites this paper
• Do Cytochrome P450 Enzymes Contribute to the Metabolism of Xenobiotics in Human

  2010cites this paper