Depsipeptide Companeramides from a Panamanian Marine Cyanobacterium Associated with the Coibamide Producer

Two new cyclic depsipeptides, companeramides A (1) and B (2), have been isolated from the phylogenetically characterized cyanobacterial collection that yielded the previously reported cancer cell toxin coibamide A (collected from Coiba Island, Panama). The planar structures of the companeramides, which contain 3-amino-2-methyl-7-octynoic acid (Amoya), hydroxy isovaleric acid (Hiva), and eight α-amino acid units, were established by NMR spectroscopy and mass spectrometry. The absolute configuration of each companeramide was assigned using a combination of Marfey’s methodology and chiral-phase HPLC analysis of complete and partial hydrolysis products compared to commercial and synthesized standards. Companeramides A (1) and B (2) showed high nanomolar in vitro antiplasmodial activity but were not overtly cytotoxic to four human cancer cell lines at the doses tested.

• Publication year

  2015

• Venue

  Journal of Natural Products

• Publication date

  2015-01-06

• Fields of study

  Biology, Medicine, Chemistry, Environmental Science

• Identifiers
  DOI 10.1021/np5007907PMID 25562664PMCID 4380200
• 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.

• Plos One

  2015cited by this paper
• Coibamide A Induces mTOR-Independent Autophagy and Cell Death in Human Glioblastoma Cells

  2013cited by this paper
• Apratoxin H and apratoxin A sulfoxide from the Red Sea cyanobacterium Moorea producens.

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

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

  2013cited by this paper
• The antimalarial natural product symplostatin 4 is a nanomolar inhibitor of the food vacuole falcipains.

  2012cited by this paper
• Coibacins A-D, antileishmanial marine cyanobacterial polyketides with intriguing biosynthetic origins.

  2012cited by this paper
• Cyclic depsipeptides, grassypeptolides D and E and Ibu-epidemethoxylyngbyastatin 3, from a Red Sea Leptolyngbya cyanobacterium.

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

  2010cited by this paper
• Antimalarial peptides from marine cyanobacteria: isolation and structural elucidation of gallinamide A.

  2009cited by this paper
• Journal of Natural Products简介

  2009cited by this paper
• New innovations for an old infection: antimalarial lead discovery from marine natural products during the period 2003-2008.

  2009cited by this paper
• Combinatorial Strategies by Marine Cyanobacteria: Symplostatin 4, an Antimitotic Natural Dolastatin 10/15 Hybrid that Synergizes with the Coproduced HDAC Inhibitor Largazole

  2009cited by this paper
• Coibamide A, a potent antiproliferative cyclic depsipeptide from the Panamanian marine cyanobacterium Leptolyngbya sp.

  2008cited by this paper
• Antimalarial linear lipopeptides from a Panamanian strain of the marine cyanobacterium Lyngbya majuscula.

  2007cited by this paper
• Design, Synthesis, and Evaluation of 10-N-Substituted Acridones as Novel Chemosensitizers in Plasmodium falciparum

  2007cited by this paper
• Toward the total synthesis of onchidin, a cytotoxic cyclic depsipeptide from a mollusc.

  2007cited by this paper
• Venturamides A and B: antimalarial constituents of the panamanian marine Cyanobacterium Oscillatoria sp.

  2007cited by this paper
• Simple and Inexpensive Fluorescence-Based Technique for High-Throughput Antimalarial Drug Screening

  2004cited by this paper
• Ulongapeptin, a cytotoxic cyclic depsipeptide from a Palauan marine cyanobacterium Lyngbya sp.

  2003cited by this paper
• The guineamides, novel cyclic depsipeptides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula.

  2003cited by this paper
• Effects of the antimitotic natural product dolastatin 10, and related peptides, on the human malarial parasite Plasmodium falciparum.

  2003cited by this paper
• Malevamides A-C, new depsipeptides from the marine cyanobacterium Symploca laete-viridis.

  2000cited by this paper
• Onchidin: a cytotoxic depsipeptide with C2 symmetry from a marine mollusc

  1994cited by this paper

• Cyclic peptides from cyanobacteria: Structural insights, biological functions, and mechanisms of cyclization

  2025cites this paper
• Chemical diversity of cyanobacterial natural products.

  2024cites this paper
• Modified peptides and organic metabolites of cyanobacterial origin with antiplasmodial properties

  2024cites this paper
• Harnessing Leptolyngbya for antiproliferative and antimicrobial metabolites through lens of modern techniques: A review

  2024cites this paper
• Secondary metabolites from cyanobacteria: source, chemistry, bioactivities, biosynthesis and total synthesis

  2024cites this paper
• Marine Natural Products as Novel Treatments for Parasitic Diseases.

  2024cites this paper
• Marine Cyanobacteria: A Rich Source of Structurally Unique Anti-Infectives for Drug Development

  2024cites this paper
• Marine organisms as potential sources of natural products for the prevention and treatment of malaria

  2023cites this paper
• Therapeutic Potential of Marine-Derived Cyclic Peptides as Antiparasitic Agents

  2023cites this paper
• Total Synthesis of Ikoamide, a Highly N-Methylated Antimalarial Lipopeptide.

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

  2023cites this paper
• Absolute Stereochemistry Determination of Bioactive Marine-Derived Cyclopeptides by Liquid Chromatography Methods: An Update Review (2018–2022)

  2023cites this paper
• Cyanobacterial secondary metabolites towards improved commercial significance through multiomics approaches

  2022cites this paper
• Phaeosphamides A and B, Cytotoxic Cyclodecadepsipeptides from the Mangrove-Derived Fungus Phaeosphaeriopsis sp. S296

  2022cites this paper
• Trends of antimalarial marine natural products: progresses, challenges and opportunities.

  2022cites this paper
• Chemical labeling strategies for small molecule natural product detection and isolation.

  2021cites this paper
• Portobelamides A and B and Caciqueamide, Cytotoxic Peptidic Natural Products from a Caldora sp. Marine Cyanobacterium.

  2021cites this paper
• Photo-induced radical thiol-ene chemistry: a versatile toolbox for peptide-based drug design.

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

  2020cites this paper
• Acetylene Group, Friend or Foe in Medicinal Chemistry.

  2020cites this paper
• Ikoamide, an Antimalarial Lipopeptide from an Okeania sp. Marine Cyanobacterium.

  2020cites this paper
• Structure elucidation of bacterial nonribosomal lipopeptides.

  2020cites this paper
• Iheyamides A-C, Antitrypanosomal Linear Peptides Isolated from a Marine Dapis sp. Cyanobacterium.

  2020cites this paper
• Marine Bioactive Peptides—An Overview of Generation, Structure and Application with a Focus on Food Sources

  2020cites this paper
• Bioactivities of Lyngbyabellins from Cyanobacteria of Moorea and Okeania Genera

  2020cites this paper
• Nanogram and Nanomolar Active Marine Antiplasmodial Antibiotics

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

  2020influential citation
• Metabolites from Marine Microorganisms, Micro, and Macroalgae: Immense Scope for Pharmacology

  2019cites this paper
• 1 Natural products from cyanobacteria : focus on 2 beneficial activities 3

  2019cites this paper
• Natural Products from Cyanobacteria: Focus on Beneficial Activities

  2019cites this paper
• Marine natural products as strategic prototypes in the development of a new generation of antimalarial agents

  2019cites this paper
• Trichophycin A, a Cytotoxic Linear Polyketide Isolated from a Trichodesmium thiebautii Bloom

  2019cites this paper
• Cyanobacterial peptides as a tour de force in the chemical space of antiparasitic agents.

  2019cites this paper
• Anti-infective Compounds from Marine Organisms

  2018cites this paper
• Cyanobacteria‐derived peptide antibiotics discovered since 2000

  2018cites this paper
• Medicinal Purposes: Bioactive Metabolites from Marine-derived Organisms.

  2018cites this paper
• Marine Natural Peptides: Determination of Absolute Configuration Using Liquid Chromatography Methods and Evaluation of Bioactivities

  2018cites this paper
• Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology.

  2018cites this paper
• Trichophycins B-F, Chlorovinylidene-Containing Polyketides Isolated from a Cyanobacterial Bloom.

  2018cites this paper
• Genetic diversity of benthic marine cyanophage as revealed by sequence analysis of various phage marker genes

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

  2017cites this paper
• Marine natural products.

  2017cites this paper
• Structural Diversity, Biological Properties and Applications of Natural Products from Cyanobacteria. A Review †

  2017cites this paper
• Bioactive and Membrane‐Permeable Cyclic Peptide Natural Products

  2017cites this paper
• Antibiotics from Gram-negative bacteria: a comprehensive overview and selected biosynthetic highlights.

  2017cites this paper
• Urumamide, a novel chymotrypsin inhibitor with a β-amino acid from a marine cyanobacterium Okeania sp.

  2016cites this paper
• Alkynyl-Containing Peptides of Marine Origin: A Review

  2016influential citation
• C3 and 2D C3 Marfey's Methods for Amino Acid Analysis in Natural Products.

  2016cites this paper
• Oryzamides A-E, Cyclodepsipeptides from the Sponge-Derived Fungus Nigrospora oryzae PF18.

  2016cites this paper
• Bastimolide A, a Potent Antimalarial Polyhydroxy Macrolide from the Marine Cyanobacterium Okeania hirsuta.

  2015cites this paper
• Anti-infective Natural Products from Cyanobacteria

  2015cites this paper