Depsipeptide companeramides from a Panamanian marine cyanobacterium associated with the coibamide producer.

Abstract

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.

• Authors: Oliver B Vining, Rebecca A Medina, Edward A Mitchell, Patrick Videau, Dong Li, Jeffrey D Serrill, Jane X Kelly, William H Gerwick, Philip J Proteau, Jane E Ishmael, Kerry L McPhail
• Journal: Journal of natural products (J Nat Prod) Vol. 78 Issue 3 Pg. 413-20 (Mar 27 2015) ISSN: 1520-6025 [Electronic] United States
• PMID: 25562664 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)

Chemical References

• Antineoplastic Agents
• Depsipeptides
• companeramide A
• companeramide B
• romidepsin

Topics

• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Chromatography, High Pressure Liquid
• Cyanobacteria (chemistry)
• Depsipeptides (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Humans
• Molecular Structure
• Nuclear Magnetic Resonance, Biomolecular
• Panama