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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 ?-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.

SUBMITTER: Vining OB 

PROVIDER: S-EPMC4380200 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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

Vining Oliver B OB   Medina Rebecca A RA   Mitchell Edward A EA   Videau Patrick P   Li Dong D   Serrill Jeffrey D JD   Kelly Jane X JX   Gerwick William H WH   Proteau Philip J PJ   Ishmael Jane E JE   McPhail Kerry L KL  

Journal of natural products 20150106 3

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 configurati  ...[more]

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