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

TitleDepsipeptide companeramides from a Panamanian marine cyanobacterium associated with the coibamide producer
Publication TypeJournal Article
Year of Publication2015
AuthorsVining O.B, Medina R.A, Mitchell E.A, Videau P., Li D., Serrill J.D, Kelly J.X, Gerwick WH, Proteau P.J, Ishmael J.E, McPhail K.L
JournalJournal of Natural Products
Volume78
Pagination413-420
Date Published2015/03
Type of ArticleArticle
ISBN Number0163-3864
Accession NumberWOS:000352033900011
Keywordscytotoxic cyclic depsipeptide; inhibitor; lyngbya-majuscula; Mollusk; onchidin; peptides; plasmodium-falciparum; potent; symplostatin 4
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 a-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.

DOI10.1021/np5007907
Short TitleJ. Nat. Prod.
Student Publication: 
No
Research Topics: 
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