title: 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.affiliation: †Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, United States.
authors.forename: Oliver B
authors.initials: OB
authors.lastname: Vining
authors.affiliation: †Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, United States.
authors.forename: Rebecca A
authors.initials: RA
authors.lastname: Medina
authors.affiliation: †Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, United States.
authors.forename: Edward A
authors.initials: EA
authors.lastname: Mitchell
authors.affiliation: †Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, United States.
authors.forename: Patrick
authors.initials: P
authors.lastname: Videau
authors.affiliation: †Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, United States.
authors.forename: Dong
authors.initials: D
authors.lastname: Li
authors.affiliation: †Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, United States.
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: Serrill
authors.affiliation: ‡Veterans Affairs Medical Center, Portland, Oregon 97239, United States.
authors.forename: Jane X
authors.initials: JX
authors.lastname: Kelly
authors.affiliation: §Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, California 92093, United States.
authors.forename: William H
authors.initials: WH
authors.lastname: Gerwick
authors.affiliation: †Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, United States.
authors.forename: Philip J
authors.initials: PJ
authors.lastname: Proteau
authors.affiliation: †Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, United States.
authors.forename: Jane E
authors.initials: JE
authors.lastname: Ishmael
authors.affiliation: †Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, United States.
authors.forename: Kerry L
authors.initials: KL
authors.lastname: McPhail
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010176:Panama
chemical_list: D000970:Antineoplastic Agents; D047630:Depsipeptides; C000598546:companeramide A; C000598547:companeramide B; C087123:romidepsin