title: Malyngamide 2, an oxidized lipopeptide with nitric oxide inhibiting activity from a Papua New Guinea marine cyanobacterium.
abstract: A Papua New Guinea collection of the marine cyanobacterium cf. Lyngbya sordida yielded three known compounds as well as a new PKS-NRPS-derived malyngamide with anti-inflammatory and cytotoxic activity. Malyngamide 2 features an extensively oxidized cyclohexanone ring. Resolution of the ring core as a 6,8,9-triol rather then a 7,8,9-triol and relative configuration was based on chemical shift and bond geometry modeling in conjunction with homonuclear and heteronuclear coupling constants, NOE and ROE correlations, and other structural information. Malyngamide 2 exhibited anti-inflammatory activity in LPS-induced RAW macrophage cells (IC(50) = 8.0 μM) with only modest cytotoxicity to the mammalian cell line.
authors.affiliation: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California at San Diego, La Jolla, California 92093, United States.
authors.forename: Karla L
authors.initials: KL
authors.lastname: Malloy
authors.forename: Francisco A
authors.initials: FA
authors.lastname: Villa
authors.forename: Niclas
authors.initials: N
authors.lastname: Engene
authors.forename: Teatulohi
authors.initials: T
authors.lastname: Matainaho
authors.forename: Lena
authors.initials: L
authors.lastname: Gerwick
authors.forename: William H
authors.initials: WH
authors.lastname: Gerwick
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000458:Cyanobacteria / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor; D055666:Lipopeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors; D010219:Papua New Guinea
chemical_list: D000970:Antineoplastic Agents; D055666:Lipopeptides; D008070:Lipopolysaccharides; C557964:malyngamide 2; D009569:Nitric Oxide