title: Apratoxin D, a potent cytotoxic cyclodepsipeptide from papua new guinea collections of the marine cyanobacteria Lyngbya majuscula and Lyngbya sordida.
abstract: Cancer cell toxicity-guided fractionation of extracts of the Papua New Guinea marine cyanobacteria Lyngbya majuscula and Lyngbya sordida led to the isolation of apratoxin D (1). Compound 1 contains the same macrocycle as apratoxins A and C but possesses the novel 3,7-dihydroxy-2,5,8,10,10-pentamethylundecanoic acid as the polyketide moiety. The planar structures and stereostructures of compound 1 were determined by extensive 1D and 2D NMR and MS data analyses and by comparison with the spectroscopic data of apratoxins A and C. Apratoxin D (1) showed potent in vitro cytotoxicity against H-460 human lung cancer cells with an IC 50 value of 2.6 nM.
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, USA.
authors.forename: Marcelino
authors.initials: M
authors.lastname: Gutiérrez
authors.forename: Takashi L
authors.initials: TL
authors.lastname: Suyama
authors.forename: Niclas
authors.initials: N
authors.lastname: Engene
authors.forename: Joshua S
authors.initials: JS
authors.lastname: Wingerd
authors.forename: Teatulohi
authors.initials: T
authors.lastname: Matainaho
authors.forename: William H
authors.initials: WH
authors.lastname: Gerwick
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008235:Lyngbya Toxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008387:Marine Toxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010219:Papua New Guinea
chemical_list: D000970:Antineoplastic Agents; D047630:Depsipeptides; D008235:Lyngbya Toxins; D008387:Marine Toxins; C531298:apratoxin D