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: Marcelino Gutiérrez, Takashi L Suyama, Niclas Engene, Joshua S Wingerd, Teatulohi Matainaho, William H Gerwick
• Journal: Journal of natural products (J Nat Prod) Vol. 71 Issue 6 Pg. 1099-103 (Jun 2008) ISSN: 1520-6025 [Electronic] United States
• PMID: 18444683 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)

Chemical References

• Antineoplastic Agents
• Depsipeptides
• Lyngbya Toxins
• Marine Toxins
• apratoxin D

Topics

• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Cyanobacteria (chemistry)
• Depsipeptides (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Humans
• Inhibitory Concentration 50
• Lyngbya Toxins (chemistry, isolation & purification, pharmacology)
• Marine Toxins (chemistry, isolation & purification, pharmacology)
• Molecular Structure
• Nuclear Magnetic Resonance, Biomolecular
• Papua New Guinea