|Title||Bouillonamide: A mixed polyketide-peptide cytotoxin from the marine cyanobacterium Moorea bouillonii|
|Publication Type||Journal Article|
|Year of Publication||2013|
|Authors||Tan L.T, Okino T., Gerwick WH|
|Type of Article||Article|
|Keywords||collection; cyanophyceae; cytotoxic; depsipeptide; discovery; drug; glycosidic macrolide; laingolide; lyngbya-bouillonii; marine cyanobacterium; metabolites; Moorea bouillonii; papua-new-guinea; polyketide-polypeptide; potent|
The tropical marine cyanobacterium, Moorea bouillonii, has gained recent attention as a rich source of bioactive natural products. Continued chemical investigation of this cyanobacterium, collected from New Britain, Papua New Guinea, yielded a novel cytotoxic cyclic depsipeptide, bouillonamide (1), along with previously reported molecules, ulongamide A and apratoxin A. Planar structure of bouillonamide was established by extensive 1D and 2D NMR experiments, including multi-edited HSQC, TOCSY, HBMC, and ROESY experiments. In addition to the presence of alpha-amino acid residues, compound 1 contained two unique polyketide-derived moieties, namely a 2-methyl-6-methylamino-hex-5-enoic acid (Mmaha) residue and a unit of 3-methyl-5-hydroxy-heptanoic acid (Mhha). Absolute stereochemistry of the alpha-amino acid units in bouillonamide was determined mainly by Marfey's analysis. Compound 1 exhibited mild toxicity with IC50's of 6.0 mu M against the neuron 2a mouse neuroblastoma cells.
|Short Title||Mar. Drugs|