title: Bouillonamide: a mixed polyketide-peptide cytotoxin from the marine cyanobacterium Moorea bouillonii.
abstract: 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 α-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 α-amino acid units in bouillonamide was determined mainly by Marfey's analysis. Compound 1 exhibited mild toxicity with IC50's of 6.0 µM against the neuron 2a mouse neuroblastoma cells.
authors: Natural Sciences and Science Education, National Institute of Education, Nanyang Technological University, 1 Nanyang Walk, 637616, Singapore. liktong.tan@nie.edu.sg
authors: Lik Tong
authors: LT
authors: Tan
authors: Tatsufumi
authors: T
authors: Okino
authors: William H
authors: WH
authors: Gerwick
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D009447:Neuroblastoma / Q000188:drug therapy* / Q000473:pathology; D010219:Papua New Guinea; D061065:Polyketides / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D047630:Depsipeptides; D061065:Polyketides; C586885:bouillonamide A
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