Bouillonamide: A mixed polyketide-peptide cytotoxin from the marine cyanobacterium Moorea bouillonii

TitleBouillonamide: A mixed polyketide-peptide cytotoxin from the marine cyanobacterium Moorea bouillonii
Publication TypeJournal Article
Year of Publication2013
AuthorsTan L.T, Okino T., Gerwick WH
JournalMarine Drugs
Volume11
Pagination3015-3024
Date Published2013/08
Type of ArticleArticle
ISBN Number1660-3397
Accession NumberWOS:000330521300021
Keywordscollection; cyanophyceae; cytotoxic; depsipeptide; discovery; drug; glycosidic macrolide; laingolide; lyngbya-bouillonii; marine cyanobacterium; metabolites; Moorea bouillonii; papua-new-guinea; polyketide-polypeptide; potent
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 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.

DOI10.3390/md11083015
Short TitleMar. Drugs
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