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

Mar Drugs. 2013 Aug 19;11(8):3015-24. doi: 10.3390/md11083015.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / administration & dosage
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cyanobacteria / chemistry*
  • Depsipeptides / administration & dosage
  • Depsipeptides / isolation & purification
  • Depsipeptides / pharmacology*
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Mice
  • Neuroblastoma / drug therapy*
  • Neuroblastoma / pathology
  • Papua New Guinea
  • Polyketides / administration & dosage
  • Polyketides / isolation & purification
  • Polyketides / pharmacology

Substances

  • Antineoplastic Agents
  • Depsipeptides
  • Polyketides
  • bouillonamide A