Isolation and synthesis of a new aromatic compound, brefelamide, from dictyostelium cellular slime molds and its inhibitory effect on the proliferation of astrocytoma cells

J Org Chem. 2005 Oct 28;70(22):8854-8. doi: 10.1021/jo051352x.

Abstract

[structure: see text] We have explored the diversity of secondary metabolites produced by cellular slime molds to examine the possible use of such cellular slime molds as a resource for novel drug development. A new aromatic amide, brefelamide (1), was isolated from methanol extracts of the fruiting bodies of Dictyostelium brefeldianum and D. giganteum. The structure of 1 was determined by spectral means including EIMS and (1)H and (13)C NMR. The total synthesis of 1 was carried out to confirm the structure and obtain sufficient samples for performing biological evaluation. Interestingly, compound 1 inhibited the cellular proliferation of 1321N1 human astrocytoma cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amides / isolation & purification*
  • Animals
  • Astrocytoma / pathology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dictyosteliida / chemistry*
  • Dictyostelium / chemistry*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Phenols / isolation & purification*

Substances

  • Amides
  • Phenols
  • brefelamide