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

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.

• Authors: Haruhisa Kikuchi, Yoshinori Saito, Jun'ichi Sekiya, Yumiko Okano, Masaki Saito, Norimichi Nakahata, Yuzuru Kubohara, Yoshiteru Oshima
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 70 Issue 22 Pg. 8854-8 (Oct 28 2005) ISSN: 0022-3263 [Print] United States
• PMID: 16238318 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Amides
• Phenols
• brefelamide

Topics

• Amides (chemical synthesis, chemistry, 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, chemistry, isolation & purification)