New convulsive compounds, brasiliamides A and B, from Penicillium brasilianum batista JV-379

Biosci Biotechnol Biochem. 2002 Aug;66(8):1697-705. doi: 10.1271/bbb.66.1697.

Abstract

New convulsive compounds, brasiliamides A (1) and B (2), were isolated by activity-guided fractionation from okara fermented with a soil isolate of Penicillium brasilianum Batista JV-379. Their structures were elucidated on the basis of spectral and chemical evidence and by X-ray crystallography of the hydrogenated product of 2. In the 1H- and 13C-NMR spectra of 2, the signals were complicated, all being doubled or broadened in several deuterated solvents at room temperature. The conformational change of 2 was clarified as the rotational isomerization of amide bonds in solution by NMR measurements at various temperatures. Four rotamers of 2 at two amide bonds were presented at -60 degrees C in CDCl3, whereas only two isomers were apparent at room temperature, owing to rapid rotation of one of the amide bonds. Brasiliamides A and B respectively showed convulsive activity against silkworms with ED50 values of 300 and 50 microg/g of diet.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biological Assay
  • Bombyx / metabolism
  • Chromatography, Gel
  • Convulsants / chemistry*
  • Convulsants / isolation & purification
  • Convulsants / pharmacology
  • Crystallography, X-Ray
  • Dioxoles / chemistry*
  • Dioxoles / isolation & purification
  • Dioxoles / pharmacology
  • Models, Molecular
  • Molecular Conformation
  • Nuclear Magnetic Resonance, Biomolecular
  • Penicillium / chemistry*
  • Penicillium / metabolism
  • Pyrazines / chemistry*
  • Pyrazines / isolation & purification
  • Pyrazines / pharmacology
  • Soil Microbiology
  • Stereoisomerism

Substances

  • Convulsants
  • Dioxoles
  • Pyrazines
  • brasiliamide A
  • brasiliamide B