Novel bioactive breviane spiroditerpenoids from Penicillium brevicompactum Dierckx

J Org Chem. 2000 Dec 29;65(26):9039-46. doi: 10.1021/jo0011078.

Abstract

The structures of four new, naturally occurring bioactive spiroditerpenoids, (+)-breviones B, C, D, and E, potential allelopathic agents, have been determined from extracts of semisolid fermented Penicillium brevicompactum Dierckx. The structures display the novel breviane spiroditerpenoid skeleton. Structure elucidation was performed by chemical transformations and by homo- and heteronuclear 2D-NMR spectral data. On the basis of combined studies of the theoretical conformations and NOEDIFF data, their relative stereochemistry is proposed. A mixed biogenesis for this novel family of spiroditerpenoids is tendered. The levels of activity shown by breviones B, C, and E in the etiolated wheat coleoptiles bioassay, especially breviones E (100% inhibition) and C (80% inhibition) both at 10(-4) M, suggest them as lead compounds for new agrochemicals.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Fermentation
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Models, Molecular
  • Penicillium / chemistry*
  • Penicillium / metabolism
  • Plant Growth Regulators / chemistry
  • Plant Growth Regulators / isolation & purification*
  • Plant Growth Regulators / pharmacology
  • Spectrophotometry, Infrared
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Spiro Compounds / pharmacology
  • Stereoisomerism
  • Triticum / drug effects
  • Triticum / growth & development

Substances

  • Diterpenes
  • Plant Growth Regulators
  • Spiro Compounds