Noreupenifeldin, a Tropolone From an Unidentified Ascomycete

J Nat Prod. 2008 Mar;71(3):457-9. doi: 10.1021/np070513k. Epub 2007 Dec 21.

Abstract

Noreupenifeldin ( 2), a new monotropolone derivative of the bistropolone eupenifeldin ( 1), was isolated from an unidentified ascomycete by bioassay-guided fractionation as part of our search for new anthelmintics. The structure of 1 was confirmed by comparison with literature data. The structure of 2 was elucidated from MS and 1D and 2D NMR data. Compounds 1 and 2 are diastereomers of pycnidione ( 3) and epolone A ( 4), respectively. Compounds 1- 3 were evaluated for their anthelmintic activity against the parasitic worm Hemonchus contortus. Compounds 1 and 3 exhibited modest in vitro activity, showing EC 90 50 and 83 microg/mL, respectively, in reducing motility of L3 larvae of H. contortus. Compound 2 was inactive, indicating that the second tropolone moiety is required for activity.

MeSH terms

  • Animals
  • Ascomycota / chemistry*
  • Haemonchus / drug effects
  • Molecular Structure
  • Tropolone / analogs & derivatives*
  • Tropolone / chemistry
  • Tropolone / isolation & purification*
  • Tropolone / pharmacology

Substances

  • noreupenifeldin
  • Tropolone