Brocaenols A-C: novel polyketides from a marine derived Penicillium brocae

J Org Chem. 2003 Mar 7;68(5):2014-7. doi: 10.1021/jo020597w.

Abstract

Chemical investigation of a Penicillium brocae, obtained from a tissue sample of a Fijian Zyzyya sp. sponge, yielded two known diketopiperazines and three novel cytotoxic polyketides, brocaenols A-C. The brocaenols contain an unusual enolized oxepine lactone ring system that to the best of our knowledge is unprecedented in the literature. The structures were elucidated by using 2D-NMR methods including an INADEQUATE experiment. The absolute stereochemistry of brocaenol A was established by using a modified Mosher method. The taxonomy of the producing fungus was elucidated by using both morphological and rDNA sequence analysis.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Fermentation
  • Fiji
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Heterocyclic Compounds, 3-Ring / isolation & purification*
  • Inhibitory Concentration 50
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Penicillium / chemistry*
  • Porifera / chemistry*
  • Stereoisomerism

Substances

  • Heterocyclic Compounds, 3-Ring
  • brocaenol A
  • brocaenol B
  • brocaenol C