Brevisamide: an unprecedented monocyclic ether alkaloid from the dinoflagellate Karenia brevis that provides a potential model for ladder-frame initiation

Org Lett. 2008 Aug 21;10(16):3465-8. doi: 10.1021/ol801243n. Epub 2008 Jul 23.

Abstract

The dinoflagellate Karenia brevis is known for the production of brevetoxins, a family of polycyclic ether toxins, as well as their antagonist brevenal. Further examination of organic extracts of K. brevis has uncovered yet another unprecedented cyclic ether alkaloid named brevisamide. This report describes the structure elucidation of brevisamide based on detailed MS and NMR spectral analysis, and the importance of this new compound in shedding light on the biogenesis of fused polyethers is discussed.

Publication types

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

MeSH terms

  • Alkaloids / chemistry*
  • Animals
  • Dinoflagellida / chemistry*
  • Ethers / chemistry*
  • Fatty Acids, Unsaturated / chemistry*
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Mass Spectrometry / methods
  • Molecular Conformation
  • Pyrans
  • Reference Standards
  • Thiopental / analogs & derivatives
  • Thiopental / chemistry

Substances

  • Alkaloids
  • Ethers
  • Fatty Acids, Unsaturated
  • Pyrans
  • brevisamide
  • thiobutabarbital
  • Thiopental