A new polyether ladder compound produced by the dinoflagellate Karenia brevis

J Nat Prod. 2005 Jan;68(1):2-6. doi: 10.1021/np049797o.

Abstract

A new ladder-frame polyether compound containing five fused ether rings was isolated from laboratory cultures of the marine dinoflagellate Karenia brevis. This compound, named brevenal, and its dimethyl acetal derivative both competitively displace brevetoxin from its binding site in rat brain synaptosomes. Significantly, these compounds are also nontoxic to fish and antagonize the toxic effects of brevetoxins in fish. The structure and biological activity of brevenal, as well as the dimethyl acetal derivative, are described in this paper.

Publication types

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

MeSH terms

  • Animals
  • Binding, Competitive / drug effects*
  • Brain / drug effects
  • Dinoflagellida / chemistry*
  • Ethers / chemistry
  • Ethers / isolation & purification*
  • Ethers / pharmacology
  • Fishes / metabolism
  • Male
  • Marine Toxins / chemistry
  • Marine Toxins / pharmacology*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxocins / chemistry
  • Oxocins / pharmacology*
  • Polymers / chemistry
  • Polymers / isolation & purification*
  • Polymers / pharmacology
  • Rats
  • Rats, Sprague-Dawley

Substances

  • Ethers
  • Marine Toxins
  • Oxocins
  • Polymers
  • brevenal (polyether)
  • brevetoxin