A new polyether ladder compound produced by the dinoflagellate Karenia brevis.
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.
Bourdelais
Andrea J
AJ
Wilmington Center for Marine Science, University of North Carolina, 5600 Marvin K. Moss Lane, Wilmington, North Carolina 28409, USA. Bourdelaisa@uncw.edu
Jacocks
Henry M
HM
Wright
Jeffrey L C
JL
Bigwarfe
Paul M
PM
Baden
Daniel G
DG
D000818:Animals; D001667:Binding, Competitive / Q000187:drug effects*; D001921:Brain / Q000187:drug effects; D004141:Dinoflagellida / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005399:Fishes / Q000378:metabolism; D008297:Male; D008387:Marine Toxins / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D035964:Oxocins / Q000737:chemistry / Q000494:pharmacology*; D011108:Polymers / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D051381:Rats; D017207:Rats, Sprague-Dawley; D000095702:Polyether Toxins
D004987:Ethers; D008387:Marine Toxins; D035964:Oxocins; D011108:Polymers; C489035:brevenal (polyether); C053342:brevetoxin; D000095702:Polyether Toxins