A New Polyether Ladder Compound Produced by the Dinoflagellate Karenia brevis

Andrea J. Bourdelais,*† Henry M. Jacocks,† Jeffrey L. C. Wright,† Paul M. Bigwarfe, Jr.,‡ and Daniel G. Baden†
Wilmington Center for Marine Science, University of North Carolina, 5600 Marvin K. Moss Lane, Wilmington, North Carolina 28409, and Discovery Sciences, aaiPharma Inc., 2320 Scientific Park Drive, Wilmington, North Carolina 28412
J. Nat. Prod., 2005, 68 (1), pp 2–6
DOI: 10.1021/np049797o
Publication Date (Web): November 20, 2004
Copyright © 2005 American Chemical Society and American Society of Pharmacognosy
*

 Author for correspondence. Tel:  (910)-962-2365. Fax:  (910)-962-2410. E-mail:  Bourdelaisa@uncw.edu.

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†

 Wilmington Center for Marine Science.

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‡

 Discovery Sciences, aaiPharma Inc.

Abstract

Abstract Image

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.

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History

  • Published In Issue January 28, 2005
  • Received June 15, 2004

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