Characterization of tamulamides A and B, polyethers isolated from the marine dinoflagellate karenia brevis

Laura T. Truxal, Andrea J. Bourdelais, Henry Jacocks, William M. Abraham, Daniel G. Baden

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Florida red tides occur as the result of blooms of the marine dinoflagellate Karenia brevis. K. brevis is known to produce several families of fused polyether ladder compounds. The most notable compounds are the brevetoxins, potent neurotoxins that activate mammalian sodium channels. Additional fused polyether ladder compounds produced by K. brevis include brevenal, brevisin, and hemibrevetoxin B, all with varying affinities for the same binding site on voltage-sensitive sodium channels. The structure elucidation and biological activity of two additional fused polyether ladder compounds containing seven fused ether rings will be described in this paper. Tamulamide A (MW = 638.30) and tamulamide B (MW = 624.29) were isolated from K. brevis cultures, and their structures elucidated using a combination of NMR spectroscopy and high-resolution mass spectrometry. Tamulamides A and B were both found to compete with tritiated brevetoxin-3 ([3H]-PbTx-3) for its binding site on rat brain synaptosomes. However, unlike the brevetoxins, tamulamides A and B showed no toxicity to fish at doses up to 200 nM and did not cause significant bronchoconstriction in sheep pulmonary assays.

Original languageEnglish
Pages (from-to)536-540
Number of pages5
JournalJournal of Natural Products
Volume73
Issue number4
DOIs
StatePublished - Apr 23 2010
Externally publishedYes

Fingerprint

Dinoflagellida
Polyethers
Ladders
Sodium Channels
Harmful Algal Bloom
Binding Sites
Bronchoconstriction
Synaptosomes
Neurotoxins
Tides
Bioactivity
Ether
Fish
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Toxicity
Rats
Assays
Brain
Mass Spectrometry

ASJC Scopus subject areas

  • Complementary and alternative medicine
  • Molecular Medicine
  • Organic Chemistry
  • Analytical Chemistry
  • Pharmaceutical Science
  • Pharmacology
  • Drug Discovery

Cite this

Characterization of tamulamides A and B, polyethers isolated from the marine dinoflagellate karenia brevis. / Truxal, Laura T.; Bourdelais, Andrea J.; Jacocks, Henry; Abraham, William M.; Baden, Daniel G.

In: Journal of Natural Products, Vol. 73, No. 4, 23.04.2010, p. 536-540.

Research output: Contribution to journalArticle

Truxal, Laura T. ; Bourdelais, Andrea J. ; Jacocks, Henry ; Abraham, William M. ; Baden, Daniel G. / Characterization of tamulamides A and B, polyethers isolated from the marine dinoflagellate karenia brevis. In: Journal of Natural Products. 2010 ; Vol. 73, No. 4. pp. 536-540.
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