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Literature DB >> 15679307

A new polyether ladder compound produced by the dinoflagellate Karenia brevis.

Andrea J Bourdelais¹, Henry M Jacocks, Jeffrey L C Wright, Paul M Bigwarfe, Daniel G Baden.

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.

Entities: Chemical Species

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Year: 2005 PMID： 15679307 PMCID： PMC2659471 DOI： 10.1021/np049797o

Source DB: PubMed Journal: J Nat Prod ISSN： 0163-3864 Impact factor: 4.050

11 in total

Review 1. Cellular and molecular biology of voltage-gated sodium channels.

Authors: W A Catterall
Journal: Physiol Rev Date: 1992-10 Impact factor: 37.312

2. The sodium channel activator Brevetoxin-3 uncovers a multiplicity of different open states of the cardiac sodium channel.

Authors: W Schreibmayer; G Jeglitsch
Journal: Biochim Biophys Acta Date: 1992-03-02

Review 3. Brevetoxins: unique polyether dinoflagellate toxins.

Authors: D G Baden
Journal: FASEB J Date: 1989-05 Impact factor: 5.191

4. Brevetoxins, unique activators of voltage-sensitive sodium channels, bind to specific sites in rat brain synaptosomes.

Authors: M A Poli; T J Mende; D G Baden
Journal: Mol Pharmacol Date: 1986-08 Impact factor: 4.436

5. Brevetoxin-3 (PbTx-3) and its derivatives modulate single tetrodotoxin-sensitive sodium channels in rat sensory neurons.

Authors: G Jeglitsch; K Rein; D G Baden; D J Adams
Journal: J Pharmacol Exp Ther Date: 1998-02 Impact factor: 4.030

6. Neurotoxic shellfish poisoning and brevetoxin metabolites: a case study from Florida.

Authors: M A Poli; S M Musser; R W Dickey; P P Eilers; S Hall
Journal: Toxicon Date: 2000-07 Impact factor: 3.033

7. Structure of brevetoxin A (GB-1 toxin), the most potent toxin in the Florida red tide organism Gymnodinium breve (Ptychodiscus brevis).

Authors: Y Shimizu; H N Chou; H Bando; G Van Duyne; J Clardy
Journal: J Am Chem Soc Date: 1986-02-01 Impact factor: 15.419

8. Literature Review of Florida Red Tide: Implications for Human Health Effects.

Authors: Barbara Kirkpatrick; Lora E Fleming; Dominick Squicciarini; Lorrie C Backer; Richard Clark; William Abraham; Janet Benson; Yung Sung Cheng; David Johnson; Richard Pierce; Julia Zaias; Gregory D Bossart; Daniel G Baden
Journal: Harmful Algae Date: 2004-04-01 Impact factor: 4.273

9. Brevenal is a natural inhibitor of brevetoxin action in sodium channel receptor binding assays.

Authors: Andrea J Bourdelais; Susan Campbell; Henry Jacocks; Jerome Naar; Jeffery L C Wright; Jigani Carsi; Daniel G Baden
Journal: Cell Mol Neurobiol Date: 2004-08 Impact factor: 5.046

10. Inhibition of brevetoxin binding to the voltage-gated sodium channel by gambierol and gambieric acid-A.

Authors: Masayuki Inoue; Masahiro Hirama; Masayuki Satake; Kiminori Sugiyama; Takeshi Yasumoto
Journal: Toxicon Date: 2003-03 Impact factor: 3.033

40 in total

Review 1. The biosynthesis of polyketide metabolites by dinoflagellates.

Authors: Kathleen S Rein; Richard V Snyder
Journal: Adv Appl Microbiol Date: 2006 Impact factor: 5.086

2. Characterization and localization of a hybrid non-ribosomal peptide synthetase and polyketide synthase gene from the toxic dinoflagellate Karenia brevis.

Authors: Susanna López-Legentil; Bongkeun Song; Michael DeTure; Daniel G Baden
Journal: Mar Biotechnol (NY) Date: 2009-05-27 Impact factor: 3.619

A new polyether ladder compound produced by the dinoflagellate Karenia brevis.

Review 1. Cellular and molecular biology of voltage-gated sodium channels.

2. The sodium channel activator Brevetoxin-3 uncovers a multiplicity of different open states of the cardiac sodium channel.

Review 3. Brevetoxins: unique polyether dinoflagellate toxins.

4. Brevetoxins, unique activators of voltage-sensitive sodium channels, bind to specific sites in rat brain synaptosomes.

5. Brevetoxin-3 (PbTx-3) and its derivatives modulate single tetrodotoxin-sensitive sodium channels in rat sensory neurons.

6. Neurotoxic shellfish poisoning and brevetoxin metabolites: a case study from Florida.

7. Structure of brevetoxin A (GB-1 toxin), the most potent toxin in the Florida red tide organism Gymnodinium breve (Ptychodiscus brevis).

8. Literature Review of Florida Red Tide: Implications for Human Health Effects.

9. Brevenal is a natural inhibitor of brevetoxin action in sodium channel receptor binding assays.

10. Inhibition of brevetoxin binding to the voltage-gated sodium channel by gambierol and gambieric acid-A.

Review 1. The biosynthesis of polyketide metabolites by dinoflagellates.

2. Characterization and localization of a hybrid non-ribosomal peptide synthetase and polyketide synthase gene from the toxic dinoflagellate Karenia brevis.

3. Homing in on an alga's threat-and therapeutic promise.

4. Total synthesis, structure revision, and absolute configuration of (-)-brevenal.

Review 5. The continuing saga of the marine polyether biotoxins.

Review 6. Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

7. Osmotic stress triggers toxin production by the dinoflagellate Karenia brevis.

8. A highly convergent approach toward (-)-brevenal.

9. A Formal Total Synthesis of (-)-Brevisamide.

Review 10. Recent synthetic studies leading to structural revisions of marine natural products.