The structure of brevetoxin C

Golik, Jerzy; James, John C.; Nakanishi, Koji; Lin, Yong-Yeng

doi:10.1016/s0040-4039(00)87389-x

Cited by 47 publications

(20 citation statements)

References 7 publications

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“…Hemibrevetoxin-B contains structural features similar to brevetoxin but is about half of the size and contains only four fused cyclic ether rings (6,6,7,7). Hemibrevetoxin-B (Figure 2) showed cytotoxicity in mouse neuroblastoma cells at concentrations of 5 μM, but no fish or In this report we describe the isolation, structural characterization, and biological activity of a new ladder-frame polyether aldehyde named brevenal (Figure 3a), isolated from cultures of K. brevis.…”

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

“…The most well-known bioactive compounds isolated from K. brevis are a family of neurotoxins called the brevetoxins (Figure 1), which consist of nine different toxins with two different structural backbones: brevetoxin-A (containing 10 fused cyclic ether rings, 5,8,6,7,9,8,8,6,6,6) 1-3 and brevetoxin-B (containing 11 fused cyclic ether rings, 6,6,6,7,7,6,6,8,6,6,6). [3][4][5][6][7][8] Brevetoxins bind with high affinity to site 5 of voltage sensitive sodium channels (VSSC) in neurons. 9,10 Binding of brevetoxins to tissues containing VSSC results in membrane depolarization, repetitive firing, and increased sodium currents.…”

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confidence: 99%

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A New Polyether Ladder Compound Produced by the Dinoflagellate Karenia b revis

et al. 2004

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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.A number of bioactive polyether compounds have been isolated from the marine dinoflagellate Karenia brevis, the organism responsible for toxic red tides along Florida's Gulf Coast. The most well-known bioactive compounds isolated from K. brevis are a family of neurotoxins called the brevetoxins (Figure 1), which consist of nine different toxins with two different structural backbones: brevetoxin-A (containing 10 fused cyclic ether rings, 5,8,6,7,9,8,8,6,6,6) 1-3 and brevetoxin-B (containing 11 fused cyclic ether rings, 6,6,6,7,7,6,6,8,6,6,6). 3-8Brevetoxins bind with high affinity to site 5 of voltage sensitive sodium channels (VSSC) in neurons. 9,10 Binding of brevetoxins to tissues containing VSSC results in membrane depolarization, repetitive firing, and increased sodium currents. 11-14 Investigation of the effect of brevetoxins on excitable membranes using voltage clamp experiments indicates that brevetoxins activate VSSC by prolonging mean open time, inhibiting channel inactivation, and shifting the channel activation potential to more negative values. 12-14 During K. brevis red tides humans are most commonly affected by brevetoxins that have been aerosolized in sea spray or bioaccumulated in shellfish. Inhaled brevetoxins cause respiratory irritation and breathing difficulties in sensitive populations. 15-17 At sufficiently high concentrations ingested brevetoxins lead to a collection of symptoms commonly referred to as neurotoxic shellfish poisoning (NSP). 18,19 NSP in humans is characterized by sensory abnormalities, cranial nerve dysfunction, gastrointestinal symptoms, and sometimes respiratory failure. 19In 1989 Prasad and Shimizu 20 isolated and described another polyether ladder compound from K. brevis cultures that contained a different structural backbone and named it hemibrevetoxin-B. Hemibrevetoxin-B contains structural features similar to brevetoxin but is about half of the size and contains only four fused cyclic ether rings (6,6,7,7). Hemibrevetoxin-B (Figure 2) showed cytotoxicity in mouse neuroblastoma cells at concentrations of 5 μM, but no fish or In this report we describe the isolation, structural characterization, and biological activity of a new ladder-frame polyether aldehyde named brevenal (Figure 3a), isolated from cultures of K. brevis. Brevenal as well as its dimethyl acetal derivative ( Figure 3b) contain five fused cyclic ether rings, have low toxicity to fish, and have a structural backbone different from both brevetoxins and hemibre...

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Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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A New Polyether Ladder Compound Produced by the Dinoflagellate Karenia b revis

et al. 2004

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“…Dinophysistoxin 1 (DTX1) has methyl groups at both positions. Figure if shows a typical brevetoxin (PbTx2) molecule [20,21 ], with a polyether, ladder-like structure [22], and Figure 1 g shows gymnodimine [3], an exotic toxin, found exclusively in the South Pacific [23 25].…”

Section: Introductionmentioning

confidence: 99%

Simultaneous analysis of different algal toxins by LC-MS

et al. 2002

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Key WordsColumn liquid chromatography-mass spectrometry Diarrhetic shellfish poisoning Amnesic shellfish poisoning Brevetoxins and pectenotoxins Spirohdes and gymnodimine SummaryA method is proposed for the simultaneous determination of amnesic shellfish poisoning (ASP) toxin, diarrhetic shellfish poisoning (DSP) toxins, spirohdes, azaspiracids (AZP), pectenotoxins (PTX), brevetoxins (PbTx), and gymnodimine. After extraction of all these toxins with one solvent only the crude extract is subjected directly to reversed-phase LC-MS with atmospheric-pressure ionization.The method was applied to bulk plankton samples obtained during a research cruise off the east coast of Scotland in May 2000. Contamination of plankton samples from one spot with different toxins from a va riel",/of g rou ps was determined.

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“…(Shimizu, 1978). Recent investigations of the N(4) secondary metabolites of this microorganism have N(5) C(6) resulted in the identification of a number of cyclic c(7) polyethers and phosphorus compounds (Lin,Rish,c(8) Ray, van Engen, Clardy, Golik, James & Naskanishi, c(9) c(10) 1981; Golik, James & Nakanishi, 1982;Chou & c(11) Shimizu, 1982;Alam, Sanduja, Hossain & van der c(12) C(13) Helm, 1982;Dinovi, Trainor, Nakanishi, Sanduja & N(14) Alam, 1983). In this communication we report the N(15) isolation and X-ray structure of 6-azidotetrazolo [5,1-N(16) …”

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confidence: 99%