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Brevetoxin (PbTx), or brevetoxins, are a suite of cyclic polyether compounds produced naturally by a species of dinoflagellate known as Karenia brevis. Brevetoxins are neurotoxins that bind to voltage-gated sodium channels in nerve cells, leading to disruption of normal neurological processes and causing the illness clinically described as neurotoxic shellfish poisoning (NSP).[1]
Although brevetoxins are most well-studied in K. brevis, they are also found in other species of Karenia and at least one large fish kill has been traced to brevetoxins in Chattonella.[1]
Brevetoxin A[2]
Brevetoxin B[3]
chemical structure
Brevetoxin A
Brevetoxin B
subtypes
Brevetoxin-1 (PbTx-1) R = -CH2C(=CH2)CHO
Brevetoxin-7 (PbTx-7) R = -CH2C(=CH2)CH2OH
Brevetoxin-10 (PbTx-10) R = -CH2CH(-CH3)CH2OH
Brevetoxin-2 (PbTx-2) R = -CH2C(=CH2)CHO
Brevetoxin-3 (PbTx-3) R = -CH2C(=CH2)CH2OH
Brevetoxin-8 (PbTx-8) R = -CH2COCH2Cl
Brevetoxin-9 (PbTx-9) R = -CH2CH(CH3)CH2OH
Other Brevetoxins:
Brevetoxin-5 (PbTx-5): like PbTx-2, but acetylated hydroxyl group in position 38.
Brevetoxin-6 (PbTx-6): like PbTx-2, but double bond 27-28 is epoxidated.
Brevetoxin-B was synthesized in 1995 by K. C. Nicolaou and coworkers in 123 steps with 91% average yield (final yield ~9·10−6)[4] and in 2004 in a total of 90 steps with an average 93% yield for each step (0.14% overall).[3]
K. C. Nicolaou and coworkers reported their synthesis of Brevetoxin-1 in 1998.[5] In 2009, Michael Crimmins and co-workers reported their synthesis of Brevetoxin-1 as well.[6]
^ abWatkins SM, Reich A, Fleming LE, Hammond R (2008). "Neurotoxic Shellfish Poisoning". Marine Drugs. 6 (3): 431–455. doi:10.3390/md20080021. PMC 2579735. PMID 19005578.
^Nicolaou KC, Yang Z, Shi G, Gunzner JL, Agrios KA, Gärtner P (1998). "Total Synthesis of Brevetoxin A". Nature. 392 (6673): 264–269. Bibcode:1998Natur.392..264N. doi:10.1038/32623. PMID 9521320. S2CID 373710.
^ abMatsuo G, Kawamura K, Hori N, Matsukura H, Nakata T (2004). "Total Synthesis of Brevetoxin-B". Journal of the American Chemical Society. 126 (44): 14374–14376. doi:10.1021/ja0449269. PMID 15521755.
^Nicolaou KC, Rutjes FP, Theodorakis EA, Tiebes J, Sato M, Untersteller E (1995). "Total Synthesis of Brevetoxin B. 3. Final Strategy and Completion". Journal of the American Chemical Society. 117 (41): 10252–10263. doi:10.1021/ja00146a010. hdl:2066/26297.
^Nicolaou KC, Yang Z, Shi GQ, Gunzner JL, Agrios KA, Gärtner P (1998). "Total Synthesis of Brevetoxin A". Nature. 392 (6673): 264–269. Bibcode:1998Natur.392..264N. doi:10.1038/32623. PMID 9521320. S2CID 373710.
Brevetoxin (PbTx), or brevetoxins, are a suite of cyclic polyether compounds produced naturally by a species of dinoflagellate known as Karenia brevis...
Satake M, Murata K, Naoki H, Kaspar HF, Yasumoto T (1995). "Brevetoxin B3, a new brevetoxin nalog isolated from the greenshell mussel perna canaliculus...
shellfish, breathing in aerosolized brevetoxins (i.e. PbTx or Ptychodiscus toxins) and in some cases skin contact. The brevetoxins bind to voltage-gated sodium...
are cyclic polyethers. Some toxins produced by dinoflagellates such as brevetoxin and ciguatoxin are extremely large and are known as cyclic or ladder polyethers...
treated with Brevetoxin B (PbTx2), there was a noticeable 2-3 fold growth in the amount of DNA seen in comet tails which tell us that Brevetoxin B shows in...
complex, highly symmetric, man-made polycyclic compound (non-aromatic). Brevetoxin A, a natural product with ten rings, all fused, and all heterocyclic,...
Neurotoxic shellfish poisoning (NSP) is caused by the consumption of brevetoxins, which are marine toxins produced by the dinoflagellate Karenia brevis...
Brevetoxin A, a natural product with ten rings, all fused, and all heterocyclic, and a toxic component associated with the organisms responsible for red...
also affects barracuda, snapper, hogfish, king mackerel, and sea bass. Brevetoxin Domoic acid Okadaic acid Saxitoxin Tetrodotoxin Swift AE, Swift TR (2008)...
naturally produces a suite of potent neurotoxins collectively called brevetoxins, which cause gastrointestinal and neurological problems in other organisms...
pathogens. Exposure to brevetoxin during a red tide event is also a source of mortality; manatees may be exposed to brevetoxin after a red tide has subsided...
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List of aquarium diseases Related topics Amnesic shellfish poisoning Brevetoxin Ciguatera Diarrheal shellfish poisoning Fish kill Marine viruses Neurotoxic...
List of aquarium diseases Related topics Amnesic shellfish poisoning Brevetoxin Ciguatera Diarrheal shellfish poisoning Fish kill Marine viruses Neurotoxic...
List of aquarium diseases Related topics Amnesic shellfish poisoning Brevetoxin Ciguatera Diarrheal shellfish poisoning Fish kill Marine viruses Neurotoxic...
List of aquarium diseases Related topics Amnesic shellfish poisoning Brevetoxin Ciguatera Diarrheal shellfish poisoning Fish kill Marine viruses Neurotoxic...
List of aquarium diseases Related topics Amnesic shellfish poisoning Brevetoxin Ciguatera Diarrheal shellfish poisoning Fish kill Marine viruses Neurotoxic...
North Korean medical injection derived from tetrodotoxin 4-Aminopyridine Brevetoxin Ciguatoxin Conotoxin Domoic acid Neosaxitoxin Neurotoxin Okadaic acid...
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List of aquarium diseases Related topics Amnesic shellfish poisoning Brevetoxin Ciguatera Diarrheal shellfish poisoning Fish kill Marine viruses Neurotoxic...
List of aquarium diseases Related topics Amnesic shellfish poisoning Brevetoxin Ciguatera Diarrheal shellfish poisoning Fish kill Marine viruses Neurotoxic...
microscopic marine algae Karenia brevis. This dinoflagellate produces brevetoxins that can have toxic effects on the central nervous system of animals...
List of aquarium diseases Related topics Amnesic shellfish poisoning Brevetoxin Ciguatera Diarrheal shellfish poisoning Fish kill Marine viruses Neurotoxic...
life Paralytic shellfish poisoning – Syndrome of shellfish poisoning Brevetoxin – Class of chemical compounds produced naturally Ciguatoxin – Group of...
dolphins consuming these toxic fish from the brevetoxin produced by the dinoflagellate Karenia brevis. Brevetoxins are neurotoxins that can cause acute respiratory...
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