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Domoic acid (DA) is a kainic acid analog neurotoxin that causes amnesic shellfish poisoning (ASP).^[1] It is produced by algae and accumulates in shellfish, sardines, and anchovies. When sea lions, otters, cetaceans, humans etc., then eat contaminated animals poisoning may result. Exposure to the biotoxin affects the brain, causing seizures, and possibly death.^[2]

History

There has been little use of domoic acid throughout history except for in Japan, where it has been used as an anthelmintic for centuries. Domoic acid was first isolated in 1959 from a species of red algae, Chondria armata, in Japan; commonly referred to as “doumoi” or “hanyanagi”. Poisonings in history have been rare, or undocumented; however, it is thought that the increase in human activates is resulting in an increasing frequency of toxic algal blooms along coastlines in recent years. Consequently, poisonings have been affecting sea animal, birds, and humans.^[3]

It has been speculated that the story in Exodus, from the Bible, of Moses turning the Nile into blood, may have been attributed to a red algal bloom that produced domoic acid. ^[4]

In 1961, seabirds attacked the Santa Cruz and Capitola areas in California, and though it was never confirmed, they were thought to be under the influence of domoic acid.^[5]

In 1987, on Prince Edward Island, Canada, there was a shellfish poisoning resulting in 3 deaths. Blue mussels (Mytulis edulis) contaminated with domoic acid were blamed.^[6]

An incident in which domoic acid may have been involved took place on June 22, 2006, when a California brown pelican flew through the windshield of a car on the Pacific Coast Highway.^[7]

Chemistry

Synthesis of Domoic Acid as described by Jonathan Clayden, Benjamin Read and Katherine R. Hebditch, in their article Chemistry of domoic acid, isodomoic acids, and their analogues^[8]

General

Domoic acid is a structural analog of kainic acid and proline. Ohfune and Tomita, who wanted to investigate its absolute stereochemistry, were the first and only to synthesize domoic acid in 1982. ^[9]

Biosynthesis

In 1999, using ¹³C- and ¹⁴C-labelled precursors, the biosynthesis of domoic acid in the diatom Pseudo-nitzschia was examined. After addition of [1,2-13C2]-acetate, NMR spectroscopy showed enrichment of every carbon in domoic acid. This enrichment was consistent with two biosynthetic pathways. The labeling pattern determined that domoic acid can be biosynthesized by an isoprenoid intermediate in combination with a tricarboxylic acid (TCA) cycle intermediate.^[10]

Synthesis

Using intermediates 5 and 6, a Diels-Alder reaction produced a bicyclic compound (7). 7 then underwent ozonolysis to open the six-membered ring leading to selenide (8). 8 was then deselenated to form 9 (E-9 and Z-9), lastly leading to the formation of (-) domoic acid. ^[11]

Mechanism of Action

The effects of domoic acid have been attributed to several mechanisms, but the one of concern is through glutamate receptors. Domoic acid is an excitatory amino acid analogue of glutamate; a neurotransmitter in the brain that activates glutamate receptors. Domoic acid has a very strong affinity for these receptors, which results in excitotoxicity initiated by an integrative action on ionotropic glutamate receptors at both sides of the synapse blocking the channel from rapid desensitization. In addition there is a synergistic effect with endogenous glutamate and N-Methyl-D-aspartate receptor agonists that contribute to the excitotoxicity.

In the brain, domoic acid especially damages the hippocampus and amygdaloid nucleus. It damages the neurons by activating AMPA and kainate receptors, causing an influx of calcium. Although calcium flowing into cells is normal, the uncontrolled increase of calcium causes the cells to degenerate. Because the hippocampus may be severely damaged, short-term memory loss occurs. It may also cause kidney damage – even at levels considered safe for human consumption, a new study in mice has revealed. The kidney is affected at a hundred times lower than the concentration allowed under FDA regulations.^[12]^[13]

Symptoms

Humans	Animals
vomiting	head weaving
nausea	seizures
diarrhea and abdominal cramps within 24 hours of ingestion	bulging eyes
headache	mucus from the mouth
dizziness	disorientation
confusion, disorientation
loss of short-term memory
motor weakness
seizures
profuse respiratory secretions
cardiac arrhythmias
coma and possible death

^[14]

Toxicology

Domoic acid producing algal blooms are associated with the phenomenon of amnesic shellfish poisoning (ASP). Domoic acid can bioaccumulate in marine organisms such as shellfish, anchovies, and sardines that feed on the phytoplankton known to produce this toxin. It can accumulate in high concentrations in the tissues of these plankton feeders when the toxic phytoplankton are high in concentration in the surrounding waters. Domoic acid is a neurotoxin that inhibits neurochemical processes, causing short-term memory loss, brain damage, and, in severe cases, death in humans. In marine mammals, domoic acid typically causes seizures and tremors.

Studies have shown that there are no symptomatic effects in humans at levels of 0.5mg/kg of body weight. In the 1987 domoic acid poisoning on Prince Edward Island concentrations ranging from 0.31-1.28mg/g of muscle tissue were noted in people that became ill (three of which died).Dangerous levels of domoic acid have been calculated based on cases such as the one on Prince Edward island, however the exact LD50 for humans is unknown; for mice the LD50 is 3.6mg/kg.^[15]

New research has found that domoic acid is heat resistant and very stable toxin, which can damage kidneys at concentrations that are 100 times lower than what causes neurological effects.^[16]

Diagnosis and Prevention

In order to be diagnosed and treated if poisoned, domoic acid must first be detected. Methods such as ELISA (enzyme-linked immunosorbent assay), or probe development with PCR (polymerase chain reaction) may be used.^[17]

There is no known antidote available for domoic acid therefore if poisoning occurs, it is advised to go quickly to a hospital. It is important to note that cooking or freezing affected fish or shellfish tissue that are contaminated with domoic acid does not lessen the toxicity.^[18]

As a public health concern, the concentration of domoic acid in shellfish and shellfish parts at point of sale should not exceed the current permissible limit of 20mg/g tissue. In addition during processing shellfish, it is important to pay attention to environmental condition factors.^[19]

Pop Culture

On August 18, 1961, in Capitola and Santa Cruz, California there was an invasion of what people described as chaotic seabirds. These birds were believed to be under the influence of domoic acid, and it inspired a scene in Alfred Hitchcock’s feature film The Birds (1963).^[20]

In addition domoic acid was used to poison a witness in the TV series Elementary, episode The Red Team.

References

^ Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.
^ "Domoic Acid Toxicity". The Marine Mammal Center. Retrieved 2 April 2015.
^ "Domoic Acid Poisoning". Northwest Fisheries science center. Retrieved 17 April 2015.
^ Baier, Charles. "http://www.webpages.uidaho.edu/etox/resources/case_studies/REDTIDE2.PDF" (PDF). Retrieved 15 April 2015.
^ "DOMOIC ACID - A major concern to washington state’s shellfish lovers". Washington Department of Fish and wildlife. Retrieved 12 April 2015.
^ Gilbert, Steven. "Domoic Acid". Toxipedia. Retrieved 15 April 2015.
^ "Possibly drunk pelican hits windshield". NBC news. Retrieved 12 April 2015.
^ Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.
^ Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.
^ Ramsey; Douglas; Walter; Wright (1999). "Biosynthesis of domoic acid by the diatom Pseudo-nitzschia multiseries.". Wiley 6. Retrieved 2 April 2015.
^ Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.
^ Pulido, Olga (2008). "Domoic Acid Toxicologic Pathology: A Review". Mar Drugs.
^ Smith, Torrey. "Toxin in seafood causes kidney damage in mice at levels considered safe for consumption". avante medical center.
^ Gilbert, Steven. "Domoic Acid". Toxipedia. Retrieved 2 April 2015.
^ Gilbert, Steven. "Domoic Acid". Toxipedia.
^ Smith, Torrey. "Toxin in seafood causes kidney damage in mice at levels considered safe for consumption". avante medical center.
^ "Detection and Analysis of Marine Biotoxins". Northwest fisheries science center.
^ "DOMOIC ACID - A major concern to washington state’s shellfish lovers". washington department of fish and wildlife.
^ Kumar, KP; Kumar, SP; Nair, GA (May 2009). "Risk assessment of the amnesic shellfish poison, domoic acid, on animals and humans.". Environmental Biology.
^ Bargu, Sibel; Silver, Mary; Ohman, Mark; Benitez, Claudia; Garrison, David (2011). "Mystery behind Hitchcock's birds". Nature Geoscience.

External links

"Domoic Acid and Pseudo-nitzschia References". Fisheries and Oceans Canada.
"Amnesic Shellfish Poisoning, Domoic Acid, and Pseudo-nitzschia". International Society for the Study of Harmful Algae ISSHA.
"Domoic acid". IPCS INCHEM.
"Domoic Acid - A Major Concern to Washington State’s Shellfish Lovers". Washington Department of Fish and Wildlife.
"Domoic Acid Toxicity".

English Journal

Neonatal domoic acid treatment produces alterations to prepulse inhibition and latent inhibition in adult rats.

Marriott AL, Ryan CL, Doucette TA.SourceDepartment of Biology, University of Prince Edward Island, 550 University Avenue, PE, Canada, C1A 4P3.
Pharmacology, biochemistry, and behavior.Pharmacol Biochem Behav.2012 Dec;103(2):338-44. doi: 10.1016/j.pbb.2012.08.022. Epub 2012 Sep 7.
Schizophrenia is a complex and severe mental disorder characterized by positive, negative and cognitive symptoms. Characteristic behavioral alterations reflecting these categories of symptoms have been observed in many animal models of this disorder, and are consistent with those manifested in the c
PMID 22981693

Algal toxins and reverse osmosis desalination operations: Laboratory bench testing and field monitoring of domoic acid, saxitoxin, brevetoxin and okadaic acid.

Seubert EL, Trussell S, Eagleton J, Schnetzer A, Cetinić I, Lauri P, Jones BH, Caron DA.SourceDepartment of Biological Sciences, University of Southern California, 3616 Trousdale Parkway, AHF 301, Los Angeles, CA 90089-0371, USA. Electronic address: seubert@usc.edu.
Water research.Water Res.2012 Dec 1;46(19):6563-73. doi: 10.1016/j.watres.2012.09.042. Epub 2012 Oct 4.
The occurrence and intensity of harmful algal blooms (HABs) have been increasing globally during the past few decades. The impact of these events on seawater desalination facilities has become an important topic in recent years due to enhanced societal interest and reliance on this technology for au
PMID 23079130

Japanese Journal

A Review of Glutamate Receptors II : Pathophysiology and Pathology

Rousseaux Colin G.
Journal of toxicologic pathology 21(3), 133-173, 2008-09-30
… However, a Ka analog, domoate, is sometimes ingested accidentally in blue mussels; …
NAID 10027893783

Effects of Topiramate on Kainate-and Domoate-Activated [^14C] Guanidinium Ion Flux Through GluR6 Channels in Transfected BHK Cells Using Cytostar-T Scintillating Microplates

SMITH L.,PRICE-JONES M.,HUGHES K.,EGEBJERG J.,POULSEN F.,WIBERG F. C.,SHANK R. P.
Supplement to Epilepsia 41(1), S48-S51, 2000-01-01
NAID 10009601771

ハナヤナギの成分研究(第8報) : Domoic Acidの構造論その1

竹本常松 [他],醍醐皓二,近藤嘉和,近藤一恵
藥學雜誌 86(10), 874-877, 1966-10-25
… The NMR spectrum of trimethyl domoate (in CDCl_3) shows a doublet methyl (J=7.0 c.p.s.) at 1.29 p.p.m., a methyl signal which indicates an allylic coupling at 1.79 p.p.m., and an olefinic proton signal corresponding to 3H at 5.5〜6.6 p.p.m. From its first-order analysis, the configuration of the 1,3-hexadienyl side chain was determined as trans : trans : S-trans. … The infrared spectra of both domoic acid and trimethyl domoate show absorption due to the trans-double bond. …
NAID 110003653083

Related Pictures

★リンクテーブル★

リンク元	「ドーモイ酸」「domoic acid」

「ドーモイ酸」

Domoic acid
Identifiers
CAS Registry Number	14277-97-5
ChEBI	CHEBI:34727
ChEMBL	ChEMBL420720
ChemSpider	4445428
	InChI InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4-/t9-,10+,11-,13+/m1/s1 ; Key: VZFRNCSOCOPNDB-AOKDLOFSSA-N ; InChI=1/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4-/t9-,10+,11-,13+/m1/s1; Key: VZFRNCSOCOPNDB-AOKDLOFSBM ;
Jmol-3D images	Image
PubChem	5282253
	SMILES O=C(O)[C@H]1NC[C@H](/C(=C\C=C\[C@H](C(=O)O)C)C)[C@@H]1CC(=O)O ;
Properties
Chemical formula	C15H21NO6
Molar mass	311.3303 g/mol
Density	1.273 g/cm3
Boiling point	607.2 degrees Celsius at 760 mmHg (101.3 kPa)
Vapor pressure	2.62×10−16 mmHg (34.9 fPa) at 25 °C
Hazards
R-phrases	R20 R21 R22
S-phrases	S36 S37
Flash point	321 °C (610 °F; 594 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

　　[★]

英: domoate, domoic acid
関: カイニン酸受容体刺激薬、カイニン酸

カイニン酸受容体刺激薬

「domoic acid」

　　[★] ドーモイ酸, domoate

[1] Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.

[2] "Domoic Acid Toxicity". The Marine Mammal Center. Retrieved 2 April 2015.

[3] "Domoic Acid Poisoning". Northwest Fisheries science center. Retrieved 17 April 2015.

[4] Baier, Charles. "http://www.webpages.uidaho.edu/etox/resources/case_studies/REDTIDE2.PDF" (PDF). Retrieved 15 April 2015.

[5] "DOMOIC ACID - A major concern to washington state’s shellfish lovers". Washington Department of Fish and wildlife. Retrieved 12 April 2015.

[6] Gilbert, Steven. "Domoic Acid". Toxipedia. Retrieved 15 April 2015.

[7] "Possibly drunk pelican hits windshield". NBC news. Retrieved 12 April 2015.

[8] Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.

[9] Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.

[10] Ramsey; Douglas; Walter; Wright (1999). "Biosynthesis of domoic acid by the diatom Pseudo-nitzschia multiseries.". Wiley 6. Retrieved 2 April 2015.

[11] Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.

[12] Pulido, Olga (2008). "Domoic Acid Toxicologic Pathology: A Review". Mar Drugs.

[13] Smith, Torrey. "Toxin in seafood causes kidney damage in mice at levels considered safe for consumption". avante medical center.

[14] Gilbert, Steven. "Domoic Acid". Toxipedia. Retrieved 2 April 2015.

[15] Gilbert, Steven. "Domoic Acid". Toxipedia.

[16] Smith, Torrey. "Toxin in seafood causes kidney damage in mice at levels considered safe for consumption". avante medical center.

[17] "Detection and Analysis of Marine Biotoxins". Northwest fisheries science center.

[18] "DOMOIC ACID - A major concern to washington state’s shellfish lovers". washington department of fish and wildlife.

[19] Kumar, KP; Kumar, SP; Nair, GA (May 2009). "Risk assessment of the amnesic shellfish poison, domoic acid, on animals and humans.". Environmental Biology.

[20] Bargu, Sibel; Silver, Mary; Ohman, Mark; Benitez, Claudia; Garrison, David (2011). "Mystery behind Hitchcock's birds". Nature Geoscience.

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domoate