Domoic acid

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Domoic acid
Domoinic Acid Structural Formulae.png
Identifiers
CAS number 14277-97-5 N
PubChem 5282253
ChemSpider 4445428 YesY
ChEBI CHEBI:34727 N
ChEMBL CHEMBL420720 N
Jmol-3D images Image 1
Properties
Molecular 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 noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Domoic acid (DA), the neurotoxin that causes amnesic shellfish poisoning (ASP), is a kainic acid analog, heterocyclic amino acid associated with certain harmful algal blooms.[1]

Occurrence[edit]

In 1958, domoic acid was originally isolated from the red alga called "doumoi" or "hanayanagi" (Chondria armata[2]) in Japan. "Doumoi" is used as an anthelmintic in Tokunoshima, Kagoshima.[3] Domoic acid is also produced by some diatoms of the genus Pseudo-nitzschia[1] and by some strains of the diatom species Nitzschia navis-varingica.[1][4]

Pseudo-nitzschia multiseries loses most of its ability to produce domoic acid when it is cultured axenically. However, domoic acid production recovers when bacteria from the original culture are reintroduced to axenic cultures, indicating a bacterial association with domoic acid production in this species.[5] Other factors that affect the biosynthesis of domoic acid are reviewed by Bates and Trainer (2006),[6] Trainer et al. (2008),[7] Lelong et al. (2012)[8] and Trainer et al. (2012).[9]

The increasing frequency and geographic extent of toxic algal blooms along populated coastlines is generally attributed to human activities.[10]

Chemistry[edit]

Domoic acid is a structural analog of kainic acid and proline. General aspects of domoic acid chemistry, including its isomers and degradation, are reviewed by Lelong et al. (2012).[8]

Toxicology[edit]

Considerable recent research has been carried out by the Marine Mammal Center and other scientific centers on the association of domoic acid-producing harmful algal blooms and neurological damage in marine mammals of the Pacific Ocean.

Domoic acid can bioaccumulate in marine organisms such as shellfish, anchovies, and sardines that feed on the phytoplankton known to produce this toxin. DA can accumulate in high concentrations in the tissues of these plankton feeders when the toxic phytoplankton itself is high in concentration in the surrounding waters.

In mammals, including humans, domoic acid acts as a neurotoxin, causing short-term memory loss, brain damage (including epilepsy[11][12]), in severe cases, death. DA-producing algal blooms are associated with the phenomenon of amnesic shellfish poisoning (ASP). In marine mammals, domoic acid typically causes seizures and tremors. 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 a normal event, the uncontrolled increase of calcium causes the cell 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.[13][14]

See also[edit]

References[edit]

  1. ^ a b c "Domoic Acid and Pseudo-nitzschia References". Fisheries and Oceans Canada. 2012-03-15. Retrieved 2012-04-08. 
  2. ^ Guiry, M. D.; Guiry, G. M. (2012). "Chondria armata (Kützing) Okamura". AlgaeBase. National University of Ireland. Retrieved 2012-04-08. 
  3. ^ Ramsdell, J. S. (2007). "The Molecular and Integrative Basis to Domoic Acid Toxicity". In Botana, L. M. Phycotoxins: Chemistry and Biochemistry. Cambridge, MA: Wiley-Blackwell. pp. 223–250. doi:10.1002/9780470277874.ch13. ISBN 0-8138-2700-0. 
  4. ^ "Nitzschia navis-varingica Lundholm & Moestrup, 2000". HABs taxon details. Marine Species. 
  5. ^ Kobayashi, K.; Takata, Y.; Kodama, M. (2009). "Direct Contact between Pseudo-nitzschia multiseries and Bacteria is Necessary for the Diatom to Produce a High Level of Domoic Acid" (pdf). Fisheries Science 75 (3): 771–776. doi:10.1007/s12562-009-0081-5. 
  6. ^ Bates, S. S.; Trainer, V. L. (2006). "The Ecology of Harmful Diatoms". In Granéli, E.; Turner, J. Ecology of Harmful Algae (pdf). Ecological Studies 189. Heidelberg: Springer-Verlag. pp. 81–93. doi:10.1007/978-3-540-32210-8_7. ISBN 978-3-540-74009-4. 
  7. ^ Trainer, V. L.; Hickey, B. M.; Bates, S. S. (2008). "Toxic Diatoms". In Walsh, P. J.; Smith, S. L.; Fleming, L. E.; Solo-Gabriele, H.; Gerwick, W. H. Oceans and Human Health: Risks and Remedies from the Sea. New York: Elsevier Science. pp. 219–237. ISBN 978-0-12-372584-4. 
  8. ^ a b Lelong, A.; Hégaret, H.; Soudant, P.; Bates, S. S. (2012). "Pseudo-nitzschia (Bacillariophyceae) Species, Domoic Acid and Amnesic Shellfish Poisoning: Revisiting Previous Paradigms". Phycologia 51 (2): 168–216. doi:10.2216/11-37.1. 
  9. ^ Trainer, V. L.; Bates, S. S.; Lundholm, N.; Thessen, A. E.; Cochlan, W. P.; Adams, N. G.; Trick, C. G. (2012). "Pseudo-nitzschia Physiological Ecology, Phylogeny, Toxicity, Monitoring and Impacts on Ecosystem Health". Harmful Algae 14: 271–300. doi:10.1016/j.hal.2011.10.025. 
  10. ^ Silver, M. W.; Bargu, S.; Coale, S. L.; Benitez-Nelson, C. R.; Garcia, A. C.; Roberts, K. J.; Sekula-Wood, E.; Bruland, K. W.; Coale, K. H. (2010). "Toxic Diatoms and Domoic Acid in Natural and Iron Enriched Waters of the Oceanic Pacific" (pdf). PNAS 107 (48): 20762–20767. doi:10.1073/pnas.1006968107. 
  11. ^ Cendes, F; Andermann, F; Carpenter, S; Zatorre, R. J.; Cashman, N. R. (1995). "Temporal lobe epilepsy caused by domoic acid intoxication: Evidence for glutamate receptor-mediated excitotoxicity in humans". Annals of Neurology 37 (1): 123–6. doi:10.1002/ana.410370125. PMID 7818246.  edit
  12. ^ http://onlinelibrary.wiley.com/doi/10.1002/cne.23509/abstract
  13. ^ Funk, Jason A.; Michael G. Janech; Joshua C. Dillon; John J. Bissler; Brian J. Siroky; P. Darwin Bell (8 February 2014). "Characterization of Renal Toxicity in Mice Administered the Marine Biotoxin Domoic Acid". Journal of the American Society of Nephrology 25 (2). doi:10.1681/ASN.2013080836. Retrieved 9 February 2014. 
  14. ^ Grush, Loren. "Safe’ levels of neurotoxin found in seafood may cause kidney damage". FoxNews.com Health. Fox News Network, LLC. Retrieved 10 February 2014. 

External links[edit]