- Recommended name
- Okadaic acid
- Synonyms
- 35-demethylDTX1, Acanthifolicin
- Recommended acronym
- OA
- Abbreviation
Progenitors
- Name
- Dinophysis fortii
- Name
- Dinophysis ovum
- Note
- The profilles of this species (of the "D. acuminata" complex) from two regions, Galiica (Spain) and Gulf of Mexico (USA) showed only OA
- Name
- Dinophysis sacculus
- Note
- Only traces of OA in cultured strains from Atlantic (Galicia, Spain) and Mediterranean (France) European coastal waters; both with predominance of PTX2 and only traces of DTX1
- Name
- Dinophysis acuminata
- Note
- This species has strains with profiles containing: i) High content of OA (> 40 pg/cell) ONLY in the European Atlantic Arc; 1 strain in ii) Dominated by PTX2 and low to moderate (1-10 pg/cell) DTX-1 in NE USA, and eastern Japan. The same profile in net tows with D acuminata in southern Chile and picked cells iii) High in other congeners (DTX1 but no OA) and PTXs (NW USA and Canada) iv) No OA related toxins; only PTXs in Atacama (N Chile) and Danish fjords
- Name
- Dinophysis miles
- Note
- High content of OA in HPLC analyses of picked cells in The Philippines. Cultures needed to confirm de novo production
- Name
- Dinophysis norvegica
- Note
- Only traces of OA in Northern European and Japanese strains with high content of PTXs No OA in NE USA cultured strains with a profile dominated by PTX-12 and only one congener of OA, dihydro-DTX1. Only PTXs in NW US strains
- Name
- Dinophysis acuta
- Note
- Most strains have a combination of 1.okadaates: OA and DTX1 or DTX2 and minor contribution of diol esters (OA-D7, OA-D8, OA-D9) 2. PTXs: PTX2 (dominant), PTX-11 with a few exceptions having only PTXs
- Name
- Prorocentrum caipirignum
- Note
- Nascimento et al 2017
- Name
- Prorocentrum concavum
- Note
- Hu et al 1993
- Name
- Prorocentrum lima
- Note
- Murakami et al 1982
- Name
- Prorocentrum rhathymum
- Note
- Caillaud et al 2010
- Name
- Prorocentrum texanum
- Note
- Gulf of Mexico
- Name
- Dinophysis caudata
- Note
- High content of OA in HPLC analyses of picked cells in The Philippines. Cultures needed to confirm de novo production OA eventually found in LC-MS analyses of picked cells in the Galician Rías (NW Spain). Not found in cultures of only 2 strains tested
Vector Species
- Name
- Cancer pagurus
- Name
- Mytilus edulis
References
- Sechet, V.; Sibat, M.; Billien, G.; Carpentier, L.; Rovillon, G. A.; Raimbault, V.; Malo, F.; Gaillard, S.; Perriere-Rumebe, M.; Hess, P., 2021
- Distinct toxin profiles in French strains of species of the "D. acuminata complex": D. acuminata (Atlantic coast) and D. sacculus (Mediterranean) coast)
- Marasigan, A. N.; Sato, S.; Fukuyo, Y.; Kodama, M., 2001
- Marasigan, A. N.; Sato, S.; Fukuyo, Y.; Kodama, M. Accumulation of a high level of diarrhetic shellfish toxins in the green mussel Perna viridis during a bloom of Dinophysis caudata and Dinophysis miles in Saipan Bay, Panay Island, the Philippines. Fish. Sci. 2001, 67, 994-996
- Structure
-
- Formula
- C44H68O13
- Exact mono-isotopic mass
- 804.46599
- Molfile
- n/a
- Alternative molfiles
- n/a
- SMILES
- OC([C@](C)(O)C[C@@H]1CC[C@@H](O)[C@@]2(O[C@H]([C@H](C)/C=C/[C@@H]3O[C@]4(CC[C@@H](O[C@H]([C@@H](O)C[C@H](C)[C@H]5O[C@@]6(CCCCO6)CC[C@H]5C)C([C@H]7O)=C)[C@H]7O4)CC3)CC(C)=C2)O1)=O
- Alternative SMILES
- OC([C](C)(O)C[CH]1CC[CH](O)[C]2(O[CH]([CH](C)/C=C/[CH]3O[C]4(CC[CH](O[CH]([CH](O)C[CH](C)[CH]5O[C]6(CCCCO6)CC[CH]5C)C([CH]7O)=C)[CH]7O4)CC3)CC(C)=C2)O1)=O
- InChi key
- QNDVLZJODHBUFM-WFXQOWMNSA-N
- Alternative InChi keys
- n/a
- InChi
- InChI=1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2
- Alternative InChis
- Spectra available
- True
- Chem files
- chemfiles/OA-NVI-2019.cdx chemfiles/OA-NVI-2019.mol
References
- , 2019
- Chemical information (structure picture, chemdraw-file, mol-file, SMILES & InChI and InChI-key have been derived from the NVI structure template updated in 2019 and created in Chemdraw (as per file attached). Molecular formula and structure based on Tachibana et al., 1981.
- Certified
- True
- Certified links
-
- EURLMB
Certified and non-certified reference materials are listed
- EURLMB
- Non certified reference material
- True
Chemical analysis
- Research
- True
- Standardized
- True
- Validated
- True
- Official
- EURLMB (EU-harmonised protocol)
Structure recognition assays
- Research
- True
- Standardized
- False
- Validated
- False
- Official
- n/a
Functional assays
- Research
- True
- Standardized
- False
- Validated
- False
- Official
- n/a
Animal assays
- Research
- True
- Standardized
- True
- Validated
- False
- Official
- n/a
References
- EURLMB, 2015
- EU REFERENCE LABORATORY FOR MONITORING OF MARINE BIOTOXINS EU-Harmonised Standard Operating Procedure for determination of Lipophilic marine biotoxins in molluscs by LC-MS/MS
- EURLMB, 2010
- METHOD FOR DETECTION OF OKADAIC ACIDTOXINS GROUP IN EDIBLE MOLLUSCS Rev 4 October 2010 Standard Operating Procedures method for the quantitative determination of OA and other carboxylic toxins of the OA group including DTX1, DTX2, DTX3 by a colorimetric phosphatase inhibition assay. The OkaTest method fulfils the requirements of Chapter III A (4) a, b, and c of Annex III to Regulation (EC) 2074/2005 and can be used as supplementary method to EU-RL LC/MS/MS method only for the detection of Okadaic Acid group toxins OA, DTX1,DTX2, DTX3 including their esters. The use of OkaTest method is not an alternative to the EU-RL LC/MS/MS method.
- Regulatory status
- True
References
- Lawrence, J., et al., 2011
- Lawrence, J.; Loreal, H.; Toyofuku, H.; Hess, P.; Iddya, K.; Ababouch, L. Assessment and management of biotoxin risks in bivalve molluscs. FAO Fisheries and Aquaculture Technical Paper No. 2011, 551, 337 pages. Website: http://www.fao.org/3/i2356e/i2356e.pdf, last accessed 10/02/2023.
- Human toxic syndrome(s)
- Diarrhetic Shellfish Poisoning
- Organ system toxicity
- Gastro-intestinal toxicity
- Risk assessment
- True
- Molecular targets known
- True
- Molecular targets
- Protein phosphatase 2A, Protein phosphatase 1
- Toxic to aquatic animals
- True
- TEF available
- True
Risk assessment References
- EFSA, 2008
- EFSA. Marine biotoxins in shellfish - Okadaic Acid and analogues, Scientific Opinion of the Panel on Contaminants in the Food chain, adopted on 27 November 2007. EFSA Journal 2008, 589, 1-62. Last accessed 10/02/2023
- Lawrence, J., et al., 2011
- Lawrence, J.; Loreal, H.; Toyofuku, H.; Hess, P.; Iddya, K.; Ababouch, L. Assessment and management of biotoxin risks in bivalve molluscs. Website: http://www.fao.org/3/i2356e/i2356e.pdf, last accessed 27/08/2021. FAO Fisheries and Aquaculture Technical Paper No. 2011, 551, 337 pages.
TEF References
- FAO, 2016
- FAO/WHO. 2016. Technical paper on Toxicity Equivalency Factors for Marine Biotoxins Associated with Bivalve Molluscs. Rome. 108 pp.
- Botana, L., et al., 2017
- Botana, L. M.; Hess, P.; Munday, R.; Nathalie, A.; DeGrasse, S. L.; Feeley, M.; Suzuki, T.; van den Berg, M.; Fattori, V.; Gamarro, E. G.; et al. Derivation of toxicity equivalency factors for marine biotoxins associated with Bivalve Molluscs. Trends in Food Science & Technology 2017, 59, 15-24.
- Notes
References
- Tachibana, K., et al., 1981
- Bibliographic reference of original description: Tachibana, K., et al., Okadaic acid, a cytotoxic polyether from two marine sponges of the genus Halichondria. Journal of the American Chemical Society, 1981. 103(9): p. 2469-2471.
- Larsen, K., et al., 2007
- Larsen, K.; Petersen, D.; Wilkins, A. L.; Samdal, I. A.; Sandvik, M.; Rundberget, T.; Goldstone, D.; Arcus, V.; Hovgaard, P.; Rise, F.; et al. Clarification of the C-35 stereochemistries of dinophysistoxin-1 and dinophysistoxin-2 and its consequences for binding to protein phosphatase. Chem. Res. Toxicol. 2007, 20 (6), 868-875, Article. DOI: 10.1021/tx700010m.