Gymnodimine-A

Gymnodimine

Last updated at: Sept. 22, 2023

Recommended name
Gymnodimine-A
Synonyms
Gymnodimine 1, Gymnodimine A
Recommended acronym
GYM-A
Abbreviation

Progenitors

Name
Karenia selliformis
Note
Seki et al., 1995 Haywood et al., 2004
Name
Alexandrium ostenfeldii
Note
Martens et al., 2017

Vector Species

Name
Ostrea chilensis
Note
Oysters (Tiostrea chilensis = Ostrea chilensis) MacKenzie et al., 1996 Stirling, 2001
Name
Perna canaliculus
Note
Stirling, 2001
Name
Pecten novaezelandiae
Note
Stirling, 2001
Name
Paphies australis
Note
Stirling, 2001
Name
Haliotis iris
Note
Stirling, 2001
Name
Mytilus galloprovincialis
Note
Stirling, 2001 Lamas et al., 2021
Name
Choromytilus meridionalis
Note
Krock et al., 2009
Name
Magallana hongkongensis
Note
Ji et al., 2022
Name
Pinctada imbricata
Note
Ji et al., 2022
Name
Antigona lamellaris
Note
Ji et al., 2022
Name
Marcia hiantina
Note
Ji et al., 2022
Name
Tegillarca granosa
Note
Ji et al., 2022
Name
Perna viridis
Note
Ji et al., 2022
Name
Ruditapes philippinarum
Note
Geng et al., 2022
Name
Anadara kagoshimensis
Note
Geng et al., 2022
Name
Dendrophysa russelii
Note
Li et al., 2021
Name
Evynnis cardinalis
Note
Li et al., 2021
Name
Johnius heterolepis
Note
Li et al., 2021
Name
Priacanthus macracanthus
Note
Li et al., 2021
Name
Trypauchen vagina
Note
Li et al., 2021
Name
Harpiosquilla harpax
Note
Li et al., 2021
Name
Metapenaeus affinis
Note
Li et al., 2021
Name
Metapenaeus ensis
Note
Li et al., 2021
Name
Portunus sanguinolentus
Note
Li et al., 2021
Name
Portunus trituberculatus
Note
Li et al., 2021
Name
Anadara ferruginea
Note
Li et al., 2021
Name
Bufonaria rana
Note
Li et al., 2021
Name
Fulvia australis
Note
Li et al., 2021
Name
Murex trapa
Note
Li et al., 2021
Name
Nassarius siquijorensis
Note
Li et al., 2021
Name
Turritella bacillum
Note
Li et al., 2021
Name
Magallana gigas
Note
Magallana gigas=Crassostrea gigas O'Neill et al., 2021
Name
Ruditapes decussatus
Note
De la Iglesia et al., 2013

References

Tetsuya Seki, 1995
Seki, T., Satake, M., Mackenzie, L., Kaspar, H. F., & Yasumoto, T. (1995). Gymnodimine, a new marine toxin of unprecedented structure isolated from New Zealand oysters and the dinoflagellate, Gymnodinium sp. Tetrahedron letters, 36(39), 7093-7096.
Allison J. Haywood, 2004
Haywood, A. J., Steidinger, K. A., Truby, E. W., Bergquist, P. R., Bergquist, P. L., Adamson, J., & Mackenzie, L. (2004). Comparative morphology and molecular phylogenetic analysis of three new species of the genus Karenia (Dinophyceae) from New Zealand 1. Journal of Phycology, 40(1), 165-179.
Helge Martens, 2017
Martens, H., Tillmann, U., Harju, K., Dell’Aversano, C., Tartaglione, L., & Krock, B. (2017). Toxin variability estimations of 68 Alexandrium ostenfeldii (Dinophyceae) strains from The Netherlands reveal a novel abundant gymnodimine. Microorganisms, 5(2), 29.
David J. Stirling, 2001
Stirling, D. J. (2001). Survey of historical New Zealand shellfish samples for accumulation of gymnodimine. New Zealand Journal of Marine and Freshwater Research, 35(4), 851-857.
Bernd Krock, 2009
Krock, B., Pitcher, G. C., Ntuli, J., & Cembella, A. D. (2009). Confirmed identification of gymnodimine in oysters from the west coast of South Africa by liquid chromatography–tandem mass spectrometry. African Journal of Marine Science, 31(1), 113-118.
Ying Ji, 2022
Ji, Y., Yan, G., Wang, G., Liu, J., Tang, Z., Yan, Y., ... & Li, A. (2022). Prevalence and distribution of domoic acid and cyclic imines in bivalve mollusks from Beibu Gulf, China. Journal of Hazardous Materials, 423, 127078.
Huixia Geng, 2022
Geng, H., Sun, H., Liu, C., Kong, F., Zhang, Q., Yan, T., & Yu, R. (2022). Screening for lipophilic marine toxins and their potential producers in coastal waters of Weihai in autumn, 2020. Journal of Oceanology and Limnology, 40(6), 2218-2230.
Jing Li, 2021
Li, J., Ruan, Y., Mak, Y. L., Zhang, X., Lam, J. C., Leung, K. M., & Lam, P. K. (2021). Occurrence and trophodynamics of marine lipophilic phycotoxins in a subtropical marine food web. Environmental Science & Technology, 55(13), 8829-8838.
J.Pablo Lamas, 2021
Lamas, J. P., Arévalo, F., Moroño, Á., Correa, J., Rossignoli, A. E., & Blanco, J. (2021). Gymnodimine A in mollusks from the north Atlantic Coast of Spain: Prevalence, concentration, and relationship with spirolides. Environmental Pollution, 279, 116919.
Simone Bacchiocchi, 2020
Bacchiocchi, S., Siracusa, M., Campacci, D., Ciriaci, M., Dubbini, A., Tavoloni, T., ... & Piersanti, A. (2020). Cyclic Imines (CIs) in Mussels from North-Central Adriatic Sea: First Evidence of Gymnodimine A in Italy. Toxins, 12(6), 370.
Alison O'Neill, 2021
O'Neill, A., Morrell, N., Turner, A. D., & Maskrey, B. H. (2021). Method performance verification for the combined detection and quantitation of the marine neurotoxins cyclic imines and brevetoxin shellfish metabolites in mussels (Mytilus edulis) and oysters (Crassostrea gigas) by UHPLC-MS/MS. Journal of Chromatography B, 1179, 122864.
De la Iglesia, P., 2013
De la Iglesia, P., McCarron, P., Diogène, J., & Quilliam, M. A. (2013). Discovery of gymnodimine fatty acid ester metabolites in shellfish using liquid chromatography/mass spectrometry. Rapid Communications in Mass Spectrometry, 27(5), 643-653.
Structure
Formula
C32H45NO4
Exact mono-isotopic mass
507.3349
Molfile
n/a
Alternative molfiles
n/a
SMILES
CC1CC2CCC(C(=CC3C(=C(CCC34CCCN=C4CCC=C(C1O2)C)C5C=C(C(=O)O5)C)C)C)O
Alternative SMILES
C[C@@H]1C[C@H]2CC[C@@H](/C(=C/[C@H]3C(=C(CC[C@@]34CCCN=C4CC/C=C(/[C@@H]1O2)\C)[C@@H]5C=C(C(=O)O5)C)C)/C)O
InChi key
DVXZVCNEGRKLMW-RPGUUIFVSA-N
Alternative InChi keys
n/a
InChi
InChI=1S/C32H45NO4/c1-19-8-6-9-29-32(13-7-15-33-29)14-12-25(28-18-22(4)31(35)37-28)23(5)26(32)17-20(2)27(34)11-10-24-16-21(3)30(19)36-24/h8,17-18,21,24,26-28,30,34H,6-7,9-16H2,1-5H3/b19-8+,20-17+/t21-,24-,26+,27+,28+,30+,32+/m1/s1
Alternative InChis
Spectra available
Unknown
Chem files

References

Michael Stewart, 1997
Stewart, M., Blunt, J. W., Munro, M. H., Robinson, W. T., & Hannah, D. J. (1997). The absolute stereochemistry of the New Zealand shellfish toxin gymnodimine. Tetrahedron Letters, 38(27), 4889-4890.
Certified
True
Certified links
Non certified reference material
True

Chemical analysis

Research
True
Standardized
Unknown
Validated
Unknown
Official
n/a

Structure recognition assays

Research
Unknown
Standardized
Unknown
Validated
Unknown
Official
n/a

Functional assays

Research
True
Standardized
Unknown
Validated
Unknown
Official
n/a

Animal assays

Research
True
Standardized
Unknown
Validated
Unknown
Official
n/a

References

Takeshi YASUMOTO, 1978
Mouse Bioassay Yasumoto, T., Oshima, Y., and Yamaguchi, M., 1978. Occurrence of a new type of shellfish poisoning in Tohoku district. Bull. Jpn. Soc. Sci. Fish. 44: 1249–1255.
OECD, 2001
Mouse Bioassay OECD, 2001. OECD Guideline for Testing of Chemicals 425. Acute Oral Toxicity—Up and Down Procedure. Organisation for Economic Co-operation and Development, Paris, France (http://www.epa. gov/oppfead1/harmonization/docs/E425guideline.pdf)
Lincoln MacKenzie, 2002
LC-MS/MS MacKenzie, L., Holland, P., McNabb, P., Beuzenberg, V., Selwood, A., & Suzuki, T. (2002). Complex toxin profiles in phytoplankton and Greenshell mussels (Perna canaliculus), revealed by LC–MS/MS analysis. Toxicon, 40(9), 1321-1330.
Paul McNabb, 2005
LC-MS/MS McNabb, P., Selwood, A. I., Holland, P. T., & Collaborators: Aasen J., Aune T., Eaglesham G., Hess P., Igarishi M., Quilliam M., Slattery D., Van de Riet J., Van Egmond H., Van den Top H., Yasumoto T. (2005). Multiresidue method for determination of algal toxins in shellfish: Single-laboratory validation and interlaboratory study. Journal of AOAC International, 88(3), 761-772.
Jiangbing Qiu, 2020
LC-MS/MS Qiu, J., Chen, H., Ji, Y., Li, T., & Li, A. (2020). Evaluation of different strategies to minimize the matrix effects on LC-MS/MS analysis of multiple lipophilic shellfish toxins in both acidic and alkaline chromatographic conditions. Toxicon, 188, 16-26.
Elie Fux, 2007
UPLC-MS/MS Fux, E., McMillan, D., Bire, R., & Hess, P. (2007). Development of an ultra-performance liquid chromatography–mass spectrometry method for the detection of lipophilic marine toxins. Journal of chromatography A, 1157(1-2), 273-280.
Laura P. Rodríguez, 2011
Functional Assays Rodriguez, L. P., Vilarino, N., Molgó, J., Aráoz, R., Antelo, A., Vieytes, M. R., & Botana, L. M. (2011). Solid-phase receptor-based assay for the detection of cyclic imines by chemiluminescence, fluorescence, or colorimetry. Analytical chemistry, 83(15), 5857-5863.
Natalia Vilariño, 2009
Functional Assays Vilarino, N., Fonfria, E. S., Molgo, J., Araoz, R., & Botana, L. M. (2009). Detection of gymnodimine-A and 13-desmethyl C spirolide phycotoxins by fluorescence polarization. Analytical chemistry, 81(7), 2708-2714.
RETURN TO ISSUEPREVARTICLENEXT Coupling the Torpedo Microplate-Receptor Binding Assay with Mass Spectrometry to Detect Cyclic Imine Neurotoxins Rómulo Aráoz, 2012
Functional Assays Aráoz, R., Ramos, S., Pelissier, F., Guérineau, V., Benoit, E., Vilariño, N., ... & Molgó, J. (2012). Coupling the Torpedo microplate-receptor binding assay with mass spectrometry to detect cyclic imine neurotoxins. Analytical chemistry, 84(23), 10445-10453.
Regulatory status
False
Human toxic syndrome(s)
n/a
Organ system toxicity
Neurotoxicity
Risk assessment
Unknown
Molecular targets known
True
Molecular targets
Nicotinic acetylcholine receptors
Toxic to aquatic animals
Unknown
TEF available
Unknown

Risk assessment References

Rex Munday, 2006
Munday, R. (2006). Toxicological requirements for risk assessment of shellfish contaminants: a review. African Journal of Marine Science, 28(2), 447-449.
Rex Munday, 2004
Munday, R., Towers, N. R., Mackenzie, L., Beuzenberg, V., Holland, P. T., & Miles, C. O. (2004). Acute toxicity of gymnodimine to mice. Toxicon, 44(2), 173-178.
Notes
Aifeng Li
Contact