Gymnodimines

Gymnodimine and 13- Shellfish Fluorescence polarization inhibition assay 80-2,000 pg kg" and [81] Z... 

A hydrotelluration reaction, followed by a tellurium-lithium exchange, was used in the first step of the total synthesis of Gymnodimine 182 (Scheme 100).257... 

Several studies have been carried out for the synthesis of gymnodimine-components (Ahn et al. 2001 White et al. 2003 Johannes et al. 2005 Kong et al. 2005), but the total synthesis has yet to be achieved. The synthesis and production of intermediate components of gynmodimine appears essential for providing inummogens that will help its toxic monitoring in shellfish by methods other than the mouse bioassay. 

Gymnodimine elicits highly toxic effects when administered either by intraperitoneal (Eire et al. 2002 Munday et al. 2004), subcutaneous or intracerebroventricular injection to mice (Kharrat et al. 2006). Symptoms after intraperitoneal injection included hyperactivity, jumping, curled tail, paralysis of the hind legs, severe dyspnea, followed by rapid death within 6-15 minute of injection. The mean LDjq after intraperitoneal of highly purified gynmodimine was found to be 96 pg kg (Munday et al. 

Ahn, Y., Cardenas, G.I., Yang, J., and Romo, D. 2001. Studies toward gymnodimine development of a single-pot Hua reaction for the syndiesis of highly hindered cyclic imines. OrgLett. 3, 751—754. 

Bire, R., Krys, S., Fremy, J.M., Dragacci, S., Stirling, D., and Kharrat, R. 2002. First evidence on occurrence of gymnodimine... 

Johannes, J.W., Wenglowsky, S. and Kishi, Y, 2005. Biomimetic macrocycle-forming Diels-Alder reaction of an iminium dienophile synthetic studies directed toward gymnodimine. OrgLett 7, 3997-4000. 

Kharrat, R., Servent, D., Girard, E., Ouanounou, G., and Molgo, J 2006. Gymnodimine broadly targets nicotinic acetylcholine receptors. Submitted. 

Kong, K., Moussa, Z. and Romo, D., 2005. Studies toward a marine toxin immunogen enantioselective synthesis of the spiro-cyclic imine of (-)-gymnodimine. Org Lett 7, 5127-5130. 

MacKenzie, L., Haywood, A., Adamson, J, Truman, E, Till, D., Seki, T, Satake, M. and Yasumoto, T, 1996. Gymnodimine contamination of shellfish in New Zealand. InHarmJul andToxic Algal Blooms, ed. Yasumoto T, Oshima Y, and Fukuyo Y. Paris Intergovernmental Oceanographic Commission of UNESCO, 97—100. 

Miles, C.O., Wilkins, A.L., Stirling, D.J., and MacKenzie, A.L. 2000. New analogue of gymnodimine from a Gymnodinium species. JAgric Food Chem 48, 1373—1376. 

Gymnodimine C, an isomer of gymnodimine B, fromKarenia selliformis. J Agric Food Chem 51, 4838-4840. 

Seki, T, Satake, M., MacKenzie, L., Kaspar, H., and Yasumoto, T. 1995. Gymnodimine, a new marine toxin of unprecedented structure isolated from New Zealand oysters and the dinoflagellate, Gymnodinium sp. Tetrahedron Lett 36, 7093-7096. 

Gymnodimine, a novel toxic imine isolated from the Foveaux Strait oysters and Gymnodinium sp. In Harmful... 

Stirling, D.J. 2001. Survey of historical New Zealand shellfish samples for accumulation of gymnodimine. NZ J Mar Fresh-watRes 35, 851-857. 

White, J.D., Wang, G. and Quaranta, L., 2003. Studies on the synthesis of gymnodimine. Stereocontrolled construction ofthe tetrahydrofuran subunit. Org Lett 5, 4109-4112. 

Glycogen synthase kinasc-3[) (GSK-3(1) regulators Acetyl-2-carnitine AZD1080 CHIR 99021 CID 56840716/ML320 CID5706819 Falcarindiol Gymnodimine... 

Uncariae Uncis cum Ramulus Kaixin San formulas Karenia selliformis Gymnodimine... 

In synthetic studies directed toward the natural product gymnodimine, Kishi and co-workers epoxidized compound 21 using m-CPBA to yield 22.17... 

No information of harmful effects is documented on human exposed to gymnodimin, spirolides, or pinnatoxins in shellfish [3]. 

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