Gymnodinium breve

This lithiated epoxysulfone cyclisation strategy has been iteratively applied in the total synthesis of hemibrevitoxin B, a polycyclic ether marine toxin from the red tide organism Gymnodinium breve (Scheme 5.41) [64]. 

Paralytic neurotoxins that bind to sodium channels of nerve and muscle cells causing muscle contractions. They are obtained from the dinoflagellate that causes "red-tide" (Gymnodinium breve). Toxins are typically light tan crystalline solids. They are insoluble in water and very unstable. 

Naar, J., et ah, A competitive ELISA to detect brevetoxins from Karenia brevis (formerly Gymnodinium breve) in seawater, shellfish, and mammalian body fluid, Env. Health Perspect., 110, 2, 179, 2002. 

Perez, E., Sawyers, W. and Martin, D., Identification of allelopathic substances produced by Nannochloris aculata that affects a red tide organism Gymnodinium breve, Biomed. Lett., 56, 7, 1997. 

Perez, E., Sawyers, W.G. and Martin, D.F., Lysis of Gymnodinium breve by cultures of the green alga Nannochloris eucaryotum, Cytobios, 104, 405, 25, 2001. 

Sengco, M., Removal of red and brown tide cells using clay flocculation I. Laboratory culture experiments with Gymnodinium breve and Aureococcus anophagejferens. Mar. Ecol. Prog. Ser., 2003. 

In B.C. they are usually separated distributionally, but intermediate forms occur in intermediate localities. In Japan they may be temporally separated.The allocation of Gymnodinium breve to Ptychodiscus depends on the presence of a pellicle. Although not seen with TEM it can be seen with light microscopy. Geographic distribution is closely linked to taxonomy for, although some toxin producers appear to be endemic in a restricted sense, closely similar forms occur elsewhere (e.g.p, brevis) or the same species may be known by different names in different regions ( Gyrodinium aureolum ). 

Perhaps the most unusual marine metabolites from the Caribbean are con lex polyketides, called brevetoxins, produced by a toxic dinoflagellate, Gymnodinium breve (Chart 7.3.FA/PO). 

Poiyether hemibrevetoxins Gymnodinium breve Davis [= Ptychodiscus brevis Davis], free Dinofl. Prasad 1989) brevetoxin-A-class Gymnodinium breve, free Dinofl. Rein 1994). 

Neurotoxic Shellfish Poisoning (NSP) is caused by a red-tide producer that was first identified in 1880 from Florida, with earlier historical references. It causes sickness in humans lasting several days. NSP is not fatal to humans however, it is known to kill fish, invertebrates, seabirds, and marine mammals (e.g., manatees). It is caused by the brevetoxin family (brevetoxin + 10 related compounds produced by the dinoflagellate Karenia brevis a.k.a. Gymnodinium breve. The main contamination problems include oysters, clams, and other filter feeders of the Gulf of Mexico and southeast Atlantic, including North Carolina. 

Baden, D.G., and Mende, T.J. 1982. Toxicity of two strains from the Florida red tide marine dinoflagellate, Gymnodinium breve. Toxicon 20, 457-461. 

Dickey, R., Jester, E., Granade, R., Mowdy, D., Monereiff, C., Rebarchik, D, Robl, M., Musser, S., Poli, M. 1999. Monitoring brevetoxins during a Gymnodinium breve red tide comparison of sodium channel specific cytotoxicity assay and mouse bioassay for determination of neurotoxic shellfish toxins in shellfish extracts. Natural Toxins 1, 157-165. 

Husain, K., Singh, R., Kaushik, M.P., and Gupta, A.K. 1996. Acute toxicity of synthetic Gymnodinium breve toxin metabolite and its analogues in mice. Ecotoxicol Environ Safety 35, 77-80. 

Lin, Y.Y., Risk, M., Ray, S.M., Vanengen, D, Clardy, J, Golik, J, James, J.C., Nakanishi, K. 1981. Isolation and structure of brevetoxin-B from the red tide dinofiagellate Ptychodiscus brevis (Gymnodinium, Breve). Journal ofthe American Chemical Society 103, 6773-6775. 

Pierce, R.H. 1986. Red tide (Gymnodinium breve ) toxin aerosols a review. Toxicon 24, 955-965. 

Lee MS, Qin GW, Nakanishi K, Zagoeski MG. Biosynthetic studies of brevetoxins, potent neurotoxins produced by the dinofiagel-late Gymnodinium breve. J. Am. Chem. Soc. 1989 111 6234-6241. 

Only one naturally occurring azide has been reported to date. 6-Azidotetrazolo[5,l-u]phthalazine (6) was isolated, by chloroform extraction and subsequent chromatographic purification, from unialgal cultures of Gymnodinium breve (Ptychodiscus brevis), a dinoflagellate responsible for the production of toxic red tides along the Gulf Coast of Florida [16]. The structure of this extraordinary secondary metabolite was determined by... 

An extract of the digestive glands of P. yessoensis, collected fiom the aforementioned location, upon fractionation gave a new polyether toxin, yessotoxin[114]. The structure of which was determined by spectroscopic methods (92) and has the chemical characteristics of dinoflagellate toxins isolated from Gymnodinium breve (93). Recently, toxic mussels collected from Ban try Bay, Ireland, were found to contain dinophysistoxin-2 (DTX2) [115] (94). 

Brevetoxin B is one of a family of polyethers found in a sea creature (a dinoflagellate Gymnodinium breve, hence the name) which sometimes multiplies at an amazing rate and creates red tides around the coasts of the Gulf of Mexico. Fish die in shoals and so do people if they eat the shellfish that have eaten the red tide. The brevetoxins are the killers. The many ether oxygen atoms interfere with sodium ion (Na ) metabolism. 

Lipophilic polyether neurotoxin produced by red tide dinoflagellate gymnodinium breve... 

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