Fast death factor

Three different toxins have been associated with Microcystis aeruginosa. The most common of these is a fast death factor (FDF,... 

The use of nitrones in the synthesis of anatoxin-a, very fast death factor. Tetrahedron 41, 3447-3453, and references therein about the regioselectivity of nitrone cyclization. 

Nearly 60 mieroeystin eyelie hepatopeptides have been identified of whieh mieroeystin-LR, also known as the fast death factor, is the most eommon, and the toxin of choice to be weaponized (Craig et al, 1993 Rinehart et. al, 1994). This toxin has been reported to be responsible for the deaths of wild animals and agrieultural livestock (Carmichael, 1988). A potential threat to the health of humans has been recognized in eountries where water supplies are contaminated with cyanobaeteria (Yu, 1989). In 1996, microcystin-LR was also implieated in the death of 50 Brazilian dialysis patients (Jochimsen et al, 1998). 

Interestingly, the balance can be tipped toward formation of the seven-membered ring by simply placing an electron-withdrawing group on the terminal carbon of the dipolarophile (Scheme IS). Tliis leads to polarization of the alkene and to an FMO-controlled process. Incidentally, the reaction shown proved critical in a total synthesis of anatoxin a, the so-called very fast death factor . ... 

The opening of halocyclopropanes to allyl systems according to equation 124 can happen thermally or with the assistance of electrophiles and nucleophiles . Some recent examples include an efficient cyclopentenone synthesis (equation 125) ", an electrocyclic opening/cyclization sequence giving functionalized furan and pyran derivatives (equation 126), an elegant total synthesis of the very fast death factor alkaloid ( ) anatoxin and a nice application of the well known nucleophilic opening to the preparation of crystalline methylene aziridines (equation 127) . 

Cyanobacteria toxins (sometimes referred to as blue green algal toxins) are represented in this entry by Aplysiatoxins, which are toxic to the skin, and anatoxin a (CAS 64285-06-9, C10H15NO) and anatoxin a (S) (very fast death factor), which are neurotoxins. Saxitoxin, discussed earlier, and neo-saxitoxin are both neurotoxins that may also be classified as cyanobacterial toxins. A large variety of other toxins is produced by cyanobacteria, but is not as well documented. These include lyngbyatoxin (dermatotoxic) cyclic peptides predominantly microcystins, nodularins, and cylindro-spermopsin (hepatotoxins) endotoxins and other substances as yet undescribed, including additional tumor promoters. 

Anatoxin-a (very fast death factor) from the cyanobacterium Anabaena... 

Bishop, C.T., Anet, E.F., and Gorham, P.R., Isolation and identification of the fast-death factor in Microcystis aeruginosa. Can. J. Biochem. Physiol., 37, 453, 1959. 

In 1878 George Francis published the first written report of animal poisoning by a Cyanobacterium (blue-green alga). However, only in the last 30 years have significant amounts of information appeared on the structure and function of neurotoxin alkaloids and hepatotoxic peptides. Only the latter are discussed here. The peptide nature of the isolated fast death factor was recognized in 1959 by C.J. Bishop et al. [57] the structure of cyanoginosin-LA was revealed only in 1984 by Botes et al. (Fig. 25) [58]. 

Anatoxin A is the fast-acting and highly effective poison of the cyanobacterium Anabaenaflos-aquae, which is ubiquitous in freshwater. Anatoxin A, also known as Very Fast Death Factor , was isolated from Anabaenaflos-aquae in 1977 by Paul Gorham at the National Research CoimcU in Ottawa. [553,554] The structure had already been determined in 1972 by X-ray analysis of its N-acetyl derivative. [555] Later, the presence of anatoxin A was detected in a range of other toxic strains of Oscillatoria, Anabaena circinalis, Aphanizomenonflos-aquae, Cylindorsperum pp. and Raphidiopsis mediterranea. 

The structure and toxic symptoms of pinnamine resemble those of anatoxin-a (11) [19,20], a potent postsynaptic depolarizing neurotoxin known as very fast death factor (VFDF), and atropine [21], a representative suppressor of the... 

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