Maitotoxin (Molecule of the Month for May 2020)
Maitotoxin is an extremely potent toxin produced by Gambierdiscus toxicus, a single celled marine plankton dinoflagellate species. The plankton is found most commonly attached to seaweed. Maitotoxin was named from the ciguateric fish Ctenochaetus striatusócalled "maito" in Tahitiófrom which maitotoxin was isolated for the first time after its detection in the gut of the striated surgeonfish. The striated surgeonfish is known one of the few herbivorous fishes which are occasionally toxic. Ciguatera poisoning is caused by the accumulation of a toxin produced by the plankton which it ingests while feeding on algae/seaweed. If a contaminated fish is eaten by humans, the concentrated poison contained within its tissues causes neurological damage that can be fatal.
Maitotoxin is so potent that it has been demonstrated that an intraperitoneal injection of 130 ng/kg was lethal in mice, giving it a of LD50 = 50 nano grams/kg
The molecule itself is a system of 32 fused rings. It resembles large fatty acid chains and it is notable because it is one of the largest and most complex non-protein, non-polysaccharide molecules produced by any organism. Maitotoxin includes 32 ether rings, 22 methyl groups, 28 hydroxyl groups, and 2 sulfuric acid esters and has an amphipathic structure. Since 1996 the Nicolaou research group is involved in an effort to synthesise the molecule via total synthesis, who described the neurotoxin with "an elegant molecular structure which represents the largest and most complex secondary metabolite ever isolated".
Formal Chemical Name (IUPAC)
Update by Karl Harrison
(Molecule of the Month for May 2020 )
All the images on this web site are are made available with a Creative Commons Attribution license and so can be used as long as the attribution © Karl Harrison 3DChem.com is written with the image. High resolution images and illustrations are available on request.