Abstract
Ciguatera is a human intoxication caused by the ingestion of a variety ofreef fish. More than 20,000 victims suffer annually from ciguatera, makingit one of the largest-scale food poisoning of nonbacterial origin.Ciguatoxins are characterized as principal causative toxins of thepoisoning. Upon ingestion, these toxins cause various disorders involvingthe neurological, gastrointestinal and cardiovascular systems through thepotent activation of voltage-sensitive sodium channels. Ciguatoxins arelipophilic, cigar-shaped molecules, and consist of 13 fused ether rings,which spans over 3 nm.
In 2001, we achieved the first total synthesis of CTX3C, one of the mostimportant congeners of ciguatoxins, starting from D-glucose. To investigatethe detailed structure-activity relationship, various CTX3C analogs wereprepared from the synthetic intermediates. Evaluation of the activities ofthese analogs revealed that structural modulation of the central region ofthe molecule significantly changed the biological functions. In thispresentation, we will report chemistry and biology of ciguatoxins and theiranalogs. [Jpn J Physiol 54 Suppl:S9 (2004)]
