Abstract
In recent decades, more than 130 potentially toxic metabolites originating from dinoflagellate species belonging to the genus Karenia or metabolized by marine organisms have been described. These metabolites include the well-known and large group of brevetoxins (BTXs), responsible for foodborne neurotoxic shellfish poisoning (NSP) and airborne respiratory symptoms in humans. Karenia spp. also produce brevenal, brevisamide and metabolites belonging to the hemi-brevetoxin, brevisin, tamulamide, gymnocin, gymnodimine, brevisulcenal and brevisulcatic acid groups. In this review, we summarize the available knowledge in the literature since 1977 on these various identified metabolites, whether they are produced directly by the producer organisms or biotransformed in marine organisms. Their structures and physicochemical properties are presented and discussed. Among future avenues of research, we highlight the need for more toxin occurrence data with analytical techniques, which can specifically determine the analogs present in samples. New metabolites have yet to be fully described, especially the groups of metabolites discovered in the last two decades (e.g tamulamides). Lastly, this work clarifies the different nomenclatures used in the literature and should help to harmonize practices in the future.
Highlights
Introduction iationsThe genus Karenia belongs to the clade of the alveolates
The aim of this review is to summarize the knowledge collected in recent decades about the potentially toxic metabolites produced by Karenia spp. or reported in other marine organisms
Individual analogs have been reported worldwide (Figure 1), whereas data are lacking for the other groups of metabolites produced by Karenia spp. [10,20–27,30–33,35–47]
Summary
LogP predicted from the chemical structure of molecules using the ACD/Labs platform. Octanol/water partition coefficients were predicted using algorithms. Synthesized toxin, unidentified in cultures to date, but postulated to occur naturally, based on structural correlation with BTX-9 and its presence in stationary cultures. Analogs postulated after thorough study of LC-MS/MS fragmentations. The implementation of specific methods for the analysis of metabolites produced by Karenia spp. allowed for the identification of individual analogs belonging to several of these groups of toxins in Australia, Japan, New Zealand, the Gulf of Mexico and the South.
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