Toxins from sea cucumbers (holothuroids): chemical structures, properties, taxonomic distribution, biosynthesis and evolution.

Studies on structures, biological activities, chemical properties, taxonomic distribution, biosynthesis, and evolution of toxins from sea cucumbers (the phylum Echinodermata, the class Holothurioidea) were reviewed with special emphasis on recent results from our laboratory. These toxins are triterpene oligoglycosides having very often one or several sulfate groups in carbohydrate moieties. Their aglycones belong to lanostane derivatives and sometimes contain shortened side chains. Many aglycones are labile in the acid medium. There is a relationship between structures of the glycosides and taxonomic positions of corresponding animals, producers of these toxins. Toxins from sea cucumbers act on delta 5-sterol-containing biological membranes with the formation of glycoside-sterol complexes followed by the disturbance of membrane permeability and inhibition of activities of some membrane enzymes. The presence of the toxins causes the alterations in membrane sterol compositions of toxic sea cucumbers in comparison with non-toxic species. These alterations include the change of delta 5-sterols for those having 7(8)- and 9(11)-double bonds as well as biotransformation of a part of free sterol fractions into sterol sulfates and sterol xylosides.