Hemolytic activities of triterpene glycosides from the holothurian order Dendrochirotida: some trends in the evolution of this group of toxins.

Hemolysis and K+ loss from mouse erythrocytes, induced by triterpene glycosides and their derivatives from this order of sea cucumbers were studied. Sulfate groups, attached to position 4 of the first xylose residue and to position 6 of the third glucose residue of the branched pentaosides, having 3-O-methyl-groups in terminal monosaccharide moieties increase K+ loss. A sulfate group at C-4 of the first xylose residue increases the hemolytic activity while a sulfate at C-6 of the third monosaccharide unit decreases it. A sulfate group at C-6 of terminal 3-O-methylglucose drastically decreases the hemolytic activity and rate of K+ loss. The presence of a sulfate group at the first xylose residue in glycosides having no 3-O-methyl group at the terminal monosaccharide decreases hemolytic activity and rate of K+ loss. The presence of the 16-ketone group in aglycones having the 7(8)-double bond significantly decreases activity. These results correlate with the previously proposed trends in evolution of sea cucumber glycosides from substances having sulfate groups at C-6 of glucose and 3-O-methylglucose units to substances sulfated at C-4 of the first xylose or having no sulfate groups, and from substances with aglycone 16-ketone to substances having no oxygen functions in this position.