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

Abstract

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.

• Authors: V I Kalinin, N G Prokofieva, G N Likhatskaya, E B Schentsova, I G Agafonova, S A Avilov, O A Drozdova
• Journal: Toxicon : official journal of the International Society on Toxinology (Toxicon) Vol. 34 Issue 4 Pg. 475-83 (Apr 1996) ISSN: 0041-0101 [Print] England
• PMID: 8735247 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Glycosides
• Marine Toxins
• Sulfates
• Triterpenes
• Holothurin
• 3-O-Methylglucose
• cucumarioside
• Potassium

Topics

• 3-O-Methylglucose (metabolism)
• Animals
• Chromatography, Thin Layer
• Dose-Response Relationship, Drug
• Erythrocytes (cytology, drug effects)
• Glycosides (chemistry, toxicity)
• Hemolysis (drug effects)
• Holothurin (chemistry, toxicity)
• Lethal Dose 50
• Magnetic Resonance Spectroscopy
• Marine Toxins (chemistry, toxicity)
• Mice
• Potassium (metabolism)
• Sea Cucumbers (metabolism)
• Structure-Activity Relationship
• Sulfates (metabolism)
• Triterpenes (chemistry, toxicity)