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.
Kalinin
V I
VI
Pacific Institute of Bioorganic Chemistry, Far East Division of Russian Academy of Sciences, Vladivostok, Russia.
Prokofieva
N G
NG
Likhatskaya
G N
GN
Schentsova
E B
EB
Agafonova
I G
IG
Avilov
S A
SA
Drozdova
O A
OA
D019325:3-O-Methylglucose / Q000378:metabolism; D000818:Animals; D002855:Chromatography, Thin Layer; D004305:Dose-Response Relationship, Drug; D004912:Erythrocytes / Q000166:cytology / Q000187:drug effects*; D006027:Glycosides / Q000737:chemistry / Q000633:toxicity*; D006461:Hemolysis / Q000187:drug effects; D006697:Holothurin / Q000737:chemistry / Q000633:toxicity; D007928:Lethal Dose 50; D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000737:chemistry / Q000633:toxicity*; D051379:Mice; D011188:Potassium / Q000378:metabolism; D012616:Sea Cucumbers / Q000378:metabolism*; D013329:Structure-Activity Relationship; D013431:Sulfates / Q000378:metabolism; D014315:Triterpenes / Q000737:chemistry / Q000633:toxicity*
D006027:Glycosides; D008387:Marine Toxins; D013431:Sulfates; D014315:Triterpenes; D006697:Holothurin; D019325:3-O-Methylglucose; C033504:cucumarioside; D011188:Potassium