Kalinin V I, Prokofieva N G, Likhatskaya G N, Schentsova E B, Agafonova I G, Avilov S A, Drozdova O A
Pacific Institute of Bioorganic Chemistry, Far East Division of Russian Academy of Sciences, Vladivostok, Russia.
Toxicon. 1996 Apr;34(4):475-83. doi: 10.1016/0041-0101(95)00142-5.
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.
研究了该海参纲三萜糖苷及其衍生物诱导小鼠红细胞溶血和钾离子流失的情况。在末端单糖部分具有3 - O - 甲基基团的分支五糖苷中，连接在第一个木糖残基的4位和第三个葡萄糖残基的6位上的硫酸基团会增加钾离子流失。第一个木糖残基C - 4位的硫酸基团会增加溶血活性，而第三个单糖单元C - 6位的硫酸基团则会降低溶血活性。末端3 - O - 甲基葡萄糖C - 6位的硫酸基团会显著降低溶血活性和钾离子流失速率。在末端单糖没有3 - O - 甲基基团的糖苷中，第一个木糖残基存在硫酸基团会降低溶血活性和钾离子流失速率。在具有7(8) - 双键的苷元中存在16 - 酮基会显著降低活性。这些结果与先前提出的海参糖苷进化趋势相关，即从葡萄糖和3 - O - 甲基葡萄糖单元C - 6位有硫酸基团的物质演变为第一个木糖C - 4位硫酸化或没有硫酸基团的物质，以及从具有苷元16 - 酮基的物质演变为该位置没有氧官能团的物质。
