N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russia.
Kamchatka Branch of Pacific Geographical Institute FEB RAS, Russian Academy of Sciences, Petropavlovsk-Kamchatsky 683000, Russia.
Mar Drugs. 2018 Oct 17;16(10):389. doi: 10.3390/md16100389.
Fucosylated chondroitin sulfate was isolated from the sea cucumber collected from the Avachinsky Gulf of the eastern coast of Kamchatka. Structural characterization of was performed using a series of non-destructive NMR spectroscopic procedures. The polysaccharide was shown to contain a chondroitin core [→3)-β-d-GalNAc-(1→4)-β-d-GlcA-(1→] where about 60% of GlcA residues were 3-O-fucosylated, while another part of GlcA units did not contain any substituents. The presence of unsubstituted both at O-2 and O-3 glucuronic acid residues in a structure of holothurian chondroitin sulfate is unusual and has not been reported previously. Three different fucosyl branches Fuc24, Fuc34 and Fuc4 were found in the ratio of 2:1:1. The GalNAc units were mono- or disulfated at positions 4 and 6. Anti-inflammatory activity of was assessed on a model of acute peritoneal inflammation in rats. About 45% inhibition was found for , while a structurally related linear chondroitin sulfate from cartilage of the fish demonstrated only 31% inhibition, indicating that the presence of sulfated fucosyl branches is essential for anti-inflammatory effect of chondroitin sulfates of marine origin.
从堪察加东海岸阿瓦恰湾采集的海参中分离得到了岩藻糖基硫酸软骨素。采用一系列非破坏性 NMR 光谱程序对其结构进行了表征。该多糖含有一个软骨素核心[→3)-β-d-GalNAc-(1→4)-β-d-GlcA-(1→]，其中约 60%的 GlcA 残基被 3-O-岩藻糖基化，而 GlcA 单元的另一部分不含任何取代基。在海胆硫酸软骨素的结构中，存在未取代的 O-2 和 O-3 葡萄糖醛酸残基是不寻常的，以前没有报道过。在该结构中发现了三种不同的岩藻糖支链 Fuc24、Fuc34 和 Fuc4，其比例为 2:1:1。GalNAc 单元在 4 位和 6 位单硫酸化或二硫酸化。在大鼠急性腹膜炎模型上评估了 的抗炎活性。发现 对炎症的抑制率约为 45%，而结构上与之相关的来自鱼类软骨的线性硫酸软骨素 仅抑制 31%，表明硫酸化岩藻糖支链的存在对于海洋来源的硫酸软骨素的抗炎作用是必需的。
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