G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 100 Let Vladivostoku prosp. 159, 690022 Vladivostok, Russian Federation.
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 100 Let Vladivostoku prosp. 159, 690022 Vladivostok, Russian Federation.
Carbohydr Polym. 2015 May 5;121:207-16. doi: 10.1016/j.carbpol.2014.12.042. Epub 2014 Dec 31.
A sulfated galactofucan SgF (MW 123kDa) was purified from the brown alga Saccharina gurjanovae. Polysaccharide was depolymerized by autohydrolysis at 25 and 60°C, and products were studied by mass spectrometry and (13)C NMR spectroscopy. According to results of investigation, the main chain of this polysaccharide is built of a repeating units →3)-α-L-Fucp-(2,4-OSO3(-))-(1→. Fucose chains could be sometimes terminated by (1→3)-linked galactose residues. Shorter (1→4)- and/or (1→6)-linked sulfated galactose chains are attached at positions C-2, C-3 of fucose residues. Sulfate groups can occupy positions C-2 and/or sometimes C-3 of Gal residues, but a sulfation at C-4 of the galactofucan could not be excluded. The SgF-AH25-H preparation (71kDa) was obtained by autohydrolysis of SgF at 25°C, which leaded to a selective desulfation at C-2 and, probably, to a cleavage of galactose chains, since structure of SgF-AH25-H represented a repeating unit →3)-α-l-Fucp-(4-OSO3(-))-(1→, which was definitely established by (13)C NMR spectroscopy. Galactofucan SgF and its derivative SgF-AH25-H exhibited no cytotoxic activity and leaded to about the same colony formation inhibition in colon cancer DLD-1 cells. Hence, structural simplification of SgF by lowering its molecular weight, desulfation at C-2 and removing of galactose residues by autohydrolysis at 25°C did not decrease its anticancer activity. This procedure allows obtaining standardized products which can be used as medical.
从褐藻糖胶 Saccharina gurjanovae 中纯化出一种硫酸化半乳甘露聚糖 SgF(MW 123kDa)。多糖通过 25 和 60°C 的自水解进行解聚,并用质谱和 (13)C NMR 光谱进行研究。根据研究结果,该多糖的主链由重复单元→3)-α-L-Fucp-(2,4-OSO3(-))-(1→组成。有时,岩藻糖链被(1→3)连接的半乳糖残基终止。较短的(1→4)-和/或(1→6)-连接的硫酸化半乳糖链连接在岩藻糖残基的 C-2、C-3 位置。硫酸基可以占据 Gal 残基的 C-2 和/或有时 C-3 位置,但不能排除半乳甘露聚糖 C-4 上的硫酸化。SgF 在 25°C 下自水解得到 SgF-AH25-H 制剂(71kDa),导致 C-2 选择性去硫酸化,并且可能导致半乳糖链断裂,因为 SgF-AH25-H 的结构代表一个重复单元→3)-α-l-Fucp-(4-OSO3(-))-(1→,这通过 (13)C NMR 光谱得到了明确证实。半乳甘露聚糖 SgF 及其衍生物 SgF-AH25-H 没有细胞毒性活性,并且在结肠癌细胞 DLD-1 中导致相同的集落形成抑制。因此,通过降低分子量、C-2 去硫酸化以及在 25°C 下自水解去除半乳糖残基来简化 SgF 的结构不会降低其抗癌活性。该方法允许获得标准化产品,可作为药物使用。