Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum
Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum
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DOI：
10.1016/j.phytochem.2006.05.024
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发表时间：
2006-11-01
期刊：
影响因子：
3.8
通讯作者：
Ray, Bimalendu
中科院分区：
文献类型：
--
作者：
Adhikari, Utpal;Mateii, Cecilia G.;Ray, Bimalendu
从阿拉伯海收集的棕色海藻 Stoechospermum marginatum 的水提取物中分离出含有硫酸化岩藻聚糖的级分 (SmWE)。粗馏分的阴离子交换色谱导致产生硫酸化岩藻聚糖(F3)，其具有40kDa的分子量和比旋光度α(D)(30)-124度(c 0.5，H(2)O)。 NMR 波谱研究和甲基化分析表明，该聚合物由 (1 -> 4)- 和 (1 -> 3)-连接的 -α-L-吡喃岩藻糖基残基组成，这些残基在 C-2 和 C-3 处被取代，并且岩藻糖基残基大部分在 C-2 和/或 C-4 处被硫酸化。 SmWE和F3是Vero细胞中单纯疱疹病毒I型（F株、胸苷激酶缺陷株field和B2006以及用天然角叉菜胶syn 13-8和14-1选择后产生的合胞体变体）和2型（MS株）的选择性抑制剂，抗病毒有效浓度50％（EC（50））值在0.63-10.0μ范围内克/毫升。由于缺乏细胞毒性，这些化合物具有高度选择性。抗病毒活性取决于吸附期间硫酸化岩藻聚糖的存在。在杀病毒测定中没有观察到对病毒粒子的直接灭活作用。在接近 EC50 的浓度下不存在抗凝血活性，证实抗病毒和抗凝血特性之间不存在相关性。 (c) 2006 Elsevier Ltd. 保留所有权利。
A sulfated fucan containing fraction (SmWE) was isolated from water extract of the brown seaweed Stoechospermum marginatum collected from the Arabian Sea. Anion exchange chromatography of the crude fraction results in the production of a sulfated fucan (F3) having a molecular mass of 40 kDa and specific rotation [alpha](D)(30) - 124 degrees (c 0.5, H(2)O). NMR spectroscopic studies and methylation analysis suggested that the polymer consists of a backbone of (1 -> 4)- and (1 -> 3)-linked-alpha-L-fucopyranosyl residues that are substituted at C-2 and C-3, and that fucosyl residues are sulfated mostly at C-2 and/or C-4. SmWE and F3 were selective inhibitors of herpes simplex virus type I (strain F, thymidine kinase-deficient strains field and B2006 and syncytial variants arising after selection with a natural carrageenan syn 13-8 and 14-1) and type 2 (strain MS) in Vero cells, with antiviral effective concentration 50% (EC(50)) values in the range 0.63-10.0 mu g/ml. The compounds were highly selective due to the lack of cytotoxicity. The antiviral activity was dependent on the presence of the sulfated fucans during the adsorption period. No direct inactivating effect on virions was observed in a virucidal assay. The absence of anticoagulant activity at concentrations near EC50 confirmed that there was no correlation between the antiviral and anticoagulant properties. (c) 2006 Elsevier Ltd. All rights reserved.