Sulfated xylogalactofucans from Spatoglossum asperum: Production, structural features and antiviral activity

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2024-10-04 DOI:10.1016/j.carres.2024.109286

Shuvam Mukherjee , Mathias E. Chemen , Saikat Pal , Luana E. Piccini , Subrata Jana , Elsa B. Damonte , Bimalendu Ray , Cybele C. Garcia , Sayani Ray

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Abstract

In cultured cells, herpes simplex virus (HSV) infectivity is successfully inhibited by sulfated polysaccharides. Herein, we utilized an amalgamated extraction-sulfation procedure to produce two xylogalactofucan sulfates (S203 and S204) from Spatoglossum asperum using ClSO₃H.Pyr/DMF and SO₃.Pyr/DMF reagents, respectively. Among these xylogalactofucans, the 17 ± 12 kDa polymer (S203) with 14 % sulfate exhibited activity on several HSV variants, including an acyclovir-resistant HSV-1 strain. This is the first report of the anti-HSV activity of a sulfated xylogalactofucan of S. asperum. The effective concentration 50 % (EC₅₀) value of S203 against HSV-1 strain F was 0.6 μg/mL with a selectivity index of 833. The backbone of this polymer (S203) is made up mostly of (1 → 4)-linked-α-l-Fucp units having sulfate groups typically at O–3 and sometimes at O–2 positions. Oligosaccharides containing Xyl, Gal and Fuc units confirms that they are an integral part of a single polymer, another novelty of this study.

The EC₅₀ values of the native xylogalactofucan (S202) and the SO₃.Pyr/DMF modified polymer (S204), containing 2 % and 6 % sulfates, were >100 and 3.3 μg/mL, respectively. Introduction of sulfate groups enhanced their capability to inhibit the infection of cells by HSV-1. These findings suggest feasibility of inhibiting HSV attachment to cells by blocking viral entry with polysaccharide having specific structure.

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来自 Spatoglossum asperum 的硫酸化木糖半乳聚糖：生产、结构特征和抗病毒活性

在培养细胞中，硫酸化多糖能成功抑制单纯疱疹病毒（HSV）的感染性。在此，我们利用混合萃取-硫酸化程序，分别使用 ClSO3H.Pyr/DMF 和 SO3.Pyr/DMF 试剂从 Spatoglossum asperum 中提取出两种木糖硫酸酯（S203 和 S204）。在这些木糖半乳聚糖中，硫酸盐含量为 14% 的 17 ± 12 kDa 聚合物（S203）对多种 HSV 变体（包括耐阿昔洛韦的 HSV-1 株）具有活性。这是首次报道天南星硫酸化木糖半乳聚糖的抗 HSV 活性。S203 对 HSV-1 株 F 的有效浓度 50 %（EC50）值为 0.6 μg/mL，选择性指数为 833。这种聚合物（S203）的骨架主要由(1 → 4)连接的-α-l-Fucp单元组成，其硫酸基团通常位于O-3位，有时也位于O-2位。原生木糖半乳聚糖（S202）和含有 2% 和 6% 硫酸盐的 SO3.Pyr/DMF 改性聚合物（S204）的 EC50 值分别为 100 和 3.3 μg/mL。硫酸盐基团的引入增强了它们抑制 HSV-1 感染细胞的能力。这些发现表明，利用具有特定结构的多糖阻断病毒进入细胞，从而抑制 HSV 附着是可行的。

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".