Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum

• Published in: Phytochemistry (Oxford) 2006-11, Vol.67 (22), p.2474-2482
• Main Authors: Adhikari, Utpal, Mateu, Cecilia G., Chattopadhyay, Kausik, Pujol, Carlos A., Damonte, Elsa B., Ray, Bimalendu
• Format: Article
• Language: English
• Subjects: algae and seaweeds; Anticoagulant activity; anticoagulants; Anticoagulants - chemistry; Anticoagulants - pharmacology; Antiviral agent; Antiviral Agents - chemistry; Antiviral Agents - pharmacology; antiviral properties; Biological and medical sciences; carbohydrate structure; Chemical constitution; Dictyotales; fucoidan; Fundamental and applied biological sciences. Psychology; General pharmacology; Herpes simplex virus; Herpes simplex virus 1; HIV-1 - drug effects; Human herpesvirus 1; Human herpesvirus 2; Humans; Magnetic Resonance Spectroscopy; Marine; Medical sciences; Methylation; Methylation analysis; Molecular mass; Molecular Weight; NMR spectroscopy; Phaeophyceae - chemistry; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant physiology and development; Polysaccharides - chemistry; Polysaccharides - isolation & purification; Polysaccharides - pharmacology; Simplexvirus - drug effects; spectral analysis; Stoechospermum marginatum; Sulfated fucan; Sulfates - chemistry; Thymidine Kinase - metabolism
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2006.05.024

Isolation, structural features and antiherpetic activity of a purified sulfated fucan from Stoechospermum marginatum. The following are the major structural features of the fucan sulfate having antiviral activity. 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 [ α ] D 30 – 124° ( c 0.5, H 2O). NMR spectroscopic studies and methylation analysis suggested that the polymer consists of a backbone of (1 → 4)- and (1 → 3)-linked-α- 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 1 (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 μg/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 EC 50 confirmed that there was no correlation between the antiviral and anticoagulant properties.