Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum.
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, H2O). 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 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% (EC50) values in the range 0.63-10.0 microg/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.
Adhikari
Utpal
U
Natural Products Laboratory, Department of Chemistry, The University of Burdwan, Golapbag, Burdwan, West Bengal 713 104, India.
Mateu
Cecilia G
CG
Chattopadhyay
Kausik
K
Pujol
Carlos A
CA
Damonte
Elsa B
EB
Ray
Bimalendu
B
D000925:Anticoagulants / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology*; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008970:Molecular Weight; D000459:Phaeophyceae / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D018139:Simplexvirus / Q000187:drug effects; D013431:Sulfates / Q000737:chemistry*; D013937:Thymidine Kinase / Q000378:metabolism
D000925:Anticoagulants; D000998:Antiviral Agents; D011134:Polysaccharides; D013431:Sulfates; C007789:fucoidan; D013937:Thymidine Kinase