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Abstract:

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]D30 - 124° (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-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% (EC50) 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 EC50 confirmed that there was no correlation between the antiviral and anticoagulant properties. © 2006 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum
Autor:Adhikari, U.; Mateu, C.G.; Chattopadhyay, K.; Pujol, C.A.; Damonte, E.B.; Ray, B.
Filiación:Natural Products Laboratory, Department of Chemistry, The University of Burdwan, Golapbag, Burdwan, West Bengal 713 104, India
Laboratorio de Virología, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales UBA, Ciudad Univ.-Pabellon 2 Piso 4, 1428 Buenos Aires, Argentina
Palabras clave:Anticoagulant activity; Antiviral agent; Herpes simplex virus; Methylation analysis; Molecular mass; NMR spectroscopy; Stoechospermum marginatum; Sulfated fucan; anticoagulant agent; antivirus agent; fucoidin; polysaccharide; sulfate; thymidine kinase; article; brown alga; chemistry; drug effect; Herpes simplex virus; human; Human immunodeficiency virus 1; isolation and purification; metabolism; methylation; molecular weight; nuclear magnetic resonance spectroscopy; Simplexvirus; Algae, Brown; Anticoagulants; Antiviral Agents; HIV-1; Humans; Magnetic Resonance Spectroscopy; Methylation; Molecular Weight; Phaeophyta; Polysaccharides; Simplexvirus; Sulfates; Thymidine Kinase; Human herpesvirus 1; Simplexvirus; Stoechospermum marginatum
Año:2006
Volumen:67
Número:22
Página de inicio:2474
Página de fin:2482
DOI: http://dx.doi.org/10.1016/j.phytochem.2006.05.024
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
ISSN:00319422
CODEN:PYTCA
CAS:fucoidin, 9072-19-9; sulfate, 14808-79-8; thymidine kinase, 9002-06-6, 9086-73-1; Anticoagulants; Antiviral Agents; Polysaccharides; Sulfates; Thymidine Kinase, 2.7.1.21; fucoidan, 9072-19-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v67_n22_p2474_Adhikari

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Citas:

---------- APA ----------
Adhikari, U., Mateu, C.G., Chattopadhyay, K., Pujol, C.A., Damonte, E.B. & Ray, B. (2006) . Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum. Phytochemistry, 67(22), 2474-2482.
http://dx.doi.org/10.1016/j.phytochem.2006.05.024
---------- CHICAGO ----------
Adhikari, U., Mateu, C.G., Chattopadhyay, K., Pujol, C.A., Damonte, E.B., Ray, B. "Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum" . Phytochemistry 67, no. 22 (2006) : 2474-2482.
http://dx.doi.org/10.1016/j.phytochem.2006.05.024
---------- MLA ----------
Adhikari, U., Mateu, C.G., Chattopadhyay, K., Pujol, C.A., Damonte, E.B., Ray, B. "Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum" . Phytochemistry, vol. 67, no. 22, 2006, pp. 2474-2482.
http://dx.doi.org/10.1016/j.phytochem.2006.05.024
---------- VANCOUVER ----------
Adhikari, U., Mateu, C.G., Chattopadhyay, K., Pujol, C.A., Damonte, E.B., Ray, B. Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum. Phytochemistry. 2006;67(22):2474-2482.
http://dx.doi.org/10.1016/j.phytochem.2006.05.024