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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.


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
Página de inicio:2474
Página de fin:2482
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
CAS:fucoidin, 9072-19-9; sulfate, 14808-79-8; thymidine kinase, 9002-06-6, 9086-73-1; Anticoagulants; Antiviral Agents; Polysaccharides; Sulfates; Thymidine Kinase,; fucoidan, 9072-19-9


  • Ahmed, A., Labavitch, J.M., A simplified method for accurate determination of cell wall uronide content (1977) Journal of Food Biochemistry, 1, pp. 361-365
  • Bacon, T.H., Levin, M.J., Leary, J.L., Sarisky, R.T., Sutton, D., Herpes simplex virus resistance to acyclovir and penciclovir after two decades of antiviral therapy (2003) Clinical Microbiology Reviews, 16, pp. 114-128
  • Bilan, M.I., Grachev, A.A., Ustuzhanina, N.E., Shaskov, A.S., Nifantiev, N.E., Usov, A.I., A highly regular fraction of a fucoidan from the brown seaweed Fucus distichus L (2004) Carbohydrate Research, 339, pp. 511-517
  • Bisgrove, S.R., Kropf, D.L., Cell wall deposition during morphogenesis in fucoid algae (2001) Planta, 212, pp. 648-658
  • Blakeney, A.B., Stone, B.A., Methylation of carbohydrates with lithium methylsulphinyl carbanion (1985) Carbohydrate Research, 140, pp. 319-324
  • Blakeney, A.B., Harris, P., Henry, R.J., Bruce, A.B., A simple rapid preparation of alditol acetates for monosaccharide analysis (1983) Carbohydrate Research, 113, pp. 291-299
  • Boisson-Vidal, C., Haroun, F., Ellouali, M., Blondin, C., Fischer, A.M., De Agostini, A., Jozefonvicz, J., Biological activities of polysaccharide from marine algae (1995) Drugs of the Future, 20, pp. 1237-1249
  • Brady, R.C., Bernstein, D.I., Treatment of herpes simplex virus infections (2004) Antiviral Research, 61, pp. 73-81
  • Carlucci, M.J., Scolaro, L.A., Damonte, E.B., Herpes somplex virus type 1 variants arising after selection with an antiviral carrageenan: lack of correlation between drug susceptibility and syn phenotype (2002) Journal of Medical Virology, 68, pp. 92-98
  • Craigie, J.S., Wen, Z.C., van der Meer, J.P., Interspecific, intraspecific and nutritionally-determined variations in the composition of agars from Gracilaria spp (1984) Botanica Marina, XXVII, pp. 55-61
  • Duarte, M.E.R., Cauduro, J.P., Noseda, D.G., Noseda, M.D., Goncalves, A.G., Pujol, C.A., Damonte, E.B., Cerezo, A.S., The structure of the agaran sulfate from Acanthophora spicifera (Rhodomelaceae, Ceramiales) and its antiviral activity. Relation between structure and antiviral activity in agarans (2004) Carbohydrate Research, 339, pp. 335-347
  • Dubois, M., Gilles, K.A., Hamilton, J.K., Rebers, P.A., Smith, F., Colorimetric method for determination of sugars and related substances (1956) Analytical Chemistry, 28, pp. 350-366
  • Eizuru, Y., Development of new antivirals for herpesviruses (2003) Antiviral Chemistry and Chemotherapy, 14, pp. 299-308
  • Franz, G., Pauper, D., Alban, S., (2000) Bioactive Carbohydrate Polymers, pp. 47-58. , Paulsen B.S. (Ed), Kluwer Academic Publishers., Dordrecht
  • Ghosh, P., Adhikari, U., Ghosal, P., Pujol, C.A., Carlucci, M.J., Damonte, E.B., Ray, B., In vitro anti-herpetic activity of sulfated polysaccharide fractions from Caulerpa racemosa (2004) Phytochemistry, 65, pp. 3151-3157
  • Ghosh, P., Ghosal, P., Thakur, S., Lerouge, P., Loutelier-Bourhis, C., Driouich, A., Ray, B., Cell wall polysaccharides of Brassica campestris seed cake: isolation and structural features (2004) Carbohydrate Polymers, 57, pp. 7-13
  • Ghosh, P., Ghosal, P., Thakur, S., Lerouge, P., Loutelier-Bourhis, C., Driouich, A., Ray, B., Non-starch polysaccharides from Sesamum indicum: Isolation and structural features (2005) Food Chemistry, 90, pp. 719-726
  • Gunay, N.S., Linhardt, R.J., Heparinoids: structure, biological activities and therapeutic applications (1999) Planta Medica, 65, pp. 301-306
  • Iqbal, M., Flick-Smith, H., McCauley, J.W., Interactions of bovine viral diarrhoea virus glycoprotein E(rns) with cell surface glycosaminoglycans (2000) Journal of General Virology, 81, pp. 451-459
  • Kariya, Y., Mulloy, B., Imai, K., Tominaga, A., Kaneko, T., Asari, A., Suzuki, K., Ishii, T., Isolation and partial characterisation of fucan sulfates from the body wall of sea cucumber Stichopus japonicus and their ability to inhibit osteoclastogenesis (2004) Carbohydrate Research, 339, pp. 1339-1346
  • Mazumder, S., Ghosal, P.K., Pujol, C.A., Carlucci, M.J., Damonte, E.B., Ray, B., Isolation, chemical investigation and antiviral activity of polysaccharides from Gracilaria corticata (Gracilariaceae, Rhodophyta) (2002) International Journal of Biological Macromolecules, 31, pp. 87-95
  • McClure, M.O., Whitby, D., Patience, C., Gooderham, N.J., Bradshaw, A., Cheingsong-Popov, R., Weber, J.N., Weiss, R.A., Dextrin sulphate and fucoidan are potent inhibitors of HIV infection in vitro (1992) Antiviral Chemistry and Chemotherapy, 2, pp. 149-156
  • Mosmann, T., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays (1983) Journal of Immunological Methods, 65, pp. 55-63
  • Mulloy, B., Mourao, P.A.S., Gray, E., Structure/function studies of anticoagulant sulfated polysaccharides using NMR (2000) Journal of Biotechnology, 77, pp. 123-135
  • Murao, P.A.S., Pereira, M.S., Pavao, M.S.G., Mulloy, B., Tollefsen, D.M., Mowinckel, M.-C., Abildgaard, U., Structure and anticoagulant activity of fucosylated chondroitin sulfate from Echinoderm (1996) Journal of Biological Chemistry, 271, pp. 23973-23984
  • Nagasawa, K., Inoue, Y., Kamara, T., Solvolyticdesulfation of glycosaminoglycan sulfates with dimethyl sulfoxide containing water or methanol (1977) Carbohydrate Research, 58, pp. 47-55
  • Patankar, M.S., Oehninger, S., Barnett, T., Williams, R.L., Clark, G.F., A revised structure for fucoidan may explain some of its biological activities (1993) Journal of Biological Chemistry, 268, pp. 21770-21776
  • Percival, E., Wold, J.K., The acid from green seaweed Ulva lactuca. Part II. The site of ester sulphate (1963) Journal of Chemical Society, pp. 5459-5468
  • Pereira, M.S., Mulloy, B., Mourao, P.A.S., Structure and anticoagulant activity of sulfated fucans (1999) Journal of Biological Chemistry, 274, pp. 7656-7667
  • Ponce, N.M.A., Pujol, C.A., Damonte, E.B., Flores, M.L., Stortz, C.A., Fucoidans from the brown seaweed Adenocystis utricularis: extraction methods, antiviral activity and structural studies (2003) Carbohydrate Research, 338, pp. 153-165
  • Ray, B., Lahaye, M., Cell-wall polysaccharides from the marine green algae Ulva rigida (Ulvales, Chlorophyta). Chemical structure of ulvan (1995) Carbohydrate Research, 274, pp. 313-318
  • Rochas, C., Lahaye, M., Yaphe, W., Sulfate content of carrageenan and agar determined by infrared spectroscopy (1986) Botanica Marina, 29, pp. 335-340
  • Stevenson, T.T., Furneaux, R.H., Chemical methods for the analysis of sulphated galactans from red algae (1991) Carbohydrate Research, 210, pp. 277-298
  • Vilela-Silva, A.-C.E.S., Castro, M.O., Valente, A.-P., Bierman, C.H., Mourao, P.A.S., Sulfated fucans from the egg jellies of the closely related sea urchins Strongylocentrotus and pallidus ensure species specific fertilization (2002) Journal of Biological Chemistry, pp. 379-387
  • Whitley, R.J., Gnann, J.W., The epidemiology and clinical manifestations of herpes simplex virus infections (1993) The Human Herpesviruses, pp. 69-105. , Roizman B., Whitley R.J., and Lopez C. (Eds), Raven Press, New York
  • Witvrouw, M., De Clercq, E., Sulfated polysaccharides extracted from sea algae as potential antiviral drugs (1997) General Pharmacology, 29, pp. 497-511


---------- 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.
---------- 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.
---------- 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.
---------- 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.