El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor


Room-temperature acid (pH 2) extraction of Dictyota dichotoma thalli yielded 2.2% of sulfated polysaccharides. Further extraction with the same solvent at 70 C was conducted sequentially for nine times, with a total yield of 7.2%. Fucose was the main monosaccharide only in the room-temperature extract (EAR) and in the first 70 C extract (EAH1). The remaining fractions showed increasing amounts of mannose (the main neutral monosaccharide), xylose and uronic acids. Fractionation by means of cetrimide precipitation and redissolution in increasing sodium chloride solutions has allowed obtaining several subfractions from each extract. The fractions redissolved at lower NaCl concentrations have large amounts of uronic acids and lesser sulfate contents, whereas those redissolved at higher NaCl concentrations are heavily sulfated and have low uronic acid contents. For the fucose-rich extracts (EAR and EAH1), fractionation leads to uronoxylomannofucan-rich and galactofucan-rich fractions. The remaining extracts gave rise to complex mixtures, with mannose and uronic acid-rich polysaccharides. Moderate inhibitory effect against herpes virus (HSV-1) and Coxsackie virus (CVB3) were found for the galactofucan-rich fractions. Most of the other fractions were inactive against both viruses, although some xylomannan-rich fractions were also active against HSV-1. © 2013 Elsevier Ltd. All rights reserved.


Documento: Artículo
Título:The system of fucoidans from the brown seaweed Dictyota dichotoma: Chemical analysis and antiviral activity
Autor:Rabanal, M.; Ponce, N.M.A.; Navarro, D.A.; Gómez, R.M.; Stortz, C.A.
Filiación:Departamento de Química Orgánica-CIHIDECAR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Instituto de Biotecnología y Biología Molecular, Facultad de Ciencias Exactas, Universidad Nacional de la Plata, Calle 49 y 115, 1900 La Plata, Argentina
Idioma: Inglés
Palabras clave:Antiviral; Brown seaweeds; Dictyota dichotoma; Fucoidans; Galactofucans; Antiviral; Brown seaweed; Dichotoma; Fucoidans; Galactofucans; Extraction; Glucose; Polysaccharides; Seaweed; Sodium chloride; Viruses; Carboxylic acids; Coxsackievirus; Dictyota dichotoma; Herpesviridae; Human herpesvirus 1
Página de inicio:804
Página de fin:811
Título revista:Carbohydrate Polymers
Título revista abreviado:Carbohydr Polym


  • Abdel-Fattah, A.F., Magdel-Din Hussein, M., Fouad, S.T., Carbohydrates of the brown seaweed Dictyota dichotoma (1978) Phytochemistry, 17, pp. 741-743
  • 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 (2006) Phytochemistry, 67 (22), pp. 2474-2482. , DOI 10.1016/j.phytochem.2006.05.024, PII S0031942206002937
  • Albersheim, P., Nevins, D.J., English, P.D., Karr, A., A method for the analysis of sugars in plant cell-wall polysaccharides by gas-liquid chromatography (1967) Carbohydrate Research, 5, pp. 340-345
  • Albuquerque, I.R.L., Queiroz, K.C.S., Alves, L.G., Santos, E.A., Leite, E.L., Rocha, H.A.O., Heterofucans from Dictyota menstrualis have anticoagulant activity (2004) Brazilian Journal of Medical and Biological Research, 37 (2), pp. 167-171
  • Ale, M.T., Mikkelsen, J.D., Meyer, A.S., Important determinants for fucoidan bioactivity: A critical review of structure-function relations and extraction methods for fucose-containing sulfated polysaccharides from brown seaweeds (2011) Marine Drugs, 9, pp. 2106-2130
  • Athukorala, Y., Ahn, G.N., Jee, Y.J., Kim, G.Y., Kim, S.H., Ha, J.H., Antiproliferative activity of sulfated polysaccharide isolated from an enzymatic digest of Ecklonia cava on the U-937 cell line (2009) Journal of Applied Phycology, 21, pp. 307-314
  • Athukorala, Y., Jung, W.-K., Vasanthan, T., Jeon, Y.-J., An anticoagulative polysaccharide from an enzymatic hydrolysate of Ecklonia cava (2006) Carbohydrate Polymers, 66 (2), pp. 184-191. , DOI 10.1016/j.carbpol.2006.03.002, PII S0144861706001196
  • Ayrad, S.-E.N., Makki, M.S., Al-Kayal, N.S., Basaif, S.A., El-Foty, K.O., Asiri, A.M., Cytotoxic and protective DNA damage of three new diterprenoids from the brown alga Dictyota dichotoma (2011) European Journal of Medicinal Chemistry, 46, pp. 175-182
  • Bandyopadhyay, S.S., Navid, M.H., Ghosh, T., Schnitzler, P., Ray, B., Structural features and in vitro antiviral activities of sulfated polysaccharides from Sphacelaria indica (2011) Phytochemistry, 72, pp. 276-283
  • Beress, A., Wassermann, O., Bruhn, T., Beress, L., Kraiselburd, E.N., Gonzalez, L.V., De Motta, G.E., Chavez, P.I., A new procedure for the isolation of anti-HIV compounds (polysaccharides and polyphenols) from the marine alga Fucus vesiculosus (1993) Journal of Natural Products (Lloydia), 56 (4), pp. 478-488
  • Bilan, M.I., Grachev, A.A., Shashkov, A.S., Nifantiev, N.E., Usov, A.I., Structure of a fucoidan from the brown seaweed Fucus serratus (2006) Carbohydrate Research, 341 (2), pp. 238-245. , DOI 10.1016/j.carres.2005.11.009, PII S0008621505005197
  • Bilan, M.I., Grachev, A.A., Ustuzhanina, N.E., Shashkov, A.S., Nifantiev, N.E., Usov, A.I., Structure of a fucoidan from the brown seaweed Fucus evanescens C.Ag (2002) Carbohydrate Research, 337 (8), pp. 719-730. , DOI 10.1016/S0008-6215(02)00053-8, PII S0008621502000538
  • Bilan, M.I., Grachev, A.A., Ustuzhanina, N.E., Shashkov, A.S., Nifantiev, N.E., Usov, A.I., A highly regular fraction of a fucoidan from the brown seaweed Fucus distichus (2004) Carbohydrate Research, 339 (3), pp. 511-517. , DOI 10.1016/j.carres.2003.10.028
  • Bilan, M.I., Grachev, A.A., Shashkov, A.S., Kelly, M., Sanderson, C.J., Nifantiev, N.E., Further studies on the composition and structure of a fucoidan preparation from the brown alga Saccharina latissima (2010) Carbohydrate Research, 345, pp. 2038-2047
  • Bilan, M.I., Vinogradova, E.V., Tsvetkova, E.A., Grachev, A.A., Shashkov, A.S., Nifantiev, N.E., A sulfated glucuronofucan containing both fucofuranose and fucopyranose residues from the brown alga Chordaria flagelliformis (2008) Carbohydrate Research, 343, pp. 2605-2612
  • Blondin, C., Fischer, E., Boisson-Vidal, C., Kazatchkine, M.D., Jozefonvicz, J., Inhibition of complement activation by natural sulfated polysaccharides (fucans) from brown seaweed (1994) Molecular Immunology, 31 (4), pp. 247-253. , DOI 10.1016/0161-5890(94)90121-X
  • Cardoso, M.A., Noseda, M.D., Fujii, M.T., Zibetti, R.G.M., Duarte, M.E.R., Sulfated xylomannans isolated from red seaweeds Chondrophycus papillosus and C. Flagelliferus (Ceramiales) from Brazil (2007) Carbohydrate Research, 342 (18), pp. 2766-2775. , DOI 10.1016/j.carres.2007.08.024, PII S0008621507003977
  • Chandia, N.P., Matsuhiro, B., Characterization of a fucoidan from Lessonia vadosa (Phaeophyta) and its anticoagulant and elicitor properties (2008) International Journal of Biological Macromolecules, 42 (3), pp. 235-240. , DOI 10.1016/j.ijbiomac.2007.10.023, PII S0141813007002735
  • Chevolot, L., Foucault, A., Chaubet, F., Kervarec, N., Sinquin, C., Fisher, A.-M., Boisson-Vidal, C., Further data on the structure of brown seaweed fucans: Relationships with anticoagulant activity (1999) Carbohydrate Research, 319 (1-4), pp. 154-165. , DOI 10.1016/S0008-6215(99)00127-5, PII S0008621599001275
  • Chevolot, L., Mulloy, B., Ratiskol, J., Foucault, A., Colliec-Jouault, S., A disaccharide repeat unit is the major structure in fucoidans from two species of brown algae (2001) Carbohydrate Research, 330 (4), pp. 529-535. , DOI 10.1016/S0008-6215(00)00314-1, PII S0008621500003141
  • Croci, D.O., Cumashi, A., Ushakova, N.A., Preobrazhenskaya, M.E., Piccoli, A., Totani, L., Fucans, but not fucomannoglucuronans, determine the biological activities of sulfated polysaccharides from Laminaria saccharina brown seaweed (2011) PLoS ONE, 6, p. 17283
  • Damonte, E.B., Matulewicz, M.C., Cerezo, A.S., Sulfated seaweed polysaccharides as antiviral agents (2004) Current Medicinal Chemistry, 11 (18), pp. 2399-2419
  • Denizot, F., Lang, R., Rapid colorimetric assay for cell growth and survival - Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability (1986) Journal of Immunological Methods, 89 (2), pp. 271-277. , DOI 10.1016/0022-1759(86)90368-6
  • Dodgson, K.S., Price, R.G., A note on the determination of the ester sulphate content of sulphated polysaccharides (1962) Biochemical Journal, 84, pp. 106-110
  • Duarte, M.E.R., Cardoso, M.A., Noseda, M.D., Cerezo, A.S., Structural studies on fucoidans from the brown seaweed Sargassum stenophyllum (2001) Carbohydrate Research, 333 (4), pp. 281-293. , DOI 10.1016/S0008-6215(01)00149-5, PII S0008621501001495
  • 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. 350-356
  • Feldman, S.C., Reynaldi, S., Stortz, C.A., Cerezo, A.S., Damonte, E.B., Antiviral properties of fucoidan fractions from Leathesia difformis (1999) Phytomedicine, 6, pp. 335-340
  • Filisetti-Cozzi, T.M.C.C., Carpita, N.C., Measurement of uronic acids without interference from neutral sugars (1991) Analytical Biochemistry, 197, pp. 157-162
  • Foley, S.A., Mulloy, B., Tuohy, M.G., An unfractionated fucoidan from Ascophyllum nodosum: Extraction, characterization and apoptotic effects in vitro (2011) Journal of Natural Products, 74, pp. 1851-1861
  • Harden, E.A., Falshaw, R., Carnachan, S.M., Kern, E.R., Prichard, M.N., Virucidal activity of polysaccharide extracts from four algal species against herpes simplex virus (2009) Antiviral Research, 83, pp. 282-289
  • Hayashi, K., Nakano, T., Hashimoto, M., Kanekiyo, K., Hayashi, T., Defensive effects of a fucoidan from brown alga Undaria pinnatifida against herpes simplex virus infection (2008) International Immunopharmacology, 8 (1), pp. 109-116. , DOI 10.1016/j.intimp.2007.10.017, PII S1567576907003372
  • Hidari, K.I.P.J., Takahashi, N., Arihara, M., Nagaoka, M., Morita, K., Suzuki, T., Structure and anti-dengue virus activity of sulfated polysaccharide from a marine alga (2008) Biochemical and Biophysical Research Communications, 376, pp. 91-95
  • Kantachumpoo, A., Chirapart, A., Components and antimicrobial activity of polysaccharides extracted from thai brown seaweeds (2010) Kasetsart Journal - Natural Science, 44, pp. 220-233
  • Karmakar, P., Ghosh, T., Sinha, S., Saha, S., Mandal, P., Ghosal, P.K., Polysaccharides from the brown seaweed Padina tetrastromatica: Characterization of a sulfated fucan (2009) Carbohydrate Polymers, 78, pp. 416-421
  • Kolender, A.A., Matulewicz, M.C., Cerezo, A.S., Structural analysis of antiviral sulfated α-d-(1→3)-linked mannans (1995) Carbohydrate Research, 273, pp. 179-185
  • Kolender, A.A., Pujol, C.A., Damonte, E.B., Matulewicz, M.C., Cerezo, A.S., The system of sulfated α-(1 → 3)-linked D-mannans from the red seaweed Nothogenia fastigiata: Structures, antiherpetic and anticoagulant properties (1997) Carbohydrate Research, 304 (1), pp. 53-60. , DOI 10.1016/S0008-6215(97)00201-2, PII S0008621597002012
  • Lee, J.-B., Takeshita, A., Hayashi, K., Hayashi, T., Structures and antiviral activities of polysaccharides from Sargassum trichophyllum (2011) Carbohydrate Polymers, 86, pp. 995-999
  • Leite, E.L., Medeiros, M.G.L., Rocha, H.A.O., Farias, G.G.M., Da Silva, L.F., Chavante, S.F., De Abreu, L.D., Nader, H.B., Structure and pharmacological activities of a sulfated xylofucoglucuronan from the alga Spatoglossum schroederi (1998) Plant Science, 132 (2), pp. 215-228. , DOI 10.1016/S0168-9452(98)00012-0, PII S0168945298000120
  • Li, B., Wei, X.-J., Sun, J.-L., Xu, S.-Y., Structural investigation of a fucoidan containing a fucose-free core from the brown seaweed, Hizikia fusiforme (2006) Carbohydrate Research, 341, pp. 1135-1146
  • Lowry, O.H., Rosebrough, N.J., Farr, A.L., Randall, R., Protein measurement with the Folin phenol method (1951) Journal of Biological Chemistry, 193, pp. 265-275
  • Magdel-Din Hussein, M., Fouad, S.T., Abdel-Fattah, A.F., Structural features of a sulphated, fucose-cointaining polysaccharide from the brown seaweed Dictyota dichotoma (1979) Carbohydrate Research, 72, pp. 177-181
  • Mahony, M.C., Clark, G.F., Oehninger, S., Acosta, A.A., Hodgen, G.D., Fucoidin binding activity and its localization on human spermatozoa (1993) Contraception, 48 (3), pp. 277-289. , DOI 10.1016/0010-7824(93)90146-X
  • Mahony, M.C., Oehninger, S., Clark, G.F., Acosta, A.A., Hodgen, G.D., Fucoidin inhibits the zona pellucida-induced acrosome reaction in human spermatozoa (1991) Contraception, 44, pp. 657-665
  • Mandal, P., Pujol, C.A., Carlucci, M.J., Chattopadhyay, K., Damonte, E.B., Ray, B., Anti-herpetic activity of a sulfated xylomannan from Scinaia hatei (2008) Phytochemistry, 69, pp. 2193-2199
  • Matulewicz, M.C., Cerezo, A.S., Water-soluble sulfated polysaccharides from the red seaweed chaetangium fastigiatum. Analysis of the system and the structures of the alpha -d-(1 yields 3)-linked mannans (1987) Carbohydrate Polymers, 7 (2), pp. 121-132. , DOI 10.1016/0144-8617(87)90054-3
  • Mauray, S., Sternberg, C., Theveniaux, J., Millet, J., Sinquin, C., Tapon-Bretaudiere, J., Venous antithrombotic and anticoagulant activities of a fucoidan fraction (1995) Thrombosis and Haemostasis, 74, pp. 1280-1285
  • McClure, M.O., Whitby, D., Patience, C., Gooderham, N.J., Bradshaw, A., Cheingsong-Popov, R., Dextrin sulphate and fucoidan are potent inhibitors of HIV infection in vitro (1991) Antiviral Chemistry and Chemotherapy, 2, pp. 149-156
  • Nardella, A., Chaubet, F., Boisson-Vidal, C., Blondin, C., Durand, P., Jozefonvicz, J., Anticoagulant low molecular weight fucans produced by radical process and ion exchange chromatography of high molecular weight fucans extracted from the brown seaweed Ascophyllum nodosum (1996) Carbohydrate Research, 289, pp. 201-208. , DOI 10.1016/0008-6215(96)00110-3
  • Nishino, T., Nagumo, T., Anticoagulant and antithrombin activities of oversulfated fucans (1992) Carbohydrate Research, 229, pp. 355-362
  • Nishino, T., Kiyohara, H., Yamada, H., Nagumo, T., An anticoagulant fucoidan from the brown seaweed Ecklonia kurome (1991) Phytochemistry, 30, pp. 535-539
  • Nishino, T., Nagumo, T., Kiyohara, H., Yamada, H., Structural characterization of a new anticoagulant fucan sulfate from the brown seaweed Ecklonia kurome (1991) Carbohydrate Research, 211, pp. 77-90
  • Painter, T.J., Algal polysaccharides (1983) The Polysaccharides, 2 VOL., pp. 195-285. , G.O. Aspinall, Academic Press London
  • Park, J.T., Johnson, M.J., A submicrodetermination of glucose (1949) Journal of Biological Chemistry, 181, pp. 149-151
  • Pereira, M.S., Mulloy, B., Mourão, P.A.S., Structure and anticoagulant acitivity of sulphated fucans (1999) Journal of Biological Chemistry, 274, pp. 7656-7667
  • Pérez Recalde, M., Noseda, M.D., Pujol, C.A., Carlucci, M.J., Matulewicz, M.C., Sulfated mannans from the red seaweed Nemalion helminthoides of the South Atlantic (2009) Phytochemistry, 70, pp. 1062-1068
  • 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 (2), pp. 153-165. , DOI 10.1016/S0008-6215(02)00403-2, PII S0008621502004032
  • Queiroz, K.C.S., Medeiros, V.P., Queiroz, L.S., Abreu, L.R.D., Rocha, H.A.O., Ferreira, C.V., Juca, M.B., Leite, E.L., Inhibition of reverse transcriptase activity of HIV by polysaccharides of brown algae (2008) Biomedicine and Pharmacotherapy, 62 (5), pp. 303-307. , DOI 10.1016/j.biopha.2008.03.006, PII S0753332208000656
  • Ravikumar, S., Alí, M.S., Beula, J.M., Mosquito larvicidal efficacy of seaweed extracts against dengue vector of Aedes aegypti (2011) Asian Pacific Journal of Tropical Biomedicine, 1 (2), pp. 143-S146
  • Rocha De Souza, M.C., Marques, C.T., Guerra Dore, C.M., Ferreira Da Silva, F.R., Oliveira Rocha, H.A., Leite, E.L., Antioxidant activities of sulfated polysaccharides from brown and red seaweeds (2007) Journal of Applied Phycology, 19 (2), pp. 153-160. , DOI 10.1007/s10811-006-9121-z
  • Ruperez, P., Ahrazem, O., Leal, J.A., Potential antioxidant capacity of sulfated polysaccharides from the edible marine brown seaweed Fucus vesiculosus (2002) Journal of Agricultural and Food Chemistry, 50 (4), pp. 840-845. , DOI 10.1021/jf010908o
  • Sakai, T., Kimura, H., Kojima, K., Shimanaka, K., Ikai, K., Kato, I., Marine bacterial sulfated fucoglucuronomannan (SFGM) lyase digests brown algal SFGM into trisaccharides (2003) Marine Biotechnology, 5 (1), pp. 70-78. , DOI 10.1007/s10126-002-0056-3
  • Tabarsa, M., Rezaei, M., Ramezanpour, Z., Waaland, J.R., Rabiei, R., Fatty acids, amino acids, mineral contents, and proximate composition of some brown seaweeds (2012) Journal of Phycology, 48, pp. 285-292
  • Trinchero, J., Ponce, N.M.A., Córdoba, O.L., Flores, M.L., Pampuro, S., Stortz, C.A., Antiretroviral activity of fucoidans extracted from the brown seaweed Adenocystis utricularis (2009) Phytotherapy Research, 23, pp. 707-712
  • Tronholm, A., Steen, F., Tyberghein, L., Leliaert, F., Verbruggen, H., Ribera Siguan, M.A., Species delimitation, taxonomy, and biogeography of Dictyota in Europe (Dictyotales, Phaeophyceae) (2010) Journal of Phycology, 46, pp. 1301-1321
  • Usov, A.I., Adamyants, K.S., Yarotskii, S.V., Anoshina, A.A., Polysaccharides of algae 16. Study of the structure of the sulfated mannan from the red alga Nemalion vermiculare sur (1975) Zhurnal Obshchei Khimii, 45, pp. 916-921
  • Usov, A.I., Dobkina, I.M., Polysaccharides of algae 38. Polysaccharide composition of the red alga Liagora sp and structure of the sulfated xylomannan (1988) Bioorganischeskaya Khimiya, 14, pp. 642-651
  • Venkateswaran, P.S., Millman, I., Blumberg, B.S., Interaction of fucoidan from Pelvetia fastigiata with surface antigens of hepatitis B and woodchuck hepatitis virus (1989) Planta Medica, 55 (3), pp. 265-270. , DOI 10.1055/s-2006-962000
  • Wang, H., Ooi, E.V., Ang, Jr.P.O., Antiviral activities of extracts from Hong Kong seaweeds (2008) Journal of Zhejiang University Science B, 9, pp. 969-976
  • Wang, J., Zhang, Q., Zhang, Z., Li, Z., Antioxidant activity of sulfated polysaccharide fractions extracted from Laminaria japonica (2008) International Journal of Biological Macromolecules, 42, pp. 127-132
  • Wang, J., Zhang, Q., Zhang, Z., Song, H., Li, Z., Potential antioxidant and anticoagulant capacity of low molecular weight fucoidan fractions extracted from Laminaria japonica (2010) International Journal of Biological Macromolecules, 46, pp. 6-12
  • Wijesekara, I., Pangestuti, R., Kim, S.-K., Biological activities and potential health benefits of sulfated polysaccharides derived from marine algae (2011) Carbohydrate Polymers, 84, pp. 14-21
  • Yang, C., Chung, D., Shin, I.-S., Lee, H., Kim, J., Lee, Y., Effects of molecular weight and hydrolysis conditions on anticancer activity of fucoidans from sporophyll of Undaria pinnatifida (2008) International Journal of Biological Macromolecules, 43, pp. 433-437
  • Zhuang, C., Itoh, H., Mizuno, T., Ito, H., Antitumor active fucoidan from the brown seaweed, umitoranoo (Sargassum thunbergii) (1995) Bioscience, Biotechnology and Biochemistry, 59, pp. 563-567


---------- APA ----------
Rabanal, M., Ponce, N.M.A., Navarro, D.A., Gómez, R.M. & Stortz, C.A. (2014) . The system of fucoidans from the brown seaweed Dictyota dichotoma: Chemical analysis and antiviral activity. Carbohydrate Polymers, 101(1), 804-811.
---------- CHICAGO ----------
Rabanal, M., Ponce, N.M.A., Navarro, D.A., Gómez, R.M., Stortz, C.A. "The system of fucoidans from the brown seaweed Dictyota dichotoma: Chemical analysis and antiviral activity" . Carbohydrate Polymers 101, no. 1 (2014) : 804-811.
---------- MLA ----------
Rabanal, M., Ponce, N.M.A., Navarro, D.A., Gómez, R.M., Stortz, C.A. "The system of fucoidans from the brown seaweed Dictyota dichotoma: Chemical analysis and antiviral activity" . Carbohydrate Polymers, vol. 101, no. 1, 2014, pp. 804-811.
---------- VANCOUVER ----------
Rabanal, M., Ponce, N.M.A., Navarro, D.A., Gómez, R.M., Stortz, C.A. The system of fucoidans from the brown seaweed Dictyota dichotoma: Chemical analysis and antiviral activity. Carbohydr Polym. 2014;101(1):804-811.