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Matsuhiro, B.; Conte, A.F.; Damonte, E.B.; Kolender, A.A.; Matulewicz, M.C.; Mejías, E.G.; Pujol, C.A.; Zúñiga, E.A. "Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)" (2005) Carbohydrate Research. 340(15):2392-2402
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Abstract:

Aqueous extraction of gametophytic Schizymenia binderi afforded a polysaccharide composed of galactose and sulfate groups in a molar ratio of 1.0:0.89 together with uronic acids (6.8 wt %) and minor amounts of other neutral sugars. Alkali-treatment of the polysaccharide afforded a polysaccharide devoid of 3,6-anhydrogalactose. 13C NMR spectroscopy of the desulfated alkali-treated polysaccharide showed a backbone structure of alternating 3-linked β-D-galactopyranosyl and 4-linked α- galactopyranosyl units that are predominantly of the D-configuration and partly of the L-configuration. Methylation, ethylation and NMR spectroscopic studies of the alkali-treated polysaccharide indicated that the sulfate groups are located mainly at positions O-2 of 3-linked β-D-galactopyranosyl residue and at position O-3 of 4-linked-α-galactopyranosyl residues, the latter is partially glycosylated at position O-2. The sulfated galactan from S. binderi exhibited highly selective antiviral activity against Herpes simplex virus types 1 and 2, with selectivity indices (ratio cytotoxicity/antiviral activity) >1000 for all assayed virus strains. This compound was shown to interfere with the initial adsorption of viruses to cells. © 2005 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)
Autor:Matsuhiro, B.; Conte, A.F.; Damonte, E.B.; Kolender, A.A.; Matulewicz, M.C.; Mejías, E.G.; Pujol, C.A.; Zúñiga, E.A.
Filiación:Departamento de Ciencias Químicas, Facultad de Química Y Biología, Universidad de Santiago de Chile, Casilla 40, Santiago 33, Chile
Laboratorio de Virología, Departamento de Química Biológica, Pabellón 2, 1428 Buenos Aires, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas Y Naturales, Pabellón 2, 1428 Buenos Aires, Argentina
Palabras clave:Natural antiviral; Rhodophyta; Schizymenia binderi; Sulfated galactan; Uronic acids; Cytology; Glucose; Polysaccharides; Strain; Sugar (sucrose); Toxicity; Viruses; Antiviral activity; Glycosylated; Sulfate groups; Virus adsorption; Seaweed; antivirus agent; galactan; galactose; polysaccharide; sugar; uronic acid; adsorption; alkalinity; antiviral activity; article; cytotoxicity; extraction; glycosylation; Herpes simplex virus 1; Herpes simplex virus 2; methylation; nonhuman; priority journal; proton nuclear magnetic resonance; red alga; structure analysis; sulfation; virus strain; Algae, Red; Alkylation; Animals; Antiviral Agents; Carbohydrate Conformation; Cell Survival; Cercopithecus aethiops; Galactans; Herpesvirus 1, Human; Herpesvirus 2, Human; Inhibitory Concentration 50; Nuclear Magnetic Resonance, Biomolecular; Sulfuric Acid Esters; Vero Cells; algae; Gigartinales; Rhodophyta; Schizymenia; Simplexvirus
Año:2005
Volumen:340
Número:15
Página de inicio:2392
Página de fin:2402
DOI: http://dx.doi.org/10.1016/j.carres.2005.08.004
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:galactan, 39300-87-3, 9037-55-2; galactose, 26566-61-0, 50855-33-9, 59-23-4; Antiviral Agents; Galactans; Sulfuric Acid Esters
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v340_n15_p2392_Matsuhiro

Referencias:

  • Whyte, J.N.C., Foreman, R.E., De Wreede, R.E., (1984) Hydrobiologia, 116-117, pp. 537-541
  • Bourgougnon, N., Lahaye, M., Chermann, J.-C., Kornprobst, J.-M., (1993) Bioorg. Med. Chem. Lett., 3, pp. 1141-1146
  • Bourgougnon, N., Lahaye, M., Quemener, B., Cormaci, M., Furnari, G., Kornprobst, J.-M., (1996) J. Appl. Phycol., 8, pp. 147-153
  • Deslandes, E., Zinoun, M., Potin, P., (1993) Nat. Prod. Lett., 2, pp. 209-213
  • Witvrouw, M., Desmyter, J., De Clercq, E., (1994) Antiviral Chem. Chemother., 5, pp. 345-359
  • Witvrouw, M., Pannecouque, C., De Clerk, E., (1997) Carbohydrates in Drug Design, pp. 157-207. , Z.J. Witczak K.A. Nieforth Marcel Dekker New York
  • Pujol, C.A., Errea, M.I., Matulewicz, M.C., Damonte, E.B., (1996) Phytother. Res., 10, pp. 410-413
  • Kolender, A.A., Pujol, C.A., Damonte, E.B., Matulewicz, M.C., Cerezo, A.S., (1997) Carbohydr. Res., 304, pp. 53-60
  • Carlucci, M.J., Scolaro, L.A., Errea, M.I., Matulewicz, M.C., Damonte, E.B., (1997) Planta Med., 63, pp. 429-432
  • Nakashima, H., Kido, Y., Kobayashi, N., Motoki, Y., Neushul, M., Yamamoto, N., (1987) J. Cancer Res. Clin. Oncol., 113, pp. 413-416
  • Nakashima, H., Kido, Y., Kobayashi, N., Motoki, Y., Neushul, M., Yamamoto, N., (1987) Antimicrob. Agents Chemother., 31, pp. 1524-1528
  • Bourgougnon, N., Lahaye, M., Quemener, B., Chermann, J.-C., Rimbert, M., Cormaci, M., Furnari, G., Kornprobst, J.-M., (1996) J. Appl. Phycol., 8, pp. 155-161
  • Bourgougnon, N., Chermann, J.-C., Lahaye, M., Kornprobst, J.-M., (1996) Cell. Pharmacol., 3, pp. 104-108
  • Cáceres, P., Carlucci, M.J., Damonte, E.B., Matsuhiro, B., Zúñiga, E.A., (2000) Phytochemistry, 53, pp. 81-86
  • Carlucci, M.J., Pujol, C.A., Ciancia, M., Noseda, M.D., Matulewicz, M.C., Damonte, E.B., Cerezo, A.S., (1997) Int. J. Biol. Macromol., 20, pp. 97-105
  • Conley, R.T., (1966) Infrared Spectroscopy, , Allyn and Bacon Boston
  • Matsuhiro, B., (1996) Hydrobiologia, 326-327, pp. 481-489
  • Stancioff, D.J., Stanley, N.F., (1969) Proc. Int. Seaweed Symp., 6, pp. 595-609
  • Nakamoto, K., (1986) Infrared and Raman Spectra of Inorganic and Coordination Compounds, , 4th ed. Wiley-Interscience New York
  • Yaphe, W., Arsenault, G.P., (1965) Anal. Biochem., 13, pp. 143-148
  • Bowker, D.M., Turvey, J.R., (1968) J. Chem. Soc. C, pp. 983-988
  • Nunn, J.R., Parolis, H., Russell, I., (1973) Carbohydr. Res., 29, pp. 281-289
  • Court, G.J., Taylor, I.E.O., (1979) Phytochemistry, 18, pp. 411-414
  • Haslin, C., Lahaye, M., Pellegrini, M., (2000) Bot. Mar., 43, pp. 475-482
  • Usov, A.I., (1992) Food Hydrocoll., 6, pp. 9-23
  • Takano, R., Nose, Y., Hayashi, K., Hara, S., Hirase, S., (1994) Phytochemistry, 37, pp. 1615-1619
  • Matsuhiro, B., Urzúa, C.C., (1996) Hydrobiologia, 326-327, pp. 491-495
  • Okazaki, M., Furuya, K., Tsukayama, K., Nisizawa, K., (1982) Bot. Mar., 25, pp. 123-131
  • Usov, A.I., Bilan, M.I., Klochkova, M.G., (1995) Bot. Mar., 38, pp. 43-51
  • Usov, A.I., Yarotsky, S.V., Shaskov, A.S., (1980) Biopolymers, 19, pp. 977-990
  • Farías, W.R.L., Valente, A.-P., Pereira, M.S., Mourao, P.A.S., (2000) J. Biol. Chem., 275, pp. 29299-29307
  • Van De Velde, F., Knutsen, S.H., Usov, A.I., Rollema, H.S., Cerezo, A.S., (2002) Trends Food Sci. Technol., 13, pp. 73-92
  • Errea, M.I., Matulewicz, M.C., (2003) Carbohydr. Res., 338, pp. 943-953
  • Miller, I.J., Falshaw, R., Furneaux, R.H., (1996) Hydrobiologia, 326-327, pp. 505-509
  • Falshaw, R., Furneaux, R.H., Miller, I.J., (1999) Bot. Mar., 42, pp. 431-435
  • Lahaye, M., Yaphe, W., Rochas, C., (1985) Carbohydr. Res., 143, pp. 240-245
  • Ciancia, M., Matulewicz, M.C., Cerezo, A.S., (1993) Phytochemistry, 34, pp. 1541-1543
  • Ciancia, M., Matulewicz, M.C., Cerezo, A.S., (1997) Phytochemistry, 45, pp. 1009-1013
  • Takano, R., Iwane-Sakata, H., Hayashi, K., Hara, S., Hirase, S., (1998) Carbohydr. Polym., 35, pp. 81-87
  • Takano, R., Yokoi, T., Kamli, K., Hara, S., Hirase, S., (1999) Bot. Mar., 42, pp. 183-188
  • Estevez, J.M., Ciancia, M., Cerezo, A.S., (2001) Carbohydr. Res., 331, pp. 27-41
  • Zibetti, R.G.M., Noseda, M.D., Cerezo, A.S., Duarte, M.E.R., (2005) Carbohydr. Res., 340, pp. 711-722
  • Hirst, E.L., Percival, E., (1965) Methods Carbohydr. Chem., 5, pp. 287-296
  • Stevenson, T.T., Furneaux, R.H., (1991) Carbohydr. Res., 210, pp. 277-298
  • Mulloy, B., Ribeiro, A.-C., Alves, A.-P., Vieira, R.P., Mourao, P.A.S., (1994) J. Biol. Chem., 269, pp. 22113-22123
  • Duarte, M.E.R., Noseda, M.G., Cardoso, M.A., Tulio, S., Cerezo, A.S., (2002) Carbohydr. Res., 337, pp. 1137-1144
  • Whitley, R.J., Roizman, B., (2001) Lancet, 357, pp. 1513-1518
  • Damonte, E.B., Matulewicz, M.C., Cerezo, A.S., Coto, C.E., (1996) Chemotherapy, 42, pp. 57-64
  • Duarte, M.E.R., Nocedal, D.G., Noseda, M.D., Tulio, S., Pujol, C.A., Damonte, E.B., (2001) Phytomedicine, 8, pp. 53-58
  • Spear, P.G., (1994) Semin. Virol., 4, pp. 67-180
  • Knutsen, S.H., Myslabodski, D., Larsen, B., Usov, A.I., (1994) Bot. Mar., 37, pp. 163-169
  • Chaplin, M.F., Monosaccharides (1986) Carbohydrate Analysis, pp. 1-36. , M.F. Chaplin J.F. Kennedy IRL Press Oxford
  • Filisetti-Cozzi, T.M.C.C., Carpita, N.C., (1991) Anal. Biochem., 197, pp. 157-162
  • Duckworth, W., Yaphe, W., (1970) Chem. Ind. (London), 23, pp. 747-748
  • Lowry, O.H., Rosebrough, N.J., Farr, A.L., Randall, R.J., (1951) J. Biol. Chem., 193, pp. 265-275
  • Hartree, E.F., (1972) Anal. Biochem., 48, pp. 422-427
  • Chandía, N.P., Matsuhiro, B., Vásquez, A.E., (2001) Carbohydr. Polym., 46, pp. 81-87
  • Cases, M.R., Cerezo, A.S., Stortz, C.A., (1995) Carbohydr. Res., 269, pp. 333-341
  • Vogel, A., (1961) Practical Organic Chemistry, , 3rd ed. Longmans New York
  • Cáceres, P., Faúndez, C.A., Matsuhiro, B., Vásquez, J.A., (1997) J. Appl. Phycol., 8, pp. 523-527
  • Taylor, R.L., Shively, J.E., Conrad, H.E., (1976) Methods Carbohydr. Chem., 7, pp. 49-151
  • Ciancia, M., Matulewicz, M.C., Cerezo, A.S., (1995) Anal. Assoc. Quím. Arg., 83, pp. 103-108
  • Falshaw, R., Furneaux, R.H., (1998) Carbohydr. Res., 307, pp. 325-331
  • Ciucanu, I., Kerek, F., (1984) Carbohydr. Res., 131, pp. 209-217
  • Kolender, A.A., Matulewicz, M.C., (2002) Carbohydr. Res., 337, pp. 57-68
  • Sweet, D.P., Shapiro, R.H., Albersheim, P., (1975) Carbohydr. Res., 40, pp. 217-225
  • Cases, M.R., Stortz, C.A., Cerezo, A.S., (1994) J. Chromatogr. a, 662, pp. 293-299
  • Dodgson, K.S., Price, R.G., (1962) Biochem. J., 84, pp. 106-110

Citas:

---------- APA ----------
Matsuhiro, B., Conte, A.F., Damonte, E.B., Kolender, A.A., Matulewicz, M.C., Mejías, E.G., Pujol, C.A.,..., Zúñiga, E.A. (2005) . Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta). Carbohydrate Research, 340(15), 2392-2402.
http://dx.doi.org/10.1016/j.carres.2005.08.004
---------- CHICAGO ----------
Matsuhiro, B., Conte, A.F., Damonte, E.B., Kolender, A.A., Matulewicz, M.C., Mejías, E.G., et al. "Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)" . Carbohydrate Research 340, no. 15 (2005) : 2392-2402.
http://dx.doi.org/10.1016/j.carres.2005.08.004
---------- MLA ----------
Matsuhiro, B., Conte, A.F., Damonte, E.B., Kolender, A.A., Matulewicz, M.C., Mejías, E.G., et al. "Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)" . Carbohydrate Research, vol. 340, no. 15, 2005, pp. 2392-2402.
http://dx.doi.org/10.1016/j.carres.2005.08.004
---------- VANCOUVER ----------
Matsuhiro, B., Conte, A.F., Damonte, E.B., Kolender, A.A., Matulewicz, M.C., Mejías, E.G., et al. Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta). Carbohydr. Res. 2005;340(15):2392-2402.
http://dx.doi.org/10.1016/j.carres.2005.08.004