Navegar

Colección

Datos Estadísticas

Artículo

La versión final de este artículo es de uso interno. El editor solo permite incluir en el repositorio el artículo en su versión post-print. Por favor, si usted la posee enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Natural compounds offer interesting pharmacological perspectives for antiviral drug development with regard to broad-spectrum antiviral properties and novel modes of action. In this study, we have analyzed polysaccharide fractions isolated from Grateloupia indica. The crude water extract (GiWE) as well as one fraction (F3) obtained by anion exchange chromatography had potent anti-HSV activity. Their inhibitory concentration 50% (IC50) values (0.12-1.06 μg/ml) were much lower than cytotoxic concentration 50% values (>850 μg/ml). These fractions, which were effective antiviral inhibitors if added only during the adsorption period, had very low anticoagulant activity. Furthermore, they had no direct inactivating effect on virions in a virucidal assay. Chemical, chromatographic and spectroscopic methods showed that the active polysaccharide, which has an apparent molecular mass of 60 kDa and negative specific rotation [α]D32 -16° (c 0.2, H2O), contains α-(1 → 4)- and α-(1 → 3)-linked galactopyranose residues. Sulfate groups, if present, are located mostly at C-2/6 of (1 → 4)- and C-4/6 of (1 → 3)-linked galactopyranosyl units, and are essential for the anti herpetic activity of this polymer. © 2007 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Galactan sulfate of Grateloupia indica: Isolation, structural features and antiviral activity
Autor:Chattopadhyay, K.; Mateu, C.G.; Mandal, P.; Pujol, C.A.; Damonte, E.B.; Ray, B.
Filiación:Natural Products Laboratory, Department of Chemistry, The University of Burdwan, WB 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:Antiviral activity; Galactan sulfate; Grateloupia indica; Herpes simplex virus; Red algae; anticoagulant agent; antivirus agent; galactan; galactan polysulfate; unclassified drug; article; chemistry; drug effect; Herpes simplex virus 1; Herpes simplex virus 2; isolation and purification; molecular weight; nuclear magnetic resonance; red alga; Algae, Red; Anticoagulants; Antiviral Agents; Galactans; Herpesvirus 1, Human; Herpesvirus 2, Human; Molecular Weight; Nuclear Magnetic Resonance, Biomolecular; Grateloupia; Rhodophyta; Simplexvirus
Año:2007
Volumen:68
Número:10
Página de inicio:1428
Página de fin:1435
DOI: http://dx.doi.org/10.1016/j.phytochem.2007.02.008
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
ISSN:00319422
CODEN:PYTCA
CAS:galactan, 39300-87-3, 9037-55-2; Anticoagulants; Antiviral Agents; Galactans; galactan polysulfate, 39475-64-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v68_n10_p1428_Chattopadhyay

Referencias:

  • 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, pp. 2474-2482
  • 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
  • Aquino, R.S., Landeira-Fernandez, A.M., Valente, A.P., Andrade, L.R., Mourao, P.A.S., Occurrence of sulfated galactans in marine angiosperms: evolutionary implications (2005) Glycobiology, 15, pp. 11-20
  • 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
  • Blakeney, A.B., Stone, B.A., Methylation of carbohydrates with lithium methylsulphinyl carbanion (1985) Carbohydrate Research, 140, pp. 319-324
  • Carlucci, M.J., Scolaro, L.A., Damonte, E.B., Herpes simplex 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
  • Carlucci, M.J., Ciancia, M., Matulewicz, M.C., Cerezo, A.S., Damonte, E.B., Antiherpetic activity and mode of action of natural carrageenans of diverse structural types (1999) Antiviral Research, 43, pp. 93-102
  • Carlucci, M.J., Scolaro, L.A., Errea, M.I., Matulewicz, M.C., Damonte, E.B., Antiviral activity of natural sulphated galactans on herpes virus multiplication in cell culture (1997) Planta Medica, 63, pp. 429-432
  • Damonte, E.B., Matulewicz, M.C., Cerezo, A.S., Sulfated seaweed polysaccharides as antiviral agents (2004) Current Medicinal Chemistry, 11, pp. 2399-2419
  • Darcy-Vrillon, B., Nutritional aspects of the developing use of marine macroalgae for the human food industry (1993) International Journal of Food Science & Nutrition, 44, pp. S23-S35
  • 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 (3), pp. 350-366
  • Falshaw, R., Furneaux, R.H., Structural analysis of carrageenans from the tetrasporic stages of the red algae, Gigartina lanceata and Gigartina chapmanii (Gigartinaceae, Rhodophyta) (1998) Carbohydrate Research, 7, pp. 325-331
  • Farias, W.R.L., Valente, A.-P., Pereira, M.S., Mourao, P.A.S., Structure and anticoagulant activity of sulfated galactans Isolation of a unique sulfated galactan from the red algae Botryocladia occidentalis and comparison of its anticoagulant action with that of sulfated galactans from invertebrates (2000) The Journal of Biological Chemistry, 275, pp. 29299-29307
  • Franz, G., Paper, 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
  • Gunay, N.S., Linhardt, R.J., Heparinoids: structure, biological activities and therapeutic applications (1999) Planta Medica, 65, pp. 301-306
  • Hosoya, M., Balzarini, J., Shigeta, S., De Clercq, E., Differential inhibitory effects of sulfated polysaccharides and polymers on the replication of various myxoviruses and retroviruses, depending on the composition of the target amino acid sequences of the viral envelope glycoproteins (1991) Antimicrobial Agents Chemother, 35, pp. 2515-2520
  • Indergaard, M., Minsaas, J., Animal and human nutrition (1991) Seaweed Resources in Europe: Uses and Potential, pp. 21-64. , Guiry M.D., and Blunden G. (Eds), Wiley, Chichester
  • Knutsen, S.H., Myslabodsky, D.E., Larsen, B., Usov, A.I., A modified system of nomenclature for red algal galactans (1994) Botanica Marina, 37, pp. 163-169
  • Lewis, J.G., Stanley, N.F., Guist, G.G., (1988) Algae and Human Affairs, pp. 205-236. , Lembi C.A., and Waaland J.R. (Eds), Cambridge University Press, New York
  • Lloyd, A.G., Dodgson, K.S., Price, R.B., Rose, F.A., I. Polysaccharide Sulphates (1961) Biochimica et Biophysica Acta, 46, pp. 108-115
  • 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, pp. 2392-2402
  • Mazumder, S., Lerouge, P., Loutelier-Bourhis, C., Driouich, A., Ray, B., Structural characterisation of hemicellulosic polysaccharides from Benincasa hispida using specific enzyme hydrolysis, ion exchange chromatography and MALDI-TOF mass spectroscopy (2005) Carbohydrate Polymers, 59 (2), pp. 231-238
  • 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 Macromolecule, 31, pp. 87-95
  • 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., Vilela-Silva, A.-C.E.S., Valente, A.-P., Mourao, P.A.S., A 2-sulfated, 3-linked-galactan is an anticoagulant polysaccharide (2002) Carbohydrate Research, 337, pp. 2231-2238
  • 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., Polysaccharides from Enteromorpha compressa: isolation, purification and structural features (2006) Carbohydrate Polymers, 66, pp. 408-416
  • 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
  • Rechter, S., König, T., Auerochs, S., Thulke, S., Walter, H., Dörnenburg, H., Walter, C., Marschall, M., Antiviral activity of Arthrospira-derived spirulan-like substances (2006) Antiviral Research, 72, pp. 197-206
  • Renn, D., Biotechnology and the red seaweed polysaccharide industry: status, needs and prospects (1997) TIBTECH, 15, pp. 9-14
  • Rochas, C., Lahaye, M., Yaphe, W., Sulfate content of carrageenan and agar determined by infrared spectroscopy (1986) Botanica Marina, 29, pp. 335-340
  • Schaeffer, D.J., Krylov, V.S., Anti-HIV activity of extracts and compounds from algae and cyanobacteria (2000) Ecotoxicology and Environmental Safety, 45, pp. 208-227
  • Sen, A.K., Das, A.K., Banerji, N., Siddhanta, A.K., Mody, K.H., Ramavat, B.K., Chauhan, V.D., Ganguly, D.K., A new sulfated polysaccharide with potent blood anti-coagulant activity from the red seaweed Grateloupia indica (1994) International Journal of Biological Macromolecule, 16, pp. 279-280
  • Skjak-Braek, G., Martinsen, A., (1991) Seaweed Resources in Europe: Uses and Potential, pp. 219-256. , Guiry M.D., and Blunden G. (Eds), John Wiley & Sons
  • Stephen, A.M., (1995) Food Polysaccharides and Their Applications, , Marcel Dekker, New York
  • Stevenson, T.T., Furneaux, R.H., Chemical methods for the analysis of sulphated galactans from red algae (1991) Carbohydrate Research, 210, pp. 277-298
  • Talarico, L.B., Zibetti, R.G.M., Faria, P.C.S., Scolaro, L.A., Duarte, M.E.R., Noseda, M.D., Pujol, C.A., Damonte, E.B., Anti-herpes simplex virus activity of sulfated galactans from the red seaweeds Gymnogongrus griffithsiae and Cryptonemia crenulata (2004) International Journal of Biological Macromolecules, 34, pp. 63-71
  • Tischer, P.C.S.F., Talarico, L.B., Noseda, M.D., Guimarães, S.M.P.B., Damonte, E.B., Duarte, M.E.R., Chemical structure and antiviral activity of carrageenans from Meristiella gelidium against herpes simplex and dengue virus (2006) Carbohydrate Polymers, 63, pp. 459-465
  • Turvey, J.R., Williams, T.P., Sulfates of monosaccharides and derivatives. Part IV. Galactose 4-sulfate (1962) Journal of Chemical Society, pp. 2119-2122
  • Witvrouw, M., De Clercq, E., Sulfated polysaccharides extracted from sea algae as potential antiviral drugs (1997) General Pharmacology, 29, pp. 497-511
  • York, W.S., Darvill, A., O'Neill, M., Stevenson, T., Albersheim, P., Isolation and characterisation of plant cell walls and cell wall components (1985) Methods in Enzymology, 118, pp. 3-40;

Citas:

---------- APA ----------
Chattopadhyay, K., Mateu, C.G., Mandal, P., Pujol, C.A., Damonte, E.B. & Ray, B. (2007) . Galactan sulfate of Grateloupia indica: Isolation, structural features and antiviral activity. Phytochemistry, 68(10), 1428-1435.
http://dx.doi.org/10.1016/j.phytochem.2007.02.008
---------- CHICAGO ----------
Chattopadhyay, K., Mateu, C.G., Mandal, P., Pujol, C.A., Damonte, E.B., Ray, B. "Galactan sulfate of Grateloupia indica: Isolation, structural features and antiviral activity" . Phytochemistry 68, no. 10 (2007) : 1428-1435.
http://dx.doi.org/10.1016/j.phytochem.2007.02.008
---------- MLA ----------
Chattopadhyay, K., Mateu, C.G., Mandal, P., Pujol, C.A., Damonte, E.B., Ray, B. "Galactan sulfate of Grateloupia indica: Isolation, structural features and antiviral activity" . Phytochemistry, vol. 68, no. 10, 2007, pp. 1428-1435.
http://dx.doi.org/10.1016/j.phytochem.2007.02.008
---------- VANCOUVER ----------
Chattopadhyay, K., Mateu, C.G., Mandal, P., Pujol, C.A., Damonte, E.B., Ray, B. Galactan sulfate of Grateloupia indica: Isolation, structural features and antiviral activity. Phytochemistry. 2007;68(10):1428-1435.
http://dx.doi.org/10.1016/j.phytochem.2007.02.008