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Abstract:

A homogeneous sulfated heterorhamnan was obtained by aqueous extraction, then by ultrafiltration from the green seaweed Gayralia oxysperma. Besides α-l-rhamnose it contains glucuronic and galacturonic acids, xylose and glucose. The structure was established by methylation analyses of the carboxyl-reduced, carboxyl-reduced/desulfated, carboxyl-reduced/Smith-degraded, and carboxyl-reduced/Smith-degraded/desulfated products and 1D, 2D NMR spectroscopy analyses. The heterorhamnan backbone is constituted by 3- and 2-linked rhamnosyl units (1.00:0.80), the latter being ∼50% substituted at C-3 by side chains containing 2-sulfated glucuronic and galacturonic acids and xylosyl units. The 3- and 2-linked rhamnosyl units are unsulfated (20%), disulfated (16%), and mostly monosulfated at C-2 (27%) and C-4 (37%). The branched and sulfated heterorhamnan had high and specific activity against herpes simplex virus. © 2008 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Chemical structure and antiviral activity of the sulfated heterorhamnan isolated from the green seaweed Gayralia oxysperma
Autor:Cassolato, J.E.F.; Noseda, M.D.; Pujol, C.A.; Pellizzari, F.M.; Damonte, E.B.; Duarte, M.E.R.
Filiación:Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Parana. PO Box 19046, CEP: 81531-990 Curitiba, Parana, Brazil
Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
Departamento de Ciências Biológicas, Faculdade Estadual de Paranaguá, Paranaguá, Paraná, Brazil
Palabras clave:Antiviral activity; Chemical structure; Gayralia oxysperma; Green seaweed; Sulfated heterorhamnan; Ulvales; Acids; Glucose; Nuclear magnetic resonance; Nuclear magnetic resonance spectroscopy; Solvent extraction; Structure (composition); Ultrafiltration; Antiviral activity; Chemical structure; Gayralia oxysperma; Green seaweed; Sulfated heterorhamnan; Ulvales; Seaweed; carboxyl group; galacturonic acid; glucose; glucuronic acid; polysaccharide sulfate; rhamnose; sulfated heterorhamnan; unclassified drug; xylose; animal cell; antiviral activity; article; chemical structure; concentration response; drug screening; Gayralia oxyspermia; Herpes simplex virus 1; Herpes simplex virus 2; methylation; nonhuman; nuclear magnetic resonance spectroscopy; priority journal; seaweed; substitution reaction; sulfation; ultrafiltration; Algae, Green; Animals; Antiviral Agents; Carbon Dioxide; Cell Survival; Cercopithecus aethiops; Deoxy Sugars; Herpesvirus 1, Human; Herpesvirus 2, Human; Magnetic Resonance Spectroscopy; Mannans; Methylation; Oxidation-Reduction; Solubility; Spectroscopy, Fourier Transform Infrared; Sulfuric Acid Esters; Vero Cells; Water; Gayralia oxysperma; Simplexvirus; Ulvales
Año:2008
Volumen:343
Número:18
Página de inicio:3085
Página de fin:3095
DOI: http://dx.doi.org/10.1016/j.carres.2008.09.014
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:galacturonic acid, 14982-50-4, 685-73-4; glucose, 50-99-7, 84778-64-3; glucuronic acid, 36116-79-7, 576-37-4, 6556-12-3; polysaccharide sulfate, 79933-28-1; rhamnose, 10485-94-6, 3615-41-6; xylose, 25990-60-7, 58-86-6; Antiviral Agents; Carbon Dioxide, 124-38-9; carboxyl radical, 14485-07-5; Deoxy Sugars; Mannans; rhamnan, 111018-90-7; Sulfuric Acid Esters; Water, 7732-18-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v343_n18_p3085_Cassolato

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Citas:

---------- APA ----------
Cassolato, J.E.F., Noseda, M.D., Pujol, C.A., Pellizzari, F.M., Damonte, E.B. & Duarte, M.E.R. (2008) . Chemical structure and antiviral activity of the sulfated heterorhamnan isolated from the green seaweed Gayralia oxysperma. Carbohydrate Research, 343(18), 3085-3095.
http://dx.doi.org/10.1016/j.carres.2008.09.014
---------- CHICAGO ----------
Cassolato, J.E.F., Noseda, M.D., Pujol, C.A., Pellizzari, F.M., Damonte, E.B., Duarte, M.E.R. "Chemical structure and antiviral activity of the sulfated heterorhamnan isolated from the green seaweed Gayralia oxysperma" . Carbohydrate Research 343, no. 18 (2008) : 3085-3095.
http://dx.doi.org/10.1016/j.carres.2008.09.014
---------- MLA ----------
Cassolato, J.E.F., Noseda, M.D., Pujol, C.A., Pellizzari, F.M., Damonte, E.B., Duarte, M.E.R. "Chemical structure and antiviral activity of the sulfated heterorhamnan isolated from the green seaweed Gayralia oxysperma" . Carbohydrate Research, vol. 343, no. 18, 2008, pp. 3085-3095.
http://dx.doi.org/10.1016/j.carres.2008.09.014
---------- VANCOUVER ----------
Cassolato, J.E.F., Noseda, M.D., Pujol, C.A., Pellizzari, F.M., Damonte, E.B., Duarte, M.E.R. Chemical structure and antiviral activity of the sulfated heterorhamnan isolated from the green seaweed Gayralia oxysperma. Carbohydr. Res. 2008;343(18):3085-3095.
http://dx.doi.org/10.1016/j.carres.2008.09.014