Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)

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 dev...

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Autores principales:	Matsuhiro, Betty, Damonte, Elsa Beatriz, Kolender, Adriana Andrea, Matulewicz, María Cristina, Pujol, Carlos Alberto
Publicado:	2005
Materias:	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 Schizymenia Simplexvirus
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v340_n15_p2392_Matsuhiro http://hdl.handle.net/20.500.12110/paper_00086215_v340_n15_p2392_Matsuhiro
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00086215_v340_n15_p2392_Matsuhiro
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spelling	paper:paper_00086215_v340_n15_p2392_Matsuhiro2023-06-08T14:32:49Z Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta) Matsuhiro, Betty Damonte, Elsa Beatriz Kolender, Adriana Andrea Matulewicz, María Cristina Pujol, Carlos Alberto 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 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. Fil:Matsuhiro, B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Damonte, E.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Kolender, A.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Matulewicz, M.C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Pujol, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2005 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v340_n15_p2392_Matsuhiro http://hdl.handle.net/20.500.12110/paper_00086215_v340_n15_p2392_Matsuhiro
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 Matsuhiro, Betty Damonte, Elsa Beatriz Kolender, Adriana Andrea Matulewicz, María Cristina Pujol, Carlos Alberto Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)
topic_facet	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
description	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.
author	Matsuhiro, Betty Damonte, Elsa Beatriz Kolender, Adriana Andrea Matulewicz, María Cristina Pujol, Carlos Alberto
author_facet	Matsuhiro, Betty Damonte, Elsa Beatriz Kolender, Adriana Andrea Matulewicz, María Cristina Pujol, Carlos Alberto
author_sort	Matsuhiro, Betty
title	Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)
title_short	Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)
title_full	Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)
title_fullStr	Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)
title_full_unstemmed	Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)
title_sort	structural analysis and antiviral activity of a sulfated galactan from the red seaweed schizymenia binderi (gigartinales, rhodophyta)
publishDate	2005
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v340_n15_p2392_Matsuhiro http://hdl.handle.net/20.500.12110/paper_00086215_v340_n15_p2392_Matsuhiro
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Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta)

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