Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum

Autores
Adhikari, Utpal; Mateu, Cecilia Gabriela; Chattopadhyay, Kausik; Pujol, Carlos Alberto; Damonte, Elsa Beatriz; Ray, Bimalendu
Año de publicación
2006
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A sulfated fucan containing fraction (SmWE) was isolated from water extract of the brown seaweed Stoechospermum marginatum collected from the Arabian Sea. Anion exchange chromatography of the crude fraction results in the production of a sulfated fucan (F3) having a molecular mass of 40 kDa and specific rotation [α]D30 - 124° (c 0.5, H2O). NMR spectroscopic studies and methylation analysis suggested that the polymer consists of a backbone of (1 → 4)- and (1 → 3)-linked-α-l-fucopyranosyl residues that are substituted at C-2 and C-3, and that fucosyl residues are sulfated mostly at C-2 and/or C-4. SmWE and F3 were selective inhibitors of herpes simplex virus type 1 (strain F, thymidine kinase-deficient strains field and B2006 and syncytial variants arising after selection with a natural carrageenan syn 13-8 and 14-1) and type 2 (strain MS) in Vero cells, with antiviral effective concentration 50% (EC50) values in the range 0.63-10.0 μg/ml. The compounds were highly selective due to the lack of cytotoxicity. The antiviral activity was dependent on the presence of the sulfated fucans during the adsorption period. No direct inactivating effect on virions was observed in a virucidal assay. The absence of anticoagulant activity at concentrations near EC50 confirmed that there was no correlation between the antiviral and anticoagulant properties.
Fil: Adhikari, Utpal. University of Burdwan; India
Fil: Mateu, Cecilia Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina
Fil: Chattopadhyay, Kausik. University of Burdwan; India
Fil: Pujol, Carlos Alberto. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Damonte, Elsa Beatriz. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Ray, Bimalendu. University of Burdwan; India
Materia
ANTICOAGULANT ACTIVITY
ANTIVIRAL AGENT
HERPES SIMPLEX VIRUS
METHYLATION ANALYSIS
MOLECULAR MASS
NMR SPECTROSCOPY
STOECHOSPERMUM MARGINATUM
SULFATED FUCAN
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/98930
Acceder
id CONICETDig_82f6f2f4e2f0cca67785398a49576237
oai_identifier_str oai:ri.conicet.gov.ar:11336/98930
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Structure and antiviral activity of sulfated fucans from Stoechospermum marginatumAdhikari, UtpalMateu, Cecilia GabrielaChattopadhyay, KausikPujol, Carlos AlbertoDamonte, Elsa BeatrizRay, BimalenduANTICOAGULANT ACTIVITYANTIVIRAL AGENTHERPES SIMPLEX VIRUSMETHYLATION ANALYSISMOLECULAR MASSNMR SPECTROSCOPYSTOECHOSPERMUM MARGINATUMSULFATED FUCANhttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1A sulfated fucan containing fraction (SmWE) was isolated from water extract of the brown seaweed Stoechospermum marginatum collected from the Arabian Sea. Anion exchange chromatography of the crude fraction results in the production of a sulfated fucan (F3) having a molecular mass of 40 kDa and specific rotation [α]D30 - 124° (c 0.5, H2O). NMR spectroscopic studies and methylation analysis suggested that the polymer consists of a backbone of (1 → 4)- and (1 → 3)-linked-α-l-fucopyranosyl residues that are substituted at C-2 and C-3, and that fucosyl residues are sulfated mostly at C-2 and/or C-4. SmWE and F3 were selective inhibitors of herpes simplex virus type 1 (strain F, thymidine kinase-deficient strains field and B2006 and syncytial variants arising after selection with a natural carrageenan syn 13-8 and 14-1) and type 2 (strain MS) in Vero cells, with antiviral effective concentration 50% (EC50) values in the range 0.63-10.0 μg/ml. The compounds were highly selective due to the lack of cytotoxicity. The antiviral activity was dependent on the presence of the sulfated fucans during the adsorption period. No direct inactivating effect on virions was observed in a virucidal assay. The absence of anticoagulant activity at concentrations near EC50 confirmed that there was no correlation between the antiviral and anticoagulant properties.Fil: Adhikari, Utpal. University of Burdwan; IndiaFil: Mateu, Cecilia Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; ArgentinaFil: Chattopadhyay, Kausik. University of Burdwan; IndiaFil: Pujol, Carlos Alberto. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Damonte, Elsa Beatriz. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Ray, Bimalendu. University of Burdwan; IndiaPergamon-Elsevier Science Ltd2006-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/98930Adhikari, Utpal; Mateu, Cecilia Gabriela; Chattopadhyay, Kausik; Pujol, Carlos Alberto; Damonte, Elsa Beatriz; et al.; Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum; Pergamon-Elsevier Science Ltd; Phytochemistry; 67; 22; 11-2006; 2474-24820031-9422CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0031942206002937info:eu-repo/semantics/altIdentifier/doi/10.1016/j.phytochem.2006.05.024info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:11:27Zoai:ri.conicet.gov.ar:11336/98930instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:11:27.652CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum
title Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum
spellingShingle Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum
Adhikari, Utpal
ANTICOAGULANT ACTIVITY
ANTIVIRAL AGENT
HERPES SIMPLEX VIRUS
METHYLATION ANALYSIS
MOLECULAR MASS
NMR SPECTROSCOPY
STOECHOSPERMUM MARGINATUM
SULFATED FUCAN
title_short Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum
title_full Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum
title_fullStr Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum
title_full_unstemmed Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum
title_sort Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum
dc.creator.none.fl_str_mv Adhikari, Utpal
Mateu, Cecilia Gabriela
Chattopadhyay, Kausik
Pujol, Carlos Alberto
Damonte, Elsa Beatriz
Ray, Bimalendu
author Adhikari, Utpal
author_facet Adhikari, Utpal
Mateu, Cecilia Gabriela
Chattopadhyay, Kausik
Pujol, Carlos Alberto
Damonte, Elsa Beatriz
Ray, Bimalendu
author_role author
author2 Mateu, Cecilia Gabriela
Chattopadhyay, Kausik
Pujol, Carlos Alberto
Damonte, Elsa Beatriz
Ray, Bimalendu
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv ANTICOAGULANT ACTIVITY
ANTIVIRAL AGENT
HERPES SIMPLEX VIRUS
METHYLATION ANALYSIS
MOLECULAR MASS
NMR SPECTROSCOPY
STOECHOSPERMUM MARGINATUM
SULFATED FUCAN
topic ANTICOAGULANT ACTIVITY
ANTIVIRAL AGENT
HERPES SIMPLEX VIRUS
METHYLATION ANALYSIS
MOLECULAR MASS
NMR SPECTROSCOPY
STOECHOSPERMUM MARGINATUM
SULFATED FUCAN
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A sulfated fucan containing fraction (SmWE) was isolated from water extract of the brown seaweed Stoechospermum marginatum collected from the Arabian Sea. Anion exchange chromatography of the crude fraction results in the production of a sulfated fucan (F3) having a molecular mass of 40 kDa and specific rotation [α]D30 - 124° (c 0.5, H2O). NMR spectroscopic studies and methylation analysis suggested that the polymer consists of a backbone of (1 → 4)- and (1 → 3)-linked-α-l-fucopyranosyl residues that are substituted at C-2 and C-3, and that fucosyl residues are sulfated mostly at C-2 and/or C-4. SmWE and F3 were selective inhibitors of herpes simplex virus type 1 (strain F, thymidine kinase-deficient strains field and B2006 and syncytial variants arising after selection with a natural carrageenan syn 13-8 and 14-1) and type 2 (strain MS) in Vero cells, with antiviral effective concentration 50% (EC50) values in the range 0.63-10.0 μg/ml. The compounds were highly selective due to the lack of cytotoxicity. The antiviral activity was dependent on the presence of the sulfated fucans during the adsorption period. No direct inactivating effect on virions was observed in a virucidal assay. The absence of anticoagulant activity at concentrations near EC50 confirmed that there was no correlation between the antiviral and anticoagulant properties.
Fil: Adhikari, Utpal. University of Burdwan; India
Fil: Mateu, Cecilia Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina
Fil: Chattopadhyay, Kausik. University of Burdwan; India
Fil: Pujol, Carlos Alberto. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Damonte, Elsa Beatriz. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Ray, Bimalendu. University of Burdwan; India
description A sulfated fucan containing fraction (SmWE) was isolated from water extract of the brown seaweed Stoechospermum marginatum collected from the Arabian Sea. Anion exchange chromatography of the crude fraction results in the production of a sulfated fucan (F3) having a molecular mass of 40 kDa and specific rotation [α]D30 - 124° (c 0.5, H2O). NMR spectroscopic studies and methylation analysis suggested that the polymer consists of a backbone of (1 → 4)- and (1 → 3)-linked-α-l-fucopyranosyl residues that are substituted at C-2 and C-3, and that fucosyl residues are sulfated mostly at C-2 and/or C-4. SmWE and F3 were selective inhibitors of herpes simplex virus type 1 (strain F, thymidine kinase-deficient strains field and B2006 and syncytial variants arising after selection with a natural carrageenan syn 13-8 and 14-1) and type 2 (strain MS) in Vero cells, with antiviral effective concentration 50% (EC50) values in the range 0.63-10.0 μg/ml. The compounds were highly selective due to the lack of cytotoxicity. The antiviral activity was dependent on the presence of the sulfated fucans during the adsorption period. No direct inactivating effect on virions was observed in a virucidal assay. The absence of anticoagulant activity at concentrations near EC50 confirmed that there was no correlation between the antiviral and anticoagulant properties.
publishDate 2006
dc.date.none.fl_str_mv 2006-11
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/98930
Adhikari, Utpal; Mateu, Cecilia Gabriela; Chattopadhyay, Kausik; Pujol, Carlos Alberto; Damonte, Elsa Beatriz; et al.; Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum; Pergamon-Elsevier Science Ltd; Phytochemistry; 67; 22; 11-2006; 2474-2482
0031-9422
CONICET Digital
CONICET
url http://hdl.handle.net/11336/98930
identifier_str_mv Adhikari, Utpal; Mateu, Cecilia Gabriela; Chattopadhyay, Kausik; Pujol, Carlos Alberto; Damonte, Elsa Beatriz; et al.; Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum; Pergamon-Elsevier Science Ltd; Phytochemistry; 67; 22; 11-2006; 2474-2482
0031-9422
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0031942206002937
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.phytochem.2006.05.024
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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