Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats

Autores
Favier, Laura Silvina; María, Alejandra O. M.; Wendel, Graciela Haydée; Borkowski, Eduardo Jorge; Giordano, Oscar Santiago; Pelzer, Lilian Eugenia; Tonn, Carlos Eugenio
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The preventive effect of natural xanthanolides as well as a series of synthetic derivatives on ulcer formation induced by absolute ethanol in rats was examined. Among the compounds tested, xanthatin gave the strongest protective activity. The inhibitory action exerted by this molecule on the lesions induced by 0.6N HCl and 0.2N NaOH was highly significant, reducing ulceration in the range of 58-96% at a dose from 12.5 to 100 mg/kg. These results appear to confirm that the presence of a non-hindered α,β-unsaturated carbonyl group seems to be an essential structural requirement for the gastric cytoprotective activity of these compounds. In order to explore this possibility, a theoretical conformational analysis was performed. We suggest that the mechanism of protection would involve, at least in part, a nucleophylic attack of the sulfhydryl group from the biological molecules present in the gastric mucosa to electrophylic carbons accessible in suitable Michael acceptors.
Fil: Favier, Laura Silvina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: María, Alejandra O. M.. Universidad Nacional de San Luis; Argentina
Fil: Wendel, Graciela Haydée. Universidad Nacional de San Luis; Argentina
Fil: Borkowski, Eduardo Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Giordano, Oscar Santiago. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Pelzer, Lilian Eugenia. Universidad Nacional de San Luis; Argentina
Fil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Materia
GASTRIC
GASTRIC ANTI-ULCER ACTIVITY
XANTHANOLIDES
XANTHATIN
XANTHIUM CAVANILLESII
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:11336/184063
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/184063
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in ratsFavier, Laura SilvinaMaría, Alejandra O. M.Wendel, Graciela HaydéeBorkowski, Eduardo JorgeGiordano, Oscar SantiagoPelzer, Lilian EugeniaTonn, Carlos EugenioGASTRICGASTRIC ANTI-ULCER ACTIVITYXANTHANOLIDESXANTHATINXANTHIUM CAVANILLESIIhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The preventive effect of natural xanthanolides as well as a series of synthetic derivatives on ulcer formation induced by absolute ethanol in rats was examined. Among the compounds tested, xanthatin gave the strongest protective activity. The inhibitory action exerted by this molecule on the lesions induced by 0.6N HCl and 0.2N NaOH was highly significant, reducing ulceration in the range of 58-96% at a dose from 12.5 to 100 mg/kg. These results appear to confirm that the presence of a non-hindered α,β-unsaturated carbonyl group seems to be an essential structural requirement for the gastric cytoprotective activity of these compounds. In order to explore this possibility, a theoretical conformational analysis was performed. We suggest that the mechanism of protection would involve, at least in part, a nucleophylic attack of the sulfhydryl group from the biological molecules present in the gastric mucosa to electrophylic carbons accessible in suitable Michael acceptors.Fil: Favier, Laura Silvina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: María, Alejandra O. M.. Universidad Nacional de San Luis; ArgentinaFil: Wendel, Graciela Haydée. Universidad Nacional de San Luis; ArgentinaFil: Borkowski, Eduardo Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Giordano, Oscar Santiago. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Pelzer, Lilian Eugenia. Universidad Nacional de San Luis; ArgentinaFil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaElsevier Ireland2005-09info: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/11336/184063Favier, Laura Silvina; María, Alejandra O. M.; Wendel, Graciela Haydée; Borkowski, Eduardo Jorge; Giordano, Oscar Santiago; et al.; Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats; Elsevier Ireland; Journal of Ethnopharmacology; 100; 3; 9-2005; 260-2670378-8741CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0378874105002205info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jep.2005.02.042info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:36:57Zoai:ri.conicet.gov.ar:11336/184063instacron: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 09:36:57.424CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats
title Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats
spellingShingle Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats
Favier, Laura Silvina
GASTRIC
GASTRIC ANTI-ULCER ACTIVITY
XANTHANOLIDES
XANTHATIN
XANTHIUM CAVANILLESII
title_short Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats
title_full Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats
title_fullStr Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats
title_full_unstemmed Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats
title_sort Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats
dc.creator.none.fl_str_mv Favier, Laura Silvina
María, Alejandra O. M.
Wendel, Graciela Haydée
Borkowski, Eduardo Jorge
Giordano, Oscar Santiago
Pelzer, Lilian Eugenia
Tonn, Carlos Eugenio
author Favier, Laura Silvina
author_facet Favier, Laura Silvina
María, Alejandra O. M.
Wendel, Graciela Haydée
Borkowski, Eduardo Jorge
Giordano, Oscar Santiago
Pelzer, Lilian Eugenia
Tonn, Carlos Eugenio
author_role author
author2 María, Alejandra O. M.
Wendel, Graciela Haydée
Borkowski, Eduardo Jorge
Giordano, Oscar Santiago
Pelzer, Lilian Eugenia
Tonn, Carlos Eugenio
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv GASTRIC
GASTRIC ANTI-ULCER ACTIVITY
XANTHANOLIDES
XANTHATIN
XANTHIUM CAVANILLESII
topic GASTRIC
GASTRIC ANTI-ULCER ACTIVITY
XANTHANOLIDES
XANTHATIN
XANTHIUM CAVANILLESII
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The preventive effect of natural xanthanolides as well as a series of synthetic derivatives on ulcer formation induced by absolute ethanol in rats was examined. Among the compounds tested, xanthatin gave the strongest protective activity. The inhibitory action exerted by this molecule on the lesions induced by 0.6N HCl and 0.2N NaOH was highly significant, reducing ulceration in the range of 58-96% at a dose from 12.5 to 100 mg/kg. These results appear to confirm that the presence of a non-hindered α,β-unsaturated carbonyl group seems to be an essential structural requirement for the gastric cytoprotective activity of these compounds. In order to explore this possibility, a theoretical conformational analysis was performed. We suggest that the mechanism of protection would involve, at least in part, a nucleophylic attack of the sulfhydryl group from the biological molecules present in the gastric mucosa to electrophylic carbons accessible in suitable Michael acceptors.
Fil: Favier, Laura Silvina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: María, Alejandra O. M.. Universidad Nacional de San Luis; Argentina
Fil: Wendel, Graciela Haydée. Universidad Nacional de San Luis; Argentina
Fil: Borkowski, Eduardo Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Giordano, Oscar Santiago. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Pelzer, Lilian Eugenia. Universidad Nacional de San Luis; Argentina
Fil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
description The preventive effect of natural xanthanolides as well as a series of synthetic derivatives on ulcer formation induced by absolute ethanol in rats was examined. Among the compounds tested, xanthatin gave the strongest protective activity. The inhibitory action exerted by this molecule on the lesions induced by 0.6N HCl and 0.2N NaOH was highly significant, reducing ulceration in the range of 58-96% at a dose from 12.5 to 100 mg/kg. These results appear to confirm that the presence of a non-hindered α,β-unsaturated carbonyl group seems to be an essential structural requirement for the gastric cytoprotective activity of these compounds. In order to explore this possibility, a theoretical conformational analysis was performed. We suggest that the mechanism of protection would involve, at least in part, a nucleophylic attack of the sulfhydryl group from the biological molecules present in the gastric mucosa to electrophylic carbons accessible in suitable Michael acceptors.
publishDate 2005
dc.date.none.fl_str_mv 2005-09
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/11336/184063
Favier, Laura Silvina; María, Alejandra O. M.; Wendel, Graciela Haydée; Borkowski, Eduardo Jorge; Giordano, Oscar Santiago; et al.; Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats; Elsevier Ireland; Journal of Ethnopharmacology; 100; 3; 9-2005; 260-267
0378-8741
CONICET Digital
CONICET
url http://hdl.handle.net/11336/184063
identifier_str_mv Favier, Laura Silvina; María, Alejandra O. M.; Wendel, Graciela Haydée; Borkowski, Eduardo Jorge; Giordano, Oscar Santiago; et al.; Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats; Elsevier Ireland; Journal of Ethnopharmacology; 100; 3; 9-2005; 260-267
0378-8741
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/S0378874105002205
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jep.2005.02.042
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 Elsevier Ireland
publisher.none.fl_str_mv Elsevier Ireland
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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