QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic

Autores
Camargo, Alejandra Beatriz; Marchevsky, Eduardo Jorge; Luco, Juan Maria
Año de publicación
2007
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this study, multiple linear regression (MLR) and partial least-squares (PLS) techniques were used for modeling the soybean 15-lipoxygenase inhibitory activity of a varied group of mono-, di-, and trisulfides derived from the essential oil of garlic. The structures of the compounds under study were characterized by means of calculated physicochemical parameters and several nonempirical descriptors, such as topological, geometrical, and quantum chemical indices. The results obtained indicate that the inhibitory activity is strongly dependent on the ability of the compounds to participate in dispersive interactions with the enzyme, as expressed by the solvent-accessible surface area (SASA) and the average distance/distance degree descriptor (ADDD) index. On the other hand, the high contribution of the lowest unoccupied molecular orbit term (LUMO) in the PLS models derived for the di- and trisulfides suggests that the solute's electron-acceptor capacity plays a fundamental role in the inhibitory activity exhibited for these compounds. Finally, the geometric features as expressed by the shape parameters included in the models indicate a low but not negligible positive contribution of molecular linearity in the enzyme-inhibitor binding. In summary, the developed quantitative structure-activity relationship approach successfully accounts for the potencies of organosulfur compounds acting on soybean 15-lipoxygenase and thereby offers both a guide for the synthesis of new compounds and a hypothesis for the molecular basis of their activity.
Fil: Camargo, Alejandra Beatriz. Universidad Nacional de Cuyo. Facultad de Ciencias Agrarias. Departamento de Ciencias Enológicas y Agroalimentarias. Laboratorio de Residuos Tóxicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Marchevsky, Eduardo Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; Argentina
Fil: Luco, Juan Maria. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Laboratorio de Alimentos; Argentina
Materia
GARLIC
MULTIVARIATE QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS (QSARS)
ORGANOSULFUR COMPOUNDS (OSCS)
SOYBEAN 15-LIPOXYGENASE (15-SLO)
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:11336/93015
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/93015
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlicCamargo, Alejandra BeatrizMarchevsky, Eduardo JorgeLuco, Juan MariaGARLICMULTIVARIATE QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS (QSARS)ORGANOSULFUR COMPOUNDS (OSCS)SOYBEAN 15-LIPOXYGENASE (15-SLO)https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this study, multiple linear regression (MLR) and partial least-squares (PLS) techniques were used for modeling the soybean 15-lipoxygenase inhibitory activity of a varied group of mono-, di-, and trisulfides derived from the essential oil of garlic. The structures of the compounds under study were characterized by means of calculated physicochemical parameters and several nonempirical descriptors, such as topological, geometrical, and quantum chemical indices. The results obtained indicate that the inhibitory activity is strongly dependent on the ability of the compounds to participate in dispersive interactions with the enzyme, as expressed by the solvent-accessible surface area (SASA) and the average distance/distance degree descriptor (ADDD) index. On the other hand, the high contribution of the lowest unoccupied molecular orbit term (LUMO) in the PLS models derived for the di- and trisulfides suggests that the solute's electron-acceptor capacity plays a fundamental role in the inhibitory activity exhibited for these compounds. Finally, the geometric features as expressed by the shape parameters included in the models indicate a low but not negligible positive contribution of molecular linearity in the enzyme-inhibitor binding. In summary, the developed quantitative structure-activity relationship approach successfully accounts for the potencies of organosulfur compounds acting on soybean 15-lipoxygenase and thereby offers both a guide for the synthesis of new compounds and a hypothesis for the molecular basis of their activity.Fil: Camargo, Alejandra Beatriz. Universidad Nacional de Cuyo. Facultad de Ciencias Agrarias. Departamento de Ciencias Enológicas y Agroalimentarias. Laboratorio de Residuos Tóxicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Marchevsky, Eduardo Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; ArgentinaFil: Luco, Juan Maria. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Laboratorio de Alimentos; ArgentinaAmerican Chemical Society2007-04info: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/11336/93015Camargo, Alejandra Beatriz; Marchevsky, Eduardo Jorge; Luco, Juan Maria; QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic; American Chemical Society; Journal of Agricultural and Food Chemistry; 55; 8; 4-2007; 3096-31030021-8561CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jf063020einfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jf063020einfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:40:10Zoai:ri.conicet.gov.ar:11336/93015instacron: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 09:40:10.862CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic
title QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic
spellingShingle QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic
Camargo, Alejandra Beatriz
GARLIC
MULTIVARIATE QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS (QSARS)
ORGANOSULFUR COMPOUNDS (OSCS)
SOYBEAN 15-LIPOXYGENASE (15-SLO)
title_short QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic
title_full QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic
title_fullStr QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic
title_full_unstemmed QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic
title_sort QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic
dc.creator.none.fl_str_mv Camargo, Alejandra Beatriz
Marchevsky, Eduardo Jorge
Luco, Juan Maria
author Camargo, Alejandra Beatriz
author_facet Camargo, Alejandra Beatriz
Marchevsky, Eduardo Jorge
Luco, Juan Maria
author_role author
author2 Marchevsky, Eduardo Jorge
Luco, Juan Maria
author2_role author
author
dc.subject.none.fl_str_mv GARLIC
MULTIVARIATE QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS (QSARS)
ORGANOSULFUR COMPOUNDS (OSCS)
SOYBEAN 15-LIPOXYGENASE (15-SLO)
topic GARLIC
MULTIVARIATE QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS (QSARS)
ORGANOSULFUR COMPOUNDS (OSCS)
SOYBEAN 15-LIPOXYGENASE (15-SLO)
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this study, multiple linear regression (MLR) and partial least-squares (PLS) techniques were used for modeling the soybean 15-lipoxygenase inhibitory activity of a varied group of mono-, di-, and trisulfides derived from the essential oil of garlic. The structures of the compounds under study were characterized by means of calculated physicochemical parameters and several nonempirical descriptors, such as topological, geometrical, and quantum chemical indices. The results obtained indicate that the inhibitory activity is strongly dependent on the ability of the compounds to participate in dispersive interactions with the enzyme, as expressed by the solvent-accessible surface area (SASA) and the average distance/distance degree descriptor (ADDD) index. On the other hand, the high contribution of the lowest unoccupied molecular orbit term (LUMO) in the PLS models derived for the di- and trisulfides suggests that the solute's electron-acceptor capacity plays a fundamental role in the inhibitory activity exhibited for these compounds. Finally, the geometric features as expressed by the shape parameters included in the models indicate a low but not negligible positive contribution of molecular linearity in the enzyme-inhibitor binding. In summary, the developed quantitative structure-activity relationship approach successfully accounts for the potencies of organosulfur compounds acting on soybean 15-lipoxygenase and thereby offers both a guide for the synthesis of new compounds and a hypothesis for the molecular basis of their activity.
Fil: Camargo, Alejandra Beatriz. Universidad Nacional de Cuyo. Facultad de Ciencias Agrarias. Departamento de Ciencias Enológicas y Agroalimentarias. Laboratorio de Residuos Tóxicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Marchevsky, Eduardo Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; Argentina
Fil: Luco, Juan Maria. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Laboratorio de Alimentos; Argentina
description In this study, multiple linear regression (MLR) and partial least-squares (PLS) techniques were used for modeling the soybean 15-lipoxygenase inhibitory activity of a varied group of mono-, di-, and trisulfides derived from the essential oil of garlic. The structures of the compounds under study were characterized by means of calculated physicochemical parameters and several nonempirical descriptors, such as topological, geometrical, and quantum chemical indices. The results obtained indicate that the inhibitory activity is strongly dependent on the ability of the compounds to participate in dispersive interactions with the enzyme, as expressed by the solvent-accessible surface area (SASA) and the average distance/distance degree descriptor (ADDD) index. On the other hand, the high contribution of the lowest unoccupied molecular orbit term (LUMO) in the PLS models derived for the di- and trisulfides suggests that the solute's electron-acceptor capacity plays a fundamental role in the inhibitory activity exhibited for these compounds. Finally, the geometric features as expressed by the shape parameters included in the models indicate a low but not negligible positive contribution of molecular linearity in the enzyme-inhibitor binding. In summary, the developed quantitative structure-activity relationship approach successfully accounts for the potencies of organosulfur compounds acting on soybean 15-lipoxygenase and thereby offers both a guide for the synthesis of new compounds and a hypothesis for the molecular basis of their activity.
publishDate 2007
dc.date.none.fl_str_mv 2007-04
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/11336/93015
Camargo, Alejandra Beatriz; Marchevsky, Eduardo Jorge; Luco, Juan Maria; QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic; American Chemical Society; Journal of Agricultural and Food Chemistry; 55; 8; 4-2007; 3096-3103
0021-8561
CONICET Digital
CONICET
url http://hdl.handle.net/11336/93015
identifier_str_mv Camargo, Alejandra Beatriz; Marchevsky, Eduardo Jorge; Luco, Juan Maria; QSAR study for the soybean 15-lipoxygenase inhibitory activity of organosulfur compounds derived from the essential oil of garlic; American Chemical Society; Journal of Agricultural and Food Chemistry; 55; 8; 4-2007; 3096-3103
0021-8561
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jf063020e
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jf063020e
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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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