Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark

Autores
Sgariglia, Melina Araceli; Soberon, Jose Rodolfo; Poveda Cabanes, Ana; Sampietro, Diego Alejandro; Vattuone, Marta Amelia
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Ethnopharmacological relevance Caesalpinia paraguariensis (D. Parodi) Burkart stem bark infusion (CPBI) is traditionally used in Argentina because their “vulnerary” properties. Aim of the study CPBI was studied throughout bio-guided purification procedures conducted by in vitro biological assays in order to isolate the main bioactive compounds. Material and methods Anti-inflammatory activity was assessed by enzyme inhibition assays of Hyaluronidase (Hyal) and inducible Nitric Oxide Synthase (iNOS). The antioxidant properties were evaluated by DPPH free radical scavenging assay, lipid peroxidation inhibition assay on erythrocyte membranes, and a cell-based assay that included the fluorescent probe (DCFH-DA) for indicating reactive oxygen species (ROS) generation. Bioactive compounds were purified by chromatographic methods and their structures elucidated using spectroscopic methods (ESI-MS and 1D/2D-1H/13C-NMR). Results Four main bioactive compounds were isolated from CPBI: ellagic acid (1), 3-O-methylellagic acid (2), 3,3'-di-O-methylellagic acid (3) and 3,3'-di-O-methylellagic-4-β-D-xylopyranoside (4). These were bioactive at concentrations in which are present in CPBI, being compounds 2 and 3 the best enzyme inhibitors of Hyal and iNOS, reaching the 90% inhibitory concentration (IC90) values ranging from 2.8 to 16.4 μM, that are better than that of the positive controls, aspirin (IC90: no reached) and aminoguanidine (IC90: 20.2 μM) respectively. Compounds 2 and 3 were also better scavengers for lipoperoxides than butylated hydroxytoluene (BHT), reaching the 90% effective concentration (EC90) at 1.2–4.5 μg/ml, and for DPPH radical (2.5–7.3 μg/ml); moreover compounds were able to exert its scavenging action on intracellular ROS. Structural features relevant to the biological activities are discussed. Conclusions This work provides scientific validity to the popular usage of CPBI.
Fil: Sgariglia, Melina Araceli. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; Argentina
Fil: Soberon, Jose Rodolfo. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales. Catedra de Fitoquimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; Argentina
Fil: Poveda Cabanes, Ana. Universidad Autónoma de Madrid; España
Fil: Sampietro, Diego Alejandro. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales. Catedra de Fitoquimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; Argentina
Fil: Vattuone, Marta Amelia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales. Catedra de Fitoquimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; Argentina
Materia
Caesalpinia Paraguariensis
Corteza
Antiinflamatorios
Antioxidantes
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/7166
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/7166
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem barkSgariglia, Melina AraceliSoberon, Jose RodolfoPoveda Cabanes, AnaSampietro, Diego AlejandroVattuone, Marta AmeliaCaesalpinia ParaguariensisCortezaAntiinflamatoriosAntioxidanteshttps://purl.org/becyt/ford/3.1https://purl.org/becyt/ford/3Ethnopharmacological relevance Caesalpinia paraguariensis (D. Parodi) Burkart stem bark infusion (CPBI) is traditionally used in Argentina because their “vulnerary” properties. Aim of the study CPBI was studied throughout bio-guided purification procedures conducted by in vitro biological assays in order to isolate the main bioactive compounds. Material and methods Anti-inflammatory activity was assessed by enzyme inhibition assays of Hyaluronidase (Hyal) and inducible Nitric Oxide Synthase (iNOS). The antioxidant properties were evaluated by DPPH free radical scavenging assay, lipid peroxidation inhibition assay on erythrocyte membranes, and a cell-based assay that included the fluorescent probe (DCFH-DA) for indicating reactive oxygen species (ROS) generation. Bioactive compounds were purified by chromatographic methods and their structures elucidated using spectroscopic methods (ESI-MS and 1D/2D-1H/13C-NMR). Results Four main bioactive compounds were isolated from CPBI: ellagic acid (1), 3-O-methylellagic acid (2), 3,3'-di-O-methylellagic acid (3) and 3,3'-di-O-methylellagic-4-β-D-xylopyranoside (4). These were bioactive at concentrations in which are present in CPBI, being compounds 2 and 3 the best enzyme inhibitors of Hyal and iNOS, reaching the 90% inhibitory concentration (IC90) values ranging from 2.8 to 16.4 μM, that are better than that of the positive controls, aspirin (IC90: no reached) and aminoguanidine (IC90: 20.2 μM) respectively. Compounds 2 and 3 were also better scavengers for lipoperoxides than butylated hydroxytoluene (BHT), reaching the 90% effective concentration (EC90) at 1.2–4.5 μg/ml, and for DPPH radical (2.5–7.3 μg/ml); moreover compounds were able to exert its scavenging action on intracellular ROS. Structural features relevant to the biological activities are discussed. Conclusions This work provides scientific validity to the popular usage of CPBI.Fil: Sgariglia, Melina Araceli. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; ArgentinaFil: Soberon, Jose Rodolfo. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales. Catedra de Fitoquimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; ArgentinaFil: Poveda Cabanes, Ana. Universidad Autónoma de Madrid; EspañaFil: Sampietro, Diego Alejandro. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales. Catedra de Fitoquimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; ArgentinaFil: Vattuone, Marta Amelia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales. Catedra de Fitoquimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; ArgentinaElsevier Ireland2013-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/7166Sgariglia, Melina Araceli; Soberon, Jose Rodolfo; Poveda Cabanes, Ana; Sampietro, Diego Alejandro; Vattuone, Marta Amelia; Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark; Elsevier Ireland; Journal Of Ethnopharmacology; 147; 1; 5-2013; 63-730378-8741enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0378874112008641info:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jep.2012.12.030info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:46:25Zoai:ri.conicet.gov.ar:11336/7166instacron: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 09:46:26.229CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark
title Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark
spellingShingle Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark
Sgariglia, Melina Araceli
Caesalpinia Paraguariensis
Corteza
Antiinflamatorios
Antioxidantes
title_short Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark
title_full Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark
title_fullStr Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark
title_full_unstemmed Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark
title_sort Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark
dc.creator.none.fl_str_mv Sgariglia, Melina Araceli
Soberon, Jose Rodolfo
Poveda Cabanes, Ana
Sampietro, Diego Alejandro
Vattuone, Marta Amelia
author Sgariglia, Melina Araceli
author_facet Sgariglia, Melina Araceli
Soberon, Jose Rodolfo
Poveda Cabanes, Ana
Sampietro, Diego Alejandro
Vattuone, Marta Amelia
author_role author
author2 Soberon, Jose Rodolfo
Poveda Cabanes, Ana
Sampietro, Diego Alejandro
Vattuone, Marta Amelia
author2_role author
author
author
author
dc.subject.none.fl_str_mv Caesalpinia Paraguariensis
Corteza
Antiinflamatorios
Antioxidantes
topic Caesalpinia Paraguariensis
Corteza
Antiinflamatorios
Antioxidantes
purl_subject.fl_str_mv https://purl.org/becyt/ford/3.1
https://purl.org/becyt/ford/3
dc.description.none.fl_txt_mv Ethnopharmacological relevance Caesalpinia paraguariensis (D. Parodi) Burkart stem bark infusion (CPBI) is traditionally used in Argentina because their “vulnerary” properties. Aim of the study CPBI was studied throughout bio-guided purification procedures conducted by in vitro biological assays in order to isolate the main bioactive compounds. Material and methods Anti-inflammatory activity was assessed by enzyme inhibition assays of Hyaluronidase (Hyal) and inducible Nitric Oxide Synthase (iNOS). The antioxidant properties were evaluated by DPPH free radical scavenging assay, lipid peroxidation inhibition assay on erythrocyte membranes, and a cell-based assay that included the fluorescent probe (DCFH-DA) for indicating reactive oxygen species (ROS) generation. Bioactive compounds were purified by chromatographic methods and their structures elucidated using spectroscopic methods (ESI-MS and 1D/2D-1H/13C-NMR). Results Four main bioactive compounds were isolated from CPBI: ellagic acid (1), 3-O-methylellagic acid (2), 3,3'-di-O-methylellagic acid (3) and 3,3'-di-O-methylellagic-4-β-D-xylopyranoside (4). These were bioactive at concentrations in which are present in CPBI, being compounds 2 and 3 the best enzyme inhibitors of Hyal and iNOS, reaching the 90% inhibitory concentration (IC90) values ranging from 2.8 to 16.4 μM, that are better than that of the positive controls, aspirin (IC90: no reached) and aminoguanidine (IC90: 20.2 μM) respectively. Compounds 2 and 3 were also better scavengers for lipoperoxides than butylated hydroxytoluene (BHT), reaching the 90% effective concentration (EC90) at 1.2–4.5 μg/ml, and for DPPH radical (2.5–7.3 μg/ml); moreover compounds were able to exert its scavenging action on intracellular ROS. Structural features relevant to the biological activities are discussed. Conclusions This work provides scientific validity to the popular usage of CPBI.
Fil: Sgariglia, Melina Araceli. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; Argentina
Fil: Soberon, Jose Rodolfo. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales. Catedra de Fitoquimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; Argentina
Fil: Poveda Cabanes, Ana. Universidad Autónoma de Madrid; España
Fil: Sampietro, Diego Alejandro. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales. Catedra de Fitoquimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; Argentina
Fil: Vattuone, Marta Amelia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Estudios Vegetales. Catedra de Fitoquimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán; Argentina
description Ethnopharmacological relevance Caesalpinia paraguariensis (D. Parodi) Burkart stem bark infusion (CPBI) is traditionally used in Argentina because their “vulnerary” properties. Aim of the study CPBI was studied throughout bio-guided purification procedures conducted by in vitro biological assays in order to isolate the main bioactive compounds. Material and methods Anti-inflammatory activity was assessed by enzyme inhibition assays of Hyaluronidase (Hyal) and inducible Nitric Oxide Synthase (iNOS). The antioxidant properties were evaluated by DPPH free radical scavenging assay, lipid peroxidation inhibition assay on erythrocyte membranes, and a cell-based assay that included the fluorescent probe (DCFH-DA) for indicating reactive oxygen species (ROS) generation. Bioactive compounds were purified by chromatographic methods and their structures elucidated using spectroscopic methods (ESI-MS and 1D/2D-1H/13C-NMR). Results Four main bioactive compounds were isolated from CPBI: ellagic acid (1), 3-O-methylellagic acid (2), 3,3'-di-O-methylellagic acid (3) and 3,3'-di-O-methylellagic-4-β-D-xylopyranoside (4). These were bioactive at concentrations in which are present in CPBI, being compounds 2 and 3 the best enzyme inhibitors of Hyal and iNOS, reaching the 90% inhibitory concentration (IC90) values ranging from 2.8 to 16.4 μM, that are better than that of the positive controls, aspirin (IC90: no reached) and aminoguanidine (IC90: 20.2 μM) respectively. Compounds 2 and 3 were also better scavengers for lipoperoxides than butylated hydroxytoluene (BHT), reaching the 90% effective concentration (EC90) at 1.2–4.5 μg/ml, and for DPPH radical (2.5–7.3 μg/ml); moreover compounds were able to exert its scavenging action on intracellular ROS. Structural features relevant to the biological activities are discussed. Conclusions This work provides scientific validity to the popular usage of CPBI.
publishDate 2013
dc.date.none.fl_str_mv 2013-05
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/11336/7166
Sgariglia, Melina Araceli; Soberon, Jose Rodolfo; Poveda Cabanes, Ana; Sampietro, Diego Alejandro; Vattuone, Marta Amelia; Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark; Elsevier Ireland; Journal Of Ethnopharmacology; 147; 1; 5-2013; 63-73
0378-8741
url http://hdl.handle.net/11336/7166
identifier_str_mv Sgariglia, Melina Araceli; Soberon, Jose Rodolfo; Poveda Cabanes, Ana; Sampietro, Diego Alejandro; Vattuone, Marta Amelia; Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark; Elsevier Ireland; Journal Of Ethnopharmacology; 147; 1; 5-2013; 63-73
0378-8741
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0378874112008641
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jep.2012.12.030
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
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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