Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7

Autores
Paz, Cristian; González Chavarría, Iván; Freire Espeleta, Eleonora; Ortiz, Leandro; Karpiński, Tomasz M.; Duprat, Felix; Baggio, Ricardo Fortunato
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Azara dentata Ruiz & Pav. also called “Corcolen” is an endemic shrub of Chile. The honey produced in areas with abundance of Azara dentata is highly appreciate by its polyphenols. In the present work, we isolated and identified for the first time the phytochemical components of Azara dentata and its cytotoxic effects were analyzed on cancer cells together with its antimicrobial activity. The results showed that palmitic acid methyl ester, linolenic acid methyl ester, α-tocopherol and β-sitosterol are the main non-polar constituents of the plant, while the compounds AD-3 (3-phenylisocoumarin, 0.0001% yield) and AD-4 (methyl 2-phenacyl-benzoate, 0.00039% yield) were isolated by column chromatography with n-hexane/EtOAc (3:2 v/v) and their structures were determined using NMR analysis. In addition, the structure of AD-4 was complemented by a single crystal x-ray structural determination. Azara dentata showed moderate antibacterial activity against S. aureus and S. epidermidis with a MIC of 5.0 and 10 mg/mL respectively. The cytotoxic activity of Azara dentata against MCF-7 cancer cells showed an IC50 of 15.63 µg/mL, this is a promissory value for the deeper study of its metabolites in cancer models.
Fil: Paz, Cristian. Universidad de La Frontera; Chile
Fil: González Chavarría, Iván. Universidad de Concepción; Chile
Fil: Freire Espeleta, Eleonora. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigaciones y Aplicaciones no Nucleares. Gerencia de Física (Centro Atómico Constituyentes); Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Ortiz, Leandro. Universidad Austral de Chile; Chile
Fil: Karpiński, Tomasz M.. Poznan University Of Medical Sciences; Polonia
Fil: Duprat, Felix. Universidad de Concepción; Chile
Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigaciones y Aplicaciones no Nucleares. Gerencia de Física (Centro Atómico Constituyentes); Argentina
Materia
ANTIMICROBIAL ACTIVITY
AZARA DENTATA
CYTOTOXIC ACTIVITY
GC-MS
PHYTOCHEMICALS
X-RAY DIFFRACTION
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:11336/169817
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/169817
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7Paz, CristianGonzález Chavarría, IvánFreire Espeleta, EleonoraOrtiz, LeandroKarpiński, Tomasz M.Duprat, FelixBaggio, Ricardo FortunatoANTIMICROBIAL ACTIVITYAZARA DENTATACYTOTOXIC ACTIVITYGC-MSPHYTOCHEMICALSX-RAY DIFFRACTIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Azara dentata Ruiz & Pav. also called “Corcolen” is an endemic shrub of Chile. The honey produced in areas with abundance of Azara dentata is highly appreciate by its polyphenols. In the present work, we isolated and identified for the first time the phytochemical components of Azara dentata and its cytotoxic effects were analyzed on cancer cells together with its antimicrobial activity. The results showed that palmitic acid methyl ester, linolenic acid methyl ester, α-tocopherol and β-sitosterol are the main non-polar constituents of the plant, while the compounds AD-3 (3-phenylisocoumarin, 0.0001% yield) and AD-4 (methyl 2-phenacyl-benzoate, 0.00039% yield) were isolated by column chromatography with n-hexane/EtOAc (3:2 v/v) and their structures were determined using NMR analysis. In addition, the structure of AD-4 was complemented by a single crystal x-ray structural determination. Azara dentata showed moderate antibacterial activity against S. aureus and S. epidermidis with a MIC of 5.0 and 10 mg/mL respectively. The cytotoxic activity of Azara dentata against MCF-7 cancer cells showed an IC50 of 15.63 µg/mL, this is a promissory value for the deeper study of its metabolites in cancer models.Fil: Paz, Cristian. Universidad de La Frontera; ChileFil: González Chavarría, Iván. Universidad de Concepción; ChileFil: Freire Espeleta, Eleonora. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigaciones y Aplicaciones no Nucleares. Gerencia de Física (Centro Atómico Constituyentes); Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Ortiz, Leandro. Universidad Austral de Chile; ChileFil: Karpiński, Tomasz M.. Poznan University Of Medical Sciences; PoloniaFil: Duprat, Felix. Universidad de Concepción; ChileFil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigaciones y Aplicaciones no Nucleares. Gerencia de Física (Centro Atómico Constituyentes); ArgentinaSociedad Chilena de Química2020-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/169817Paz, Cristian; González Chavarría, Iván; Freire Espeleta, Eleonora; Ortiz, Leandro; Karpiński, Tomasz M.; et al.; Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7; Sociedad Chilena de Química; Journal of the Chilean Chemical Society; 65; 3; 9-2020; 4891-48940717-93240717-9707CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://jcchems.com/index.php/JCCHEMS/article/view/1532info:eu-repo/semantics/altIdentifier/doi/10.4067/s0717-97072020000204891info:eu-repo/semantics/altIdentifier/url/https://www.scielo.cl/scielo.php?pid=S0717-97072020000304891&script=sci_arttextinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:22:12Zoai:ri.conicet.gov.ar:11336/169817instacron: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 10:22:12.704CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7
title Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7
spellingShingle Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7
Paz, Cristian
ANTIMICROBIAL ACTIVITY
AZARA DENTATA
CYTOTOXIC ACTIVITY
GC-MS
PHYTOCHEMICALS
X-RAY DIFFRACTION
title_short Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7
title_full Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7
title_fullStr Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7
title_full_unstemmed Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7
title_sort Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7
dc.creator.none.fl_str_mv Paz, Cristian
González Chavarría, Iván
Freire Espeleta, Eleonora
Ortiz, Leandro
Karpiński, Tomasz M.
Duprat, Felix
Baggio, Ricardo Fortunato
author Paz, Cristian
author_facet Paz, Cristian
González Chavarría, Iván
Freire Espeleta, Eleonora
Ortiz, Leandro
Karpiński, Tomasz M.
Duprat, Felix
Baggio, Ricardo Fortunato
author_role author
author2 González Chavarría, Iván
Freire Espeleta, Eleonora
Ortiz, Leandro
Karpiński, Tomasz M.
Duprat, Felix
Baggio, Ricardo Fortunato
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIMICROBIAL ACTIVITY
AZARA DENTATA
CYTOTOXIC ACTIVITY
GC-MS
PHYTOCHEMICALS
X-RAY DIFFRACTION
topic ANTIMICROBIAL ACTIVITY
AZARA DENTATA
CYTOTOXIC ACTIVITY
GC-MS
PHYTOCHEMICALS
X-RAY DIFFRACTION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Azara dentata Ruiz & Pav. also called “Corcolen” is an endemic shrub of Chile. The honey produced in areas with abundance of Azara dentata is highly appreciate by its polyphenols. In the present work, we isolated and identified for the first time the phytochemical components of Azara dentata and its cytotoxic effects were analyzed on cancer cells together with its antimicrobial activity. The results showed that palmitic acid methyl ester, linolenic acid methyl ester, α-tocopherol and β-sitosterol are the main non-polar constituents of the plant, while the compounds AD-3 (3-phenylisocoumarin, 0.0001% yield) and AD-4 (methyl 2-phenacyl-benzoate, 0.00039% yield) were isolated by column chromatography with n-hexane/EtOAc (3:2 v/v) and their structures were determined using NMR analysis. In addition, the structure of AD-4 was complemented by a single crystal x-ray structural determination. Azara dentata showed moderate antibacterial activity against S. aureus and S. epidermidis with a MIC of 5.0 and 10 mg/mL respectively. The cytotoxic activity of Azara dentata against MCF-7 cancer cells showed an IC50 of 15.63 µg/mL, this is a promissory value for the deeper study of its metabolites in cancer models.
Fil: Paz, Cristian. Universidad de La Frontera; Chile
Fil: González Chavarría, Iván. Universidad de Concepción; Chile
Fil: Freire Espeleta, Eleonora. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigaciones y Aplicaciones no Nucleares. Gerencia de Física (Centro Atómico Constituyentes); Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Ortiz, Leandro. Universidad Austral de Chile; Chile
Fil: Karpiński, Tomasz M.. Poznan University Of Medical Sciences; Polonia
Fil: Duprat, Felix. Universidad de Concepción; Chile
Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Gerencia del Área de Investigaciones y Aplicaciones no Nucleares. Gerencia de Física (Centro Atómico Constituyentes); Argentina
description Azara dentata Ruiz & Pav. also called “Corcolen” is an endemic shrub of Chile. The honey produced in areas with abundance of Azara dentata is highly appreciate by its polyphenols. In the present work, we isolated and identified for the first time the phytochemical components of Azara dentata and its cytotoxic effects were analyzed on cancer cells together with its antimicrobial activity. The results showed that palmitic acid methyl ester, linolenic acid methyl ester, α-tocopherol and β-sitosterol are the main non-polar constituents of the plant, while the compounds AD-3 (3-phenylisocoumarin, 0.0001% yield) and AD-4 (methyl 2-phenacyl-benzoate, 0.00039% yield) were isolated by column chromatography with n-hexane/EtOAc (3:2 v/v) and their structures were determined using NMR analysis. In addition, the structure of AD-4 was complemented by a single crystal x-ray structural determination. Azara dentata showed moderate antibacterial activity against S. aureus and S. epidermidis with a MIC of 5.0 and 10 mg/mL respectively. The cytotoxic activity of Azara dentata against MCF-7 cancer cells showed an IC50 of 15.63 µg/mL, this is a promissory value for the deeper study of its metabolites in cancer models.
publishDate 2020
dc.date.none.fl_str_mv 2020-09
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/11336/169817
Paz, Cristian; González Chavarría, Iván; Freire Espeleta, Eleonora; Ortiz, Leandro; Karpiński, Tomasz M.; et al.; Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7; Sociedad Chilena de Química; Journal of the Chilean Chemical Society; 65; 3; 9-2020; 4891-4894
0717-9324
0717-9707
CONICET Digital
CONICET
url http://hdl.handle.net/11336/169817
identifier_str_mv Paz, Cristian; González Chavarría, Iván; Freire Espeleta, Eleonora; Ortiz, Leandro; Karpiński, Tomasz M.; et al.; Phytochemical and crystallographic studies of Azara dentata extracts and its cytotoxic effects on human breast cancer cell, MCF-7; Sociedad Chilena de Química; Journal of the Chilean Chemical Society; 65; 3; 9-2020; 4891-4894
0717-9324
0717-9707
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://jcchems.com/index.php/JCCHEMS/article/view/1532
info:eu-repo/semantics/altIdentifier/doi/10.4067/s0717-97072020000204891
info:eu-repo/semantics/altIdentifier/url/https://www.scielo.cl/scielo.php?pid=S0717-97072020000304891&script=sci_arttext
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
dc.publisher.none.fl_str_mv Sociedad Chilena de Química
publisher.none.fl_str_mv Sociedad Chilena de Química
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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