Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae

Autores
Lima, Beatriz Viviana; Sánchez, Marianela; Agüero, María Belén; Tapia, Alejandro; Palermo, Jorge Alejandro; Feresin, Gabriela Egly
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Azorella cryptantha (Clos) Reiche, Apiaceae, vernacular name “yerba del soldado or cuerno de cabra” is a medicinal herb that grows in the Andean mountains (Argentina). An infusion or decoction of the leaves is employed as cholagogue and digestive, usually to treat food-borne illnesses associated with enterobacteria. Extracts and compounds from two Argentinean populations were subjected to antibacterial assays against pathogenic bacteria (Escherichia coli, Pseudomonas aeruginosa, Salmonella enteritidis and Yersinia enterocolitica) and Gram (+) Staphylococcus aureus methicillin-sensitive and methicillin-resistant microorganisms. The antibacterial activity-guided fractionation against a panel of ATCC and clinically isolated bacteria was done according to CLSI protocols. The petroleum ether extracts from both populations showed strong antibacterial activity against S. enteritidis with MIC values from 125 to 250 μg/ml, and also towards methicillin-sensitive Staphylococcus aureus, and Gram negative strains E. coli, P. aeruginosa, Salmonella sp. and Yersinia enterocolítica-PI, (MICs between 400 and 1000 μg/ml). Fractions from the petroleum extracts showed strong antimicrobial activity, against Escherichia coli ATCC 25922, E. coli-LM1, E. coli-LM2, and Salmonella enteritidis-MI, with MICs values between 31.2 and 125 μg/ml. The bioassay-guided fractionation of the petroleum ether extracts led to the isolation of nine terpenes: azorellolide (1), mulinol (2), stachytriol (3),1α,10β,4β,5α-diepoxy-7β-germacran-6β-ol (4), 1β,10α,4β,5α-diepoxy-7β-germacran-6β-ol (5), 1,2,3,3α,4,5,6,7,8,8α-decahydro-7-(1-hydroxy-1-methylethyl)-1,4-dimethylazulene-3α,8α-diol (6), madreporanone (7), yaretol (8) and chrysotol or 6β,10β-epoxy-4α-hydroxyguaiane (9). Compounds 3, 5, 6 and 9 are reported here for the first time from A. cryptantha. Their structures and relative configurations have been determinated by means 1D and 2D NMR techniques. Chrysothol (9), madreporanone (7), and stachytriol (3) showed strong antimicrobial activities (MICs = 50–100 μg/ml) against enterobacteria E. coli and S. enteritidis. The antibacterial activity found for some of the isolated compounds supports least in part, the commercial exploited of this species to treat food-borne illnesses associated with Gram negative pathogenic bacteria.
Fil: Lima, Beatriz Viviana. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Sánchez, Marianela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados A la Química Orgánica (i); Argentina; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Agüero, María Belén. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Tapia, Alejandro. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Palermo, Jorge Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados A la Química Orgánica (i); Argentina; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Feresin, Gabriela Egly. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Materia
Azorella Cryptantha
Antibacterial Activity
Chrysothol
Madreporanone
Stachytriol
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:11336/15327
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/15327
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network_name_str CONICET Digital (CONICET)
spelling Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, ApiaceaeLima, Beatriz VivianaSánchez, MarianelaAgüero, María BelénTapia, AlejandroPalermo, Jorge AlejandroFeresin, Gabriela EglyAzorella CryptanthaAntibacterial ActivityChrysotholMadreporanoneStachytriolhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Azorella cryptantha (Clos) Reiche, Apiaceae, vernacular name “yerba del soldado or cuerno de cabra” is a medicinal herb that grows in the Andean mountains (Argentina). An infusion or decoction of the leaves is employed as cholagogue and digestive, usually to treat food-borne illnesses associated with enterobacteria. Extracts and compounds from two Argentinean populations were subjected to antibacterial assays against pathogenic bacteria (Escherichia coli, Pseudomonas aeruginosa, Salmonella enteritidis and Yersinia enterocolitica) and Gram (+) Staphylococcus aureus methicillin-sensitive and methicillin-resistant microorganisms. The antibacterial activity-guided fractionation against a panel of ATCC and clinically isolated bacteria was done according to CLSI protocols. The petroleum ether extracts from both populations showed strong antibacterial activity against S. enteritidis with MIC values from 125 to 250 μg/ml, and also towards methicillin-sensitive Staphylococcus aureus, and Gram negative strains E. coli, P. aeruginosa, Salmonella sp. and Yersinia enterocolítica-PI, (MICs between 400 and 1000 μg/ml). Fractions from the petroleum extracts showed strong antimicrobial activity, against Escherichia coli ATCC 25922, E. coli-LM1, E. coli-LM2, and Salmonella enteritidis-MI, with MICs values between 31.2 and 125 μg/ml. The bioassay-guided fractionation of the petroleum ether extracts led to the isolation of nine terpenes: azorellolide (1), mulinol (2), stachytriol (3),1α,10β,4β,5α-diepoxy-7β-germacran-6β-ol (4), 1β,10α,4β,5α-diepoxy-7β-germacran-6β-ol (5), 1,2,3,3α,4,5,6,7,8,8α-decahydro-7-(1-hydroxy-1-methylethyl)-1,4-dimethylazulene-3α,8α-diol (6), madreporanone (7), yaretol (8) and chrysotol or 6β,10β-epoxy-4α-hydroxyguaiane (9). Compounds 3, 5, 6 and 9 are reported here for the first time from A. cryptantha. Their structures and relative configurations have been determinated by means 1D and 2D NMR techniques. Chrysothol (9), madreporanone (7), and stachytriol (3) showed strong antimicrobial activities (MICs = 50–100 μg/ml) against enterobacteria E. coli and S. enteritidis. The antibacterial activity found for some of the isolated compounds supports least in part, the commercial exploited of this species to treat food-borne illnesses associated with Gram negative pathogenic bacteria.Fil: Lima, Beatriz Viviana. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; ArgentinaFil: Sánchez, Marianela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados A la Química Orgánica (i); Argentina; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; ArgentinaFil: Agüero, María Belén. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; ArgentinaFil: Tapia, Alejandro. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; ArgentinaFil: Palermo, Jorge Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados A la Química Orgánica (i); Argentina; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; ArgentinaFil: Feresin, Gabriela Egly. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; ArgentinaElsevier2015-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/15327Lima, Beatriz Viviana; Sánchez, Marianela; Agüero, María Belén; Tapia, Alejandro; Palermo, Jorge Alejandro; et al.; Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae; Elsevier; Industrial Crops And Products; 64; 1-2015; 152-1570926-6690enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0926669014006839info:eu-repo/semantics/altIdentifier/doi/10.1016/j.indcrop.2014.10.065info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:05:00Zoai:ri.conicet.gov.ar:11336/15327instacron: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 10:05:00.864CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae
title Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae
spellingShingle Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae
Lima, Beatriz Viviana
Azorella Cryptantha
Antibacterial Activity
Chrysothol
Madreporanone
Stachytriol
title_short Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae
title_full Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae
title_fullStr Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae
title_full_unstemmed Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae
title_sort Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae
dc.creator.none.fl_str_mv Lima, Beatriz Viviana
Sánchez, Marianela
Agüero, María Belén
Tapia, Alejandro
Palermo, Jorge Alejandro
Feresin, Gabriela Egly
author Lima, Beatriz Viviana
author_facet Lima, Beatriz Viviana
Sánchez, Marianela
Agüero, María Belén
Tapia, Alejandro
Palermo, Jorge Alejandro
Feresin, Gabriela Egly
author_role author
author2 Sánchez, Marianela
Agüero, María Belén
Tapia, Alejandro
Palermo, Jorge Alejandro
Feresin, Gabriela Egly
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Azorella Cryptantha
Antibacterial Activity
Chrysothol
Madreporanone
Stachytriol
topic Azorella Cryptantha
Antibacterial Activity
Chrysothol
Madreporanone
Stachytriol
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Azorella cryptantha (Clos) Reiche, Apiaceae, vernacular name “yerba del soldado or cuerno de cabra” is a medicinal herb that grows in the Andean mountains (Argentina). An infusion or decoction of the leaves is employed as cholagogue and digestive, usually to treat food-borne illnesses associated with enterobacteria. Extracts and compounds from two Argentinean populations were subjected to antibacterial assays against pathogenic bacteria (Escherichia coli, Pseudomonas aeruginosa, Salmonella enteritidis and Yersinia enterocolitica) and Gram (+) Staphylococcus aureus methicillin-sensitive and methicillin-resistant microorganisms. The antibacterial activity-guided fractionation against a panel of ATCC and clinically isolated bacteria was done according to CLSI protocols. The petroleum ether extracts from both populations showed strong antibacterial activity against S. enteritidis with MIC values from 125 to 250 μg/ml, and also towards methicillin-sensitive Staphylococcus aureus, and Gram negative strains E. coli, P. aeruginosa, Salmonella sp. and Yersinia enterocolítica-PI, (MICs between 400 and 1000 μg/ml). Fractions from the petroleum extracts showed strong antimicrobial activity, against Escherichia coli ATCC 25922, E. coli-LM1, E. coli-LM2, and Salmonella enteritidis-MI, with MICs values between 31.2 and 125 μg/ml. The bioassay-guided fractionation of the petroleum ether extracts led to the isolation of nine terpenes: azorellolide (1), mulinol (2), stachytriol (3),1α,10β,4β,5α-diepoxy-7β-germacran-6β-ol (4), 1β,10α,4β,5α-diepoxy-7β-germacran-6β-ol (5), 1,2,3,3α,4,5,6,7,8,8α-decahydro-7-(1-hydroxy-1-methylethyl)-1,4-dimethylazulene-3α,8α-diol (6), madreporanone (7), yaretol (8) and chrysotol or 6β,10β-epoxy-4α-hydroxyguaiane (9). Compounds 3, 5, 6 and 9 are reported here for the first time from A. cryptantha. Their structures and relative configurations have been determinated by means 1D and 2D NMR techniques. Chrysothol (9), madreporanone (7), and stachytriol (3) showed strong antimicrobial activities (MICs = 50–100 μg/ml) against enterobacteria E. coli and S. enteritidis. The antibacterial activity found for some of the isolated compounds supports least in part, the commercial exploited of this species to treat food-borne illnesses associated with Gram negative pathogenic bacteria.
Fil: Lima, Beatriz Viviana. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Sánchez, Marianela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados A la Química Orgánica (i); Argentina; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Agüero, María Belén. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Tapia, Alejandro. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Palermo, Jorge Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados A la Química Orgánica (i); Argentina; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Feresin, Gabriela Egly. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
description Azorella cryptantha (Clos) Reiche, Apiaceae, vernacular name “yerba del soldado or cuerno de cabra” is a medicinal herb that grows in the Andean mountains (Argentina). An infusion or decoction of the leaves is employed as cholagogue and digestive, usually to treat food-borne illnesses associated with enterobacteria. Extracts and compounds from two Argentinean populations were subjected to antibacterial assays against pathogenic bacteria (Escherichia coli, Pseudomonas aeruginosa, Salmonella enteritidis and Yersinia enterocolitica) and Gram (+) Staphylococcus aureus methicillin-sensitive and methicillin-resistant microorganisms. The antibacterial activity-guided fractionation against a panel of ATCC and clinically isolated bacteria was done according to CLSI protocols. The petroleum ether extracts from both populations showed strong antibacterial activity against S. enteritidis with MIC values from 125 to 250 μg/ml, and also towards methicillin-sensitive Staphylococcus aureus, and Gram negative strains E. coli, P. aeruginosa, Salmonella sp. and Yersinia enterocolítica-PI, (MICs between 400 and 1000 μg/ml). Fractions from the petroleum extracts showed strong antimicrobial activity, against Escherichia coli ATCC 25922, E. coli-LM1, E. coli-LM2, and Salmonella enteritidis-MI, with MICs values between 31.2 and 125 μg/ml. The bioassay-guided fractionation of the petroleum ether extracts led to the isolation of nine terpenes: azorellolide (1), mulinol (2), stachytriol (3),1α,10β,4β,5α-diepoxy-7β-germacran-6β-ol (4), 1β,10α,4β,5α-diepoxy-7β-germacran-6β-ol (5), 1,2,3,3α,4,5,6,7,8,8α-decahydro-7-(1-hydroxy-1-methylethyl)-1,4-dimethylazulene-3α,8α-diol (6), madreporanone (7), yaretol (8) and chrysotol or 6β,10β-epoxy-4α-hydroxyguaiane (9). Compounds 3, 5, 6 and 9 are reported here for the first time from A. cryptantha. Their structures and relative configurations have been determinated by means 1D and 2D NMR techniques. Chrysothol (9), madreporanone (7), and stachytriol (3) showed strong antimicrobial activities (MICs = 50–100 μg/ml) against enterobacteria E. coli and S. enteritidis. The antibacterial activity found for some of the isolated compounds supports least in part, the commercial exploited of this species to treat food-borne illnesses associated with Gram negative pathogenic bacteria.
publishDate 2015
dc.date.none.fl_str_mv 2015-01
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/11336/15327
Lima, Beatriz Viviana; Sánchez, Marianela; Agüero, María Belén; Tapia, Alejandro; Palermo, Jorge Alejandro; et al.; Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae; Elsevier; Industrial Crops And Products; 64; 1-2015; 152-157
0926-6690
url http://hdl.handle.net/11336/15327
identifier_str_mv Lima, Beatriz Viviana; Sánchez, Marianela; Agüero, María Belén; Tapia, Alejandro; Palermo, Jorge Alejandro; et al.; Antibacterial activity of extracts and compounds isolated from the Andean medicinal plant Azorella cryptantha (Clos) Reiche, Apiaceae; Elsevier; Industrial Crops And Products; 64; 1-2015; 152-157
0926-6690
dc.language.none.fl_str_mv eng
language eng
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info:eu-repo/semantics/altIdentifier/doi/10.1016/j.indcrop.2014.10.065
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dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
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reponame_str CONICET Digital (CONICET)
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instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
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repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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