Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron

Autores
Bravetti, Margarita María del Milagro; Vico, Raquel Viviana; Carpinella, Maria Cecilia; Ferrayoli, Carlos Guillermo; Palacios, Sara Maria
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Bioguided isolation of the EtOH extract from the medicinal native plant, Ophryosporus charua, against Raphanus sativus, yielded three phenylpropanoids, charuol A [(Z)-4-((1S,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate], charuepoxide [(Z)-4-((2S,3R)-3-(acetoxymethyl oxiran-2-yl)phenyl) 2-methylbut-2-enoate] and charuol B [(Z)-4-((1R,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate]. Their structures and absolute configuration were established by extensive spectroscopic analyses. The effective concentrations for 50% inhibition of germination (ECg50) and root (ECr50) and shoot (ECs50) elongations were determined for these compounds against P. miliaceum (monocot) and Raphanus sativus (dicot). Charuol A was the most active in the inhibition of germination of P. miliaceum (ECg50 = 0.97 mM), followed by charuol B and charuepoxide, although charuol B was the most effective in regulating the root growth of P. miliaceum seedlings, with an ECr50 of 1.0 mM. Charuol A inhibited the germination of R. sativus, while its seedling development was also affected by all three compounds with different effectiveness. Charuol A was also highly effective in the 0.09–0.30 mM range against other test species such as Lactuca sativa, Eruca sativa, Allium ampeloprasum and Secale cereale.
Fil: Bravetti, Margarita María del Milagro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Católica de Córdoba; Argentina
Fil: Vico, Raquel Viviana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Carpinella, Maria Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Católica de Córdoba; Argentina
Fil: Ferrayoli, Carlos Guillermo. Provincia de Córdoba. Ministerio de Ciencia y Técnica. Centro de Excelencia en Productos y Procesos de Córdoba; Argentina
Fil: Palacios, Sara Maria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Católica de Córdoba; Argentina
Materia
Asteraceae
Germination Inhibition
Growth Inhibition
Lactuca Sativa
Ophryosporus Charua
Panicum Miliaceum
Phenylpropanoids
Raphanus Sativus
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:11336/64060
Acceder
id CONICETDig_3e2d2e52c1c2bfbf11d79e4dfa062720
oai_identifier_str oai:ri.conicet.gov.ar:11336/64060
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) HieronBravetti, Margarita María del MilagroVico, Raquel VivianaCarpinella, Maria CeciliaFerrayoli, Carlos GuillermoPalacios, Sara MariaAsteraceaeGermination InhibitionGrowth InhibitionLactuca SativaOphryosporus CharuaPanicum MiliaceumPhenylpropanoidsRaphanus Sativushttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Bioguided isolation of the EtOH extract from the medicinal native plant, Ophryosporus charua, against Raphanus sativus, yielded three phenylpropanoids, charuol A [(Z)-4-((1S,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate], charuepoxide [(Z)-4-((2S,3R)-3-(acetoxymethyl oxiran-2-yl)phenyl) 2-methylbut-2-enoate] and charuol B [(Z)-4-((1R,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate]. Their structures and absolute configuration were established by extensive spectroscopic analyses. The effective concentrations for 50% inhibition of germination (ECg50) and root (ECr50) and shoot (ECs50) elongations were determined for these compounds against P. miliaceum (monocot) and Raphanus sativus (dicot). Charuol A was the most active in the inhibition of germination of P. miliaceum (ECg50 = 0.97 mM), followed by charuol B and charuepoxide, although charuol B was the most effective in regulating the root growth of P. miliaceum seedlings, with an ECr50 of 1.0 mM. Charuol A inhibited the germination of R. sativus, while its seedling development was also affected by all three compounds with different effectiveness. Charuol A was also highly effective in the 0.09–0.30 mM range against other test species such as Lactuca sativa, Eruca sativa, Allium ampeloprasum and Secale cereale.Fil: Bravetti, Margarita María del Milagro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Católica de Córdoba; ArgentinaFil: Vico, Raquel Viviana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Carpinella, Maria Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Católica de Córdoba; ArgentinaFil: Ferrayoli, Carlos Guillermo. Provincia de Córdoba. Ministerio de Ciencia y Técnica. Centro de Excelencia en Productos y Procesos de Córdoba; ArgentinaFil: Palacios, Sara Maria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Católica de Córdoba; ArgentinaPergamon-Elsevier Science Ltd2017-06info: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/11336/64060Bravetti, Margarita María del Milagro; Vico, Raquel Viviana; Carpinella, Maria Cecilia; Ferrayoli, Carlos Guillermo; Palacios, Sara Maria; Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron; Pergamon-Elsevier Science Ltd; Phytochemistry; 138; 6-2017; 145-1510031-9422CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0031942217300961info:eu-repo/semantics/altIdentifier/doi/10.1016/j.phytochem.2017.02.025info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:33:35Zoai:ri.conicet.gov.ar:11336/64060instacron: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 09:33:35.359CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron
title Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron
spellingShingle Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron
Bravetti, Margarita María del Milagro
Asteraceae
Germination Inhibition
Growth Inhibition
Lactuca Sativa
Ophryosporus Charua
Panicum Miliaceum
Phenylpropanoids
Raphanus Sativus
title_short Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron
title_full Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron
title_fullStr Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron
title_full_unstemmed Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron
title_sort Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron
dc.creator.none.fl_str_mv Bravetti, Margarita María del Milagro
Vico, Raquel Viviana
Carpinella, Maria Cecilia
Ferrayoli, Carlos Guillermo
Palacios, Sara Maria
author Bravetti, Margarita María del Milagro
author_facet Bravetti, Margarita María del Milagro
Vico, Raquel Viviana
Carpinella, Maria Cecilia
Ferrayoli, Carlos Guillermo
Palacios, Sara Maria
author_role author
author2 Vico, Raquel Viviana
Carpinella, Maria Cecilia
Ferrayoli, Carlos Guillermo
Palacios, Sara Maria
author2_role author
author
author
author
dc.subject.none.fl_str_mv Asteraceae
Germination Inhibition
Growth Inhibition
Lactuca Sativa
Ophryosporus Charua
Panicum Miliaceum
Phenylpropanoids
Raphanus Sativus
topic Asteraceae
Germination Inhibition
Growth Inhibition
Lactuca Sativa
Ophryosporus Charua
Panicum Miliaceum
Phenylpropanoids
Raphanus Sativus
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Bioguided isolation of the EtOH extract from the medicinal native plant, Ophryosporus charua, against Raphanus sativus, yielded three phenylpropanoids, charuol A [(Z)-4-((1S,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate], charuepoxide [(Z)-4-((2S,3R)-3-(acetoxymethyl oxiran-2-yl)phenyl) 2-methylbut-2-enoate] and charuol B [(Z)-4-((1R,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate]. Their structures and absolute configuration were established by extensive spectroscopic analyses. The effective concentrations for 50% inhibition of germination (ECg50) and root (ECr50) and shoot (ECs50) elongations were determined for these compounds against P. miliaceum (monocot) and Raphanus sativus (dicot). Charuol A was the most active in the inhibition of germination of P. miliaceum (ECg50 = 0.97 mM), followed by charuol B and charuepoxide, although charuol B was the most effective in regulating the root growth of P. miliaceum seedlings, with an ECr50 of 1.0 mM. Charuol A inhibited the germination of R. sativus, while its seedling development was also affected by all three compounds with different effectiveness. Charuol A was also highly effective in the 0.09–0.30 mM range against other test species such as Lactuca sativa, Eruca sativa, Allium ampeloprasum and Secale cereale.
Fil: Bravetti, Margarita María del Milagro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Católica de Córdoba; Argentina
Fil: Vico, Raquel Viviana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Carpinella, Maria Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Católica de Córdoba; Argentina
Fil: Ferrayoli, Carlos Guillermo. Provincia de Córdoba. Ministerio de Ciencia y Técnica. Centro de Excelencia en Productos y Procesos de Córdoba; Argentina
Fil: Palacios, Sara Maria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Católica de Córdoba; Argentina
description Bioguided isolation of the EtOH extract from the medicinal native plant, Ophryosporus charua, against Raphanus sativus, yielded three phenylpropanoids, charuol A [(Z)-4-((1S,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate], charuepoxide [(Z)-4-((2S,3R)-3-(acetoxymethyl oxiran-2-yl)phenyl) 2-methylbut-2-enoate] and charuol B [(Z)-4-((1R,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate]. Their structures and absolute configuration were established by extensive spectroscopic analyses. The effective concentrations for 50% inhibition of germination (ECg50) and root (ECr50) and shoot (ECs50) elongations were determined for these compounds against P. miliaceum (monocot) and Raphanus sativus (dicot). Charuol A was the most active in the inhibition of germination of P. miliaceum (ECg50 = 0.97 mM), followed by charuol B and charuepoxide, although charuol B was the most effective in regulating the root growth of P. miliaceum seedlings, with an ECr50 of 1.0 mM. Charuol A inhibited the germination of R. sativus, while its seedling development was also affected by all three compounds with different effectiveness. Charuol A was also highly effective in the 0.09–0.30 mM range against other test species such as Lactuca sativa, Eruca sativa, Allium ampeloprasum and Secale cereale.
publishDate 2017
dc.date.none.fl_str_mv 2017-06
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/11336/64060
Bravetti, Margarita María del Milagro; Vico, Raquel Viviana; Carpinella, Maria Cecilia; Ferrayoli, Carlos Guillermo; Palacios, Sara Maria; Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron; Pergamon-Elsevier Science Ltd; Phytochemistry; 138; 6-2017; 145-151
0031-9422
CONICET Digital
CONICET
url http://hdl.handle.net/11336/64060
identifier_str_mv Bravetti, Margarita María del Milagro; Vico, Raquel Viviana; Carpinella, Maria Cecilia; Ferrayoli, Carlos Guillermo; Palacios, Sara Maria; Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron; Pergamon-Elsevier Science Ltd; Phytochemistry; 138; 6-2017; 145-151
0031-9422
CONICET Digital
CONICET
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/S0031942217300961
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.phytochem.2017.02.025
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 Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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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