Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides

Autores
Travaini, Maria L; Sosa, Gustavo M.; Ceccarelli, Eduardo Augusto; Walter, Helmut; Cantrell, Charles L.; Carrillo, Nestor Jose; Dayan, Franck E.; Meepagala, Kumudini M.; Duke, Stephen O.
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Plants constitute a source of novel phytotoxic compounds to be explored in searching for effective and environmentally safe herbicides. From a previous screening of plant extracts for their phytotoxicity, a dichloromethane extract of Ammi visnaga (L.) Lam. was selected for further study. Phytotoxicity-guided fractionation of this extract yielded two furanochromones, khellin and visnagin, for which herbicidal activity had not been described before. Khellin and visnagin were phytotoxic to model species lettuce (Lactuca sativa) and duckweed (Lemna paucicostata), with IC50 values ranging from 110 to 175 μM. These compounds also inhibited the growth and germination of a diverse group of weeds at 0.5 and 1 mM. These weeds included five grasses [ryegrass (Lolium multiflorum), barnyardgrass (Echinocloa crus-galli), crabgrass (Digitaria sanguinalis), foxtail (Setaria italica), and millet (Panicum sp.)] and two broadleaf species [morningglory (Ipomea sp.) and velvetleaf (Abutilon theophrasti)]. During greenhouse studies visnagin was the most active and showed significant contact postemergence herbicidal activity on velvetleaf and crabgrass at 2 kg active ingredient (ai) ha-1. Moreover, its effect at 4 kg ai ha-1 was comparable to the bioherbicide pelargonic acid at the same rate. The mode of action of khellin and visnagin was not a light-dependent process. Both compounds caused membrane destabilization, photosynthetic efficiency reduction, inhibition of cell division, and cell death. These results support the potential of visnagin and, possibly, khellin as bioherbicides or lead molecules for the development of new herbicides.
Fil: Travaini, Maria L. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina. Investigaciones Biológicas en Agroquímicos Rosario S.A.; Argentina
Fil: Sosa, Gustavo M.. Investigaciones Biológicas en Agroquímicos Rosario S.A.; Argentina
Fil: Ceccarelli, Eduardo Augusto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Walter, Helmut. AgroField Consulting; Alemania
Fil: Cantrell, Charles L.. Natural Products Utilization Research Unit; Estados Unidos
Fil: Carrillo, Nestor Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Dayan, Franck E.. Natural Products Utilization Research Unit; Estados Unidos
Fil: Meepagala, Kumudini M.. Natural Products Utilization Research Unit; Estados Unidos
Fil: Duke, Stephen O.. Natural Products Utilization Research Unit; Estados Unidos
Materia
AMMI VISNAGA
BIOHERBICIDE
FURANOCHROMONE
HERBICIDE
KHELLIN
PHYTOTOXIN
VISNAGIN
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:11336/52842

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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential BioherbicidesTravaini, Maria LSosa, Gustavo M.Ceccarelli, Eduardo AugustoWalter, HelmutCantrell, Charles L.Carrillo, Nestor JoseDayan, Franck E.Meepagala, Kumudini M.Duke, Stephen O.AMMI VISNAGABIOHERBICIDEFURANOCHROMONEHERBICIDEKHELLINPHYTOTOXINVISNAGINhttps://purl.org/becyt/ford/4.4https://purl.org/becyt/ford/4Plants constitute a source of novel phytotoxic compounds to be explored in searching for effective and environmentally safe herbicides. From a previous screening of plant extracts for their phytotoxicity, a dichloromethane extract of Ammi visnaga (L.) Lam. was selected for further study. Phytotoxicity-guided fractionation of this extract yielded two furanochromones, khellin and visnagin, for which herbicidal activity had not been described before. Khellin and visnagin were phytotoxic to model species lettuce (Lactuca sativa) and duckweed (Lemna paucicostata), with IC50 values ranging from 110 to 175 μM. These compounds also inhibited the growth and germination of a diverse group of weeds at 0.5 and 1 mM. These weeds included five grasses [ryegrass (Lolium multiflorum), barnyardgrass (Echinocloa crus-galli), crabgrass (Digitaria sanguinalis), foxtail (Setaria italica), and millet (Panicum sp.)] and two broadleaf species [morningglory (Ipomea sp.) and velvetleaf (Abutilon theophrasti)]. During greenhouse studies visnagin was the most active and showed significant contact postemergence herbicidal activity on velvetleaf and crabgrass at 2 kg active ingredient (ai) ha-1. Moreover, its effect at 4 kg ai ha-1 was comparable to the bioherbicide pelargonic acid at the same rate. The mode of action of khellin and visnagin was not a light-dependent process. Both compounds caused membrane destabilization, photosynthetic efficiency reduction, inhibition of cell division, and cell death. These results support the potential of visnagin and, possibly, khellin as bioherbicides or lead molecules for the development of new herbicides.Fil: Travaini, Maria L. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina. Investigaciones Biológicas en Agroquímicos Rosario S.A.; ArgentinaFil: Sosa, Gustavo M.. Investigaciones Biológicas en Agroquímicos Rosario S.A.; ArgentinaFil: Ceccarelli, Eduardo Augusto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; ArgentinaFil: Walter, Helmut. AgroField Consulting; AlemaniaFil: Cantrell, Charles L.. Natural Products Utilization Research Unit; Estados UnidosFil: Carrillo, Nestor Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; ArgentinaFil: Dayan, Franck E.. Natural Products Utilization Research Unit; Estados UnidosFil: Meepagala, Kumudini M.. Natural Products Utilization Research Unit; Estados UnidosFil: Duke, Stephen O.. Natural Products Utilization Research Unit; Estados UnidosAmerican Chemical Society2016-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/52842Travaini, Maria L; Sosa, Gustavo M.; Ceccarelli, Eduardo Augusto; Walter, Helmut; Cantrell, Charles L.; et al.; Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides; American Chemical Society; Journal of Agricultural and Food Chemistry; 64; 50; 12-2016; 9475-94870021-8561CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.jafc.6b02462info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.jafc.6b02462info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:49:36Zoai:ri.conicet.gov.ar:11336/52842instacron: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 09:49:37.035CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides
title Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides
spellingShingle Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides
Travaini, Maria L
AMMI VISNAGA
BIOHERBICIDE
FURANOCHROMONE
HERBICIDE
KHELLIN
PHYTOTOXIN
VISNAGIN
title_short Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides
title_full Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides
title_fullStr Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides
title_full_unstemmed Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides
title_sort Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides
dc.creator.none.fl_str_mv Travaini, Maria L
Sosa, Gustavo M.
Ceccarelli, Eduardo Augusto
Walter, Helmut
Cantrell, Charles L.
Carrillo, Nestor Jose
Dayan, Franck E.
Meepagala, Kumudini M.
Duke, Stephen O.
author Travaini, Maria L
author_facet Travaini, Maria L
Sosa, Gustavo M.
Ceccarelli, Eduardo Augusto
Walter, Helmut
Cantrell, Charles L.
Carrillo, Nestor Jose
Dayan, Franck E.
Meepagala, Kumudini M.
Duke, Stephen O.
author_role author
author2 Sosa, Gustavo M.
Ceccarelli, Eduardo Augusto
Walter, Helmut
Cantrell, Charles L.
Carrillo, Nestor Jose
Dayan, Franck E.
Meepagala, Kumudini M.
Duke, Stephen O.
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv AMMI VISNAGA
BIOHERBICIDE
FURANOCHROMONE
HERBICIDE
KHELLIN
PHYTOTOXIN
VISNAGIN
topic AMMI VISNAGA
BIOHERBICIDE
FURANOCHROMONE
HERBICIDE
KHELLIN
PHYTOTOXIN
VISNAGIN
purl_subject.fl_str_mv https://purl.org/becyt/ford/4.4
https://purl.org/becyt/ford/4
dc.description.none.fl_txt_mv Plants constitute a source of novel phytotoxic compounds to be explored in searching for effective and environmentally safe herbicides. From a previous screening of plant extracts for their phytotoxicity, a dichloromethane extract of Ammi visnaga (L.) Lam. was selected for further study. Phytotoxicity-guided fractionation of this extract yielded two furanochromones, khellin and visnagin, for which herbicidal activity had not been described before. Khellin and visnagin were phytotoxic to model species lettuce (Lactuca sativa) and duckweed (Lemna paucicostata), with IC50 values ranging from 110 to 175 μM. These compounds also inhibited the growth and germination of a diverse group of weeds at 0.5 and 1 mM. These weeds included five grasses [ryegrass (Lolium multiflorum), barnyardgrass (Echinocloa crus-galli), crabgrass (Digitaria sanguinalis), foxtail (Setaria italica), and millet (Panicum sp.)] and two broadleaf species [morningglory (Ipomea sp.) and velvetleaf (Abutilon theophrasti)]. During greenhouse studies visnagin was the most active and showed significant contact postemergence herbicidal activity on velvetleaf and crabgrass at 2 kg active ingredient (ai) ha-1. Moreover, its effect at 4 kg ai ha-1 was comparable to the bioherbicide pelargonic acid at the same rate. The mode of action of khellin and visnagin was not a light-dependent process. Both compounds caused membrane destabilization, photosynthetic efficiency reduction, inhibition of cell division, and cell death. These results support the potential of visnagin and, possibly, khellin as bioherbicides or lead molecules for the development of new herbicides.
Fil: Travaini, Maria L. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina. Investigaciones Biológicas en Agroquímicos Rosario S.A.; Argentina
Fil: Sosa, Gustavo M.. Investigaciones Biológicas en Agroquímicos Rosario S.A.; Argentina
Fil: Ceccarelli, Eduardo Augusto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Walter, Helmut. AgroField Consulting; Alemania
Fil: Cantrell, Charles L.. Natural Products Utilization Research Unit; Estados Unidos
Fil: Carrillo, Nestor Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Dayan, Franck E.. Natural Products Utilization Research Unit; Estados Unidos
Fil: Meepagala, Kumudini M.. Natural Products Utilization Research Unit; Estados Unidos
Fil: Duke, Stephen O.. Natural Products Utilization Research Unit; Estados Unidos
description Plants constitute a source of novel phytotoxic compounds to be explored in searching for effective and environmentally safe herbicides. From a previous screening of plant extracts for their phytotoxicity, a dichloromethane extract of Ammi visnaga (L.) Lam. was selected for further study. Phytotoxicity-guided fractionation of this extract yielded two furanochromones, khellin and visnagin, for which herbicidal activity had not been described before. Khellin and visnagin were phytotoxic to model species lettuce (Lactuca sativa) and duckweed (Lemna paucicostata), with IC50 values ranging from 110 to 175 μM. These compounds also inhibited the growth and germination of a diverse group of weeds at 0.5 and 1 mM. These weeds included five grasses [ryegrass (Lolium multiflorum), barnyardgrass (Echinocloa crus-galli), crabgrass (Digitaria sanguinalis), foxtail (Setaria italica), and millet (Panicum sp.)] and two broadleaf species [morningglory (Ipomea sp.) and velvetleaf (Abutilon theophrasti)]. During greenhouse studies visnagin was the most active and showed significant contact postemergence herbicidal activity on velvetleaf and crabgrass at 2 kg active ingredient (ai) ha-1. Moreover, its effect at 4 kg ai ha-1 was comparable to the bioherbicide pelargonic acid at the same rate. The mode of action of khellin and visnagin was not a light-dependent process. Both compounds caused membrane destabilization, photosynthetic efficiency reduction, inhibition of cell division, and cell death. These results support the potential of visnagin and, possibly, khellin as bioherbicides or lead molecules for the development of new herbicides.
publishDate 2016
dc.date.none.fl_str_mv 2016-12
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/11336/52842
Travaini, Maria L; Sosa, Gustavo M.; Ceccarelli, Eduardo Augusto; Walter, Helmut; Cantrell, Charles L.; et al.; Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides; American Chemical Society; Journal of Agricultural and Food Chemistry; 64; 50; 12-2016; 9475-9487
0021-8561
CONICET Digital
CONICET
url http://hdl.handle.net/11336/52842
identifier_str_mv Travaini, Maria L; Sosa, Gustavo M.; Ceccarelli, Eduardo Augusto; Walter, Helmut; Cantrell, Charles L.; et al.; Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides; American Chemical Society; Journal of Agricultural and Food Chemistry; 64; 50; 12-2016; 9475-9487
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/acs.jafc.6b02462
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.jafc.6b02462
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 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)
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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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