Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control

Autores
Di Liberto, Melina Gabriela; Caldo, Agustín J.; Quiroga, Ariel Dario; Riveira, Martín Jorge; Derita, Marcos Gabriel
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The natural product zanthosimuline and its 18 analogues were easily prepared from simple starting materials and evaluated in vitro against postharvest fruit fungal pathogens. The panel included Penicillium digitatum, Botrytis cinerea, Monilinia fructicola, and Rhizopus stolonifer; all of them causing relevant economic losses worldwide. The minimum inhibitory concentrations and minimum fungicidal concentrations of each compound were determined, and the main structure?activity relationships were established. The biological activity observed was strongly increased by maintaining the prenyl side chain of zanthosimuline in an N-demethylated derivative. In addition, the compound that is the most active in the in vitro evaluation was tested in freshly harvested peaches exhibiting a promising brown rot control profile, comparable to the commercial agent carbendazim but demonstrating less toxicity against human liver cell lines.
Fil: Di Liberto, Melina Gabriela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Caldo, Agustín J.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Quiroga, Ariel Dario. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Fisiología Experimental. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Fisiología Experimental; Argentina
Fil: Riveira, Martín Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Derita, Marcos Gabriel. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Materia
2H-PYRANS
ALKALOIDS
POST-HARVEST
ANTIFUNGAL ACTIVITY
PEACHES
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:11336/107967
Acceder
id CONICETDig_251a72451c29623ad4a0716442924066
oai_identifier_str oai:ri.conicet.gov.ar:11336/107967
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease ControlDi Liberto, Melina GabrielaCaldo, Agustín J.Quiroga, Ariel DarioRiveira, Martín JorgeDerita, Marcos Gabriel2H-PYRANSALKALOIDSPOST-HARVESTANTIFUNGAL ACTIVITYPEACHEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The natural product zanthosimuline and its 18 analogues were easily prepared from simple starting materials and evaluated in vitro against postharvest fruit fungal pathogens. The panel included Penicillium digitatum, Botrytis cinerea, Monilinia fructicola, and Rhizopus stolonifer; all of them causing relevant economic losses worldwide. The minimum inhibitory concentrations and minimum fungicidal concentrations of each compound were determined, and the main structure?activity relationships were established. The biological activity observed was strongly increased by maintaining the prenyl side chain of zanthosimuline in an N-demethylated derivative. In addition, the compound that is the most active in the in vitro evaluation was tested in freshly harvested peaches exhibiting a promising brown rot control profile, comparable to the commercial agent carbendazim but demonstrating less toxicity against human liver cell lines.Fil: Di Liberto, Melina Gabriela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Caldo, Agustín J.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Quiroga, Ariel Dario. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Fisiología Experimental. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Fisiología Experimental; ArgentinaFil: Riveira, Martín Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Derita, Marcos Gabriel. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaAmerican Chemical Society2020-03info: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/11336/107967Di Liberto, Melina Gabriela; Caldo, Agustín J.; Quiroga, Ariel Dario; Riveira, Martín Jorge; Derita, Marcos Gabriel; Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control; American Chemical Society; ACS Omega; 5; 13; 3-2020; 7481-74872470-1343CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acsomega.0c00225info:eu-repo/semantics/altIdentifier/doi/10.1021/acsomega.0c00225info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:50:29Zoai:ri.conicet.gov.ar:11336/107967instacron: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:34982025-10-15 14:50:29.823CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control
title Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control
spellingShingle Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control
Di Liberto, Melina Gabriela
2H-PYRANS
ALKALOIDS
POST-HARVEST
ANTIFUNGAL ACTIVITY
PEACHES
title_short Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control
title_full Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control
title_fullStr Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control
title_full_unstemmed Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control
title_sort Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control
dc.creator.none.fl_str_mv Di Liberto, Melina Gabriela
Caldo, Agustín J.
Quiroga, Ariel Dario
Riveira, Martín Jorge
Derita, Marcos Gabriel
author Di Liberto, Melina Gabriela
author_facet Di Liberto, Melina Gabriela
Caldo, Agustín J.
Quiroga, Ariel Dario
Riveira, Martín Jorge
Derita, Marcos Gabriel
author_role author
author2 Caldo, Agustín J.
Quiroga, Ariel Dario
Riveira, Martín Jorge
Derita, Marcos Gabriel
author2_role author
author
author
author
dc.subject.none.fl_str_mv 2H-PYRANS
ALKALOIDS
POST-HARVEST
ANTIFUNGAL ACTIVITY
PEACHES
topic 2H-PYRANS
ALKALOIDS
POST-HARVEST
ANTIFUNGAL ACTIVITY
PEACHES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The natural product zanthosimuline and its 18 analogues were easily prepared from simple starting materials and evaluated in vitro against postharvest fruit fungal pathogens. The panel included Penicillium digitatum, Botrytis cinerea, Monilinia fructicola, and Rhizopus stolonifer; all of them causing relevant economic losses worldwide. The minimum inhibitory concentrations and minimum fungicidal concentrations of each compound were determined, and the main structure?activity relationships were established. The biological activity observed was strongly increased by maintaining the prenyl side chain of zanthosimuline in an N-demethylated derivative. In addition, the compound that is the most active in the in vitro evaluation was tested in freshly harvested peaches exhibiting a promising brown rot control profile, comparable to the commercial agent carbendazim but demonstrating less toxicity against human liver cell lines.
Fil: Di Liberto, Melina Gabriela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Caldo, Agustín J.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Quiroga, Ariel Dario. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Fisiología Experimental. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Fisiología Experimental; Argentina
Fil: Riveira, Martín Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Derita, Marcos Gabriel. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
description The natural product zanthosimuline and its 18 analogues were easily prepared from simple starting materials and evaluated in vitro against postharvest fruit fungal pathogens. The panel included Penicillium digitatum, Botrytis cinerea, Monilinia fructicola, and Rhizopus stolonifer; all of them causing relevant economic losses worldwide. The minimum inhibitory concentrations and minimum fungicidal concentrations of each compound were determined, and the main structure?activity relationships were established. The biological activity observed was strongly increased by maintaining the prenyl side chain of zanthosimuline in an N-demethylated derivative. In addition, the compound that is the most active in the in vitro evaluation was tested in freshly harvested peaches exhibiting a promising brown rot control profile, comparable to the commercial agent carbendazim but demonstrating less toxicity against human liver cell lines.
publishDate 2020
dc.date.none.fl_str_mv 2020-03
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/11336/107967
Di Liberto, Melina Gabriela; Caldo, Agustín J.; Quiroga, Ariel Dario; Riveira, Martín Jorge; Derita, Marcos Gabriel; Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control; American Chemical Society; ACS Omega; 5; 13; 3-2020; 7481-7487
2470-1343
CONICET Digital
CONICET
url http://hdl.handle.net/11336/107967
identifier_str_mv Di Liberto, Melina Gabriela; Caldo, Agustín J.; Quiroga, Ariel Dario; Riveira, Martín Jorge; Derita, Marcos Gabriel; Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control; American Chemical Society; ACS Omega; 5; 13; 3-2020; 7481-7487
2470-1343
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://pubs.acs.org/doi/10.1021/acsomega.0c00225
info:eu-repo/semantics/altIdentifier/doi/10.1021/acsomega.0c00225
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 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)
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
_version_ 1846083029781446656
score 13.22299

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