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

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 causin...

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Autores principales:	Di Liberto, Melina G., Caldo, Agustín J., Quiroga, Ariel Darío, Riveira, Martín Jorge, Derita, Marcos G.
Formato:	article artículo publishedVersion
Lenguaje:	Inglés
Publicado:	American Chemical Society 2021
Materias:	Infectious diseases Antimicrobial agents Reaction products Solvents Organic compounds
Acceso en línea:	http://hdl.handle.net/2133/21775 http://hdl.handle.net/2133/21775
Aporte de:	Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario

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spelling	I15-R121-2133-217752023-05-12T17:08:18Z Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control Di Liberto, Melina G. Caldo, Agustín J. Quiroga, Ariel Darío Riveira, Martín Jorge Derita, Marcos G. Infectious diseases Antimicrobial agents Reaction products Solvents Organic compounds 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 G. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Farmacognosia; Argentina. Fil: Caldo, Agustín J. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. Fil: Quiroga, Ariel D. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Fisiología Experimental (IFISE-CONICET); Argentina. Fil: Riveira, Martín Jorge. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. Fil: Derita, Marcos G. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Farmacognosia; Argentina. Fil: Derita, Marcos G. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias. Instituto de Ciencias Agropecuarias del Litoral (ICiAgro Litoral-CONICET); Argentina. 2021-08-26T21:10:05Z 2021-08-26T21:10:05Z 2020 2021-08-26T21:10:05Z 2021-08-26T21:10:05Z 2020 article artículo publishedVersion 2470-1343 http://hdl.handle.net/2133/21775 http://hdl.handle.net/2133/21775 eng https://pubs.acs.org/doi/10.1021/acsomega.0c00225# https://doi.org/10.1021/acsomega.0c00225 http://creativecommons.org/licenses/by-nc-sa/2.5/ar/ Di Liberto, Melina G. Caldo, Agustín J. Quiroga, Ariel D. Riveira, Martín Jorge Derita, Marcos G. Atribución-NoComercial-CompartirIgual openAccess application/pdf American Chemical Society
institution	Universidad Nacional de Rosario
institution_str	I-15
repository_str	R-121
collection	Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR)
language	Inglés
topic	Infectious diseases Antimicrobial agents Reaction products Solvents Organic compounds
spellingShingle	Infectious diseases Antimicrobial agents Reaction products Solvents Organic compounds Di Liberto, Melina G. Caldo, Agustín J. Quiroga, Ariel Darío Riveira, Martín Jorge Derita, Marcos G. Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control
topic_facet	Infectious diseases Antimicrobial agents Reaction products Solvents Organic compounds
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.
format	article artículo publishedVersion
author	Di Liberto, Melina G. Caldo, Agustín J. Quiroga, Ariel Darío Riveira, Martín Jorge Derita, Marcos G.
author_facet	Di Liberto, Melina G. Caldo, Agustín J. Quiroga, Ariel Darío Riveira, Martín Jorge Derita, Marcos G.
author_sort	Di Liberto, Melina G.
title	Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control
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
publisher	American Chemical Society
publishDate	2021
url	http://hdl.handle.net/2133/21775 http://hdl.handle.net/2133/21775
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Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control

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