Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers

Autores
Svetaz, Laura A.; Di Liberto, Melina G.; Zanardi, María Marta; Suárez, Alejandra G.; Zacchino, Susana A.
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Fil: Svetaz, Laura A. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Di Liberto, Melina G. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Zanardi, María M. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas, ; Argentina
Fil: Zanardi, María M. Consejo Nacional de Investigaciones Científicas y Técnicas de Argentina. Instituto de Química Rosario; Argentina
Fil: Suárez, Alejandra G. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas, ; Argentina
Fil: Suárez, Alejandra G. Consejo Nacional de Investigaciones Científicas y Técnicas de Argentina. Instituto de Química Rosario; Argentina
Fil: Zacchino, Susana A. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Abstract: Zingerone (1) and both chiral forms of zingerol (2) were obtained from dehydrozingerone (3) by biotransformation with filamentous fungi. The bioconversion of 3 with A. fumigatus, G. candidum or R. oryzae allowed the production of 1 as the sole product at 8 h and in 81%–90% at 72 h. In turn, A. flavus, A. niger, C. echinulata, M. circinelloides and P. citrinum produced 1 at 8 h, but at 72 h alcohol 2 was obtained as the major product (74%–99%). Among them, A. niger and M. circinelloides led to the anti-Prelog zingerol (R)-2 in only one step with high conversion rates and ee. Instead, C. echinulata and P. citrinum allowed to obtain (S)-2 in only one step, with high conversion rates and ee. Both chiral forms of 2 were tested for antifungal properties against a panel of clinically important fungi, showing that (R)-, but not (S)-2 possessed antifungal activity.
Fuente
International Journal of Molecular Sciences vol.15, 2014
Materia
ANTIFUNGICO
HONGOS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/4.0/
Repositorio
Repositorio Institucional (UCA)
Institución
Pontificia Universidad Católica Argentina
OAI Identificador
oai:ucacris:123456789/11468
Acceder
id RIUCA_5e3fc6b122f25d08dc2f2aaf3f71ac42
oai_identifier_str oai:ucacris:123456789/11468
network_acronym_str RIUCA
repository_id_str 2585
network_name_str Repositorio Institucional (UCA)
spelling Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomersSvetaz, Laura A.Di Liberto, Melina G.Zanardi, María MartaSuárez, Alejandra G.Zacchino, Susana A.ANTIFUNGICOHONGOSFil: Svetaz, Laura A. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Di Liberto, Melina G. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Zanardi, María M. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas, ; ArgentinaFil: Zanardi, María M. Consejo Nacional de Investigaciones Científicas y Técnicas de Argentina. Instituto de Química Rosario; ArgentinaFil: Suárez, Alejandra G. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas, ; ArgentinaFil: Suárez, Alejandra G. Consejo Nacional de Investigaciones Científicas y Técnicas de Argentina. Instituto de Química Rosario; ArgentinaFil: Zacchino, Susana A. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaAbstract: Zingerone (1) and both chiral forms of zingerol (2) were obtained from dehydrozingerone (3) by biotransformation with filamentous fungi. The bioconversion of 3 with A. fumigatus, G. candidum or R. oryzae allowed the production of 1 as the sole product at 8 h and in 81%–90% at 72 h. In turn, A. flavus, A. niger, C. echinulata, M. circinelloides and P. citrinum produced 1 at 8 h, but at 72 h alcohol 2 was obtained as the major product (74%–99%). Among them, A. niger and M. circinelloides led to the anti-Prelog zingerol (R)-2 in only one step with high conversion rates and ee. Instead, C. echinulata and P. citrinum allowed to obtain (S)-2 in only one step, with high conversion rates and ee. Both chiral forms of 2 were tested for antifungal properties against a panel of clinically important fungi, showing that (R)-, but not (S)-2 possessed antifungal activity.MDPI2014info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfhttps://repositorio.uca.edu.ar/handle/123456789/114681422-006710.3390/ijms151222042Svetaz, L. A., Di Liberto, M. G., Zanardi, M. M., Suárez, A. G., Zacchino, S.A. Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers [en línea]. International Journal of Molecular Sciences. 2014 (15). Disponible en: https://repositorio.uca.edu.ar/handle/123456789/11468International Journal of Molecular Sciences vol.15, 2014reponame:Repositorio Institucional (UCA)instname:Pontificia Universidad Católica Argentinaenginfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/4.0/2026-01-08T11:21:16Zoai:ucacris:123456789/11468instacron:UCAInstitucionalhttps://repositorio.uca.edu.ar/Universidad privadaNo correspondehttps://repositorio.uca.edu.ar/oaiclaudia_fernandez@uca.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:25852026-01-08 11:21:16.585Repositorio Institucional (UCA) - Pontificia Universidad Católica Argentinafalse
dc.title.none.fl_str_mv Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers
title Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers
spellingShingle Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers
Svetaz, Laura A.
ANTIFUNGICO
HONGOS
title_short Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers
title_full Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers
title_fullStr Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers
title_full_unstemmed Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers
title_sort Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers
dc.creator.none.fl_str_mv Svetaz, Laura A.
Di Liberto, Melina G.
Zanardi, María Marta
Suárez, Alejandra G.
Zacchino, Susana A.
author Svetaz, Laura A.
author_facet Svetaz, Laura A.
Di Liberto, Melina G.
Zanardi, María Marta
Suárez, Alejandra G.
Zacchino, Susana A.
author_role author
author2 Di Liberto, Melina G.
Zanardi, María Marta
Suárez, Alejandra G.
Zacchino, Susana A.
author2_role author
author
author
author
dc.subject.none.fl_str_mv ANTIFUNGICO
HONGOS
topic ANTIFUNGICO
HONGOS
dc.description.none.fl_txt_mv Fil: Svetaz, Laura A. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Di Liberto, Melina G. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Zanardi, María M. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas, ; Argentina
Fil: Zanardi, María M. Consejo Nacional de Investigaciones Científicas y Técnicas de Argentina. Instituto de Química Rosario; Argentina
Fil: Suárez, Alejandra G. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas, ; Argentina
Fil: Suárez, Alejandra G. Consejo Nacional de Investigaciones Científicas y Técnicas de Argentina. Instituto de Química Rosario; Argentina
Fil: Zacchino, Susana A. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Abstract: Zingerone (1) and both chiral forms of zingerol (2) were obtained from dehydrozingerone (3) by biotransformation with filamentous fungi. The bioconversion of 3 with A. fumigatus, G. candidum or R. oryzae allowed the production of 1 as the sole product at 8 h and in 81%–90% at 72 h. In turn, A. flavus, A. niger, C. echinulata, M. circinelloides and P. citrinum produced 1 at 8 h, but at 72 h alcohol 2 was obtained as the major product (74%–99%). Among them, A. niger and M. circinelloides led to the anti-Prelog zingerol (R)-2 in only one step with high conversion rates and ee. Instead, C. echinulata and P. citrinum allowed to obtain (S)-2 in only one step, with high conversion rates and ee. Both chiral forms of 2 were tested for antifungal properties against a panel of clinically important fungi, showing that (R)-, but not (S)-2 possessed antifungal activity.
description Fil: Svetaz, Laura A. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
publishDate 2014
dc.date.none.fl_str_mv 2014
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 https://repositorio.uca.edu.ar/handle/123456789/11468
1422-0067
10.3390/ijms151222042
Svetaz, L. A., Di Liberto, M. G., Zanardi, M. M., Suárez, A. G., Zacchino, S.A. Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers [en línea]. International Journal of Molecular Sciences. 2014 (15). Disponible en: https://repositorio.uca.edu.ar/handle/123456789/11468
url https://repositorio.uca.edu.ar/handle/123456789/11468
identifier_str_mv 1422-0067
10.3390/ijms151222042
Svetaz, L. A., Di Liberto, M. G., Zanardi, M. M., Suárez, A. G., Zacchino, S.A. Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers [en línea]. International Journal of Molecular Sciences. 2014 (15). Disponible en: https://repositorio.uca.edu.ar/handle/123456789/11468
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/4.0/
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv International Journal of Molecular Sciences vol.15, 2014
reponame:Repositorio Institucional (UCA)
instname:Pontificia Universidad Católica Argentina
reponame_str Repositorio Institucional (UCA)
collection Repositorio Institucional (UCA)
instname_str Pontificia Universidad Católica Argentina
repository.name.fl_str_mv Repositorio Institucional (UCA) - Pontificia Universidad Católica Argentina
repository.mail.fl_str_mv claudia_fernandez@uca.edu.ar
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score 13.25844

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