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

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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 t...

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Autores principales: Svetaz, Laura A., Di Liberto, Melina G., Zanardi, María Marta, Suárez, Alejandra G., Zacchino, Susana A.
Formato: Artículo
Lenguaje:Inglés
Publicado: MDPI 2021
Materias:
ANTIFUNGICO
HONGOS
Acceso en línea:https://repositorio.uca.edu.ar/handle/123456789/11468
Aporte de:
Repositorio Institucional de la Universidad Católica Argentina (UCA) de Universidad Católica Argentina
id I33-R139-123456789-11468
record_format dspace
spelling I33-R139-123456789-114682023-04-26T15:27:59Z 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. Di Liberto, Melina G. Zanardi, María Marta Suárez, Alejandra G. Zacchino, Susana A. ANTIFUNGICO HONGOS 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. 2021-05-03T13:24:59Z 2021-05-03T13:24:59Z 2014 Artículo 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 1422-0067 https://repositorio.uca.edu.ar/handle/123456789/11468 10.3390/ijms151222042 eng Acceso abierto http://creativecommons.org/licenses/by-nc-sa/4.0/ application/pdf MDPI International Journal of Molecular Sciences vol.15, 2014
institution Universidad Católica Argentina
institution_str I-33
repository_str R-139
collection Repositorio Institucional de la Universidad Católica Argentina (UCA)
language Inglés
topic ANTIFUNGICO
HONGOS
spellingShingle ANTIFUNGICO
HONGOS
Svetaz, Laura A.
Di Liberto, Melina G.
Zanardi, María Marta
Suárez, Alejandra G.
Zacchino, Susana A.
Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers
topic_facet ANTIFUNGICO
HONGOS
description 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.
format Artículo
author Svetaz, Laura A.
Di Liberto, Melina G.
Zanardi, María Marta
Suárez, Alejandra G.
Zacchino, Susana A.
author_facet Svetaz, Laura A.
Di Liberto, Melina G.
Zanardi, María Marta
Suárez, Alejandra G.
Zacchino, Susana A.
author_sort Svetaz, Laura A.
title Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers
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
publisher MDPI
publishDate 2021
url https://repositorio.uca.edu.ar/handle/123456789/11468
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