Cargando…

Efficient Production of the Flavoring Agent Zingerone and of both (R)- and (S)-Zingerols via Green Fungal Biocatalysis. Comparative Antifungal Activities between Enantiomers

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. flavu...

Descripción completa

Detalles Bibliográficos
Autores principales: Svetaz, Laura A., Di Liberto, Melina G., Zanardi, María M., Suárez, Alejandra G., Zacchino, Susana A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4284693/
https://www.ncbi.nlm.nih.gov/pubmed/25470023
http://dx.doi.org/10.3390/ijms151222042
_version_ 1782351434416652288
author Svetaz, Laura A.
Di Liberto, Melina G.
Zanardi, María M.
Suárez, Alejandra G.
Zacchino, Susana A.
author_facet Svetaz, Laura A.
Di Liberto, Melina G.
Zanardi, María M.
Suárez, Alejandra G.
Zacchino, Susana A.
author_sort Svetaz, Laura A.
collection PubMed
description 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 Online
Article
Text
id pubmed-4284693
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-42846932015-01-21 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 M. Suárez, Alejandra G. Zacchino, Susana A. Int J Mol Sci Article 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. MDPI 2014-12-01 /pmc/articles/PMC4284693/ /pubmed/25470023 http://dx.doi.org/10.3390/ijms151222042 Text en © 2014 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Svetaz, Laura A.
Di Liberto, Melina G.
Zanardi, María M.
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
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_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_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_sort efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis. comparative antifungal activities between enantiomers
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4284693/
https://www.ncbi.nlm.nih.gov/pubmed/25470023
http://dx.doi.org/10.3390/ijms151222042
work_keys_str_mv AT svetazlauraa efficientproductionoftheflavoringagentzingeroneandofbothrandszingerolsviagreenfungalbiocatalysiscomparativeantifungalactivitiesbetweenenantiomers
AT dilibertomelinag efficientproductionoftheflavoringagentzingeroneandofbothrandszingerolsviagreenfungalbiocatalysiscomparativeantifungalactivitiesbetweenenantiomers
AT zanardimariam efficientproductionoftheflavoringagentzingeroneandofbothrandszingerolsviagreenfungalbiocatalysiscomparativeantifungalactivitiesbetweenenantiomers
AT suarezalejandrag efficientproductionoftheflavoringagentzingeroneandofbothrandszingerolsviagreenfungalbiocatalysiscomparativeantifungalactivitiesbetweenenantiomers
AT zacchinosusanaa efficientproductionoftheflavoringagentzingeroneandofbothrandszingerolsviagreenfungalbiocatalysiscomparativeantifungalactivitiesbetweenenantiomers