Efficient production of the flavoring agent zingerone and of both (r)- and (s)-zingerols via green fungal biocatalysis: comparative antifungal activities between enantiomers
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: | , , , , |
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| Formato: | Artículo |
| Lenguaje: | Inglés |
| Publicado: |
MDPI
2021
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| Materias: | |
| Acceso en línea: | https://repositorio.uca.edu.ar/handle/123456789/11468 |
| Aporte de: |
| Sumario: | 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. |
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