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Int. J. Mol. Sci. 2014, 15(12), 22042-22058; doi:10.3390/ijms151222042

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

1
Pharmacognosy Area, School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000 Rosario, Argentina
2
Institute of Chemistry Rosario (IQUIR)-CONICET, School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000 Rosario, Argentina
*
Author to whom correspondence should be addressed.
Received: 8 October 2014 / Revised: 11 November 2014 / Accepted: 12 November 2014 / Published: 1 December 2014
(This article belongs to the Special Issue Green Chemistry and the Biorefinery)
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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 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. View Full-Text
Keywords: zingerone; chiral zingerols; filamentous fungi; enantioselective bioconversions; green chemistry; antifungal zingerone; chiral zingerols; filamentous fungi; enantioselective bioconversions; green chemistry; antifungal
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MDPI and ACS Style

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. Int. J. Mol. Sci. 2014, 15, 22042-22058.

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