Efficient Production of the Flavoring Agent Zingerone and of both R- and S-Zingerols via Green Fungal Biocatalysis. Comparative Antifungal Activities between EnantiomersReportar como inadecuado




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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.



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





Autor: Laura A. Svetaz 1, Melina G. Di Liberto 1, María M. Zanardi 2, Alejandra G. Suárez 2 and Susana A. Zacchino 1,*

Fuente: http://mdpi.com/



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