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

International Journal of Molecular Sciences

Laura A. Svetaz¹  Melina G. Di Liberto¹  Mar໚ M. Zanardi²  Alejandra G. Suárez²  Susana A. Zacchino¹ 

[1] Pharmacognosy Area, School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000 Rosario, Argentina; E-Mails:;Institute of Chemistry Rosario (IQUIR)-CONICET, School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000 Rosario, Argentina; E-Mails:

关键词: zingerone;    chiral zingerols;    filamentous fungi;    enantioselective bioconversions;    green chemistry;    antifungal;   

DOI  :  10.3390/ijms151222042

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.