title: 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 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.
authors.affiliation: Pharmacognosy Area, School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000 Rosario, Argentina. lsvetaz@fbioyf.unr.edu.ar.
authors.forename: Laura A
authors.initials: LA
authors.lastname: Svetaz
authors.affiliation: Pharmacognosy Area, School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000 Rosario, Argentina. melinna85@hotmail.com.
authors.forename: Melina G
authors.initials: MG
authors.lastname: Di Liberto
authors.affiliation: Institute of Chemistry Rosario (IQUIR)-CONICET, School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000 Rosario, Argentina. zanardi@iquir-conicet.gov.ar.
authors.forename: María M
authors.initials: MM
authors.lastname: Zanardi
authors.affiliation: Institute of Chemistry Rosario (IQUIR)-CONICET, School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000 Rosario, Argentina. suarez@iquir-conicet.gov.ar.
authors.forename: Alejandra G
authors.initials: AG
authors.lastname: Suárez
authors.affiliation: Pharmacognosy Area, School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000 Rosario, Argentina. szacchin@fbioyf.unr.edu.ar.
authors.forename: Susana A
authors.initials: SA
authors.lastname: Zacchino
mesh_terms: D000935:Antifungal Agents / Q000494:pharmacology*; D055162:Biocatalysis / Q000187:drug effects*; D001711:Biotransformation / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D004952:Esters / Q000737:chemistry; D005421:Flavoring Agents / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects / Q000378:metabolism*; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D066244:Proton Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013997:Time Factors
chemical_list: D000935:Antifungal Agents; D004952:Esters; D005421:Flavoring Agents; C013738:zingerone; D006139:Guaiacol