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.

The Effects of Dehydrozingerone on Growth, Biofilm Formation, and Ergosterol Biosynthesis of Candida albicans

“…Moreover, these compounds demonstrated in vitro cytotoxic activity against some cancer cell lines (HeLa, LS174, and A549) [22]. Svetaz et al (2014) have studied biotransformation and antifungal activity of DHZ and two of its derivatives on some filamentous fungi, including Aspergillus, Fusarium, Geoterichum, Cunninghamella, Mucor, Penicillium, Rhizopus, and Trichosporum [23]. In the present study, we showed that the growth and biofilm 2021 Vol.…”

Stereoselective Biocatalyzed Reductions of Ginger Active Components Recovered from Industrial Wastes

“…[53] C). [24] [ 13 C NMR (101 MHz, CDCl 3 ) δ 146.4, 143.7, 133.9, 120.92, 114.2, 110.9, 67.6, 55.9, 41.1, 31.8, 23.7. [24] ½ � 20 D = À 14.06 (c 0.398, CHCl 3 ).…”

“…[24] [ 13 C NMR (101 MHz, CDCl 3 ) δ 146.4, 143.7, 133.9, 120.92, 114.2, 110.9, 67.6, 55.9, 41.1, 31.8, 23.7. [24] ½ � 20 D = À 14.06 (c 0.398, CHCl 3 ). 1 H NMR (400 MHz, CDCl 3 ) δ 6.84 (d, J = 7.8 Hz, 1H), 6.71 (d, J = 9.4 Hz, 2H), 5.61 (s, 1H), 3.88 (s, 3H), 3.83 (dd, J = 12.1, 6.1 Hz, 1H), 2.74-2.57 (m, 2H), 1.80-1.72 (m, 2H), 1.24 (d, J = 6.1 Hz, 3H).…”

“…[23] As far as enzyme-catalyzed stereoselective reduction of gingerol-like compounds concerns, there are only a few reports so far. For example, the reduction of zingerone (4) by different fungal strains has been recently investigated by Svetaz et al [24] The biotransformation of 1 a and 6-shogaol (2) by Aspergillus niger strains to reduced derivatives has been reported as well. [25,26] However, these studies were mainly focused on the definition of metabolite profiles and in monitoring their changes in the culture media according to incubation times.…”

“…As far as enzyme‐catalyzed stereoselective reduction of gingerol‐like compounds concerns, there are only a few reports so far. For example, the reduction of zingerone ( 4 ) by different fungal strains has been recently investigated by Svetaz et al [24] . The biotransformation of 1 a and 6‐shogaol ( 2 ) by Aspergillus niger strains to reduced derivatives has been reported as well [25,26] …”