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. 2022 Aug 7;27(15):5024.
doi: 10.3390/molecules27155024.

Lipase-Catalyzed Synthesis, Antioxidant Activity, Antimicrobial Properties and Molecular Docking Studies of Butyl Dihydrocaffeate

Bartłomiej Zieniuk  1 , Chimaobi James Ononamadu  2 , Karina Jasińska  1   3 , Katarzyna Wierzchowska  1   3 , Agata Fabiszewska  1
Affiliations

Lipase-Catalyzed Synthesis, Antioxidant Activity, Antimicrobial Properties and Molecular Docking Studies of Butyl Dihydrocaffeate

Bartłomiej Zieniuk et al. Molecules. .

Abstract

Green chemistry approaches, such as lipase-catalyzed esterification, are promising methods for obtaining valuable chemical compounds. In the case of the use of lipases, unlike in aqueous environments, the processes of the ester bond formations are encountered in organic solvents. The aim of the current research was to carry out the lipase-catalyzed synthesis of an ester of dihydrocaffeic acid. The synthesized compound was then evaluated for antioxidant and antimicrobial activities. However, the vast majority of its antioxidant activity was retained, which was demonstrated by means of DPPH· (2,2-diphenyl-1-picrylhydrazyl) and CUPRAC (cupric ion reducing antioxidant capacity) methods. Regarding its antimicrobial properties, the antifungal activity against Rhizopus oryzae is worth mentioning. The minimum inhibitory and fungicidal concentrations were 1 and 2 mM, respectively. The high antifungal activity prompted the use of molecular docking studies to verify potential protein targets for butyl ester of dihydrocaffeic ester. In the case of one fungal protein, namely 14-α sterol demethylase B, it was observed that the ester had comparable binding energy to the triazole medication, isavuconazole, but the interacted amino acid residues were different.

Keywords: Rhizopus oryzae; antifungal activity; butyl dihydrocaffeate; lipase-catalyzed synthesis; lipophilization; molecular docking.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of (a) dihydrocaffeic acid and (b) dopamine.
Figure 2
Figure 2
Synthesis of dihydrocaffeic acid butyl ester catalyzed by lipase B from C. antarctica (CALB).
Figure 3
Figure 3
Comparison of the diameter of the R. oryzae DSM 2199 mycelium on PDA medium containing the tested ester in concentrations of 0–2 mM. Asterisks (*) annotate the statistical difference (by Dunnett test) in inhibiting the mycelial growth by the tested compound in selected concentration in comparison with control (0 mM). For 2 mM ester concentration no R. oryzae growth was observed.
Figure 4
Figure 4
Photographs of R. oryzae mycelium after 4 days of cultivation on PDA medium containing the tested ester at the concentration of (a) 0, (b) 0.5 and (c) 1 mM, respectively.
Figure 5
Figure 5
Visualizations of docking analysis of glutamine-fructose-6-phosphate transaminase (GFAT) binding with butyl dihydrocaffeate: (a,b) 3D visualizations, (c) 2D binding interactions, and 14-α sterol demethylase B binding with butyl dihydrocaffeate: (d,e) 3D visualizations, (f) 2D binding interactions.
Figure 5
Figure 5
Visualizations of docking analysis of glutamine-fructose-6-phosphate transaminase (GFAT) binding with butyl dihydrocaffeate: (a,b) 3D visualizations, (c) 2D binding interactions, and 14-α sterol demethylase B binding with butyl dihydrocaffeate: (d,e) 3D visualizations, (f) 2D binding interactions.
Figure 6
Figure 6
Visualizations of docking analysis of Invasin CotH3 binding with butyl dihydrocaffeate: (a,b) 3D visualizations, (c) 2D binding interactions, and Mucoricin binding with butyl dihydrocaffeate: (d,e) 3D visualizations, (f) 2D binding interactions.
Figure 6
Figure 6
Visualizations of docking analysis of Invasin CotH3 binding with butyl dihydrocaffeate: (a,b) 3D visualizations, (c) 2D binding interactions, and Mucoricin binding with butyl dihydrocaffeate: (d,e) 3D visualizations, (f) 2D binding interactions.
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