Optimized synthesis of novel prenyl ferulate performed by feruloyl esterases from Myceliophthora thermophila in microemulsions |
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Authors: | Antonopoulou Io Leonov Laura Jütten Peter Cerullo Gabriella Faraco Vincenza Papadopoulou Adamantia Kletsas Dimitris Ralli Marianna Rova Ulrika Christakopoulos Paul |
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Institution: | 1.Division of Chemical Engineering, Department of Civil, Environmental and Natural Resources Engineering, Luleå University of Technology, 97187, Luleå, Sweden ;2.DuPont Industrial Biosciences, Nieuwe Kanaal 7-S, 6709 PA, Wageningen, The Netherlands ;3.Taros Chemicals GmbH & Co. KG, Emil Figge Str 76a, 44227, Dortmund, Germany ;4.Department of Chemical Sciences, University of Naples “Federico II”, Via Cintia 4, 80126, Naples, Italy ;5.Institute of Biosciences and Applications NCSR “Demokritos,” Laboratory of Cell Proliferation and Aging, T. Patriarchou Grigoriou & Neapoleos, 15310, Athens, Greece ;6.Korres Natural Products, 57 Km National Road, 32011, Lamia, Athens, Greece ; |
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Abstract: | Five feruloyl esterases (FAEs; EC 3.1.1.73), FaeA1, FaeA2, FaeB1, and FaeB2 from Myceliophthora thermophila C1 and MtFae1a from M. thermophila ATCC 42464, were tested for their ability to catalyze the transesterification of vinyl ferulate (VFA) with prenol in detergentless microemulsions. Reaction conditions were optimized investigating parameters such as the medium composition, the substrate concentration, the enzyme load, the pH, the temperature, and agitation. FaeB2 offered the highest transesterification yield (71.5 ± 0.2%) after 24 h of incubation at 30 °C using 60 mM VFA, 1 M prenol, and 0.02 mg FAE/mL in a mixture comprising of 53.4:43.4:3.2 v/v/v n-hexane:t-butanol:100 mM MOPS-NaOH, pH 6.0. At these conditions, the competitive side hydrolysis of VFA was 4.7-fold minimized. The ability of prenyl ferulate (PFA) and its corresponding ferulic acid (FA) to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals was significant and similar (IC50 423.39 μM for PFA, 329.9 μM for FA). PFA was not cytotoxic at 0.8–100 μM (IC50 220.23 μM) and reduced intracellular reactive oxygen species (ROS) in human skin fibroblasts at concentrations ranging between 4 and 20 μM as determined with the dichloro-dihydro-fluorescein diacetate (DCFH-DA) assay. |
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