title: Optimized synthesis of novel prenyl ferulate performed by feruloyl esterases from Myceliophthora thermophila in microemulsions.
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 (IC50423.39 μM for PFA, 329.9 μM for FA). PFA was not cytotoxic at 0.8-100 μM (IC50220.23 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.
authors.affiliation: Division of Chemical Engineering, Department of Civil, Environmental and Natural Resources Engineering, Luleå University of Technology, 97187, Luleå, Sweden.
authors.forename: Io
authors.initials: I
authors.lastname: Antonopoulou
authors.affiliation: DuPont Industrial Biosciences, Nieuwe Kanaal 7-S, 6709 PA, Wageningen, The Netherlands.
authors.forename: Laura
authors.initials: L
authors.lastname: Leonov
authors.affiliation: Taros Chemicals GmbH & Co. KG, Emil Figge Str 76a, 44227, Dortmund, Germany.
authors.forename: Peter
authors.initials: P
authors.lastname: Jütten
authors.affiliation: Department of Chemical Sciences, University of Naples "Federico II", Via Cintia 4, 80126, Naples, Italy.
authors.forename: Gabriella
authors.initials: G
authors.lastname: Cerullo
authors.affiliation: Department of Chemical Sciences, University of Naples "Federico II", Via Cintia 4, 80126, Naples, Italy.
authors.forename: Vincenza
authors.initials: V
authors.lastname: Faraco
authors.affiliation: Institute of Biosciences and Applications NCSR "Demokritos," Laboratory of Cell Proliferation and Aging, T. Patriarchou Grigoriou & Neapoleos, 15310, Athens, Greece.
authors.forename: Adamantia
authors.initials: A
authors.lastname: Papadopoulou
authors.affiliation: Institute of Biosciences and Applications NCSR "Demokritos," Laboratory of Cell Proliferation and Aging, T. Patriarchou Grigoriou & Neapoleos, 15310, Athens, Greece.
authors.forename: Dimitris
authors.initials: D
authors.lastname: Kletsas
authors.affiliation: Korres Natural Products, 57 Km National Road, 32011, Lamia, Athens, Greece.
authors.forename: Marianna
authors.initials: M
authors.lastname: Ralli
authors.affiliation: Division of Chemical Engineering, Department of Civil, Environmental and Natural Resources Engineering, Luleå University of Technology, 97187, Luleå, Sweden.
authors.forename: Ulrika
authors.initials: U
authors.lastname: Rova
authors.affiliation: Division of Chemical Engineering, Department of Civil, Environmental and Natural Resources Engineering, Luleå University of Technology, 97187, Luleå, Sweden. paul.christakopoulos@ltu.se.
authors.forename: Paul
authors.initials: P
authors.lastname: Christakopoulos
mesh_terms: D000975:Antioxidants; D002265:Carboxylic Ester Hydrolases / Q000302:isolation & purification / Q000378:metabolism*; D002478:Cells, Cultured; D003373:Coumaric Acids / Q000378:metabolism* / Q000494:pharmacology; D004655:Emulsions; D004951:Esterification; D005347:Fibroblasts / Q000187:drug effects / Q000378:metabolism; D045782:Hemiterpenes; D006801:Humans; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D000439:Pentanols / Q000378:metabolism*; D017382:Reactive Oxygen Species / Q000378:metabolism; D020037:Sordariales / Q000201:enzymology* / Q000378:metabolism; D013696:Temperature
chemical_list: D000975:Antioxidants; D003373:Coumaric Acids; D004655:Emulsions; D045782:Hemiterpenes; D000439:Pentanols; D017382:Reactive Oxygen Species; C009034:prenol; C004999:ferulic acid; D002265:Carboxylic Ester Hydrolases; C070196:feruloyl esterase
keywords: Antioxidant; DCFH-DA; DPPH; Feruloyl esterase; Myceliophthora thermophila; Prenyl ferulate; Transesterification