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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.
Highlights
Ferulic acid (FA), along with other hydroxycinnamic acids, has a widespread industrial potential due to its strong antioxidant activity
Transesterification was tested in four different compositions of the ternary system n-hexane:t-butanol:100 mM MOPSNaOH, pH 6.0 monitoring the competitive hydrolysis of vinyl ferulate (VFA) as side reaction
Product selectivity was highest at lowest water content for all tested feruloyl esterases (FAEs); it was shown that such low water content was detrimental to the yield
Summary
Ferulic acid (FA), along with other hydroxycinnamic acids (pcoumaric, caffeic, sinapic), has a widespread industrial potential due to its strong antioxidant activity. It is ubiquitous in nature as a component of plant cell walls offering linkage with lignin; in arabinoxylans, FA is esterified to the C-5 of α-Larabinofuranose; in pectins, it is esterified to the C-2 of α1➔5linked arabinofuranose or to the C-6 of β1➔4-linked galactopyranose, while in xyloglucans, it is found attached to the C-4 of α-D-xylopyranose (Kikugawa et al 2012). FA is present in grains, fruits, and vegetables (Zhao and Moghadasian 2008). A major disadvantage of FA and other natural antioxidants is their poor solubility in both oil and aqueous media limiting their application in formulations intended for food, cosmetic, cosmeceutical, or pharmaceutical products
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