title: Laccase-catalysed oxidation of ferulic acid and ethyl ferulate in aqueous medium: a green procedure for the synthesis of new compounds.
abstract: The enzymatic oxidation of ferulic acid (FA) and ethyl ferulate (EF) with Myceliophthora thermophila laccase, as biocatalyst, was performed in aqueous medium using an eco-friendly procedure to synthesize new active molecules. First, the commercial laccase was ultrafiltrated allowing for the elimination of phenolic contaminants and increasing the specific activity by a factor of 2. Then, kinetic parameters of this laccase were determined for both substrates (FA, EF), indicating a higher substrate affinity for ethyl ferulate. Additionally, enzymatic oxidation led to the synthesis of a FA-major product, exhibiting a molecular mass of 386 g/mol and a EF-major product with a molecular mass of 442 g/mol. Structural analyses by mass spectrometry allowed the identification of dimeric derivatives. The optical properties of the oxidation products showed the increase of red and yellow colours, with FA-products compared to EF-products. Additionally, enzymatic oxidation led to a decrease of antioxidant and cytotoxic activities compared to initial substrates. Consequently, this enzymatic procedure in aqueous medium could provide new compounds presenting optical, antioxidant and cytotoxic interest.
authors.affiliation: Laboratoire d'Ingénierie des Biomolécules (LIBio), Université de Lorraine, 2 avenue de la Forêt de Haye, TSA 40602, 54518 Vandœuvre-lès-Nancy, France.
authors.forename: Abdulhadi
authors.initials: A
authors.lastname: Aljawish
authors.forename: Isabelle
authors.initials: I
authors.lastname: Chevalot
authors.forename: Jordane
authors.initials: J
authors.lastname: Jasniewski
authors.forename: Cédric
authors.initials: C
authors.lastname: Paris
authors.forename: Joël
authors.initials: J
authors.lastname: Scher
authors.forename: Lionel
authors.initials: L
authors.lastname: Muniglia
mesh_terms: D000975:Antioxidants / Q000009:adverse effects / Q000737:chemistry / Q000378:metabolism*; D002109:Caffeic Acids / Q000009:adverse effects / Q000737:chemistry / Q000378:metabolism*; D002470:Cell Survival; D002478:Cells, Cultured; D002851:Chromatography, High Pressure Liquid; D003373:Coumaric Acids / Q000009:adverse effects / Q000737:chemistry / Q000378:metabolism*; D005505:Food Coloring Agents / Q000009:adverse effects / Q000737:chemistry / Q000378:metabolism*; D005520:Food Preservatives / Q000009:adverse effects / Q000737:chemistry / Q000378:metabolism*; D005656:Fungal Proteins / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism*; D055772:Green Chemistry Technology; D061307:Human Umbilical Vein Endothelial Cells / Q000378:metabolism; D006801:Humans; D042845:Laccase / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism*; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D011994:Recombinant Proteins / Q000302:isolation & purification / Q000378:metabolism; D020037:Sordariales / Q000201:enzymology; D013056:Spectrophotometry, Ultraviolet; D013379:Substrate Specificity; D014462:Ultrafiltration
chemical_list: D000975:Antioxidants; D002109:Caffeic Acids; D003373:Coumaric Acids; D005505:Food Coloring Agents; D005520:Food Preservatives; D005656:Fungal Proteins; D011994:Recombinant Proteins; C099085:ethyl ferulate; C004999:ferulic acid; D042845:Laccase
keywords: Antioxidant; Cytotoxicity; Dye; Enzymatic oxidation; Ethyl ferulate; Ferulic acid; Laccase