Laccase-catalysed oxidation of ferulic acid and ethyl ferulate in aqueous medium: A green procedure for the synthesis of new compounds

• Published in: Food chemistry 2014-02, Vol.145, p.1046-1054
• Main Authors: Aljawish, Abdulhadi, Chevalot, Isabelle, Jasniewski, Jordane, Paris, Cédric, Scher, Joël, Muniglia, Lionel
• Format: Article
• Language: English
• Subjects: Antioxidant; Antioxidants - adverse effects; Antioxidants - chemistry; Antioxidants - metabolism; Biological and medical sciences; Caffeic Acids - adverse effects; Caffeic Acids - chemistry; Caffeic Acids - metabolism; Cell Survival; Cells, Cultured; Chromatography, High Pressure Liquid; Coumaric Acids - adverse effects; Coumaric Acids - chemistry; Coumaric Acids - metabolism; Cytotoxicity; Dye; Enzymatic oxidation; Ethyl ferulate; Ferulic acid; Food Coloring Agents - adverse effects; Food Coloring Agents - chemistry; Food Coloring Agents - metabolism; Food Preservatives - adverse effects; Food Preservatives - chemistry; Food Preservatives - metabolism; Food toxicology; Fungal Proteins - genetics; Fungal Proteins - isolation & purification; Fungal Proteins - metabolism; Green Chemistry Technology; Human Umbilical Vein Endothelial Cells - metabolism; Humans; Laccase; Laccase - genetics; Laccase - isolation & purification; Laccase - metabolism; Life Sciences; Mass Spectrometry; Medical sciences; Oxidation-Reduction; Recombinant Proteins - isolation & purification; Recombinant Proteins - metabolism; Sordariales - enzymology; Spectrophotometry, Ultraviolet; Substrate Specificity; Toxicology; Ultrafiltration
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2013.07.119

•The enzymatic oxidation of ferulic acid (FA) and ethyl ferulate (EF) by Myceliophthora thermophila laccase.•The enzymatic oxidation was performed in aqueous medium under an eco-friendly procedure to synthesize new active molecules.•The enzymatic procedure in aqueous medium could provide new compounds presenting optical, antioxidant and cytotoxic interest. 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 386g/mol and a EF-major product with a molecular mass of 442g/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.