Enzymatic Oxidation of Ferulic Acid as a Way of Preparing New Derivatives

The ferulic acid (FA)-oxidation by Myceliophthora thermophila laccase was performed in phosphate buffer at 30 °C and pH 7.5 as an eco-friendly procedure. LC-MS analysis showed that oxidation products were four dehydrodimers (P1, P2, P3, P5) at MM = 386 g/mol, two dehydrotetramers (P6, P7) at MM = 77...

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Autores principales: Aljawish, Abdulhadi, Chevalot, Isabelle, Paris, Cédric, Muniglia, Lionel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9775523/
https://www.ncbi.nlm.nih.gov/pubmed/36546909
http://dx.doi.org/10.3390/biotech11040055
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author Aljawish, Abdulhadi
Chevalot, Isabelle
Paris, Cédric
Muniglia, Lionel
author_facet Aljawish, Abdulhadi
Chevalot, Isabelle
Paris, Cédric
Muniglia, Lionel
author_sort Aljawish, Abdulhadi
collection PubMed
description The ferulic acid (FA)-oxidation by Myceliophthora thermophila laccase was performed in phosphate buffer at 30 °C and pH 7.5 as an eco-friendly procedure. LC-MS analysis showed that oxidation products were four dehydrodimers (P1, P2, P3, P5) at MM = 386 g/mol, two dehydrotetramers (P6, P7) at MM = 770 g/mol and one decarboxylated dehydrodimer (P4) at MM = 340 g/mol. Structural characterization showed that FA-dehydrodimers were symmetric for P1 and P5 while asymmetric for P2, P3 and P4. Physicochemical characterization showed that oxidation products presented a higher lipophilicity than that of FA. Moreover, symmetric dimers and tetra dimers had a higher melting point compared to FA and its asymmetric dimers. Antioxidant and anti-proliferative assessments indicated that enzymatic oligomerization increased antioxidant and anti-proliferative properties of oxidation products for P2, P3 and P6 compared to FA. Finally, this enzymatic process in water could produce new molecules, having good antiradical and anti-proliferative activities.
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spelling pubmed-97755232022-12-23 Enzymatic Oxidation of Ferulic Acid as a Way of Preparing New Derivatives Aljawish, Abdulhadi Chevalot, Isabelle Paris, Cédric Muniglia, Lionel BioTech (Basel) Article The ferulic acid (FA)-oxidation by Myceliophthora thermophila laccase was performed in phosphate buffer at 30 °C and pH 7.5 as an eco-friendly procedure. LC-MS analysis showed that oxidation products were four dehydrodimers (P1, P2, P3, P5) at MM = 386 g/mol, two dehydrotetramers (P6, P7) at MM = 770 g/mol and one decarboxylated dehydrodimer (P4) at MM = 340 g/mol. Structural characterization showed that FA-dehydrodimers were symmetric for P1 and P5 while asymmetric for P2, P3 and P4. Physicochemical characterization showed that oxidation products presented a higher lipophilicity than that of FA. Moreover, symmetric dimers and tetra dimers had a higher melting point compared to FA and its asymmetric dimers. Antioxidant and anti-proliferative assessments indicated that enzymatic oligomerization increased antioxidant and anti-proliferative properties of oxidation products for P2, P3 and P6 compared to FA. Finally, this enzymatic process in water could produce new molecules, having good antiradical and anti-proliferative activities. MDPI 2022-12-05 /pmc/articles/PMC9775523/ /pubmed/36546909 http://dx.doi.org/10.3390/biotech11040055 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Aljawish, Abdulhadi
Chevalot, Isabelle
Paris, Cédric
Muniglia, Lionel
Enzymatic Oxidation of Ferulic Acid as a Way of Preparing New Derivatives
title Enzymatic Oxidation of Ferulic Acid as a Way of Preparing New Derivatives
title_full Enzymatic Oxidation of Ferulic Acid as a Way of Preparing New Derivatives
title_fullStr Enzymatic Oxidation of Ferulic Acid as a Way of Preparing New Derivatives
title_full_unstemmed Enzymatic Oxidation of Ferulic Acid as a Way of Preparing New Derivatives
title_short Enzymatic Oxidation of Ferulic Acid as a Way of Preparing New Derivatives
title_sort enzymatic oxidation of ferulic acid as a way of preparing new derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9775523/
https://www.ncbi.nlm.nih.gov/pubmed/36546909
http://dx.doi.org/10.3390/biotech11040055
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AT pariscedric enzymaticoxidationofferulicacidasawayofpreparingnewderivatives
AT muniglialionel enzymaticoxidationofferulicacidasawayofpreparingnewderivatives

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