Diferulate: A highly effective electron donor

0524441 - ÚFCH JH 2021 RIV CH eng J - Journal Article
Vacek, J. - Zatloukalová, M. - Vrba, J. - De Vleeschouwer, F. - de Proft, F. - Obluková, Michaela - Sokolová, Romana - Pospíšil, Jiří
Diferulate: A highly effective electron donor.
Journal of Electroanalytical Chemistry. Roč. 865, JUL 2020 (2020), č. článku 113950. ISSN 1572-6657. E-ISSN 1873-2569
R&D Projects: GA MŠMT(CZ) LO1304; GA MŠMT(CZ) LO1204; GA MŠMT(CZ) EF16_019/0000738
Institutional support: RVO:61388955 ; RVO:61389030
Keywords : Lignan electrochemistry * Diferulic acid * Phenylpropanoids
OECD category: Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis); Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis) (UEB-Q)
Impact factor: 4.464, year: 2020
Method of publishing: Limited access

The screening of new molecules with high electron-donor properties is important for the design of new bioactive and technologically applicable substances. Here we propose diferulate (1), (Z)-2-(5-((E)-2-carboxyvinyl)-2-hydroxy-3-methoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid, to be an efficient electron donor which undergoes anodic conversion in aqueous media (pH 7) at around +0.15 V, vs. Ag|AgCl|3 M KCl. The low potential of oxidation of 1 indicates its high electron-donor capacity, which was documented by DPPH and ABTS radical scavenging and anti-lipoperoxidation activity analyses and also supported by in silico approaches. The results showed that compound 1, unlike ferulic acid 2 and the P1 benzofuranone synthetic precursor of 1, exhibits unique antiradical and antioxidant properties compared to trolox 3, which served as the positive control. No cytotoxic effects were observed for 1 in the 1–50 μM range. We conclude that the proposed structure 1 can be used for the further design of molecules whose biological (chemoprotective) activity is associated with high electron-donor properties.
Permanent Link: http://hdl.handle.net/11104/0308802