Diferulate: A highly effective electron donor
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 effi...
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Veröffentlicht in: | Journal of electroanalytical chemistry (Lausanne, Switzerland) Switzerland), 2020-07, Vol.869, p.113950, Article 113950 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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.
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•Redox behavior of diferulic acids in aqueous media is reported.•Experimental and computational results are covered.•Ferulate dimerisation (conjugation) results in high electron-donating properties.•Diferulate is an easily oxidizable and non-cytotoxic radical scavenger. |
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ISSN: | 1572-6657 1873-2569 |
DOI: | 10.1016/j.jelechem.2020.113950 |