Samenvatting
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.
| Originele taal-2 | English |
|---|---|
| Artikelnummer | 113950 |
| Tijdschrift | Journal of Electroanalytical Chemistry |
| Volume | 869 |
| DOI's | |
| Status | Published - 15 jul. 2020 |
Bibliografische nota
Funding Information:J.V. and R.S. gratefully acknowledge grants RVO: 61989592 and 61388955 from the Czech Ministry of Education. J.P. wishes to thank the Ministry of Education, Youth and Sports of the Czech Republic (grant LO1304 from the National Program of Sustainability and LO1204 from the National Program of Sustainability I) as well as gratefully acknowledging the European Regional Development Fund Project “Centre for Experimental Plant Biology” (No. CZ.02.1.01/0.0/0.0/16_019/0000738) for their financial support. F.D.V. wishes to thank the VUB for the Strategic Research Program awarded to ALGC. F.D.P. wishes to thank FWO-Vlaanderen and the Free University of Brussels (VUB) for their continuous support of the ALGC research group, in particular the VUB for the Strategic Research Program awarded to ALGC, which began on January 1, 2013. F.D.P. also wishes to thank the Francqui foundation for the position as Francqui research professor. We are grateful to Hana Kozubíková and Zita Školařová for their technical assistance and to Dr. Adam Přibylka for performing the titration-based experiments. We wish to thank Ben Watson-Jones MEng for providing linguistic assistance.
Funding Information:
J.V. and R.S. gratefully acknowledge grants RVO: 61989592 and 61388955 from the Czech Ministry of Education . J.P. wishes to thank the Ministry of Education, Youth and Sports of the Czech Republic (grant LO1304 from the National Program of Sustainability and LO1204 from the National Program of Sustainability I) as well as gratefully acknowledging the European Regional Development Fund Project “Centre for Experimental Plant Biology” (No. CZ.02.1.01/0.0/0.0/16_019/0000738 ) for their financial support. F.D.V. wishes to thank the VUB for the Strategic Research Program awarded to ALGC. F.D.P. wishes to thank FWO-Vlaanderen and the Free University of Brussels (VUB) for their continuous support of the ALGC research group, in particular the VUB for the Strategic Research Program awarded to ALGC, which began on January 1, 2013. F.D.P. also wishes to thank the Francqui foundation for the position as Francqui research professor. We are grateful to Hana Kozubíková and Zita Školařová for their technical assistance and to Dr. Adam Přibylka for performing the titration-based experiments. We wish to thank Ben Watson-Jones MEng for providing linguistic assistance.
Publisher Copyright:
© 2020 Elsevier B.V.
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.