Design, synthesis, characterization of ferulic acid and p-coumaric acid amide derivatives as an antibacterial/antioxidant agent

Abstract

Ferulic acid and p-coumaric acid, cinnamic derivatives of phenolic acid, have antibacterial, prooxidant, and antioxidant effects. In this study ferulic acid and p-coumaric acid amide derivatives were investigated for their antibacterial and antioxidant properties are described in this communication. The most effective conjugates against B subtilis were 5b (IC₅₀: 215 ​± ​1.3 ​μM) and 4d (IC₅₀: 336 ​± ​2.7 ​μM) and against P. aeruginosa were 4b (IC₅₀: 365 ​± ​2.8 ​μM) and 5b (IC₅₀: 341 ​± ​3.6 ​μM), whereas the none of conjugates were more effective against E. coli than reference Kanamycin. Conjugates 5b was the most effective against B subtilis of all the synthesized conjugates, with IC₅₀ values of (IC₅₀: 215 ​± ​1.3 ​μM). The free radical scavenging capacity of each compound was determined using the DPPH and ABTS assays. Conjugates 4b (IC₅₀: 53 ​± ​3.6 ​μM), 4c (IC₅₀: 58 ​± ​1.3 ​μM), 4d (IC₅₀: 57 ​± ​2.5 ​μM), 5b (IC₅₀: 29 ​± ​1.5 ​μM) and 4a (IC₅₀: 56 ​± ​4.3 ​μM) have greater antioxidant capacity than ferulic acid and ascorbic acid in the DPPH assay. Whereas in the ABTS assay, compounds 4b (IC₅₀: 7 ​± ​1.8 ​μM), 5b (IC₅₀: 5 ​± ​0.7 ​μM), 4a (IC₅₀: 9 ​± ​3.2 ​μM), 4g (IC₅₀: 7 ​± ​2.3 ​μM), and 5a (IC₅₀: 8 ​± ​4.3 ​μM) showed more antioxidant activity than ferulic acid, p-coumaric acid and ascorbic acid. Thus, a large library of compounds derived from bile acid can be easily synthesized for extensive structure-activity relationship studies in order to identify the most appropriate antibacterial and antioxidant agents.

Keywords

Ferulic acid / p-Coumaric acid / Amide derivatives / Antioxidant / Antibacterial

Analytical statistics

Each experiment was carried out three times. The average and standard deviation (SD) of all the data were used to express them. One-way ANOVA analysis was used to determine the significance of the results. A significant difference is shown by the value p ​< ​0.05.

Author contributions

SM provided the entire infrastructure and supervised the research. CGH performed and analyzed the experiments. SM and CGH wrote the manuscript. SM reviewed the manuscript. Both authors have read and approved the final manuscript.

Conflicts of interest

Authors declare no competing financial interest.

Data availability

Data will be made available on reasonable request.

Ethics approval

Not applicable.

Funding information

This research received no funding.

Declaration of statement

The Author (s) declare that there is no conflict of interest.

Acknowledgments

CGH thanks the Institute of Advanced Research, Gandhinagar, India for providing financial support.

Appendix A. Supplementary data

Supplementary data to this article can be found online at https://doi.org/10.1016/j.pscia.2023.100023.

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