Antioxidant and free radical scavenging potential of feruloyl amino acids and dipeptide derivatives: an experimental and theoretical investigation
6 affiliations
- 1Laboratory of Synthesis of Molecules with Biological Interest, University of Frères Mentouri Constantine 1 Constantine 25017 Algeria
- 2Department of Organic Chemistry and Pharmaceutical Technology, Faculty of Pharmacy, Wroclaw Medical University Wroclaw 50-556 Poland
- 3Chemistry Department, Faculty of Science, Al-Azhar University Nasr City-Cairo 11884 Egypt
- 4Department of Chemistry, College of Science, Jouf University Sakaka Aljouf 72341 Saudi Arabia
- 5Department of Biology, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU) Riyadh 11623 Saudi Arabia
- 6Institute of Chemistry, University of São Paulo Av.Prof.Lineu Prestes, 748 São Paulo 05508-000 SP Brazil
Abstract
Feruloyl amino acids and their corresponding dipeptide derivatives, obtained via condensation of ferulic acid—a well-established natural antioxidant—with amino acids and dipeptide moieties, represent a class of compounds with notable biological potential. In the present study, the antioxidant activity and radical-scavenging potential of a series of twelve feruloyl amino acid and dipeptide derivatives were systematically investigated using both in vitro assays and computational methods. Experimental evaluation was performed using DPPH˙ and ABTS˙+ assays. In the DPPH˙ assay, several derivatives exhibited EC50 values lower than those of the reference antioxidants BHA and BHT, whereas in the ABTS˙+ assay, all synthesized compounds displayed EC50 values below 1 µg mL−1, markedly outperforming both reference antioxidants. Quantum chemical calculations further supported these findings by elucidating the mechanisms underlying their antioxidant properties. Thermodynamic and kinetic analyses of hydroperoxyl (HOO˙) radical scavenging under simulation of aqueous conditions representative of a physiological environment demonstrated highly favorable reaction pathways, as well as significant metal-chelation capacity. Both feruloyl amino acids and their dipeptide derivatives showed high radical-scavenging activity in aqueous media, primarily via the single-electron transfer (SET) mechanism, with rate constants on the order of 106 to 107 M−1 s−1. In addition, these compounds demonstrated strong chelation ability toward Cu(ii) ions, predominantly through a bidentate coordination mode. These findings indicate that feruloyl amino acids and their dipeptide derivatives are potent antioxidants with potential therapeutic relevance.
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BibTeX
@article{khodja2026antioxidant,
title = {{Antioxidant and free radical scavenging potential of feruloyl amino acids and dipeptide derivatives: an experimental and theoretical investigation}},
author = {Imene Amine Khodja and Maciej Spiegel and Abdelaaty Hamed and Souhir Abid and Majdi Abid and Sulaiman A. Alsalamah and Massuo J. Kato and Houssem Boulebd},
journal = {RSC advances},
year = {2026},
month = oct,
doi = {10.1039/d6ra03650c},
url = {https://europepmc.org/article/PMC/PMC13659655},
note = {CC BY-NC},
}
RIS
TY - JOUR
TI - Antioxidant and free radical scavenging potential of feruloyl amino acids and dipeptide derivatives: an experimental and theoretical investigation
AU - Imene Amine Khodja
AU - Maciej Spiegel
AU - Abdelaaty Hamed
AU - Souhir Abid
AU - Majdi Abid
AU - Sulaiman A. Alsalamah
AU - Massuo J. Kato
AU - Houssem Boulebd
PY - 2026
DA - 2026/10/13
JO - RSC advances
DO - 10.1039/d6ra03650c
UR - https://europepmc.org/article/PMC/PMC13659655
AB - Feruloyl amino acids and their corresponding dipeptide derivatives, obtained via condensation of ferulic acid—a well-established natural antioxidant—with amino acids and dipeptide moieties, represent a class of compounds with notable biological potential. In the present study, the antioxidant activity and radical-scavenging potential of a series of twelve feruloyl amino acid and dipeptide derivatives were systematically investigated using both in vitro assays and computational methods. Experimental evaluation was performed using DPPH˙ and ABTS˙+ assays. In the DPPH˙ assay, several derivatives exhibited EC50 values lower than those of the reference antioxidants BHA and BHT, whereas in the ABTS˙+ assay, all synthesized compounds displayed EC50 values below 1 µg mL−1, markedly outperforming both reference antioxidants. Quantum chemical calculations further supported these findings by elucidating the mechanisms underlying their antioxidant properties. Thermodynamic and kinetic analyses of hydroperoxyl (HOO˙) radical scavenging under simulation of aqueous conditions representative of a physiological environment demonstrated highly favorable reaction pathways, as well as significant metal-chelation capacity. Both feruloyl amino acids and their dipeptide derivatives showed high radical-scavenging activity in aqueous media, primarily via the single-electron transfer (SET) mechanism, with rate constants on the order of 106 to 107 M−1 s−1. In addition, these compounds demonstrated strong chelation ability toward Cu(ii) ions, predominantly through a bidentate coordination mode. These findings indicate that feruloyl amino acids and their dipeptide derivatives are potent antioxidants with potential therapeutic relevance.
SN - 2046-2069
ER -