Antioxidant and free radical scavenging potential of feruloyl amino acids and dipeptide derivatives: an experimental and theoretical investigation.

Authors

Imene Amine Khodja, Maciej Spiegel, Abdelaaty Hamed, Souhir Abid, Majdi Abid, Sulaiman A Alsalamah, Massuo J Kato, Houssem Boulebd

Published in

RSC advances. Oct 13, 2026. Epub Oct 13, 2026.

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.

PMID:
42871512
Bibliographic data and abstract were imported from PubMed on 14 Oct 2026.

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