Issue 3, 2022

New insights into the competition between antioxidant activities and pro-oxidant risks of rosmarinic acid

Abstract

Direct and indirect antioxidant activities of rosmarinic acid (RA) based on HOO˙/CH3OO˙ radical scavenging and Fe(III)/Fe(II) ion chelation were theoretically studied using density functional theory at the M05-2X/6-311++G(2df,2p) level of theory. First, four antioxidant mechanisms including hydrogen atom transfer (HAT), radical adduct formation (RAF), proton loss (PL) and single electron transfer (SET) were investigated in water and pentyl ethanoate (PEA) phases. Regarding the free radical scavenging mechanism, HAT plays a decisive role with overall rate coefficients of 1.84 × 103 M−1 s−1 (HOO˙) and 4.49 × 103 M−1 s−1 (CH3OO˙) in water. In contrast to PL, RAF and especially SET processes, the HAT reaction in PEA is slightly more favorable than that in water. Second, the [Fe(III)(H2O)6]3+ and [Fe(II)(H2O)6]2+ ion chelating processes in an aqueous phase are both favorable and spontaneous especially at the O5, site-1, and site-2 positions with large negative ΔrG0 values and great formation constant Kf. Finally, the pro-oxidant risk of RA was also considered via the Fe(III)-to-Fe(II) complex reduction process, which may initiate Fenton-like reactions forming reactive HO˙ radicals. As a result, RA does not enhance the reduction process when ascorbate anions are present as reducing agents, whereas the pro-oxidant risk becomes remarkable when superoxide anions are found. The results encourage further attempts to verify the speculation using more powerful research implementations of the antioxidant activities of rosmarinic acid in relationship with its possible pro-oxidant risks.

Graphical abstract: New insights into the competition between antioxidant activities and pro-oxidant risks of rosmarinic acid

Supplementary files

Article information

Article type
Paper
Submitted
14 okt 2021
Accepted
11 dek 2021
First published
10 yan 2022
This article is Open Access
Creative Commons BY license

RSC Adv., 2022,12, 1499-1514

New insights into the competition between antioxidant activities and pro-oxidant risks of rosmarinic acid

D. H. Truong, T. C. Ngo, N. T. A. Nhung, D. T. Quang, T. L. A. Nguyen, D. Khiri, S. Taamalli, F. Louis, A. El Bakali and D. Q. Dao, RSC Adv., 2022, 12, 1499 DOI: 10.1039/D1RA07599C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements