New insights into the competition between antioxidant activities and pro-oxidant risks of rosmarinic acid
This journal is © The Royal Society of Chemistry..
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 Δr G 0 values and great formation constant K f. 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.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:12 |
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| Enthalten in: |
RSC advances - 12(2022), 3 vom: 05. Jan., Seite 1499-1514 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Truong, Dinh Hieu [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 16.04.2022 published: Electronic-eCollection Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/d1ra07599c |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a 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 Δr G 0 values and great formation constant K f. 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 | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Ngo, Thi Chinh |e verfasserin |4 aut | |
| 700 | 1 | |a Nhung, Nguyen Thi Ai |e verfasserin |4 aut | |
| 700 | 1 | |a Quang, Duong Tuan |e verfasserin |4 aut | |
| 700 | 1 | |a Nguyen, Thi Le Anh |e verfasserin |4 aut | |
| 700 | 1 | |a Khiri, Dorra |e verfasserin |4 aut | |
| 700 | 1 | |a Taamalli, Sonia |e verfasserin |4 aut | |
| 700 | 1 | |a Louis, Florent |e verfasserin |4 aut | |
| 700 | 1 | |a El Bakali, Abderrahman |e verfasserin |4 aut | |
| 700 | 1 | |a Dao, Duy Quang |e verfasserin |4 aut | |
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