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

Truong, Dinh Hieu ; Ngo, Thi Chinh ; Nhung, Nguyen Thi Ai ; Quang, Duong Tuan ; Nguyen, Thi Le Anh ; Khiri, Dorra ; Taamalli, Sonia ; Louis, Florent ; El Bakali, Abderrahman ; Dao, Duy Quang

RSC advances, 2022-01, Vol.12 (3), p.1499-1514 [Periódico revisado por pares]

England: Royal Society of Chemistry

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  • Título:
    New insights into the competition between antioxidant activities and pro-oxidant risks of rosmarinic acid
  • Autor: Truong, Dinh Hieu ; Ngo, Thi Chinh ; Nhung, Nguyen Thi Ai ; Quang, Duong Tuan ; Nguyen, Thi Le Anh ; Khiri, Dorra ; Taamalli, Sonia ; Louis, Florent ; El Bakali, Abderrahman ; Dao, Duy Quang
  • Assuntos: Anions ; Antioxidants ; Chelation ; Chemical Sciences ; Chemistry ; Density functional theory ; Electron transfer ; Free radicals ; Oxidizing agents ; Reducing agents ; Rosmarinic acid ; Scavenging ; Single electrons
  • É parte de: RSC advances, 2022-01, Vol.12 (3), p.1499-1514
  • Notas: 10.1039/d1ra07599c
    Electronic supplementary information (ESI) available. See DOI
    ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
    PMCID: PMC8978883
  • Descrição: Direct and indirect antioxidant activities of rosmarinic acid (RA) based on HOO&z.rad;/CH 3 OO&z.rad; 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 × 10 3 M −1 s −1 (HOO&z.rad;) and 4.49 × 10 3 M −1 s −1 (CH 3 OO&z.rad;) 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 )(H 2 O) 6 ] 3+ and [Fe( ii )(H 2 O) 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 Δ r 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&z.rad; 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. Direct and indirect antioxidant activities of rosmarinic acid (RA) based on HOO&z.rad;/CH 3 OO&z.rad; 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.
  • Editor: England: Royal Society of Chemistry
  • Idioma: Inglês
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