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

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

doi:10.1039/d1ra07599c

Cited by 17 publications

(31 citation statements)

References 95 publications

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“…Meanwhile, the ones in the bi-dentate complexes range from 2.11 to 2.56 Å and from 2.15 to 2.54 Å, respectively. As reported by previous works, the interaction distances in Fe(III) complexes are shorter than those in Fe(II) ones [24][25][26][27]. Cartesian coordinates and the thermochemistry data of all the Fe-Leu complexes are displayed in electronic supplementary material, table SI2.…”

Section: Fe Ions Chelationmentioning

confidence: 71%

“…The pro-oxidant risks of l -leucine are evaluated via the reduction reactions of Fe(III)-to-Fe(II)-Leu complexes and Cu(II)-to-Cu(I)-Leu complexes that may promote the production of reactive HO· radical by Fenton reactions [ 25 , 26 , 32 ]. Thermodynamic and kinetic data of the reduction reactions by two reducing agents, i.e.…”

Section: Resultsmentioning

confidence: 99%

“…The structures of [Fe(H 2 O) 6 ] 3+ , [Fe(H 2 O) 6 ] 2+ , [Cu(H 2 O) 4 ] 2+ and [Cu(H 2 O) 4 ] + were employed as recommended by previous works [ 23 – 26 ]. In this study, the high-spin states of hydrated Fe(II) and Fe(III) ions being 5 and 6, respectively, were used as recommended by several works in the literature [ 25 – 30 ].…”

Section: Methodsmentioning

confidence: 99%

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Oxidation of l -leucine amino acid initiated by hydroxyl radical: are transition metal ions an enhancement factor?

et al. 2022

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Hydroxyl radical (HO·) formation initiated by the Fenton-type reactions of Fe and Cu complexes of l -leucine (Leu) amino acid as well as its oxidation reaction by HO· was computationally investigated by using the density functional theory method at the M05-2X/6-311++G(3df,2pd)//M05-2X/6-311++G(d,p) level of theory in the aqueous phase. The results showed that dipole-salt is the main form of Leu in the physiological condition. Leu exhibits high chelating potential towards both Fe(III)/Fe(II) and Cu(II)/Cu(I) ions with the most favourable coordinating positions at two oxygen atoms of the –COO functional group. Furthermore, the Leu-ions complexes show a high risk of HO· formation via Fenton-like reactions, especially when ascorbate anion exists in the environment as a reducing agent. Finally, the oxidation reaction of l -leucine by HO· demonstrated a relatively high overall apparent reaction rate, k overall , being 1.18 × 10 9 M −1 s −1 , in which formal hydrogen transfer reactions of the dipole-salt form occur as the primary mechanism. Consequently, the Leu oxidation by HO· radical can be promoted by the Fenton reaction enhancement of its transition metal complexes.

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Section: Fe Ions Chelationmentioning

confidence: 71%

Section: Resultsmentioning

confidence: 99%

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Oxidation of l -leucine amino acid initiated by hydroxyl radical: are transition metal ions an enhancement factor?

et al. 2022

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“…32,33 The influence of the aqueous media was mimicked by combining the implicit solvation model based on density (SMD) [34][35][36] and the polarizable continuum model (PCM), which several works have widely used in the literature. 37,38 ] + were employed as a recommendation by previous works. [38][39][40][41][42] The high-spin states of hydrated Fe(II) and Fe(III) ions in this study were equal to 5 and 6, respectively.…”

Section: Methodsmentioning

confidence: 99%

Influence of transition metal ions on the oxidation of L-proline amino acid initiated by HO● radical in the aqueous phase

Dao

Truong

Nguyen

2022

Preprint

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The oxidation of L-proline (Pro) amino acid by HO • radical and the influence of transition metal ions on this process have been investigated by using the density functional theory (DFT) method at the M05-2X/6-311++G(3df,3pd)//M05-2X/6-311++G(d,p) level of theory in the aqueous phase. The results show that Pro can be oxidized by HO • radical via formal hydrogen transfer (FHT) reactions at multiple sites, with the highest branching ratio found at hydrogen atoms H10 (30.04%) and H12 (25.60%). The overall rate constant at 298.15K is determined as 6.04 × 10 8 M -1 s -1 , and its expression from 250 to 400K is k=1.634×T 2.990 ×exp[1.591(kcal mol -1 )/RT] M -1 s -1 . In addition, Pro tends to form the stable mono-and bidentate complexes with both Fe and Cu ions via the-COO functional group of dipole-salt form, which significantly increases when the concentration of Pro doubles. The most stable Cu(II)-Pro complexes have high potential oxidant risks by enhancing the HO • radical formation when reducing agents such as superoxide anion, or ascorbate anion are available. Besides, the oxidant reaction of the high oxidation state complexes, including Fe(III)-Pro and Cu(II)-Pro, by HO • radical as FHT reactions have a lower rate constant than that of free-ligand, while the ones for SET reactions is extremely low even though they are higher than that of free-ligand. As a result, the Pro's oxidation enhancement of these complexes is negligible. In contrast, the rate constants of SET reactions of low oxidation state complexes (i.e., Fe(II)-Pro and Cu(I)-Pro) are likely to be many times faster than the oxidation rate of free ligand, and thus, these complexes promote the oxidation of Pro. Finally, the FHT chemical nature of HO-initiated oxidation for free Pro, Fe(III)-Pro, and Cu(II)-Pro complexes are evaluated to determine whether these processes occur via hydrogen atom transfer (HAT) or proton-coupled electron transfer (PCET).

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“…Many studies have confirmed that RA has strong antioxidant properties [ 7 ]. Due to the current consumer concerns about the safety of synthetic preservatives, plant extracts rich in polyphenols such as RA are increasingly being used to extend the shelf life of food and cosmetics [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

In Vitro Strategy for the Enhancement of the Production of Bioactive Polyphenols in Transformed Roots of Salvia bulleyana

Krzemińska

Owczarek

Olszewska

et al. 2022

IJMS

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The underground parts of Salvia bulleyana, a rare Chinese plant species, have long been used in traditional Chinese medicine. The Rhizobium rhizogenes-transformed root culture obtained from this plant might be a promising novel source of valuable phenolics, including rosmarinic acid. The present study identifies for the first time, the optimal growth conditions of S. bulleyana hairy roots regarding production efficiency. The comprehensive optimization comprised cultivation in different basal media (B5, SH, MS, and WP) with full- and half-strength macro- and microelements, different vitamin contents (full, half, one-quarter part, and without) and sucrose concentrations (2, 3, 4, 5%), and under different light conditions: in dark, under blue LED (λ = 430 nm), red LED (λ = 670 nm), mixed blue and red LED (30%:70%), and white LED (390–670 nm). Hairy root growth and bioactive compound accumulation were also detailed every five days over the 50-day culture cycle. The optimal conditions were determined using a technique for order preference by similarity to the ideal solution (TOPSIS). The most efficient combination for root growth and polyphenol content was found to be ½SH liquid medium with half vitamin concentration and 3% sucrose when grown in the dark. The biomass yield during the growth cycle was 6.1 g (fresh weight—FW) and 0.92 g (dry weight—DW) on one Erlenmeyer flask: a 14.3-fold increase in FW and 16.1-fold increase in DW in relation to the inoculum. The highest mean total phenolic content was 93.6 mg/g DW including about 70 mg/g DW rosmarinic acid, reached on day 40 of culture; compared to roots of two-year-old plants grown under field conditions, the total phenolic acid content was four times higher and rosmarinic acid eight times higher. The obtained results place the investigated culture among the best hair root cultures for rosmarinic acid production.

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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.

Cited by 17 publications

References 95 publications

Oxidation of l -leucine amino acid initiated by hydroxyl radical: are transition metal ions an enhancement factor?

Oxidation of l -leucine amino acid initiated by hydroxyl radical: are transition metal ions an enhancement factor?

Influence of transition metal ions on the oxidation of L-proline amino acid initiated by HO● radical in the aqueous phase

In Vitro Strategy for the Enhancement of the Production of Bioactive Polyphenols in Transformed Roots of Salvia bulleyana

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