Insights on the kinetics and mechanisms of the peroxyl radical scavenging capacity of caftaric acid: the important role of the acid–base equilibrium

Boulebd, Houssem; Mechler, Ádám; Hòa, Nguyễn Thị; Vo, Quan V.

doi:10.1039/d2nj00377e

Cited by 9 publications

(11 citation statements)

References 54 publications

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“…Moreover, it is worth noting that the overall rate constants of 5-CQA and 5-FQA are comparable to that of the reference antioxidant ascorbic acid (k = 9.97 × 10 7 M −1 s −1 ) [ 25 ] and the structurally similar system caftaric acid (k = 9.09 × 10 8 M −1 s −1 ) [ 61 ] but higher than that of Trolox (1.13 × 10 5 M −1 s −1 ) [ 63 ], BHT (2.51 × 10 5 M −1 s −1 ) [ 64 ], carnosic acid (k = 4.73 × 10 6 M −1 s −1 ) [ 65 ], and cannabidiol (k = 9.09 × 10 6 M −1 s −1 ) [ 66 ]. This indicates that 5-CQA and 5-FQA are potent antiradical agents under polar physiological conditions.…”

Section: Resultsmentioning

confidence: 98%

Exploring the Antioxidant Properties of Caffeoylquinic and Feruloylquinic Acids: A Computational Study on Hydroperoxyl Radical Scavenging and Xanthine Oxidase Inhibition

Boulebd,

Carmena-Bargueño,

Pérez-Sánchez

2023

Antioxidants

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Caffeoylquinic (5-CQA) and feruloylquinic (5-FQA) acids, found in coffee and other plant sources, are known to exhibit diverse biological activities, including potential antioxidant effects. However, the underlying mechanisms of these phenolic compounds remain elusive. This paper investigates the capacity and mode of action of 5-CQA and 5-FQA as natural antioxidants acting as hydroperoxyl radical scavengers and xanthine oxidase (XO) inhibitors. The hydroperoxyl radical scavenging potential was investigated using thermodynamic and kinetic calculations based on the DFT method, taking into account the influence of physiological conditions. Blind docking and molecular dynamics simulations were used to investigate the inhibition capacity toward the XO enzyme. The results showed that 5-CQA and 5-FQA exhibit potent hydroperoxyl radical scavenging capacity in both polar and lipidic physiological media, with rate constants higher than those of common antioxidants, such as Trolox and BHT. 5-CQA carrying catechol moiety was found to be more potent than 5-FQA in both physiological environments. Furthermore, both compounds show good affinity with the active site of the XO enzyme and form stable complexes. The hydrogen atom transfer (HAT) mechanism was found to be exclusive in lipid media, while both HAT and SET (single electron transfer) mechanisms are possible in water. 5-CQA and 5-FQA may, therefore, be considered potent natural antioxidants with potential health benefits.

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Section: Resultsmentioning

confidence: 98%

Exploring the Antioxidant Properties of Caffeoylquinic and Feruloylquinic Acids: A Computational Study on Hydroperoxyl Radical Scavenging and Xanthine Oxidase Inhibition

Boulebd,

Carmena-Bargueño,

Pérez-Sánchez

2023

Antioxidants

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“…Previous studies indicated that the addition reaction into the α,β-unsaturated bond had no contributions to the ROO˙ radical ( i.e. , HOO˙ and CH 3 OO˙) scavenging activity, particularly in the physiological environments, 19,24,63 and RAF reaction is not supported for the π system of aromatic rings. 64,65 Thus, this reaction was omitted in our study.…”

Section: Resultsmentioning

confidence: 93%

The radical scavenging activity of monocaffeoylquinic acids: the role of neighboring hydroxyl groups and pH levels

Vo,

Thuy Hoa,

Hoa

et al. 2024

RSC Adv.

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“…In the context of antioxidant activity, deprotonated forms potentially play a key role in the mechanism underlying the interaction of PBs with free radicals. 21 Therefore, all deprotonated forms of PBs were considered in the thermodynamic and kinetic investigations of HOO • radical scavenging.…”

Section: Resultsmentioning

confidence: 99%

“…Derivatives C, D, and E with the catechol moiety react mainly via FHT from the deprotonated state, which is in agreement with previous studies on phenolic compounds containing the catechol moiety, as quercetins, 29 5-O-methylnorbergenin, 30 anthocyanidins, 31 and caftaric acid. 21 On the other hand, for F, which has two OH bonds in the para position, both SET and FHT are possible, mainly in equal ratios.…”

Section: Thermodynamic Evaluation In Physiological Mediamentioning

confidence: 99%

Mechanistic Insights into the Antioxidant and Pro-oxidant Activities of Bromophenols from Marine Algae: A DFT Investigation

Boulebd

2024

J. Org. Chem.

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Marine algae are a rich source of aromatic secondary metabolites, with bromophenols (BPs) receiving particular attention due to their health benefits. Despite extensive research on BPs, the understanding of their antioxidant potential, as well as their mechanisms of action at the molecular level, remains incomplete. This study utilized density functional theory (DFT) to systematically elucidate the antioxidant and pro-oxidant mechanisms of the main BP scaffolds under physiological conditions. It was found that BPs exhibit potent antioxidant capacity in both polar and lipid environments. In lipid media, the formal hydrogen transfer mechanism has been identified as the exclusive antiradical pathway. The position of bromine atoms significantly influenced the activity, particularly in scaffolds containing one hydroxyl group. However, no significant effect was observed in scaffolds with two hydroxyl groups. In water, monodeprotonated BPs showed key radical scavenging activity, with different mechanisms favored depending on the configuration of the hydroxyl groups. Additionally, BPs, particularly those bearing a catechol moiety, exhibit secondary antioxidant activity by reducing the production of hydroxyl radicals via the ascorbic acid anion pathway. These findings provide further validation of the potent antioxidant properties of BPs and shed light on their mechanism of action in physiological environments.

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Insights on the kinetics and mechanisms of the peroxyl radical scavenging capacity of caftaric acid: the important role of the acid–base equilibrium

Abstract: Caftaric acid (CA), also known as cafeoyltartaric acid, is a molecule formed by linking caffeic acid (3,4-dihydroxy cinnamic acid) and tartaric acid through an ester moiety. This compound is found...

Cited by 9 publications

References 54 publications

Exploring the Antioxidant Properties of Caffeoylquinic and Feruloylquinic Acids: A Computational Study on Hydroperoxyl Radical Scavenging and Xanthine Oxidase Inhibition

Exploring the Antioxidant Properties of Caffeoylquinic and Feruloylquinic Acids: A Computational Study on Hydroperoxyl Radical Scavenging and Xanthine Oxidase Inhibition

The radical scavenging activity of monocaffeoylquinic acids: the role of neighboring hydroxyl groups and pH levels

Mechanistic Insights into the Antioxidant and Pro-oxidant Activities of Bromophenols from Marine Algae: A DFT Investigation

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