Computational study of the hydrogen peroxide scavenging mechanism of allyl methyl disulfide, an antioxidant compound from garlic

Vega-Hissi, Esteban G.; Andrada, Matías F.; Díaz, Mario G.; Martínez, Juan C. Garro

doi:10.1007/s11030-019-09927-6

Cited by 15 publications

(15 citation statements)

References 46 publications

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“… 152 − 154 On the other hand, several researchers who used both B3LYP and one of Truhlar’s global hybrids noted that while B3LYP tends to underestimate energies there are no substantial differences and the reactivity patterns hold when the same basis set is used. 60 , 64 , 95 , 123 , 127 …”

Section: Preliminary Concernsmentioning

confidence: 99%

“… 200 Also a solvent may also affect the final result. 124 Some studies propose stockholder charge partitioning approaches in this purpose, particularly Hirschfeld analysis, 15 , 64 , 123 since it yields values for which condensed Fukui functions correlate well with the expected data. In fact, a “dual descriptor” better illustrates susceptibility for electrophilic–nucleophilic attack, 206 but these types of reactions are beyond the scope of antiradical activity studies.…”

Section: Electronic Structure Investigationsmentioning

confidence: 99%

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Current Trends in Computational Quantum Chemistry Studies on Antioxidant Radical Scavenging Activity

Spiegel

2022

J. Chem. Inf. Model.

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The antioxidative nature of chemicals is now routinely studied using computational quantum chemistry. Scientists are constantly proposing new approaches to investigate those methods, and the subject is evolving at a rapid pace. The goal of this review is to collect, consolidate, and present current trends in a clear, methodical, and reference-rich manner. This paper is divided into several sections, each of which corresponds to a different stage of elaborations: preliminary concerns, electronic structure analysis, and general reactivity (thermochemistry and kinetics). The sections are further subdivided based on methodologies used. Concluding remarks and future perspectives are presented based on the remaining elements.

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Section: Preliminary Concernsmentioning

confidence: 99%

Section: Electronic Structure Investigationsmentioning

confidence: 99%

Current Trends in Computational Quantum Chemistry Studies on Antioxidant Radical Scavenging Activity

Spiegel

2022

J. Chem. Inf. Model.

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“…Superoxide (·O 2 ), hydrogen peroxide (H 2 O 2 ), and the extremely reactive hydroxyl radical (·OH) are formed in a sequential univalent process in which O 2 undergoes reduction . Thus, cells under aerobic conditions are threatened by these ROS, which are efficiently removed by the powerful antioxidant systems of the cell without any untoward effects . When the antioxidant mechanisms are unable to cope with ROS production, oxidative stress results.…”

Section: Biological Functions Of Sulfur-containing Spice Compoundsmentioning

confidence: 99%

Functional Application of Sulfur-Containing Spice Compounds

Xie

Liao

Tang

2020

J. Agric. Food Chem.

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Sulfur-containing spice compounds possess diverse biological functions and play an important role in food, chemicals, pharmaceuticals, and agriculture. The development of functional spices has become increasingly popular, especially for medicinal functions for dietary health. Thus, this review focuses on the properties and functions of sulfur-containing spice compounds, including antioxidant, anti-inflammatory, antiobesity, anticancer, antibacterial, and insecticidal functions, among others. Developments over the last five years concerning the properties of sulfur-containing spice compounds are summarized and discussed.

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“…Previously, we carried out computational studies of the thermodynamic and kinetics aspect of allyl methyl disulfide (AMD) with hydrogen peroxide and hydroxyl radical . In addition, several authors have published theoretical and experimental studies of the reaction of the antioxidants compounds focused in the elimination of ROS species, which highlight the actual interest on this issue .…”

Section: Introductionmentioning

confidence: 99%

“…Previously, we carried out computational studies of the thermodynamic and kinetics aspect of allyl methyl disulfide (AMD) with hydrogen peroxide and hydroxyl radical. [15][16][17] In addition, several authors have published theoretical and experimental studies of the reaction of the antioxidants compounds focused in the elimination of ROS species, which highlight the actual interest on this issue. [18][19][20][21][22][23] Here, we research the scavenging mechanism of hydrogen peroxide by two garlic active compounds: Allyl Methyl Sulfide (AMS) and Diallyl Sulfide (DAS).…”

Section: Introductionmentioning

confidence: 99%

Scavenging of Hydrogen Peroxide by Allyl Methyl Sulfide and Diallyl Sulfide, Two Garlic Active Compounds: A Theoretical Study

et al. 2020

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We study potential scavenging of hydrogen peroxide by Allyl Methyl Sulfide and Diallyl Sulfide, two garlic components. The antioxidant properties of garlic are attributed to organosulfide compounds, which react with reactive oxygen species preventing the oxidative stress. We used the B3LYP functional for structure analysis and M06‐2X functional for the reactions employing gaseous, aqueous and non‐polar environments. The conformational analysis and Fukui functions allowed the selection of the initial structures and the region of nucleophilic attack by hydrogen peroxide. The scavenging reactions analyzed are: 1) Sulfoxidation; 2) Epoxidation; and 3) Hydrogenation. Through the intrinsic reaction coordinate, the energy profile, the activation energies, the rate constant and its temperature‐dependence were calculated. The results predict that reactions occur slowly and hydrogenation is not a feasible process. Finally, the sulfoxidation of Allyl Methyl Sulfide and Diallyl Sulfide resulted to be more thermodynamically and kinetically favorable than epoxidation (rate constant values, 10−10 s−1, in comparison with 10−18 s−1 from epoxidation), becoming the most probable pathway for hydrogen peroxide scavenging.

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Computational study of the hydrogen peroxide scavenging mechanism of allyl methyl disulfide, an antioxidant compound from garlic

Cited by 15 publications

References 46 publications

Current Trends in Computational Quantum Chemistry Studies on Antioxidant Radical Scavenging Activity

Current Trends in Computational Quantum Chemistry Studies on Antioxidant Radical Scavenging Activity

Functional Application of Sulfur-Containing Spice Compounds

Scavenging of Hydrogen Peroxide by Allyl Methyl Sulfide and Diallyl Sulfide, Two Garlic Active Compounds: A Theoretical Study

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