Unraveling the antioxidant potential of thiamine: Thermochemical and kinetics studies in aqueous phase using DFT

Nga, Nguyễn Thị; Dao, Duy Quang

doi:10.1002/vjch.201900081

Cited by 11 publications

(6 citation statements)

References 10 publications

(12 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In comparison with the lowest BDEs of other potential antioxidant like α-terpinene (74.4 kcal mol −1 in the gas phase), thiamine (85.7, 88.3, and 86.7 kcal mol −1 ), 89 Trolox (76.6, 78.4, and 76.6 kcal mol −1 ), and ascorbic acid (73.4, 79.0, and 74.5 kcal mol −1 ) calculated at the same computational approaches in the gas phase, water, and PEA, respectively, compounds C3, C4, and C5 represent promising antioxidants via the HT process.…”

Section: Preliminary Evaluation Of Antioxidant Potential Via Dpphmentioning

confidence: 99%

Insight into Antioxidant and Photoprotective Properties of Natural Compounds from Marine Fungus

Dao

Phan

Nguyen

et al. 2020

J. Chem. Inf. Model.

View full text Add to dashboard Cite

This computational and experimental work aims to elucidate physicochemical and photophysical natures of free radical scavenging and ultraviolet radiation (UVR) filtering activities of five terpenoids available in the extract of marine fungus. The antioxidant activities of ochraceopone F (C1), aspertetranone D (C2), cycloechinulin (C3), wasabidienone E (C4), and mactanamide (C5) are evaluated by using density functional theory (DFT) at the M05-2X/6-311++G(d,p) level of theory in the gas phase, water, and pentyl ethanoate (PEA). Double antioxidant mechanisms allowing the second (H + /e − ) donation such as double hydrogen atom transfer (dHAT), double single electron transfer-proton transfer (dSET-PT), and double sequential proton loss-electron transfer (dSPL-ET) are considered. Reaction enthalpies (Δ r H 0 ), standard Gibbs free energies (Δ r G 0 ) and potential energy surfaces of reactions toward HOO • radical are then established to evaluate the hydrogen transfer (HT) and radical adduct formation (RAF) mechanisms. The computational results are supported by DPPH • and ABTS •+ antioxidant essays. Results show that all compounds C1−C5 are able to scavenge two free radicals via dHAT, dSET-PT, and dSPL-ET mechanisms. Among the compounds, C3 and C4 represent the most potential antioxidants, especially via HAT and RAF mechanisms in all the reaction media. Their rate constants for both HAT and RAF reactions are remarkably higher than that of Trolox and ascorbic acid. The kinetic calculations on activation Gibbs free energies (ΔG ⧧ ) and rate constants (k TST ) based on conventional transition state theory (TST) reveal that HAT and RAF processes are in competition in solvents. Photophysical processes occurring during UVR exposure are investigated using the time dependent density functional theory (TD-DFT) combined with UV−vis experiments. The obtained results highlight the promising activities of C1−C5 in UVR absorption in the ranges of UVA and UVB. Among them, C3 and C4 also show better UV absorption properties with the easiest excitations (band gaps equal to 4.06 and 3.65 eV). This study suggests the natural candidates possibly used in organic sunscreen.

show abstract

Section: Preliminary Evaluation Of Antioxidant Potential Via Dpphmentioning

confidence: 99%

Insight into Antioxidant and Photoprotective Properties of Natural Compounds from Marine Fungus

Dao

Phan

Nguyen

et al. 2020

J. Chem. Inf. Model.

View full text Add to dashboard Cite

show abstract

“…Enthalpies and Gibbs free energies of four common antioxidant reactions, i.e., formal hydrogen transfer (FHT), proton transfer (PT), single electron transfer (SET) and radical adduct formation (RAF), have been calculated but in the aqueous phase. The results showed that in comparing with trolox and ascorbic acid, their antioxidant potential has been classified in the decreasing order: ascorbic acid > thiamine > trolox [13]. Preliminary studies indicated the existence of certain correlations between the activity of antioxidants and the content of vitamins [14,15,16].…”

Section: Introductionmentioning

confidence: 99%

The Effect of Thiamine Concentration on the Antioxidative Activity Indices in Tea Extracts

et al. 2019

View full text Add to dashboard Cite

The aim of the study was to determine correlations between the concentration of thiamine in systems and indicators of the antioxidative activity of ethanol tea extracts in the presence of soybean oil. Variability of the thiamine form was assumed by comparison of the influence of thiamine hydrochloride or thiamine pyrophosphate and fermentation of ethanol tea extracts. The study provides practical knowledge about the antioxidative activity of ethanol tea extracts in products containing fat and thiamine. The study showed that all tea extracts exhibited higher antioxidative activity in the presence of thiamine amounts of 0.1 and 0.8 mg/100 g. The antioxidative activity of ethanol tea extracts was significantly reduced when the concentrations were higher than the natural level for foods (over 1.0 mg/100 g). The systems containing white tea extract were the most vulnerable, whereas those with black tea were the least vulnerable. The presence of thiamine pyrophosphate in the system was more strongly correlated with reduced activity of the extracts than the presence of thiamine hydrochloride.

show abstract

“…In addition to the metabolic and structural function, thiamine has also demonstrated antioxidant properties. Thiamine as scavenger of ROS removes hydroxyl (HO • ) radical significantly higher than hydroperoxyl radical (HOO • ) [ 113 ].…”

Section: The Antioxidant Protective Role Of Thiaminementioning

confidence: 99%

The importance of thiamine (vitamin B1) in humans

et al. 2023

View full text Add to dashboard Cite

Thiamine (thiamin, B1) is a vitamin necessary for proper cell function. It exists in a free form as a thiamine, or as a mono-, di- or triphosphate. Thiamine plays a special role in the body as a coenzyme necessary for the metabolism of carbohydrates, fats and proteins. In addition, it participates in the cellular respiration and oxidation of fatty acids: in malnourished people, high doses of glucose result in acute thiamine deficiency. It also participates in energy production in the mitochondria and protein synthesis. In addition, it is also needed to ensure the proper functioning of the central and peripheral nervous system, where it is involved in neurotransmitter synthesis. Its deficiency leads to mitochondrial dysfunction, lactate and pyruvate accumulation, and consequently to focal thalamic degeneration, manifested as Wernicke's encephalopathy or Wernicke-Korsakoff syndrome. It can also lead to severe or even fatal neurologic and cardiovascular complications, including heart failure, neuropathy leading to ataxia and paralysis, confusion, or delirium. The most common risk factor for thiamine deficiency is alcohol abuse. This paper presents current knowledge of the biological functions of thiamine, its antioxidant properties, and the effects of its deficiency in the body.

show abstract

Unraveling the antioxidant potential of thiamine: Thermochemical and kinetics studies in aqueous phase using DFT

Cited by 11 publications

References 10 publications

Insight into Antioxidant and Photoprotective Properties of Natural Compounds from Marine Fungus

Insight into Antioxidant and Photoprotective Properties of Natural Compounds from Marine Fungus

The Effect of Thiamine Concentration on the Antioxidative Activity Indices in Tea Extracts

The importance of thiamine (vitamin B1) in humans

Contact Info

Product

Resources

About