Sesamol is a related antioxidant to the vitamin E

Palheta, Ivanete Cardoso; Borges, Rosivaldo S.

doi:10.1016/j.cdc.2017.08.004

Cited by 13 publications

(11 citation statements)

References 15 publications

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“…40−42 Sesamol also induces nitric oxide (the most important vascular relaxing factor) release from endothelial cells. 28,43 It has scavenging effects against hydroxyl (OH • ), superoxide anion (O 2 •− ), nitric oxide, hydrogen peroxide (H 2 O 2 ), and other oxidants, 44−47 in some cases with an efficiency higher, or equal to those of ascorbic acid 48 and vitamin E. 49 Based on its free radical scavenging activity, it has been suggested to use sesamol in the management of Huntington's, Alzheimer's, and Parkinson's diseases, auto-immunity disorders, and brain damage in autism. 50−54 The interesting properties of sesamol have motivated investigations on the possible applications of its derivatives for different purposes.…”

Section: Introductionmentioning

confidence: 99%

“…One of the most widely studied properties of sesamol is its antioxidant activity. − It has been proved to have effective capacity for inhibiting hydroxyl radical-induced deoxyribose degradation and lipid peroxidation ,− which helps protecting plasma, low-density lipoprotein, and erythrocyte membrane from oxidation. − Sesamol also induces nitric oxide (the most important vascular relaxing factor) release from endothelial cells. , It has scavenging effects against hydroxyl (OH • ), superoxide anion (O 2 •– ), nitric oxide, hydrogen peroxide (H 2 O 2 ), and other oxidants, − in some cases with an efficiency higher, or equal to those of ascorbic acid and vitamin E . Based on its free radical scavenging activity, it has been suggested to use sesamol in the management of Huntington’s, Alzheimer’s, and Parkinson’s diseases, auto-immunity disorders, and brain damage in autism. − …”

Section: Introductionmentioning

confidence: 99%

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Computationally Designed Sesamol Derivatives Proposed as Potent Antioxidants

2020

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Oxidative stress has been recognized to play an important role in several diseases, such as Parkinson’s and Alzheimer’s disease, which justifies the beneficial effects of antioxidants in ameliorating the deleterious effects of these health disorders. Sesamol, in particular, has been investigated for the treatment of several conditions because of its antioxidant properties. This article reports a rational computational design of new sesamol derivatives. They were constructed by adding four functional groups (−OH, −NH2, −COOH, and −SH) in three different positions of the sesamol molecular framework. A total of 50 derivatives between mono-, di-, and trisubstituted compounds were obtained. All the derivatives were evaluated and compared with a reference set of commercial neuroprotective drugs. The estimated properties are absorption, distribution, metabolism, excretion, toxicity, and synthetic accessibility. Selection and elimination scores were used to choose a first set of promising candidates. Acid-based properties and reactivity indexes were then estimated using the density functional theory. Four sesamol derivatives were finally selected, which are hypothesized to be potent antioxidants, even better than sesamol and Trolox for that purpose.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Computationally Designed Sesamol Derivatives Proposed as Potent Antioxidants

2020

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“…The relationship between chemical structure and antioxidant capacity relationship was compared using the double zeta and triple zeta B3LYP/6-311++G(2d,2p) at the computational level [16][17][18][19]. Excellent results were previously reported for sesamol-related derivatives [11,20,21]. All molecular calculations, including the visualization of the spin density distribution, were achieved using Gaussian 09 [22].…”

Section: Methodsmentioning

confidence: 99%

“…Antioxidant activity basically involves several mechanisms; among them, the most important are the single electron transfer (SET) and the hydrogen atom transfer (HAT) to a free radical, generating a derivative or intermediate radical neutralized by the resonance of an aromatic ring [8,9]. These mechanisms have already been connected to the antioxidant action of sesamol and its derivatives through the diphenyl picrylhydrazyl radical (DPPH) [10] with a reduced theoretical capacity when compared to tocopherol derivatives [11]. Therefore, this work aimed to increase the antioxidant capacity of sesamol by alkylation (2-8, 13, and 14) inspired by tocopherol derivatives and classic antioxidants such as trolox 9, t-butylated hydroxytoluene 10 (BHT), and t-butylated hydroxyanisole 11 and 12 (BHA) ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Alkylated Sesamol Derivatives as Potent Antioxidants

et al. 2020

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Sesamol is a phenolic derivative. Its antioxidant activity is low than that of Trolox and depends on benzodioxole moiety. Thus, a molecular modification strategy through alkylation, inspired by natural and synthetic antioxidants, was studied by molecular modeling at the DFT/B3LYP level of theory by comparing the 6-31+G(d,p) and 6-311++G(2d,2p) basis sets. All proposed derivatives were compared to classical related antioxidants such as Trolox, t-butylated hydroxytoluene (BHT) and t-butylated hydroxyanisole (BHA). According to our results, molecular orbitals, single electron or hydrogen-atom transfers, spin density distributions, and alkyl substitutions at the ortho positions related to phenol moiety were found to be more effective than any other positions. The trimethylated derivative was more potent than Trolox. t-Butylated derivatives were stronger than all other alkylated derivatives and may be new alternative forms of modified antioxidants from natural products with applications in the chemical, pharmaceutical, and food industries.

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“…In addition, tocopherols are present in sesame oil. As is known from studies [17], sesamol is a synergist of tocopherols, and therefore these substances can be considered as a complex antioxidant. In addition, the aforementioned scientific papers [13,14] describe the positive effects of adding the developed PFM to the confectionery product (cream sweets) for the rational nutrition of athletes.…”

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confidence: 99%

Research on oxidative stability of protein-fat mixture based on sesame and flax seeds for use in halva technology

Belinska¹,

Bochkarev²,

Varankina³

et al. 2019

EEJET

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products of lipid-protein composition for special purposes, that is, for nutrition of certain segments of populationchildren, athletes, pregnant women, the elderly, etc. The composition of such protein-fat mixtures (PFM) is consis-1. Introduction The newest and most promising direction in the oil and fat industry is development and production of combined TECHNOLOGY AND EQUIPMENT OF FOOD PRODUCTION

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Sesamol is a related antioxidant to the vitamin E

Cited by 13 publications

References 15 publications

Computationally Designed Sesamol Derivatives Proposed as Potent Antioxidants

Computationally Designed Sesamol Derivatives Proposed as Potent Antioxidants

Alkylated Sesamol Derivatives as Potent Antioxidants

Research on oxidative stability of protein-fat mixture based on sesame and flax seeds for use in halva technology

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