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Molecules (Basel, Switzerland) Jul 2020Sesamol is a phenolic derivative. Its antioxidant activity is low than that of Trolox and depends on benzodioxole moiety. Thus, a molecular modification strategy through...
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, -butylated hydroxytoluene (BHT) and -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. -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.
Topics: Alkylation; Antioxidants; Benzodioxoles; Butylated Hydroxyanisole; Butylated Hydroxytoluene; Chromans; Electron Transport; Free Radicals; Molecular Structure; Phenols
PubMed: 32708143
DOI: 10.3390/molecules25143300 -
Molecules (Basel, Switzerland) Mar 2022The annual production of cocoa is approximately 4.7 million tons of cocoa beans, of which only 10% corresponds to the cocoa bean and the remaining value corresponds to a... (Review)
Review
The annual production of cocoa is approximately 4.7 million tons of cocoa beans, of which only 10% corresponds to the cocoa bean and the remaining value corresponds to a high number of residues, cocoa bean shell, pulp and husk. These by-products are a source of nutrients and compounds of notable interest in the food industry as possible ingredients, or even additives. The assessment of such by-products is relevant to the circular economy at both environmental and economic levels. Investigations carried out with these by-products have shown that cocoa husk can be used for the production of useful chemicals such as ketones, carboxylic acids, aldehydes, furans, heterocyclic aromatics, alkylbenzenes, phenols and benzenediols, as well as being efficient for the removal of lead from acidic solutions, without decay in the process due to the other metals in this matrix. The fibre present in the cocoa bean shell has a considerable capacity to adsorb a large amount of oil and cholesterol, thus reducing its bioavailability during the digestion process, as well as preventing lipid oxidation in meats, with better results compared to synthetic antioxidants (butylated hydroxytoluene and β-tocopherol). Finally, cocoa pulp can be used to generate a sweet and sour juice with a natural flavour. Thus, this review aimed to compile information on these by-products, focusing mainly on their chemical and nutritional composition, simultaneously, the various uses proposed in the literature based on a bibliographic review of articles, books and theses published between 2000 and 2021, using databases such as Scopus, Web of Science, ScieLO, PubMed and ResearchGate.
Topics: Chocolate
PubMed: 35268725
DOI: 10.3390/molecules27051625 -
Antioxidants (Basel, Switzerland) Apr 2022-butyl curcumin (TBC), demethylated -butylated curcumin (1E,6E-1,7-bis(3--butyl-4,5-dihydroxyphenyl)hepta-1,6-diene-3,5-dione, DMTC), demethylated curcumin (DMC), and...
-butyl curcumin (TBC), demethylated -butylated curcumin (1E,6E-1,7-bis(3--butyl-4,5-dihydroxyphenyl)hepta-1,6-diene-3,5-dione, DMTC), demethylated curcumin (DMC), and Cur were synthesized from the starting compound, 2-methoxy-4-methylphenol. TBC and DMTC are two novel lipophilic compounds, and Cur and DMC are polar and hydrophilic. The antioxidant activities of Cur, TBC, DMC, and DMTC were evaluated by using the methods of 2,2-diphenyl-1-(2,4,6-trinitro-phenyl)-hydrazinyl (DPPH), deep-frying, and Rancimat. -butylhydroquinone (TBHQ) and Butylated hydroxytoluene (BHT) were used as comparison compounds. Both Rancimat and deep-frying tests demonstrated that DMTC was the strongest antioxidant, and TBC also had stronger antioxidant activity than Cur. In the DPPH assay, DMC showed the highest scavenging activity, followed by DMTC, TBHQ, Cur, and TBC. DMTC and TBC can be potentially used as strong antioxidants in food industry, especially for frying, baking, and other high temperature food processing. DMTC is the strongest antioxidant in oil to our knowledge.
PubMed: 35453481
DOI: 10.3390/antiox11040796 -
Environmental Health Perspectives Jun 2023Diminished/decreased ovarian reserve (DOR) is a disorder of ovarian function, which severely affects women's reproductive health. Accumulating evidence has found that...
BACKGROUND
Diminished/decreased ovarian reserve (DOR) is a disorder of ovarian function, which severely affects women's reproductive health. Accumulating evidence has found that adverse environmental factors can affect ovarian function. However, whether synthetic phenolic antioxidants (SPAs) exposure is associated with DOR is still unknown.
OBJECTIVES
We explored whether concentrations of SPAs and their metabolites are associated with DOR.
METHODS
A case-control study was conducted from January 2019 to January 2020 in China. One hundred eighty-one women 20-44 years of age, with (case group, ) and without DOR (control group, ) were included in our study. The follicular fluid concentrations of typical SPAs and their metabolites were measured, including butylated hydroxyanisole (BHA), -butylhydroquinone (TBHQ), butylated hydroxytoluene (BHT), and five BHT metabolites [3,5-di--butyl-4-hydroxy-benzylalcohol (BHT-OH), 3,5-di--butyl-4-hydroxybenzaldehyde (BHT-CHO), 3,5-di--butyl-4-hydroxybenzoic acid (BHT-COOH), 2,6-di--butyl-1,4-benzoquinone (BHT-Q), and 2,6-di--butyl-4-hydroxy-4-methylcyclohexa-2,5-dien-1-one (BHT-quinol)]. Information about serum basal concentrations of follicle-stimulating hormone (FSH), luteinizing hormone (LH), estradiol (E2), and anti-Müllerian hormone (AMH) and the basal antral follicle count (AFC) was collected.
RESULTS
The measured frequencies of BHA, TBHQ, BHT, BHT-OH, BHT-CHO, BHT-COOH, BHT-Q, and BHT-quinol in follicular fluid were 1.7%, 2.2%, 40.3%, 46.4%, 57.5%, 100%, 64.6%, and 49.2%, respectively. The concentrations of BHT-CHO ( vs. , ), BHT-COOH ( vs. , ), BHT-Q ( vs. , ), and the sum of five BHT metabolites (; vs. , ) in the case group were significantly higher than those in the control group. The risk of DOR was further analyzed according to the tertiles of chemical concentration. Compared with the low levels of BHT metabolites, the adjusted odds ratios (ORs) for DOR were significantly increased in the high levels of BHT-CHO [, 95% confidence interval (CI): 1.22, 8.31, ], BHT-COOH [ (95% CI: 1.63, 13.71), ], and BHT-Q [ (95% CI: 1.69, 11.86), ] after adjusting for age, body mass index, education, infertility type, triglycerides, and total cholesterol. Moreover, compared with the low level of , increased adjusted ORs for DOR were found both in the middle level [ (95% CI: 1.44, 11.75), ] and high level [ (95% CI: 1.81, 16.77), ], showing an obvious dose-response relationship ().
CONCLUSION
In this study, we report the measured frequency and concentrations of BHA, TBHQ, BHT, and their metabolites in follicular fluid. Moreover, we found the concentrations of BHT metabolites, especially BHT-CHO, BHT-COOH, and BHT-Q, are positively associated with the increased risk of DOR. https://doi.org/10.1289/EHP11309.
Topics: Female; Humans; Antioxidants; Hydroquinones; Case-Control Studies; Follicular Fluid; Ovarian Reserve; Phenols
PubMed: 37267061
DOI: 10.1289/EHP11309 -
Toxicology Reports 2021Earlier reports have shown that Cyclophosphamide (CYCP), an anti-malignant drug, elicited cytotoxicity; and that naringin has several beneficial potentials against...
Earlier reports have shown that Cyclophosphamide (CYCP), an anti-malignant drug, elicited cytotoxicity; and that naringin has several beneficial potentials against oxidative stress and dyslipidaemias. We investigated the influence of naringin on free radical scavenging, cellular integrity, cellular ATP, antioxidants, oxidative stress, and lipid profiles in the CYCP-induced erythrocytotoxicity rat model. Rats were pretreated orally by gavage for fourteen consecutive days with three doses (50, 100, and 200 mg/kg) naringin before single CYCP (200 mg/kg, i.p.) administration. Afterwards, the rats were sacrificed. Naringin concentrations required for 50 % scavenging hydrogen peroxide and nitric oxide radical were 0.27 mg/mL and 0.28 mg/mL, respectively. Naringin pretreatment significantly (p < 0.05) protected erythrocytes plasma membrane architecture and integrity by abolishing CYCP-induced decrease in the activity of erythrocyte LDH (a marker of ATP). Pretreatment with naringin remarkably (p < 0.05) reversed CYCP-induced decreases in the erythrocytes glutathione levels, activities of glutathione-S-transferase, catalase, glutathione peroxidase, and glutathione reductase; attenuated CYCP-mediated increases in erythrocytes levels of malondialdehyde, nitric oxide, and major lipids (cholesterol, triacylglycerol, phospholipids, and non-esterified fatty acids). Taken together, different acute pretreatment doses of naringin might avert CYCP-mediated erythrocytes dysfunctions its antioxidant, free-radical scavenging, and anti-dyslipidaemia properties.
PubMed: 34760624
DOI: 10.1016/j.toxrep.2021.10.011 -
ACS Omega Jun 2022In order to cut off the chain reaction in the process of coal oxidation at low temperature (COLT), butylated hydroxytoluene (BHT) was used as an inhibitor to explore its...
In order to cut off the chain reaction in the process of coal oxidation at low temperature (COLT), butylated hydroxytoluene (BHT) was used as an inhibitor to explore its inhibition effect and mechanism. In this paper, in situ Fourier transform infrared spectroscopy, electron paramagnetic resonance, and gas production of COLT experiments were conducted to compare the inhibited coal sample (BHT-Coal) with the raw coal. The results showed that BHT can effectively inhibit the formation of active free radicals, reduce the content of active alkoxy, carbonyl, and hydroxyl groups, increase the production temperature of CO, CO, and CH, and reduce the concentration. The crossing point temperature increased from 132.3 to 157.4 °C, indicating that BHT can reduce the spontaneous combustion tendency of the raw coal. To explore the inhibition mechanism of BHT on COLT, five typical active free-radical models were established, and their active sites, active bonds, and thermodynamic parameters were calculated according to the density functional theory. The results showed that the highly active H atoms of the phenolic hydroxyl group in BHT can combine with active free radicals to generate stable compounds, and the activation energy of each reaction is small, which can occur under normal temperature and pressure. The inhibition mechanism of BHT is to reduce the concentration of the free radicals, so as to weaken the chain reaction strength during the COLT. This study provides a reference for the development and utilization of inhibitors.
PubMed: 35694513
DOI: 10.1021/acsomega.2c01229 -
Molecules (Basel, Switzerland) Sep 2022Magnofluorine, a secondary metabolite commonly found in various plants, has pharmacological potential; however, its antioxidant and enzyme inhibition effects have not...
Magnofluorine, a secondary metabolite commonly found in various plants, has pharmacological potential; however, its antioxidant and enzyme inhibition effects have not been investigated. We investigated the antioxidant potential of Magnofluorine using bioanalytical assays with 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), ,-dimethyl--phenylenediamine dihydrochloride (DMPD), and 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging abilities and K[Fe(CN)] and Cu reduction abilities. Further, we compared the effects of Magnofluorine and butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), α-Tocopherol, and Trolox as positive antioxidant controls. According to the analysis results, Magnofluorine removed 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals with an IC value of 10.58 μg/mL. The IC values of BHA, BHT, Trolox, and α-Tocopherol were 10.10 μg/mL, 25.95 μg/mL, 7.059 μg/mL, and 11.31 μg/mL, respectively. Our results indicated that the DPPH· scavenging effect of Magnofluorine was similar to that of BHA, close to that of Trolox, and better than that of BHT and α-tocopherol. The inhibition effect of Magnofluorine was examined against enzymes, such as acetylcholinesterase (AChE), α-glycosidase, butyrylcholinesterase (BChE), and human carbonic anhydrase II (hCA II), which are linked to global disorders, such as diabetes, Alzheimer's disease (AD), and glaucoma. Magnofluorine inhibited these metabolic enzymes with Ki values of 10.251.94, 5.991.79, 25.411.10, and 30.563.36 nM, respectively. Thus, Magnofluorine, which has been proven to be an antioxidant, antidiabetic, and anticholinergic in our study, can treat glaucoma. In addition, molecular docking was performed to understand the interactions between Magnofluorine and target enzymes BChE (D: 6T9P), hCA II (A:3HS4), AChE (B:4EY7), and α-glycosidase (C:5NN8). The results suggest that Magnofluorine may be an important compound in the transition from natural sources to industrial applications, especially new drugs.
Topics: Acetylcholinesterase; Antioxidants; Aporphines; Biphenyl Compounds; Butylated Hydroxyanisole; Butylated Hydroxytoluene; Butyrylcholinesterase; Carbonic Anhydrase II; Cholinergic Antagonists; Cholinesterase Inhibitors; Glaucoma; Glycoside Hydrolases; Humans; Hypoglycemic Agents; Molecular Docking Simulation; Picrates; Sulfonic Acids; alpha-Tocopherol
PubMed: 36144638
DOI: 10.3390/molecules27185902 -
Archives of Razi Institute Dec 2021The current experiment aimed to assess the effect of the synthetic antioxidants ethoxyquin (EQ) and/or butylated hydroxytoluene (BHT) on the liver function tests,...
The current experiment aimed to assess the effect of the synthetic antioxidants ethoxyquin (EQ) and/or butylated hydroxytoluene (BHT) on the liver function tests, hematological parameters, and liver histoarchitecture in rats. A total of 50 male Sprague-Dawley rats were divided into five groups of 10 animals per group. The first group served as the control and did not receive any treatments, and the second group served as the vehicle control and was orally administrated 1 ml of corn oil day after day for consecutive 45 and 90 days. The third group (EQ) was orally administered 1 ml of EQ dissolved in corn oil day after day for consecutive 45 and 90 days in a dose of 1/5 LD, and the fourth group (BHT) was orally received 1 ml of BHT dissolved in corn oil day after day for consecutive 45 and 90 days in a dose of 1/5 LD. The fifth group (combination group) was orally administered both EQ and BHT at the same doses and durations described above. The present results showed that the final body weight was significantly decreased in the EQ- or BHT-treated group particularly at 90 days of exposure to both compounds. Furthermore, the liver weight was significantly elevated in EQ, BHT, and co-exposed groups at 45 and 90 days of exposure, compared to the control group. Moreover, EQ, BHT, and their co-exposure caused a significant elevation in the levels of alanine aminotransferase (ALT) and aspartate aminotransferase (AST) enzymes, as well as total bilirubin at 45 and 90 days of exposure. On the other hand, there was no significant change in the total albumin. Hemoglobin value, red blood cells, white blood cells, platelets, and differential leucocyte count at 45 and 90 days of exposure were significantly decreased. Histopathological significant findings in the liver were observed as vascular congestions, vacuolations, hydropic degenerations, lipidosis, and swelling, particularly in the co-exposed group for 90 days. These findings confirmed the hepatotoxic potential of EQ and BHT; therefore, it is recommended to control and limit the utilization of such chemicals.
Topics: Animals; Butylated Hydroxytoluene; Corn Oil; Ethoxyquin; Liver; Male; Rats; Rats, Sprague-Dawley; Toluene
PubMed: 35546987
DOI: 10.22092/ari.2021.356439.1844 -
Frontiers in Plant Science 2020The activity of polarly localized PIN-FORMED (PIN) auxin efflux carriers contributes to the formation of auxin gradients which guide plant growth, development, and...
The activity of polarly localized PIN-FORMED (PIN) auxin efflux carriers contributes to the formation of auxin gradients which guide plant growth, development, and tropic responses. Both the localization and abundance of PIN proteins in the plasma membrane depend on the regulation of PIN trafficking through endocytosis and exocytosis and are influenced by many external and internal stimuli, such as reactive oxygen species, auxin transport inhibitors, flavonoids and plant hormones. Here, we investigated the regulation of endosomal PIN cycling by using a Brefeldin A (BFA) assay to study the effect of a phenolic antioxidant ionol, butylated hydroxytoluene (BHT), on the endocytosis and exocytosis of PIN1 and PIN2. BHT is one of the most widely used antioxidants in the food and feed industries, and as such is commonly released into the environment; however, the effect of BHT on plants remains poorly characterized. Preincubation of Arabidopsis seedlings with BHT before BFA treatment strongly enhanced the internalization of PIN1 into BFA compartments. After the simultaneous application of BHT and NAA, the NAA effect dominated PIN internalization suggesting the BHT effect occurred downstream to that of NAA. Washing seedlings with BHT after BFA treatment prevented the release of PIN1 from BFA compartments back to the plasma membrane, indicating that BHT application inhibited PIN1 exocytosis. Overall rates of PIN2 internalization were less pronounced than those of PIN1 in seedlings pre-incubated with BHT before BFA treatment, and PIN2 exocytosis was not inhibited by BHT, indicating a specific activity of BHT on PIN1 exocytosis. Comparison of BHT activity with other potential stimuli of PIN1 and PIN2 trafficking [e.g., HO (ROS), salt stress, reduced glutathione (GSH), dithiothreitol (DTT), and flavonoids] showed that BHT has a new activity distinct from the activities of other regulators of PIN trafficking. The findings support BHT as a potentially interesting pharmacological tool for dissecting PIN trafficking and auxin transport.
PubMed: 32322261
DOI: 10.3389/fpls.2020.00393 -
Journal of Environmental and Public... 2019Air fresheners contain various chemicals that may or may not be harmful to human health and the environment. These products are widely used in different settings such as...
Air fresheners contain various chemicals that may or may not be harmful to human health and the environment. These products are widely used in different settings such as homes, schools, offices, and hospitals with ignorance of their real ingredients and their relative health effects. Thus, this preliminary study was carried out to identify the presence of different compounds in spray air fresheners that were not disclosed on the product's label. Four different brands of spray air fresheners were selected randomly from a local store, in which two were of mid-to-high cost and the remaining two of low cost. The samples were analyzed using gas chromatography/mass spectrometry headspace, in which single components of the samples were identified by the mass spectrometry detector. The results were shown as a chromatogram of several peaks, each representing different compounds. The chemicals found in the samples include; lilial, galaxolide, benzenemethanol, musk ketone, butylated hydroxytoluene, and linalool. These chemicals may cause irritation and other health problems. However, none of them were revealed on the product's label. The study concludes that air fresheners need to be free of any toxic or harmful chemicals and include natural ingredients instead.
Topics: Aerosols; Air Pollutants; Consumer Product Safety; Deodorants; Gas Chromatography-Mass Spectrometry; Household Products; Humans; Product Labeling
PubMed: 31781257
DOI: 10.1155/2019/9316707