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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 -
Animal : An International Journal of... Sep 2021Butylated hydroxyanisole (BHA) is a synthetic antioxidant analogous of vitamin E. It is used as a preservative to prevent free radical-mediated oxidation in high-fat...
Butylated hydroxyanisole (BHA) is a synthetic antioxidant analogous of vitamin E. It is used as a preservative to prevent free radical-mediated oxidation in high-fat foods, and this study's objective was to investigate the effects of BHA on oxidative stress and apoptosis in addition to delineating its efficacy as a growth-promoting feed additive. 60 weaned male rabbits (V-line) were randomly divided into four equal groups: BHA0.0 (control), BHA50, BHA100, and BHA150, administered basal diets with 0.0, 50, 100, and 150 mg BHA/kg of feed for 60 days. Animals were examined for growth performance, markers of oxidative stress and apoptosis, and meat characteristics. Compared to the control group, rabbits receiving BHA-supplemented diets exhibited increases in BW and average daily gain (P < 0.01), where BHA50 and BHA100 groups showed increased muscle content of methionine aspartic acid, serine, and glutamine (P < 0.05). These two groups also exhibited elevated catalase and superoxide dismutase activities and diminished malondialdehyde levels in the liver. Butylated hydroxyanisole upregulated fatty acid synthase gene (FASN), especially in BHA100 animals. Bcl-2-associated X/B-celllymphoma-2 (Bax/Bcl-2) ratio significantly increased in animals receiving higher doses of BHA, and the weight of the liver significantly increased following BHA treatment. Supplementing growing rabbits with lower doses of dietary BHA may promote growth performance and meat quality via maintaining the redox balance. Hence, the 50-100 mg/kg may be recommended as a safe and still effective feed additive as well as an oxidative stress attenuator.
Topics: Animals; Antioxidants; Butylated Hydroxyanisole; Diet; Male; Meat; Oxidative Stress; Rabbits
PubMed: 34425485
DOI: 10.1016/j.animal.2021.100339 -
The transformation mechanism and eco-toxicity evaluation of butylated hydroxyanisole in environment.Ecotoxicology and Environmental Safety Feb 2022Butylated hydroxyanisole (BHA) is one of important phenolic antioxidants and its fate in the environment has attracted much attention in recent years. In this study, the...
Butylated hydroxyanisole (BHA) is one of important phenolic antioxidants and its fate in the environment has attracted much attention in recent years. In this study, the initial reactions of BHA with OH radicals, including 8 abstraction reactions and 6 addition reactions, were calculated. The lowest energy barrier of 3.20 kcal mol was found from the abstraction reaction on phenolic hydroxyl group. The reaction barriers of addition paths are in the range of 5.48-9.28 kcal mol, which are lower than those of the abstraction paths. The reaction rate constants were calculated by using transition state theory, and the rate constants are 8.12 × 10 M sand 4.76 × 10 M s for the H-abstraction and OH-addition reactions, respectively. Through the calculation of the subsequent reactions of the abs-H-TS and add-C-M it was found that BHA would be further transformed into 2-tert-Butyl-1,4-benzoquinone (TBQ), tert-butylhydroquinone (TBHQ) etc. in the aqueous phase, and the eco-toxicities of these transformed products of BHA in the aqueous phase were significantly increased comparing with that of the BHA and they are toxic to aquatic organism.
Topics: Antioxidants; Butylated Hydroxyanisole; Hydroquinones; Phenols
PubMed: 35026586
DOI: 10.1016/j.ecoenv.2022.113179 -
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 -
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 -
EFSA Journal. European Food Safety... Jul 2021Following a request from the European Commission, the Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) was asked to deliver a scientific...
Following a request from the European Commission, the Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) was asked to deliver a scientific opinion on the safety and efficacy of butylated hydroxy anisole (BHA) when used as a technological additive (antioxidant) in feed for cats. BHA is a waxy solid consisting for > 98.5% of the active substance, a mixture of 3--butyl-4-hydroxyanisole and 2--butyl-4-hydroxyanisole and is currently authorised for use in all animal species except in cats. In support of the safety of the additive for the target species, the applicant has submitted a tolerance study which demonstrated that BHA is tolerated by cats at a concentration up to 150 mg/kg complete feed. The additive should be considered a skin, eye irritant and a potential skin sensitiser. Exposure of the user via inhalation was considered unlikely; therefore, a risk is not expected. BHA is authorised as an antioxidant for food use at comparable use levels; therefore, no studies were required to demonstrate the efficacy of BHA as an antioxidant in complete feed for cats.
PubMed: 34295440
DOI: 10.2903/j.efsa.2021.6714 -
Regulatory Toxicology and Pharmacology... Apr 2021Tumor data from rodent bioassays are used for cancer hazard classification with wide-ranging consequences. This paper presents a case study of the synthetic antioxidant... (Review)
Review
Tumor data from rodent bioassays are used for cancer hazard classification with wide-ranging consequences. This paper presents a case study of the synthetic antioxidant butylated hydroxyanisole (BHA), which IARC classified as Group 2B ("possibly carcinogenic to humans") on the basis of forestomach tumors in rodents following chronic dietary exposure to high levels. IARC later determined that the mechanism by which BHA induces forestomach tumors is not relevant to humans; however, the classification has not been revoked. BHA was listed on California Proposition 65 as a direct consequence of the IARC classification, and there is widespread concern among consumers regarding the safety of BHA driven by the perception that it is a carcinogen. While many regulatory agencies have established safe exposure limits for BHA, the IARC classification and Proposition 65 listing resulted in the addition of BHA to lists of substances banned from children's products and products seeking credentials such as EPA's Safer Choice program, as well as mandatory product labeling. Classifications have consequences that many times pre-empt the ability to conduct an exposure-based risk-based assessment., It is imperative to consider human relevance of both the endpoint and exposure conditions as fundamental to hazard identification.
Topics: Animals; Antioxidants; Butylated Hydroxyanisole; Carcinogens; Food Additives; Food Supply; Humans; Risk Assessment
PubMed: 33556417
DOI: 10.1016/j.yrtph.2021.104887 -
Heliyon May 2021This study aims to evaluate the effects of preservatives on somatic cells of . For the evaluation of cytotoxicity, root meristems of were treated with 1000, 1500, 2000,...
This study aims to evaluate the effects of preservatives on somatic cells of . For the evaluation of cytotoxicity, root meristems of were treated with 1000, 1500, 2000, 2500 ppm concentration for 5, 10, 15 days. The root tips showed concentration dependent growth retardation in all the used concentrations, as well as root texture, also has been changed mitotic index, total protein content decreased and frequency of chromosomal aberrations increased after 5 days treatment. Additionally, the RAPD-PCR method was applied to evaluate genotoxicity and found the highest concentration (2500 ppm) was comparatively more distant to the control group. Results concluded that BHT and BHA showed positive results and cytotoxic.
PubMed: 34041400
DOI: 10.1016/j.heliyon.2021.e07055 -
Avicenna Journal of Phytomedicine 2023This review describes the antioxidant activity of flavonoids as a subgroup of polyphenols and a partial or entire substitute for synthetic antioxidants. (Review)
Review
OBJECTIVE
This review describes the antioxidant activity of flavonoids as a subgroup of polyphenols and a partial or entire substitute for synthetic antioxidants.
MATERIALS AND METHODS
All relevant databases were searched using the terms "Phytochemical", "Polyphenol", and "Flavonoid".
RESULTS
The oxidative reaction caused by free radicals is a reason for food spoilage, which causes unpleasant odor, loss of taste, and damaged tissues. The common antioxidants employed in foods include butylated hydroxyanisole, butylated hydroxytoluene, propyl gallate, and tert-butyl hydroquinone. Despite their high efficiency and potency, synthetic antioxidants have adverse effects on the human body, such as causing mutation and carcinogenicity. A whole and a group of them known as polyphenols possess high antioxidant activity. These compounds are potential antioxidants due to their capabilities such as scavenging free radicals, donating hydrogen atoms, and chelating metal cations. The antioxidant mechanism of action of flavonoids is transferring hydrogen atom to free radicals. Accordingly, the more the flavonoid structure makes the hydrogen transfer faster and easier, the more the flavonoid's antioxidant power will be. Therefore, the antioxidant activity of the flavonoids with hydroxyl groups in their structure is the highest among different flavonoids.
CONCLUSION
In addition to health promotion and some disease prevention effects, various investigations have indicated that flavonoids possess high antioxidant activity that is comparable with synthetic antioxidants. However, to be commercially available, these compounds should be extracted from a low-price source with a high-performance method.
PubMed: 37663389
DOI: 10.22038/AJP.2023.21774 -
Bioactive Materials Jun 2023Respiratory syncytial virus (RSV) is the most common cause of viral bronchiolitis among children worldwide, yet there is no vaccine for RSV disease. This study...
Respiratory syncytial virus (RSV) is the most common cause of viral bronchiolitis among children worldwide, yet there is no vaccine for RSV disease. This study investigates the potential of cube and sphere-shaped cerium oxide nanoparticles (CNP) to modulate reactive oxygen (ROS) and nitrogen (RNS) species and immune cell phenotypes in the presence of RSV infection and . Cube and sphere-shaped CNP were synthesized by hydrothermal and ultrasonication methods, respectively. Physico-chemical characterization confirmed the shape of sphere and cube CNP and effect of various parameters on their particle size distribution and zeta potential. results revealed that sphere and cube CNP differentially modulated ROS and RNS levels in J774 macrophages. Specifically, cube CNP significantly reduced RSV-induced ROS levels without affecting RNS levels while sphere CNP increased RSV-induced RNS levels with minimal effect on ROS levels. Cube CNP drove an M1 phenotype in RSV-infected macrophages by increasing macrophage surface expression of CD80 and CD86 with a concomitant increase in TNFα and IL-12p70, while simultaneously decreasing M2 CD206 expression. Intranasal administration of sphere and cube-CNP were well-tolerated with no observed toxicity in BALB/c mice. Notably, cube CNP preferentially accumulated in murine alveolar macrophages and induced their activation, avoiding enhanced uptake and activation of other inflammatory cells such as neutrophils, which are associated with RSV-mediated inflammation. In conclusion, we report that sphere and cube CNP modulate macrophage polarization and innate cellular responses during RSV infection.
PubMed: 36606255
DOI: 10.1016/j.bioactmat.2022.12.005