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Journal of the Science of Food and... Oct 2023Butylated hydroxyanisole (BHA) is mainly used as a food additive due to its antioxidant properties, which prevent or delay oxidation reactions and extend the storage... (Review)
Review
Butylated hydroxyanisole (BHA) is mainly used as a food additive due to its antioxidant properties, which prevent or delay oxidation reactions and extend the storage life of products. The widespread use of BHA has led to its extensive presence in various environmental matrices and human tissues. Food intake is the main route of human exposure to BHA. Under different conditions, BHA can produce different metabolites, with tert-butyl hydroquinone (TBHQ) being one of the major products. Several studies have shown that BHA could cause thyroid system damage, metabolic and growth disorders, neurotoxicity, and carcinogenesis. Mechanisms such as endocrine disruption, genotoxicity, disturbances of energy metabolism, reactive oxygen species (ROS) production, signaling pathways, and imbalances in calcium homeostasis appear to be associated with the toxic effects of BHA. Avoiding the toxic effects of BHA to the maximum extent possible is a top priority. Finding safe, non-toxic and environmentally friendly alternatives to BHA should be the focus of subsequent research. In all, this review summarized the current situation related to BHA and might make recommendations for future research directions. © 2023 Society of Chemical Industry.
Topics: Humans; Butylated Hydroxyanisole; Antioxidants; Oxidation-Reduction; Food Additives; Reactive Oxygen Species
PubMed: 37127924
DOI: 10.1002/jsfa.12676 -
International Journal of Toxicology Dec 2023The Expert Panel for Cosmetic Ingredient Safety reviewed updated information that has become available since their original assessment from 2002, along with updated...
The Expert Panel for Cosmetic Ingredient Safety reviewed updated information that has become available since their original assessment from 2002, along with updated information regarding product types, and frequency and concentrations of use, and reaffirmed their original conclusion that BHT is safe as a cosmetic ingredient in the practices of use and concentration as described in this report.
Topics: Butylated Hydroxytoluene; Butylated Hydroxyanisole; Antioxidants; Cosmetics
PubMed: 37751543
DOI: 10.1177/10915818231204256 -
Food and Chemical Toxicology : An... Jun 2024Butylated hydroxyanisole (BHA) is one of the most commonly used antioxidants and is widely used in food, but whether it causes vascular damage has not been clearly...
Butylated hydroxyanisole (BHA) is one of the most commonly used antioxidants and is widely used in food, but whether it causes vascular damage has not been clearly studied. The present study demonstrated for the first time that BHA reduced the viability of human umbilical vein endothelial cells (HUVECs) and mouse brain microvascular endothelial cells (BEND3) in a dose- and time-dependent manner. Moreover, BHA inhibited the migration and proliferation of vascular endothelial cells (ECs). Further analysis revealed that in ECs, the ferroptosis inhibitor ferrostatin-1 (Fer-1) reversed the BHA-induced increase in Fe and malonaldehyde (MDA) levels. Acridine orange staining demonstrated that BHA increased lysosomal permeability. At the protein level, BHA increased the expression of transcription factor EB (TFEB) and decreased the expression of glutathione peroxidase (GPX4), solute carrier family 7 member 11 (SLC7A11, xCT), and ferritin heavy chain 1 (FTH1). Moreover, these effects of BHA could be reversed by knocking down TFEB. In vivo experiments confirmed that BHA caused elevated pulse wave velocity (PWV) and reduced acetylcholine-dependent vascular endothelial diastole. In conclusion, BHA degrades GPX4, xCT, and FTH1 through activation of the TFEB-mediated lysosomal pathway and promotes ferroptosis, ultimately leading to vascular endothelial cell injury.
Topics: Animals; Humans; Mice; Phospholipid Hydroperoxide Glutathione Peroxidase; Butylated Hydroxyanisole; Human Umbilical Vein Endothelial Cells; Basic Helix-Loop-Helix Leucine Zipper Transcription Factors; Amino Acid Transport System y+; Ferroptosis; Cell Proliferation; Endothelial Cells; Cell Movement; Ferritins; Cyclohexylamines; Oxidoreductases; Phenylenediamines
PubMed: 38657941
DOI: 10.1016/j.fct.2024.114682 -
Scientific Reports Feb 2024Butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA) are two antioxidants that have been extensively used in many applications. Both are well known for...
Spectrofluorimetric determination of butylated hydroxytoluene and butylated hydroxyanisole in their combined formulation: application to butylated hydroxyanisole residual analysis in milk and butter.
Butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA) are two antioxidants that have been extensively used in many applications. Both are well known for their debatable health risks due to their multiple intake sources. Therefore, conservative limits are set for them in different regulations adapted to the matrices in which they exist. Here we present a simple spectrofluorimetric method for the determination of BHT and BHA based on their native fluorescence and synchronous scanning mode. The type of solvent and the interval between emission and excitation wavelengths were carefully optimized. Under the optimized conditions, good linearities were obtained between the emission intensity and the corresponding concentrations of BHT and BHA over the range of 3-18 µg/mL and 0.1-7 µg/mL, respectively with a good correlation coefficient (r > 0.99). The limits of detection were 0.9 and 0.02 µg/mL, and the quantification limits were 3 and 0.05 µg/mL for BHT and BHA, respectively. The suggested procedure was validated according to ICH guidelines Q2 (R1). Furthermore, the method's greenness was assessed by three different methods, and it proved to be eco-reasonable. The method was successfully applied to the determination of BHT and BHA in pharmaceutical formulations. We also applied the suggested method for monitoring the residual BHA in conventional, powdered milk and butter, with good recovery in spiked samples.
Topics: Animals; Butylated Hydroxytoluene; Butylated Hydroxyanisole; Milk; Butter; Spectrometry, Fluorescence; Antioxidants
PubMed: 38402246
DOI: 10.1038/s41598-024-54483-1 -
Toxics Jan 2024Butylated hydroxyanisole (BHA), a synthetic phenolic antioxidant (SPA), is now widely present in natural waters. To improve the degradation efficiency of BHA and reduce...
Butylated hydroxyanisole (BHA), a synthetic phenolic antioxidant (SPA), is now widely present in natural waters. To improve the degradation efficiency of BHA and reduce product toxicity, a combination of peroxymonosulfate (PMS) and Ferrate(VI) (Fe(VI)) was used in this study. We systematically investigated the reaction kinetics, mechanism and product toxicity in the degradation of BHA through the combined use of PMS and Fe(VI). The results showed that PMS and Fe(VI) have synergistic effects on the degradation of BHA. The effects of operational factors, including PMS dosage, pH and coexisting ions (Cl, SO, HCO, K, NH and Mg), and different water matrices were investigated through a series of kinetic experiments. When T = 25 °C, the initial pH was 8.0, the initial BHA concentration was 100 μM, the initial concentration ratio of [PMS]:[Fe(VI)]:[BHA] was 100:1:1 and the degradation rate could reach 92.4% within 30 min. Through liquid chromatography time-of-flight mass spectrometry (LC-TOF-MS) identification, it was determined that the oxidation pathway of BHA caused by PMS/Fe(VI) mainly includes hydroxylation, ring-opening and coupling reactions. Density functional theory (DFT) calculations indicated that OH was most likely to attack BHA and generate hydroxylated products. The comprehensive comparison of product toxicity results showed that the PMS/Fe(VI) system can effectively reduce the environmental risk of a reaction. This study contributes to the development of PMS/Fe(VI) for water treatment applications.
PubMed: 38251010
DOI: 10.3390/toxics12010054 -
Journal of Chromatographic Science May 2024Mayonnaise is an emulsion of oil that is susceptible to lipid oxidation, which can cause spoilage and the formation of harmful compounds. This study aims to evaluate the...
Mayonnaise is an emulsion of oil that is susceptible to lipid oxidation, which can cause spoilage and the formation of harmful compounds. This study aims to evaluate the impact of Syrian apple and grape vinegar on the oxidative stability of mayonnaise and compare the use of natural antioxidants to synthetic ones such as butylated hydroxyanisole and butylated hydroxytoluene. The study measured total phenol content, radical scavenging activity, and identified some phenolic compounds by High Performance Liquid Chromatography (HPLC). The rancidity of mayonnaise was examined using peroxide value and thiobarbituric acid number. The fatty acids content in the mayonnaise samples was examined using gas chromatography. Vinegar samples containing high concentrations of phenolic antioxidants showed high ability to scavenge free radicals. The antioxidants in vinegar protected the mayonnaise samples from primary and secondary oxidation, and there was no statistically significant difference between the ratio of unsaturated fatty acids in the samples containing vinegar at the beginning and at the end of the storage period. The study shows the significance of using vinegar to protect mayonnaise from deterioration and increase its shelf life, in addition to its role as a dressing.
Topics: Acetic Acid; Oxidation-Reduction; Antioxidants; Chromatography, High Pressure Liquid; Phenols; Fatty Acids; Food Storage; Malus
PubMed: 37224456
DOI: 10.1093/chromsci/bmad036 -
Molecules (Basel, Switzerland) Aug 2023Sebsebe (Celestraceae) is a naturally growing shrub in Oman. It is not a reputed medicinal plant in Oman, but it is regionally endemic and causes shivering attacks on...
Sebsebe (Celestraceae) is a naturally growing shrub in Oman. It is not a reputed medicinal plant in Oman, but it is regionally endemic and causes shivering attacks on goats that graze on it. The chemical investigation of the hexane and chloroform extracts of the fruits and stems of afforded dihydro-β-agarofuran-type sesquiterpene pyridine alkaloid (), lupanyl myristoate () and lignanolactone (). Compounds (-) are new isolates from . The structures of these compounds were assigned through comprehensive IR, NMR, and ESI-MS analyses, and the relative configurations of compounds and were deduced from density function theory (DFT) calculations and NMR experiments. Compound was assayed against the kinase enzyme and showed no inhibition activity for p38 alpha and delta at a 10 µM test concentration. Compound inhibited the 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH) by 69.5%, compared to 70.9% and 78.0% for gallic acid and butylated hydroxyanisole, respectively, which were used as positive controls.
Topics: Animals; Maytenus; Biological Assay; Butylated Hydroxyanisole; Chloroform; Fruit; Goats
PubMed: 37630328
DOI: 10.3390/molecules28166077 -
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 -
Journal of Biomolecular Structure &... Aug 2023A series of new heteroleptic oxovanadium(IV) complexes with the general formula [VOL(Dcf)] (), where L = thiosemicarbazone (TSC)-based ligands and Dcf = diclofenac...
Theoretical, antioxidant, antidiabetic and molecular docking and pharmacokinetics studies of heteroleptic oxovanadium(IV) complexes of thiosemicarbazone-based ligands and diclofenac.
A series of new heteroleptic oxovanadium(IV) complexes with the general formula [VOL(Dcf)] (), where L = thiosemicarbazone (TSC)-based ligands and Dcf = diclofenac have been synthesized and characterized. The spectral studies along with the density functional theory calculations evidenced the distorted square-pyramidal geometry around oxovanadium(IV) ion through imine nitrogen and thione sulfur atoms of TSC moiety, and two asymmetric carboxylate oxygen atoms of diclofenac drug. The complexes were evaluated for antioxidant activity using 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), 2,2'-diphenyl-1-picrylhydrazyl (DPPH), hydrogen peroxide (HO) and superoxide radical scavenging assays with respect to the standard antioxidant drugs butylated hydroxyanisole (BHA) and rutin. The antidiabetic activity of the complexes was tested with enzymes such as α-amylase, α-glucosidase and glucose-6-phosphatase. The complexes containing methyl substituent showed higher activity than that containing the nitro substituent due to the electron-donating effect of methyl group. The molecular docking studies of the oxovanadium(IV) complexes with α-amylase and α-glucosidase enzymes showed strong interaction hydrogen bonding and hydrophobic interactions. The dynamic behavior of the proposed complexes was analyzed by molecular dynamics (MDs) simulations, which revealed the stability of docked structures with α-amylase and α-glucosidase enzymes. The physicochemical and pharmacokinetics parameters, such as Lipinski's 'rule of five', Veber's rule and absorption, distribution, metabolism and excretion (ADME) properties predicted non-toxic, non-carcinogenic and safe oral administration of the synthesized complexes.Communicated by Ramaswamy H. Sarma.
PubMed: 37599509
DOI: 10.1080/07391102.2023.2246565 -
International Journal of Molecular... Jul 2023Cells produce free radicals and antioxidants when exposed to toxic compounds during cellular metabolism. However, free radicals are deleterious to lipids, proteins, and...
Cells produce free radicals and antioxidants when exposed to toxic compounds during cellular metabolism. However, free radicals are deleterious to lipids, proteins, and nucleic acids. Antioxidants neutralize and eliminate free radicals from cells, preventing cell damage. Therefore, the study aims to determine whether the antioxidants butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) will ameliorate the maximum dose of acrylamide and alpha (α)-solanine synergistic toxic effects in exposed BEAS-2B cells. These toxic compounds are consumed worldwide by eating potato products. BEAS-2B cells were simultaneously treated with BHA 10 μM and BHT 20 μM and incubated in a 5% CO humidified incubator for 24 h, followed by individual or combined treatment with acrylamide (3.5 mM) and α-solanine (44 mM) for 48 h, including the controls. Cell morphology, DNA, RNA, and protein were analyzed. The antioxidants did not prevent acrylamide and α-solanine synergistic effects in exposed BEAS-2B cells. However, cell morphology was altered; polymerase chain reaction (PCR) showed reduced RNA constituents but not DNA. In addition, the toxic compounds synergistically inhibited AKT/PKB expression and its downstream genes. The study showed BHA and BHT are not protective against the synergetic toxic effects of acrylamide and α-solanine in exposed BEAS-2B cells.
Topics: Antioxidants; Solanine; Butylated Hydroxytoluene; Butylated Hydroxyanisole; Acrylamide; Proteins; DNA; RNA
PubMed: 37569330
DOI: 10.3390/ijms241511956