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1.
Clin Exp Pharmacol Physiol ; 50(3): 205-217, 2023 03.
Artículo en Inglés | MEDLINE | ID: mdl-36479862

RESUMEN

Many research studies have proposed that about two-thirds of the medicinal plant species of the world possess significant antioxidant potential. Antioxidants are very beneficial as they decrease oxidative stress (OS) in cells and hence play their role in management as well as treatment of numerous diseases like cancers, cardiovascular diseases, as well as many inflammatory illnesses. This review comprises the antioxidant potential of numerous parts of medicinal plants like leaves, stems, roots, seeds, fruits, as well as bark. Synthetic antioxidants named butylated hydroxyanisole (BHA) as well as butylated hydroxytoluene (BHT) are extensively employed in foods because of their role as food preservatives. Several natural antioxidants have better efficacy as compared to synthetic antioxidants. These medicinal plants include Geranium sanguineum L., Rheum ribes L., Diospyros abyssinica, Sargentodoxa cuneata Rehd. Et Wils, Pistacia lentiscus, Ficus microcarpa L. fil., Polyalthia cerasoides (Roxb.) Bedd, Cunn, Teucrium polium L., Crataeva nurvala Buch-Ham., Urtica dioica L., Dracocephalum moldavica L., Momordica Charantia L., Acacia auriculiformis A., Bidens pilosa Linn. The Lamiaceae species, Radiata, Leea indica, Pelargonium endlicherianum, Salvia officinalis L., and Uncaria tomentosa (Willd.) DC. The literature study disclosed more side effects of synthetic antioxidants (including food additives) in comparison with natural antioxidants and for prevention of many diseases.


Asunto(s)
Antioxidantes , Plantas Medicinales , Antioxidantes/farmacología , Hidroxitolueno Butilado/efectos adversos , Hidroxianisol Butilado/efectos adversos
2.
Int J Toxicol ; 42(3_suppl): 17S-19S, 2023 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-37751543

RESUMEN

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.


Asunto(s)
Hidroxitolueno Butilado , Cosméticos , Hidroxitolueno Butilado/toxicidad , Hidroxianisol Butilado , Antioxidantes , Cosméticos/toxicidad
3.
Int J Mol Sci ; 24(15)2023 Jul 26.
Artículo en Inglés | MEDLINE | ID: mdl-37569330

RESUMEN

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% CO2 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.


Asunto(s)
Antioxidantes , Solanina , Antioxidantes/farmacología , Hidroxitolueno Butilado , Hidroxianisol Butilado/farmacología , Acrilamida/toxicidad , Proteínas , ADN , ARN
4.
Molecules ; 28(16)2023 Aug 15.
Artículo en Inglés | MEDLINE | ID: mdl-37630328

RESUMEN

Maytenus dhofarensis 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 M. dhofarensis afforded dihydro-ß-agarofuran-type sesquiterpene pyridine alkaloid (1), lupanyl myristoate (2) and lignanolactone (3). Compounds (1-3) are new isolates from M. dhofarensis. The structures of these compounds were assigned through comprehensive IR, NMR, and ESI-MS analyses, and the relative configurations of compounds 1 and 3 were deduced from density function theory (DFT) calculations and NMR experiments. Compound 1 was assayed against the kinase enzyme and showed no inhibition activity for p38 alpha and delta at a 10 µM test concentration. Compound 3 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.


Asunto(s)
Maytenus , Animales , Bioensayo , Hidroxianisol Butilado , Cloroformo , Frutas , Cabras
5.
J Sci Food Agric ; 103(13): 6150-6166, 2023 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-37127924

RESUMEN

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.


Asunto(s)
Antioxidantes , Hidroxianisol Butilado , Humanos , Hidroxianisol Butilado/toxicidad , Antioxidantes/metabolismo , Oxidación-Reducción , Aditivos Alimentarios/toxicidad , Especies Reactivas de Oxígeno
6.
J Environ Sci Health B ; 58(4): 334-344, 2023.
Artículo en Inglés | MEDLINE | ID: mdl-36974485

RESUMEN

A polypyrrole (PPy)-cotton pad sorbent enclosed in tea bag envelope was developed and used in micro-solid phase extraction (µ-SPE) for the determination of butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). After extraction, the extract was qualified and quantified by a gas chromatograph equipped with a flame ionization detector (GC-FID). Parameters influencing this developed method and the efficiency of µ-SPE were studied and optimized. Under the optimal conditions, the developed method provided good linearity in a concentration range of 0.100-100 µg L-1 for BHA and 0.050-50 µg L-1 for BHT, respectively. The limits of detection were 39.27 ± 0.52 ng L-1 for BHA and 16.96 ± 0.17 ng L-1 for BHT. Satisfactory relative recoveries of BHA and BHT were achieved in the range from 86.8 ± 1.9 to 117.1 ± 2.3% with acceptable relative standard deviation (RSD) below 8.1%. Good reproducibility was obtained with RSDs < 3.1%, for n = 6. The developed adsorbent is easy to operate, low cost, eco-friendly, reusable, with high extraction efficiency, and was successfully applied in the simultaneous synthetic antioxidant determination of non-alcoholic beverage samples.


Asunto(s)
Antioxidantes , Polímeros , Antioxidantes/análisis , Hidroxitolueno Butilado/análisis , Pirroles , Hidroxianisol Butilado/análisis , Reproducibilidad de los Resultados , Bebidas ,
7.
Chem Res Toxicol ; 35(5): 840-848, 2022 05 16.
Artículo en Inglés | MEDLINE | ID: mdl-35416036

RESUMEN

Biotransformation, especially by human CYP450 enzymes, plays a crucial role in regulating the toxicity of organic compounds in organisms, but is poorly understood for most emerging pollutants, as their numerous "unusual" biotransformation reactions cannot retrieve examples from the textbooks. Therefore, in order to predict the unknown metabolites with altering toxicological profiles, there is a realistic need to develop efficient methods to reveal the "unusual" metabolic mechanism of emerging pollutants. Combining experimental work with computational predictions has been widely accepted as an effective approach in studying complex metabolic reactions; however, the full quantum chemical computations may not be easily accessible for most environmentalists. Alternatively, this work practiced using the concepts from physical organic chemistry for studying the interrelationships between structure and reactivity of organic molecules, to reveal the "unusual" metabolic mechanism of synthetic phenolic antioxidants catalyzed by CYP450, for which the simple pencil-and-paper and property-computation methods based on physical organic chemistry were performed. The phenol-coupling product of butylated hydroxyanisole (BHA) (based on spin aromatic delocalization) and ipso-addition quinol metabolite of butylated hydroxytoluene (BHT) (based on hyperconjugative effect) were predicted as two "unusual" metabolites, which were further confirmed by our in vitro analysis. We hope this easily handled approach will promote environmentalists to attach importance to physical organic chemistry, with an eye to being able to use the knowledge gained to efficiently predict the fates of substantial unknown synthesized organic compounds in the future.


Asunto(s)
Antioxidantes , Contaminantes Ambientales , Hidroxianisol Butilado/análisis , Hidroxianisol Butilado/química , Hidroxianisol Butilado/metabolismo , Hidroxitolueno Butilado/análisis , Hidroxitolueno Butilado/química , Hidroxitolueno Butilado/metabolismo , Química Orgánica , Sistema Enzimático del Citocromo P-450 , Contaminantes Ambientales/análisis , Humanos , Fenoles/análisis
8.
Bioorg Med Chem Lett ; 72: 128847, 2022 09 15.
Artículo en Inglés | MEDLINE | ID: mdl-35700955

RESUMEN

Zirconium-89 (89Zr) has been explored for molecularly targeted positron emission tomography (PET) imaging of various diseases. We synthesized and evaluated a novel chelator (DA-18C6-BHA) for 89Zr. The new chelator is structured on a macrocyclic backbone (1,10-diaza-18-crown-6) and contains hydroxamates as acyclic donor groups. The new chelator ((DA-18C6-BHA) was rapidly labeled with 89Zr under mild conditions. The 89Zr-labeled DA-18C6-BHA complex remained stable in human serum and apotransferrin for 7 days. When challenged with excess EDTA solution, 89Zr-labeled DA-18C6-BHA was shown to hold 89Zr without losing considerable radioactivity to EDTA. The 89Zr-labeled DA-18C6-BHA complex displayed high complex stability in normal mice as evidenced by low bone uptake.


Asunto(s)
Quelantes , Éteres Corona , Animales , Hidroxianisol Butilado , Ácido Edético , Humanos , Ácidos Hidroxámicos , Ratones , Tomografía de Emisión de Positrones/métodos , Radioisótopos , Circonio
9.
Environ Sci Technol ; 56(5): 3204-3213, 2022 03 01.
Artículo en Inglés | MEDLINE | ID: mdl-35133139

RESUMEN

3-tert-Butyl-4-hydroxyanisole (3-BHA), one of the widely used food antioxidants, has been found to act as a potential obesogen by promoting adipogenesis in vitro and inducing white adipose tissue development in vivo. Whether 3-BHA-induced visceral obesity was accompanied by a disruption of hepatic lipid homeostasis in mammals remained unclear. In this study, we evaluated the effect of 3-BHA on the development of nonalcoholic fatty liver disease (NAFLD) in male C57BL/6J mice. After 18 weeks of oral administration of 10 mg/kg 3-BHA, the mice fed with a high-fat diet (HFD) had higher hepatic triglyceride concentrations (0.32 mg/mg protein) and severer steatosis (1.57 for the NAFLD score) than the control ones. The in vivo hepatic lipid deposition disturbed by 3-BHA was transcriptionally regulated by the genes involved in lipid uptake, de novo lipogenesis, fatty acid oxidation, and lipid export. The in vitro studies further confirmed that 24 h of exposure to 50 µM 3-BHA could induce intracellular oleic acid (OA) uptake and triglyceride accumulation (1.5-fold of the OA control) in HepG2 cells. Lipidomic analysis indicated the perturbation of 3-BHA in the levels of 30 lipid species related to sphingolipids, glycerophospholipids, and glycerolipids under HFD conditions. The findings herein first revealed the disruption effect of 3-BHA on hepatic lipid homeostasis, thus exacerbating the development of HFD-induced NAFLD.


Asunto(s)
Dieta Alta en Grasa , Enfermedad del Hígado Graso no Alcohólico , Animales , Hidroxianisol Butilado , Metabolismo de los Lípidos , Hígado/metabolismo , Masculino , Mamíferos , Ratones , Ratones Endogámicos C57BL , Enfermedad del Hígado Graso no Alcohólico/inducido químicamente , Triglicéridos/metabolismo , Triglicéridos/farmacología
10.
Phys Chem Chem Phys ; 24(43): 26413-26420, 2022 Nov 09.
Artículo en Inglés | MEDLINE | ID: mdl-36300323

RESUMEN

Surface-enhanced Raman spectroscopy (SERS) relies heavily on a substrate for highly sensitive detection, which may have poor performance due to weak adsorption of molecules on the surface. The substrate-molecule interaction is a crucial factor in the SERS detection of weakly adsorbed molecules. Herein, we performed a dynamic SERS detection of butylated hydroxyanisole (BHA) on a silver nano-tripod (AgNT) substrate and reported the instability detection process of BHA. The interaction of BHA molecules with the AgNT substrate was analyzed by the detected phenomena combined with molecular electrostatic potential (MEP) and SERS surface selection rules, and a dynamic adsorption model of BHA molecules was developed. The model postulates that the conversion of solution state for molecular adsorption orientation is the key to dynamic SERS detection. The signal acquisition time of BHA was extended from 1 min to 3 min by adjusting the detection solvent, which improved the practicality and operability of SERS detection. Combining surface adsorption analysis with the SERS process may provide a reference for the detection and analysis of other weakly adsorbed molecules.


Asunto(s)
Hidroxianisol Butilado , Plata , Plata/química , Espectrometría Raman/métodos , Adsorción , Electricidad Estática
11.
Ecotoxicol Environ Saf ; 231: 113179, 2022 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-35026586

RESUMEN

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-1 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-1, 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 × 107 M-1 s-1and 4.76 × 107 M-1 s-1 for the H-abstraction and OH-addition reactions, respectively. Through the calculation of the subsequent reactions of the abs-H0-TS1 and add-C4-M1 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.


Asunto(s)
Hidroxianisol Butilado , Hidroquinonas , Antioxidantes , Hidroxianisol Butilado/toxicidad , Fenoles
12.
Drug Chem Toxicol ; 45(4): 1899-1906, 2022 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-34013795

RESUMEN

Butylated hydroxyanisole (BHA) and the chemically similar butylated hydroxytoluene (BHT) are widely used as antioxidants. Toxicity of BHA and BHT has been reported under in vitro and in vivo experimental conditions. However, the mechanism of BHA-induced toxic effects in cells is unclear. In this study, the cytotoxic effects of BHA and differences in cell death mechanism for BHA and BHT were investigated in rat thymocytes by flow cytometric analysis using a fluorescent probe. We observed a significant increase in propidium iodide fluorescence in the population of cells treated with 100 µM and 300 µM BHA (dead cells). Thymocytes treated with 100 µM BHA showed increased intracellular Ca2+ and Zn2+ levels and depolarized cell membranes. BHA (30-100 µM) decreased non-protein thiol content of cells, indicating decreased glutathione content. Co-stimulation with 100 µM BHA and 300 µM H2O2 acted synergistically to increase cell lethality. Moreover, BHA significantly increased caspase-3 activity and the number of annexin-V-positive cells in a concentration-dependent manner, indicating apoptosis. However, BHT reduced caspase-3 activity and increased the number of annexin-V-negative dead cells, indicating non-apoptotic cell death. Our results reveal the toxicity of BHA could be attributed to increased levels of intracellular Ca2+ and Zn2+, resulting in an increased vulnerability of rat thymocytes to oxidative stress. In addition, we demonstrate that whereas BHA induced apoptosis, BHT induced non-apoptotic cell death in rat thymocytes. Therefore, these results may support the safety of BHA, but also demonstrate the importance of performing toxicity evaluation at the cellular level besides the tissue level.


Asunto(s)
Hidroxianisol Butilado , Hidroxitolueno Butilado , Animales , Anexinas , Antioxidantes/farmacología , Apoptosis , Hidroxianisol Butilado/metabolismo , Hidroxianisol Butilado/toxicidad , Hidroxitolueno Butilado/metabolismo , Hidroxitolueno Butilado/toxicidad , Calcio/metabolismo , Caspasa 3/metabolismo , Peróxido de Hidrógeno/metabolismo , Ratas , Zinc/metabolismo
13.
Mikrochim Acta ; 189(12): 469, 2022 11 24.
Artículo en Inglés | MEDLINE | ID: mdl-36422711

RESUMEN

New sensing platforms based on screen-printed carbon electrodes modified with composites based on polystyrene sulfonate and oxidized multi-walled carbon nanotubes (PSS/MWCNTs-COOH/SPCE) have been used to develop a novel HPLC method with electrochemical detection (ECD) for the determination of the most used synthetic phenolic antioxidants in cosmetics: butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), tert-butylhydroquinone (TBHQ) and propyl gallate (PG). Optimal separation conditions were achieved using methanol: 0.10 mol L-1 acetate solution at pH 6 as mobile phase with a gradient elution program from 60 to 90% of methanol percentage in 15 min. The electrochemical detection was carried out in amperometric mode using the PSS/MWCNTs-COOH/SPCE at + 0.80 V vs. Ag. Under these optimal separation and detection conditions, the limits of detection (LOD) were between 0.11 and 0.25 mg L-1. These LOD values were better, especially for BHT, than those previously published in other HPLC methods. Linear ranges from 0.37 mg L-1, 0.83 mg L-1, 0.69 mg L-1 and 0.56 mg L-1 to 10 mg L-1 were obtained for PG, TBHQ, BHA and BHT, respectively. RSD values equal or lower than 5% and 8% were achieved for repeatability and reproducibility, respectively. The HPLC-ECD method was successfully applied to analyze different cosmetic samples. Recovery values within 83-109% were obtained in the validation studies.


Asunto(s)
Cosméticos , Nanocompuestos , Nanotubos de Carbono , Hidroxianisol Butilado/análisis , Antioxidantes , Hidroxitolueno Butilado/análisis , Cromatografía Líquida de Alta Presión/métodos , Metanol , Reproducibilidad de los Resultados , Fenoles , Electrodos , Galato de Propilo/análisis
14.
Int J Mol Sci ; 23(6)2022 Mar 16.
Artículo en Inglés | MEDLINE | ID: mdl-35328637

RESUMEN

The Bhas 42 cell transformation assay (Bhas 42 CTA) is the first Organization for Economic Cooperation and Development (OECD)-certificated method used as a specific tool for the detection of the cell-transformation potential of tumor-promoting compounds, including non-genotoxic carcinogens (NGTxCs), as separate from genotoxic carcinogens. This assay offers the great advantage of enabling the phenotypic detection of oncotransformation. A key benefit of using the Bhas 42 CTA in the study of the cell-transformation mechanisms of tumor-promoting compounds, including non-genotoxic carcinogens, is that the cell-transformation potential of the chemical can be detected directly without treatment with a tumor-initiating compound since Bhas 42 cell line was established by transfecting the v-Ha-ras gene into a mouse fibroblast cloned cell line. Here, we analyzed the gene expression over time, using DNA microarrays, in Bhas 42 cells treated with the tumor-promoting compound 12-O-tetradecanoylphorbol-13-acetate (TPA), and NGTxC, with a total of three repeat experiments. This is the first paper to report on gene expression over time during the process of cell transformation with only a tumor-promoting compound. Pathways that were activated or inactivated during the process of cell transformation in the Bhas 42 cells treated with TPA were related not only directly to RAS but also to various pathways in the hallmarks of cancer.


Asunto(s)
Hidroxianisol Butilado , Carcinógenos , Animales , Células 3T3 BALB , Pruebas de Carcinogenicidad/métodos , Carcinógenos/toxicidad , Transformación Celular Neoplásica/genética , Expresión Génica , Ratones , Acetato de Tetradecanoilforbol/farmacología
15.
Molecules ; 27(20)2022 Oct 21.
Artículo en Inglés | MEDLINE | ID: mdl-36296730

RESUMEN

Antioxidants are food additives largely employed to inhibit oxidative reactions in foodstuffs rich in oils and fat lipids, extending the shelf life of foodstuffs and inhibiting alterations in color, flavor, smell, and loss of nutritional value. However, various research has demonstrated that the inadequate use of synthetic antioxidants results in environmental and health problems due to the fact that some of these compounds present toxicity, and their presence in the human body, in high concentrations, is related to the development of some cancer types and other diseases. Therefore, the development of analytical methods for identifying and quantifying synthetic antioxidants in foodstuffs is fundamental to quality control and in ensuring consumer food safety. This review describes the recent chromatographic and electrochemical techniques used in the detection of synthetic phenolic antioxidants in foodstuffs, highlighting the main characteristics, advantages and disadvantages of these methods, and specific typical features, which include extraction methods for sample preparation and materials used in the working electrode construction, considering chromatographic and voltammetric methods, since these specific features influence the efficiency in the analysis.


Asunto(s)
Antioxidantes , Hidroxianisol Butilado , Humanos , Antioxidantes/análisis , Aditivos Alimentarios/análisis , Fenoles/análisis , Aceites de Plantas , Hidroxitolueno Butilado
16.
Molecules ; 27(10)2022 May 11.
Artículo en Inglés | MEDLINE | ID: mdl-35630566

RESUMEN

Coumestrol (3,9-dihydroxy-6-benzofuran [3,2-c] chromenone) as a phytoestrogen and polyphenolic compound is a member of the Coumestans family and is quite common in plants. In this study, antiglaucoma, antidiabetic, anticholinergic, and antioxidant effects of Coumestrol were evaluated and compared with standards. To determine the antioxidant activity of coumestrol, several methods-namely N,N-dimethyl-p-phenylenediamine dihydrochloride radical (DMPD•+)-scavenging activity, 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulphonate) radical (ABTS•+)-scavenging activity, 1,1-diphenyl-2-picrylhydrazyl radical (DPPH•)-scavenging activity, potassium ferric cyanide reduction ability, and cupric ion (Cu2+)-reducing activity-were performed. Butylated hydroxyanisole (BHA), Trolox, α-Tocopherol, and butylated hydroxytoluene (BHT) were used as the reference antioxidants for comparison. Coumestrol scavenged the DPPH radical with an IC50 value of 25.95 µg/mL (r2: 0.9005) while BHA, BHT, Trolox, and α-Tocopherol demonstrated IC50 values of 10.10, 25.95, 7.059, and 11.31 µg/mL, respectively. When these results evaluated, Coumestrol had similar DPPH•-scavenging effect to BHT and lower better than Trolox, BHA and α-tocopherol. In addition, the inhibition effects of Coumestrol were tested against the metabolic enzymes acetylcholinesterase (AChE), butyrylcholinesterase (BChE), carbonic anhydrase II (CA II), and α-glycosidase, which are associated with some global diseases such as Alzheimer's disease (AD), glaucoma, and diabetes. Coumestrol exhibited Ki values of 10.25 ± 1.94, 5.99 ± 1.79, 25.41 ± 1.10, and 30.56 ± 3.36 nM towards these enzymes, respectively.


Asunto(s)
Antioxidantes , Anhidrasas Carbónicas , Acetilcolinesterasa , Antioxidantes/química , Antioxidantes/farmacología , Hidroxianisol Butilado/farmacología , Hidroxitolueno Butilado/farmacología , Butirilcolinesterasa , Cumestrol/farmacología , Depuradores de Radicales Libres/química , Depuradores de Radicales Libres/farmacología , Glicósido Hidrolasas , alfa-Tocoferol/farmacología
17.
Molecules ; 27(18)2022 Sep 11.
Artículo en Inglés | MEDLINE | ID: mdl-36144638

RESUMEN

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•+), N,N-dimethyl-p-phenylenediamine dihydrochloride (DMPD•+), and 1,1-diphenyl-2-picrylhydrazyl (DPPH•) scavenging abilities and K3[Fe(CN)6] and Cu2+ 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 IC50 value of 10.58 µg/mL. The IC50 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.


Asunto(s)
Antioxidantes , Aporfinas/farmacología , Glaucoma , Acetilcolinesterasa/metabolismo , Antioxidantes/química , Antioxidantes/farmacología , Compuestos de Bifenilo , Hidroxianisol Butilado/farmacología , Hidroxitolueno Butilado/farmacología , Butirilcolinesterasa/metabolismo , Anhidrasa Carbónica II , Antagonistas Colinérgicos , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/farmacología , Glicósido Hidrolasas , Humanos , Hipoglucemiantes/farmacología , Simulación del Acoplamiento Molecular , Picratos , Ácidos Sulfónicos/química , alfa-Tocoferol/farmacología
18.
Shokuhin Eiseigaku Zasshi ; 63(1): 12-19, 2022.
Artículo en Japonés | MEDLINE | ID: mdl-35264517

RESUMEN

In this study, we simultaneously determined three antioxidants, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), and tert-butylhydroquinone (TBHQ), using HPLC equipped both with a photodiode array detector and a fluorescence detector in 25 minutes per sample. Due to the combined use of the two detectors, we could achieve improved target selectivity. Further, quantification at the specific wavelengths for each target substance particularly increased BHT detection sensitivity. This approach enabled us to avoid repeated measurements during daily inspections. Furthermore, detections were performed using LC-MS/MS instead of GC-MS to overcome the problem of helium gas shortage.In addition, we investigated antioxidant stability in standard solutions during storage. Although TBHQ was stable in methanol with ascorbic acid at -20℃, ascorbic acid storage has possibility to lead to decrease in BHT and BHA concentrations. We recognized that the mixture of BHT and BHA dissolved in methanol at 4℃ and that of BHT, BHA and TBHQ dissolved in methanol with ascorbic acid at -20℃ were suitable for about one year.


Asunto(s)
Antioxidantes , Espectrometría de Masas en Tándem , Hidroxianisol Butilado/análisis , Cromatografía Líquida de Alta Presión , Cromatografía Liquida
19.
Regul Toxicol Pharmacol ; 121: 104887, 2021 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-33556417

RESUMEN

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.


Asunto(s)
Antioxidantes/clasificación , Hidroxianisol Butilado/clasificación , Carcinógenos/clasificación , Aditivos Alimentarios/clasificación , Animales , Antioxidantes/toxicidad , Hidroxianisol Butilado/toxicidad , Carcinógenos/toxicidad , Aditivos Alimentarios/toxicidad , Abastecimiento de Alimentos , Humanos , Medición de Riesgo
20.
Molecules ; 26(23)2021 Nov 24.
Artículo en Inglés | MEDLINE | ID: mdl-34885681

RESUMEN

In this study, the antioxidant and antiradical properties of some phyto lignans (nordihydroguaiaretic acid, secoisolariciresinol, secoisolariciresinol diglycoside, and α-(-)-conidendrin) and mammalian lignans (enterodiol and enterolactone) were examined by different antioxidant assays. For this purpose, radical scavenging activities of phyto and mammalian lignans were realized by 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) radical (ABTS•+) scavenging assay and 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) scavenging assay. Additionally, the reducing ability of phyto and mammalian lignans were evaluated by cupric ions (Cu2+) reducing (CUPRAC) ability, and ferric ions (Fe3+) and [Fe3+-(TPTZ)2]3+ complex reducing (FRAP) abilities. Also, half maximal inhibitory concentration (IC50) values were determined and reported for DPPH• and ABTS•+ scavenging influences of all of the lignan molecules. The absorbances of the lignans were found in the range of 0.150-2.320 for Fe3+ reducing, in the range of 0.040-2.090 for Cu2+ reducing, and in the range of 0.360-1.810 for the FRAP assay. On the other hand, the IC50 values of phyto and mammalian lignans were determined in the ranges of 6.601-932.167 µg/mL for DPPH• scavenging and 13.007-27.829 µg/mL for ABTS•+ scavenging. In all of the used bioanalytical methods, phyto lignans, as secondary metabolites in plants, demonstrated considerably higher antioxidant activity compared to that of mammalian lignans. In addition, it was observed that enterodiol and enterolactone exhibited relatively weaker antioxidant activities when compared to phyto lignans or standard antioxidants, including butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), Trolox, and α-tocopherol.


Asunto(s)
Antioxidantes/química , Depuradores de Radicales Libres/química , Lignanos/química , Peroxidación de Lípido/efectos de los fármacos , Fitoquímicos/química , Animales , Antioxidantes/farmacología , Benzotiazoles/química , Benzotiazoles/farmacología , Compuestos de Bifenilo/síntesis química , Compuestos de Bifenilo/farmacología , Hidroxianisol Butilado/química , Hidroxitolueno Butilado/química , Butileno Glicoles/química , Cromanos/química , Cobre/química , Depuradores de Radicales Libres/farmacología , Iones/química , Hierro/química , Lignanos/farmacología , Mamíferos , Masoprocol/química , Fitoquímicos/farmacología , Picratos/síntesis química , Picratos/farmacología , Ácidos Sulfónicos/química , Ácidos Sulfónicos/farmacología , Tetrahidronaftalenos/química
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