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Molecules (Basel, Switzerland) Apr 2022In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon's method are reported. Generally, the previously reported yields of asymmetric...
In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon's method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as (53%), (38%), and (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and -BuNH in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41-76%) were obtained, except for (36.7%), (34%), and (39.5%). Furthermore, compounds , , , , , , , , and are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds (IC = 37.57 ± 0.89 μM) and (IC = 37.17 ± 1.76 μM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds (IC = 11.36 ± 0.65 μM) and (IC = 10.91 ± 0.77 μM) displayed potent 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC = 10.14 ± 1.04 μM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT.
Topics: Antioxidants; Butylated Hydroxytoluene; Curcumin; Diarylheptanoids; Free Radical Scavengers; Water
PubMed: 35458741
DOI: 10.3390/molecules27082547 -
Journal of Traditional Chinese Medicine... Jun 2018To assess the antioxidant capacity of aqueous extracts of buds and flowers of Lonicera japonica Thunb. (BLJ and FLJ) using in vitro assays.
OBJECTIVE
To assess the antioxidant capacity of aqueous extracts of buds and flowers of Lonicera japonica Thunb. (BLJ and FLJ) using in vitro assays.
METHODS
We assessed the in vitro antioxidant activities of aqueous extracts of BLJ and FLJ and compared with that of classical antioxidants vitamin C and butylated hydroxytoluene, using several well-established methods including the 1,1-diphenyl-2-picryl-hydrazyl assay, 2,2'-azino-bis (3-ethylbenzthiazoline-6-sulfonic acid) assay, reducing power assay, fluorescence recovery after photobleaching assay, ¦Â-carotene bleaching assay, ferric thiocyanate assay, and thiobarbituric acid method.
RESULTS
The aqueous extracts of both BLJ and FLJ had similarly potent antioxidant capacity. There were no significance differences between BLJ and FLJ in all the assays.
CONCLUSION
The aqueous extracts of both BLJ and FLJ have antioxidant activity with comparable efficacy. These findings suggest that both BLJ and FLJ may have the potential as natural antioxidants.
PubMed: 32185969
DOI: No ID Found -
Food Science of Animal Resources Oct 2019This study was performed to assess the comparison of the effects amongst butylated hydroxytoluene (BHT), clove extract (CE), and ascorbic acid (AA) as antioxidants on...
This study was performed to assess the comparison of the effects amongst butylated hydroxytoluene (BHT), clove extract (CE), and ascorbic acid (AA) as antioxidants on the oxidative stability and color values in fresh beef patties. The adding of BHT, AA, and CE to patties significantly restrained lipid oxidation, lowered hue angle as color value, and expanded redness and chroma values of fresh beef patties in comparison to the control (p<0.05). BHT and AA significantly led to impede the protein oxidation of patties by lowering carbonyl content (p<0.05). CE had no negative effect on protein oxidation. The antioxidant effects of BHT, AA, and CE were obviously manifested. Nonetheless, BHT, AA, and CE appeared to have insignificant difference of each other for lowering the protein oxidation at the end of storage. BHT and CE represented lowered lipid oxidation in comparison to AA. The antioxidant effects of BHT, AA, and CE on lipid oxidation were more marked than the effects on protein oxidation. Furthermore, CE as a natural antioxidant evinced the efficiency in oxidative stability and color stability in fresh beef patties. The study implied that CE could substitute the use of BHT and AA when making beef patties during storage.
PubMed: 31728446
DOI: 10.5851/kosfa.2019.e67 -
Bioresources and Bioprocessing Mar 2022The vitamin A component retinol has become an increasingly sought-after cosmetic ingredient. In previous efforts for microbial biosynthesis of vitamin A, a mixture of...
The vitamin A component retinol has become an increasingly sought-after cosmetic ingredient. In previous efforts for microbial biosynthesis of vitamin A, a mixture of retinoids was produced. In order to efficiently produce retinol at high purity, the precursor and NADPH supply was first enhanced to improve retinoids accumulation in the S. cerevisiae strain constructed from a β-carotene producer by introducing β-carotene 15,15'-dioxygenase, following by screening of heterologous and endogenous oxidoreductases for retinal reduction. Env9 was found as an endogenous retinal reductase and its activity was verified in vitro. By co-expressing Env9 with the E. coli ybbO, as much as 443.43 mg/L of retinol was produced at 98.76% purity in bi-phasic shake-flask culture when the antioxidant butylated hydroxytoluene was added to prevent retinoids degradation. The retinol titer reached 2479.34 mg/L in fed-batch fermentation. The success in selective biosynthesis of retinol would lay a solid foundation for its biotechnological production.
PubMed: 38647788
DOI: 10.1186/s40643-022-00512-8 -
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 -
Environmental Research Jan 2021The UV filter 4-methylbenzylidene camphor (4-MBC), used in cosmetics, the antioxidant butylated hydroxytoluene (BHT), used inter alia as a food additive and in...
Metabolites of 4-methylbenzylidene camphor (4-MBC), butylated hydroxytoluene (BHT), and tris(2-ethylhexyl) trimellitate (TOTM) in urine of children and adolescents in Germany - human biomonitoring results of the German Environmental Survey GerES V (2014-2017).
The UV filter 4-methylbenzylidene camphor (4-MBC), used in cosmetics, the antioxidant butylated hydroxytoluene (BHT), used inter alia as a food additive and in cosmetics, and the plasticizer tris(2-ethylhexyl) trimellitate (TOTM), used mainly in medical devices as substitute for di-(2-ethylhexyl) phthalate (DEHP), are suspected to have endocrine disrupting effects. Human biomonitoring methods that allow for assessing the internal exposure of the general population to these substances were recently developed in a German cooperation to enhance the use of human biomonitoring. First-morning void urine samples from 3- to 17-year-old children and adolescents living in Germany were analysed for metabolites of 4-MBC (N = 447), BHT (N = 2091), and TOTM (N = 431) in the population-representative German Environmental Survey on Children and Adolescents 2014-2017 (GerES V). 4-MBC metabolites were found in quantifiable amounts only in single cases and exposure levels remained well below health-based guidance values. In contrast, ubiquitous exposure to BHT became evident with a geometric mean (GM) urinary concentration of the metabolite BHT acid of 2.346 μg/L (1.989 μg/g) and a maximum concentration of 248 μg/L (269 μg/g). The highest GM concentration was found in young children aged 3-5 years, yet no specific sources of exposure could be identified. Also, TOTM metabolites were found in quantifiable amounts only in very few samples. None of these findings could be related to previous hospital treatment or exposure via house dust. The presented results will be the basis to derive reference values for exposure of children and adolescents in Germany to BHT and will facilitate to identify changing exposure levels in the general population.
Topics: Adolescent; Benzoates; Biological Monitoring; Butylated Hydroxytoluene; Camphor; Child; Child, Preschool; Environmental Exposure; Environmental Monitoring; Environmental Pollutants; Germany; Humans; Phthalic Acids
PubMed: 33096061
DOI: 10.1016/j.envres.2020.110345 -
Food Research International (Ottawa,... Jun 2022Brazilian biodiversity includes species of the genus Solanum that have several biological activities, in addition to their relevance to agriculture, economics and...
Antioxidant and anti-inflammatory effects of fractions from ripe fruits of Solanum lycocarpum St. Hil. (Solanaceae) and putative identification of bioactive compounds by GC-MS and LC-DAD-MS.
Brazilian biodiversity includes species of the genus Solanum that have several biological activities, in addition to their relevance to agriculture, economics and popular medicine. The ripe fruits of Solanum lycocapum are an important nutritional food source, since they have levels of vitamin C, total soluble sugars, sucrose, phosphorus, and iron comparable or exceed the levels present in fruits such as pineapples, bananas, oranges, and mangoes. The pulp of the fruit is consumed by the population, and it is also used to produce jellies; to make marmalade, replacing the quince, and it can also be mixed with peaches in the preparation of peach. The objective of this study was to evaluate the anti-inflammatory and antioxidant activities of fractions obtained from the ripe fruits and to identify the constituents with these biological properties. The ripe fruits were collected, dried, crushed, and subjected to extraction by exhaustive percolation, obtaining an ethanol extract that was partitioned with solvents of increasing polarities, obtaining hexane (HEX), ethyl acetate (AC), and hydroethanol (HE) fractions. The AC fraction showed higher antioxidant potential compared to BHT (2,6-di-tert-butyl-4-methylphenol) and similar activity to AA (ascorbic acid) by DPPH (1,1-diphenyl-2-picrylhydrazyl) radical assay, while HEX and HE fractions exhibited of IC values similar to BHT. The AC fraction also presented similar activity to BHT by FRAP (Ferric Reducing Antioxidant Power) test. Intraperitoneal treatment with HEX (100 and 300 mg/kg) and HE (100 mg/kg) fractions caused significant inhibition of paw edema induced by carrageenan, 4 and 6 h after the inflammatory stimuli. When analyzed by GC-MS, fatty acids, phytosterols, and triterpenoid were identified in the HEX fraction, whilst 31 compounds were annotated in the AC and HE fractions analyzed by LC-DAD-MS, being phenylpropanoid derivatives, chlorogenic acids, and steroidal glycoalkaloids. The ripe fruits of S. lycocarpum have antioxidant and anti-inflammatory activities, and the detected chemical compounds, especially caffeoylquinic acid derivatives, spermidine, stigmasterol, and β-sitosterol, may be correlated with these activities. The ripe fruits of this species can be a food alternative rich in bioactive compounds and with benefits for human health.
Topics: Anti-Inflammatory Agents; Antioxidants; Ascorbic Acid; Butylated Hydroxytoluene; Fruit; Gas Chromatography-Mass Spectrometry; Humans; Phenols; Plant Extracts; Solanum; Vegetables
PubMed: 35651017
DOI: 10.1016/j.foodres.2022.111145 -
Molecules (Basel, Switzerland) May 2022Coumestrol (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...
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 (Cu)-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 IC value of 25.95 μg/mL (r: 0.9005) while BHA, BHT, Trolox, and α-Tocopherol demonstrated IC 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 K values of 10.25 ± 1.94, 5.99 ± 1.79, 25.41 ± 1.10, and 30.56 ± 3.36 nM towards these enzymes, respectively.
Topics: Acetylcholinesterase; Antioxidants; Butylated Hydroxyanisole; Butylated Hydroxytoluene; Butyrylcholinesterase; Carbonic Anhydrases; Coumestrol; Free Radical Scavengers; Glycoside Hydrolases; alpha-Tocopherol
PubMed: 35630566
DOI: 10.3390/molecules27103091 -
Pharmacognosy Reviews 2016Plants remain a vital source of drugs and at present, much emphasis is given to nutraceuticals. Herbal medicines have been the basis of treatment and cure for various...
Plants remain a vital source of drugs and at present, much emphasis is given to nutraceuticals. Herbal medicines have been the basis of treatment and cure for various diseases and physiological conditions in the traditional methods practiced such as ayurveda and homeopathy. Litchi chinensis belongs to the Sapindaceae family and is well-known in the Indian traditional system for its traditional uses. The parts of the plant used are leaves, flowers, fruits, seed, pulp, and pericarp. All parts of the plant are rich sources of phytochemicals--epicatechin; procyanidin A2 and procyanidin B2; leucocyanidin; cyanidin glycoside, malvidin glycoside, and saponins; butylated hydroxytoluene; isolariciresinol; kaempferol; rutin; and stigmasterol. In the present review, we explore the lychee's description, traditional medicinal uses, and phytoconstituents, and investigate the pharmacological activities in various parts of the lychee to show its importance in ethanopharmacology. This is so that this review can serve as a ready-to-use material for further research on the plant.
PubMed: 27041875
DOI: 10.4103/0973-7847.176548 -
The Journal of Veterinary Medical... Jul 2011This study evaluated the effect of butylated hydroxytoluene (BHT), a lipid-soluble antioxidant, on dog sperm in chilling storage and cryopreservation. In Experiment 1,...
This study evaluated the effect of butylated hydroxytoluene (BHT), a lipid-soluble antioxidant, on dog sperm in chilling storage and cryopreservation. In Experiment 1, 0.2, 0.4, 0.8 and 1.6 mM BHT were added to egg yolk Tris extender (EYT), and sperm were stored at 4°C for 96 hr. Sperm motility, viability, acrosomal integrity and morphological abnormality in the BHT treatment groups were not different from those of the control (0 mM BHT). In Experiment 2, the effect of BHT in EYT containing 0.75% Equex STM paste and 5% glycerol on survivability of cryopreserved sperm was examined after culture at 39°C for 3 hr. Sperm motility, viability and acrosomal integrity in the 0.2 to 0.8 mM BHT treatment groups were not different from those of the control. However, sperm motility, viability and acrosomal integrity decreased when 1.6 mM BHT was added to the extender (P<0.05). In conclusion, supplementation of the extender with 0.2 to 0.8 mM BHT did not affect characteristics of dog sperm in chilling storage and cryopreservation. Supplementation of 1.6 mM BHT did not affect characteristics of chilled sperm but impaired longevity of cryopreserved sperm in the dog.
Topics: Acrosome; Animals; Antioxidants; Butylated Hydroxytoluene; Cell Survival; Cryopreservation; Dogs; Male; Semen Preservation; Sperm Motility; Spermatozoa
PubMed: 21427519
DOI: 10.1292/jvms.10-0460