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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 -
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 -
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 -
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 -
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 -
Saudi Pharmaceutical Journal : SPJ :... Oct 2023Onion contains many dietary and bioactive components including phenolics and flavonoids. Spiraeoside (quercetin-4-O-β-D-glucoside) is one of the most putative...
Onion contains many dietary and bioactive components including phenolics and flavonoids. Spiraeoside (quercetin-4-O-β-D-glucoside) is one of the most putative flavonoids in onion. Several antioxidant techniques were used in this investigation to assess the antioxidant capabilities of spiraeoside, including 1,1-diphenyl-2-picrylhydrazyl radical (DPPH·) scavenging, N,N-dimethyl-p-phenylenediamine radical (DMPD) scavenging, 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulphonate) radical (ABTS) scavenging activities, cupric ions (Cu) reducing and potassium ferric cyanide reduction abilities. In contrast, the water-soluble α-tocopherol analogue trolox and the conventional antioxidants butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), and α-tocopherol were utilized as the standards for evaluation. Spiraeoside scavenged the DPPH radicals an IC of 28.51 μg/mL (r: 0.9705) meanwhile BHA, BHT, trolox, and α-tocopherol displayed IC of 10.10 μg/mL (r: 0.9015), 25.95 μg/mL (r: 0.9221), 7.059 μg/mL (r: 0.9614) and 11.31 μg/mL (r: 0.9642), accordingly. The results exhibited that spiraeoside had effects similar to BHT, but less potent than α-tocopherol, trolox and BHA. Also, inhibitory effects of spiraeoside were evaluated toward some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), carbonic anhydrase II (CA II) and α-glycosidase, which are related to a number of illnesses, such as Alzheimer's disease (AD), diabetes mellitus and glaucoma disorder. Spiraeoside exhibited IC values of 4.44 nM (r: 0.9610), 7.88 nM (r: 0.9784), 19.42 nM (r: 0.9673) and 29.17 mM (r: 0.9209), respectively against these enzymes. Enzyme inhibition abilities were compared to clinical used inhibitors including acetazolamide (for CA II), tacrine (for AChE and BChE) and acarbose (for α-glycosidase). Spiraeoside demonstrated effective antioxidant, anticholinergic, antidiabetic and antiglaucoma activities. With these properties, it has shown that Spiraeoside has the potential to be a medicine for some metabolic diseases.
PubMed: 37693735
DOI: 10.1016/j.jsps.2023.101760 -
Pharmaceutics May 2024The presence of mutagenic and carcinogenic N-nitrosamine impurities in medicinal products poses a safety risk. While incorporating antioxidants in formulations is a...
The presence of mutagenic and carcinogenic N-nitrosamine impurities in medicinal products poses a safety risk. While incorporating antioxidants in formulations is a potential mitigation strategy, concerns arise regarding their interference with drug absorption by inhibiting intestinal drug transporters. Our study screened thirty antioxidants for inhibitory effects on key intestinal transporters-OATP2B1, P-gp, and BCRP in HEK-293 cells (OATP2B1) or membrane vesicles (P-gp, BCRP) using H-estrone sulfate, H-N-methyl quinidine, and H-CCK8 as substrates, respectively. The screen identified that butylated hydroxyanisole (BHA) and carnosic acid inhibited all three transporters (OATP2B1, P-gp, and BCRP), while ascorbyl palmitate (AP) inhibited OATP2B1 by more than 50%. BHA had IC values of 71 ± 20 µM, 206 ± 14 µM, and 182 ± 49 µM for OATP2B1, BCRP, and P-gp, respectively. AP exhibited IC values of 23 ± 10 µM for OATP2B1. The potency of AP and BHA was tested with valsartan, an OATP2B1 substrate, and revealed IC values of 26 ± 17 µM and 19 ± 11 µM, respectively, in HEK-293-OATP2B1 cells. Comparing IC values of AP and BHA with estimated intestinal concentrations suggests an unlikely inhibition of intestinal transporters at clinical concentrations of drugs formulated with antioxidants.
PubMed: 38794309
DOI: 10.3390/pharmaceutics16050647 -
Biosensors Aug 2023Sesamol (SM) is a potent natural antioxidant that can quench free radicals and modulate the cholinergic system in the brain, thereby ameliorating memory and cognitive...
Sesamol (SM) is a potent natural antioxidant that can quench free radicals and modulate the cholinergic system in the brain, thereby ameliorating memory and cognitive impairment in Alzheimer's disease patients. Moreover, the total antioxidant capacity can be amplified by synergistic interactions between different antioxidants. Here, we constructed a ternary heterojunction graphitic carbon nitride/cupric sulfide/titanium dioxide (g-CN/CuS/TiO) photoelectrochemical (PEC) sensor for the quantification of SM and its synergistic interactions with other antioxidants. Crucially, the Schottky barrier in ternary semiconductors considerably enhances electron transfer. The PEC sensor showed a wide linear range for SM detection, ranging from 2 to 1277 μmol L, and had a limit of detection of 1.8 μmol L. Remarkably, this sensing platform could evaluate the synergism between SM and five typical lipid-soluble antioxidants: -butyl hydroquinone, vitamin E, butyl hydroxyanisole, propyl gallate, and butylated hydroxytoluene. Owing to its low redox potential, SM could reduce antioxidant radicals and promote their regeneration, which increased the overall antioxidant performance. The g-CN/CuS/TiO PEC sensor exhibited high sensitivity, satisfactory selectivity, and stability, and was successfully applied for SM determination in both soybean and peanut oils. The findings of this study provide guidance for the development of nutritional foods, nutrition analysis, and the treatment of diseases caused by free radicals.
Topics: Antioxidants
PubMed: 37754093
DOI: 10.3390/bios13090859 -
Life (Basel, Switzerland) Oct 2023Baicalin is the foremost prevalent flavonoid found in . It also frequently occurs in many multi-herbal preparations utilized in Eastern countries. The current research...
Baicalin is the foremost prevalent flavonoid found in . It also frequently occurs in many multi-herbal preparations utilized in Eastern countries. The current research has assessed and compared the antioxidant, antidiabetic, anticholinergic, and antiglaucoma properties of baicalin hydrate. Baicalin hydrate was tested for its antioxidant capacity using a variety of techniques, including 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 ions (Cu) reducing activities. Also, for comparative purposes, reference antioxidants, such as butylated hydroxyanisole (BHA), Trolox, α-Tocopherol, and butylated hydroxytoluene (BHT) were employed. Baicalin hydrate had an IC value of 13.40 μg/mL (r: 0.9940) for DPPH radical scavenging, whereas BHA, BHT, Trolox, and α-Tocopherol had IC values of 10.10, 25.95, 7.059, and 11.31 μg/mL for DPPH scavenging, respectively. These findings showed that baicalin hydrate had comparably close and similar DPPH scavenging capability to BHA, α-tocopherol, and Trolox, but it performed better than BHT. Additionally, apart from these studies, baicalin hydrate was tested for its ability to inhibit a number of metabolic enzymes, including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), carbonic anhydrase II (CA II), and α-glycosidase, which have been linked to several serious illnesses, such as Alzheimer's disease (AD), glaucoma, and diabetes, where the K values of baicalin hydrate toward the aforementioned enzymes were 10.01 ± 2.86, 3.50 ± 0.68, 19.25 ± 1.79, and 26.98 ± 9.91 nM, respectively.
PubMed: 38004276
DOI: 10.3390/life13112136 -
Molecules (Basel, Switzerland) Aug 2023Purslane ( L.) is rich in phenolic compounds, protein, and iron. This study aims to produce functional yogurt with enhanced antioxidant, anticancer, antiviral, and...
Purslane ( L.) is rich in phenolic compounds, protein, and iron. This study aims to produce functional yogurt with enhanced antioxidant, anticancer, antiviral, and antimicrobial properties by including safe purslane extract in yogurt formulation; the yogurt was preserved for 30 days at 4 °C, and then biochemical fluctuations were monitored. The purslane extract (PuE) had high phenolic compounds and flavonoids of 250 and 56 mg/mL, respectively. Therefore, PuE had considerable antioxidant activity, which scavenged 93% of DPPH˙, inhibited the viability of MCF-7, HCT, and HeLa cell lines by 84, 82, and 80%, respectively, and inhibited 82% of the interaction between the binding between Spike and ACE2 compared to a SARS-CoV-2 inhibitor test kit. PuE (20-40 µg/mL) inhibited the growth of tested pathogenic bacteria and strains, these strains isolated from spoild yogurt and identified at gene level by PCR. Caffeic acid glucoside and catechin were the main phenolic compounds in the HPLC profile, while the main flavor compound was carvone and limonene, representing 71% of total volatile compounds (VOCs). PuE was added to rats' diets at three levels (50, 150, and 250 µg/g) compared to butylated hydroxyanisole (BHA). The body weight of the rats fed the PuE diet (250 µg/g) increased 13% more than the control. Dietary PuE in rats' diets lowered the levels of low-density lipoprotein (LDL) levels by 72% and increased the levels of high-density lipoprotein (HDL) by 36%. Additionally, liver parameters in rats fed PuE (150 µg/g) decreased aspartate aminotransferase (AST), alanine aminotransferase (ALT), and malondialdehyde (MDA) levels by 50, 43, and 25%, respectively, while TP, TA, and GSH were increased by 20, 50, and 40%, respectively, compared to BHA. Additionally, PuE acts as a kidney protector by lowering creatinine and urea. PuE was added to yogurt at three concentrations (50, 150, and 250 µg/g) and preserved for 30 days compared to the control. The yogurt's pH reduced during storage while acidity, TSS, and fat content increased. Adding PuE increased the yogurt's water-holding capacity, so syneresis decreased and viscosity increased, which was attributed to enhancing the texture properties (firmness, consistency, and adhesiveness). MDA decreased in PuE yogurt because of the antioxidant properties gained by PuE. Additionally, color parameters and were enhanced by PuE additions and sensorial traits, i.e., color, flavor, sugary taste, and texture were enhanced by purslane extract compared to the control yogurt. Concerning the microbial content in the yogurt, the lactic acid bacteria (LAB) count was maintained as a control. Adding PuE at concentrations of 50, 150, and 250 µg/g to the yogurt formulation can enhance the quality of yogurt.
Topics: Humans; Rats; Animals; Antioxidants; Portulaca; Yogurt; Antiviral Agents; HeLa Cells; COVID-19; SARS-CoV-2; Plant Extracts; Phenols; Anti-Bacterial Agents
PubMed: 37570829
DOI: 10.3390/molecules28155859