Butylated Hydroxyanisole Research Articles

Essential Oil of Origanum vulgare var. aureum L. from Western Romania: Chemical Analysis, In Vitro and In Silico Screening of Its Antioxidant Activity

This investigation aims to assess the chemical composition and antioxidant properties of Origanum vulgare var. aureum L. essential oil (OEO). The oil was obtained with a 0.34% (v/w dried weight) yield and investigated by gas chromatography-mass spectrometry (GC–MS) analysis. The main compounds of the OEO were found to be gamma-terpinene (22.96%), para-cymene (14.72%), germacrene (11.64%), beta-trans-ocimene (9.81%), and cis-beta-ocimene (7.65%). Furthermore, individual antioxidant assays 1,1-diphenyl-2-picrylhydrazyl (DPPH) and [2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium] (ABTS) radical scavenging activities and beta-carotene/linoleic acid bleaching were carried out. OEO demonstrated better scavenging effects on the DPPH (IC50 93.12 ± 0.03 μg/mL) and ABTS (IC50 27.63 ± 0.01 μg/mL) assays (significantly lower IC50 values; p ≤ 0.001) than ascorbic acid (IC50 127.39 ± 0.45 μg/mL). In the beta-carotene/linoleic acid bleaching assay, the OEO exhibited a higher Relative antioxidant activity (RAA %) (82.36 ± 0.14%) but lower compared with butylated hydroxyanisole (BHA) (100%), with no significant differences (p > 0.05) observed. According to molecular docking results, the first two main compounds of the OEO, para-cymene, and gamma-terpinene, may potentially contribute to the biological antioxidant activity of the oil by inhibiting ROS (reactive oxygen species)-producing enzymes such as lipoxygenase and xanthin oxidase. These experimental data suggest that OEO could represent a valuable new natural antioxidant source with functional properties in the food or pharmaceutical industries.

Toll-like receptors and nuclear factor kappa B signaling pathway involvement in hepatorenal oxidative damage induced by some food preservatives in rats

Chemical food preservatives are extensively found in various processed food products in the human environment. Hence, this study aimed to investigate the effect of long-term exposure to five food preservatives (potassium sorbate (PS), butylated hydroxyanisole (BHA), sodium benzoate (SB), calcium propionate (CP), and boric acid (BA)) on the liver and kidney in rats and the probable underlying mechanisms. For 90 days, sixty male albino rats were orally given either water (control), 0.09 mg/kg b.wt BHA, 4.5 mg/kg b.wt PS, 0.9 mg/kg b.wt SB, 0.16 mg/kg b.wt BA, or 0.18 mg/kg b.wt CP. Liver and kidney function tests were assessed. Hepatic and renal oxidative stress biomarkers were estimated. Histologic examination analysis of liver and kidney tissues was achieved. Toll-like receptors 2 and 4 (TLR-2 and TLR-4), tumor necrosis factor-alpha (TNF-α), and nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) mRNA expression levels were measured. The results revealed that long-term oral dosing of the five food preservatives resulted in significant increases in alkaline phosphatase, alanine transaminase, aspartate transaminase, urea, uric acid, and creatinine levels. There were significant reductions in hepatic and renal antioxidant enzymes, an increase in MDA concentrations, and pathological alterations in renal and hepatic tissues. The mRNA levels of TLR-4, TLR-2, NF-κB, and TNF-α were elevated in the food preservatives-exposed groups. Conclusively, the current findings revealed that long-term exposure to PS, BHA, SB, CP, and BA has a negative impact on liver and kidney function. Furthermore, these negative effects could be mediated via oxidative stress induction, inflammatory reactions, and cytokine production.

Effective Improvement of the Oxidative Stability of Acer truncatum Bunge Seed Oil, a New Woody Oil Food Resource, by Rosemary Extract.

Acer truncatum Bunge is a versatile, oil-producing, woody tree natively and widely distributed in northern China. In 2011, The People's Republic of China's Ministry of Health certified Acer truncatum seed oil (Aoil) as a new food resource. Unsaturated fatty acids account for up to 92% of the entire Aoil. When Aoil is processed or stored, it can easily oxidize. In this study, the effects of rosemary (Rosmarinus officinalis L.) extract on the oxidation stability of Aoil were analysed from multiple angles. The results of radical scavenging ability, malondialdehyde, and free fatty acid reveal that rosemary crude extract (RCE), rosmarinic acid (RA), and carnosic acid (CA) can significantly inhibit the oxidation of Aoil, and CA has the best oxidative stability for Aoil among the tested components of the crude rosemary. The delayed oxidation ability of CA for Aoil was slightly weaker than that of tert-butylhydroquinone (TBHQ), but stronger than that of butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), and α-tocopherol (α-T), which was confirmed by microstructures, kinematic viscosity, Aoil weight change, and functional group. Additionally, CA-enriched Aoil had the smallest content of volatile lipid oxidation products. Moreover, lecithin-CA particles were added to enhance the oxidative stability of Aoil. These findings show that CA is a potent antioxidant, capable of successfully preventing Aoil oxidation.

Natural Antioxidants from Herbs and Spices and their effects for Improving the Functionality and Shelf Life of food and Dairy products: A Review

In the food sector, oxidative reactions seriously threaten the shelf life of both fresh and processed foods. Several diseases are thought to be caused by the generation of free radicals, which then cause biomolecules to oxidise. Due to efforts to make foods healthier by adding more polyunsaturated fatty acids and more sustainable by creating lightweight oxygen-permeable and light penetrating packaging, many foods are becoming more prone to oxidative rancidity. Antioxidants are used in meals to protect the lipid constituents from losing quality. The most widely utilised antioxidants are synthetic compounds like tert-butyl hydroquinone (TBHQ), butylated hydroxy toluene (BHT), propyl gallate (PG), and butylated hydroxy anisole (BHA). There is an increasing need for natural antioxidants because it is thought that these substances may function as carcinogenesis promoters. Additionally, antioxidants aid the body's defences against diabetes, cancer, arthritis, asthma, and cardiovascular disorders. Fresh herbs are considered to be good providers of natural antioxidants, so include them in your diet may help you meet your daily requirement. Due to natural antioxidant components, spices and herbs are great sources of antioxidants for food preservation. Therefore, use of spices and herbs present a better choice than synthetic antioxidants, which has become popular and is widely accepted by consumers. The main antioxidants found in spices are phenolic chemicals, and there is a linear correlation between the total phenolic content and the antioxidant effects of spices. Antioxidant capabilities can be found in essential oils, oleoresins, and even aqueous extracts of spices. All agree that the lamiaceae family of plants is a significant source of natural antioxidants. In both Europe and the United States, rosemary is a common antioxidant. The antioxidant capabilities of oregano, thyme, marjoram, sage, basil, fenugreek, fennel, coriander, and pimento are also superior to those of the synthetic antioxidant BHT.

A polypyrrole-cotton pad sorbent as micro-solid phase extractor enclosed in tea bag envelope for determination of synthetic antioxidants in non-alcoholic beverage products

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.

Synthesis, characterization, stereochemistry, antibacterial and antioxidant activity of N-chloroacetyl-2,6-diphenylpiperidines

A new series of N-chloroacetyl-2,6-diphenylpiperidines 13–18 have been synthesized from their corresponding piperidines 7–12. The synthesized compound 14 is unambiguously characterized using IR, mass, 1D and 2D (1H–1H, COSY & 1H–13C, HSQC) NMR spectral techniques and the remaining compounds 13–16 & 18 are characterized by IR, mass and 1D NMR spectra. The NMR spectral data indicate that the compound 17 prefers to adopt alternate chair conformation and remaining compounds prefer to adopt boat conformation. The X-ray crystal structure solved for N-chloroacetyl-3-isopropyl-2,6-diphenylpiperidine 16 supports the distorted boat conformation in the solid state. Anti-bacterial evaluation shows that the compounds 15 & 16 demonstrate superior activity against all the tested bacteria. All the synthesized compounds show promising antioxidant activities compared to the standard BHA (butylated hydroxyanisole).

Electrochemical sensor for determination of butylated hydroxyanisole in real samples using glassy carbon electrode modified by [Co(HL)2Cl2] nano-complex.

A new mononuclear Co(II) complex with the formula [Co(HL)2Cl2] (1) (HL= N-(2-hydroxy-1-naphthylidene)-2-methyl aniline) has been synthesized and characterized by Fourier transform infrared spectroscopy, UV-Vis, elemental analysis and single crystal X-ray structure analysis. Single crystals of the complex [Co(HL)2Cl2] (1) were obtained through slow evaporation of an acetonitrile solution at room temperature. The crystal structure analysis revealed that the two Schiff base ligands create a tetrahedral geometry via oxygen atoms and two chloride atoms. The nano-size of [Co(HL)2Cl2] (2) have been synthesized by the sonochemical process. Characterization of nanoparticles (2) was carried out via X-ray powder diffraction (XRD), scanning electron microscopy (SEM), UV-Vis, and FT-IR spectroscopy. The average sample size synthesized via the sonochemical method was approximately 56 nm. In this work, a simple sensor based on a glassy carbon electrode modified with [Co(HL)2Cl2] nano-complex was developed ([Co(HL)2Cl2] nano-complex/GCE) for convenient and fast electrochemical detection of butylated hydroxyanisole (BHA). The modified electrode offers considerably improved voltammetric sensitivity toward BHA compared to the bare electrode. Applying linear differential pulse voltammetry, a good linear relationship of the oxidation peak current with respect to concentrations of BHA across the range of 0.5-150 μM and a detection limit of 0.12 μM was achieved. The [Co(HL)2Cl2] nano-complex/GCE sensor was applied to the determination of BHA in real samples successfully.

Maximising olive oil by‐products

Maximising olive oil by‐products

Design, Synthesis, Characterization and Biological Evaluation of Para-Amino Salicylic Acid (PAS) Analogues: An Approach to Repurpose

The ever-emerging microbial resistance has imposed great challenges for the medicinal chemist in designing newer chemical entities, which is a lengthy and time-consuming process. An alternate approach of repurposing older drugs can be undertaken to accelerate the discovery of some newer derivatives with lesser side effects. The work reported in the present paper is an extension of the idea of repurposing older drugs. The study aimed to synthesize a series of ester and amide derivatives (P1-P28) of Para-amino salicylic acid. The antimicrobial evaluation of all the synthesized derivatives was performed via the serial dilution method. The Gram-positive bacteria: Staphylococcus aureus and Bacillus subtilis and Gram-negative bacteria: Escherichia coli and Pseudomonas aeruginosa were used for the antibacterial activity, and Candida albicans were used for the antifungal activity. Ciprofloxacin (antibacterial) and Fluconazole (antifungal) were the standard drugs. The antioxidant evaluation (ester derivatives, P1-P19) was carried out by using the DPPH scavenging method and BHA (butylated hydroxy anisole) was used as the reference. The derivative 5-acetamido-2-(propyl carbamoyl) phenyl acetate (P22) was the most effective antibacterial agent, which may be attributed to the presence of 3-carbon aliphatic alkyl chain. At the same time, 4-methoxy phenyl-4-amino-2-hydroxy benzoate (P15) and 2-chloro phenyl-4-amino-2-hydroxy benzoate (P16) displayed effective antifungal activity. Ethyl-4-amino-2-hydroxy benzoate (P2) demonstrated the most potent free radical scavenging activity. Further, the spectroscopic characterization and physicochemical characterization of the synthesized derivatives have been carried out and were found to be in accord with the assigned structures.

Comprehensive Metabolite Profiling of Berdav Propolis Using LC-MS/MS: Determination of Antioxidant, Anticholinergic, Antiglaucoma, and Antidiabetic Effects.

Propolis is a complex natural compound that honeybees obtain from plants and contributes to hive safety. It is rich in phenolic and flavonoid compounds, which contain antioxidant, antimicrobial, and anticancer properties. In this study, the chemical composition and antioxidant activities of propolis were investigated; ABTS•+, DPPH• and DMPD•+ were prepared using radical scavenging antioxidant methods. The phenolic and flavonoid contents of propolis were 53 mg of gallic acid equivalent (GAE)/g and 170.164 mg of quercetin equivalent (QE)/g, respectively. The ferric ion (Fe3+) reduction, CUPRAC and FRAP reduction capacities were also studied. The antioxidant and reducing capacities of propolis were compared with those of butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), α-tocopherol and Trolox reference standards. The half maximal inhibition concentration (IC50) values of propolis for ABTS•+, DPPH• and DMPD•+ scavenging activities were found to be 8.15, 20.55 and 86.64 μg/mL, respectively. Propolis extract demonstrated IC50 values of 3.7, 3.4 and 19.6 μg/mL against α-glycosidase, acetylcholinesterase (AChE) and carbonic anhydrase II (hCA II) enzyme, respectively. These enzymes' inhibition was associated with diabetes, Alzheimer's disease (AD) and glaucoma. The reducing power, antioxidant activity and enzyme inhibition capacity of propolis extract were comparable to those demonstrated by the standards. Twenty-eight phenolic compounds, including acacetin, caffeic acid, p-coumaric acid, naringenin, chrysin, quinic acid, quercetin, and ferulic acid, were determined by LC-MS/MS to be major organic compounds in propolis. The polyphenolic antioxidant-rich content of the ethanol extract of propolis appears to be a natural product that can be used in the treatment of diabetes, AD, glaucoma, epilepsy, and cancerous diseases.

A novel electrochemical detection method for butylated hydroxyanisole (BHA) as an antioxidant: a BHA imprinted polymer based on a nickel ferrite@graphene nanocomposite and its application.

A novel electrochemical detection method based on a nickel ferrite@graphene (NiFe2O4@Gr) nanocomposite-containing molecularly imprinted polymer (MIP) was developed for the sensitive determination of butylated hydroxyanisole (BHA). After successful completion of the nanocomposite production under hydrothermal conditions, the NiFe2O4@Gr nanocomposite and a novel molecularly imprinted sensor based on the NiFe2O4@Gr nanocomposite were characterized using microscopic, spectroscopic and electrochemical techniques. According to the characterization results, the synthesis of the core-shell type NiFe2O4@Gr nanocomposite with high purity and efficiency has been proved to be successful. After successful modification of a cleaned glassy carbon electrode (GCE) with the NiFe2O4@Gr nanocomposite, analytical applications were started with the prepared BHA printed GCE. This novel molecularly imprinted electrochemical sensor for BPA detection demonstrated a linearity of 1.0 × 10-11-1.0 × 10-9 M and a low detection limit (LOD, 3.0 × 10-12 M). In addition, the BHA imprinted polymer based on the NiFe2O4@Gr nanocomposite also exhibited excellent selectivity, stability, reproducibility and reusability performances in flour analysis.

Effect of thermal processing on the quality parameters of ghee incorporated with curry leaf (Murraya koeneigii) extract

This study examined the effect of adding antioxidants, namely curry leaf extract (CLE) and butylated hydroxyanisole (BHA), on the physicochemical properties of ghee during deep frying. The results showed that the addition of CLE to ghee resulted in significant changes in the L*, a*, and b* values, likely due to the extraction of chlorophyll molecules during CLE preparation. Deep frying caused a decrease in L* values and an increase in a* and b* values of ghee, as well as an increase in the redness and yellowness indices, with control ghee experiencing the most significant changes. The viscosity of ghee increased during frying, and the increase was less in ghee with added antioxidants. Antioxidant-added ghee showed the least increase in total polar compounds (TPC) and thiobarbituric acid reactive substances (TBARS) during frying, which are indicators of oil degradation. CLE and BHA were found to inhibit the production of Cholesterol Oxidation Products (COPs) in ghee during deep frying for up to 45 minutes. Control ghee showed the presence of both COPs (5α, 6α-epoxide and 7β-hydroxy cholesterol) after 45 minutes of frying, whereas ghee with added CLE and BHA had only 5α, 6α-epoxide after 45 minutes of frying.

Benzo(a)pyrene-induced mitochondrial respiration and glycolysis disturbance in human neuroblastoma cells.

Mammalian cells generate ATP through mitochondrial respiration and glycolysis. Mitochondria not only play a key role in cell energy metabolism but also in cell cycle regulation. As a neurotoxic pollutant, benzo(a)pyrene (BaP) can trigger neuronal oxidative damage and apoptosis. However, the features of BaP-induced energy metabolism disturbance in SH-SY5Y cells has rarely been addressed. This study aimed to measure oxygen consumption rate (OCR) and extracellular acidification rate (ECAR) as indications of respiratory activities and glycolytic. SH-SY5Y cells were treated with BaP to establish a cytotoxicity model, and butylated hydroxy anisole (BHA) was used to alleviate the damages induced by BaP. Using the Seahorse Extracellular Flux analyzer (XFp), we found that BaP significantly reduced basal respiration, ATP-linked OCR in SH-SY5Y cells with dose- and time-dependent. BHA supplementation recovered the mitochondrial respiration, synchronously attenuated intracellular ROS generation and lipid peroxidation, and simultaneously reversed the abnormal changes in antioxidant biomarkers, then rescued BaP-induced cell apoptosis. But long-term exposure to BaP or exposure to a high dosage of BaP could decrease OCR associated with maximal respiratory, spare capacity, and glycolysis metabolism. At the same time, the damage to cells is also more severe with the rate of apoptosis and mitochondrial membrane potential (ΔΨm) loss rising sharply, which were not entirely reversed by BHA. This study provides energy metabolism-related, indicative biomarkers of cytotoxicity induced by BaP, which might provide information for early prevention and intervention.

A lab-made screen-printed sensing strip for sensitive and selective electrochemical detection of butylated hydroxyanisole.

This study describes the fabrication of a lab-made screen-printed electrode (LabSPE) and its sensing ability for the detection of butylated hydroxyanisole (BHA) which is a synthetic antioxidant utilized widely in food industries. The lab-made screen-printed electrodes were printed on a polycarbonate substrate stepwise via a screen-printing technique using various inks suitable for electrode templates and then modified for the detection of BHA. As for the design of the sensor, firstly, graphitic carbon nitride (g-C3N4) was synthesized electrochemically through the one-pot synthesis method. After the synthesis of Fe3O4 nanoparticles (Fe3O4 NPs), the surface of SPE was modified with the dual composite consisting of g-C3N4 and Fe3O4 NPs. Lastly, platinum nanoparticles (Pt NPs) were deposited electrochemically on the modified electrode in 0.5 M HCl solution containing 2 mM H2PtCl6 at a constant potential of 0.25 V for 45 s. After optimization of varied parameters such as pH of the electrolyte solution, deposition time, and deposition potential, the current responses of the sensor (Pt/g-C3N4-Fe3O4/LabSPE) toward BHA displayed linearity in the wide concentration range of 0.25 μM to 90 μM with a low detection limit of 0.053 μM. The selectivity of Pt/g-C3N4-Fe3O4/SPE was tested successfully in the presence of other antioxidants (BHT, TBHQ, GA, and PG). Moreover, the applicability of the proposed sensor for practical tests was verified by the detection of BHA in commercial samples.

Antioxidant and Antimicrobial Properties of Ethanolic Extract of Lemon Verbena

Background and Objectives: Chemical preservatives are commonly used to prevent food from quick spoiling and oxidizing. Despite their effect in increasing shelf life of foods, these compounds can have side effects. Residues of chemical compounds in foods increase microbial resistance. This study aims to investigate the antioxidant and antimicrobial properties of lemon verbena (Lippia citriodora L.) ethanolic extract against some gram-positive and gram-negative bacteria. Methods: In this experimental study, The soaking method and ethanol solvent was used for extraction. Antioxidant activities of different concentrations of extract were assessed using DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity test and compared with butylated hydroxyanisole (BHA) as a synthetic antioxidant. Antimicrobial effect of extract on Staphylococcus aureus, Listeria innocua, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa and Salmonella typhimurium was determined by disk diffusion and well diffusion methods and measuring minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). Experimental data were analyzed in SPSS software, version 20 using analysis of variance and the mean values were compared using Duncan’s multiple range test. Results: The amounts of phenols and flavonoids in the ethanolic extract of were 96.47±0.35 mg of gallic acid/g of extract and 31.07±0.42 mg of quercetin/g of extract, respectively. The half-maximal inhibitory concentration of lemon verbena extract was 11.79±0.76 μg/mL, while it was 10.16±0.29 μg/mL for BHA. In both disk diffusion and well diffusion methods, with the increase of the concentration of extract, the inhibition zone diameter increased. The ethanolic extract of lemon verbena at the concentration of 12.5 mg/mL had no inhibitory effect on gram-negative bacteria growth. In both methods, the extract had the greatest effect on S. aureus. The MIC of ethanolic extract ranged from 8 to 128 mg/mL, depending on the type of bacteria (gram-positive or gram-negative). Conclusion: The ethanolic extract of lemon verbena has higher antimicrobial effects on gram-positive bacteria. Therefore, it can be used in food and pharmaceutical industries as a natural antimicrobial agent. Considering the increasing resistance of bacteria to chemical antibiotics, more studies on lemon verbena and its antibacterial compounds are needed for treating infections.

The key constituents underlying the combined toxicity of eight cosmetic contaminants towards Vibrio qinghaiensis.

Cosmetic additives (ADDs) and packaging plasticizers (PLAs) probably present potential risks and dangers to the environment and human body as emerging pollutants. To investigate their potential risks and dangers, five ADDs including methyl paraben (MET), ethyl paraben (ETH), propyl paraben (PRO), butyl-hydroxy anisole (BHA), and salicylic acid (SAL), as well as three PLAs including bisphenol A (BPA), bisphenol S (BPS) and tris(2-butoxyethyl) phosphate (TBEP) were selected as research objects, and ten mixture rays (R1-R10) composed of the eight components were designed by the uniform design ray (UD-Ray) method. The toxicities of the eight cosmetic pollutants and their eight-component mixture system towards Vibrio qinghaiensis sp.-Q67 (Q67) were systematically determined by the time-dependent microplate toxicity analysis (t-MTA) method. The three-dimensional (3D) surface of deviation from the concentration addition model (dCA) was utilized to qualitatively and quantitatively analyse the toxicity interaction of the mixtures and the correlation between toxicity interaction and the components' concentration ratios. Finally, eight individual pollutants and representative rays with significant inhibitory and interactive effects were selected to analyse DNA and soluble proteolysis as well as the microstructure and morphology of Q67 after treatment with single chemicals and their mixtures. The results showed that the eight cosmetic pollutants had conspicuous concentration-dependent toxicity and acute toxicity, and none of them, except BPS, BPA and ETH, had time-dependent toxicity. All rays had time/concentration-dependent toxicity and acute toxicity. At the same time, the toxicity interaction of these mixture rays was predominantly antagonism and the strongest antagonism appeared at high concentrations at 12 h. Nevertheless, the components' concentration ratio (pi) was the decisive factor for the type of mixture interaction. The correlation analysis revealed a significant positive linear correlation between mixture toxicity and pETH and pBPA, which indicated that ETH and BPA were the key components of the toxic effects. However, there was a significant negative linear correlation between the antagonism intensity and pBPA and pTBEP, which demonstrated that BPA and TBEP were the key components of the antagonism intensity. Pollutants and their mixtures can also damage cellular structures, and mixtures can exacerbate the dissolution of DNA and soluble proteins.

Composition and Antioxidant Ability of Extract from Different Flaxseed Cakes and Its Application in Flaxseed Oil.

In this research, extracts from five flaxseed cakes (hot-pressed cake (HPC), cold-pressed cake (CPC), n-hexane extracted cake (HEC), supercritical CO2 extracted cake (SCEC) and subcritical n-butane extracted cake (SBEC)) were analyzed for the contents of total phenolic, total flavonoid and antioxidant ability. At the same time, the antioxidant capacity of HPC extract and synthetic butylated hydroxyanisole (BHA) in the oxidative evolution of flaxseed oil was compared by accelerated storage experiment (8 days at 65°C). The results showed that compared with other flaxseed cake extract, the extract of HPC contained the highest content of total phenolic (78.01 mg GAE/g extract) and total flavonoid (2.73 mg RE/g extract), and showed the strongest antioxidant ability on DPPH, ABTS FRAP and total reducing power assay. We also found that different concentrations (800, 1000, 2000 ppm) of flaxseed cake extract could significantly slow down the oxidation of flaxseed oil during storage at 65°C, and the antioxidant effect strengthened with the increase of extract dosage. The antioxidant effect of the 2000 ppm extract was higher than that of 200 ppm BHA. The results indicated that flaxseed cake extract could effectively inhibit the oxidation of flaxseed oil and was a good substitute for synthetic antioxidants in oil industry.

Mathematical Mapping Study of Synthetic Antioxidants Behavior in Biodiesel: Application of the Self-Organized Feature Map (SOFM) and Multilayer Perceptron (MLP)

The objective of the present work was to apply self-organizing feature maps (SOFM) and multilayer perceptron (MLP) to evaluate the protective capacity of tert-butylhydroquinone (TBHQ), butylhydroxyanisole (BHA), and butylhydroxytoluene (BHT) antioxidants against the biodiesel oxidation reaction. For this, the antioxidant concentration and the biodiesel compliance parameters were used as continuous input variables and the type of antioxidant as a categorical. The SOFM proved to be an adequate tool for the classification of biodiesel samples containing antioxidants. The performance of the 5 most active networks of the model ranged from 89 to 99% for training, testing, and validation with an error below 1.42 × 10-4. Statistical tests applied to validate the model showed no significant difference between predicted and experimental values. The global sensitivity analysis showed that the relative protection factor (RPF) contributed with 34.89%, the antioxidant with 31.49%, the induction period with 10.69%, the water content with 6.00%, and the others all together with 16.93% in the construction of the regression models by MLP.

Detoxication of Citrinin with Kojic Acid by the Formation of the Citrinin-Kojic Acid Adduct, and the Enhancement of Kojic Acid Production by Citrinin via Oxidative Stress in Aspergillus parasiticus

Our previous work showed that citrinin (CTN) produced bay Penicillium citrinum inhibited the production of aflatoxin by Aspergillus parasiticus. We also reported that CTN was non-enzymatically converted to a novel CTN-KA adduct with kojic acid (KA) in aqueous condition. We herein observed that unlike CTN, the CTN-KA adduct does not show antimicrobial activity against Escherichia coli or Bacillus subtilis or any cytotoxic effect on HeLa cells, suggesting that CTN was detoxified by KA by the formation of the CTN-KA adduct. To examine the function of KA production by fungi, we isolated A. parasiticus mutants with impaired KA production. When the mutants were incubated in either liquid or agar medium supplemented with CTN, they were more susceptible to CTN than the wild KA-producing strain. The same results were obtained when we used the A. oryzae KA-producing strain RIB40 and KA-non-producing strains. When KA was added to the CTN-containing agar medium, the inhibition of growth by CTN was remarkably mitigated, suggesting that the production of KA protected the fungal growth from CTN's toxicity. We also observed that CTN enhanced the production of KA by A. parasiticus as well as A. oryzae strains. Reverse transcription-PCR showed that CTN enhanced the expression of KA biosynthetic genes (kojA, kojR, and kojT) of A. parasiticus. However, the enhancement of KA production with CTN was repressed by the addition of α-tocopherol or butylated hydroxy anisole, suggesting that KA production is enhanced by oxidative stress via the formation of reactive oxygen species caused by CTN. In contrast, α-tocopherol did not affect inhibition of AF production as well as fungal growth by CTN, suggesting that the regulation of these inhibitions with CTN might be different from that of KA production. We propose a regulation scheme of CTN for each of KA production, AF production, and fungal growth in A. parasiticus.

Total Phenolic Content, Antioxidant Properties and Element Concentrations of Methanol and Acetone Extracts of Stachys tmolea Boiss.

DPPH radical scavenging, total antioxidant status, phenolic and element concentrations of the different solvent extracts of Stachys tmolea Boiss. were determined in the study. It was found that, the methanol extract of the plant contains total phenolic substance is 68.91±1.4 mg Gallic acid equivalant/g extract. % DPPH radical inhibition was 64.79±1.98 and total antioxidant status was 2.28±0.21 mmol Trolox Equiv./L. The acetone extract contains total phenolic substance (27.26±1.2 mg GAE/g extract). % DPPH radical was 50.33±2.05, and total antioxidant status was 0.57±0.04 mmol Trolox Equiv./L. It is seen that, the methanol extract has properties close to the synthetic antioxidant butylated hydroxy anisole (total phenolic substance concentration is 82.33±2.1 mg GAE/g). It is determined that the species also contains elements such as Cu, Mn, and Fe that participate in superoxide dismutase and catalase. In conclusion, the methanolic extract of Stachys tmolea exhibits radical scavenging and antioxidative properties. The species is thought to be a plant that can evaluate in phytotherapy studies due to the important elements it contains.