ascorbic-acid and furan

Species of kalanchoe are rich in bioactive compounds and are widely used in folk medicine; however, these plants are not well known from the point of view of aroma. Two species, Kalanchoe pinnata and Kalanchoe daigremontiana, were examined after six months and two years of growth and their vitamin C content, succulence, and aroma composition were determined. The efficiency of juice extraction was highest (72%) for the leaves of K. daigremontiana after six months of growth. The concentration of vitamin C was highest in juices from two-year-old plants and much higher in the juice of K. pinnata (81 mg/100 g). SPME/GC/MS analysis identified 32 aroma components, considering those with the spectrum similarity over 75%. The main components were furan-2-ethyl, hexanal, 2-hexenal, 2,4-hexadienal, 1-octen-3-ol, nonanal. The quantitative relations of these compounds were somewhat different in the two species. The most dominant component, 2-hexenal, is responsible for the green-like aroma noted by the sensory panel.

Topics: Aldehydes; Alkadienes; Ascorbic Acid; Fruit and Vegetable Juices; Furans; Gas Chromatography-Mass Spectrometry; Kalanchoe; Octanols; Odorants; Plant Extracts; Plant Leaves; Principal Component Analysis

The objective of current study was to determine the furan levels in commercial orange juices (OJs) and relate to the sensory and quality characteristics of OJs. The factors among sensory and quality characteristics that showed high correlation to furan were identified. The furan levels found in 18 commercial OJs ranged from 0.59 to 27.39ng/mL. Freshly-squeezed type OJs (n=4) had significantly lower furan levels (4.68ng/mL) than other OJs treated with heat processing (p<0.05). Vitamin C content, specifically, dehydroascorbic acid showed higher correlation to the furan level in OJs (r=0.833). A descriptive sensory analysis result revealed the different flavor profile of commercial OJs according to the processing method and added ingredient in OJs. Current approach of using sensory analysis for prediction of furan level in food products can be applied to future studies in many other food commodities.

Topics: Ascorbic Acid; Citrus sinensis; Food Handling; Fruit and Vegetable Juices; Furans; Taste

3-Arylfuran-2(5H)-one derivatives show good antibacterial activity and were determined as tyrosyl-tRNA synthetase (TyrRS) inhibitors. In a systematic medicinal chemistry exploration, we demonstrated chemical opportunities to treat infections caused by Helicobacter pylori. Twenty 3-arylfuran-2(5H)-ones were synthesized and evaluated for anti-H. pylori, antioxidant and anti-urease activities which are closely interconnected with H. pylori infection. The results displayed that some of the compounds show excellent antioxidant activity, and good anti-H. pylori and urease inhibitory activities. Out of these compounds, 3-(3-methylphenyl)furan-2(5H)-one (b9) showed the most potent antioxidant activity (IC50=8.2 μM) and good anti-H. pylori activity (MIC50=2.6 μg/mL), and it can be used as a good candidate for discovering novel anti-gastric ulcer agent.

Topics: Anti-Bacterial Agents; Anti-Ulcer Agents; Antioxidants; Binding Sites; Drug Evaluation, Preclinical; Furans; Helicobacter pylori; Humans; Molecular Docking Simulation; Protein Structure, Tertiary; Stomach Ulcer; Tyrosine-tRNA Ligase; Urease

The aim of this study was to analyse and reduce furan in various model systems. Furan model systems consisting of monosaccharides (0.5M glucose and ribose), amino acids (0.5M alanine and serine) and/or 1.0M ascorbic acid were heated at 121°C for 25 min. The effects of food additives (each 0.1M) such as metal ions (iron sulphate, magnesium sulphate, zinc sulphate and calcium sulphate), antioxidants (BHT and BHA), and sodium sulphite on the formation of furan were measured. The level of furan formed in the model systems was 6.8-527.3 ng/ml. The level of furan in the model systems of glucose/serine and glucose/alanine increased 7-674% when food additives were added. In contrast, the level of furan decreased by 18-51% in the Maillard reaction model systems that included ribose and alanine/serine with food additives except zinc sulphate.

Topics: Amino Acids; Ascorbic Acid; Carcinogens; Chromatography, Gas; Color; Food Additives; Furans; Glucose; Hot Temperature; Maillard Reaction; Models, Biological; Reproducibility of Results

The formation and reduction of furan using a soy sauce model system were investigated in the present study. The concentration of furan fermented up to 30 days increased by 211% after sterilization compared to without sterilization. Regarding fermentation temperature, furan level after 30 days' fermentation was the highest at 30°C (86.21 ng/mL). The furan levels in the soy sauce fermentation at 20°C and 40°C were reduced by 45% and 88%, respectively compared to 30°C fermentation. Five metal ions (iron sulfate, zinc sulfate, manganese sulfate, magnesium sulfate, and calcium sulfate), sodium sulfite, ascorbic acid, dibutyl hydroxyl toluene (BHT), and butylated hydroxyanisole (BHA) were added in a soy sauce model system. The addition of metal ions such as magnesium sulfate and calcium sulfate reduced the furan concentration significantly by 36-90% and 27-91%, respectively in comparison to furan level in the control sample (p<0.05). Iron sulfate and ascorbic acid increased the furan level at 30 days' fermentation in the soy sauce model system by 278% and 87%, respectively. In the case of the BHT and BHA, furan formation generally was reduced in the soy sauce model system by 84%, 56%, respectively.

Topics: Ascorbic Acid; Butylated Hydroxyanisole; Calcium Sulfate; Fermentation; Ferrous Compounds; Food Handling; Furans; Gas Chromatography-Mass Spectrometry; Magnesium Sulfate; Manganese Compounds; Reproducibility of Results; Soy Foods; Sterilization; Sulfates; Sulfites; Temperature; Zinc Sulfate

This study aimed to investigate the effect of oxidizing and reducing agents on the formation of furan through ascorbic acid (AA) degradation during heating at elevated temperatures (≥100 °C) under low moisture conditions. To obtain these conditions, oxidizing agent, ferric chloride (Fe), or reducing agent, cysteine (Cys), was added to reaction medium. Kinetic constants, estimated by multiresponse modeling, stated that adding Fe significantly increased furan formation rate constant, namely 369-fold higher than that of control model at 100 °C. Rate-limiting step of furan formation was found as the reversible reaction step between intermediate (Int) and diketogluconic acid (DKG). Additionally, Fe decreased activation energy of AA dehydration and furan formation steps by 28.6% and 60.9%, respectively. Results of this study are important for heated foods, fortified by ferric ions and vitamins, which targets specific consumers, e.g. infant formulations.

Topics: Ascorbic Acid; Cooking; Furans; Kinetics; Oxidation-Reduction

Furan, a potential carcinogen, has been detected in highly consumed starchy foods, such as bread and snacks; however, research on furan generation in these food matrixes has not been undertaken, thus far. The present study explored the effect of ascorbic acid addition and cooking methods (frying and baking) over furan occurrence and its relation with the non-enzymatic browning in a wheat flour starchy food model system. Results showed that furan generation significantly increased in the presence of ascorbic acid after 7 min of heating (p < 0.05). The strongest effect was observed for baked products. Additionally, the furan content in fried products increased with the increase of the oil uptake levels. As for Maillard reactions, in general, the furan level in all samples linearly correlated with their degree of non-enzymatic browning, represented by L* and a* color parameters (e.g., wheat flour baked samples showed a R(2) of 0.88 and 0.87 for L* and a*, respectively), when the sample moisture content decreased during heating.

Topics: Ascorbic Acid; Cooking; Flour; Furans; Hot Temperature; Maillard Reaction; Starch; Triticum

In order to elucidate the effect on mammal systems of new derivatives from 2-hydroxy-3-allyl-naphthoquinone, alpha-iodinated naphthofuranquinone (NPPN-3223), beta-iodinated naphthofuranquinone (NPPN-3222) and beta-methyl naphthofuranquinone (NPPN-3226) synthesized as possible trypanocidal agents, their effect on rat liver microsomal lipid peroxidation was investigated. They (a) inhibited NADPH-dependent, iron-catalyzed microsomal rat liver lipid peroxidation; (b) did not inhibit the tert-butyl hydroperoxide-dependent lipid peroxidation; (c) did not inhibit ascorbate-lipid peroxidation with the exception of NPPN-3226 which did inhibit it; (d) stimulated NADPH oxidation and microsomal oxygen uptake; (e) increased superoxide anion formation by NADPH-supplemented microsomes and (f) stimulated ascorbate oxidation. The three drugs were reduced to their seminaphthofuranquinone radical by the liver NADPH-P450 reductase system, as detected by ESR measurements. These results support the hypothesis that naphthofuranquinones reduction by microsomal NADPH-P450 reductase and semiquinone oxidation by molecular oxygen diverts electrons, preventing microsomal lipid peroxidation. In addition, hydroquinones and/or semiquinones formed by naphthofuranquinones reduction would be capable of lipid peroxidation inhibition and on interacting with the lipid peroxide radicals can lead to an antioxidant effect as we suggested for NPPN-3226 in close agreement to the inhibition of ascorbate-lipid peroxidation. Due to the properties of these molecules and their incoming structure developments, naphthofuranquinones would be considered as potentially promising therapeutic agents, mainly against Chagas disease.

Topics: Animals; Ascorbic Acid; Benzoquinones; Furans; Lipid Peroxidation; Male; Microsomes, Liver; NADPH Oxidases; Naphthoquinones; Oxidation-Reduction; Oxidative Stress; Oxygen; Rats; Rats, Wistar; Reactive Oxygen Species; Superoxides; tert-Butylhydroperoxide

Furan, a potential carcinogen, can be induced by heat from sugars, ascorbic acid, and fatty acids. The objective of this research was to investigate the effect of pH, phosphate, temperature, and heating time on furan formation. Heat-induced furan formation from free sugars, ascorbic acid, and linoleic acid was profoundly affected by pH and the presence of phosphate. In general, the presence of phosphate increased furan formation in solutions of sugars and ascorbic acid. In a linoleic acid emulsion, phosphate increased the formation of furan at pH 6 but not at pH 3. When an ascorbic acid solution was heated, higher amounts of furan were produced at pH 3 than at pH 6 regardless of phosphate's presence. However, in linoleic acid emulsion, more furan was produced at pH 6 than at pH 3. The highest amount of furan was formed from the linoleic acid emulsion at pH 6. In fresh apple cider, a product with free sugars as the major components (besides water) and little fatty acids, ascorbic acid, or phosphate, small or very low amounts of furan was formed by heating at 90-120 degrees C for up to 10 min. The results indicated that free sugars may not lead to significant amounts of furan formation under conditions for pasteurization and sterilization. Importantly, this is the first report demonstrating that phosphate (in addition to pH) plays a significant role in thermally induced furan formation.

Topics: Ascorbic Acid; Beverages; Carbohydrates; Food Handling; Furans; Hot Temperature; Hydrogen-Ion Concentration; Linoleic Acid; Malus; Phosphates

Previous model studies have suggested ascorbic acid as one of the major sources of furan, a possibly hazardous compound found in thermally processed foods (e.g. canned products, jars). The study showed that about 2 mmol mol(-1) furan was obtained when dry-heating ascorbic acid, while much lower amounts were formed upon pressure cooking, i.e. 58 micromol mol(-1) at pH 4 and 3.7 micromol mol(-1) at pH 7. Model reactions also generated 2-methylfuran (MF). However, the MF levels were generally very low with the exception of the binary mixture ascorbic acid/phenylalanine (1 mmol mol(-1)). Studies with 13C-labelled ascorbic acid indicated that furan comprises an intact C4 unit, mainly C-3 to C-6, generated by splitting off two C1 units, i.e. CO2 and formic acid. Possible intermediates are 2-deoxyaldoteroses, 2-furoic acid and 2-furaldehyde, which are known as ascorbic acid degradation products. The mechanism of furan formation from ascorbic acid was validated based on the labelling pattern of furan and the identification of 13CO2 and H13COOH. Furan formation is significantly slowed down in binary mixtures, e.g. the presence of erythrose led to 80% less furan under roasting conditions. This is most likely due to competing reactions in complex systems, thus disfavouring furan formation. The mitigation effect is because furan, contrary to MF, is formed without recombination of ascorbic acid fragments. Therefore, furan levels are definitely much lower in foods than expected from trials with pure ascorbic acid. Consequently, conclusions should be drawn with much caution from model reactions, avoiding extrapolation from oversimplified model systems to food products.

Topics: Amino Acids; Ascorbic Acid; Carcinogens, Environmental; Cooking; Dehydroascorbic Acid; Food Analysis; Food Contamination; Fruit; Furans; Gas Chromatography-Mass Spectrometry; Glucose; Hot Temperature; Hydrogen-Ion Concentration; Models, Biological; Solid Phase Microextraction; Tetroses; Vegetables

The formation of furan as influenced by temperature and time of heating was studied in hazelnuts. Temperature was noted as the important processing parameter on the formation of furan in hazelnuts. The formation of furan was noticeably increased at temperatures exceeding 120 degrees C. Furan concentrations tended to increase linearly at 100 and 150 degrees C up to 60 min of heating. Detailed examination of the composition of different hazelnut varieties showed that certain precursors such as polyunsaturated fatty acids (linoleic acid), amino acids (threonine and alanine), and sugars (glucose) were present in hazelnut at amounts sufficient to generate significant amounts of furan upon heating. The composition of the lipid fraction in terms of relative percentages of fatty acids was relatively stable during heating at 150 degrees C for 30 min, but the concentrations of amino acids and sugars decreased significantly at the end of the heating period. This led to the conclusion that the Maillard reaction is possibly the primary mechanism responsible for the formation of furan in hazelnuts during heating.

Topics: Amino Acids; Ascorbic Acid; Carcinogens, Environmental; Cooking; Corylus; Fatty Acids, Nonesterified; Fructose; Furans; Glucose; Hot Temperature; Lipids; Sucrose

Furan has recently received attention as a possibly hazardous compound occurring in certain thermally processed foods. Previous model studies have revealed three main precursor systems producing furan upon thermal treatment, i.e., ascorbic acid, Maillard precursors, and polyunsaturated lipids. We employed proton transfer reaction mass spectrometry (PTR-MS) as an on-line monitoring technique to study furan formation. Unambiguous identification and quantitation in the headspace was achieved by PTR-MS/gas chromatography-mass spectrometry coupling. Ascorbic acid showed the highest potential to generate furan, followed by glyceryl trilinolenate. Some of the reaction samples generated methylfuran as well, such as Maillard systems containing alanine and threonine as well as lipids based on linolenic acid. The furan yields from ascorbic acid were lowered in an oxygen-free atmosphere (30%) or in the presence of reducing agents (e.g., sulfite, 60%), indicating the important role of oxidation steps in the furan formation pathway. Furthermore, already simple binary mixtures of ascorbic acid and amino acids, sugars, or lipids reduced furan by 50-95%. These data suggest that more complex reaction systems result in much lower furan amounts as compared to the individual precursors, most likely due to competing reaction pathways.

Topics: Ascorbic Acid; Fatty Acids, Unsaturated; Food Handling; Furans; Gas Chromatography-Mass Spectrometry; Hot Temperature; Linoleic Acid; Maillard Reaction; Mass Spectrometry; Methylation

This study was conducted to investigate the formation of furan from sugars, ascorbic acid, and organic acids as affected by ionizing radiation and thermal treatments. Results showed that both thermal treatments and irradiation induced formation of furan from ascorbic acid, fructose, sucrose, or glucose. Little furan was produced from malic acid or citric acid. The pH and concentration of sugars and ascorbic acid solutions had profound influences on furan formation due to either irradiation or thermal treatment. The rate of irradiation-induced furan formation increased with decreasing pH from 8 to 3. Approximately 1600 times less furan was formed at pH 8 as apposed to pH 3. At the same pHs, the amounts of furan formed from irradiation of ascorbic acid, fructose, and sucrose were always higher than from glucose. As pH decreased from 7 to 3, an increase in thermally induced furan was observed for sucrose and ascorbic acid solutions, but for glucose solution, less furan was formed at pH 3 than at pH 7. The levels of sugars commonly found in fruits and fruit juices, upon irradiation, would be high enough to potentially produce low parts per billion (ppb) levels of furan. The concentration of ascorbic acid at which a maximum of furan was produced upon irradiation was about 0.5 mg/mL, a level commonly found in some foods. Five furan derivatives were tentatively identified in thermally treated ascorbic acid solution, while one furan derivative was tentatively found in both irradiated and thermally treated samples.

Topics: Ascorbic Acid; Carbohydrates; Cesium Radioisotopes; Furans; Hot Temperature; Hydrogen-Ion Concentration

Studies performed on model systems using pyrolysis-GC-MS analysis and (13)C-labeled sugars and amino acids in addition to ascorbic acid have indicated that certain amino acids such as serine and cysteine can degrade and produce acetaldehyde and glycolaldehyde that can undergo aldol condensation to produce furan after cyclization and dehydration steps. Other amino acids such as aspartic acid, threonine, and alpha-alanine can degrade and produce only acetaldehyde and thus need sugars as a source of glycolaldehyde to generate furan. On the other hand, monosaccharides are also known to undergo degradation to produce both acetaldehyde and glycolaldehyde; however, (13)C-labeling studies have revealed that hexoses in general will mainly degrade into the following aldotetrose derivatives to produce the parent furan-aldotetrose itself, incorporating the C3-C4-C5-C6 carbon chain of glucose (70%); 2-deoxy-3-ketoaldotetrose; incorporating the C1-C2-C3-C4 carbon chain of glucose (15%); and 2-deoxyaldotetrose, incorporating the C2-C3-C4-C5 carbon chain of glucose (15%). Furthermore, it was also proposed that under nonoxidative conditions of pyrolysis, ascorbic acid can generate the 2-deoxyaldotetrose moiety, a direct precursor of the parent furan. In addition, 4-hydroxy-2-butenal-a known decomposition product of lipid peroxidation-was proposed as a precursor of furan originating from polyunsaturated fatty acids. Among the model systems studied, ascorbic acid had the highest potential to produce furan, followed by glycolaldehyde/alanine > erythrose > ribose/serine > sucrose/serine > fructose/serine > glucose/cysteine.

Topics: Acetaldehyde; Aldehydes; Amino Acids; Ascorbic Acid; Carbohydrates; Food Contamination; Food Preservation; Furans; Gas Chromatography-Mass Spectrometry; Hexoses; Hot Temperature