Orotic Acids Research Articles

BIOCHEMICAL INDICATORS OF RED WINES FROM VARIETIES BRED BY ALL-RUSSIAN RESEARCH YA.I. POTAPENKO INSTITUTE FOR VITICULTURE AND WINEMAKING

The results of the study of physical and chemical parameters and the main bio-logically valuable substances in dry red wines made from new promising grape varieties bred by All-Russian Research Ya.I. Potapenko Institute are presented. Magic, Black Pearl, Vesta, Augusta. Cabernet Sauvignon was taken as a control variety. The amount of anthocyanins in the wort of the Augusta variety exceeded the value in the control variety and amounted to 689.0 mg/dm3, and the mass concentration of phenolic substances was also maximum and amounted to 1456 mg/dm3. Wine materials prepared from the studied grape varieties received high tasting scores of 8.6 −8.8 points. According to the content of resveratrol, a sample from the Vesta variety stood out − 5.32 mg/dm3, The content of 3.5 − diglycoside in the studied wines was not higher than the established norms (EC No. 1493/1999, Article 19 and EU No. 883/2001, Article 21). The highest value was noted in the August variety 12.68 mg/dm3. In the studied wine materials, the following were determined: ascorbic, chlorogenic, nicotinic, orotic, caffeic and galic acids.

РЕАКЦИЯ СОРТА КИШМИШ СТОЛЕТИЕ НА НАГРУЗКУ КУСТОВ ПОБЕГАМИ И ГРОЗДЯМИ В УСЛОВИЯХ ЦЕНТРАЛЬНОЙ АГРОЭКОЛОГИЧЕСКОЙ ЗОНЫ ВИНОГРАДАРСТВА ПО КАЧЕСТВЕННЫМ КРИТЕРИЯМ

The presence of organic acids and cations, amino acids, sugars and other substances in grapes and products of its processing affects their taste and nutritional properties. The pools of these substances were studied in grapes of the Centennial Seedless variety with different bush load with shoots and bunches. To determine the composition and content of these substances in grape juice, classical instrumental methods and a capillary electrophoresis system, “Kapel-104T” and “Kapel-105M”, OOO NPF “LUMEX”, were used. Tartaric, acetic and malic acids have been identified in the juice. Significant contents of resveratrol, ascorbic, chlorogenic, nicotinic, orotic acids, proline, valine, and α-alanine were also found. The highest concentrations were observed in the variant with an average bush load with shoots and bunches.

Comparison of camel, buffalo, cow, goat, and sheep yoghurts in terms of various physicochemical, biochemical, textural and rheological properties

Comparative physicochemical, biochemical, textural, and rheological properties of yoghurts produced using buffalo, camel, cow, goat, and sheep milk were analysed. The physicochemical, textural, and rheological properties were determined over a 14-day storage period. Different animal milk types had a significant effect on all physicochemical analyses, fatty acid composition, conjugated linoleic acid content, cholesterol content, all amino acids except asparagine, ACE inhibitory activity, citric acid, and orotic acid, as well as other textural and rheological properties, except flow index n parameter. The storage period had a very significant effect on titratable acidity, pH value, firmness, consistency, cohesiveness, and yield stress τ0 parameters. Compared with other yoghurts studied, camel yoghurt was richer in terms of myristic acid from saturated fatty acids, ∑PUFA, arginine, lysine, phenylalanine, tryptophan, valine from essential amino acids, glutamic acid, and proline from non-essential amino acids, ACE inhibitory activity value, and hippuric and orotic acids.

Biochemical composition of ciders from various raw materials

Apple tree is the most common among other fruit crops. Apple fruit is the primary raw material used in cider making. Although the majority of Russian regions are rich in raw materials for the production of high-quality cider, the development of this industry is hampered by a number of issues. As a result, the domestic market sometimes offers low-quality and adulterated products. In this work, we study the organoleptic and biochemical indicators (volatile components, metal cations, phenolcarboxylic acids and organic acids) of fermented diffused apple juice and ciders prepared from both freshly squeezed and reconstituted apple juice. The biochemical composition and organoleptic characteristics of samples were determined by conventional methods, such as high-performance liquid chromatography (organic acids), capillary electrophoresis (phenolcarboxylic acids) and gas chromatography (volatile components). The concentrations of most of the studied parameters and organoleptic indicators werehigher in ciders from fresh apple juice. However, in the fermented diffused juice, the concentrations of chlorogenic (9.5 g/dm3), orotic (1.9 g/dm3) and gallic (4.7 mg/dm3) acids, as well as furfural (11.84 mg/dm3), exceeded those in other studied samples. Future research should investigate the possibility of secondary use of apple pomace, e.g., for the production of fruit spirits. Involvement of such raw materials ensures the rational use of secondary raw materials.

Measurement of carbohydrates and organic acids in varieties of cheese using high-performance liquid chromatography.

Lactose is converted to lactic acid through fermentation and ripening of cheese using starter cultures. The content of lactic acid and organic acids formed during storage of cheese is different based on the type of starter cultures, pH, processing, and storage conditions. The objective of this study was to determine the carbohydrates and organic acids of four different commercial cheese samples (Parmesan, Mozzarella, Swiss, and Cheddar cheese) using high-performance liquid chromatography (HPLC). The lactose content in Cheddar cheese was significantly high (p<.05) as compared to Parmesan cheese while Mozzarella and Swiss cheese did not have lactose. However, galactose was low in Swiss cheese as compared to other cheese types, while glucose did not detect in all cheese samples. Organic acids such as citric, succinic, lactic, and butanoic acids were high in Parmesan cheese relative to other cheese types. Additionally, pyruvic and propanoic acids were high (p<.05) in Swiss cheese while acetic and orotic acids were elevated (p<.05) in Mozzarella cheese relative to other types of cheese.

Nutritional Supplementation of Yogurt with Jerusalem Artichoke Tubers: Organic Acid Profiles and Quality Parameters.

Jerusalem artichoke (Helianthus tuberosus L.), also called wild sunflower, belongs to the Asteraceae family and is cultivated widely across the temperate zone for its nutritious tuber, which is used as a root vegetable. In this study, the Jerusalem artichoke (JA) was used as a supplementary additive for producing a functional yogurt, with enhanced health benefits and improving the microbiological, rheological, and sensorial quality characteristics of the product. The effects of the three different concentrations (1%, 2%, and 3%, w/w) of JA on the physicochemical properties, bacterial counts, sensorial properties, and organic acid profiles of yogurts were determined after 1, 7, 14, and 21 days of storage at ±4 °C. The results obtained revealed that with the addition of different concentrations of JA the overall parameters were statistically significant (p &lt; 0.01 and p &lt; 0.05) except for apparent viscosity, Streptococcus thermophilus, yeast and mold count, pyruvic ratios, and scores of flavor. Similarly, some parameters (fat ratio, yeast and mold count, concentrations of propionic, acetic, pyruvic, orotic, and lactic acids, and scores of appearance, consistency, and odor) changed depending on the storage time, while some did not show any changes regarding storage time. There was a relationship found between the concentration of JA and organic acid ratio (except for pyruvic acid) concentration in the yogurt samples. In conclusion, the research revealed the effect of JA in yogurt production as a thickener, flavor enhancer, prebiotic agent, and source of organic acids and bioactive compounds. The results indicate that JA has a good potential for enhancing the nutritional and physicochemical properties of the studied yogurt.

Identification of mare milk adulteration with cow milk by liquid chromatography-high resolution mass spectrometry based on proteomics and metabolomics approaches

Mare milk(MM)production is lower than that of cow milk (CM), making it a premium product. Unfortunately, sellers adulterate MM with cheap CM to unscrupulously gain more profits. This study aimed to analyze MM adulteration with CM using proteomics and metabolomics. Using univariate and multivariate statistical analysis, the relative abundances of certain proteins of caseins and secretoglobin family 1D member were found to be higher with a higher CM admixture percentage. In addition, several metabolites, such as orotic and 4-aminonicotinic acids, increased in the mare-cow milk mixture with an increased CM percentage. Accordingly, these proteins and metabolites distinguished MM adulterated with CM at levels as low as 1 %.These findings can serve as the basis for clarifying the differences at the proteome and metabolome in milk from minor dairy animals and ensure milk authenticity.

Effect of Cephalosporin Antibiotics on the Activity of Yoghurt Cultures.

The presence of antibiotics in milk is a significant problem affecting the technological safety of dairy products. The aim of the study was to determine the sensitivity of yoghurt cultures to residual levels of selected cephalosporin antibiotics (cephalexin, cefoperazone, cefquinome, cefazolin, and ceftiofur). Five yoghurt cultures were selected containing strains of Lactobacillus delbrueckii subsp. bulgaricus and Streptococcus thermophilus. Artificially fortified milk samples (whole pasteurized milk; 85 °C; 3–5 s) with cephalosporins at a concentration of the maximum residue limit were used to evaluate the sensitivity of the yoghurt cultures by monitoring the pH, titratable acidity, and the concentration of selected organic acids (lactic, pyruvic, citric, acetic, orotic, oxalic, formic, uric, and succinic acids) at the end of fermentation (43 °C; 4–5.5 h; pH ≤ 4.6). The titratable acidity was determined by the Soxhlet–Henkel method and the organic acid concentration was monitored by reversed-phase HPLC. Ceftiofur had the greatest effect on the yoghurt culture activity, with a statistically highly significant effect (p < 0.05) on the pH, titratable acidity, and the content of lactic, pyruvic, and acetic acids in all cultures. Other cephalosporins also showed an inhibitory effect on yoghurt metabolism as seen by the evaluation of the lactic and pyruvic acid concentrations.

Effect of midday pasteurizer washing on thermoduric organisms and their progression through Cheddar cheese manufacturing and ripening

Thermoduric bacteria are known to affect the quality of Cheddar cheese, with manifested defects including slits, weak body, and blowing. Thermoduric bacteria are likely to increase in numbers during cheese-making, as in-process conditions are conducive to proliferation. The present study was conducted to track thermoduric bacterial progression during an 18- to 20-h Cheddar cheese production run and during ripening when the pasteurizer was washed at midway through the production day. This study also correlated a broad range of chemical changes to the growth of thermoduric bacteria during ripening. Three independent cheese trials were performed at 3.5- ± 0.5-mo intervals. Samples were drawn in duplicates at 4 different times of the day: at the start of the run (vat 1), prior to a midday wash of the pasteurizer (vat 20), after the midday wash of the pasteurizer (vat 21), and at the end of the run (vat 42) for raw milk, pasteurized milk, and cheese. Cheeses were also tested during ripening for 6 mo. Results showed that raw milk total bacterial counts comprised 0.24% thermoduric mesophiles (TM) and 0.12% thermoduric thermophiles (TT). The thermoduric thermophilic bacterial counts increased by log10 1.23 during the pasteurizer run of 9 to 10 h, indicating a buildup of thermoduric thermophilic bacteria during the pasteurization process itself. Midday washing reduced thermophilic counts by log10 1.36, as evident by pre- and post-midday wash counts. However, a thermophilic buildup during post-midday wash was again noticed near the end of the 20-h run. We found that TT bacteria decreased in the first 60 d of ripening, whereas TM bacteria increased during the same period. However, TT bacteria increased later during 60 to 180 d of ripening. Bacillus licheniformis was the most frequently isolated bacteria in this study and was recovered at all production stages sampled during the cheese-making and ripening. We observed a significant increase in the level of orotic and uric acids in the vat made at the end of the day. No significant difference in the overall chemical composition, proteolysis, sugar, or other organic acids was observed in cheese made at the start versus the end of the production run.

Синтез новых производных 6-гидроксипиримидин-4(3Н)-она

In this paper, 6-hydroxypyrimidine-4 (3Н)-one derivatives are considered as promising syntones for the creation of new biologically active substances. This is useful since the pyrimidine fragment is a structural component of nucleic acid bases (cytosine, thymine, uracil), uric and orotic acids, coenzymes (flavins and xanthins), a number of vitamins (folic acid, thiamine, pyridoxine, riboflavin). It is worth noting that the pharmaceutical market is widely represented with antitumor (methotrexate, imatinib, tegafur); antiviral (stavudine, zalcitabine, lamivudine, zidovudine, acyclovir, idoxuridine); immunostimulatory (isophone) and sedative drugs (phenobarbital, sodium ethaminal) based on compounds including the pyrimidine cycle. The purpose of the present work is to develop a method for producing new 2,3-diphenyl-5-(alkyl/ phenyl)-6-hydroxypyrimidin-4(3Н)-ones, proving their structure and individuality by NMR spectroscopy and mass spectrometry, elemental analysis and thin-layer chromatography. As a method of producing new 6-hydroxypyrimidin-4(3Н)-ones, a method of condensing N-phenyl-benzenecarboxymidamide with 2-substituted propanedioyldichlorides in the medium of an aprotic non-polar solvent – o-xylene is proposed. The desired products are isolated from the reaction mass using solvent distillation and a reprecipitation method. It was found that maximum yields are achieved with constant stirring of a suspension of N-phenylbenzenecarboxymidamide with a solution of 2-substituted propanedioyl dichloride in o-xylene and further heating of the reaction mass at 144 °C for 4 hours. The individuality of the synthesized compounds was confirmed by thin layer chromatography on Sorbfil® plates in the methanol-dichloroethane (1:9) system, and their structure was proved using modern physicochemical analysis methods: proton magnetic resonance spectroscopy, NMR С13 spectroscopy, mass spectroscopy and elemental analysis.

A Severe Neonatal Argininosuccinic Aciduria Case Investigated by 1H NMR Spectroscopy

The NMR urine analysis of a term newborn with severe general deterioration of the clinical state revealed the presence in high concentrations of orotic and argininosuccinic acids. The newborn was suspected for an intoxication-like inborn error of metabolism, and the urine samples were followed up by NMR spectroscopy for several days in order to assess the metabolic pattern. The identified markers led to a definitive biochemical diagnosis of argininosuccinic aciduria.

Energetic characterization of uracil derivatives: Orotic and isoorotic acids

The standard (po =0.1 MPa) molar enthalpies of formation of orotic and isoorotic acids, in the crystalline phase, were derived from the respective standard massic energies of combustion measured by static bomb combustion calorimetry, in oxygen, at T =298.15 K, as ‒821.7 ± 1.1 kJ mol−1 and ‒838.3 ± 1.9 kJ mol−1, respectively.The molecular structure and conformational behaviour of orotic and isoorotic acids were studied by theoretical calculations and the standard gas-phase molar enthalpies of formation were derived using an appropriate set of working reactions.Sublimation enthalpies, at the reference temperature T = 298.15 K, were estimated from difference between crystalline and gaseous enthalpies of formation and from statistically-based interaction indices derived from molecular surface electrostatic potentials.

Effects of Waiting Period before Milking on Orotic, Uric and Hippuric Acid Contents of Milks from Shami and Kilis Goats

The organic acids present in milk in varying quantities can reflect the health condition of the animals and the nutritional quality of milk. In rural areas, goats are maintained in pasture during whole day and milking is being started as soon as goats arrive to farm. However, it is not known whether milking during feeding as soon as goats return from pasture or after 1 hour-waiting have any effect on nitrogen-containing organic acids are the body metabolism products. Therefore, in this study we objected to determine the effects of 1 hour-waiting period before milking on orotic, uric and hippuric acids of milks from “Shami (Damascus)” and “Kilis” goat breeds during lactation period. The trial was carried out with 40 goats. The 20 goats from each breed were randomly separated to two groups at equal number. Control and experimental groups of the both breeds were milked during feeding as soon as goats return from pasture and after 1 hour-waiting following feeding, respectively. The milk samples taken with interval 30 days from May to October were used for organic acid analysis at a reverse phase high performance liquid chromatography. During lactation hippuric acid was the most abundant organic acid, followed by orotic and uric acids. Experimental group of Kilis goats had the highest level of hippuric acid. Orotic acid was higher in Shami goats than that in Kilis breed. Uric acid was the highest in control group of Shami breed. The 1 hour-waiting period before milking resulted in a significant decrease in uric acid. In general, orotic and uric acid decreased towards the end of lactation whereas hippuric acid markedly increased in the last 3 months of lactation. It was concluded that the 1 hour-waiting before milking after returning from pasture may be especially suggested to Shami goat raisers due to the low uric acid content of the milk.

Multicomponent solids of uracil derivatives – orotic and isoorotic acids

Cocrystallization of two multifunctional structural isomers viz. orotic and isoorotic acids was explored with a series of amine and pyridine-based coformers.

Theoretical Models for Quantitative Description of the Acid-Base Equilibria of the 5,6-Substituted Uracils.

The acidities of 18 5,6-substituted uracils have been numerically estimated as pKa values in terms of three theoretical models. The first scheme includes the calculation of the gas-phase acidity of uracil with the G3MP2B3 method and taking into account the solvent effect using the polarizable continuum approximation PCM(SMD)-TPSS/aug-cc-pVTZ. The second model is one step and implies calculation of the free Gibbs energies of the hydrate complex of uracil (and its anion) with 5 water molecules by the TPSS/aug-cc-pVTZ method. This model accounts for the solvent effect corresponding to both specific and nonspecific solvation. The third scheme required high time and computational resources and includes the strong features of the two previous schemes. Here, the theoretical estimation of pKa is performed by the CBS-QB3 composite method. As in the second approach, both specific (as pentahydrate) and nonspecific solvent effects are determined. We have analyzed the advantages and model restrictions of the considered schemes for the pKa calculations. All models have systematic errors, which have been corrected with the linear empirical regression relations. In the presented model, the absolute mean deviations of the pKa values of uracils dissociating via the N1-H bonds diminish to 0.25, 0.28, and 0.23 pKa units (respectively, for I, II, and III models), which corresponds to ∼0.3 kcal/mol on the energy scale. The applicability of our computational schemes to uracils dissociating via N3-H, O-H (orotic acids) and C-H bonds is discussed.

Characterization of volatile compounds and organic acids in ultra-high-temperature milk packaged in tetra brik cartons

ABSTRACTA study was conducted to evaluate the basic chemical composition, organic acids and volatile compound profiles of ultra-high-temperature milk samples sold in Turkey. The organic acids were determined by reverse-phase high-performance liquid chromatography method, and volatile compounds were analyzed by headspace solid phase micro-extraction/gas chromatography/mass spectrometry technique. A total of 43 volatile compounds including 4 aldehydes, 5 alcohols, 10 ketones, 9 acids, 9 aromatic hydrocarbons, 3 nitrogenous, 2 sulfur containing compounds, and 1 alkane hydrocarbon, were identified in the ultra-high-temperature milk samples. The main compounds were found to be oxime methoxy phenyl, 2-heptanone, 2-mercapto-4-phenylthiazole, 2-amino-5-ethoxycarbonyl benzophenone, acetic acid, 2,6,10,14-tetramethyl pentadecane, and 2-nonanone. The main organic acid in the ultra-high-temperature milk was citric acid a mean value of 133 mg/100 mL, followed by formic, lactic, succinic, oxalic, acetic, orotic, propionic, pyruvic, hippuric, and uric acids.

A LFER Kinetic Study of The Reaction of 5‐Substituted Orotic Acids with Diazodiphenylmethane

ABSTRACTLinear free energy relationships (LFER) were applied to the kinetic data for the reaction of 5‐substituted orotic acids, series 1, with diazodiphenylmethane (DDM) in N,N–dimethylformamide and compared with results obtained for 2‐substituted benzoic acids, series 2. The correlation analysis of the kinetic data with σ substituent parameters was carried out using SSP (single substituent parameter) methods. From the sign and value of proportinality constant ρ, lower sensitivity to the substituent effect was obtained in series 1, 0.876, than in the series 2, 1.877. Evaluation of substituent “ortho‐effect” was performed using the Charton model, which includes the steric substituent parameter, and Fujita and Nishioka's model, which describes the total ortho‐effect as contribution of ordinary polar effect, the ortho‐steric and ortho‐polar effects. Results of correlations, obtained by using the Charton model, showed highest contribution of the polar effect, 0.861 vs. 2.101, whereas the steric effect is of lowest significance, 0.117 vs. 0.055, for series 1 and 2, respectively. Also, a low negative value of coefficient with the steric effect, –0.08, obtained from the Fujita–Nishioka model indicated low steric effect, influencing a decrease of the reaction rate in series 1. The structural and substituent effects were also studied by using the density functional theory method, and together with kinetic data, it gave a better insight into the influence of the effect of both geometry and substituent on the π−electron density shift induced reactivity of investigated acids.

Organic acids profiles in lactose-hydrolyzed yogurt with different matrix composition

The composition of the dairy matrix used in yogurt manufacture could influence the metabolic activity of yogurt starter and the compounds produced during fermentation. In this way, the lactose hydrolysis with a β-galactosidase enzyme and the supplementation with dairy powders to obtain different types of delactosed yogurts for lactose-intolerant people modifies the milk base composition. In this work, we studied the influence of the addition of different doses of β-galactosidase and levels of dairy powders on organic acids profile during the manufacture and storage of two varieties of yogurt (natural and sweetened). Lactose, glucose, galactose, titratable acidity, fermentation time, and microbiological counts were also evaluated. The mean proportions of lactose/glucose/galactose in relation to the total sugars were 18:36:46 in hydrolyzed yogurts, while they were 81:4:15 in unhydrolyzed ones. In supplemented yogurts, the content of lactose, citric, orotic, and hippuric acids were significantly increased. The starter population was similar in all yogurts, but some changes in their activity were evidenced due to both factors studied. The fermentation time was slightly increased, and the lactic acid content and the titratable acidity were significantly increased due to fortification while they were decreased by enzyme addition. These results are probably due to the increase in the buffer properties of the milk base by the dairy powder addition and due to an inhibition of the starter activity caused by changes in the carbohydrate profile. The results demonstrated that the changes in the matrix composition of the yogurt affected the organic acids profile, above all the lactic acid content.

Profiles of Organic Acid and Volatile Compounds in Acid-Type Cheeses Containing Herbs and Spices (Surk Cheese)

A study was conducted to evaluate the basic chemical composition, organic acids, volatile compound profiles, and overall acceptability of Surk cheese (acid cheese). The organic acids were determined by reverse phase high performance liqued chromatography method, and volatile compounds were analyzed by static headspace/gas chromatography/mass spectrometry technique. A total of 134 volatile compounds, including 42 esters, 40 terpenes, 15 alcohos, 11 free fatty acids, 6 ketones, 5 aldehydes, 4 alkenes, 4 phenyl propanoids, 3 phenolics, and 4 other compounds, were identified in the Surk cheeses. The main compounds were found to be carvacrol, γ-terpinene, p-cymene, hexanoic acid, octanoic acid, decanoic acid, butanoic acid, and eugenol. The mean total organic acid content of the Surk cheese was 1.71 g/100 g. The main organic acid in the Surk cheese was lactic acid (1067 mg/100 g), followed by acetic, propionic, oxalic, formic, citric, pyruvic, orotic, hippuric, and uric acids.

Synthesis of imines based on orotic aldehyde and amino acids

Synthesis of imines based on orotic aldehyde and amino acids