A series of hybrid compounds with triazole and thiazolidine nuclei connected by a linker has been synthesized and extensively studied. Various synthetic methods for the target compounds have been tested. A microbiological assessment of the obtained compounds was carried out on strains of pathogenic fungi C. albicans, C. non-albicans, multidrug-resistant C. auris, Rhizopus arrhizus, Aspergillus spp. and some dermatophytes and other yeasts. The lowest obtained MIC values for target compounds lie between 0.003 µg/mL and 0.5 µg/mL and therefore the compounds are not inferior or several times better than commercial azole drugs. The length of the acylpiperazine linker has a limited effect on antifungal activity. Some bioisosteric analogues were tested in microbiological analysis, but turned out to be weaker than the leader in activity. The highest activity was demonstrated by a compound with para-chlorobenzylidene substituent in the thiazolidine fragment. Molecular modelling was used to predict binding modes of synthesized molecules and rationalize experimentally observed SAR. The leader compound is twice more effective in inhibiting the formation of germ tubes by Candida albicans yeast cells compared to voriconazole. An increased level of Pdr5, an azoles drug efflux pump was observed, but the increase is lower than that caused by azoles. The results can be useful for further development of more powerful and safe antifungal agents.

The roots and rhizomes of Rubia tinctorum L. have been widely used both for industrial and medicinal purposes for centuries. The primary biologically active substances from Rubia tinctorum L. roots and rhizomes are anthraquinone derivatives such as ruberythric acid and lucidin-3-primeveroside. Their identification and quantification are carried out by various analytical methods, requiring a complicated sample preparation as well as special reagents and reference samples. However, NMR spectroscopy has no limitations of this kind. In this work, we have developed and validated a new express and standard-free method for the qualitative and quantitative analysis of ruberythric acid and lucidin-3-primeveroside by 1H NMR spectroscopy in the extracts from the roots and rhizomes of Rubia tinctorum L. In this work, we have optimized the conditions of the sample preparation and registration of 1H NMR spectra, determined the optimal solvent and reference compound and confirmed the obtained results by HPLC-UV-MS.

Environmental monitoring and assessment of the prospects for extracting biologically active substances (BAS) from various types of plant biomass requires the development of simple and fast methods for measuring their content in raw materials. For this purposes massspectrometry and NMR spectroscopy are widely used. Both methods have their own advantages and disadvantages. But NMR spectroscopy is a nondestructive method and requires simple sample preparation. In addition, quantitative studies using NMR spectroscopy do not require authentic standard samples. We have developed various techniques for targeted metabolomic analysis of plant origin samples using NMR spectroscopy, including: determination of anthraquinone derivatives in extracts from roots and rhizomes of Rubia tinctorum L., determination of diosmin in Hyssopus officinalis L., determination glucofrangulin A in extracts from leaves of Rhamnus frangula L.

The new methodological approach of rapid evaluation of intracellular grape and wine water without sample preparation, based on the quantitative nuclear magnetic deuterium spectroscopy (2H(D)-qNMR) is suggested and developed under the research program carried out under the scientific grant of the International Organization of Vine and Wine (O.I.V.). The approach provides a quantitative high precision measurement of the deuterium content in water based on the direct dependence of the areas of NMR signals on the number of nuclei responsible for these signals. The developed approach uses similar to the well-known SNIF-NMR method with an internal reference substance (IRS) - dimethyl sulfoxide (DMSO). The IRS signals in the NMR spectrum do not overlap with the signals of main components of the analyte (e.g., grape must/juice, wine). In addition, it is possible to change the deuterium content using an available NMR solvent - DMSO-d6. At the same time, the amount of deuterium in the IRS-DMSO is increased by adding DMSO-d6 so that the proportion of the standard, equal to 10-15% by volume, gives a signal commensurate in its intensity with the signal of water contained in the analyte. The exact amount of deuterium in the IRS is determined by comparing the integral intensities of signals in the 2H(D)-NMR spectrum in a standard water sample (VSMOW) with a known deuterium content. After calibration of the deuterium content in IRS, the analyte and DMSO in quantities of 0.5 and 0.075 ml, respectively, are placed in a standard tube, then the 2H(D)-NMR spectrum is measured in the following conditions: 90° pulse, 2.5 sec acquisition time, 3 sec delay relaxation, 1000 scans. Additionally, to assess the amount of water in the analyte, the 1H-NMR spectrum is recorded, from which the contents of main sample components, for example, ethanol, glycerol, sugars, etc., are determined. The calculation of the deuterium content is carried out by quantifying the integral intensities of the IRS signals and the water contained in the sample. The developed methodological approach has been validated in experimental tests to study the natural content of deuterium in intracellular water of grapes of different seasons, as well as to study changes in the quantitative balance of deuterium in the case of adding extension water to musts before and after fermentation.

The papaya plant (Carica papaya L.) is tree-like fruit plant cultivated throughout the tropics and subtropics. The aim of this study was to compare the physicochemical properties, fatty acid, sterols, and triterpenic alcohols composition of Carica papaya L. seed oils grown in a typical geographical location and Carica papaya L. seed oils grown in an untypical geographical location in greenhouse conditions (Saratov Region, Russia). The oils were extracted from the seeds of Carica papaya L. fruits collected in Kenya, the Dominican Republic, Angola, Ghana, and Brazil, as well as from the seeds of fruit plants grown in a similar environment (Russian Federation, Saratov). Parameters such as the oil yield, refractive index, peroxide value, iodine value, saponification value, and acid value of the extracted Carica papaya L. seed oils were determined. The qualitative and quantitative chemical compositions of the seed oils were determined by a combination of mass spectrometry and NMR spectroscopy. The profiles as well as the content of fatty acids, sterols, triterpenic alcohols, and benzyl isothiocyanate were established. The saponifiable fraction of the oils is mainly represented by triglycerides (98.7–99.4%), while di-(0.4–1.1%) and monoglycerides (0.1–0.3%) are also present but in smaller amounts. The content of sterols and triterpene alcohols was (537.5–918.2) mg/100 g of oil (0.54–0.92%), and up to 75% of the fraction was represented by β-sitosterol (55.9–66.7%) and its saturated analogue-sitostanol (11.0–15.7%). The physicochemical properties and the fatty acid, sterol, and triterpenic alcohol composition of seed oils from Carica papaya L. fruits, cultivated in Russia, is in the quantitative range of other samples, which suggests that Carica papaya L. can be grown in Russia for obtaining the seed oil.

This review is devoted to consideration of physicochemical methods for detection of pharmaceutically active substances, in particular, phosphodiesterase-5 (PDE-5) inhibitors, present in dietary supplements. The necessity of using the most informative approaches for the identification of PDE-5 inhibitors registered as drugs and their structurally modified analogs with unknown safety and efficacy in the composition of dietary supplements is emphasized.

Abstract The objective of this study was to evaluate the chemical compounds present in the Carica papaya L. seed oil of different geographic origin in comparative aspect. The oils were extracted from the seeds of Carica papaya L. fruits collected in Kenya, the Dominican Republic, Angola, Ghana, Brazil, as well as from seeds of fruit plants grown in close environment (Russian Federation, Saratov). The seeds yielded 18.3–27.0% of oil. Parameters such as oil yield, refractive index, peroxide value, iodine value, saponification value and acid value of the extracted Carica papaya L. seed oils were determined. The qualitative and quantitative chemical composition of seed oils were determined by a combination of mass spectrometry and NMR spectroscopy. The profiles and the content of fatty acids, sterols, triterpenic alcohols and benzyl isothiocyanate were established. The saponifiable fraction of the oils is represented predominantly by triglycerides (98.7–99.4%), and di- (0.4–1.1%) and monoglycerides (0.1–0.3%) are also present in minor amounts. They contain mainly oleic (68.7–74.9%), palmitic (14.2–16.9%), stearic (4.8–5.9%) and linoleic (3.4–6.8%) acids. The content of sterols and triterpene alcohols was (537.5–918.2) mg/100 g of oil (0.54–0.92%), up to 75% of the fraction was represented by β-sitosterol (55.9–66.7%) and its saturated analogue – sitostanol (11.0-15.7%). The content of benzyl isothiocyanate in lipid complexes ranged from 0.03–0.06%. The chemical composition of seed oils of Carica papaya L. fruits, cultivated in different geographic regions, is very similar. Carica papaya L. is considered to be a promising source of valuable seed oil.

Dihydroquercetin (DHQ) is a bioflavonoid with high antioxidant, capillary-protective, and anti-inflammatory activity. DHQ has previously been used for treating Middle East respiratory syndrome coronavirus (MERS-CoV) infection and is currently considered a potential regulator of oxidative stress as part of COVID-19 multipurpose therapy. DHQ has a high safety profile but low bioavailability that limits its use. Innovative techniques (liposomization, crystal engineering, etc.) can be used to increase its bioavailability.

В обзоре рассмотрены физико-химические методы выявления фармацевтически активных субстанций, в частности ингибиторов фосфодиэстеразы-5 (ФДЭ-5), в биологически активных добавках к пище. Показана необходимость использования наиболее информативных подходов для выявления зарегистрированных в качестве лекарственных средств ингибиторов ФДЭ-5, а также их структурно модифицированных аналогов с неустановленной безопасностью и эффективностью в составе БАД к пище.

The article discusses a unified analytical algorithm for identification of component composition of winemaking products, established in the new national standard GOST R 59570-2021 «Winemaking products. Identification of component in terms of determination of the origin of ethanol and other compounds of physical-chemical composition». The standard provides modern scientific data on winemaking products, as well as data on natural, agrotechnical and technological factors that can impact the component composition of products to interpret the results of analytical evaluations. The article provides practical examples of use of analytical methods established in the standard for the study of winemaking products produced in Russia, Kazakhstan, Armenia and foreign countries.

Авторы были добавлены в раздел «Вклад авторов». Вместо: Г. Бакореза, Р. А. Абрамович, Н. Н. Бойко, С. Лазар разработали схему выделения липофильных и гидрофильных компонентов семян N. sativa L. Д. И. Писарев, О. О. Новиков, А. В. Хромов и О. Г. Потанина провели аналитическое исследование выделенных фракций семян N. sativa L., обработку данных и интерпретацию результатов. Все авторы принимали участие в обсуждении результатов и написании текста статьи. Исправлено на: Г. Бакореза, Р. А. Абрамович, Н. Н. Бойко, С. Лазар разработали схему выделения липофильных и гидрофильных компонентов семян N. sativa L. С. В. Горяинов, В. А. Ивлев, С. Эспарса, Д. И. Писарев, О. О. Новиков, А. В. Хромов и О. Г. Потанина провели аналитическое исследование выделенных фракций семян N. sativa L., обработку данных и интерпретацию результатов. Все авторы принимали участие в обсуждении результатов и написании текста статьи.

Дигидрокверцетин (ДГК) — биофлавоноид, обладающий высокой антиоксидантной, капилляропротекторной и противовоспалительной активностью. Ранее ДГК применялся при инфекции, вызванной коронавирусом ближневосточного респираторного синдрома (MERS-CoV). В настоящее время ДГК рассматривается в качестве потенциального регулятора окислительного стресса в составе комплексной терапии COVID-19. ДГК характеризуется высоким профилем безопасности, но низкой биодоступностью, ограничива-ющей его применение. Для повышения биодоступности ДГК могут быть использованы инновационные технологии (липосомирование, инженерия кристаллов и др.).

Introduction. Seeds of Nigella sativa L. are widely known as a source of fatty oil with a very rare component-thymoquinone. The therapeutic potential of biologically active compounds of plant seeds covers a positive effect on the gastrointestinal tract, cardiovascular and immune systems. In addition, hypoglycemic, antioxidant, antitumor, oncoprotective, immunomodulating effects were found in thymoquinone. In addition to fatty oil and thymoquinone, a number of other significant compounds are present in the seeds, which also make up their own pharmacological asset. Aim. Study was to develop a processing flow chart and analyze the lipophilic and hydrophilic components of the seeds of N. sativa L.Materials and methods. The following methods were used as analytical methods: gas-liquid chromatography with a flame ionization detector - for the analysis of sterols and triterpenes; chromatography-mass spectrometry (gas-liquid chromatography with mass spectrometric detection) - for the study of essential oil; chromatography-mass spectrometry (high performance liquid chromatography with mass spectrometric detection) - to study flavonoids. To obtain individual fractions of biologically active compounds of seeds of N. sativa L., fractional extraction was used.Results and discussion. The principle of this approach in this case is to extract the entire lipid complex of seeds with n-hexane, followed by removal of the extractant. The thickened hexane extract is treated with ethyl alcohol, which extracts unsaponifiable compounds - terpenes, quinones, sterols and does not dissolve triacylglycerides. The seed meal remaining after hexane extraction is treated with ethyl alcohol 70 %, into which hydrophilic molecules, in particular flavonoids, pass.Conclusion. After transesterification, 5 compounds were identified in the lipophilic fraction of saponifiable lipids, the linoleic and oleic acids being dominant. A characteristic feature of this fraction is the presence of cis-11,14-eicosadiene acid, which can act as a marker element of the fatty oil of the seeds of N. sativa L. Sterols and triterpenes were found in the unsaponifiable fraction. The major component of this fraction is β-sitosterol. In addition to the indicated sterol, campesterol and stigmasteri are present. Triterpenes are represented by cycloartenol and its derivatives. Simple phenols, quinones and monoterpenes were found in the essential oil complex, p-cymol, thymoquinone and α-thuyen predominate. The hydrophilic fraction of the seeds of N. sativa L. includes flavonoids of the methoxylated series of flavones and kempferol glycosides.

A comprehensive study of urea greases obtained on the basis of Group I distillate oils, which have a viscosity in the range from 24.4 to 342.0 mm2/s at 40°C, has been carried out. The results obtained have made it possible to reveal the dependence of various physicochemical parameters of greases (dropping point, ultimate strength, colloidal stability, wear rate) on the viscosity of the base oil and the structure of diurea used as a thickener. The revealed relations allow prediction of the properties of greases at the stage of selecting the initial components.

Environmental monitoring and assessment of the prospects for extracting biologically active substances (BAS) from various types of plant biomass requires the development of simple and fast methods for measuring their content in raw materials. A new approach for measuring the content of various flavonoids groups in plant raw material using 1H NMR spectroscopy has been developed, which allows to characterize its resource capabilities and study the effects on their composition different environmental factors without complex sample preparation and standard samples.

An analysis of some popular antibiotics was carried out by quantitative 1H NMR spectroscopy and DART mass spectrometry without the use of reference standards.