Bibenzyls are now recognized as compounds for use in cancer therapy, and many molecules from the bibenzyl group have shown promising anticancer activity; therefore, the characterization of new bibenzyls with strong biological activity is important for developing new anticancer drugs. In this study, we compared the effects of three bibenzyls (3,3′-dihydroxy-4,5-dimethoxybibenzyl, 3,5-dihydroxy-4-methoxybibenzyl and 3,5,3′-trihydroxy-4-methoxybibenzyl) isolated from Empetrum nigrum and erianin on platelets and the MOLT-3 T-lymphoblast cell line. Among the studied bibenzyls, 3,3′-dihydroxy-4,5-dimethoxybibenzyl significantly reduced the viability of MOLT-3 cells and platelets and induced strong phosphatidylserine (PS) surface exposure. We showed that 3,3′-dihydroxy-4,5-dimethoxybibenzyl induced the death of MOLT-3 cells and platelets, which was not mediated by apoptosis, pyroptosis, necroptosis, autophagy, or calpain-dependent pathways, and that the p38 MAP kinase pathways are at least partly involved in the activity of 3,3′-dihydroxy-4,5-dimethoxybibenzyl. In conclusion, our data show that 3,3′-dihydroxy-4,5-dimethoxybibenzyl could be a promising candidate for future analysis as an anticancer drug.

Characteristics of cell growth and the composition of polyphenolic compounds in callus cultures of Lavandula angustifolia Mill. grown on various nutrient media were determined. The addition of phytohormones to the nutrient medium is a productive biotechnological approach to regulation of secondary metabolite synthesis. The presence of α-naphthylacetic acid (NAA), 2,4-dichlorophenoxyacetic acid (2,4-D), 6-benzylaminopurine (BAP), and kinetin in growth media was found to facilitate the accumulation of phenolic compounds (phenolic acids, flavonoids, and anthocyanins) in many cases. For each nutrient medium, growth curves were plotted and growth parameters were calculated. Analysis by means of the reverse phase HPLC combined with UV spectrophotometric detection revealed that rosmarinic acid is a major compound in all samples of lavender callus cultures. The patterns of rosmarinic acid accumulation were determined as a function of light availability and the composition of the nutrient medium. Among the four media examined, the medium containing 2.0 mg/L α-NAA and 0.1 mg/L BAP ensured the highest values of growth parameters and rosmarinic acid content (1.26 ± 0.13

Introduction. One of the key tasks of the pharmaceutical industry is the search for new promising compounds – potential drug candidates. Natural objects, especially plants, have long been rich sources of new molecules and are widely used in the global food and pharmaceutical industries. Cloudberry (Rubus chamaemorus L.) is a perennial herb from the Rosaceae family. The fruits and leaves of R. chamaemorus contain a wide variety of polyphenolic secondary metabolites – hydrolysable/condensed tannins and flavonoids. Extracts enriched by polyphenols showed significant antiproliferative activity and inhibition of cell growth, and also induce cell apoptosis. As a result of our previous phytochemical research of R. chamaemorus leaves, five polyphenolic secondary metabolites belonging to the classes of tannins and flavonoids were isolated and characterized.Aim. Screening of previously isolated from R. chamaemorus individual compounds for the hemostasis system in vitro and identification of the most promising compounds for subsequent pharmaceutical development.Materials and methods. Experiments under in vitro conditions were performed on the blood of healthy male donors. The research of the effect on platelet aggregation was carried out according to the Born method on an AT-02 aggregometer (LLC "SPF "Medtech", Russia). Determination of anticoagulant activity was carried out by conventional clotting tests on a Solar CGL 2110 turbidimetric hemocoagulometer (CJSC "SOLAR", Russia). Cytofluorimetric analysis was performed on a NovoCyte instrument (Agilent Technologies, USA).Result and discussion. The influence of the isolated compounds 1–5 on the parameters of activation, platelet aggregation and the coagulation component of hemostasis was studied. At a concentration of 1.0 mg/ml, compounds 1–5 did not affect the fibrinogen concentration and prothrombin time. Compounds 1, 3 and 5 completely suppressed platelet activation at the studied concentrations. Compounds 1 and 3 showed antiaggregation activity comparible to the values of acetylsalicylic acid and are contained in all aqueous and alcoholic extracts of R. сhamaemorus leaves; their quantitative content varies depending on the extraction conditions.Conclusion. Thus, as a result of the screening of individual compounds 1–5 isolated from the leaves of R. chamaemorus their antiaggregating and anticoagulation properties were established. Compounds 1 (4-O-α-L-arabinofuranosylellagic acid) and 3 (quercetin-3-O-β-D-glucuronide) showed antiaggregation activity comparible to that of acetylsalicylic acid, and are the most promising of the studied series of compounds for the subsequent pharmaceutical development of new antiplatelet agents.

In this study, we expanded our previous work by testing compounds 1-12 for their ability to inhibit platelet activation at low (30 mu M) concentration by inhibition of ROS production, thromboxane synthase (TxS) activity, and activation of cyclic nucleotide pathways. We also investigated whether some of these compounds could potentiate the effects of P2Y12 ADP receptor inhibitor action and discussed possible structure-activity relationships of the tested compounds. We showed that at this concentration only compounds 7 and 12 significantly inhibited thrombin-induced platelet activation which was accompanied by inhibition of ROS production and thromboxane synthase activity. Correspondingly, these compounds significantly potentiated the inhibitory effect of cangrelor on thrombin-induced platelet activation. In some other cases, inhibition of ROS production and thromboxane synthase activity did not correlate with platelet inhibition, indicating that these compounds could affect some, still unidentified, activatory pathways in platelets that counteract their inhibitory effects. {Graphical Abstract}

Valeriana officinalis L. is a widely spread representative of the Eurasian flora. Preparations based on valerian extracts are recognized as sedatives, antidepressants and anxiolytics by both traditional and modern medicine. Despite the extremely high interest in the biological and pharmacological properties of valerian extracts, the composition of biologically active substances and specific activities of their components are still not completely studied. Therefore, here we address the metabolic profiles of the valerian plants with a special emphasis on their major root constituents with pronounced neuroprotective activity. The following phytochemical analysis of the V. officinalis L. roots led to isolation of nine compounds, including two previously undescribed iridoids – isovaltrate isovaleroyloxyisohydrin (1) and isovaltrate α-(isovaleroxy)isovaleroxyhydrin (2) together with one previously undescribed valerenic acid derivative – 2-oxovalerenic acid (3). Three previously described iridoids – iridoidvol A (4), isovaltrate isovaleroyloxyhydrin (5) and valtrate hydrine B1 (6), along with valerenic acid (7) and its metabolites - hydroxyvalerenic (8) and acetoxyvalerenic acids (9) were isolated. Functional assays accomplished with the isolated compounds revealed moderate antioxidant activity characteristic for all of them. Moreover, high neuroprotective potential was observed for the compound 3 (and to less extent of 8). This potential was manifested by a pronounced antineurodegenerative effect in the model of Aβ25-35 induced cytotoxicity. In respect of thrombin-induced platelet aggregation, compounds 1, 4 and 7 demonstrated pronounced inducing and compounds 2, 5 and 6 showed clear potentiating activity. Valerenic acid showed activity on TRPV1 ion channels, manifested by both channel activation and potentiation of the capsaicin response in CHO cells expressing TRPV1. Moderate antioxidant activity was characteristic of all compounds.

Chemical investigation of the hydnoid fungus Sarcodontia setosa resulted in the isolation of five compounds, including two new sarcodontic acid derivatives - setosic acid (1) and 7,8-dehydrohomosarcodontic acid (2) along with three known benzoquinone pigments - sarcodontic acid (3), 4,5-dehydrosarcodontic acid (4) and dihydrosarcodontic acid (5). The structures were elucidated using spectroscopic methods (UV, NMR and HR-ESIMS). The biosynthetic relationship of the isolated compounds is proposed and discussed. Antibacterial activity screening of compounds 1-5 against ESKAPE bacterial strains in vitro with zones of inhibition was performed and MIC values were established for the most active compounds (3 and 5).

Flavonoid aglycones are secondary plant metabolites that exhibit a broad spectrum of pharmacological activities, including anti-inflammatory, antioxidant, anticancer, and antiplatelet effects. However, the precise molecular mechanisms underlying their inhibitory effect on platelet activation remain poorly understood. In this study, we applied flow cytometry to analyze the effects of six flavonoid aglycones (luteolin, myricetin, quercetin, eriodictyol, kaempferol, and apigenin) on platelet activation, phosphatidylserine externalization, formation of reactive oxygen species, and intracellular esterase activity. We found that these compounds significantly inhibit thrombin-induced platelet activation and decrease formation of reactive oxygen species in activated platelets. The tested aglycones did not affect platelet viability, apoptosis induction, or procoagulant platelet formation. Notably, luteolin, myricetin, quercetin, and apigenin increased thrombin-induced thromboxane synthase activity, which was analyzed by a spectrofluorimetric method. Our results obtained from Western blot analysis and liquid chromatography–tandem mass spectrometry demonstrated that the antiplatelet properties of the studied phytochemicals are mediated by activation of cyclic nucleotide-dependent signaling pathways. Specifically, we established by using Förster resonance energy transfer that the molecular mechanisms are, at least partly, associated with the inhibition of phosphodiesterases 2 and/or 5. These findings underscore the therapeutic potential of flavonoid aglycones for clinical application as antiplatelet agents.

Fourteen hexane-soluble polyphenolic secondary metabolites were previously isolated as individual compounds from Empetrum nigrum L. and identified as three bibenzyls, four 9,10-dihydrophenanthrenes, two chalcones, four dihydrochalcones and one flavanone. In this study, the mass-spectra and retention indexes (RI) of compounds 1-14 without prior derivatization were obtained and the resulting fragmentation pathways rationalized in accordance with literary data and the compounds structures. Preliminary differences in metabolite composition were assessed by comparative profiling using GC-MS chromatography combined with multivariate data analysis for a limited amount of E. nigrum n-hexane extracts obtained from plants growing in three different geographic locations. To characterize antioxidant capacity of isolated compounds 1-14 we used our well-established model based on reactive oxygen species (ROS) production by activated human platelets and showed that most of the examined polyphenols act as antioxidants by inhibition of ROS production.

Pharmacopoeias are important resources for the quality control of medicinal plants and their products. Considering that approximately 80% of the world population to different extents relies on medicinal plants for the prevention and treatment of medical ailments the safety and suitability of medicinal plants is extremely important. Unfortunately, for many medicinal plants the active component or group of components responsible for their pharmacological activity are unknown. In such cases, the standardization of the medicinal plant material is performed using reference compounds that are either contained in the plant, but are known to not mediate the plants biological activity or are not contained in the plant at all, but find use as auxiliary reagents, for example, to help identify the necessary chromatographic zones/peaks. Additionally, many medicinal plants do not have qualitative or quantitative analysis procedures in place or use methods with low selectivity (spectrophotometry, colour reactions). In these cases, it is impossible to confidently and adequately standardize the medicinal plant material. Two other issues that complicate medicinal plant standardization include the variability of its chemical composition depending on multiple biotic and abiotic factors and the lack of sufficient data on the chemical composition of some plants. In this review, we analyzed medicinal plants common to the Eurasian Economic Union (EAEU), European, United State and Japanese Pharmacopoeias. We have analysed and systematized literature data devoted to the relation between the chemical composition and pharmacological activity of the plants presented in this review. Based on the analysed data, we have suggested more rational and adequate methods for the quality assessment and quantitative standardization of medicinal plants.

Ethnopharmacological relevance: Ziziphora clinopodioides subsp. bungeana (Juz.) Rech.f. is a subshrub that is widely distributed in China, Kazakhstan, Kyrgyzstan, Mongolia, Russia, Tajikistan, Turkmenistan, and Uzbekistan. The species is used in traditional medicine for the relief of symptoms connected to cardiovascular diseases like coronary heart disease or hypertension. Aim of the study: was to validate traditional use of Z. clinopodioides subsp. bungeana for the treatment of coronary hearth diseases using in vivo models and to find active compounds responsible for the activity. Materials and methods: Multiple extracts were obtained from the aerial parts of Z. clinopodioides subsp. bungeana using maceration, liquid-liquid extraction, CO2 extraction and ultrasound-assisted extraction. Preliminary screening studies for the evaluation of the efficacy of Z. clinopodioides subsp. bungeana extracts on the model of hemic hypoxia were performed. The most effective samples were selected and included in the main study. Stage 2 of the study evaluated the cardiotropic activity of the selected extracts on a model of chronic heart failure. Preparations were administered to animals intragastrically once a day for 28 days. For the isolation of individual compounds plant material was extracted with 96% ethanol. The obtained crude extract was sequentially extracted with n-hexane and dichloromethane and separated by chromatography on a Diaion HP-20 column. The obtained fractions were further subjected to Sephadex LH-20 column chromatography and eluted isocratically with 96% ethanol (EtOH) to yield subfractions, which were further separated by preparative HPLC to obtain 13 individual compounds. Results: Extracts obtained from Ziziphora clinopodioides subsp. bungeana (Juz.) Rech.f. herb were subjected to pharmacological screening for the evaluation of their efficacy on hemic hypoxia. Based on the obtained results, out of the sixteen tested extracts two (AR and US 60%) were selected for further evaluation of their cardiotropic activity. Modeling of chronic heart failure was carried out in accordance with the following stages: 1) anesthesia with chloral hydrate at a dose of 450 mg/kg, intraperitoneally, 2) artificial ventilation of the lungs, 3) thora-cotomy, 4) modeling of permanent ischemic or ischemic-reperfusion damage. Both extracts effected the in-dicators of contraction and output, comparable to the reference drug -Monopril. Based on the extraction methods used to obtain RAF and US60 and data from the literature, it can be assumed that they contain com-pounds with medium polarity, including polyphenols and terpenoids. At the next stage three previously unde-scribed monoterpenoid derivatives - Ziziphoric acid (1), Ziziphoroside D (2) and 6 & PRIME;-malonylziziphoroside A (3), along with two previously described megastigmane glucosides - blumenol C glucoside (4), blumenol C 9-O-(6 & PRIME;-O-malonyl-beta-D-glucopyranoside (5) and two previously described monoterpenoids 7a-hydroxymintlactone (6), 7-hydroxypiperitone (7) together with six polyphenols - pinocembrine-7-O-rutinoside (8), chrysine-7-O-rutinoside (9), acacetin-7-O-rutinoside (10), luteolin-7-O-rutinoside (11), rutin (12) and rosmarinic acid (13) were isolated from Z. clinopodioides subsp. bungeana extracts. Conclusion: Our results support the traditional use of Z. clinopodioides subsp. bungeana for the treatment of coronary diseases. As a result of Z. clinopodioides subsp. bungeana extracts screening in vivo, two extracts were selected as potential cardiotropic agents. Phytochemical analysis of the plant material led to the isolation of five terpenoid derivatives, two megastigmane glycosides, five flavonoids and one cinnamic acid derivative, which could be responsible for the reported biological activity. Future experiments are required to understand the mechanisms of action for the isolated compounds.

Introduction. Thymoquinone (2-Isopropyl-5-methyl-1,4-benzoquinone) is an organic compound of plant origin, which is formed as a result of the oxidation of thymohydroquinone. Thymoquinone is a component of the essential oil of black caraway seeds ( Nigella sativa L.) and is known to possess a significant spectrum of pharmacological activity. Due to the lipophilicity of thymoquinone and its ability to accumulate in oils, we proposed a method to isolate thymoquinone from the fatty oil of caraway seeds in order to assess its selective accumulation and the possibility of using the oil as a source for the compounds production. Aim. Method development for the isolation of thymoquinone as an individual compounds from black caraway ( Nigella sativa L.) seed oil, to confirm its structure and determine the degree of purity of the obtained substance. Materials and methods. To confirm the authenticity of the raw materials, analysis of key morphological and anatomical diagnostic features was performed. Quantitative assessment of thymoquinone content in black caraway seeds and control of the isolation process were performed though HPLC analysis. Sample preparation was carried out with methanol by: 1) triple extraction on a boiling water bath; 2) sonification; 3) maceration. The structure of the isolated compound was confirmed through the analysis spectral characteristics using IR spectroscopy by comparing the obtained IR spectrum with the data from the NIST database and one-dimensional NMR spectroscopy. Results and discussion. As a result of the morphological and anatomical analysis, the authenticity of N. sativa seeds was confirmed. Extracts from black caraway seeds obtained by various sample preparation methods were analyzed with HPLC. As a result, it was noted that the method of obtaining the extract does not significantly affect the yield of thymoquinone, the content of which in black caraway seeds is 0.25 ± 0.02 %, which is sufficient for isolation purposes. Through the evaluation of various isolation methods for thymoquinone from black caraway seeds – maceration with alcohol and n-hexane from crushed seeds, liquid-liquid extraction from fatty oil, steam distillation of oil – showed that the best way to obtain thymoquinone is through the distillation of black caraway seed oil with water steam [oil : water ratio (1 : 1)] in a sand bath for 3 hours. The yield of thymoquinone from N. sativa oil is 398 mg from 150 ml of oil (0.26 %). The structure of thymoquinone was confirmed by spectral characteristics in comparison with the NIST database and literature data. Conclusion. The possibility of isolating thymoquinone from Nigella sativa L. seed fatty oil with a chromatographic purity (HPLC) of more than 97 % along with the comparison of the isolated compounds spectral characteristics with literature data, which confirm the identity of the obtained compound, was shown. The proposed express and efficient method for the isolation of thymoquinone through steam distillation provides a yield of the target component of 0.26 %. This method can be applied at roduction sites that harvestand process of black caraway seeds to obtain natural thymoquinone.

Precise adaptation of the greenhouse lighting spectrum to basic photophysiological processes can effectively and directionally stimulate plant growth and development. The optimal spectrum depends on the plant species and the stage of development and could be assessed empirically. The aim of this study is to determine the LED illumination spectrum that provides a significant improvement in the growth rate and accumulation of biologically active compounds for basil plants (Ocimum basilicum L.) under hydroponic cultivation compared to more traditional lighting sources. The following light sources with various emission spectra were used: an LED lamp within a spectral range of 400–800 nm (B:G:R 15%:5%:80%); a high-pressure sodium lamp (HPS) (B:G:R 5%:45%:50%); a compact fluorescent lamp (B:G:R 20%:40%:40%); a grow LED strip (B:G:R 15%:40%:45%); a white LED lamp (B:G:R 30%:45%:25%); a customized LED lighting setup in color ratios 100%B, 75%B + 25%R, 50%B + 50%R, 25%B + 75%R, 100%R, and natural lighting. A photosynthetic photon flux density (PPFD) of 150 μmol∙m−2∙s−1 was provided with all the sources. It was demonstrated reliably that employing the LED strip as an illumination device gives a 112% increase in basil plant yield compared to the HPS; the transpiration coefficient for the LED strip is six times lower than for the HPS. The content of flavonoids in the basil aerial parts on the 30th, 50th, and 70th days of development is 3.2 times higher than for the HPS; the metabolite composition is also more uniform for LED strip lighting.

Two previously undescribed isoquinoline alkaloids, bracteatinine (1) and isogroenlandicine (2), together with four known alkaloids - coptisine (3), dehydrocorydaline (4), palmatine (5) and jatrorrhizine (6) were isolated from the aerial parts of Corydalis bracteata (Steph. Ex. Willd.) Pers. The structures of the compounds were elucidated using 1D and 2D NMR data along with HRESI-MS. The isolated new compounds bracteatinine and isogroenlandicine are close structural derivatives and isomers of corgoine and groenlandicine, respectively. Bracteatinine is also notable, being a representative of the rare 2-benzylisoquinoline alkaloids. Many natural products isolated from different plants are used as adjuvants, in addition to standard chemotherapy, in treatment of different cancers. Cancer-associated thrombosis remains a common complication and leading cause of mortality for cancer patients. Because platelets play the key role in thrombotic complications, we investigated effects of the isolated alkaloids 1-6 on platelet reactivity and showed that they did not significantly affect platelet function.

Introduction. The emergence of new strains of microorganisms that are multidrug resistant (MDR) in relation to the antimicrobial drugs used is one of the pressing problems of modern medicine. To prevent an increase in MDR-related deaths, the search for new antibiotics and their introduction into medical practice must be continuously ongoing. Infectious diseases are also accompanied by cell damage and the development of free radical oxidation processes, therefore the search for new antioxidants is also an important task. Considering the powerful biosynthetic potential of basidiomycetes, this group of fungi has every prospect of becoming a new source of biologically active substances in general, as well as antibiotics and antioxidants in particular. Cap mushrooms, represented mainly by basidiomycetes, number about 14,000 species and are an accessible source of raw materials for the search for promising antimicrobial compounds and antioxidants. Aim. Study of the antioxidant and antimicrobial activity of total extracts obtained from cap mushrooms against Escherichia coli , Staphylococcus aureus and Candida albicans and assessment of the suitability of cap mushrooms as a natural source of substances with antimicrobial and antioxidant activity. Materials and methods. The antifungal and antibacterial activity of the extracts was determined by the micromethod of two-fold serial dilutions in a liquid nutrient medium in 96-well plates in duplicate. The study of this type of biological activity was carried out against reference (type) strains Staphylococcus aureus ATCC 6538-P, Escherichia coli ATCC 25922, Candida albicans NCTC 885-653. To study antioxidant activity using DPPH, we used alcoholic extracts from the fruiting bodies of mushrooms obtained by maceration with 96 % ethanol at a ratio of raw materials to extractant of 1 to 8 for 24 hours, an aqueous solution of ascorbic acid (vitamin C) and an ethanol solution of Trolox. Result and discussion. In relation to S. aureus , a representative of gram-positive flora, the studied extracts of cap mushrooms showed low activity, on average about 2500 or 5000 μg/ml. In relation to E. coli , a representative of gram-negative flora, 8 % of the studied cap mushroom extracts showed an average activity of about 1250 μg/ml. The largest number of cap mushroom extracts – 19% of all studied species – showed activity against the yeast micromycete C. albicans . The highest activity against C. albicans was observed in extracts of the mushrooms Cantharellula umbonata with an MIC of 625 μg/ml, Cortinarius olivaceofuscus with an MIC of 625 μg/ml, and Hypomyces chrysospermus with an MIC of 312 μg/ml. During screening of antioxidant activity, the studied extracts were divided into three groups: with high (more than 50 % PPR), medium (from 15 to 50 % PPR) and low (less than 15 %) antioxidant activity. It was shown that the sum of phenolic compounds significantly correlates with the level of antioxidant activity in all three groups, but in the groups with medium and low antioxidant activity there are also other non-phenolic groups of compounds that make a significant contribution to the total antioxidant activity. Conclusion. Cap mushrooms are a promising source of biologically active substances with antifungal and antioxidant activity.

Chemical investigation of the polypore fungus Fistulina hepatica resulted in the isolation of five compounds, including four new polyacetylenic fatty acid derivatives - isocinnatriacetin B (1), isocinnatriacetin A (2), cinna-triacetin C (3) and ethylcinnatriacetin A (4) together with one known polyacetylene fatty acid derivative - cinnatriacetin A (5). The structures were elucidated using spectroscopic methods (UV, NMR, HR-ESIMS) along with comparison to literature data. Antibacterial activity screening of compounds 1-5 against ESKAPE bacterial strains in vitro with zones of inhibition (ZOI) was performed and MIC values were established for the most active compounds (3 and 4). Together with that morphological and growth parameters under solid-phase cultivation were also researched.

Introduction. The genus Impatiens L. includes about 850 species, which are found mainly in tropical and subtropical climate zones. The Indigenous people of Pakistan used pastes and extracts from I. glandulifera for the treatment of joint pain, anxiety and skin allergies [6]. Flowers of I. glandulifera are used in Bach flower remedies, which are used for sedation, relaxation and helping to balance emotional states. Aim. Isolation and structural elucidation of 11 phenolic constituents from the aerial parts of I. glandulifera and the evaluation of their antioxidant activity. Materials and methods. The aerial part of Impatiens glandulifera Royle was collected in the Leningrad region near the village of Orekhovo in 2021. Fractions were analyzed by analytical high performance liquid chromatography (HPLC) using a Prominence LC-20 (Shimadzu, Japan) equipped with a diode array detector. The isolation of individual compounds was carried out by column chromatography on open glass columns with sorbents of different selectivity, as well as by preparative HPLC using a Smartlina (Knauer, Germany) equipped with a spectrophotometric detector. The structure of isolated individual compounds was established by 1D and 2D NMR spectroscopy (Bruker Avance III 400 MHz, Germany). To study the antioxidant activity, we used solutions obtained by dissolving the isolated substances in a mixture of dimethyl sulfoxide and ethanol; an aqueous solution of vitamin C and an alcoholic solution of Trolox (Sigma-Aldrich, Japan). Result and discussion. Phytochemical analysis of the aerial parts of Impatiens glandulifera Royle. resulted in the isolation of 11 polyphenolic secondary metabolites ( 1-11 ) and their structures were elucidated. The antioxidant activity of all isolated compounds was evaluated. Conclusion. The maximum RAP values of eriodyctiol ( 3 ), kaempferol ( 1 ), and quercetin ( 2 ) did not differ significantly ( p = 0.585) from those of the comparator preparations: vitamin C and Trolox, which indicates that the antioxidant effect of these three isolated compounds is comparable to the well-known antioxidants. However, the semi-effective concentrations of these substances are two or more times lower ( p = 2.56 · 10 –4 ) comparted with vitamin C.

Plants of the Corydalis (Papaveraceae) genus are widely used in oriental medicine and are known for their particularly rich content of biologically active substances. One of the species encountered in Russia, the large-flowered corydalis (Corydalis bracteata (Steph. ex Willd.) Pers.), is widespread in Western and Eastern Siberia, but none the less its chemical composition has not been properly studied yet.The aim of the study was to perform phytochemical analysis of Corydalis bracteata herb through isolation of the main secondary metabolites and elucidation of their structure, using modern chromatographic methods of analysis and NMR spectroscopy.Materials and methods: the analysis was performed for dried aerial parts of C. bracteata. The isolation of individual compounds was performed using open-column chromatography and glass columns packed with sorbents with different selectivity characteristics— Dianion® HP-20 (Supelco) and Sephadex® LH-20 (GE Healthcare)—as well as preparative-scale chromatography with a Kromasil® C18 column and detection at 235 nm. Water and acetonitrile mixed in the ratios 5:95–50:50 v/v with the addition of 0.1% trifluoroacetic acid were used as the eluents. The analysis of fractions before pooling was performed by high-performance thin-layer chromatography with Silica gel 60 F254 plates (Merck). The analysis of the individual compound solutions was performed by HPLC using a Prominence LC-20 (Shimadzu) instrument, a SUPELCOSIL™ LC-18 column, and detection at 235 nm. The structures of the isolated individual compounds were elucidated by one- and two-dimensional NMR spectroscopy using a Bruker Avance III 400 MHz NMR spectrometer.Results: four individual compounds from the С. bracteata aerial parts were isolated and analysed: an isoquinoline alkaloid— coptisine (1) and three flavonoids—rutin (2), quercetin-3-O-β-D-glucopyranoside (3), and kaempferol-3-O-β-D-glucopyranoside (4).Conclusions: as a result of the phytochemical analysis of the С. bracteata aerial parts, compounds of both alkaloid and flavonoid nature were isolated for the first time, and their structures were elucidated using NMR spectroscopy. С. bracteata should be considered as a promising potential source of biologically active substances.

Water avens (Geum rivale L.) is a common Rosaceae plant widely spread in Europe and North America. It is rich in biologically active natural products, some of which are promising as prospective pharmaceuticals. The extracts of water avens are well known for their triterpenoid metabolites and associated anti-inflammatory, antimicrobial and antioxidant activities. However, the polyphenolic profiles of G. rivale L. are still awaiting complete characterization. Accordingly, the contribution of its individual components to the antioxidant, antibacterial and neuroprotective activity of the extracts is still unknown. As this plant can be available on an industrial scale, a better knowledge of its properly-relevant constituents might give access to new highly-efficient pharmaceutical substances and functional products. Therefore, herein we comprehensively characterize the secondary metabolome of G. rivale by ESI-HR-MS, ESI-HR-MSn and NMR spectroscopy with a special emphasis on the polyphenolic composition of its aerial parts. Furthermore, a multilateral evaluation of the antioxidant, neuroprotective and antibacterial properties of the aqueous and ethyl acetate fractions of the total aqueous alcoholic extract as well as individual isolated polyphenols was accomplished. Altogether four phenolic acid derivatives (trigalloyl hexose, caffeoyl-hexoside malate, ellagic acid and ellagic acid pentoside), six flavonoids (three quercetin derivatives, kaempferol and three its derivatives and two isorhamnetin derivatives) and four tannins (HHDP-hexoside, proantocyanidin dimer, pedunculagin I and galloyl-bis-HHDP-hexose) were identified in this plant for the first time. The obtained aqueous and ethyl acetate fractions of the total extract as well as the isolated individual compounds showed pronounced antioxidant activity. In addition, a pronounced antibacterial activity against several strains was proved for the studied fractions (for ethyl acetate fraction the highest activity against E. coli АТСС 25922 and S. aureus strains ATCC 27853 and SG-511 (MIC 15.6 μg/mL) was observed; for aqueous fraction-against Staphylococcus aureus SG-511 (MIC 31.2 μg/mL)). However, the anti-neurodegenerative (neuroprotective) properties could not be found with the employed methods. However, the antibacterial activity of the fractions could not be associated with any of the isolated individual major phenolics (excepting 3-O-methylellagic acid). Thus, the aerial parts of water avens represent a promising source of polyphenolic compounds with antioxidant activity and therefrom derived human health benefits, although the single constituents isolated so far lack a dominant selectively bioactive constituent in the bioassays performed.

Two undescribed (1-2) and five known cyclic diarylheptanoids (3-7) were isolated from the false heartwood of white birch (Betula pubescens Ehrh.). All structures were elucidated through extensive 1D and 2D NMR experiments and HR-ESI-MS data, along with comparison of their spectroscopic data with those reported in the literature. The two new cyclic diarylheptanoids are betuladiol (1) and betulondiol (2). Extracts from false heartwood were evaluated for their antimicrobial activity against Klebsiella pneumoniae, Escherichia coli, Proteus mirabilis, Staphylococcus aureus and Cutibacterium acnes together with their antifungal activity against Candida albicans and Candida glabrata.

A new dihydrochalcone, 2',4'-dimethoxydihydrochalcone (1), together with 7 known compounds, 2',4'-dihydroxydihydrochalcone (2), 2'-hydroxy-4'-methoxydihydrochalcone (3), 2'-hydroxy-4'-methoxychalcone (4), 1-(3,5-dihydroxy-4-methoxyphenyl)-2-(3-hydroxyphenyl) ethane (5), 2,3,4,7-tetramethoxy-9,10-dihydrophenanthrene (6), 5-hydroxy-2,3,4-trimethoxy-9,10-dihydrophenanthrene (7) and 5,7-dihydroxy-6,8-dimethyl flavanone (8) were isolated from the shoots of Empetrum nigrum L. The structures of these compounds were elucidated using 1D and 2D NMR experiments along with HR-ESI-MS. Compound 6 is reported for the genus Empetrum for the first time.