Hogweed Seed Oil: Physico-Chemical Characterization, LC-MS Profile, and Neuroprotective Activity of Heracleum dissectum Nanosuspension.

The seeds of dissected hogweed (Heracleum dissectum Ledeb., Apiaceae) are the source of hogweed oil (HSO), which is still underexplored and requires careful chemical and biological studies. The performed physico-chemical analysis of HSO elucidated basic physical characteristics and revealed the presence of fatty acids, essential oil components, pigments, and coumarins. High-performance liquid chromatography with photodiode array detection and electrospray ionization triple quadrupole mass spectrometric detection (HPLC-PDA-ESI-tQ-MS/MS) identified 38 coumarins that were characterized and quantified. Various furanocoumarins were the major components of HSO polyphenolics, including imperatorin, phellopterin, and isoimperatorin, and the total coumarin content in HSO varied from 181.14 to 238.42 mg/mL. The analysis of storage stability of the selected compounds in HSO indicated their good preservation after 3-year storage at cold and freezing temperatures. The application of the CO2-assisted effervescence method allowed the production of an HSO nanosuspension, which was used in a brain ischemia model of rats. The HSO nanosuspension enhanced cerebral hemodynamics and decreased the frequency of necrotic processes in the brain tissue. Thus, H. dissectum seeds are a good source of coumarins, and HSO nanosuspension promotes neuroprotection of the brain after lesions, which supports earlier ethnopharmacological data.

Caucasian Dragonheads: Phenolic Compounds, Polysaccharides, and Bioactivity of Dracocephalum austriacum and Dracocephalum botryoides.

Dracocephalum botryoides Steven and Dracocephalum austriacum L. are unexplored species of the Dracocephalum genus (Lamiaceae family) with a distribution in the Caucasus, where they are used in folk medicine and local cuisine. There are no data on the chemical composition of these Dracocephalum species. In this study, the application of a liquid chromatography-mass spectrometry technique for the metabolite profiling of methanol extracts from herbs and roots of D. austriacum and D. botryoides resulted in the identification of 50 compounds, including benzoic acid derivatives, phenylpropanoids, flavonoids and lignans. Water-soluble polysaccharides of the herbs and roots of D. austriacum and D. botryoides were isolated and characterized as mostly pectins with additive arabinogalactan-protein complexes and starch-like compounds. The antioxidant potential of the studied extracts of Dracocephalum and selected phenolics and water-soluble polysaccharides were investigated via radical-scavenging and ferrous (II) ion chelating assays. This paper demonstrates that herbs and roots of D. austriacum and D. botryoides are rich sources of metabolites and could be valuable plants for new biologically active products. To the best of our knowledge, this is the first study of whole plant metabolites and their antioxidant activity in D. austriacum and D. botryoides.

Metabolites of Siberian Raspberries: LC-MS Profile, Seasonal Variation, Antioxidant Activity and, Thermal Stability of Rubus matsumuranus Phenolome.

Rubus matsumuranus H. Lev. & Vaniot, a famous Siberian shrub of the Rosaceae family, is used in the folk medicine of nomads (Buryats, Yakuts, Soyots, and Mongols) as a remedy for the treatment of diseases of the respiratory and hepatobiliary systems. The lack of scientific information on R. matsumuranus leaves contributed to the investigation of the metabolomic profile and biological activity of this plant. In this study, metabolites of R. matsumuranus leaves in three stages (active growth, flowering, and fruiting) were characterised using high-performance liquid chromatography with photodiode array and electrospray ionisation triple quadrupole mass spectrometric detection (HPLC-PDA-ESI-tQ-MS). In total, 63 compounds were identified, including gallic acid derivatives, hydroxycinnamates, catechins, procyanidins, flavonols, and ellagitannins. Lambertianin C (57.11 mg/g of dry weight, DW), miquelianin (39.63 mg/g DW), and kaempferol-3-O-glucuronide (31.18 mg/g DW) were the major compounds in R. matsumuranus leaves. As a result of the HPLC-PDA-based assay to determine the antioxidant activity, it was revealed that lambertianin A, sanguiin H6, lambertianin C, and sanguiin H11 were effective scavengers of free radicals (2,2-diphenyl-1-picrylhydrazyl, DPPH•) and possessed Fe2+-chelating activity. After an investigation of the phenolic content in infusions and decoctions obtained by extraction with water at different temperatures, it was revealed that a hot infusion (80 °C) is a phenolic-rich preparation of R. matsumuranus leaves. Our research suggests that R. matsumuranus leaves are a rich source of phenolic compounds with high antioxidant properties and that this could be a prospective plant for new functional products.

Water-Soluble Melanoidin Pigment as a New Antioxidant Component of Fermented Willowherb Leaves (Epilobium angustifolium).

Willowherb (Epilobium angustifolium L., family Onagraceae) is a well-known food and medicinal plant used after fermentation as a source of beverages with high antioxidant potential. Despite this long history of use, only a few papers have described the chemical profile and bioactivity of fermented willowherb tea in general. To understand the basic metabolic differences of non-fermented and fermented E. angustifolium leaves, we used general chemical analysis, high-performance liquid chromatography with photodiode array detection and electrospray ionization triple quadrupole mass spectrometric detection assay, and an isolation technique. As a result, the content of 14 chemical groups of compounds was compared in the two plant materials; 59 compounds were detected, including 36 new metabolites; and a new water-soluble phenolic polymer of melanoidin nature was isolated and characterized. The fundamental chemical shifts in fermented E. angustifolium leaves relate mainly to the decrease of ellagitannin content, while there is an increase of melanoidin percentage and saving of the antioxidant potential, despite the significant changes detected. The strong antioxidative properties of the new melanoidin were revealed in a series of in vitro bioassays, and a simulated gastrointestinal and colonic digestion model demonstrated the stability of melanoidin and its antioxidant activity. Finally, we concluded that the new melanoidin is a basic antioxidant of the fermented leaves of E. angustifolium, and it can be recommended for additional study as a promising food and medicinal antioxidant agent.

Caffeoylquinic Acids and Flavonoids of Fringed Sagewort (Artemisia frigida Willd.): HPLC-DAD-ESI-QQQ-MS Profile, HPLC-DAD Quantification, in Vitro Digestion Stability, and Antioxidant Capacity.

Fringed sagewort (Artemisia frigida Willd., Compositae family) is a well-known medicinal plant in Asian medical systems. Fifty-nine hydroxycinnamates and flavonoids have been found in A. frigida herbs of Siberian origin by high-performance liquid chromatography with diode array and electrospray triple quadrupole mass detection (HPLC-DAD-ESI-QQQ-MS). Their structures were determined after mass fragmentation analysis as caffeoylquinic acids, flavone O-/C-glycosides, flavones, and flavonol aglycones. Most of the discovered components were described in A. frigida for the first time. It was shown that flavonoids with different types of substitution have chemotaxonomic significance for species of Artemisia subsection Frigidae (section Absinthium). After HPLC-DAD quantification of 16 major phenolics in 21 Siberian populations of A. frigida and subsequent principal component analysis, we found substantial variation in the selected compounds, suggesting the existence of two geographical groups of A. frigida. The antioxidant activity of A. frigida herbal tea was determined using 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH•) and hydrophilic/lipophilic oxygen radical absorbance capacity (ORAC) assays and DPPH•-HPLC profiling, revealing it to be high. The effect of digestive media on the phenolic profile and antioxidant capacity of A. frigida herbal tea was assessed under simulated gastrointestinal digestion. We found a minor reduction in caffeoylquinic acid content and ORAC values, but remaining levels were satisfactory for antioxidant protection. These results suggest that A. frigida and its food derivate herbal tea could be recommended as new plant antioxidants rich in phenolics.

Khellactone Derivatives and Other Phenolics of Phlojodicarpus sibiricus (Apiaceae): HPLC-DAD-ESI-QQQ-MS/MS and HPLC-UV Profile, and Antiobesity Potential of Dihydrosamidin.

With obesity, the consumption of phenolic-enriched food additives as a part of traditional nutrition avoids the negative implications of eating high-calorie products. This study investigated the new herbal food additive, Phlojodicarpus sibiricus roots and herb, ubiquitously used in Siberia as a spice. Chromatographic techniques such as HPLC-DAD-ESI-QQQ-MS/MS and microcolumn HPLC-UV were the basic instruments for component profiling and quantification, and antiobesity potential was investigated using a differentiated 3T3-L1 adipocytes assay. We found that the roots and herb of P. sibiricus were high-coumarin-containing additives inhibiting triacylglycerol accumulation in 3T3-L1 preadipocytes. Forty-one phenolics were detected in P. sibiricus extracts, and 35 were coumarins, including 27 khellactone derivatives present as esters and glucosides. Total coumarin content varied from 36.16 mg/g of herb to 98.24 mg/g of roots, and from 0.32 mg/mL to 52.91 mg/mL in P. sibiricus preparations. Moreover, Siberian populations of P. sibiricus were characterised by a different HPLC-based coumarin profile. The most pronounced inhibiting effect on triacylglycerol accumulation in 3T3-L1 preadipocytes was shown for dihydrosamidin (khellactone 3'-O-isovaleroyl-4'-O-acetyl ester), which was more active than other khellactone esters and glucosides. The results demonstrated that if used as a food additive Phlojodicarpus sibiricus could be a source of bioactive coumarins of the khellactone group with high antiobesity potential.

Angelica gigas Nakai and Decursin Downregulate Myc Expression to Promote Cell Death in B-cell Lymphoma.

Angelica gigas Nakai (AGN) is an oriental traditional medicine to treat anemia, dysmenorrhea, and migraine. However, its anti-lymphoma effect is yet to be tested. Here, we demonstrated that AGN and its major component decursin target Myc to suppress lymphomagenesis in vitro and in vivo. AGN inhibited cell viability in multiple B lymphoma cells, while sparing normal splenocytes and bone marrow cells. Increased cleaved PARP level and caspase 3/7 activity and the repression of survival-promoting AKT/mTOR and MAPK pathways downstream of BCR, were responsible for the pro-apoptotic effects of AGN. We found that Myc, a prominent downstream target of these signaling pathways, contributes to AGN-induced cell death. Moreover, co-treatment with AGN and a Myc inhibitor, JQ1 or 10058-F4 yielded synergistic cytotoxic activities against cancer cells with markedly reduced Myc expression. AGN downregulated Myc expression and suppressed tumorigenesis in Eµ-myc transgenic mice. The proapoptotic activities of AGN were recapitulated by decursin, indicating that the anti-tumor effect of AGN was mainly caused by decursin. These findings suggest that AGN and decursin possess potent anti-lymphoma activity, and combination therapies with AGN/decursin and a Myc inhibitor to target Myc more efficiently could be a valuable avenue to explore in the treatment of B-cell lymphoma.

Bioactive Phenolics of the Genus Artemisia (Asteraceae): HPLC-DAD-ESI-TQ-MS/MS Profile of the Siberian Species and Their Inhibitory Potential Against α-Amylase and α-Glucosidase.

Artemisia genus of Asteraceae family is a source of medicinal plants known worldwide and used as ethnopharmacological remedies for the treatment of diabetes in Northern Asia (Siberia). The aim of this study was to determine the phenolic profile of 12 Siberian Artemisia species (A. anethifolia, A. commutata, A. desertorum, A. integrifolia, A. latifolia, A. leucophylla, A. macrocephala, A. messerschmidtiana, A. palustris, A. sericea, A. tanacetifolia, A. umbrosa) and to test the efficacy of plant extracts and pure compounds for antidiabetic potential. Finally, by HPLC-DAD-ESI-TQ-MS/MS technique, 112 individual phenolic compounds were detected in Artemisia extracts in a wide range of concentrations. Some species accumulated rare plant phenolics, such as coumarin-hemiterpene ethers (lacarol derivatives) from A. latifolia and A. tanacetifolia; melilotoside from A. tanacetifolia; dihydrochalcones (davidigenin analogs) from A. palustris; chrysoeriol glucosides from A. anethifolia, A. sericea, and A. umbrosa; eriodictyol glycosides from A. messerschmidtiana; and some uncommon flavones and flavonols. The predominant phenolic group from Artemisia species herb was caffeoylquinic acid (CQAs), and in all species, the major CQAs were 5-O-CQA (20.28-127.99 µg/g) and 3,5-di-O-CQA (7.35-243.61 µg/g). In a series of in vitro bioassays, all studied Artemisia extracts showed inhibitory activity against principal enzymes of carbohydrate metabolism, such as α-amylase (IC50 = 150.24-384.14 µg/mL) and α-glucosidase (IC50 = 214.42-754.12 µg/mL). Although many phenolic compounds can be inhibitors, experimental evidence suggests that the CQAs were key to the biological response of Artemisia extracts. Mono-, di- and tri-substituted CQAs were assayed and showed inhibition of α-amylase and α-glucosidase, with IC50 values of 40.57-172.47 µM and 61.08-1240.35 µM, respectively, and they were more effective than acarbose, a well-known enzyme inhibitor. The results obtained in this study reveal that Siberian Artemisia species and CQAs possess a pronounced inhibitory activity against α-amylase and α-glucosidase and could become a complement to synthetic antidiabetic drugs for controlling blood glucose level.

Isorhamnetin and Quercetin Derivatives as Anti-Acetylcholinesterase Principles of Marigold (Calendula officinalis) Flowers and Preparations.

Marigold (Calendula officinalis L.) is one of the most common and widespread plants used medicinally all over the world. The present study aimed to evaluate the anti-acetylcholinesterase activity of marigold flowers, detect the compounds responsible and perform chemical analysis of marigold commercial products. Analysis of 23 varieties of C. officinalis flowers introduced into Siberia allowed us to select the Greenheart Orange variety due to the superior content of flavonoids (46.87 mg/g) and the highest inhibitory activity against acetylcholinesterase (IC50 63.52 µg/mL). Flavonoids, isorhamnetin and quercetin derivatives were revealed as potential inhibitors with the application of high-performance liquid chromatography (HPLC) activity-based profiling. Investigation of the inhibitory activity of isorhamnetin glycosides demonstrated the maximal potency for isorhamnetin-3-О-(2'',6''-di-acetyl)-glucoside (IC50 51.26 µM) and minimal potency for typhaneoside (isorhamnetin-3-O-(2'',6''-di-rhamnosyl)-glucoside; IC50 94.92 µM). Among quercetin derivatives, the most active compound was quercetin-3-О-(2'',6''-di-acetyl)-glucoside (IC50 36.47 µM), and the least active component was manghaslin (quercetin-3-O-(2'',6''-di-rhamnosyl)-glucoside; IC50 94.92 µM). Some structure-activity relationships were discussed. Analysis of commercial marigold formulations revealed a reduced flavonoid content (from 7.18-19.85 mg/g) compared with introduced varieties. Liquid extract was the most enriched preparation, characterized by 3.10 mg/mL of total flavonoid content, and infusion was the least enriched formulation (0.41 mg/mL). The presented results suggest that isorhamnetin and quercetin and its glycosides can be considered as potential anti-acetylcholinesterase agents.

Agrimoniin, an Active Ellagitannin from Comarum palustre Herb with Anti-α-Glucosidase and Antidiabetic Potential in Streptozotocin-Induced Diabetic Rats.

Naturally existing α-glucosidase inhibitors from traditional herbal medicines have attracted considerable interest to treat type 2 diabetes mellitus (DM). The present study aimed to evaluate the anti-α-glucosidase activity of extracts from marsh cinquefoil (Comarum palustre L.), their hypoglycaemic action and detection of the responsible compounds. A 60% ethanol extract from C. palustre herb revealed the highest inhibitory activity against α-glucosidase (IC50 52.0 µg/mL). The HPLC analysis of the major compounds resulted in detection of 15 compounds, including ellagitannins, flavonoids, catechin and other compounds. Using HPLC activity-based profiling a good inhibitory activity of agrimoniin-containing eluates against α-glucosidase was demonstrated. The removal of ellagitannins from the C. palustre extract significantly decreased α-glucosidase inhibition (IC50 204.7 µg/mL) due to the high enzyme-inhibiting activity of the dominant agrimoniin (IC50 21.8 µg/mL). The hypoglycaemic effect of C. palustre extracts before and after ellagitannin removal, agrimoniin and insulin was evaluated on streptozotocin-induced experimental model. Diabetic rats treated with agrimoniin and C. palustre extract before ellagitannin removal showed significant increases in the levels of plasma glucose and glycosylated hemoglobin and significant decreases in the levels of plasma insulin and hemoglobin. The data obtained confirm the leading role of agrimoniin in the antidiabetic activity of the herb C. palustre and allows us to suggest the use of this plant as a possible dietary adjunct in the treatment of DM and a source of new oral hypoglycaemic agents.

Chemical Composition, Antioxidant and Anticholinesterase Activities of Gentianella azurea from Russian Federation.

Phytochemical study of Gentianella azurea (Bunge) Holub (Gentianaceae) collected in Buryatia Republic (Russian Federation) resulted in the isolation of twenty-one compounds including bellidifolin, bellidin, isobellidifolin, norswertianolin, isobellidifolin-8-O-ß-D-glucopyranoside, orientin, cynaroside, .cosmosiin, apigenin, 4'-O-caffeoylswertiamarin, swertiamarin-6'-O-ß-D-glucopyranoside and sweroside, firstly detected in this species. The extracts and individual compounds were shown to possess antioxidant and anticholinesterase potential.

Meadowsweet Teas as New Functional Beverages: Comparative Analysis of Nutrients, Phytochemicals and Biological Effects of Four Filipendula Species.

In recent years, the increased popularity of functional beverages such as herbal teas and decoctions has led to the search for new sources of raw materials that provide appropriate taste and functionality to consumers. The objective of this study was to investigate the nutritional, phytochemical profiles and bioactivities of possible functional beverages produced from F. ulmaria and its alternative substitutes (F. camtschatica, F. denudata, F. stepposa). The investigated decoctions were analyzed regarding their macronutrient, carbohydrate, organic acid, amino acid and mineral composition. Quantification of the main phenolic compounds in the decoctions of meadowsweet floral teas was performed by a microcolumn RP-HPLC-UV procedure; the highest content was revealed in F. stepposa tea. The investigation of the essential oil of four meadowsweet teas revealed the presence of 28 compounds, including simple phenols, monoterpenes, sesquiterpenes and aliphatic components. The dominance of methyl salicylate and salicylaldehyde was noted in all samples. Studies on the water soluble polysaccharides of Filipendula flowers allowed us to establish their general affiliation to galactans and/or arabinogalactans with an admixture of glucans of the starch type and galacturonans as minor components. The bioactivity data demonstrated a good ability of meadowsweet teas to inhibit amylase, α-glucosidase and AGE formation. Tea samples showed antioxidant properties by the DPPH•, ABTS•+ and Br• free radicals scavenging assays and the carotene bleaching assay, caused by the presence of highly active ellagitannins. The anti-complement activity of the water-soluble polysaccharide fraction of meadowsweet teas indicated their possible immune-modulating properties. Filipendula beverage formulations can be expected to deliver beneficial effects due to their unique nutritional and phytochemical profiles. Potential applications as health-promoting functional products may be suggested.

Bitter Gentian Teas: Nutritional and Phytochemical Profiles, Polysaccharide Characterisation and Bioactivity.

As a result of the wide distribution of herbal teas the data on nutritional characterisation, chemical profile and biological activity of these products are required. The decoctions of Gentiana algida, G. decumbens, G. macrophylla and G. triflora herb teas were nutritionally characterized with respect to their macronutrients, demonstrating the predominance of polysaccharides and low lipid content. Gentian decoctions were also submitted to a microcolumn RP-HPLC-UV analysis of phytochemicals demonstrating a high content of iridoids (177.18-641.04 µg/mL) and flavonoids (89.15-405.71 µg/mL). Additionally, mangiferin was detected in samples of G. triflora tea (19.89 µg/mL). Five free sugars (fructose, glucose, sucrose, gentiobiose, gentianose) were identified in all gentian teas studied, as well as six organic acids (malic, citric, tartaric, oxalic, succinic, quinic). Pectic polysaccharides with a high content of rhamnogalacturonans and arabinogalactans were also identified and characterized in gentian decoctions for the first time. Gentian tea decoctions and their specific compounds (gentiopicroside, loganic acid-6'-O-ß-d-glucoside, isoorientin, isoorientin-4'-O-ß-d-glucoside, mangiferin, water-soluble polysaccharides) showed a promising antimicrobial, anti-inflammatory and antioxidant potentials. Evidences obtained indicate the prospective use of gentian herb teas as food products and medicines.

Iridoids and Flavonoids of Four Siberian Gentians: Chemical Profile and Gastric Stimulatory Effect.

Some Gentiana species have been used by the nomadic people of Siberia as bitter teas or appetizers to eliminate digestive disorders (dyspepsia, heartburn, nausea, etc.). We studied the most frequently used gentians: Gentiana algida, G. decumbens, G. macrophylla and G. triflora. The aim of the present study was to evaluate the phytochemical features and gastrostimulatnt activity of these four gentian herbs. Five iridoids, seven flavones and mangiferin were detected in gentian herbs after analysis by microcolumn-RP-HPLC-UV-ESI-MS. A componential phytochemical profile of the G. decumbens herb is presented for the first time, as well as information about distinct phytochemicals found in gentian herbs. HPLC quantification of the specific compounds of gentian herbs demonstrated the high content of iridoids (24.73-73.53 mg/g) and flavonoids (12.92-78.14 mg/g). The results of biological activity evaluation of four gentian decoctions demonstrated their good ability to stimulate acid-, enzyme- and mucin-forming functions of the stomach attributed to mostly by iridoids and flavonoids. In general, it can be claimed that the gentian decoctions can be used as effective and safe appetizers and are also a good source of biologically active agents.

In Vitro Bioaccessibility, Human Gut Microbiota Metabolites and Hepatoprotective Potential of Chebulic Ellagitannins: A Case of Padma Hepaten® Formulation.

Chebulic ellagitannins (ChET) are plant-derived polyphenols containing chebulic acid subunits, possessing a wide spectrum of biological activities that might contribute to health benefits in humans. The herbal formulation Padma Hepaten containing ChETs as the main phenolics, is used as a hepatoprotective remedy. In the present study, an in vitro dynamic model simulating gastrointestinal digestion, including dialysability, was applied to estimate the bioaccessibility of the main phenolics of Padma Hepaten. Results indicated that phenolic release was mainly achieved during the gastric phase (recovery 59.38%-97.04%), with a slight further release during intestinal digestion. Dialysis experiments showed that dialysable phenolics were 64.11% and 22.93%-26.05% of their native concentrations, respectively, for gallic acid/simple gallate esters and ellagitanins/ellagic acid, in contrast to 20.67% and 28.37%-55.35% for the same groups in the non-dialyzed part of the intestinal media. Investigation of human gut microbiota metabolites of Padma Hepaten and pure ChETs (chebulinic, chebulagic acids) established the formation of bioactive urolithins (A, B, C, D, M5). The fact of urolithin formation during microbial transformation from ChETs and ChET-containing plant material was revealed for the first time. Evaluation of the protective effect of ChETs colonic metabolites and urolithins on tert-butyl hydroperoxide (t-BHP)-induced oxidative injury in cultured rat primary hepatocytes demonstrated their significant reversion of the t-BHP-induced cell cytotoxicity, malonic dialdehyde production and lactate dehydrogenase leakage. The most potent compound was urolithin C with close values of hepatoprotection to gallic acid. The data obtained indicate that in the case of Padma Hepaten, we speculate that urolithins have the potential to play a role in the hepatic prevention against oxidative damage.

A novel HPLC-assisted method for investigation of the Fe2+-chelating activity of flavonoids and plant extracts.

Flavonoids are a class of natural phenolic compounds that show antioxidant properties. Besides the known mechanisms of action of flavonoids (binding/inactivation of free radicals and other reactive oxygen species) that determine this effect, an important factor is their ability to bind transition metal ions. In this paper, we used a HPLC method with a prechromatographic reaction of a sample with Fe2+ ions (FeCA-HPLC) to characterize the Fe2+-chelating properties of individual compounds, their mixtures, and plant extracts. Using two classes of flavonoids (flavones, flavonols) the ability of compounds to bind Fe2+ ions due to a number of structural features of the compounds was shown. If the compounds possessed Fe2+-chelating properties, the decrease in the area of the chromatographic peaks on the chromatogram was marked. By comparing the resulting chromatogram with that of the untreated sample, it was possible to estimate the value of the effect. Application of this method for the analysis of plant extracts representing a mixture of substances allows determination of the compounds that have the greatest influence on the Fe2+-chelating activity.

Chemical composition and antioxidant activity of Tánara Ótó (Dracocephalum palmatum Stephan), a medicinal plant used by the North-Yakutian nomads.

Dracocephalum palmatum Stephan (Lamiaceae) is a medicinal plant used by the North-Yakutian nomads. From the crude ethanolic extract of the aerial parts of this plant, 23 compounds (phenylpropanoids, coumarins, flavonoids, and triterpenes) were isolated. Among these, eight compounds (salvianolic acid B, caftaric acid, cichoric acid, umbelliferone, aesculetin, apigenin-7-O-ß-D-glucuronopyranoside, isorhoifolin, and luteolin-4'-O-ß-D-glucopyranoside) were detected for the first time in the genus Dracocephalum. Their structures were elucidated based on chemical and spectral data. The levels of most of the compounds detected in the cultivated sample were close to that of the wild sample, indicating the reproducibility of the biologically active compounds of D. palmatum through cultivation. Investigation into the biological activity of D. palmatum under in vitro conditions demonstrated that its extracts have a strong antioxidant effect due to the presence of high concentrations of phenolic compounds.