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Common ragweed (Ambrosia artemisiifolia L.) is an invasive plant in Europe with spreading use in the contemporary folk medicine. The chemical composition of the above-ground parts is extensively studied, however, the metabolites of the roots are less discovered. By multiple chromatographic purification of the root extracts, we isolated thiophene A (1), n-dodecene (2), taraxerol-3-O-acetate (3), α-linoleic acid (4), (+)-pinoresinol (5), and thiophene E (7,10-epithio-7,9-tridecadiene-3,5,11-triyne-1,2-diol) (6). The 1H NMR data published earlier for 1 were supplemented together with the assignment of 13C NMR data. Thiophene E (6), which is reported for the first time from this species, exerted cytotoxic and antiproliferative effects on A-431 epidermoid skin cancer cells, whereas taraxerol-3-O-acetate (3) and α-linoleic acid (4) had slight antiproliferative effect on gynecological cancer cell lines. Thiophene E (6) and taraxerol-3-O-acetate (3) displayed antiproliferative and cytotoxic effects on MRC-5 fibroblast cells. Thiophene E (6) exerted weak antibacterial activity (MIC 25 μg/mL) on MRSA ATCC 43300, on Staphylococcus aureus ATCC 25923, Escherichia coli AG100 and E. coli ATCC 25922 both thiophenes were inactive. Although the isolated compounds exerted no remarkable cytotoxic or antiproliferative activities, the effects on MRC-5 fibroblast cells highlight the necessity of further studies to support the safety of ragweed root.

Context: Rhodiola rosea L. (Crassulaceae) is well-known to contain flavonoids such as the herbacetin derivative rhodiosin. However, flavonoids are not typically used in quality control. Objective: This study analyses two flavonoids of R. rosea rhizomes and roots for their potential as analytical markers. Materials and methods: Two constituents were isolated from ethanolic extracts via HPLC, identified via NMR and quantified via RP-HPLC. Presence and content variation was investigated according to extraction (solvent and repetitions), drying (temperature and duration) and sample origin (homogenously cultivated plants of different provenance, commercial samples). Results: Rhodiosin was identified as a main flavonoid, accompanied by 10-fold lower concentrated herbacetin. Both compounds were best extracted with 70–90% ethanol, but were also detectable in more aqueous extracts. Different drying conditions had no effect on the flavonoid content. These two flavonoids were consistently identified in rhizome and root extracts of over 100 R. rosea samples. Rhizomes tend to contain less flavonoids, with average ratios of rosavins to flavonoids of 1.4 (rhizomes) and 0.4 (roots). Provenance differences were detected in the range (rhodiosin plus herbacetin) of 760–6300 µg/mL extract corresponding to a maximum of approximately 0.5–4.2% (w/w) in the dry drug. Conclusions: For the first time, two main flavonoids present in R. rosea were quantified systematically. Rhodiosin and herbacetin can be detected simultaneously to phenylpropenoids or salidroside in authentic samples, influenced by the plant part examined and the plant origin. Rhodiosin and herbacetin may serve as additional marker to guarantee a consistent content of R. rosea products.

The chemical analysis of the methanol extract of Porodaedalea chrysoloma (Fr.) Fiasson & Niemela afforded the isolation of five compounds (1-5). The first two are phenolic derivatives: methyl (E)-3-(4-methoxycar-bonylphenoxy)-acrylate (1) is a new natural product, while methyl 3-(4-methoxycarbonylphenoxy)-propionate (2) was isolated from a natural source for the first time. The triterpene steroids ergone (3), 3β-hydroxyergosta-7,22-diene (4), and ergosterol (5) have not been previously identified in this species. The structures of the compounds were determined on the basis of NMR and MS spectroscopic analysis. The isolated fungal metabolites 1-5 were evaluated for their antioxidant activity. Compounds 1, 2, and 4 proved to possess considerable antioxidant effect in the ORAC assay with 2.21 ± 0.34, 1.58 ± 0.18, and 5.02 ± 0.47 mmol TE/g, respectively.

The detailed chemical analysis of the methanol extract of Meripilus giganteus (Pers.) P. Karst. led to the isolation of two new cerebrosides, mericeramides A (1) and B (2) together with cerebroside B (3), ergosterol (4), 3&beta, hydroxyergosta-7,22-diene (5), cerevisterol (6), 3&beta, hydroxyergosta-6,8(14),22-triene (7), 3&beta, O-glucopyranosyl-5,8-epidioxyergosta-6,22-diene (8) and (11E,13E)-9,10-dihydroxy-11,13-octadecadienoic acid (9). The structures of the compounds were determined on the basis of NMR and MS spectroscopic analysis. Mericeramide A (1) is the first representative of halogenated natural cerebrosides. The isolated fungal metabolites 1&ndash, 9 were evaluated for their antioxidant activity using the oxygen radical absorbance capacity (ORAC) assay. Compounds 2, 5 and 9 proved to possess considerable antioxidant effects, with 2.50 &plusmn, 0.29, 4.94 &plusmn, 0.37 and 4.27 &plusmn, 0.05 mmol TE/g values, respectively. The result obtained gives a notable addition to the chemical and bioactivity profile of M. giganteus, highlighting the possible contribution of this species to a versatile and balanced diet.

The phenylpropenoid glycosides rosavin, rosarin, rosin summarised as ‘total rosavins’ are quality indicators of Rhodiola rosea L. Here we report the systematic quantification of these glycosides and the aglycon cinnamyl alcohol in various provenances cultivated homogenously at 1580 m altitude. (I) We examined rhizomes versus roots in cultivation year 9 (20 provenances). Extracts (70% ethanol) contained 0.5–4.3 mg/mL (rhizomes) and 0.4–2.5 mg/mL (roots) total rosavins. The rosavin/cinnamyl alcohol ratio (average rhizomes 8.1:1, roots 6.2:1), was more influenced by plant origin than plant part. We additionally analysed salidroside including its aglycon tyrosol. The rosavins/salidroside ratios (including aglycons) of 6.4:1 (rhizome) and 5.5:1 (root) indicated authentic R. rosea independent of plant part and origin. (II) Rhizomes extracts (8 provenances) from various dates during years 6 and 7 contained 0.4–4.8 mg/mL total rosavins corresponding to 0.2–3.0% in the dry drug. Age (decreasing trend) and provenance impact were superposed by seasonal variation with a phenylpropenoid peak in spring. Rosavin/cinnamyl alcohol ratios in North European plants were 3–8:1, for Alpine/Pyrenean plants 9–14:1. (III) Compared to our previous dataset from cultivation in South England, on average, there was no major difference between phenylpropenoid values from cultivation at 65 m and 1580 m apart from moderately more cinnamyl alcohol at higher altitude. As per provenance, absolute values were site dependent but phenylpropenoid glycoside/aglycon ratios consistent. In conclusion, this is the first systematic investigation for a high altitude cultivation of R. rosea demonstrating the major extent plant part, season and age influence absolute phenylpropenoid values. In contrary, relative phenolic compound profiles are mostly origin-determined, independent of cultivation conditions and site, and could be used for authentication in quality control.

Objective Diterpene alkaloids are secondary plant metabolites and chemotaxonomical markers with a strong biological activity. These compounds are characteristic for the Ranunculaceae family, while their occurrence in other taxa is rare. Several species of the Spiraea genus (Rosaceae) are examples of this rarity. Screening Spiraea species for alkaloid content is a chemotaxonomical approach to clarify the classification and phylogeny of the genus. Novel pharmacological findings make further investigations of Spiraea diterpene alkaloids promising. Results Seven Spiraea species were screened for diterpene alkaloids. Phytochemical and pharmacological investigations were performed on Spiraea chamaedryfolia, the species found to contain diterpene alkaloids. Its alkaloid-rich fractions were found to exert a remarkable xanthine-oxidase inhibitory activity and a moderate antibacterial activity. The alkaloid distribution within the root was clarified by microscopic techniques. Electronic supplementary material The online version of this article (10.1186/s13104-017-3013-y) contains supplementary material, which is available to authorized users.

Wheatgrass is widely used in the alternative medicine, however, there is a lack of clinical evidence to support its efficacy. Although based on its chemical composition, data from animal experiments and clinical trials, the use of juice and extracts of Triticum shoots seems to be safe, clinical reports point out its potential interaction with oral anticoagulants. The aim of our study was to assess the interaction of wheatgrass with warfarin in rats and to assess its flavonoid content. Three groups of animals were treated orally with wheatgrass, warfarin, or the combination of wheatgrass and warfarin for five days. Clotting assays were performed using platelet-poor plasma. Prothrombin time was determined by optical and mechanical coagulometers. Flavonoid content of wheatgrass was measured by HPLC. The effect of wheatgrass on prothrombin time was not confirmed. Co-administration of wheatgrass and warfarin did not result in diminished anticoagulant activity. Low amount of flavonoids was detected in wheatgrass juice, the total flavonoid content was 0.467 mg/100 g lyophilized juice powder. The previously reported rutin, quercetin and apigenin was not detected by us. Our results do not confirm the probability of interaction of wheatgrass with oral anticoagulants. However, the low flavonoid content of wheatgrass does not support its use as an antioxidant.

Ten representative Central European phellinoid Hymenochaetaceae species (Phellinus sensu lato) were selected to examine their potential pharmacological activity. In this study 40 organic (n-hexane, chloroform, 50% methanol) and aqueous extracts with different polarities were analyzed for their antimicrobial, antioxidant, and xanthine oxidase (XO)--inhibitory properties. Fomitiporia robusta, Fuscoporia torulosa, Phellopilus nigrolimitatus, and Porodaedalea chrysoloma showed moderate antibacterial activity; Bacillus subtilis ATCC 6633, methicillin-resistant Staphylococcus aureus ATCC 43300, and Moraxella catarrhalis ATCC 43617 were the strains most susceptible to the examined fungal species. The in vitro antioxidant and XO assays demonstrated that most of the selected species possess remarkable antioxidant and XO-inhibitory activities. The water extracts in general proved to be more active antioxidants than organic extracts. In the case of F. torulosa, Ph. Nigrolimitatus, and P. chrysoloma, the results of DPPH tests correlate well with those obtained by oxygen radical absorbance capacity tests; these mushrooms presented high antioxidant activities in both assays. Future studies involving phellinoid Hymenochaetaceae species are planned, which may furnish novel results in terms of the species' pharmacological activity and the specific compounds responsible for the observed activity.

The present study was designed to assess the influence of geographical factors on essential oil (EO) composition, along with antiradical potential and phytochemical contents of Ferulago angulata (Schltdl.) Boiss (Apiaceae) extracts for the first time. The aerial parts were hydrodistilled by Clevenger apparatus and subjected to gas chromatography coupled with flame ionization detector (GC/FID) and mass spectroscopy (GC/MS). The EO yields were significantly different from populations 'Mongar' (south-slope, 3000 m) with 1.34±0.06 % and 'Male-Amiri' (north slope, 2600 m) with 0.18±0.05 % of total oil. Thirty-nine compounds were identified from the EOs of nine populations. α-Pinene was the predominant component ranging from 20.84 to 49.06 % in 'Gandomkar' (north-slope, 2500 m) and 'Mongar' (3000 m), respectively. The methanolic extract of 'Mongar' (north-slope at 2500 m) possessed the highest total phenolic contents. Also, this population logically exhibited potent antiradical activity using both 1,1-diphenyl-2-picrylhydrazyl (DPPH) and oxygen radical absorbance capacity (ORAC) assays with EC50 of 42.07±4.12 μg/mL and 8.34±0.21 mmol Trolox® equivalents/g, respectively. Due to its moderate free-radical scavenging potential and high α-pinene content, the population 'Mongar' might be considered as a perspective raw material in food and phytopharmaceutical industries.

Withania somnifera (L.) Dunal originates mainly from Northern and Southern India. Primarily the roots are used in the Ayurvedic medicine as tonic, sedative hypnotic, adstringent, diuretic, emetic, and aphrodisiac. In Europe, it is widely used in food supplements. Due to the many effects and uses of this plant, the analysis of the Withania somnifera and optimization of industrial processing is nowadays an important issue. In Europe W. frutescens is native, and may be interesting for industrial preparation due to its similar phytochemical profile to W. somnifera. The point of our research was to develop an effective extraction and hydrolysis method of the Withania frutescens leaves to optimize the industrial processing.

Background: Inhalation of manganese-containing metal fumes at workplaces can cause central nervous damage including a Parkinson-like syndrome. Oxidative stress is likely to be involved in the pathomechanism, due to the presence of nano-sized metal oxide particles with high biological and chemical activity. Oxidative damage of the nervous system could be prevented or ameliorated by properly applied antioxidants, preferably natural ones such as green tea, a popular drink. The aim of this work was to see if orally applied green tea brew could diminish the functional neurotoxicity of manganese dioxide nanoparticles introduced into the airways of rats.; Results: Young adult male Wistar rats were treated intratracheally for 6 weeks with a suspension of synthetic MnO2 nanoparticles (4 mg/kg body weight), and received green tea brew (1 g leaves 200 mL-1 water) as drinking fluid. Reduced body weight gain, indicating general toxicity of the nanoparticles, was not influenced by green tea. However, in rats receiving green tea the nervous system effects - changes in the spontaneous and evoked cortical activity and peripheral nerve action potential - were diminished.; Conclusion: The use of green tea as a neuroprotective functional drink seems to be a viable approach. © 2016 Society of Chemical Industry.; © 2016 Society of Chemical Industry.

Rotifers have been widely used as well-characterized models of aging, since their multiorgan character makes them suitable as in vivo toxicological and lifespan models. Here we report the assessment of four adaptogenic plants and their extracts for the first time in this model. The effects on rotifer viability of extracts and characteristic active markers of Panax ginseng, Withania somnifera, Leuzea carthamoides, and Rhodiola rosea were tested in vivo. The crude extracts were nontoxic to Philodina acuticornis bdelloid rotifers; however, the pure substances of the plants influenced negatively the viability. Ginsenoside Rb1 and secondary metabolites of Withania somnifera exerted deleterious effect on the animals. The aglycone tyrosol and cinnamyl alcohol (from Rhodiola rosea) were more toxic than their glycosides salidroside and rosavin. Although the 20-OH-ecdysone and ajugasterone C (from Leuzea carthamoides) are chemically very similar, the latter was less toxic.

Background: Centaurea virgata Lam. is a species widely used in the traditional medicine in Turkey for the treatment of diabetes, allergy and gastric ulcers. The rationale of its use in the therapy has not been studied previously, therefore the present work aimed at the chemical-pharmacological evaluation of the plant. Objective: The xanthine oxidase (XO) inhibitory activity of the MeOH extract and its subextracts (n-hexane, CHCl3 and remaining MeOH-H2O) prepared from C. virgata was investigated in vitro. Moderate activity was exerted in case of the CHCl3 extract (98.9 ± 15.8 µg/mL), therefore constituents of this extract were analysed. Method: Different purification steps, such as VLC, CPC, PLC and crystallization were used for the isolation, and ESIMS, NMR, LC-MS and authentic standards were applied for identification of the compounds. XO inhibitory and DPPH assays were used for evaluation of the bioactivities. Results: Sesquiterpenes [8α-hydroxysonchucarpolide, 8α-(3,4-dihydroxy-2-methylene-butanoyloxy)-dehydromelitensine, and cnicin], flavones (apigenin, hispidulin, salvigenin, eupatorin, 3’-methyleupatorin), and the flavonol isokaempferide were isolated from the active extract. The XO-inhibitory activity of these compounds was analyzed using allopurinol as a positive control (IC50 7.49 ± 0.29 μM). It was found that sesquiterpenes and flavonoids, containing 7-OMe group, are inactive. Conclusion: 7-Hydroxyflavones (apigenin and hispidulin) exerted significant XO inhibitory effect with IC50 values of 0.99 ± 0.33 μM and 4.88 ± 1.21 μM, respectively. Therefore these compounds are responsible for the XO-inhibitory effect of the extract. The free radical scavenging activity of the isolated flavonoids were determined by DPPH assay, and it was stated that none of the compounds have substantial antioxidant activity, therefore the reduced generation of reactive oxygen species may be the consequence only of XO inhibition.

Naringenin is one of the most abundant dietary flavonoids exerting several beneficial biological activities. Synthetic modification of naringenin is of continuous interest. During this study our aim was to synthesize a compound library of oxime and oxime ether derivatives of naringenin, and to investigate their biological activities. Two oximes and five oxime ether derivatives were prepared, their structure has been elucidated by NMR and high-resolution mass spectroscopy. The antiproliferative activity of the prepared compounds was evaluated by MTT assay against human leukemia (HL-60) and gynecological cancer cell lines isolated from cervical (HeLa, Siha) and breast (MCF-7, MDA-MB-231) cancers. Tert-butyl oxime ether derivative exerted the most potent cell growth inhibitory activity. Moreover, cell cycle analysis suggested that this derivative caused a significant increase in the hypodiploid (subG1) phase and induced apoptosis in Hela and Siha cells, and induced cell cycle arrest at G2/M phase in MCF-7 cells. The proapoptotic potential of the selected compound was confirmed by the activation of caspase-3. Antioxidant activities of the prepared molecules were also evaluated with xanthine oxidase, DPPH and ORAC assays, and the methyl substituted oxime ether exerted the most promising activity.

The present study aimed at assessing the influence of ecological factors on volatile oil content and antiradical potential of Prangos ferulacea. The essential oil (EO) content and composition of different plant parts were also compared. Among 22 identified compounds by gas chromatography (GC) flame ionization detector and GC-mass spectrometry, monoterpene hydrocarbons as the major constituents contributed to 27.6% to 83.4% of the oil deriving from plants growing on the northern steeps of “Gandomkar” region at 2600 m (G.N-2600) and “Male-Amiri” at 2300 m height (MA.N-2300), respectively. Immature seed and leaf samples of “Male-Amiri” with 3.0% ± 0.16% and 0.79% ± 0.03% of EO content represented the samples with the highest and lowest EO yields, respectively. Whereas the EO of the leaves mostly contained δ-3-carene and α-bisabolol, other parts were rich in α- and β-pinene. Extracts of accessions “G.N-2600” (EC50 = 13.11 ± 0.69 μg/mL) and “M.S-2500” (10.55 ± 0.41 mmol TE/g) exhibited the most potent antiradical activities in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) and Oxygen Radical Absorbance Capacity (ORAC) assays, respectively. Because of the extensive use of this species in traditional foods and the remarkable bioactivities of α- and β-pinene and δ-3-carene, the EO of the plant can be considered as a valuable raw material in phytopharmaceutical and food industries.

Matricaria chamomilla L. is a popular medicinal herb that is used for healing various diseases and is widely distributed worldwide in temperate climate zones, and even in the subtropical climate of Southern and Western Iran. This study was aimed at comparing the volatile oil constituents, along with antiradical potential and HPLC analysis of methanolic extracts from twelve plant samples growing in Iran. The present research was carried out for the first time on these populations. Among seventeen identified volatile chemicals evaluated by GC/MS and GC/FID, representing 92.73&ndash, 97.71% of the total oils, &alpha, bisabolone oxide A (45.64&ndash, 65.41%) was the major constituent, except in case of &ldquo, Sarableh&rdquo, as a new chemotype, where (E)- and (Z)-&gamma, bisabolene (42.76 and 40.08%, respectively) were the predominant components. Oxygenated sesquiterpenes (53.31&ndash, 74.52%) were the most abundant compounds in the samples excluding &ldquo, with 91.3% sesquiterpene hydrocarbons. &ldquo, also exerted the most potent antioxidant capacity with EC50 = 7.76 &plusmn, 0.3 &micro, g/mL and 6.51 &plusmn, 0.63 mmol TE (Trolox&reg, equivalents)/g. In addition, populations &ldquo, Lali&rdquo, and &ldquo, Bagh Malek&rdquo, contained the highest amounts of apigenin and luteolin with 1.19 &plusmn, 0.01 mg/g and 2.20 &plusmn, 0.0 mg/g of plant material, respectively. Our findings depict a clear correlation between phytochemical profiles and antiradical potential of M. chamomilla and geographical factors.

Inhalation of manganese-containing metal fumes at workplaces can cause central nervous damage including a Parkinson-like syndrome. Oxidative stress is likely to be involved in the pathomechanism, due to the presence of nano-sized metal oxide particles with high biological and chemical activity. Oxidative damage of the nervous system could be prevented or ameliorated by properly applied antioxidants, preferably natural ones such as green tea, a popular drink. The aim of this work was to see if orally applied green tea brew could diminish the functional neurotoxicity of manganese dioxide nanoparticles introduced into the airways of rats.Young adult male Wistar rats were treated intratracheally for 6 weeks with a suspension of synthetic MnOThe use of green tea as a neuroprotective functional drink seems to be a viable approach. © 2016 Society of Chemical Industry.