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Carpesium cernuum L., one of the two Carpesium species occurring in Europe, in the Far East and India, found use as a vegetable and a traditional medicinal remedy for several ailments. In the present study, compositions of essential oils distilled from roots and shoots of C. cernuum plants, cultivated in the open field, have been studied by GC-MS-FID supported by NMR spectroscopy. The analyses led to the identification of 120 compounds in total, of which 115 were found in aerial parts and 37 in roots of the plants. The major constituents found in the oil from shoots were: α-pinene (35%) and 2,5-dimethoxy-p-cymene (thymohydroquinone dimethyl ether, 12%), whereas 2,5-dimethoxy-p-cymene (55%), thymyl isobutyrate (9%) and thymol methyl ether (8%) predominated in the essential oil obtained from the roots. Antibacterial and cytotoxic activities of the essential oils distilled from C. cernuum were also tested. The essential oil from aerial parts of the plant demonstrated good inhibitory activity against Staphylococcus aureus ATCC 29213 and Escherichia coli ATCC 25922 (MIC: 15.6 μL/mL).

Large quantities of blackberry seeds are produced as a pomace during the processing of juice and jam production; this by-product is a very interesting raw material both for oil manufacturing and as a source of bioactive compounds. In this work the composition, yield and antioxidant activity of three types of Rubus fructicosus pomace extracts isolated by liquid extraction using solvents of different polarity, as well with supercritical CO2 fluid extraction have been compared.; Results: The highest extract yield was reported for Soxhlet extraction using ethanol as a solvent (14.2%). Supercritical carbon dioxide and hexane extracts were characterised by the highest content of phytosterols (1445 and 1583 mg 100 g-1 of extract, respectively) among which β-sitosterol was the main one, while the concentration of tocopherols, with predominant γ-isomer, was the highest for both hexane and ethanol extracts, being 2364 and 2334 mg 100 g-1 , respectively. Using a GC-MS method 95 volatiles, in which non-saturated aldehydes were predominant, were identified in the essential oil of seed pomace and in the volatile oil isolated from supercritical extract. The ethanolic extract which is characterised by the highest phenolic content (9443 mg GAE 100 g-1 ) exhibited the highest antioxidant activity (according to the ABTS•+ and DPPH• assays).; Conclusion: All pomace extracts examined were of high quality, rich in essential omega fatty acids and with a very high content of bioactive compounds, such as phytosterols and tocopherols. The high nutritional value of extracts from berry seed pomace could justify the commercialisation of specific extracts not only as food additives but also as cosmetic components. © 2017 Society of Chemical Industry.; © 2017 Society of Chemical Industry.

Carpesium divaricatum Sieb. and Zucc. has long been used both as traditional medicine and seasonal food. The most extensively studied specialized metabolites synthesized by the plant are sesquiterpene lactones of germacrane-type. Low-molecular and volatile terpenoids produced by C. divaricatum, however, have never been explored. In this work, compositions of essential oils distilled from roots and shoots of C. divaricatum plants, cultivated either in the open field or in the glasshouse have been studied by GC-MS-FID supported by NMR spectroscopy. The analyses led to the identification of 145 compounds in all, 112 of which were localized in aerial parts and 80 in roots of the plants grown in the open field. Moreover, remarkable differences in composition of oils produced by aerial and underground parts of C. divaricatum have been observed. The major volatiles found in the shoots were: α-pinene (40%), nerol (4%) and neryl-isobutyrate (3%), whereas predominant components of the root oil were 10-isobutyryloxy-8,9-epoxythymyl-isobutyrate (29%), thymyl-isobutyrate (6%) and 9-isobutyryloxythymyl-isobutyrate (6%). In the analyzed oils, seventeen thymol derivatives were identified. Among them eight compounds were specific for roots. Roots of the plants cultivated in the glasshouse were, in general, a poor source of essential oil in comparison with those of the plants grown in the open field. Chemophenetic relationships with other taxa of the Inuleae-Inulineae were also briefly discussed.

Impatiens parviflora is non-native invasive plant species occupying large areas all over the Europe and threatens native communities by altering their species composition and reducing native biodiversity. The factor responsible for its spreading could be explained by releasing biochemical to the environment. On the other hands, high demand on secondary metabolites as potential source of new ecofriendly biocides could be beneficial. The analysis of I. parviflora essential oil (EO) led us to identify more than 60 volatiles. The main compound was hexahydrofarnesyl acetone, other dominant components were phytol, carvacrol, germacra-4(15),5,10(14)-trien-1-&alpha, ol, and pentacosane. The potential phytotoxic effect of I. parviflora EO collected in two vegetation periods (summer and autumn) was evaluated on seed germination and root elongation of three dicot species (Raphanus sativus, Lepidum sativum, and Lactuca sativa) and on one monocot species (Triticum aestivum). The seed germination of only one dicot species, L. sativa, was affected by both EOs. In contrast, seed germination of monocot species T. aestivum was influenced only by the highest doses of EOs isolated from I. parviflora in autumn. The root elongation of tested plant species was less influenced by I. parviflora EOs. L. sativum showed sensitivity to one dose of EOs hydrodistilled in summer, while the monocot species was influenced by both EOs samples in highest doses. Our findings revealed that I. parviflora contained phenolics that were phytotoxic to the germination of some plant species, mainly at higher EOs doses, while root elongation of tested plants was not suppressed by essential oils.

Spreading of the plant species in new areas is supported by the hypothesis in which chemicals produced by alien species are allopathic to native plants. A novel weapon hypothesis was tested by using essential oil of dangerous alien species Heracleum mantegazzianum in laboratory conditions. Aboveground plant material was collected in south-east part of Slovakia, dried and hydrodistilled for essential oil isolation. Dominant compounds as octyl acetate (62.6%), hexyl 2-metylbutyrate (10.7%), hexyl isobutyrate (7.5%) and hexyl butyrate (6.5%) were identified by GC-MS. Potential phytotoxic activity was tested on three dicot plant species garden cress (Lepidium sativum L.), radish (Raphanus sativus L.) and lettuce (Lactuca sativa L.) and on one monocot plant species wheat Triticum aestivum L. Germination of the seeds of model plant species after influencing by different doses of essential oil of H. mantegazzianum as well as the roots length was evaluated. Lepidium sativum L. and Raphanus sativus L. were generally not sensitive to applied doses of essential oil although a little stimulation effect at some concentrations prevailed over inhibition effect. Similarly, in monocot species Triticum aestivum L., stimulation was visible in both root length and root number at two or one highest doses, respectively.

The chemical content and composition of the lipophilic extracts from seeds of some fir species: Abies alba, A. cephalonica, A. concolor, and A. koreana, as well as of a few spruce species: Picea abies, P. orientalis, and P. pungens, were examined. The amount of lipophilic extractives is diverse among the tree species and it varies from 9.8% to 41% of seeds. The chemical characterization showed significant differences, not only in the content, but also in the composition of extractives. However, most of the identified compounds like resin alcohols, -aldehydes, and -acids, as well as fatty acids, were detected in the seed extracts of all the examined tree species. The dominating identified compound group was esterified fatty acids (2.5 - 55.4% w/w of dry extract), occurring mainly as tri- and diglycerides, as well as free acids. The main representatives of this group were linoleic and oleic acids. The resin acids, among which the main were abietic, neoabietic, dehydroabietic, and palustric acids, were also detected at high levels, from 1.8% to 16.9% of the dry seed extracts. Phytosterols, tocopherols, resin hydrocarbons, and resin esters, as well as fatty alcohols were also identified. The coniferous tree seeds, as a renewable natural material, could represent a prospective raw material for producing valuable chemicals.

The objective of the study was to determine the content and composition of essential oil in the fresh young shoots of garden angelica collected in the first year of plant vegetation and to evaluate...

The mixture of three phytosterols (campesterol, stigmasterol and β-sitosterol), β-sitosterol 3-O-glucoside and syringin were isolated from hexane and methanol extract of Cirsium rivulare roots after chromatographic separation. The main component of the source was syringin which was obtained with the yield 0.08% of the dry source. In hexane extract, the qualitative and quantitative composition of fatty acids was determined. The predominant component was linoleic acid (23.31 mg/g of extract). The extracts showed antioxidant activity. The ability to scavenge DPPH• free radical was in correlation with appointed total phenol content. The not-defatted methanolic extract was the most active. Hexane and defatted methanol extracts showed moderate antibacterial activity against G(+) and G(−) strains with MIC and MBC ranged from 25 to 200 μg/mL.

In vitro cultivation is an effective way to increase pharmaceutical production. To increase ginsenoside production in hairy root cultures of American ginseng, the present study uses trans-anethole as an elicitor. The content of nine triterpene saponins was determined: Rb1, Rb2, Rb3, Rc, Rd, Rg1, Rg2, Re and Rf. Trans-anethole was found to stimulate saponin synthesis regardless of exposure time (24 and 72 h). Twenty-four hour exposure to 1 &mu, mol trans-anethole in the culture medium resulted in the highest increase of total saponin content (twice that of untreated roots), and optimum accumulation of Rb-group saponins, with ginsenoside Rc dominating (8.45 mg g&minus, 1 d.w.). In contrast, the highest mean content of protopanaxatriol derivatives was obtained for 10 &mu, mol trans-anethole. The Re metabolite predominated, reaching a concentration of 5.72 mg g&minus, 1 d.w.: a 3.9-fold increase over untreated roots. Elicitation with use of trans-anethole can therefore be an effective method of increasing ginsenoside production in shake flasks.

The work presents the results of an investigation into the molecular background of the activity of Cotoneaster fruits, providing a detailed description of their phytochemical composition and some of the mechanisms of their anti-inflammatory and antioxidant effects. GS-FID-MS and UHPLC-PDA-ESI-MS3 methods were applied to identify the potentially health-beneficial constituents of lipophilic and hydrophilic fractions, leading to the identification of fourteen unsaturated fatty acids (with dominant linoleic acid, 375.4–1690.2 mg/100 g dw), three phytosterols (with dominant β-sitosterol, 132.2–463.3 mg/100 g), two triterpenoid acids (10.9–54.5 mg/100 g), and twenty-six polyphenols (26.0–43.5 mg GAE/g dw). The most promising polyphenolic fractions exhibited dose-dependent anti-inflammatory activity in in vitro tests of lipoxygenase (IC50 in the range of 7.7–24.9 μg/U) and hyaluronidase (IC50 in the range of 16.4–29.3 μg/U) inhibition. They were also demonstrated to be a source of effective antioxidants, both in in vitro chemical tests (DPPH, FRAP, and TBARS) and in a biological model, in which at in vivo-relevant levels (1–5 μg/mL) they normalized/enhanced the nonenzymatic antioxidant capacity of human plasma and efficiently protected protein and lipid components of plasma against peroxynitrite-induced oxidative/nitrative damage. Moreover, the investigated extracts did not exhibit cytotoxicity towards human PMBCs. Among the nine Cotoneaster species tested, C. hjelmqvistii, C. zabelii, C. splendens, and C. bullatus possess the highest bioactive potential and might be recommended as dietary and functional food products.

The work presents the results of an investigation into the molecular background of the activity of Cotoneaster fruits, providing a detailed description of their phytochemical composition and some of the mechanisms of their anti-inflammatory and antioxidant effects. GS-FID-MS and UHPLC-PDA-ESI-MS3 methods were applied to identify the potentially health-beneficial constituents of lipophilic and hydrophilic fractions, leading to the identification of fourteen unsaturated fatty acids (with dominant linoleic acid, 375.4–1690.2 mg/100 g dw), three phytosterols (with dominant β-sitosterol, 132.2–463.3 mg/100 g), two triterpenoid acids (10.9–54.5 mg/100 g), and twenty-six polyphenols (26.0–43.5 mg GAE/g dw). The most promising polyphenolic fractions exhibited dose-dependent anti-inflammatory activity in in vitro tests of lipoxygenase (IC50 in the range of 7.7–24.9 μg/U) and hyaluronidase (IC50 in the range of 16.4–29.3 μg/U) inhibition. They were also demonstrated to be a source of effective antioxidants, both in in vitro chemical tests (DPPH, FRAP, and TBARS) and in a biological model, in which at in vivo-relevant levels (1–5 μg/mL) they normalized/enhanced the nonenzymatic antioxidant capacity of human plasma and efficiently protected protein and lipid components of plasma against peroxynitrite-induced oxidative/nitrative damage. Moreover, the investigated extracts did not exhibit cytotoxicity towards human PMBCs. Among the nine Cotoneaster species tested, C. hjelmqvistii, C. zabelii, C. splendens, and C. bullatus possess the highest bioactive potential and might be recommended as dietary and functional food products.

Simple esters of monoterpene alcohols are common secondary plant metabolites for which there are no scientific reports that provide relevant information for identification of these compounds. The aim of this work was to create a database of monoterpene esters which made the identification of these constituents possible. 64 esters of common monoterpene alcohols were obtained. Retention indices, mass spectra and nuclear magnetic resonance data are given. Copyright © 2016 John Wiley & Sons, Ltd.

Because of the bacterial drug resistance development, it is reasonable to investigate chemical compounds capable of preventing the spread of resistance to mupirocin (MUP), commonly used in staphylococcal eradication. The objective of the study was to verify the influence of essential oil compounds (EOCs) on the antibacterial activity of MUP against mupirocin-susceptible (MupS) and induced low-level mupirocin-resistant (MupRL) methicillin-resistant Staphylococcus aureus (MRSA) strains. The following parameters were examined: MRSAMupS and MRSAMupRL susceptibility to EOCs (1,8-cineole, eugenol, carvacrol, linalool, (-)-menthone, linalyl acetate, and trans-anethole), the bacterial cell size distribution, and chemical composition by the use of Fourier Transform Infrared Spectroscopy (FTIR) and Raman spectroscopies. The MRSAMupS and MRSAMupRL strains were susceptible to all tested EOCs. 1,8-cineole and (-)-menthone showed synergistic activity against MRSAMupS in combination with mupirocin, whereas 1,8-cineole exhibited synergistic activity against MRSAMupRL as well. In-depth analysis showed that both MRSAMupS and MRSAMupRL displayed similar distributions of the bacterial cell size. The FTIR and Raman spectra of the MRSAMupS and MRSAMupRL strains showed differences in some regions. New bands in the MRSAMupRL Raman spectrum were observed. It was concluded that the use of 1,8-cineole in combination with mupirocin can increase the mupirocin activity against the MRSAMupS and MRSAMupRL strains.

Large quantities of blackberry seeds are produced as a pomace during the processing of juice and jam production; this by-product is a very interesting raw material both for oil manufacturing and as a source of bioactive compounds. In this work the composition, yield and antioxidant activity of three types of Rubus fructicosus pomace extracts isolated by liquid extraction using solvents of different polarity, as well with supercritical COThe highest extract yield was reported for Soxhlet extraction using ethanol as a solvent (14.2%). Supercritical carbon dioxide and hexane extracts were characterised by the highest content of phytosterols (1445 and 1583 mg 100 gAll pomace extracts examined were of high quality, rich in essential omega fatty acids and with a very high content of bioactive compounds, such as phytosterols and tocopherols. The high nutritional value of extracts from berry seed pomace could justify the commercialisation of specific extracts not only as food additives but also as cosmetic components. © 2017 Society of Chemical Industry.

Ten enantiomerically pure hydroindene-derived compounds obtained by the transformation of (+)-carotol, the main constituent of carrot seed essential oil, were examined for their ability to inhibit the growth of myeloid leukaemia (HL-60) cancer cell lines. All compounds showed significant activity, which was comparable to the most active volatile organic compounds, such as trans–trans-farnesol, citral and nerolidol. Based on the bioactivity and molecular modelling, a 3D QSAR pharmacophore model was generated.

In the hexane extract of C. palustre and C. rivulare fruits, fatty acids, sterols, triterpenes, and volatile compounds were analyzed by the GC-MS-FID method. In the methanolic extracts, total phenol content was estimated. The antioxidant activity of both extracts was measured with DPPH assay and expressed in % scavenged DPPH.

The chemical composition, including the enantiomeric excess of the main terpenes, the antimicrobial and antiradical activities, as well as the cytotoxicity of Abies alba and A. koreana seed and cone essential oils were investigated. Additionally, their seed hydrolates were characterized. In the examined oils and hydrolates, a total of 174 compounds were identified, which comprised 95.6-99.9% of the volatiles. The essential oils were mainly composed of monoterpene hydrocarbons, whereas the composition of the hydrolates, differing from the seed oils of the corresponding fir species, consisted mainly of oxygenated derivatives of sesquiterpenes. The seed and cone essential oils of both firs exhibited DPPH-radical-scavenging properties and low antibacterial activity against the bacterial strains tested. Moreover, they evoked only low cytotoxicity towards normal fibroblasts and the two cancer cell lines MCF-7 and MDA-MBA-231. At concentrations up to 50 μg/ml, all essential oils were safe in relation to normal fibroblasts. Although they induced cytotoxicity towards the cancer cells at concentrations slightly lower than those required for the inhibition of fibroblast proliferation, their influence on cancer cells was weak, with IC50 values similar to those observed towards normal fibroblasts.

The essential oils from seeds of nine Abies koreana specimens have been studied using GC-MS-FID and NMR methods, leading to the determination of 96 volatiles, which constituted over 99% of the oils. The hydrodistilled oils of fresh, resinous scent were isolated with yields in the range of 3.8-8.5%. The results showed that the essential oil of Korean fir seeds contained 70-95% monoterpenes and 1-20% oxygenated monoterpenes as the dominant groups. The numerous sesquiterpenes, diterpenes and their oxygenated derivatives constituted only 2-8% of the oil. The major component of the seed essential oil was limonene (4172 g/100g); the laevorotary form of this terpene predominated. A. koreana seeds seem to be a rich source of both essential oil and (-)-limonene, whose average enantiomeric excess was above 95%.

The composition of essential oil from Telekia speciosa leaves, flowers, roots, stems and in vitro regenerated shoots was studied by GC-MS-FID leading to the determination of 112 compounds. The qualitative composition of the essential oil from the examined plant material was similar, whereas quantities of individual components of the oils varied widely depending on the kind of plant material. The most striking differences were observed between the oils produced by aerial and underground parts of the intact plant, as well as between oils produced by in vitro grown shoots and leaves of the intact plant. The main volatiles of leaf essential oil were: (E,E)-famesol (21.2%) and (E)-nerolidol (17.9%), while isoalantolactone was the predominant component of the root (62.3%) and flower oils (23.0%). Numerous thymol derivatives were also found, among them 10-isobutyryloxy-8,9-epoxythymol isobutyrate, which was one of the main components found in the flower oil (20.5%) and that from the in vitro cultures (20.2%).

The chemical composition of Cirsium vulgare flower heads was examined. Petrol and chloroform extracts of this plant material were analyzed by GC-MS for the presence of fatty acids, phytosterols, and triterpenes. Diethyl ether, ethyl acetate, and butanol fractions of the methanolic extract were subjected to multistep chromatographic separations, and as a result, fourteen flavonoids were obtained (1–14). All compounds were isolated from this morphological part for the first time and eleven from the plant. Among the identified components were four aglycones, eight glycosides, and two glycoside esters, derivatives of apigenin, luteolin, kaemferol, and quercetin. One of them was a rarely occurring compound apigenin 7- O-β-(6″-butyl)-glucuronide) (14). Total flavonoid content and antioxidant activity were determined in the various fractions of methanolic extract.