Chemical Composition of Essential Oils from Rare and Endangered Species-Eryngium maritimum L. and E. alpinum L.

In the present study, the essential oils obtained by hydrodistillation of the organs of Eryngium maritimum and E. alpinum were analyzed by GC-FID-MS. The dominant constituents assessed in the essential oil of E. maritimum were germacrene D (45.2%) in the fruits; hexadecanoic acid (18.5%), menthol (16.8%), and menthone (10.9%) in the roots; 2,3,4-trimethylbenzaldehyde (11.3%) and germacrene D (10.5%) in the leaves; 2,3,4-trimethylbenzaldehyde (11.3%) in the shoot culture. In the case of E. alpinum, the main components of the leaf oil were: ß-elemenone (10.3%), germacrone (5.8%), two selinadienes (7.1% and 6.7%), and 1,8-cineole (5.3%), which were not found in the oil from shoot culture, whereas the shoot culture oil was dominated by hexadecanoic acid (15.5%), spathulenol (7.5%), (E)-ß-farnesene (4.9%), germacra-4(15),5,10(14)-trien-1α-ol (4.7%), and falcarinol (4.3%). The essential oils obtained from E. maritimum fruits and leaves of the intact plants, measured by the broth microdilution method, were the most active against T. mentagophytes and S. aureus. Moreover, the essential oil of leaves had the moderate activity against C. albicans and E. coli. The results showed that the chemical compositions of the essential oils differed decidedly between the two studied species and between the organs. Furthermore, the essential oil of E. maritimum may play an important role as antimicrobial agent.

Agrobiological Interactions of Essential Oils of Two Menthol Mints: Mentha piperita and Mentha arvensis.

This review article discusses the active constituents and potential of two menthol mint oils, Mentha piperita (MPEO) and Mentha arvensis (MAEO), as natural sources for botanical pesticides. The biological activities of these menthol mint oils, which can be useful in agriculture, have been broadly researched, especially toward phytotoxic microorganisms. To a lesser extent, the insecticidal and herbicidal activities of mint EOs have also been studied. It is apparent that the prospect of using menthol mint oils in agriculture is increasing in popularity. A number of investigations showed that the in vitro efficacy of MPEO and MAEO, as well as that of their main constituent, menthol, is pronounced. The results of in vitro research are useful for choosing EOs for further investigations. However, it is clear that in situ experiments are crucial and should be more extensively developed. At the same time, known techniques are to be applied to this area and new methods should be worked out, aiming at the improvement of EOs' pesticidal efficacy and cost-effectiveness, for future implementation in agricultural pest control.

Potential Phytotoxic Effect of Essential Oil of Non-Native Species Impatiens parviflora DC.

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-α-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.

Phytotoxic Effect of Invasive Heracleum mantegazzianum Essential Oil on Dicot and Monocot Species.

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.

Antibacterial, Anti-Inflammatory, Antioxidant, and Antiproliferative Properties of Essential Oils from Hairy and Normal Roots of Leonurus sibiricus L. and Their Chemical Composition.

Essential oils obtained from the NR (normal roots) and HR (hairy roots) of the medicinal plant Leonurus sibiricus root were used in this study. The essential oil compositions were detected by GC-MS. Eighty-five components were identified in total. Seventy components were identified for NR essential oil. The major constituents in NR essential oil were ß-selinene (9.9%), selina-4,7-diene (9.7%), (E)-ß-caryophyllene (7.3%),myli-4(15)-ene (6.4%), and guaia-1(10),11-diene (5.9%). Sixty-seven components were identified in HR essential oil, the main constituents being (E)-ß-caryophyllene (22.6%), and germacrene D (19.8%). The essential oils were tested for cytotoxic effect, antimicrobial, anti-inflammatory, and antioxidant activities. Both essential oils showed activity against grade IV glioma cell lines (IC50 = 400 µg/mL), antimicrobial (MIC and MFC values of 2500 to 125 µg/mL), and anti-inflammatory (decreased level of IL-1ß, IL-6, TNF-α, and IFN-γ in LPS-stimulated cells).The essential oils exhibited moderate antioxidant activity in ABTS (EC50 = 98 and 88 µg/mL) assay. This is the first study to examine composition of the essential oils and their antimicrobial, antioxidant, antiproliferative, and anti-inflammatory activities. The results indicate that essential oils form L. sibiricus root may be used in future as an alternative to synthetic antimicrobial agents with potential application in the food and pharmaceutical industries.

Comparison of the Essential Oil Composition of Selected Impatiens Species and Its Antioxidant Activities.

The present paper describes the chemical composition of the essential oils obtained by hydrodistillation from four Impatiens species, Impatiens glandulifera Royle, I. parviflora DC., I. balsamina L. and I. noli-tangere L. The GC and GC-MS methods resulted in identification of 226 volatile compounds comprising from 61.7%-88.2% of the total amount. The essential oils differed significantly in their composition. Fifteen compounds were shared among the essential oils of all investigated Impatiens species. The majority of these constituents was linalool (0.7%-15.1%), hexanal (0.2%-5.3%) and benzaldehyde (0.1%-10.2%). Moreover, the antioxidant activity of the essential oils was investigated using different methods. The chemical composition of the essential oils and its antioxidant evaluation are reported for the first time from the investigated taxon.

Microencapsulation of Nigella sativa oleoresin by spray drying for food and nutraceutical applications.

Oleoresin of Nigella sativa L. (Black cumin) was obtained from the seeds using hexane extraction at room temperature. The oleoresin was emulsified in an aqueous solution containing gum Arabic/maltodextrin (1:1 w/w) and then encapsulated in powder form by spray drying. The characteristics of the obtained powder including moisture content, bulk density, wettability, morphology, encapsulation efficiency were evaluated. The effect of the spray drying on the chemical composition of the volatile oil fraction of N. sativa oleoresin was also evaluated using gas chromatographic-mass spectroscopic analysis. Results indicated that the encapsulation efficiency of the whole oleoresin in the powder can range from 84.2±1.5% to 96.2±0.2% depending on the conditions of extracting the surface oil from the powder. On the other hand the encapsulation efficiency of the volatile oil fraction was 86.2% ±4.7. The formulated N. sativa L. oleoresin powder can be used in the fortification of processed food and nutraceuticals.

The Essential Oils of Rhaponticum carthamoides Hairy Roots and Roots of Soil-Grown Plants: Chemical Composition and Antimicrobial, Anti-Inflammatory, and Antioxidant Activities.

The essential oils were isolated by hydrodistillation from the hairy roots (HR) and roots of soil-grown plants (SGR) of Rhaponticum carthamoides and were analyzed by GC-MS method. In the both essential oils 62 compounds were identified. The root essential oils showed the differences in the qualitative and quantitative composition. The sesquiterpene hydrocarbons (55-62%) dominated in both essential oils. The major compounds of HR essential oil were cyperene, 13-norcypera-1(5),11(12)-diene, and cadalene while aplotaxene, nardosina-1(10),11-diene, and dauca-4(11),8-diene dominated in SGR essential oil. Both essential oils showed antibacterial activity especially against Enterococcus faecalis (ATCC 29212) and Pseudomonas aeruginosa (ATCC 27853) (MIC value = 125 µg/mL). HR and SGR essential oils also decreased the expression of IL-1ß, IL-6, and TNF-α and the ROS level in LPS-treatment astrocytes. This is the first report to describe the chemical composition of R. carthamoides essential oil from hairy roots, its protective effect against LPS-induced inflammation and ROS production in astrocytes, and its antimicrobial potential. The results show that R. carthamoides hairy roots may be a valuable source of the essential oil and may be an alternative to the roots of soil-grown plants.

Antimicrobial activity of geranium oil against clinical strains of Staphylococcus aureus.

The aim of this work was to investigate the antibacterial properties of geranium oil obtained from Pelargonium graveolens Ait. (family Geraniaceae), against one standard S. aureus strain ATCC 433000 and seventy clinical S. aureus strains. The agar dilution method was used for assessment of bacterial growth inhibition at various concentrations of geranium oil. Susceptibility testing of the clinical strains to antibiotics was carried out using the disk-diffusion and E-test methods. The results of our experiment showed that the oil from P. graveolens has strong activity against all of the clinical S. aureus isolates-including multidrug resistant strains, MRSA strains and MLS(B)-positive strains-exhibiting MIC values of 0.25-2.50 µL/mL.

The effects of thyme (Thymus vulgaris) and rosemary (Rosmarinus officinalis) essential oils on Brochothrix thermosphacta and on the shelf life of beef packaged in high-oxygen modified atmosphere.

The objective of the study was to determine the Minimal Inhibitory Concentration (MIC) of thyme (29.4% thymol, 21.6% p-cymene) and rosemary essential oils (27.6% 1,8-cineole, 13.5% limonene, 13.0% ß-pinene) against Brochothrix thermosphacta and to establish the feasibility of their use as components of modified atmosphere during beef refrigerated storage. The minimum inhibitory concentration (MIC) of thyme oil against B. thermosphacta is 0.05% and that of rosemary oil 0.5%. The MIC values are independent on strain and temperature of growth, however the bactericidal effects are strain dependent. The addition of any of oil at a concentration equal to 2MIC to the modified atmosphere (80% O(2)/20% CO(2)) does not significantly influence the microbial quality of meat. At the same time, such a concentration of the essential oils was considerably detrimental to the organoleptic factors.

Chemical composition of essential oils from a multiple shoot culture of Telekia speciosa and different plant organs.

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 the essential oils of Cirsium palustre and C. rivulare and their antiproliferative effect.

The composition of the essential oils of Cirsium palustre and C. rivulare and their antiproliferative activity against breast adenocarcinoma cells (MCF-7 and MDA-MBA-231) were investigated. The essential oils obtained by hydro-distillation from the roots (yield 0.2 and 0.1% v/w, respectively), leaves and inflorescences (yield below 0.01%), were analyzed by gas chromatography coupled with mass spectrometry (GC-MS). The composition of the essential oils in the respective organs of each plant differed considerably. On the other hand, similarities were observed in the composition of root and leaf oils. In C. palustre and C. rivulare root oil, 50 and 39 constituents were identified, accounting for 95.3% and 92.4% of the total content. The main components were aplotaxene and its derivatives, representing 78.6% and 46.6% of the total content. In leaf oils of both species, 59 and 49 compounds, respectively, were identified, representing 67.4% and 78.3% of the total content. The major constituents were beta-damascenone (4.1% and 13.4%, respectively) and beta-ionone (6.7% and 5.3%, respectively). Short-chain saturated and unsaturated aliphatic alcohols and aldehydes constituted another important group of compounds (17.7% and 9.0%, respectively). The essential oils of the roots have moderate anti-proliferative activity, with IC50 values ranging from 110 to 140 microg/mL. These concentrations were below the level able to inhibit the proliferation of healthy cells.

[Sensitivity assessment of thyme and lavender essential oils against clinical strains of Escherichia coli for their resistance]. / Ocena wrazliwosci klinicznych szczepów Escherichia coli na dzialanie olejku tymiankowego i lawendowego w odniesieniu do ich lekoopornosci.

Strong antiseptic activity of plant essential oils and extracts has been known for a long time. The antibacterial activity of thyme and lavender essential oils were tested against 30 clinical bacterial strains of Escherichia coli from patients with different clinical conditions. The agar diffusion method was used for microbial growth inhibition at various concentrations of the oils from Thymus vulgaris and Lavandula angustifolia. Susceptibility testing to antibiotics and chemotherapeutics was carried out using disc-diffusion method. The results of experiments showed that the both oils, from T. vulgaris and L. angustifolia were active against all of the clinical strains, but thyme oil demonstrated the highest activity. Thyme and lavender essential oils were active against multi drug resistant clinical strains of Escherichia coli genera. The results of experiments justify a study related to activity other essential oils against different genus of bacteria.

Antibiofilm activity of selected plant essential oils and their major components.

The aim of the study was to examine the antibiofilm activity of selected essential oils (EO): Lavandula angustifblia (LEO), Melaleuca alternifolia (TTO), Melissa officinalis (MEO) and some of their major constituents: linalool, linalyl acetate, alpha-terpineol, terpinen-4-ol. Biofilms were formed by Staphylococcus aureus ATCC 29213 and Escherichia coli NCTC 8196 on the surface of medical biomaterials (urinary catheter, infusion tube and surgical mesh). TTC reduction assay was used for the evaluation of mature biofilm eradication from these surfaces. Moreover, time-dependent eradication ofbiofilms preformed in polystyrene 96-well culture microplates was examined and expressed as minimal biofilm eradication concentration (evaluated by MTT reduction assay). TTO, alpha-terpineol and terpinen-4-ol as well as MEO, showed stronger anti-biofilm activity than LEO and linalool or linalyl acetate. Among the biomaterials tested, surgical mesh was the surface most prone to persistent colonization since biofilms formed on it, both by S. aureus and E. coli, were difficult to destroy. The killing rate studies of S. aureus biofilm treated with TTO, LEO, MEO and some of their constituents revealed that partial (50%) destruction of 24-h-old biofilms (MBEC50) was achieved by the concentration 4-8 x MIC after 1 h, whereas 2-4 x MIC was enough to obtain 90% reduction in biomass metabolic activity (MBEC90) after just 4 h of treatment. A similar dose-dependent effect was observed for E. coli biofilm which, however, was more susceptible to the action of phytochemicals than the biofilms of S. aureus. It is noteworthy that an evident decrease in biofilm cells metabolic activity does not always lead to their total destruction and eradication.

Composition of the essential oil of Bidens tripartita L. roots and its antibacterial and antifungal activities.

The chemical composition of the essential oil obtained from the roots of Bidens tripartita L. by hydrodistillation was investigated by gas chromatography-mass spectrometry. In total, 106 compounds were identified (97.1% of the total oil). The main components of the oil were α-pinene (15.0%), ß-bisabolene (9.3%), p-cymene (6.0%), hexanal (5.7%), linalool (4.6%), p-cymene-9-ol (3.4%), ß-elemene (2.6%), 2-pentylfuran (2.2%), and silphiperfol-6-ene (2.1%). The antibacterial and antifungal properties of the essential oil were evaluated against eight Gram-positive and 11 Gram-negative bacterial species and 10 fungal strains. The oil exhibited a strong antifungal activity.

Essential Oil Composition of the Different Parts and In Vitro Shoot Culture of Eryngium planum L.

The essential oils obtained by hydrodistillation from the different parts (inflorescence, stalk leaves, rosette leaves and root) as well as from in vitro shoot culture of Eryngium planum L. were analyzed by GC-FID-MS in respect to their chemical composition. The different parts of E. planum and in vitro shoots showed different yields. The part with higher amount was the inflorescences, followed by the stalk leaves and in vitro shoots, rosette leaves and finally roots. The essential oils obtained from rosette leaves and in vitro-derived rosettes had totally different composition. Quantitative differences were also found between compounds of intact plant organs. The main components of stalk leaf oil and rosette leaf oil were monoterpene (limonene, α- and ß-pinene) and sesquiterpene hydrocarbons. In inflorescence oil cis-chrysanthenyl acetate (43.2%) was accompanied by other esters (propionate, butanoate, hexanoate and octanoate) and numerous oxygenated sesquiterpenes. Root oil and in vitro shoot oil contained mainly (Z)-falcarinol and 2,3,4-trimethylbenzaldehyde. This is the first report on the chemical composition of this species.

Different isolation methods for determination of composition of volatiles from Nigella damascena L. seeds.

Volatile organic compounds (VOCs) from seeds of Nigella damascena L. were isolated using different techniques. The yield, as well as the qualitative and quantitative composition of the oils, was strongly influenced by the isolation method. In the hydrodistilled essential oil, the major components were the sesquiterpene hydrocarbons beta-elemene (59.1%), beta-selinene (12.8%) and alpha-selinene (12.6%). Conventional solvent extraction, followed by hydrodistillation, resulted in a volatile oil with a different composition than that of the hydrodistilled oil. The extracted oils predominantly contained sesquiterpene hydrocarbons, but also methyl anthranilate derivatives. By means of HS-SPME, it was possible to analyze not only sesquiterpenes and anthranilates, but also monoterpenes and the most volatile compounds, for example, the lower fatty acid (butyric, capronic) esters, which determine the characteristic sweet scent of N. damascena seeds. Using all testing methods, 55 compounds were identified, 40 of which are new for N. damascena seed VOCs.

Chemical composition of the essential oils from the roots of Erigeron acris L. and Erigeron annuus (L.) Pers.

The chemical compositions of essential oils from the roots of Erigeron acris and Erigeron annuus were studied. The essential oils were obtained by hydrodistillation in 1.0% and 0.05% yield, respectively, and analyzed by GC, GC-MS. Fifty four and forty seven constituents were identified. Predominant constituents of both oils were poly-acetylene esters: (Z,Z)-matricaria ester (49.4% and 45.9%, respectively) and (Z)-lachnophyllum ester (37.2% and 27.5%, respectively), that were accompanied by their stereoisomers as well as appropriate lactones. Polyacetylenic compounds amounted to 92.1% of E. acris oil and 85.8% of E. annuus oil. Both oils contained the same monoterpene hydrocarbons, amounting to 4.2% and 5.8%, respectively, and traces of almost the same monoterpene oxygenated compounds. The dominant sesquiterpenes in E. acris were elemenes and tricyclic sesquiterpene hydrocarbons, while in E. annuus beta-sesquiphellandrene and beta-bisabolene dominated. After flash chromatography of essential oil from E. acris, fractions contained acetylene esters and acetylene lactones were obtained. The configuration about double bonds for these compounds has been elucidated on the basis of (1)H- and (13)C-NMR analysis.

Chemical composition and biological activities of essential oil from Salvia sclarea plants regenerated in vitro.

The essential oils obtained by hydrodistillation of dried aerial parts of Salvia sclarea L. plants, regenerated in vitro and reproduced from seeds, were analyzed by GC and GC-MS. The oils from in vitro and in vivo plants were compared in respect to their chemical composition as well as antimicrobial and cytotoxic activities. The chemical profiles of both oils were very similar, although the yield of essential oil from in vitro plants was lower (0.1%, v/w) than the oil yield isolated from in vivo S. sclarea plants (0.2%, v/w). Both oils showed antimicrobial and cytotoxic activity. The oil from in vitro regenerated plants of S. sclarea exhibited stronger cytotoxic action against NALM-6 cell lines in comparison with the essential oil from in vivo plants.

[The optimization of methods utilized for testing the antibacterial activity of essential oils]. / Weryfikacja metodycznych parametrów oznaczania przeciwbakteryjnej aktywnosci olejków eterycznych.

The antibacterial activity of essential oils: Lavandulae aetherleum, Limonis aetherleum and Melaleucae aetherleum was determined against Staphylococcus aureus Gram (+) and Escherichia coli Gram (-) bacteria, using four methods: agar diffusion (paper disk and agar wells) and broth dilution (turbidimetric and rezazurin reduction assay). This study revealed that the sensitivity of the agar diffusion techniques was much lower than the broth dilution methods. This was mainly due to partitioning of the oil components in the agar according to their affinity with water. This limitation could be lessened by the selection of suitable oil emulsifier/solvent, which itself not influence the bacterial growth. By initial oil solubilization with 96% ethanol (1:1), the increase of agar dilution methods sensitivity could be achieved. The broth microdilution methods, using 0.5% Tween 20 or 0.15% agar to emulsify the oils, were optimized and shown to be most accurate for testing their antimicrobial activity. By introducing resazurin, as an MIC endpoint indicator, the sensitivity of these methods was further enhanced.