Analysis of the essential oil of Teucrium polium ssp. capitatum from the Balkan Peninsula

The chemical composition of the essential oil of the aerial parts of Teucrium polium ssp. capitatum collected during the flowering period from rocky places and dry pastures, (Serbia, Nis, Kamenica), and dunes along the sea-side, (Bulgaria, Burgas, Primorsko) has been studied by GC and GC/MS. The identified compounds, 45 for the oil from Serbia and 44 for that from Bulgaria, amounted to 97.3% and 96.4% of the oils, respectively. The dominant constituents of the Serbian oil were sesquiterpenes {59.6%, the most abundant components being germacrene D (31.8%), trans-caryophyllene (8.8%) and bicyclogermacrene (6.2%)}, while monoterpenes accounted for 37.5% {the most abundant components being linalool (14.0%) and beta-pinene (10.7%)}. The essential oil from Bulgaria was characterized by a high percentage of monoterpenes, amounting to 62.9% {the most abundant components being beta-pinene (26.8%), alpha-pinene (9.3%) and limonene (6.4%)}, while sesquiterpenes accounted for 33.5% (the most abundant component was germacrene D 17.7%)}.     

气相色谱/质谱法分析柏树叶挥发油的化学成分

采用水蒸气蒸馏技术提取了3种柏树叶的挥发油,经气相色谱/质谱分析,共分离和鉴定了64种化学成分,其主要成分为萜烯类,其他成分为烷烃类、醇类、酚类和酯类等。其中圆柏树叶中分离鉴定出33种挥发性成分,主要萜类为桧烯(20.99%)和柠檬烯(19.78%);中山柏树叶中分离鉴定出37种挥发性成分,主要为α-蒎烯(10.39%)、桧烯(11.19%)和δ-3-蒈烯(8.88%);龙柏树叶中分离鉴定出37种挥发性成分,主要为柠檬烯(24.56%)和β-月桂烯(8.04%)。分离鉴定出3种柏树叶的共有成分14种。     

Composition and antimicrobial activity of Seseli montanum subsp. tommasinii essential oil

The essential oil isolated from Seseli montanum L. subsp. tommasinii Reich. f. was analyzed by GC/MS and the most abundant components were beta-pinene (30.2%), germacrene D (10.1%), sabinene (8.0%), alpha-pinene (7.2%) and limonene (6.6%). The antimicrobial effect of the essential oil was evaluated against four bacterial and four fungal species among which were food contaminants, spoilage fungi, and plant, fungal and animal pathogens. The oil possessed moderate to strong antimicrobial activity.     

OH-initiated oxidation of monoterpenes: reaction of alpha-pinene

The aim of this paper is to study the reaction products of alpha-pinene, beta-pinene, limonene, 3-carene and sabinene with OH radicals by FT-IR spectroscopy and by HPLC-MS-MS, to evaluate the secondary aerosol formation. All gas phase reaction products were quantified using reference compounds. As source of OH radicals were used H2O2 and CH3ONO. The experiments were performed at low terpene concentration (0.9-2.1 ppm) and at high terpene concentration (4.1-13.2 ppm), using H2O2 and CH3ONO as sources of OH radicals.     

Antibacterial activity and comparison of the volatile constituents obtained by several extraction methods from the flowers, stems and leaves of Astrodaucus orientalis

The oils of the flowers, stems and leaves of Astrodaucus orientalis L. were separately extracted using hydrodistillation (HD), head-space solid-phase microextraction (HS-SPME) and microwave assisted head-space solid-phase microextraction (MA-HS-SPME). The volatile constituents were analyzed by GC and GC/MS. Temperature and time of extraction, microwave power and exposure time of extraction were optimized. Polydimethylsiloxane (PDMS) fiber was used as the solid phase for SPME methods. The main constituents of the flower, stem and leaf oils isolated by HD, HS-SPME and MA-HS-SPME are as follows, respectively: beta-pinene (20.5%, 13.9% and 30.4%), alpha-thujene (8.7%, 16.2% and 10.9%) and alpha-pinene (7.6%, 14.3% and 10.9%) for the flowers, sabinene (11.8%, 32.3% and 11.8%), alpha-pinene (8.7%, 28.8% and 6.1%) and p-mycrene (2.5%, 12% and 8.5%) for the stem, and alpha-pinene (9.4%, 37.1% and 22.5%), sabinene (13.5%, 26.3% and 23.5%), beta-pinene (6.3%, 9.8% and 10%) and p-mycrene (3.2%, 2.5% and 15.6%) for the leaf. The minimum inhibitory concentrations (MIC) were determined for all essential oils obtained by HD against both Gram-positive (Bacillus subtilis) and Gram-negative (Escherichia coli) bacteria using the agar dilution method. These oils showed the good activities against the both bacteria (0.5 - 1.5 mg/mL).     

Chemical composition and phytotoxic effects of essential oils from four Teucrium species

The essential oils of four Teucrium species were studied and 131 components, in all, were identified. All oils were rich in sesquiterpenes (50.0-61.9%). Caryophyllene and caryophyllene oxide were the main components of Teucrium arduini; germacrene D, delta-cadinene and gamma-cadinene predominated in Teucrium maghrebinum. Carvacrol and caryophyllene predominated in Teucrium polium ssp. capitatum, while carvacrol, caryophyllene oxide and caryophyllene were the most abundant components in Teucrium montbretii ssp. heliotropiifolium. The germination of radish and garden cress was less sensitive to the four essential oils. The radicle elongation, above all, of radish was significantly inhibited by all oils, in particular by the essential oil of T. arduini, at the highest doses tested. Among the main components of the oils, monoterpenes resulted the more active compounds.     

Chemical polymorphism of essential oils from populations of Laurus nobilis grown on Tunisia, Algeria and France

The compositions of the essential oils isolated from the aerial parts of tree Mediterranean populations of Laurus nobilis L. collected during the flowering phase on Tunisia, Algeria and France, were studied by GC and GC-MS. The analysis has allowed identifying 54 components. The main components were 1,8-cineole, alpha-terpinyl acetate (10-18.6%), methyl eugenol (10-22.1%), sabinene (1.2-8%), eugenol (1.2-11.7%) alpha-pinene (tr-4.5%) and beta-pinene (0.4-4.2%). The monoterpene fraction was dominant in all the oils analysed and consisted mainly of oxygenated monoterpenes. The oils from the tree populations studied showed a clear chemical polymorphism. The principal component and the hierarchical cluster analyses separated the Laurus nobilis leaf essential oils into three groups.     

Leaf essential oil of Manekia naranjoana (Piperaceae) from Costa Rica and its cytotoxic activity

The chemical composition of the leaf oil of Manekia naranjoana (C. DC.) Callejas (Piperaceae) from Costa Rica was analyzed by capillary GC/FID and GC/MS. Fifty-five compounds were identified. Major compounds from the leaf oil were beta-pinene (30.6%), alpha-pinene (18.8%), limonene (13.7%), and beta-caryophyllene (6.1%). The oil presented very low toxicity to tumor and non-tumor cell lines, even though it contains components, such as alpha- and beta-pinene, limonene and others, which have been shown to be cytotoxic. This is the first report of the chemical composition of the essential oil obtained from this species.     

GC/MS analysis and antimicrobial activity of the essential oil of fresh leaves of Eucalytus globulus, and leaves and stems of Smyrnium olusatrum from Constantine (Algeria)

The essential oils of fresh leaves of Eucalyptus globulus L. (Myrtaceae), and leaves and stems of Smyrnium olusatrum L. (Apiaceae), obtained by hydrodistillation in a Clevenger-type apparatus, were analyzed by GC/MS. Twenty compounds were characterized, representing 98.3% of the essential oil of E. globulus, with 1,8-cineole (48.6%), globulol (10.9%), trans-pinocarveol (10.7%), and alpha-terpineol (6.6%) as main components, while thirty-three compounds were characterized, representing 94.3% of the essential oil of S. olusatrum, with sabinene (27.1%), curzerene (13.7%), methyl-1-benzyl-2-oxocyclooctane carboxylate (12.3%), alpha-pinene (7.2%), cryptone (7.1%) and beta-pinene (5.7%) as the major components. The essential oils of E. globulus and S. olusatrum were tested against a wide range of fungal and bacterial strains. Both oils showed significant antimicrobial activity.     

Determination of Teucrium chamaedrys volatiles by using direct thermal desorption-comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry

The direct qualification and quantification of the volatile components of Teucrium chamaedrys was studied using a direct thermal desorption (DTD) technique with comprehensive two-dimensional (2D) gas chromatography-time-of-flight mass spectrometry (GC x GC-TOF/MS). The GC x GC separation chromatographically resolved hundreds of components within this sample, and with the separation coupled with TOF/MS for detection, high probability identifications were made for 68 compounds. The quantitative results were determined through the use of internal standards and the desorption of differing amounts of raw material in the injector. The highest yield of volatile compounds (0.39%, w/w) was obtained at 150 degrees C thermal desorption temperature using 1.0mg of dried sample placed in a glass injector liner when studied over the range 1.0-7.0mg. Lowest yield of 0.33% (w/w) was found for the largest sample size of 7.0mg. Relative standard deviation (RSD) for 10 replicates at each size sample were in the range 3.9-21.6%. The major compounds identified were beta-pinene, germacrene D, alpha-pinene, alpha-farnesene, alpha-gurjunene, gamma-elemene and gamma-cadinene. All identified compounds were quantified using total ion chromatogram (TIC) peak areas. DTD is a promising method for quantitative analysis of complex mixtures, and in particular for quantitative analysis of plant samples, which can yield data without the traditional obligation for costly and time-consuming extraction techniques.     

The essential oil of Artemisia scoparia from tajikistan is dominated by phenyldiacetylenes

The essential oil from the aerial parts of Artemisia scoparia was obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry. A total of 32 compounds were identified representing 98.0% of the total oil composition. A. scoparia oil was dominated by the diacetylenes 1-phenyl-2,4-pentadiyne (34.2%) and capillene (4.9%). Other major components were beta-pinene (21.3%), methyl eugenol (5.5%), alpha-pinene (5.4%), myrcene (5.2%), limonene (5.0%), and (E)-beta-ocimene (3.8%). The oil was tested for in-vitro cytotoxic activity against MCF-7 cells, but was inactive.     

Structural elucidation of monoterpene oxidation products by ion trap fragmentation using on-line atmospheric pressure chemical ionisation mass spectrometry in the negative ion mode.

Based on ion trap mass spectrometry, an on-line method is described which provides valuable information on the molecular composition of structurally complex organic aerosols. The investigated aerosols were generated from the gas-phase ozonolysis of various C(10)H(16)-terpenes (alpha-pinene, beta-pinene, 3-carene, sabinene, limonene), and directly introduced into the ion source of the mass spectrometer. Negative ion chemical ionisation at atmospheric pressure (APCI(-)) enabled the detection of multifunctional carboxylic acid products by combining inherent sensitivity and molecular weight information. Sequential low-energy collision-induced product ion fragmentation experiments (MS(n)) were performed in order to elucidate characteristic decomposition pathways of the compounds. Dicarboxylic acids, oxocarboxylic acids and hydroxyketocarboxylic acid products could be clearly distinguished by multistage on-line MS. Furthermore, sabinonic acid and two C(9)-ether compounds were tentatively identified for the first time by applying on-line APCI(-)-MS(n).     

Oil constituents of Artemisia nilagirica var. septentrionalis growing at different altitudes

Oils of Artemisia nilagirica var. septentrionalis plants growing at different altitudes in Himachal Pradesh, India were hydro-distilled and analyzed by GC-GC/MS. The major constituents of the oil show variation with changes in altitude. At lower, middle and higher altitudes, the major constituents of the oil were caryophyllene oxide (28.6%), borneol (35.8%) and camphor (46.9%), respectively. The percentages of alpha-humulene and trans-beta-guaiene also increased, but the percentage of sabinene, trans-sabinene hydrate, 4-terpineol, caryophyllene oxide and humulene epoxide-II decreased with an increase in altitude. The characteristic compounds observed in the plants from lower altitudes were 2-hexene-1-ol, beta-thujone, thujanol, myrtenol and linalyl acetate, while the higher altitude plants were characterized by the presence of alpha-pinene, beta-pinene, limonene, linalool, gamma-gurijunene, germacrene-D and farnesol.     

Headspace solid-phase microextraction for characterization of fragrances of lemon verbena (Aloysia triphylla) by gas chromatography-mass spectrometry

Natural fragrances from lemon verbena (Aloysia triphylla) were studied by headspace solid phase microextraction (HS-SPME) techniques followed by gas chromatography-mass spectrometry (GC-MS), with six different fibre coatings being tested to evaluate the extraction efficiencies of several selected compounds. A total of 14 compounds were identified in the fragrances of lemon verbena. Geranial and neral were detected as major components and alpha-pinene, beta-pinene, beta-caryophyllene, and curcumene as minor components. Enantiomeric analysis of chiral compounds from lemon verbena was carried out on a chiral column. alpha-Pinene, limonene, and camphor in the fragrances emitted from lemon verbena were found in the (+), (-), and (-) forms, respectively.     

Analysis by gas chromatography-mass spectrometry of the essential oils from the aerial parts of Rutheopsis herbanica (Bolle) Hans. & Kunk., gathered in Fuerteventura (Canary Islands)

The essential oil from the aerial parts of Rutheopsis herbanica (Bolle) Hans. & Kunk., growing in Fuerteventura, Canary Islands, Spain, was studied by gas chromatography and gas chromatography-mass spectrometry, and 42 constituents were identified. The major components were found to be alpha-pinene (29.4%), dillapiole (21.3%), limonene (14.1%), beta-pinene (13.2%) and myristicin (10.0%). As far as we know, this is the first report on the essential oil composition of this species.     

Microdistillation and analysis of volatiles from eight ornamental Salvia taxa

Volatile compounds from seven Salvia species and one interspecific hybrid growing at the Dallas Arboretum and Botanical Garden, Texas, US. Salvia coccinea, S. farinacea, S. greggii, S. leucantha, S. longispicata x farinacea, S. madrensis, S. roemeriana and S. splendens were investigated for their chemical compositions using a microdistillation technique. Volatiles were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC/MS). One hundred and twenty seven compounds were identified representing 94.3-99.7% of the oils. The major components in each of the seven species were as follows: S. coccinea (Z)-3-hexenal (31%), viridiflorol (19%); S. farinacea 1-octen-3-ol (30%) and (Z)-3-hexenal (23%); S. greggii 1,8-cineole (22%), borneol (17%), camphene (11%) and alpha-pinene (10%); S. leucantha limonene (35%) and alpha-pinene (17%); S. longispicata x farinacea 1-octen-3-ol (50%) and (Z)-3-hexenal (24%); S. madrensis (Z)-3-hexenal (53%); S. roemeriana limonene (49%) and alpha-pinene (20%); and S. splendens (Z)-3-hexenal (36%), 2,5-dimethoxy-p-cymene (19%) and linalool (11%). The microdistillation method was fast, practical and a useful technique that enabled the isolation of the volatiles in samples when only limited quantities were available.     

Volatile constituents of Senecio pterophorus (African daisy) DC. from South Africa

The hydrodistilled essential oils of the leaves of Senecio pterophorus collected from three different localities in KwaZulu-Natal Province, South Africa have been analyzed by GC and GC/MS. Thirteen - eighteen compounds were identified, accounting for over 98% of the total oil composition. The major components of the oils were limonene (10.3 - 32.3%), myrcene (14.4-19.7%), sabinene (13.0-18.0%), alpha-phellandrene (3.4-16.9%) and p-cymene (15.6-16.7%).     

Comparative analysis of some active principles of herb plants by GC/MS

A rapid extraction procedure for fingerprint chromatogram of different types of Mentha piperita L. (Labiatae family) is presented. The extracts were analysed by gas chromatography and gas chromatography-mass spectrometry (GC/MS). The main volatile compounds identified by the gas chromatography-mass spectrometric analysis of M. piperita L. were menthol, menthone, isomenthone, 1,8-cineole, menthyl acetate, limonene, beta-myrcene, carvone. M. piperita L. oil had the active principles: menthol, menthone, isomenthone, menthyl acetate, alpha-pinene, beta-pinene, champhor, limonene, linalool, piperitone. M. crispa L. showed carvone as major component.     

Chemical composition of the essential oil of Pelargonium quercetorum Agnew. of Iran

The volatile constituents in the essential oil of Pelargonium quercetorum Agnew., growing wild in Kurdistan, Iran were investigated through GC and GC/MS technique. Twenty-six compounds, representing 21 (80.77%) of the total oil were identified. The main components were: alpha-pinene (25.28%), alpha-fenchyl acetate (20.63%), limonene (9.94%), beta-caryophyllene (8.20%), camphene (4.31%), delta-cadinene (3.32%), beta-pinene (3.21%), alpha-amorphene (2.80%), valencene (2.73%), ledene (2.25%) and p-cymene (1.63%).     

Chemical composition of the essential oil of Pituranthos scoparius

The essential oils obtained by hydro distillation of the aerial parts of Pituranthos scoparius were collected from different regions of Algeria and gave various yields ranging from 0.6 up to 2.8% (v/w). These samples were analyzed by GC and GC-MS showing the occurrence of monoterpene hydrocarbons and some oxygenated compounds. The major components were alpha-pinene (4.4-35.8%), limonene (0.8-66.5%), bornyl acetate (tr-9.6%), myristicin (tr-31.1) and dill apiole (0.4-47.3%). The aerial parts of P. scoparius could be either very rich or very poor in limonene, myristicin or dill apiole. Cluster analysis shows differences in essential oil compositions of samples coming from the different area collected.