Application of multidimensional gas chromatography to the enantioselective characterisation of the essential oil of Eupatorium buniifolium Hooker et Arnott

The qualitative and quantitative composition of the essential oil from aerial parts of Eupatorium buniifolium Hooker et Arnott (Asteraceae) has been investigated for the first time. The essential oils were obtained by steam distillation of leaves and analysed by GC-MS; 44 components were identified. Monoterpene and sesquiterpene hydrocarbons, especially alpha-pinene (14.7%), beta-elemene (12.2%), germacrene D (11.5%), trans-beta-guaiene (6.5%) and (E)-caryophyllene (4.3%), were the major constituents found in the oils. The characterisation of E. buniifolium by enantioselective GC was performed by evaluation of the enantiomeric ratios of alpha-pinene, sabinene, beta-pinene, limonene, terpinen-4-ol and germacrene D.     

The inflorescence and leaf essential oils of Tanacetum vulgare L. var. vulgare growing wild in Lithuania

Forty samples of inflorescences and leaves of wild Tanacetum vulgare L. var. vulgare were collected in 20 habitats from Lithuania. The essential oils were analyzed by GC and GC/MS. The 57 identified compounds in the oils made up 80.7–99.6%. According to the cluster analysis the volatile oils were divided into four groups with 1,8-cineole (23.6–46.3%, 11 oils), trans-thujone (35.7–78.4%, 6 samples), camphor (19.8–61.8%, 17 oils) and myrtenol (13.1–24.9%, 6 samples) as main constituents. The inflorescences and leaves of tansy plants formed the oils with the same dominating constituent in 15 of the 20 habitats investigated. The leaves in five localities produced oils of the 1,8-cineole chemotype, while the inflorescences biosynthesized oils of the camphor type in three habitats and of the myrtenol type in two habitats. Amounts of the 1,8-cineole in all leaf oils were greater than that in inflorescence oils of the plants from the same locality. An opposite correlation was determined for camphor, myrtenol, cis- and trans-thujone. The myrtenol chemotype was not noticed earlier in the essential oils of T. vulgare.     

Composition of the volatile oils of two Anthemis L. taxa from Turkey

The essential oils of water-distilled aerial parts of Anthemis pseudocotula and Anthemis cretica subsp. pontica (Asteraceae) were analysed by GC-MS. As a result thirty-five and forty compounds were identified representing 93.1% and 89.0% of the oils, respectively. The main compounds of A. pseudocotula were 1,8-cineole (39.40%), camphor (9.36%), artemisiaketone (5.68%), filifolene (5.15%), and a-terpineol (4.69%), whereas beta-caryophyllene (20.26%), azulene (14.98%), spathulenol (6.03%), and germacrene D (5.82%) were the major constituents of A. cretica subsp. pontica.     

Essential oil from herb and rhizome of Peucedanum ostruthium (L. Koch.) ex DC

Essential oil from herb and rhizome of Peucedanum ostruthium (L.Koch.) ex DC underwent qualitative and quantitative analyses. The content of the oil obtained by hydrodistillation was 0.95% in the herb and 1.25% in the rhizome (per dry weight basis). Gas chromatography (GC) with MS detection and flame ionisation detection showed that the oil from the rhizome contains 39 compounds, of which 29 were identified. Gas chromatography with flame ionisation detection in chiral columns against standard compounds showed the presence of enantiomers of some of the components of the oil. Compounds present in largest quantities are: sabinene (35.2%) of which (+) sabinene accounts for (96.54%) and 4-terpineol (26.6%) of which (+) 4-terpineol accounts for (65.8%). 44 components were found in the herb essential oil, of which 39 compounds were identified. Compounds present in largest quantities were beta-caryophyllene (16.1%) and alpha-humulene (15.8%). The content of sabinene in the herb oil was 4.7%. The following compounds were present in the herb oil only as enantiomers: (+) sabinene (4.7%), (-) limonene (4.4%), (-) beta-pinene (0.4%). A coumarin (osthole) was detected in both essential oils (5.5% in herb oil and 5.1% in rhizome oil).     

Phytochemical diversity of Origanum vulgare L. subsp. vulgare (Lamiaceae) from Austria

This investigation was aiming at the phytochemical characterisation of Origanum vulgare subsp. vulgare from Austria. To study the qualitative and quantitative composition of essential oil compounds 374 individual plants were analysed via GC. The volatiles of Austrian O. vulgare subsp. vulgare were found to be complex mixtures of 53 mono- and sesquiterpenes. Among the sesquiterpenes β-caryophyllene, germacrene D, E-E-α-farnesene, germacrene D-4-ol and caryophyllene oxide were frequently present in higher amounts. The monoterpenes were mainly made up of sabinyl-compounds [mainly sabinene (up to 48.4%) and cis-sabinene hydrate (up to 57.8%)] and/or cymyl-compounds [mainly p-cymene (up to 49.7%), γ-terpinene (up to 21.5%) and carvacrol (up to 32.9%)] that were accompanied by usually smaller amounts of bornyl-compounds and acyclic compounds. Some exceptional (in O. vulgare rare) chemotypes were detected. The essential oil content of Austrian O. vulgare subsp. vulgare ranged between 0.1 and 1.8%. The content of rosmarinic acid was analysed by HPLC and ranged from 0.6 mg/g dry mass up to 37.2 mg/g dry mass. No arbutin could be detected in the analysed populations.     

Chemical polymorphism of the essential oils from populations of Thymus caespititius grown on the island S. Jorge (Azores)

The compositions of the essential oils obtained from ten populations of Thymus caespititius grown on S. Jorge (Azores) were studied by GC and GC-MS. All the oils analysed were dominated by their monoterpene fraction (69-9%). The sesquiterpene fraction was rather small (4-17%) and consisted mainly of oxygen-containing compounds (3-13%). Enantiomeric ratio of sabinene and alpha-terpineol was investigated in the oils from some populations. (+)-Sabinene was detected with high enatiomeric purity (96 99%). Although ( +)-alpha terpineol was the predominant enantiomer, its purity varied considerably (66-97%). Cluster analysis of all identified components grouped the oils into four main clusters that corresponded with their major components: alpha-terpineol (43-68%), carvacrol (32-52%), thymol (44-58%) and sabinene (41%). The essential oil from Th. caespititius showed a clear chemical polymorphism, that was particularly evident among four populations growing along a 200 m distance at Pico Verde.     

Chemical composition of the essential oil of Phlomis linearis Boiss. & Bal., and biological effects on the CAM-assay: a safety evaluation

Phlomis linearis Boiss. & Bal. of the Lamiaceae family growing in central, east and southeast Anatolia is an endemic species for Turkey. The essential oil obtained from the aerial parts by hydro distillation was subsequently analyzed by GC/MS. The main components of the oil were found as beta-caryophyllene (24.2%), germacrene D (22.3%) and caryophyllene oxide (9.2%), among 49 identified compounds, representing 94.5% of the total essential oil. The overall biological activity of the essential oil (100 microg/pellet) was tested on the chorioallantoic membrane (CAM) of the fertilized hen's egg in order to examine the anti-angiogenic and anti-inflammatory activity. None of the tests showed pronounced activity, toxicity or irritation at the tested concentration.     

Volatile constituents of the leaves of Siparuna thecaphora (Siparunaceae) from Turrialba,Costa Rica

The composition of the essential oil from leaves of Siparuna thecaphora (Poepp. et Endl.) A. DC. collected in Turrialba, Costa Rica, was determined by capillary GC/MS. Seventy-six compounds were identified corresponding to ca. 95% of the oil. The major components were germacrene D (32.7%), alpha-pinene (16.3%), beta-pinene (13.8%) and beta-caryophyllene (4.1%). Thirty-one minor compounds were identified for the first time in this genus of plants.     

Variability in essential oil composition of Piper dilatatum L.C. Rich

Twelve samples of air-dried aerial parts of Piper dilatatum L. C. Rich yielded essential oils and their volatile constituents were analyzed by GC and GC–MS. Sesquiterpenes, both hydrocarbons and oxygenated, were the most highly represented classes, the former ranging from 31.5% to 87.7% and the latter varying from 1.8% to 49.4%. Using hierarchical cluster analysis, the oils were divided into seven groups, whose main constituents were: (E)-caryophyllene, α-cadinol and germacrene D (group A); spathulenol, bicyclogermacrene and (Z)-β-ocimene, (group B); spathulenol, germacrene D and (E)-nerolidol, (group C); germacrene D, limonene, α-phellandrene and bicyclogermacrene (group D); β-elemene, germacrene D and β-pinene (group E); curzerene, p-cymene and α-eudesmol (group F); and (Z)-α-bisabolene, curzerene and germacrene D (group G). We have seen that Piper oils from the Amazon present as major constituents terpenoids and phenylpropanoids, always with the predominance of one over another. The essential oils of P. dilatatum presented in this paper, containing only mono- and sesquiterpenes as its major components, is further chemotaxonomic evidence of this dichotomy in the Piper genus.     

Essential oils composition of Eupatorium species growing wild in the Amazon

The essential oils of six Eupatorium species were obtained by hydrodistillation and analysed by GC-MS. The oil of E. macrophyllum was rich in sabinene (46.7%) and limonene (23.3%). The oil of E. laevigatum was mainly constituted by a mixture of aristolone+laevigatin (23.6%), globulol (16.2%) and germacrene D (8.6%). The principal constituents of the oils of the chemotypes A and B of E. squalidum, E. amygdalinum and E. conyzoides were caryophyllene oxide (17.4–30.1%), globulol (25.1%), germacrene D (10.4–21.6%), spathulenol (14.2%) and β-caryophyllene (7.1–12.3%). The oils of the chemotypes A and B of E. marginatum were dominated by α-zingiberene (57.5%), α-gurjunene (19.5%), germacrene D (14.8%), (E)-8-bisabolene (9.7%) and α-selinene (9.0%).     

Chemical Variability of Cleistopholis patens (Benth.) Engl. et Diels Leaf Oil from Ivory Coast

The chemical composition of 48 leaf oil samples isolated from individual plants of Cleistopholis patens (Benth .) Engl. et Diels harvested in four Ivoirian forests was investigated by GC‐FID (determination of retention indices), GC/MS, and ¹³C‐NMR analyses. The main components identified were β‐pinene (traces–59.1%), sabinene (traces–54.2%), (E)‐β‐caryophyllene (0.3–39.3%), linalool (0.1–38.5%), (E)‐β‐ocimene (0.1–33.2%), germacrene D (0.0–33.1%), α‐pinene (0.1–32.3%), and germacrene B (0–21.2%). The 48 oil compositions were submitted to hierarchical clustering and principal components analyses, which allowed the distinction of three groups within the oil samples. The oil composition of the major group (Group I, 33 samples) was dominated by (E)‐β‐caryophyllene and linalool. The oils of Group II (eight samples) contained mainly β‐pinene and α‐pinene, while those of Group III (seven samples) were dominated by sabinene, limonene, and β‐phellandrene. Moreover, the compositions of the Ivoirian C. patens leaf oils differed from those of Nigerian and Cameroonian origins.     

Volatile essential oil constituents of Alpinia smithiae (Zingiberaceae)

The composition of leaf and rhizome essential oils of Alpinia smithiae that grow wild in the Western Ghats of Kerala (South India) was analysed by gas chromatography. The major components were beta-caryophyllene, sabinene, myrcene and 1,8-cineole in both samples, but variation in the yield of oil as well as the major components between the two plant parts was observed.     

Variability of the needle essential oils of Pinus peuce from different populations in Montenegro and Serbia

The essential-oil composition of Pinus peuce Griseb. is reported at the population level. Macedonian pine is endemic high-mountain Balkan pine relict of an anthropogenically reduced area, with large morphological diversity and insufficiently clear taxonomic position. In the pine-needle terpene profile of two populations from Montenegro and one from Serbia, 78 compounds were detected, 56 of which are identified (Table 3). The dominant constituents were alpha-pinene (36.5%) and germacrene D (11.4%). The following 20 additional components were found to be present in medium-to-high amounts (0.5-10%): camphene (8.5%), bornyl acetate (6.8%), beta-pinene (6.8%), beta-caryophyllene (5.2%), beta-phellandrene (4.7%), terpinen-4-ol acetate (1.6%), (E)-hex-2-enal (1.5%), alpha-muurolene (1.2%), beta-gurjunene (1.1%), beta-myrcene (1.0%), alpha-terpinyl acetate (0.9%), alpha-phellandrene (0.8%), delta-cadinene (0.8%), alpha-humulene (0.8%), sabinene (0.7%), aromadendrene (0.6%), alpha-thujene (0.6%), gamma-muurolene (0.6%), gamma-cadinene (0.6%), alpha-terpinolene (0.5%), and one unknown component (0.5%). The similarity of the populations and the within-population variability were visualized by principle-component analysis (PCA) and genetic analysis of selected terpenes in 90 tree samples. Our study suggests a closer connection between populations II and III compared to population I. Based on the profile of the main terpene components, the studied populations are more similar to populations from Kosovo and Greece than to the population from Mt. Mokra (Montenegro) and the population in France.     

Volatile Compounds in Fruits of Peucedanum cervaria (Lap.) L.

The volatile compounds from Peucedanum cervaria (Lap. ) L. were obtained by hydrodistillation (HD) and headspace solid‐phase microextraction techniques (HS‐SPME), and then analyzed by GC/MS methods. The composition of samples from a botanical garden was compared with plants collected in the wild. The main compounds of the essential oils of P. cervaria were identified as α‐pinene, sabinene, and β‐pinene (more than 80% of oil). The content of β‐myrcene, limonene+β‐phellandrene, and germacrene D was higher than 1%. The in vitro antibacterial activity of the essential oil was evaluated by the agar dilution method against ten reference strains of Gram‐positive and Gram‐negative bacteria.     

Chemical Studies on the Essential Oils of Foeniculum vulgare

Twenty seven chemical constituents of oils from sweet leaves, flowers and fruits of Foeniculum vulgare Mill. are examined by GC and GC-MS with both different chromatographic columns. They are 1,1-diethoxyethane, α-thujene, α-pinene, camphene, sabinene, β-pinene, myrcene, α- phellandrene, p-cymene, limonene, cineole, γ-terpinene, fenchone, camphor, terpinen-4-ol, α-terpineol, estragole, verbenone, fenchol acetate, carveol, trans-fenchol acetate, carvone, anethole, anisaldehyde, trans-anethole, methoxyphenyl acetone and benzoic acid, 4-methoxy-, othylester. The limonene is 57.8% in the essential oil from leaves, 34.2% from flowers, 13.1% from fruits, The trans-anethole is 21.8% in the essential oil from leaves, 41.2% from flowers, 63.4% from fruits.     

Volatile compounds from some wild growing aromatic herbs of the Lamiaceae from southern France

Abstract

The composition of the volatile fraction in selected aromatic plants of the Lamiaceae from garrigue sites in southern France is described. Calamintha nepeta appeared heterogeneous. The oil was dominated by piperitone oxide, and piperitenone oxide or by pulegone and menthone. In Nepeta nepetella, nepetalactone, almost exclusively the (4a-α, 7α, 7a-β)-isomer, made up more than 85% of the essential oil. Dichloromethane extracts from Teucrium polium contained germacrene D or sabinene as main components, α-pinene, β-pinene and β-caryophyllene in varying proportions as further important constituents, and various minor components depending on the origin.     

Chemical composition and antimicrobial activity of volatile compounds of Tamarix boveana (Tamaricaceae)

The chemical composition of the Tamarix boveana volatile oils obtained from the whole aerial part, flowers, leaves and stems by steam distillation was analysed using gas chromatograph (GC)-flame ionization detectors (FID) and GC-MS. Sixty-two components were identified. Hexadecanoic acid (18.14%), docosane (13.34%), germacrene D (7.68%), fenchyl acetate (7.34%), Benzyl benzoate (4.11%) were found to be the major components in the whole aerial parts. This composition differed according to the tested part: 2.4 Nonadienal was the main compound in the flowers (12.13%) while germacrene D was the major component in leaves (31.43%) and hexadecanoic acid in the stems (13.94%). To evaluate in vitro antimicrobial activity, all volatile oils were tested against six Gram-positive and Gram-negative bacteria and four fungi. The T. boveana volatile oils exhibited an interesting antibacterial activity against all strains tested except Pseudomonas aeruginosa but no antifungal activity was detected.     

Antimicrobial activity of some Satureja essential oils

The genus Satureja is represented by fifteen species of which five are endemic and Satureja pilosa and S. icarica have recently been found as new records for Turkey. Aerial parts of the Satureja pilosa, S. icarica, S. boissieri and S. coerulea collected from different localities in Turkey were subjected to hydrodistillation to yield essential oils which were subsequently analysed by GC and GC/MS. The main constituents of the oils were identified, and both antibacterial and antifungal bioassays were applied. Carvacrol (59.2%, 44.8%, 42.1%) was the main component in the oils of S. icarica, S. boissieri and S. pilosa, respectively. The oil of S. coerulea contained beta-caryophyllene (10.6%) and caryophyllene oxide (8.0%) as main constituents.     

Essential oils from Azorean Laurus azorica

The essential oils isolated from leaves of ten and from unripe berries of eight populations of Laurus azorica (Seub.) Franco, collected on five islands of the Azorean archipelago, were analysed by GC and GC-MS. All oil samples were dominated by their monoterpene fraction (60-94%), alpha-pinene (15-37%) and 1,8-cineole (12-31%) being the main components of the leaf oils, while trans-beta-ocimene (27-45%) and alpha-pinene (12-22%) were the main components of the oils from the berries. The sesquiterpene fractions of the oils ranged from 3 to 17% and the main components were beta-caryophyllene (traces-8%) and beta-elemene (traces-3%) both in the leaf and berry oils. Some phenylpropanoid components were also present, in total amounting to 17%, trans-cinnamyl acetate (215% of the leaf oils) being the main component of this fraction. Cluster analysis of the enantiomeric composition of alpha- and beta-pinene in the oils from the leaves clearly showed two groups, one constituted by the two populations growing on the island S. Jorge, and the other constituted by the remaining populations.     

Chemical Variability of the Leaf Essential Oil of Xylopia aethiopica (Dunal) A.Rich. from Côte d'Ivoire

The chemical composition of 48 essential‐oil samples isolated from the leaves of Xylopia aethiopica harvested in six Ivoirian forests was investigated by GC‐FID and ¹³C‐NMR analyses. In total, 23 components accounting for 82.5–96.1% of the oil composition were identified. The composition was dominated by the monoterpene hydrocarbons β‐pinene (up to 61.1%) and α‐pinene (up to 18.6%) and the sesquiterpene hydrocarbon germacrene D (up to 28.7%). Hierarchical cluster and principal component analyses allowed the distinction of two groups on the basis of the β‐pinene and germacrene D contents. The chemical composition of the oils of Group I (38 oil samples) was clearly dominated by β‐pinene, while those of Group II (10 samples) were characterized by the association of β‐pinene and germacrene D. The leaves collected in the four inland forests produced β‐pinene‐rich oils (Group I), while the oil samples belonging to Group II were isolated from leaves harvested in forests located near the littoral.