Essential oil constituents derived from different organs of a relictual conifer Wollemia nobilis

The chemical composition of the essential oil of leaves (0.9%, w/v) and twigs (0.33%, w/v) of Wollemia nobilis (Araucariaceae) – a remnant species thought to have been extinct for 65 million years – was investigated by GC/MS. The main constituents of both leaf- and twig-derived oil samples were 16-kaurene (61.8% and 38.2%, respectively) and germacrene D (9.9% and 22%). The principal difference was a considerably more pronounced sesquiterpene presence in the twig-oil, amounting to 33.5%, than in its folial counterpart (23.4%). On the contrary, while remaining the dominant group in both oil samples under investigation, diterpenoids were relatively more abundant in leaf-derived oil constituting 65.3%, versus 41.7% detected in twigs. To our knowledge, this is the first report dealing with the essential oil composition of Wollemi pine twigs, as opposed to the leaf-derived volatiles.     

Chemotaxonomy of Hypericum genus from Portugal: Geographical distribution and essential oils composition of Hypericum perfoliatum, Hypericum humifusum, Hypericum linarifolium and Hypericum pulchrum

The geographical distribution and analysis of the essential oils of species from three sections of Hypericum L. (Guttiferae/Clusiaceae/Hypericaceae) from Portugal are presented. Hypericum perfoliatum (section Drosocarpium) grows wild in the centre and south of Portugal; Hypericum humifusum and Hypericum linarifolium are both from section Oligostema, the former occurring throughout the country, while the second is distributed mainly in the north and centre; Hypericum pulchrum (section Taeniocarpium) is confined to the littoral north of Portugal. The essential oils were obtained by distillation–extraction, hydrodistillation and distillation in a modified Marcusson apparatus from the dried aerial parts of the different populations and were analysed by GC and GC–MS. Monoterpene hydrocarbons constituted the main fraction in all oils (43–69%, 53–85%, 28–45% and 48–65% for H. perfoliatum, H. humifusum, H. linarifolium and H. pulchrum, respectively). Sesquiterpene hydrocarbons (2–13%, 6–18%, 21–27% and 16–18%, respectively) and a third fraction of non-terpenic compounds (20–29%, 3–16%, 2–14% and 5–11%, respectively) from the four species attained relatively high amounts in all oils. Within each species, no major differences were detected in the essential oil composition, despite the fact that different locations, phenological phases and extraction methodologies were used. Notwithstanding the dominance of α-pinene in all four species' oils, cluster and principal components analysis on the identified components showed that the range of α-pinene, β-pinene and n-nonane supported a separation of the four species. The essential oil composition of the four species showed some qualitative resemblances, which correlate well with the taxonomical classification based on morphological characters.     

Essential oil from leaves of Cryptocarya mandioccana Meisner (Lauraceae): Composition and intraspecific chemical variability

The composition of the essential oil from leaves of Cryptocarya mandioccana has been determined by chromatographic fractionation and GC–FID, GC–MS and ¹³C NMR analyses, yielding the identification of 64 compounds with predominance of isomeric sesquiterpenes with molecular weights of 204. The main components of the oil obtained by hydrodistillation were β-caryophyllene, spathulenol, caryophyllene oxide, δ-cadinene, germacrene D, benzaldehyde and bicyclogermacrene. However, the oil obtained by steam distillation contained higher levels of sesquiterpene hydrocarbons, with predominance of β-caryophyllene (C), germacrene D (G) and bicyclogermacrene (B), and was considered to be more representative of the composition of the oil in its natural state. The intraspecific chemical variability of the essential oil obtained by steam distillation was evaluated within populations of trees growing at three separate locations in the state of São Paulo, Brazil. Three distinct chemical groups could be characterised due to differences in the relative percentages of the three main sesquiterpenes from essential oil: CGB [relative contents of C (14–34%), G (5–28%), B (8–15%)], BCG [B (17–34%), C (9–24%), G (12–25%)] and GCB [G (22–42%), C (4–17%), B (7–15%)]. Individuals from groups CGB and BCG were found to be more frequent at south locations while group GCB is predominant in north location.     

Essential oil composition of Achyrocline flaccida (Weinm.) DC. (Asteraceae) from different locations of Argentina

The qualitative and quantitative composition of the essential oils obtained from the inflorescences of Achyrocline flaccida (Asteraceae) has been investigated for the first time. Plant material was collected from eleven locations in Argentina. The essential oils were obtained by hydrodistillation (0.1–0.8% v/w, dried material) and analyzed by GC–FID–MS. Eighty-three compounds were identified representing more than the 90% of the oils. The major components were α-pinene and β-caryophyllene. Statistical analysis was performed in order to evaluate the variability of the essential oils analyzed. Two groups were formed reflecting only quantitative differences in the content of major compounds. The chemical pattern of essential oils observed for A. flaccida is similar to other Achyrocline species studied, except Achyrocline hyperchlora.     

Chemotypes of Achillea millefolium transferred from 14 different locations in Lithuania to the controlled environment

The composition of essential oils hydrodistilled from 19 samples of inflorescences and leaves of Achillea millefolium L. plants, which were transferred from 14 natural habitats in Lithuania to the field collection, is reported. Total content of oil was 0.15–0.55% in inflorescences and 0.06–0.19% (v/w) in leaves. In total 117 compounds were identified positively or tentatively. Data obtained clearly indicate the presence of a remarkable chemical polymorphism within the population of A. millefolium in Lithuania. The content of the major constituents in the oils from inflorescences varied in the following ranges: β-pinene, 0.33–62.29%; β-myrcene, 0.05–69.76%; α-phelandrene, 0.13–29.96%; 1,8-cineole, 2.30–21.57%; and chamazulene, 0.08–30.70%. According to the major components the essential oils' six chemotypes of A. millefolium were defined.     

Genetic diversity and chemical polymorphism of Thymus caespititius from Pico,São Jorge and Terceira islands (Azores)

Thirty-one individuals from Thymus caespititius were collected on the islands of Pico, São Jorge and Terceira (Azores) and the volatiles were isolated by distillation–extraction and analyzed by GC and GC–MS. The same plants were analyzed by RAPD using 17 arbitrary primers that generated 187 scorable polymorphic bands. The volatile composition of the individuals was in accordance with previous results obtained from the populations’ analysis, confirming that the chemical polymorphism was in some cases more evident among different plants from the same island than among those collected on different islands. RAPDs analyses using the same individuals did not show identical clustering as with the volatile oil profiles and no straight correlation among collection site, chemical analysis and molecular assessments could be found, suggesting that other molecular tools should be explored in order to fully understand the influence of both environmental and genetic factors on volatiles composition.     

Screening of the essential oil composition of wild Sicilian rosemary

The qualitative and quantitative composition of the essential oils obtained from wild Sicilian rosemary plants (Rosmarinus officinalis L.) has been investigated. Samples were collected in Sicily after an ideal division of the island into three large areas, namely Val Mazara (M), Val di Noto (N) and Val Demona (D), according to an ancient and historical territorial subdivision of the island. The essential oils were obtained by hydrodistillation and analyzed by GC-FID-MS, identifying 100 compounds representing more than 96% of the oils. Monoterpenes, both hydrocarbons and oxygenated, were the most highly represented components: the former with a range of 21–68% and the latter with a range of 29–79%. On the basis of the results of this study, comprising a cluster analysis, and on the commonly accepted subdivision of rosemary essential oils, namely cineoliferum, verbenoniferum and camphoriferum chemotypes, most of the wild Sicilian rosemary samples must be classified as cineoliferum chemotype.     

Screening the essential oil composition of wild Sicilian fennel

Fifty-six samples of wild fennel (Foeniculum vulgare Mill.) have been collected in different localities of Sicily and analysed for their content in seed essential oils. The GC-FID-MS analyses allowed identifying 78 compounds, representing more than 98% of the oils. Phenylpropanoids are the most highly represented components – 55 samples show estragole as the main compound ranging between 34 and 89%, while (E)-anethole is the other phenylpropanoid ranging between 0.1 and 36%, although it only reaches appreciable values in a few samples, largely being present below 1%. The oxygenated monoterpene, fenchone, a typical fennel oil component, has been found in all samples, in the 2–27% range; α-pinene (1–21%), limonene (1–17%) and γ-terpinene (<1–4%) were the monoterpene hydrocarbons found in all samples. Only one sample showed piperitenone oxide and limonene as main components, with 42 and 34%, respectively, and with the lack of any phenylpropanoid. Sesquiterpenes and others compounds class had only negligible values or were not detected in all samples. Statistical analyses allowed to single out five groups, reflecting the compositional differences of the essential oil profiles of the wild Sicilian fennel.     

Chemical composition,intraspecies variation and seasonal variation in essential oils of Calendula arvensis L.

The essential oil composition of Calendula arvensis was established for the first time using GC and GC/MS. Eighty-five essential oil components were identified, which accounted for 90.3 g/100 g of essential oil. The oil contained a high concentration of sesquiterpenes, of which δ-cadinene and α-cadinol were the main components. The chemical composition of 25 Corsican C. arvensis oils was analyzed to determine intraspecies variation in essential oil composition. A matrix linking essential oil composition to sample location was composed to identify relationships between concentrations of volatile samples and the geographical origins of samples. Two main groups of compounds were identified according to the amount of sesquiterpenic compounds (hydrocarbons and alcohols) and soil characteristics. Seasonal variation (winter vs. spring) in the concentrations of two major compounds during the flowering period was observed.     

Insecticidal activity and chemical composition of the essential oil of Artemisia vestita from China against Sitophilus zeamais

In our screening program for new agrochemicals from local wild plants, essential oil of Artemisia vestita Wall (Asteraceae) was found to possess strong insecticidal activity against maize weevil, Sitophilus zeamais Motsch. Essential oil of aerial parts of A. vestita was obtained from hydrodistillation and was investigated by GC and GC–MS. The main components of essential oil were grandisol (40.29%), 1,8-cineol (14.88%) and camphor (11.37%). The essential oil of A. vestita possessed strong fumigant toxicity against S. zeamais adults with a LC₅₀ value of 13.42 mg/L air. The essential oil of A. vestita also showed contact toxicity against S. zeamais adults with a LD₅₀ value of 50.62 mg/adult.     

Variability in essential oil composition of Turkish basils (Ocimum basilicum L.)

Sweet basil (Ocimum basilicum L.), one of the most popular aromatic plants, shows great variation in both morphology and essential oil components. In this study, the composition of 18 Turkish basil essential oils was investigated by GC and GC–MS. Variation of essential oils in the landraces was subjected to cluster analysis, and seven different chemotypes were identified. They were (1) linalool, (2) methyl cinnamate, (3) methyl cinnamate/linalool, (4) methyl eugenol, (5) citral, (6) methyl chavicol (estragol), and (7) methyl chavicol/citral. Methyl chavicol with high citral contents (methyl chavicol/citral) can be considered as a “new chemotype” in the Turkish basils. Because methyl eugenol and methyl chavicol have structural resemblance to carcinogenic phenylpropanoids, chemotypes having high linalool, methyl cinnamate or citral contents and a mixture of these is suitable to cultivate for use in industry.     

Chemical compositions,antimicrobial and herbicidal effects of essential oils isolated from Turkish Tanacetum aucheranum and Tanacetum chiliophyllum var. chiliophyllum

The chemical composition of essential oils isolated from the aerial parts by hydrodistillation of Turkish Tanacetum aucheranum and Tanacetum chiliophyllum var. chiliophyllum were analyzed by GC–MS. The oils contain similar major components. The major components of T. aucheranum oil were 1,8-cineole (23.8%), camphor (11.6%), terpinen-4-ol (7.2%), α-terpineol (6.5%), borneol (3.8%), (E)-thujone (3.2%), epi-α-cadinol (3.1%), and artemisia ketone (3.0%). Camphor (17.9%), 1,8-cineole (16.6%) and borneol (15.4%) were found to be predominant constituents in the oil of T. chiliophyllum. It is interesting to find that ester derivatives of dihydro-α-cyclogeranic acid (2,2,6-trimethylcyclohexylcarboxylate), dihydro-α-cyclogeranyl hexanoate (10.1%), dihydro-α-cyclogeranyl pentanoate (3.0%), dihydro-α-cyclogeranyl butanoate (2.1%) and dihydro-α-cyclogeranyl propionate (1.2%) are firstly found as chemotaxonomically important components in T. chiliophyllum oil. From these, dihydro-α-cyclogeranyl hexanoate was isolated on silica gel column chromatography and its structure was confirmed by spectroscopic methods. This is the first report on the occurrence of ester derivatives of dihydro-α-cyclogeranic acid in essential oils of Tanacetum species. The oils were also characterized to have relatively high amounts of oxygenated monoterpenes. Results of the antifungal testing by microbial growth inhibition assays showed that the oils completely inhibit the growth of 30 phytopathogenic fungi. However, their growth inhibition effects were lower than commercial benomyl. The oils tested for antibacterial activity against 33 bacterial strains showed a considerable antibacterial activity over a wide spectrum. Herbicidal effects of the oils on seed germination of Amaranthus retroflexus, Chenopodium album and Rumex crispus were also determined and the oils completely inhibited the seed germination and seedling growth of the plants.     

Screening of the essential oil composition of wild Sicilian thyme

Thirty samples of wild thyme collected from as many Sicilian locations have been analysed for their qualitative and quantitative essential oil profiles. The oils, obtained by hydrodistillation, have been analysed by a combination of GC-FID-MS; in all, 46 components, representing more than 98% of the oils, were fully characterized. Monoterpenes, both hydrocarbons and oxygenated, were the most highly represented components: the former with a range of 8–61% and the latter with a range of 31–86%. Carvacrol was the main compound in 29 samples, ranging between 49 and 83%, suggesting that Thymus capitatus Hoff. et Link. [syn. Coridothymus capitatus (L.) Rchb.f., Satureja capitata L., Thymbra capitata (L.) Cav.] is the most widespread wild species in the Sicilian area. Only one sample, identified as Thymus longicaulis C. Presl., collected from the North-East of Sicily showed a different composition, p-cymene and thymol being the main compounds with 40 and 16%, respectively. Statistical analyses allowed establishing a single broad group, confirming the substantial compositional uniformity of the essential oil profiles of the wild Sicilian thyme.     

Essential oil variability within and among populations of Cunila incisa Benth.

To evaluate the intra- and interpopulational variability of volatile compounds in Cunila incisa, 72 samples representing 12 populations, were collected all over the distribution area of the species in Rio Grande do Sul State. The samples were extracted by steam distillation and analyzed using GC and GC–MS. A total of 19 volatile compounds were detected and identified. In average, the main compounds were 1,8-cineole, α-terpineol, p-cymene, sabinene, terpinene-4-ol, and γ-terpinene. Negative correlation was detected between the concentrations of 1,8-cineole and α-terpineol. Significant variation in the concentration of volatile compounds was detected within and among populations. Multivariate analysis of volatile oil composition identified three groups. Most populations exhibited low intra-populational variation indicating foundation effect. Relation between geographic distribution and chemical composition was observed.     

Essential oil composition of two variants of Prostanthera lasianthos Labill. from Australia

The essential oils from the leaves of two variants of Prostanthera lasianthos Labill. have been analysed by GC and GC/MS. The different samples studied showed two chemotypes, the rheophytic variant, chemotype 1,8-cineole and β-pinene and the smooth-leaved variant with the chemotype linalool, linalyl acetate and β-selinene. The percentage composition of these compounds were 57.3–66.0%, 9.2–10.2%, 13.8–24.6%, 13.8–19.1% and 7.8–14.2%, respectively. One of the samples (P.l.n2) showed intermediate values so it could be a hybrid although it was morphologically similar to smooth-leaved variant. According to our chemical results and previous morphological studies we think that both variants could be recognised as distinct taxa level (subspecies or species) although further genetic research should be done to confirm this hypothesis.     

Volatile composition and antimicrobial activity of twenty commercial frankincense essential oil samples

Trees from the genus Boswellia (Burseraceae) are traditionally used as a medicine, a fumigant, in various cosmetic formulations and in aromatherapy in several countries around the world. This plant produces a commercial oil known as frankincense which has a woody, spicy and haunting smell. Frankincense oil has several pharmacological properties, of which many elude to the anti-infective potential. Variation in the chemical composition of this oil has been reported in literature. These factors prompted an investigation to study the commercial frankincense oils from various international suppliers. Twenty essential oils were analyzed by gas chromatography coupled to mass spectrometry. Considering the major constituents, the oils were found to be qualitatively similar. However, there was immense quantitative variation for certain oil constituents. The components identified and their range in the oils include α-pinene (2.0–64.7%); α-thujene (0.3–52.4%); β-pinene (0.3–13.1%); myrcene (1.1–22.4%); sabinene (0.5–7.0%); limonene (1.3–20.4%); p-cymene (2.7–16.9%) and β-caryophyllene (0.1–10.5%). The antimicrobial activity (minimum inhibition concentration assay) of the oils was investigated against five reference test organisms and the activity ranged from 4–16 mg/ml (Staphylococcus aureus); 1.5–8.3 mg/ml (Bacillus cereus); 4.0–12.0 mg/ml (Escherichia coli); 2.0–12.8 mg/ml (Proteus vulgaris) and 5.3–12.0 mg/ml (Candida albicans).     

Physiological changes and essential oil composition of clary sage (<Emphasis Type="Italic">Salvia sclarea</Emphasis> L.) rosette leaves as affected by salinity

Since soil salinity is a widespread problem, we proposed to focus on its effect on seedling growth, mineral composition and particularly on essential oil composition known to be reliable to abiotic conditions. Clary sage seedlings were hydroponically cultivated under different salt concentrations (0, 25, 50, and 75 mM NaCl). The dry biomass and the mineral element contents were determined. The essential oils were extracted and analyzed by GC and GC–MS. Results showed that growth was reduced by 42% at 75 mM. This growth decrease was accompanied by a decrease in tissue hydration and a slight restriction in K⁺ uptake, as well as an increase in Na⁺ levels. Concerning essential oil yields, the application of 25 mM NaCl increased significantly the oil yield which decreased with increasing salt concentration. Besides, the chemical composition of clary sage was found to be also strongly affected by salt treatment since each salt concentration appeared to induce a different new chemotype in clary sage essential oil.     

Chemical and biological profiles of Lavandula luisieri essential oils from western Iberia Peninsula populations

The chemical composition and biological activity of wild Lavandula luisieri (Rozeira) Rivas-Martínez populations from the south Beira interior region in central eastern Portugal are described. The essential oils of these four populations have been analyzed by GC–MS, and their antifeedant effects evaluated against Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi. Relative concentration data (% values) was subjected to principal component and cluster analysis. Relative concentration data and antifeedant effects were subjected to a stepwise multiple regression analysis. Additionally, one of these populations has been adapted to experimental field cultivation.     

Volatile and molecular characterization of two Portuguese endemic species: Angelica lignescens and Melanoselinum decipiens

Chemical and genetic differences of 11 individuals of Angelica lignescens and 3 individuals of Melanoselinum decipiens were studied to determine whether volatile components could be used as taxonomical markers and to examine the correlation between molecular and chemical markers. The volatiles were isolated from each individual by distillation–extraction and analyzed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). The same plants were analyzed by Inter Simple Sequence Repeat (ISSR) using 14 arbitrary primers. The main component of volatile fraction isolated from vegetative aerial parts of A. lignescens was limonene (57–86%) while in M. decipiens the main components detected were β-pinene (38–47%) and sabinene (1–33%). Cluster analyses based both on the chemical composition of volatile fraction and on molecular markers grouped the 14 accessions in two main groups, corresponding to each of the two species under study. Considering the species together, a moderate Pearson's correlation of r = 0.61 was obtained between the two analyses.     

Isozyme markers and volatiles in Tunisian Rosmarinus officinalis L. (Lamiaceae): A comparative analysis of population structure

Genetic and essential oil variations from 14 Tunisian natural populations of Rosmarinus officinalis L. were assessed using eight isozymes and 25 terpenoids. Isozymes were revealed by 13% gel electrophoresis. Volatiles were analysed by GC and GC–MS. Populations were collected from different regions belonging to sub-humid, upper semi-arid and upper arid bioclimates.