Essential oil analysis and antimicrobial activity of eight Stachys species from Greece

The volatile composition of eight Stachys species has been studied. The investigated taxa were St. alopecuros (L.) Bentham., St. scardica (Griseb.) Hayek, St. cretica L. ssp. cretica, St. germanica L. ssp. heldreichii (Boiss.) Hayek, St. recta L., St. spinulosa L., St. euboica Rech. and St. menthifolia Vis., growing wild in Greece. The essential oils were obtained by hydrodistillation in a modified Clevenger-type apparatus, and their analyses were performed by GC and GC-MS. Identification of the substances was made by comparison of mass spectra and retention indices with literature records. Sesquiterpene hydrocarbons were shown to be the main group of constituents of all taxa. Furthermore, the obtained essential oils were tested against the following six bacteria: Pseudomonas aeruginosa (ATCC 27853), Escherichia coli (ATCC 35210), Bacillus subtilis (ATCC 10907), Bacillus cereus (clinical isolates), Micrococcus flavus (ATCC 10240), Staphylococcus epidermidis (ATCC 2228), as well as against the following five fungi: Aspergillus niger (ATCC 6275), Penicillium ochrochloron (ATCC 9112), Epidermophyton floccosum (clinical isolates), Candida albicans (clinical isolates) and Trichophyton mentagrophytes (clinical isolates). The tested essential oils showed better activity against bacterial species than against fungi. Pseudomonas aeruginosa was the most resistant strain, as none of the essential oils was active against this strain. The essential oil of St. scardica has been proven most active against both bacteria and fungi.     

Essential oils of seven Stachys taxa from Croatia

The essential oils of Stachys alpina L., Stachys officinalis (L.) Trevis., Stachys palustris L., Stachys recta L. subsp. recta, S. recta L. subsp. subcrenata (Vis.) Briq., Stachys salviifolia Ten., and Stachys sylvatica L. were obtained by hydrodistillation and analysed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). Sesquiterpene hydrocarbons were the main group of constituents of all taxa, except S. alpina, which was rich in oxygenated sesquiterpenes. S. alpina and S. palustris had a significant aldehyde fraction and a high amount of alcohols. Some differences in the essential oil composition of two subspecies of S. recta (S. recta subsp. recta and S. recta subsp. subcrenata), growing under almost identical conditions, have been found.     

Essential oils from two endemic species of Apiaceae from Iran

The composition of essential oils of Leutea glaucopruinosa (Rech.f.) Akhani & Salimian comb. nov., and Zeravschania (Boiss. & Hausskn.) Salimian & Akhani comb. nov. were analysed by GC-MS. 49 compounds are identified in the former and 33 compounds in the latter, comprising a total of 76 compounds in both species. Both species were originally described under Peucedanum, which are transferred in this paper into Leutea and Zeravschania, respectively. The chemical compounds of the essential oils show that there are only seven common compounds between two species. The major compounds of L. glaucopruinosa are mostly monoterpene hydrocarbons and oxygenated monoterpenes, in which alpha-pinene (31.5%), sabinene (9.7%), beta-pinene (9.2%), exo-fenchyl acetate (4.5%) are dominant. In Z. pastinacifolia sesquiterpene hydrocarbons and phenylpropanoids dominate with beta-bisabolene (37.3%), 3,1-butyl-1,2-dimethoxy benzene (14.9%), 10,11-dimethylbicyclo[6.3.0]undec-(8)-en-9-one (12.9%), 4-t-butyl-1,2-dimethoxy benzene (6.8%), (E)-asarone (5.1%) and elemicine (4.1%) as major compounds.     

Chemotaxonomic significance of the essential oils of 18 Ferula species (Apiaceae) from Iran

To evaluate the chemotaxonomic significance of the essential oils of 23 populations of 18 Iranian Ferula species, the chemical composition of the oils was investigated by GC/FID and GC/MS. Altogether, 84 constituents, representing 81.3-99.7% of the total composition of the oils, have been identified. The composition of six species of the genus, i.e., F. oopoda, F. foetida, F. behboudiana, F. diversivittata, F. galbaniflua, and F. hezarlalehzarica, has been reported for the first time. The main constituents identified were α-terpinyl acetate (73.3%), 2,3,4-trimethylthiophene (2; 49.0%), sabinene (75.3%), verbenone (5; 69.4%), β-pinene (59.0-66.3%), and (Z)-β-ocimene (41.7%). Cluster analysis (CA) of the percentage content of the essential oil components of the Ferula species resulted in the characterization of four groups, i.e., taxa containing either i) monoterpene hydrocarbons, ii) oxygenated monoterpenes, iii) organosulfur compounds, or iv) monoterpene, sesquiterpene, and aliphatic hydrocarbons as the principal classes of compounds. Based on the results obtained, the chemical independence of F. hirtella from F. szowitsiana and of F. galbaniflua from F. gummosa at the specific level was concluded and their positions as distinct species were confirmed. The chemotaxonomic relationships among the representatives of the genus Ferula have been discussed in detail.     

Essential oil composition and variability of Thymus lotocephalus and Thymusxmourae

The composition of the essential oils of four populations of Thymus lotocephalus G. López and R. Morales and one population of T.xmourae Paiva and Salgueiro, two endemic taxa from Portugal, was investigated mainly by GC and GC-MS. Txmourae is a natural hybrid between T. lotocephalus and T. mastichina (L.) L. subsp. donyanae R. Morales, which essential oil was analysed for the first time. In its oil, it was possible to find compounds of both parents, which could enable us to confirm its intermediate status between those two taxa. 1,8-Cineole and borneol were the main constituents in the essential oil of T.xmourae, whereas linalool, geranyl acetate and 1,8-cineol were the major ones in T. lotocephalus. Intermedeol was also an important constituent in the oils of both taxa. Nevertheless, the volatile oils of the four populations investigated of T. lotocephalus showed important differences among the main constituents. In order to study their infraspecific variability, the results obtained in the analysis of individual plants were submitted to a Principal Component and Chemometric Cluster Analyses. Five types of essential oils were found: linalool, 1,8-cineole, linalool/1,8-cineole, linalyl acetate/linalool and geranyl acetate.     

Chemical diversity of volatiles of Teucrium orientale L. var. orientale, var. puberulens, and var. glabrescens determined by simultaneous GC-FID and GC/MS techniques

In the present work, three varieties of Teucrium orientale, var. orientale, var. puberulens, and var. glabrescens, were collected and investigated for chemical composition of the oils. Subsequent gas chromatography (GC-FID) and gas chromatography coupled to mass spectrometry (GC/MS) revealed high abundance of sesquiterpenes in the essential oils analyzed. All the oils contained β-caryophyllene (22.6, 8.5, and 6.3%, resp.) and hexadecanoic acid (7.9, 12.8, and 13.1%). Germacrene D (24.6 and 33.4%) and bicyclogermacrene (6.7 and 8.5%) were found to be the main constituents of var. orientale and var. puberulens, respectively. The high percentages of β-cubebene (26.9%), α-cubebene (9.0%), and α-copaene (7.2%) established the diversity of var. glabrescens. The qualitative difference between the essential oils allowed the differentiation between the varieties in agreement with the morphological observations described in Flora of Turkey for each variety studied. In addition, a cluster analysis of twelve Teucrium taxa based on the essential-oil composition has been carried out. Hovewer, the analysis did not clearly reflect the infrageneric classification of the genus, it largely confirmed the relationships between the infraspecific taxa of Teucrium orientale and T. chamaedrys.     

Essential Oil Composition of Different Plant Parts from Croatian Petasites albus (L.) Gaertn. and Petasites hybridus (L.) G.Gaertn., B.Mey. & Scherb. (Asteraceae)

Essential oil compositions of fresh leaves, flower stems and rhizomes obtained by hydrodistillation from different Croatian populations of Petasites albus (L.) Gaertn. and Petasites hybridus (L.) G.Gaertn., B.Mey. & Scherb. (four of each species) were investigated using gas chromatography‐flame ionization detection and gas chromatography‐mass spectrometry. Altogether, 118 constituents were identified, accounting for 81.19–96.81 % of total oil composition. All essential oils were characterized by oxygenated sesquiterpenes, with distinct compounds recorded for both investigated species. Clear separation between the two species was confirmed by principal component analysis and hierarchical cluster analysis. This is the first study that recorded intraspecific variations of essential oil constituents from P. albus and P. hybridus. Obtained results could contribute to the understanding of their medicinal and nutritional value.     

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.     

Chemical classification of the essential oils of the Iranian Salvia species in comparison with their botanical taxonomy

The essential oils of eight Salvia species collected from different localities in Iran were analyzed by gas chromatography/mass spectrometry (GC/MS). The analytical results were compared with those previously published for related Iranian sage species in order to identify chemical markers for these species. Salvia eremophila, S. hypoleuca, and S. reuteriana are endemic, while S. atropatana, S. chloroleuca, S. santolinifolia, S. aegyptiaca, and S. macrosiphon also grow wild in neighboring countries. We categorized the Iranian Salvia species into four main chemotypes according to their essential-oil constituents: those which are dominated by 1) monoterpenes, 2) mono- and sesquiterpenes, or 3) sesquiterpenes as the major constituents, and 4) those containing low-molecular-weight acids, aldehydes, and esters, and green-leaf volatiles (GLVs). Likely due to the chemical diversity of different Salvia chemotypes, this categorization was supported by principal component analysis (PCA) for the group sampled here, but not for the values reported in the literature. We identified the following chemical markers: α-pinene, β-pinene, 1,8-cineol, linalool, and borneol in monoterpene-rich species, or β-caryophyllene, germacrene D, bicyclogermacrene, spathulenol, and caryophyllene oxide in sesquiterpene-rich species. Among these, α-pinene, β-caryophyllene, and germacrene D are the most common and abundant in the Salvia species investigated. In accordance with their close biological taxonomy, the chemical similarity of the essential oils of S. santolinifolia and S. eremophila is so high that we may consider them chemically identical.     

An interpopulation study of the essential oils of Cistus parviflorus L. growing in Crete (Greece)

The composition of the essential oils of nine populations of Cistus parviflorus L., from Crete (Greece) and their interpopulation variability, were investigated by GC-MS. 114 compounds were identified representing an average of 85-96% of oil composition. Labdane diterpenes were detected and identified in the essential oils of Cistus parviflorus L. for the first time. The results obtained from GC-MS analysis of the volatile oils were submitted to principal component and chemometric cluster analysis. Two main chemotypes (clusters) were differentiated; the first of West Crete and the second of East Crete. Carvacrol, caryophyllene oxide, alpha-epi-cadinol, abietatriene, 4-epi-dehydroabietol, dehydro abietol, cis-ferruginol and manoyl oxide mixture of isomers are the main constituents, while oxygenated sesquiterpenes as well as diterpenes have been found in high percentage composition.     

A comparative study of Scalesia species (Asteraceae) by gas chromatographic analysis of the monoterpene hydrocarbons of their essential oils

ADSERSEN, A. & SVENDSEN, A. B., 1986. A comparative study of Scalesia species (Asteraceae) by gas chromatographic analysis of the monoterpene hydrocarbons of their essential oils. The monoterpene hydrocarbons of the essential oils of 13 species of Scalesia , Asteraceae, endemic to the Galapagos Islands, were analysed by gas chromatography to determine whether the composition of these compounds could show any characteristics for the various species. Marked differences in the monoterpene hydrocarbon patterns of the Scalesia species investigated were observed. Whereas a-pinene was usually found in amounts of 30–50%, Scalesia villosa contained only 12%. Sabinene usually occurred in amounts of 10-1.5%, but S. divisa and S. affinis contained about twice as much. The limonene content was usually less than 1%, but S. microcephala, S. baurii and S. affinis contained amounts varying from about 2% to 9.5%.     

The genus Pinus: a comparative study on the needle essential oil composition of 46 pine species

The fresh needles of 46 pine species, including 37 and 17 taxa of the subgenera Pinus and Strobus, respectively, were subjected to hydrodistillation and the essential oils obtained were analyzed by means of GC–FID and GC–MS. The comprehensive analyses of the needle oils, which allowed for the identification of 161 constituents comprising the majority of the volatiles, showed significant, not only quantitative, but also qualitative differences between the samples. Monoterpenes, sesquiterpenes and diterpenes dominated the pine foliage oils, with the presence of the monoterpene hydrocarbons α- and β-pinene and the sesquiterpene hydrocarbon germacrene D characterizing most of the oils. This is the first report on the chemical composition of the essential oils of 21 pine taxa, including 15 taxa of subgenus Pinus and 6 taxa of subgenus Strobus.     

Beta-cyclolavandulyl and beta-isocyclolavandulyl esters from Peucedanum paniculatum L., an endemic species to Corsica

Eight cyclolavandulyl esters (beta-cyclolavandulyl and beta-isocyclolavandulyl acetate, propionate, isobutyrate, isovalerate) were identified in the leaf and root oils of Peucedanum paniculatum L., an endemic species to Corsica, by comparison of their spectroscopic data with those of synthetic material. Their structures were elucidated by spectroscopic methods. The antimicrobial activity of essential oils of leaves and roots was evaluated against eleven microorganisms.     

Volatiles of Curcuma mangga Val. & Zijp (Zingiberaceae) from Malaysia

Analysis by GC and GC/MS of the essential oil obtained from Malaysian Curcuma mangga Val. & Zijp (Zingiberaceae) rhizomes allowed the identification of 97 constituents, comprising 89.5% of the total oil composition. The major compounds were identified as myrcene (1; 46.5%) and β-pinene (2; 14.6%). The chemical composition of this and additional 13 oils obtained from selected Curcuma L. taxa were compared using multivariate statistical analyses (agglomerative hierarchical cluster analysis and principal component analysis). The results of the statistical analyses of this particular data set pointed out that 1 could be potentially used as a valuable infrageneric chemotaxonomical marker for C. mangga. Moreover, it seems that C. mangga, C. xanthorrhiza Roxb., and C. longa L. are, with respect to the volatile secondary metabolites, closely related. In addition, comparison of the essential oil profiles revealed a potential influence of the environmental (geographical) factors, alongside with the genetic ones, on the production of volatile secondary metabolites in Curcuma taxa.     

In vitro activity of essential oils extracted from plants used as spices against fluconazole-resistant and fluconazole-susceptible Candida spp

In the present study, the antifungal activity of selected essential oils obtained from plants used as spices was evaluated against both fluconazole-resistant and fluconazole-susceptible Candida spp. The Candida species studied were Candida albicans, Candida dubliniensis, Candida tropicalis, Candida glabrata, and Candida krusei. For comparison purposes, they were arranged in groups as C. albicans, C. dubliniensis, and Candida non-albicans. The essential oils were obtained from Cinnamomum zeylanicum Breyn, Lippia graveolens HBK, Ocimum basilicum L., Origanum vulgare L., Rosmarinus officinalis L., Salvia officinalis L., Thymus vulgaris L., and Zingiber officinale. The susceptibility tests were based on the M27-A2 methodology. The chemical composition of the essential oils was obtained by gas chromatography-mass spectroscopy and by retention indices. The results showed that cinnamon, Mexican oregano, oregano, thyme, and ginger essential oils have different levels of antifungal activity. Oregano and ginger essential oils were found to be the most and the least efficient, respectively. The main finding was that the susceptibilities of fluconazole-resistant C. albicans, C. dubliniensis, and Candida non-albicans to Mexican oregano, oregano, thyme, and ginger essential oils were higher than those of the fluconazole-susceptible yeasts (P<0.05). In contrast, fluconazole-resistant C. albicans and Candida non-albicans were less susceptible to cinnamon essential oil than their fluconazole-susceptible counterparts (P<0.05). A relationship between the yeasts' susceptibilities and the chemical composition of the essential oils studied was apparent when these 2 parameters were compared. Finally, basil, rosemary, and sage essential oils did not show antifungal activity against Candida isolates at the tested concentrations.     

Inhibition by the essential oils of peppermint and spearmint of the growth of pathogenic bacteria

The effects of the, essential oils of peppermint (Mentha piperita L.), spearmint Mentha spicata L.) and Japanese mint (Mentha, arvensis L.), of four major constituents of the esssential oil of peppermint, and of three major constituents of the essential oil of spearmint, on the proliferation of Helicobacter pylori, Salmonella enteritidis, Escherichia coli O157:H7, methicillin-resistant Staphylococcus aureus (MRSA) and methicillin sensitive Staphylococccus aureus (MSSA) were examined. The essential oils and the various constituents inhibited the proliferation of each strain in liquid culture in a dose-dependent manner. In addition, they exhibited bactericidal activity in phosphate-buffered saline. The antibacterial activities varied among the bacterial species tested but were almost the same against antibiotic-resistant and antibiotic-sensitive strains of Helicobacter pylori and S. aureus. Thus, the essential oils and their constituents may be useful as potential antibacterial agents for inhibition of the growth of pathogens.     

Fumigant activity of plant essential oils and components from Schizonepeta tenuifolia against Lycoriella ingenua (Diptera: Sciaridae)

Plant essential oils from 21 plant species were tested for their insecticidal activities against larvae of Lycoriella ingenua Dufour (Diptera: Sciaridae) by using a fumigation bioassay. Good insecticidal activity against larvae of L. ingenua was achieved with essential oils of Acorus gramineus Solander, Schizonepeta tenuifolia Briquet, and Zanthoxylum piperitum De Candolle at 25 microg/ml air. S. tenuifolia oil showed the most potent insecticidal activity among the plant essential oils. At 12.5 microg/ml air concentration, S. tenuifolia oil caused 96.6% mortality, but mortality decreased to 60% at 3.125 microg/ml air. Analysis by gas chromatography-mass spectrometry led to identification of three major compounds from S. tenuifolia oil. These three compounds were tested individually for their insecticidal activities against larvae of L. ingenua and compared with the toxicity of dichlorvos. Pulegone was the most toxic, followed by menthone and limonene with LC50 values of 1.21, 6.03, and 15.42 microg/ml, respectively. LC50 of dichlorvos was 8.13 microg/ml. Effects of S. tenuifolia and its components on growth of Pleurotus ostreatus (Jacq. ex Fr.) Kummer also were investigated.     

Volatiles of Geranium purpureum Vill. and Geranium phaeum L.: Chemotaxonomy of Balkan Geranium and Erodium Species (Geraniaceae)

The essential oils obtained by hydrodistillation of Geranium purpureum and G. phaeum were characterized by GC‐FID and GC/MS analyses (the former for the first time in general). In total, 154 constituents were identified, accounting for 89.0–95.8% of the detected GC peak areas. The investigated essential oils consisted mainly of fatty acids and fatty‐acid‐derived compounds (45.4–81.3%), with hexadecanoic acid and (E)‐phytol as the major components. The chemotaxonomic significance of the variations in the essential‐oil composition/production of the presently and previously investigated Geranium and highly related Erodium taxa from Serbia and Macedonia was assessed by multivariate statistical analyses. The main conclusions drawn from the high chemical similarity of the two genera, visible from the obtained dendrograms and biplots, confirm the close phylogenetic relationship between the investigated Geranium and Erodium taxa, i.e., that there is no great intergeneric oil‐composition variability. Changes in the composition and production of essential oils of the herein investigated taxa and 60 other randomly chosen species belonging to different plant genera were also statistically analyzed. The results put forward pro arguments for the oil‐yield–oil‐composition correlation hypothesis.     

Chemical composition of hips essential oils of some Rosa L. species

The chemical composition of the hips essential oils of 9 taxa of Rosa L. was analyzed and compared using the standardized analytical GC and GC/MS methods. The volatile hips oil compositions for these species are presented. All oil samples were dominated by following components: vitispiran (isomer), a-E-acaridial, dodecanoic acid, hexadecanoic acid, docosane (C22), beta-ionone, 6-methyl-5-hepten-2-one, 2-heptanone, heptanal, myristic acid and linolic acid. Statistical analyses of 97 GC peaks of these oils were used to distinguish compositional patterns. There appeared to be correlation between the essential oil patterns and the classification within Rosa L. Cluster analysis of the composition of main components clearly showed two groups, one constituted by R. rugosa Thunb. from the Cinnamomea section, and the other constituted by the remaining taxa from the Caninae section.