The hydrodistillation of the aerial parts of Stachys palaestina L. collected in Lebanon in the Kadisha Valley, yielded 0.1% (w/w) of essential oil. GC and GC-MS analyses enabled the identification of 87 compounds representing 90.8% of the total oil. Hexadecanoic acid (10%), hexahydrofarnesyl acetone (6.9%), eugenol (4.3%) and (E)-caryophyllene (4.3%) were the main components. On the whole, the oil was constituted mainly of sesquiterpenes (37.7%), among which sesquiterpene hydrocarbons (20.7%) slightly prevailed over oxygenated sesquiterpenes (17.0%). This is the first report on the chemical composition of S. palaestina essential oil.

The hydrodistillation of the aerial parts of Nepeta cilicica Boiss. ex Benth., collected in Lebanon in the Horsh Ehden reserve, yielded 0.13% (w/w) of essential oil. Gas chromatography (GC) and GC–mass spectroscopy analysis enabled the identification of 75 compounds representing 96.8% of the total oil. The most abundant compounds were spathulenol (15.1%), hexadecanoic acid (14%), δ-cadinene (5.5%) and α-copaene (4.5%). On the whole, the oil was constituted mainly by sesquiterpenes (45.9%), among which sesquiterpene hydrocarbons (27.6%) slightly prevailed over oxygenated sesquiterpenes (18.3%).

Essential oil extracted from dried aerial parts of Teucrium flavum ssp. flavum harvested in Zakynthos, Greece, was analysed by gas phase chomatography (GC) and gas chomatography mass spectrometry (GC-MS). The main constituents were caryophyllene (13.5%), caryophyllene oxide (8.5%), 4-vinyl guaiacol (6.0%) and alpha-humulene (5.0%).

The chemical composition of the essential oils obtained from aerial parts of Scutellaria orientalis L. ssp. alpina (Boiss.) O. Schwarz and S. utriculata Labill. growing wild in Lebanon, were analyzed by GC and GC-MS. In S. orientalis ssp. alpina, strongly characterized by sesquiterpenes (41.2%) and particularly sesquiterpene hydrocarbons (31.7%), hexahydrofarnesylacetone (11.7%) was recognized as the main constituent, together with hexadecanoic acid (7.6%), caryophyllene (7.4%), caryophyllene oxide (6.8%), 4-vinylguaiacol (5.4%) and germacrene D (5.4%). S. utriculata oil was instead constituted above all by monoterpenes (42.2%), particularly oxygen containing monoterpenes (39.9%), and in this oil the main compounds were linalool (20.1%), 4-vinyl guaiacol (15.5%), α-terpineol (8.9%), (E)-nerolidol (8.9%) and geraniol (8.2%).

The essential oils from twenty-two different Stachys species were obtained by hydrodistillation and analyzed by gas chromatography–mass spectrometry (GC–MS). Thirty-nine compounds, which accounted for 70.5–97.8% of the total composition of the oils, have been identified. Germacrene-D (2.9–45.3%), β-caryophyllene (2.3–62.3%), caryophyllene oxide (trace to 7.8%), spathulenol (trace to 7.8%) and α-cadinene (1.4–8.5%) have been identified as the main components of the essential oils. Antimicrobial assessments of the essential oils were evaluated against Escherichia coli, Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa and Candida albicans by disc diffusion method. Most of the essential oils showed moderate activity against the studied microorganisms.

The chemical composition of the essential oils obtained from aerial parts of Scutellaria orientalis L. ssp. alpina (Boiss.) O. Schwarz and S. utriculata Labill. growing wild in Lebanon, were analyzed by GC and GC-MS. In S. orientalis ssp. alpina , strongly characterized by sesquiterpenes (41.2%) and particularly sesquiterpene hydrocarbons (31.7%), hexahydrofarnesylacetone (11.7%) was recognized as the main constituent, together with hexadecanoic acid (7.6%), caryophyllene (7.4%), caryophyllene oxide (6.8%), 4-vinylguaiacol (5.4%) and germacrene D (5.4%). S. utriculata oil was instead constituted above all by monoterpenes (42.2%), particularly oxygen containing monoterpenes (39.9%), and in this oil the main compounds were linalool (20.1%), 4-vinyl guaiacol (15.5%), α-terpineol (8.9%), ( E )-nerolidol (8.9%) and geraniol (8.2%).

The occurrence of diterpenoids from roots and aerial parts of the species of the genus Stachys (Lamiaceae, Labiatae) is reviewed. The presence of these diterpenoids in other taxa and their biological properties have been also reviewed.

The essential oil of Nepeta glomerata from Lebanon was studied by means of GC and GC/MS analysis; 70 compounds were identified. The oil was constituted mainly by monoterpenes and the most abundant components were -pinene, spathulenol and carvacrol. Nepeta glomerata oil showed antibacterial activity, particularly towards Gram-positive bacteria, and also inhibited LPS-induced NO production in macrophage cell line RAW 264.7, with an IC50 value of 78.1 mu g mL-1. Furthermore, an invitro cytotoxic assay showed that the oil was more active on a renal adenocarcinoma cell line (48% of inhibition of proliferation at 100 mu g mL-1) in comparison to an amelanotic melanoma.

The essential oil of aerial parts of Salvia lanigera Poir. (Lamiaceae) growing wild in Cyprus was obtained by hydrodistillation and was analysed by GC and GC-MS. A total of 67 compounds, representing 93.6% of the oil, were identified, and the major components were showed to be thymol (12.1%), hexadecanoic acid (6.0%), carvacrol and α-thujone (5.7%). The essential oil was assayed for its antioxidant and antimicrobial activities. Antimicrobial activity of the oil, evaluated using the broth dilution method, resulted higher against Gram-positive bacteria than the other referenced strains tested. Antioxidant activity of the oil was evaluated by using DPPH and FRAP methods together with three antioxidant standards, L-ascorbic acid, tert-butyl-4-hydroxy toluene (BHT) and gallic acid. The activity of the sample in both methods was higher than that of all of standards used at the same dose.

Teucrium divaricatum Sieb. ssp. villosum (Celak.) Rech. fil. is a medicinal plant used in Lebanon. The hydrodistillation of the aerial parts of T. divaricatum yielded 0.27% (wt/wt) of essential oil; gas chromatography and gas chromatography/mass spectrometry analysis enabled the identification of 60 compounds representing 94.5% of the total oil. On the whole, the oil was constituted mainly by sesquiterpenes (64.6%), particularly sesquiterpene hydrocarbons (50.0%). The most abundant compounds were (E)-caryophyllene (30.1%) and caryophyllene oxide (6.1%). The in vitro activity of the essential oil against some microorganisms in comparison with gentamicin by the broth dilution method was determined. The oil exhibited a good activity as an inhibitor of growth of Gram-positive bacteria.

From the aerial parts of Scutellaria hastifolia, family Lamiaceae (Labiatae), seven neo-clerodane diterpenoids (hastifolins A–G) were isolated. The products are similar to the known scuteparvin and are characterized by being trans-cinnamoyl derivatives. Structures and stereochemistry were determined by intensive NMR investigation. Six of the products form three pairs of epimers at C-13. Hastifolins A–C showed significant antifeedant activity.

Sideritis italica (Miller) Greuter et Burdet (Lamiaceae), widely used in ethnopharmacological medicine, occurs in Southern Italy and Sicily. The phytochemical composition of the essential oils of S. italica flowers and leaves, harvested in Piano Battaglia (Sicily), was analysed by GC and GC-MS. Of the 51 compounds, 43 in the oil from flowers and 29 in the oil from leaves were identified. Kaur-15-ene (20.0%) was recognised as the main constituent of the oil from flowers, together with beta-cubebene (12.1%), beta-pinene (8.5%), (Z)-nuciferol (6.5%), tricyclene (4.5%) and alpha-bisabolol (4.0%). In the oil from leaves, p-methoxyacetophenone (26.0%) prevailed, as did hexadecanoic acid (21.3%), followed by nonanal (4.8%), alpha-bisabolol (4.5%) and beta-cubebene (4.7%).

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, δ-cadinene and γ-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.

Aim of the study: Salvia bracteata Banks et Sol. and Salvia rubifolia Boiss. are known in folk medicine of Lebanon for the treatment of microbial infections, cancer, urinary and pulmonary problems. In the present study the chemical composition and antimicrobial activity of essential oils from aerial parts of Salvia bracteata and Salvia rubifolia collected in Lebanon were evaluated. The oils were also tested for their potential antiproliferative effects against M14 human melanoma cells.Material and methods: The oils were studied by GC and GC-MS and their antibacterial activity (MIC and MBC) was tested against ten bacteria species using the broth dilution method. The inhibitory effect on human melanoma cells (measurement of cell vitality, cell membrane integrity and genomic DNA fragmentation) was studied using MTT assay, calculation of LDH release and COMET assay.Results: The oils showed a good antibacterial activity (MIC = 50 mu g/ml) against Gram+ bacteria. They besides exhibited an inhibitory effect on the human cancer cells examined inducing also apoptotic cell death, but the oil of Salvia rubifolia was significantly (p<0.001) more active as compared to the oil of Salvia bracteata.Conclusion: The results on the pharmacological activities of these Salvia species provide an in vitro scientific support for the use of these plants in traditional herbal preparations. (C) 2009 Elsevier Ireland Ltd. All rights reserved.

The occurrence of diterpenoids in the essential oils of the species of the genus Stachys (Lamiaceae, Labiatae) is reviewed. The genus Stachys is one of the largest representative genera of the Lamiaceae (Labiatae) family, and includes about 300 species (1-4), in the subtropical and tropical regions of both hemispheres. A large number of essential oils were obtained by hydrodistillation of species of Stachys . The investigations on the chemical composition of these oils were strongly expanded in the last ten years by developed GC-MS analysis techniques. Obviously monoterpenoids and sesquiterpenoids are the prevailing constituents. However, in some oils the occurrence of diterpenoids was observed as quite minor constituents or traces; usually these products were merely identified but not isolated. The present review aims to collect data on their occurrence, usually difficult to be extrapolated from the single original papers. Most of the works were contributed by researchers from Greece, Turkey, Iran and Balkanic countries. In this review we report papers in which the occurrence of diterpenoids was observed. The apparent absence of diterpenoids in several species can depend on their occurrence in so small traces or on the sensitivity of the instruments used for the analysis. The diterpenoids identified in each species are reported in Table 1, quoting for the same species the contributions of more researchers whereas in Table 2 the diterpenoids are listed with species in which they occur. In total, forty-five diterpenoids were detected, showing different skeleta (e.g. labdane, abietane, kaurane, pimarane) from thirty species and subspecies of Stachys .

Scutellaria is a genus of the Lamiaceae family with about 300 species widespread in temperate regions and on tropical mountains, whose essential oils possess ecological properties such as anti-feedant [1]. Scutellaria brevibracteata Stapf. is a species typical of Lebanon whose chemical composition or biological activity were never previously studied. Therefore, in this communication we report on the study of the chemical composition of the essential oil of this plant collected in June 2007 on Mont Chabrouh in Lebanon, on rocky ground at 1500m a. s.l., and on its activity against the feeding and oviposition behaviour of Spodoptera littoralis, a polyphagous insect attacking a number of plant species. The oil was isolated by hydrodistillation [2]. GC and GC/MS analyses evidenced the presence of 48 compounds; the most abundant components were sesquiterpenes (24.9%), particularly sesquiterpenes hydrocarbons (17.3%). Caryophyllene (14.4%) was recognized as the main constituent together with hexadecanoic acid (12.6%), phytol (10.7%) and 4-vinylguaiacol (10.2%). Binary choice bioassays were undertaken to investigate if the essential oil could modulate the feeding behaviour of final stadium larvae of S. littoralis; data show that S. brevibracteata essential oil did not significantly modulate larval feeding behaviour but deterred the ovoposition behaviour of adult moths.

The genus Scutellaria comprises about 300 species of herbs or subshrubs and rarely shrubs, some of which with ecological properties such as anti-feedant and anti-fungal [1]. These properties are often due to the presence of essential oils [2]. Scutellaria hastifolia L. (leafy skullcap) is a perennial gramineous plant with the running rhizome; it is a rare species in Lithuania, where is called Ieçialape kalpoke and grows in meadows (often in the water-meadows) and riversides [3]. No report on the essential oil of this species has been found in the literature so far, therefore in this communication we describe the volatile compounds of S. hastifolia collected in Lithuania on June 2007 and its activity against the feeding and egg laying behaviour of Spodoptera littoralis, a polyphagous insect attacking a number of plant species. The oil was isolated by hydrodistillation [4]. The GC and GC/MS analyses evidenced the presence of 50 compounds, accounting for 92.1% of the oil that consisted mainly of terpenoids, particularly sesquiterpenes (61.5%), among which sesquiterpenes hydrocarbons (44.9%) prevailed over oxygen containing sesquiterpenes (16.6%). The most representative compounds were caryophyllene (12.9%), germacrene D (7.7%), caryophyllene oxide (6.9%), hexadecanoic acid (6.3%) and hexahydrofarnesylacetone (5.6%). Binary choice bioassays were undertaken to investigate if the essential oil could modulate the feeding behaviour of final stadium larvae of S. littoralis.

The chemical composition of the essential oil obtained from aerial parts of Teucrium maghrebinum growing wild in Algeria was analyzed by GC and GC-MS. Among the 66 identified compounds, delta-cadinene (12.7%), germacrene D (11.4%), gamma-cadinene (9.5%) and 4-vinyl guaiacol (4.0%) were the most abundant. The oil is strongly characterized by the presence of sesquiterpenes (61.5%), particularly hydrocarbon sesquiterpenes (49.6%).

The chemical composition of the essential oils of two Nepeta species collected in Lebanon was studied by means of GC and GC-MS analysis. The essential oil from N. curviflora Boiss. contained high amounts of beta-caryophyllene (41.6%), caryophyllene oxide (9.5%), (E)-beta-farnesene (6.2%) and (Z)-beta-farnesene (4.8%); in the oil from N. nuda L. subsp. albiflora (Boiss.) Gams. collected in Laklouk the main compounds were beta-bisabolene (11.8%), pulegone (10.8%), (E, Z)-nepetalactone (8.0%), (E)-beta-farnesene (7.1%) and caryophyllene oxide (6.9%), while N. nuda L. subsp. albiflora collected in Tannourine Cedar Forest contained high percentages of hexadecanoic acid (10.1%), beta-bisabolene (7.8%), caryophyllene oxide (7.3%), pulegone (7.2%) and (E,Z)-nepetalactone (4.4%). The effects of the essential oils on germination and initial radical elongation of Raphanus sativus L. (radish) and Lepidium sativum L. (garden cress) were studied, resulting in a significant inhibitory activity against radical elongation of the species tested.

The chemical composition of essential oils of six Stachys species, S. cretica L. ssp. vacillans Rech. fil., S. germanica L., S. hydrophila Boiss., S. nivea Labill., S. palustris L. and S. spinosa L., obtained by hydrodistillation, was studied by GC and GC–MS. All the oils have in common a great percentage of fatty acids and esters (24.2–58.5%) and a high amount of sesquiterpenes (16–35.9%), with the exception of the oil from S. palustris, which consisted mainly of carbonylic compounds (25.4%). The antioxidant activity by DPPH test and the antiproliferative activity on a series of human cancer cell lines (C32, amelanotic melanoma and ACHN, renal cell adenocarcinoma) were investigated for all the oils. S. palustris, S. cretica and S. hydrophila showed the highest antiradical effect, with IC50 values of 0.482, 0.652 and 0.664mg/ml, respectively. The most antiproliferative essential oil against C32 cell line was the oil of S. germanica with a 77% of inhibition at a concentration of 100μg/ml. S. germanica, S. palustris and S. spinosa showed the most antiproliferative activity on ACHN cell line, at a concentration of 100μg/ml,with 81%, 77% and 73% inhibition, respectively.