Chemical diversity of the essential oils of twenty populations of Tanacetum polycephalum Sch. Bip. from Iran

Chemical diversity of the essential oils of twenty wild populations of Tanacetum polycephalum Sch. Bip., was investigated. The aerial parts of T. polycephalum were collected at full flowering stage from West Azerbaijan Province of Iran, air-dried; hydrodistilled to produce essential oils. The essential oils were analyzed by GC-FID and GC-MS. A total of forty compounds were identified accounting for 96.4–99.9% of the total oils. The most principal compounds were cis-thujone (0–82.3%), trans-thujone (0–79.8%), camphor (1.3–75.0%), 1,8-cineole (4.5–43.3%), borneol (1.0–36.2%) and bornyl acetate (0–26.8%). Hierarchical cluster analysis based on the percentages (>0.5%) of the essential oils components was carried out to determine the chemical diversity among the populations studied. The cluster analysis resulted in the identification of four main chemotypes namely: ‘camphor + 1,8-cineole’, ‘mixed’, ‘cis-thujone’ and ‘trans-thujone’.     

Composition of essential oils from four Apiaceae and Asteraceae species growing in Uzbekistan

The chemical composition of essential oils isolated from the aerial parts of Heracleum lehmannianum, Prangos pabularia, Pseudohandelia umbellifera and Pulicaria salviifolia, all of them growing in Uzbekistan, were determined by GC-MS analysis. The main components of the oil from H. lehmannianum were α-phellandrene (10.5%), 1-butanol (9.0%), δ-cadinene (6.2%), α-cadinol (5.7%), τ-muurolol (3.1%), 4-terpineol (2.4%) and α-muurolene (2.6%), while cis-allo-ocimene (17.6%), δ-3-carene (14.2%), limonene (7.6%), 2,4,6-trimethylbenzaldehyde (6.8%), α-terpinolene (6.1%), β-ocimene (4.3%), α-ocimene (4.2%), α-phellandrene (4.2%) were the major oil components in P. pabularia, and borneol (4.4%), t-cadinol (4.1%), α-humulene oxide (4.0%), caryophyllene oxide (3.6%), bornyl chloride (3.1%), β-pinene (2.9%) in P. umbellifera. The essential oil of P. salviifolia had a much more complex composition which was dominated by 4-terpineol (13.4%), α-cadinol (5.7%), 6-epi-shyobunol (5.2%), γ-terpinene (5.0%), δ-cadinene (4.4%), α-terpinene (3.5%).     

Study of quantitative and qualitative variations in essential oils of Sicilian Rosmarinus officinalis L.

In this study the chemical characterisation of 10 Sicilian Rosmarinus officinalis L. biotypes essential oils is reported. The main goal of this work was to analyse the relationship between the essential oils yield and the geographical distribution of the species plants. The essential oils were analysed by GC-FID and GC-MS. Hierarchical cluster analysis and principal component analysis statistical methods were used to cluster biotypes according to the essential oils chemical composition. The essential oil yield ranged from 0.8 to 2.3 (v/w). In total 82 compounds have been identified, these represent 96.7–99.9% of the essential oil. The most represented compounds in the essential oils were 1.8-cineole, linalool, α-terpineol, verbenone, α-pinene, limonene, bornyl acetate and terpinolene. The results show that the essential oil yield of the 10 biotypes is affected by the environmental characteristics of the sampling sites while the chemical composition is linked to the genetic characteristics of different biotypes.     

Study on essential oils from the leaves of two Vietnamese plants: Jasminum subtriplinerve C.L. Blume and Vitex quinata (Lour) F.N. Williams

The essential oil constituents of the leaves of Jasminum subtriplinerve (Oleaceae) and Vitex quinata (Verbanaceae) cultivated in Vietnam were analysed by gas chromatography – flame ionisation detector (GC–FID) and gas chromatography – mass spectrometry (GC–MS) techniques. The main constituents identified in J. subtriplinerve were mainly oxygenated monoterpenes represented by linalool (44.2%), α-terpineol (15.5%), geraniol (19.4%) and cis-linalool oxide (8.8%). The quantitative significant components of V. quinata were terpene hydrocarbons comprising of β-pinene (30.1%), β-caryophyllene (26.9%) and β-elemene (7.4%). The chemical compositions of the essential oils are being reported for the first time.     

Essential Oil of Arischrada korolkowii from the Chatkal Mountains of Uzbekistan

The herbal parts of Arischrada korolkowii (Regel et Schmalh.) Pobed. (Lamiaceae) growing in Uzbekistan were hydrodistillated to yield 1.1% of essential oil. The essential oil was analyzed by GC/MS. Eighty eight compounds were characterized representing 98% of the essential oil with 1,8-cineole (29.3%), camphor (9.8%), -caryophyllene (8.5%), bornyl acetate (7.7%), caryophyllene oxide (7.2%), and borneol (5.6%) as the main constituents.     

Antibacterial activity and GC/MS analysis of the essential oils from flower, leaf and stem of Origanum vulgare ssp. viride growing wild in north-west Iran

Essential oils obtained from flowers, leaves and stems of Origanum vulgare L. ssp. viride (Boiss.) Hayek., growing wild in Ardabil Province (north-west Iran), were analyzed by GC and GC/MS. beta-Caryophyllene was the major constituent in all three oils (48.1%, 50.1% and 60.2%, respectively). Of the 19 components detected in the flower oil, comprising 96.3% of the total, the major components were 1,8-cineole (11.6%), alpha-pinene (6.9%), and gamma-cadinene (4.8%). 1-Octen-3-ol (23.8%), and 1,8-cineole (8.5%) predominated in the leafoil. In the stem oil, other main constituents were bicyclogermacrene (9.8%), 1,8-cineole (6.4%), borneol (5.1%), and pinocarvone (4.4%). The essential oils were evaluated for their antibacterial activity against 10 selected microorganisms. The data obtained contribute to the future use of certain essential oils as natural preservatives for food products, due to their safety and positive effect on shelf life.     

Essential Oil Profile and Yield of Corolla,Calyx, Leaf,and Whole Flowering Top of Cultivated Lavandula angustifolia Mill. (Lamiaceae) from Utah

Lavandula angustifolia Mill. (lavender) is an essential-oil-bearing plant in the Lamiaceae family. Volatile oil produced through the steam distillation of lavender was examined to establish the essential oil yield and aromatic profile from each portion of the plant—namely, the corolla, calyx, leaf, and whole flowering top. The resulting essential oils were analyzed by GC-FID and GC-MS. The different plant parts generally shared similar compounds but in varying relative percentages. Aromatic profiles of the whole flowering top and calyx were similar, with prominent compounds being linalool acetate (34.3%, 32.0%), linalool (26.5%, 32.9%), lavandulyl acetate (5.6%, 4.9%), terpinen-4-ol (5.3%, 7.0%), and (Z)-β-ocimene (4.5%, 5.4%), respectively. Aromatic profiles for the corolla and leaf were unique. Prominent aromatic compounds of the corolla included linalool acetate (18.4%), linalool (10.8%), epi-α-cadinol (10.0%), borneol (7.3%), and lavandulyl acetate (6.3%). Prominent aromatic compounds of the leaf included epi-α-cadinol (19.8%), γ-cadinene (11.0%), borneol (6.0%), caryophyllene oxide (4.9%), and bornyl acetate (4.8%). Complete profiles and essential oil yields of corolla, calyx, leaf, and whole flowering top were established. This study establishes the influence the corolla, calyx, and leaf exert on the aromatic profile of the whole flowering top and provides insight into authentication of lavender essential oil.     

Essential oil composition of aerial parts of Micromeria persica Boiss. from Western of Shiraz,Iran

Micromeria persica Boiss. is medicinal and aromatic plant, belonging to the Lamiaceae family. The chemical composition of the essential oils (EOs) from aerial parts of M. persica were extracted using hydro-distillation method and analysed using GC and GC–MS. Fifty-two compounds were identified in the EOs of aerial parts of M. persica. The main chemical compositions were n-hexadecanoic acid (14.9%), thymol (9.5%), linoleic acid (8.0%), carvacrol (5.6%), (E)-nerolidol (5.5%), linolenic acid (5.5%), α-cadinol (2.7%), linalool (2.7%), borneol (2.6%), caryophyllene oxide (2.3%) and pulegone (2.0%). Presence of borneol, thymol, carvacrol and pulegone suggests the potential of this plant as a flavouring source in the food industry, being used in perfumery and cosmetics industry, vitamin E synthesis and exhibit strong fungicidal, antibacterial and antimicrobial activities.     

Essential oil of <Emphasis Type="Italic">Laurus nobilis</Emphasis> from Montenegro

Steam distilled oil from the shoots, separated leaves, and stem, as well as from the flower of laurel (Laurus nobilis), grown in Montenegro, were analyzed by GC and GC/MS. The yield of essential oil was as follow: 1.4% in young shoots, 1.5% in the separated leaves, and 0.7% in separated stems. The main constituents of all investigated oils were 1,8-cineole, methyleugenol, and α-terpinyl acetate. Besides, α-pinene, β-pinene, sabinene, and linalool were also present. It was interesting and important for commercial samples of laurel essential oil that there was no significant difference among the essential oil obtained from young shoots and those obtained from leaves and stem. The main constituents of the flower oil were 1,8-cineole (15.7%), β-caryophyllene (9.5%), γ-muurolene (7.1%), α-terpinyl acetate (6.5%), and methyleugenol (3.9%). Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 337–339, July–August, 2007.     

Composition and in vitro cytotoxic activities of essential oil of Hedychium spicatum from different geographical regions of western Himalaya by principal components analysis

The rhizome of Hedychium spicatum has been widely used in traditional medicines. The present study deals with the evaluation of the cytotoxic potential of rhizome essential oils from four different regions of the Western Himalaya (India) along with comparative correlation analysis to characterise the bioactive cytotoxic component. The essential oils were coded as MHS-1, MHS-2, MHS-3 and MHS-4, and characterised using GC-FID and GC–MS. The main volatile compounds identified were 1,8-cineol, eudesmol, cubenol, spathulenol and α-cadinol. In vitro cytotoxic activities were assessed against human cancer cell lines such as, the lung (A549), colon (DLD-1, SW 620), breast (MCF-7, MDA-MB-231), head and neck (FaDu), and cervix (HeLa). MHS-4 is significantly active in comparison to other samples against all cancer cell lines. Sample MHS-4 has major proportion of monoterpene alcohol mainly 1,8-cineol. Principal components analysis was performed for the experimental results and all four samples were clustered according to their percentage inhibition at different doses.     

Analysis of Volatile Organic Compounds from Dendranthema indicum var. aromaticum by Headspace Gas Chromatography-Mass Spectrometry and Accurate Mass Measurement

The volatile organic compounds from flowers, leaves, and stems of Dendranthema indicum var. aromaticum, obtained through a static headspace technique, were analyzed by gas chromatography-mass spectrometry (GC-MS) and accurate mass measurement. The qualitative approach, comprising accurate mass measurement, retention index, and mass spectral search, was utilized to identify compounds. A total of 162 components were identified, representing 97.55–98.72% of the volatiles of individual samples. The principal chemical components in flowers were bornyl acetate (15.40%), α-phellandrene (14.18%), p-cymene (9.64%), camphor (9.54%), β-linalool (8.61%), and α-thujone (7.06%). In leaves, the main components were p-cymene (20.42%), bornyl acetate (20.41%), α-phellandrene (13.67%), and β-linalool (5.46%). As for stems, trans-β-farnesene (17.95%), germacrene D (12.89%), β-phellandrene (12.70%), β-caryophyllene (10.18%), and bicyclogermacrene (8.01%) were the dominant volatile compounds. Comparative studies on the volatiles from various species of genus Dendranthema indicated that Dendranthema indicum var. aromaticum contains significantly more aroma compounds than its morphologically similar species.     

GC Comparative Analysis of Leaf Essential Oils from Two Myrtle Varieties at Different Phenological Stages

The essential oils obtained from leaves of two Myrtus communis varieties (baetica and italica), growing wild in North Tunisia, were investigated by GC and GC–MS at their different phenological stages. The highest essential oil yield was observed at the flowering stage with 0.6% (w/w) for italica and 0.4% (w/w) for baetica and 49 compounds were identified. The main essential oil leaf compounds of both myrtle varieties, belonging to the monoterpene class, were α-pinene, 1,8-cineole, limonene and linalool and their percentages showed significant changes during the phenological stages.

     

The Composition of the Essential Oil of Stachys iberica Subsp. Stenostachya Growing In Turkey

The water distilled essential oil from dried aerial parts ofStachys ibericasubsp.stenostachya(Lamiaceae) was analyzed by GC/MS. Seventy-one compounds were characterized representing 96% of the oil. The main constituents were found as linalyl acetate (42.2%), linalool (18.9%), geranyl acetate (8.2%), and -terpineol (5.3%).     

Rapid analysis of Achillea tenuifolia Lam essential oils by polythiophene/hexagonally ordered silica nanocomposite coating as a solid-phase microextraction fibre

In this work, a highly porous fibre coated with polythiophene/hexagonally ordered silica nanocomposite (PT/SBA-15) was prepared and used for extraction of essential oils with microwave-assisted distillation headspace solid phase microextraction (MA-HS-SPME) method. The prepared nanomaterials were immobilised on a stainless steel wire for fabrication of the SPME fibre. Using MA-HS-SPME followed by GC-MS, 24 compounds were separated and identified in Achillea tenuifolia, which mainly included limonene (28.6%), α-cadinol (12.7%), borneol (6.7%), caryophyllene oxide (3.2%), bornyl acetate (4.3%), camphene (3.2%) and para-cymene (2.3%). The experimental results showed that the polythiophene/hexagonally ordered silica nanocomposite fibres were suitable for the semi-quantitative study of the composition of essential oils in plant materials and for monitoring the variations in the volatile components of the plants.     

Constituents and antimicrobial activity of the essential oils from flower, leaf and stem of Helichrysum armenium

The chemical constituents from the flower, leaf and stem of Helichrysum armenium DC. (Asteraceae) growing in Iran were obtained by hydrodistillation and analyzed by GC and GC/MS. The oil of flower was characterized by higher amount of limonene (21.2%), alpha-cadinol (18.2%), borneol (11.9%), delta-cadinene (9.0%), bornyl acetate (8.0%) and alpha-humulene (7.3%). Twenty one constituents representing 96.2% of the chromatographical leaf oil were identified of which limonene (29.2%), alpha-pinene (14.4%), caryophyllene oxide (6.5%), alpha-gurjunene (6.3%), bornyl acetate (5.5%) and torreyol (5.2%) were the major components. The main components of the stem oil were limonene (23.6%), alpha-pinene (13.4%), spathulenol (6.4%), alpha-gurjunene (6.3%), caryophyllene oxide (5.3%), bornyl acetate (5.2%), beta-cubebene (4.8%) and delta-cadinene (4.3%). The composition of the oils is different, although the most abundant components are identical in leaf oil (96.2%). The antimicrobial effect of flower, leaf and stem essential oils from Helichrysum armenium was studied according to the agar diffusion cup method. The essential oils had a moderate effect on the Gram-positive and Gram-negative bacteria and had a substantial fungicidal effect on the fungi under study.     

Transformations of monoterpenoids in aqueous acids: The reactions of linalool. geraniol,nerol and their acetates in aqueous citric acid

The fate of linalool, geraniol and nerol and their acetates in aqueous citric and hydrochloric acids has been investigated. Linalool and linalyl acetate yield predominantly α-terpineol and 3,7-dimethyloct-1-en-3,7-diol (6). Geraniol and nerol afford α-terpineol, linalool and the isomeric 3,7-dimethyloct-2-en-1,7-diols (7 and 8). While both neryl and geranyl acetate give α-terpineol and linalool, the former affords Z-1-acetoxy-3,7-dimethyloct-2-en-7-ol (8a), and the latter the E-isomer 7a and 2β-acetoxymethyl-1α,3,3-trimethylcyclohexanol (13).     

Chemical Compositions of the Essential Oils of Stems,Leaves, and Roots of <Emphasis Type="Italic">Prangos latiloba</Emphasis>

Hydrodistilled volatile oils from crushed dry stems, leaves, and roots of Prangos latiloba Korov. (Umbelliferae) growing wild in Sabzevar (Iran) were analyzed by GC and GC/MS. Eight compounds constituting 84.72% of stem oil, twelve compounds constituting 95.39% of leaf oil, and nine compounds constituting 88.73% of root oil have been identified. The main components of stem oil were γ-cadinene (30.39%), α-pinene (25.47%), and sabinene (12.55%). The main components of leaf oil were germacrene D (27.79%), α-pinene (17.81%), β-caryophyllene (12.75%), and β-pinene (11.23%). The main components of root oil were spathulenol (29.5%), 1,8-cineol (19.42%), p-cymene (17.03%), and α-bisabolol (15.33%). __________ Published in Kimiya Prirodnikh Soedinenii, No. 5, pp. 443–444, September–October, 2005.     

Activity antifungal of the essential oils; aqueous and ethanol extracts from Citrus aurantium L.

Our study is about the essential oil of Citrus aurantium L. in Tunisia and its plant extract. The yield of this essential oil is 0, 56% but the yield of the extract of plant was 17.1% for the aqueous extract ant 18.3% for the ethanolic extract. The analysis of chemical composition by using GC and GC/MS showed the essential oil of C. aurantium L. species to be rich in monoterpenes such as α-terpineol, lianolyl acetate, linalool and limonene. The antifungal activity of this oil showed us an inhibition of the germination of mushrooms, in the same way we could note that the biologic activities are generally assigned to the chemotypes high content in oxygenated monoterpene.     

Chemical Composition of Natural Hydrolates and Their Antimicrobial Activity on Arcobacter-Like Cells in Comparison with Other Microorganisms

Hydrolates obtained via the hydrodistillation and steam distillation of Lavandula angustifolia Mill., Syzygium aromaticum L., Foeniculum vulgare Mill., and Laurus nobilis L. were analyzed by gas chromatography with flame ionization detector (GC-FID) and gas chromatography coupled to mass spectrometry (GC-MS). Additionally, the hydrolates were evaluated for antimicrobial activity (disk-diffusion and microdilution method), influence on biofilm formation (Christensen method) and cytotoxicity of concentrated hydrolates against human cell lines (A549) by xCELLigence system. Using chemical analysis, 48, 9, 13 and 33 different components were detected in lavender, clove, fennel and laurel hydrolates, respectively. Lavender hydrolate contained the largest proportion of 1,8-cineol, linalool furanoxide, and linalool. The main components of laurel hydrolate were 1,8-cineol, 4-terpineol and α-terpineol. Fenchone and estragole were the most abundant in fennel hydrolate, and eugenol and eugenyl acetate in clove hydrolate. Concentrated hydrolates showed significant antimicrobial activity. Clove hydrolate was among the most antimicrobially active agents, most preferably against C. albicans, with an inhibition zone up to 23.5 mm. Moreover, concentrated hydrolates did not show any cytotoxic effect again8 st human A549 cells. In the presence of the non-concentrated hydrolates, significantly reduced biofilm formation was observed; however, with concentrated clove hydrolate, there was an increase in biofilm formation, e.g., of A. thereius, A. lanthieri, and A. butzleri. Research shows new findings about hydrolates that may be important in natural medicine or for preservation purposes.     

Volatile constituents of flowers and leaves of Anthemis hyalina

The chemical composition of the essential oils of the flowers and leaves of Anthemis hyalina were analyzed by GC and GC-MS for the first time. The oils were found to contain seventy-two components. cis-Chrysanthenyl acetate (14.9% and 17.8%), camphor (11.6% and 1.7%), terpinen-4-ol (8.3% and 1.2%), germacrene-D (5.1% and 2.1%), β-caryophyllene (4.1% and 5.4%), myrcene (3.6% and 16.9%), bicyclogermacrene (3.5% and 0.9%), α-pinene (2.3% and 4.1%), cis-β-ocimene (2.1% and 4.3%) and isospathulenol (0.4% and 4.3%) were found to be the major constituents of the oils of flowers and leaves respectively. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 428–429, September–October, 2006.