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.     

Comparative essential oil composition of aerial parts of Tanacetum dumosum Boiss. from Southern Zagros,Iran.

The essential oils of leaves and flowers of Tanacetum dumosum Boiss., an endemic medicinal shrub, were extracted by using hydrodistillation method and analysed using GC and GC–MS. A total of 43 and 44 compounds were identified in the essential oils from the leaves and flowers of T. dumosum, respectively. The major chemical constituents of leaves oil were borneol (27.9%), bornyl acetate (18.4%), 1,8-cineol (17.5%), α-terpineol (5.3%), cis-chrysanthenyl acetate (3.3%), camphene (2.7%) and terpinene-4-ol (1.9%), while the main components of the flower oil were isobornyl-2-methyl butanoate (41.1%), trans-linalyl oxide acetate (11.9%), 1,8-cineole (7.7%), thymol (4.2%), linalool (3.9%), camphor (2.9%), isobornyl propanoate (2.9%), α-terpineol (2.1%) and caryophyllene oxide (2.0%). Major qualitative and quantitative variations for some main chemical compounds among different aerial parts of T. dumosum were identified. High contents of borneol, bornyl acetate, 1,8-cineol and linalool in the leaves and flowers of T. dumosum show its potential for use in the food and perfumery industry.     

Distribution and chemical polymorphism of the essential oils of Achillea cartilaginea growing wild in Lithuania

The essential oils from 14 Achillea cartilaginea samples (leaves and flowers) collected from natural habitats in Lithuania were analysed by GC-MS. In total, 97 compounds were identified, 69 of which have not been reported previously in this species. In general, the essential oils of A. cartilaginea were rich in oxygenated monoterpenes. Remarkable chemical polymorphism was observed within the population of A. cartilaginea in Lithuania. It was observed that 1,8-cineole, camphor, cis-chrysanthenol, β-thujone, sabinol, chrysanthenone, terpinen-4-ol, bornyl acetate and β-sesquiphellandrene were the major constituents in the oils of the analysed plants. Hierarchical cluster analysis, which was based on the 19 major components exceeding 5% in the total oil, indicates the presence of several main chemical groups in the analysed plant populations.     

Volatile constituents and antioxidant activity of flowers, stems and leaves of Nasturtium officinale R. Br

GC-MS analyses of the essential oils of leaves, stems and flower of Nasturtium officinale resulted in the identification of 9, 8 and 15 compounds, representing 97%, 100% and 94.7% of the oils, respectively. The main compounds of the oil of leaves were myristicin (57.6%), α-terpinolene (8.9%) and limonene (6.7%). Caryophyllene oxide (37.2%), p-cymene-8-ol (17.6%), α-terpinolene (15.2%) and limonene (11.8%) were the main components in stems, whereas limonene (43.6%), α-terpinolene (19.7%), p-cymene-8-ol (7.6%) and caryophyllene oxide (6.7%) were the major constituents in the oil of flowers. All the samples were subjected to a screening for their possible antioxidant activities using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and β-carotene-linoleic acid assays. In the above tests, methanol extracts of leaves showed higher antioxidant activity than the oils and methanol extracts of stems and flowers.     

The essential oil constituents and antimicrobial activity of Anthemis aciphylla BOISS. var. discoidea BOISS

The essential oil of aerial parts, leaves and flowers of the endemic Anthemis aciphylla BOISS. var. discoidea BOISS. (Asteraceae) were obtained by hydrodistillation. The oils were analyzed both by GC and GC-MS on a polar column. The monoterpenes alpha-pinene (9-49%) and terpinen-4-ol (22-32%) were characterized as the main constituents. An unknown component isolated from the essential oil was characterized by means of MS, HR-MS, FT-IR, 1D- and 2D-NMR techniques as isofaurinone (1). Furthermore, the biological activity of the essential oils was evaluated in various human pathogenic microorganisms using the broth microdilution method. Weak to moderate inhibitions (0.06-1.0 mg/ml) was observed.     

Volatile constituents of Origanum vulgare L., 'thymol' chemotype: variability in North India during plant ontogeny

Essential oils derived from six different phenophases, namely early vegetative stage, late vegetative stage, early flowering stage, full flowering stage (FFS), late flowering stage and seed shattering stage of Origanum vulgare L. grown in Kumaon region of Uttarakhand, India were investigated by GC and GC-MS. A total of 38 constituents, representing 97.4-99.7% of the total oil composition, were identified. Major components of oils were thymol (40.9-63.4%), p-cymene, (5.1-25.9%), γ-terpinene (1.4-20.1%), bicyclogermacrene (0.2-6.1%), terpinen-4-ol (3.5-5.9%), α-pinene (1.6-3.1%), 1-octen-3-ol (1.4-2.7%), α-terpinene (1.0-2.2%), carvacrol (<0.1-2.1%), β-caryophyllene (0.5-2.0%) and β-myrcene (1.2-1.9%). Thymol, terpinen-4-ol, 3-octanol, α-pinene, β-pinene, 1,8-cineole, α-cubebene and (E)-β-ocimene were observed to be higher during FFS. The study showed that plant stage had a significant effect on the essential oil content and composition of O. vulgare grown in the hilly tracks of Northern India.     

Essential oil of Nepeta x faassenii Bergmans ex Stearn (N. mussinii Spreng. x N. nepetella L.): a comparison study

Analysis (GC and GC/MS) of an essential oil sample obtained from dry leaves of Nepeta x faassenii Bergmans ex Steam, a hybrid species produced by crossbreeding N. mussinii Spreng. with N. nepetella L., led to the identification of 109 constituents that represented 95.9% of the oil. The major constituents were 4aalpha,7alpha,7aalpha-nepetalactone (67.8%), 1,8-cineole (6.6%), germacrene D (4.8%), beta-pinene (2.7%), (E)-beta-ocimene (2.6%), 4aalpha,7beta,7aalpha-nepetalactone (2.3%) and (E)-beta-farnesene (1.0%). Chemical composition of the oil was compared, using multivariate statistical analyses (MVA) with those of the oils of other Nepeta taxa, in particular N. mussinii and N. nepetella. This was done in order to explore the mode of inheritance of the monoterpene biosynthetic apparatus of N. faassenii. Chemical composition of the volatiles of a Nepeta taxon (different populations) can be subject to variation due to environmental and geographical factors. To accommodate this fact in the MVAs, along side with N. faassenii essential oil, additional 6 oils (3 different populations of N. nuda L. and N. cataria L. from Serbia) were included in this study (isolated and analyzed (chemically and statistically)). The MVA analyses recognized N. faassenii as being closely related to both N. mussinii and N. nepetella. If the relative content of oil constituents per plant and not per chromatogram were used as variables in the MVA (this was done by simple multiplication of the yields and relative percentages of components) a higher degree of mutual similarity (in respect to the monoterpene biosynthesis) of N. faassenii to N. mussinii, than to the other parent species, was observed.     

Antimicrobial activity and chemical constituents of the essential oils from flower, leaf and stem of Gypsophila bicolor from Iran

The volatile constituents from flower, leaf and stem of Gypsophila bicolor growing in Iran were obtained by hydrodistillation and analyzed by GC and GC/MS. The flower oil was characterized by high amounts of germacrene-D (21.2%), p-cymene (20.6%), bicyclogermacrene (17.6%), gamma-dodecadienolactone (13.7%) and terpinolene (9.4%). Twenty-four constituents representing 97.4% of the leaf oil were identified of which germacrene-D (23.4%), terpinolene (14.5%), bicyclogermacrene (7.5%), gamma-dodecadienolactone (6.8%), p-cymene (6.7%) and cis-beta-ocimene (6.3%) were major components. The main components of the stem oil were gamma-dodecadienolactone (28.5%), bicyclogermacrene (14.8%), germacrene-D (12.6%), p-cymene (12.5%), terpinolene (11.6%) and trans-beta-ocimene (4.2%). The antimicrobial effects of flower, leaf and stem essential oils from Gypsophila bicolor were studied according to the agar diffusion cup method. The essential oils had a moderate effect on the Gram-positive and Gram-negative bacteria, but had a substantial effect on the fungi studied.     

Major constituents and anthelmintic activity of volatile oils from leaves and flowers of Cymbopogon martini Roxb

The major volatile constituents of leaves and flowers of Cymbopogon martini from the volatile oil obtained by steam distillation were identified by GC/MS. Five constituents were identified from the volatile oil of leaves and flowers, which constituted about 82.49 and 75.63% of the total amount, respectively. A monoterpene, piperitone (6.00%), was identified in the flowers of C. martini; in addition, flowers were found to contain more olefinic terpenes, namely geraniol (69.63%), compared with leaves (53.41%). Leaves contain bicyclic monoterpene, nerol (24.76%) and alpha-pinene (4.32%). Anthelmintic activity of these oils was evaluated on adult Indian earthworms Pheretima posthuma and results showed that the volatile oil of C. martini flower required less time to cause paralysis and death of the earthworms.     

Chemical composition and antioxidant activities of essential oil of Hedychium greenii and Hedychium gracile from India

The chemical constituents of the essential oils hydrodistilled from rhizome parts of Hedychium greenii W.W. Sm. and Hedychium gracile Roxb, of family Zingiberaceae, growing in India, were analysed for the first time by GC-FID and GC-MS, respectively. A total of 30 and 29 components representing 99.62 and 96.74% of the total oil were identified in the essential oils of H. greenii and H. gracile, respectively. The major components of H. greenii were bornyl acetate (31.32%), α-pinene (14.49%), camphene (12.81%) and limonene (10.55%), whereas H. gracile was dominated by β-pinene (25.24%), γ-terpinene (24.62%), terpinen-4-ol (14.87%) and 1,8-cineole (7.51%). Essential oils were assessed for antioxidant potential using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical scavenging assay. H. greenii oil exhibited stronger antioxidant potential as compared to H. gracile oil and butylated hydroxytoluene (BHT). Thus, H. greenii rhizome oil has the potential to be used as an alternative source of antioxidant.     

Micromorphology of glandular hairs, biological activity and composition of the essential oil of Tanacetum fisherae (Asteraceae-Anthemideae) from Iran

The essential oil was obtained from the aerial flowering parts of Tanacetum fisherae, a new record from Iran, by hydrodistillation and analyzed by GC and GC-MS. Eleven components representing 99.9% of the total oil were identified. 1,8-Cineole (79.9%) was characterized as the principal compound. The essential oil and its main component were tested against nine microbial strains. The result of the bioassays revealed that the oil possess potent antimicrobial property. This may be associated due to the presence of 1,8-cineole in the oil which tested individually and its high activity was observed. Micromorphological studies of hairs by scanning electron microscopy (SEM) exhibited the presence of abundant sessile capitate glandular and medifixed T-shaped eglandular trichomes on the leaves, flowers and achene, giving useful diagnostic characters for identification of this medicinal plant.     

Composition of the Essential Oils of Two Endemic Species from Turkey: Achillea lycaonica and A. ketenoglui

The hydrodistilled essential oils ofAchillea lycaonicaBoiss. & Heldr. andA. ketenogluiH. Duman were analyzed by GC/MS. The main components in the oils were trans-sabinene hydrate (9.3%) inA. lycaonicaand borneol (14.1%) and terpinen-4-ol (14.5%) inA. ketenoglui     

Essential oil composition, antimicrobial and cytotoxic activities of two endemic Stachys cretica subspecies (Lamiaceae) from Turkey

The chemical compositions of the water-distilled essential oil of Stachys cretica ssp. lesbiaca Rech. fil. and S. cretica ssp. trapezuntica Rech. fil. were determined by GC and GC-MS. Altogether 63 compounds were identified. The sesquiterpene hydrocarbon, germacrene D (20.3% and 12.9% respectively) was the main component identified in both oils. Furthermore, ethanol, light petroleum, dichloromethane, ethyl acetate and n-butanol extracts prepared from the aerial parts of the plants were tested for their antimicrobial activities against six bacterial strains and the yeast Candida albicans. The extracts exhibited no antibacterial activity, but the light petroleum and n-butanolic fractions showed low antifungal activities. Crude ethanolic extracts of the two subspecies were tested for their ability to inhibit the growth of HL-60 and Ishikawa human tumor cell lines. The IC50 values were 100 microg/mL for the HL-60 cell line and 200 microg/mL for the Ishikawa cell line.     

Seasonal variation in the chemical composition and antimicrobial activity of volatile oils of three species of Leptospermum (Myrtaceae) grown in Brazil

This study investigates the seasonal variation of three species of Leptospermum (Myrtaceae) grown in Brazil. The chemical composition of the volatile oils of L. flavescens and L. petersonii did not show any significant seasonal variation in the major components, while for Leptospermum madidum subsp. sativum the levels of major constituents of the volatile oils varied with the harvest season. Major fluctuations in the composition of L. madidum subsp. sativum oil included α-pinene (0-15.2%), β-pinene (0.3-18.5%), α-humulene (0.8-30%), 1,8-cineole (0.4-7.1%) and E-caryophyllene (0.4-11.9%). Levels of β-pinene (0.3-5.6%), terpinen-4-ol (4.7-7.2%) and nerolidol (55.1-67.6%) fluctuated seasonally in the L. flavescens oil. In L. petersonii, changes were noted for geranial (29.8-32.8%), citronellal (26.5-33.9%) and neral (22.7-23.5%). The activity of the volatile oils against the tested bacteria differed, depending on season the oils were obtained. In general, the volatile oils were more active against Gram-positive bacteria.     

Essential oil analysis and antibacterial activity of Rosmarinus tournefortii from Algeria

The volatile compounds obtained by hydrodistillation of the aerial parts of Rosmarinus tournefortii De Noé. growing wild in the occidental region of Algeria were analyzed by GC/MS. Thirty-six compounds were characterized representing 95.6% of the essential oil, with camphor (37.6%), 1,8-cineole (10.0%), p-cymene-7-ol (7.8%), and borneol (5.4%) as the major components. The antimicrobial activity was evaluated against three pathogenic bacteria: Gram-negative (Escherichia coli and Pseudomonas aeruginosa) and Gram-positive (Staphylococcus aureus). The minimum inhibitory concentration (MIC; mg/mL) was determined by sub-culture on Muller Hinton agar plates. The essential oil exhibited strong antibacterial activity against E. coli and P. aeruginosa, and was also active against Staphylococcus aureus.     

Essential oil composition and antibacterial activity of Monticalia greenmaniana (Asteraceae)

The essential oils from fresh aerial parts of Monticalia greenmaniana (Hieron) C. Jeffrey (Asteraceae) collected in March, were analyzed by GC/MS. Oil yields (w/v) of 0.1% (flowers), 0.07%, (stems) and 0.1% (leaves) were obtained by hydrodistillation. Thirteen, sixteen and eighteen components, respectively, were identified by comparison of their mass spectra with those in the Wiley GC-MS Library data base. The major components of the flower and stem oils were 1-nonane (38.8% flowers; 33.5% stems), alpha-pinene (29.0% flowers; 14.8% stems) and germacrene D (15.6% flowers; 18.6% stems). However, in the leaf oil, germacrene D was observed at 50.7%, followed by beta-cedrene at 8.4%. The leaf essential oil showed a broad spectrum of antibacterial activity against the important human pathogenic Gram-positive and Gram-negative bacteria Staphylococcus aureus (ATCC 25923), Enterococcus faecalis (ATCC 19433), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853) and Klebsiella pneumoniae (ATCC 25955) with MIC values ranging from 75 to 6000 ppm.     

Chemical composition of the resin essential oil of Canarium album from Vietnam

The composition of the essential oil obtained from the resin of Canarium album (Lour.) Raeusch, Burseraceae, growing in Vietnam, was studied by GC and GC/MS. Twenty-nine compounds representing 95.2% of the oil were identified. Monoterpenoids made up 93.2% of the oil, with β-pinene (33.3%), α-terpinene (19.4%), γ-terpinene (14.1%), and terpinen-4-ol (11.9%) as the main components. Sesquiterpenoids made up 2.0% of the oil, and the content of each individual was below 0.5% of the oil. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 421–422, September–October, 2006.     

Composition of essential oils from <Emphasis Type="Italic">Salvia anatolica</Emphasis>, a new species endemic from Turkey

The component composition of essential oils produced by steam distillation from flower heads, leaves, and stems of Salvia anatolica (Lamiaceae), a recently described new species endemic from Turkey, was studied by GC/FID and GC/MS. A total of 127 volatile components representing 96% of the oil was identified in essential oil from flower heads and leaves. It was found that the principal oil components of flower heads and leaves were α-pinene (10.9%), β-pinene (6.7%), α-copaene (6.3%), heptacosane (6.2%), and hexadecanoic acid (5.0%). A total of 109 volatile compounds representing 87.9% of the oil was characterized in essential oil isolated from stems. The principal oil components of stems were identified as hexadecanoic acid (27.2%), tetradecanoic acid (15.2%), dodecanoic acid (5.5%), and α-copaene (5.0%). __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 552–555, November–December, 2007.     

Chemical composition and antibacterial activity of essential oils from leaves, stems and flowers of Salvia reuterana Boiss. grown in Iran

The essential oils obtained by hydrodistillation of the leaves, stems and flowers of Salvia reuterana (Lamiaceae) were analysed by GC and GC/MS. Germacrene D and beta-caryophyllene were the major constituents in all the three oils: (28.5, 27.7 and 32.5%) and (15.5, 11.4 and 16.6%), respectively. Bicyclogermacrene (10.2 and 13.2%) was also prodominated in the stem and flower oils. The composition of the oils was mostly quantitativel rather than qualitatively different. All the oils consisted mainly of sesquiterpenes and a small percentage of non-terpenoid compounds. In all the three oils, monoterpenes were in a concentration less than 0.5%. Antibacterial activity was determined by the measurement of growth inhibitory zones.     

Essential Oil Composition of <Emphasis Type="Italic">Nepeta involucrata</Emphasis> from Iran

The essential oil of Nepeta involucrata (Bunge) Bornm. (Lamiaceae) obtained by hydrodistillation from the aerial parts during the flowering stage was analyzed by GC and GC-MS. Forty-eight compounds representing 97.2% of total oil were identified. The main compounds of the oil were 1,8-cineol (23.1%), germacrene-D (15.1%), and β-pinene (12.2%). No traces of nepetalactone isomers were found as oil constituents. __________ Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 562–564, November–December, 2005.