Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish artemisia species

The compositions of essential oils isolated from the aerial parts of Artemisia absinthium, Artemisia santonicum, and Artemisia spicigera by hydrodistillation were analyzed by GC-MS, and a total of 204 components were identified. The major components of these essential oils were camphor (34.9-1.4%), 1,8-cineole (9.5-1.5%), chamazulene (17.8-nd%), nuciferol propionate (5.1-nd%), nuciferol butanoate (8.2-nd%), caryophyllene oxide (4.3-1.7%), borneol (5.1-0.6%), alpha-terpineol (4.1-1.6%), spathulenol (3.7-1.3%), cubenol (4.2-0.1%), beta-eudesmol (7.2-0.6%), and terpinen-4-ol (3.5-1.2%). The antifungal activities of these essential oils were tested against 11 plant fungi and were compared with that of a commercial antifungal reagent, benomyl. The results showed that all of the oils have potent inhibitory effects at very broad spectrum against all of the tested fungi. Pure camphor and 1,8-cineole, which are the major components of the oils, were also tested for antifungal activity against the same fungal species. Unlike essential oils, these pure compounds were able to show antifungal activity against only some of the fungal species. In addition, the antioxidant and DPPH radical scavenging activities of the essential oils, camphor, and 1,8-cineole were determined in vitro. All of the studied essential oils showed antioxidant activity, but camphor and 1,8-cineole did not.     

Composition, enantiomeric distribution, and antibacterial activity of the essential oil of Achillea ligustica All. from Corsica

The essential oil of Achillea ligustica from Corsica was investigated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 82 compounds representing 94.0% of the oil were tentatively identified. The main constituents were the camphane derivatives, representing >30% (camphor, 21.3%; borneol, 6.2%; bornyl acetate, 3.5%) of the whole oil, and santolina alcohol (19.3%). The enantiomeric distribution of 8 chiral constituents was determined by GC-MS using two enantioselective stationary phases (DIME-beta-CD and Lipodex-E). Racemic santolina alcohol, required for optimization of the enantioselective GC conditions, was prepared by an original two-step synthesis from 2,5-dimethylhexa-2,4-diene. The whole essential oil was tested for its antibacterial activity against a wide range of bacteria using a paper disk method. The results show a promising activity against Streptomyces species.     

Chemical composition and antioxidant, antimicrobial, and antifungal activities of the essential oil of Achillea ligustica all

The chemical composition of the essential oil from flowering tops of Achillea ligustica All. was studied. Samples were collected in different localities of Sardinia (Italy) and hydrodistilled both with Clevenger-type and with simultaneous distillation-extraction apparatus. The yields ranged between 0.88 +/- 0.06 and 0.43 +/- 0.02% (vol/dry wt). The essential oils were analyzed by GC-MS, and a total of 96 components were detected. From a qualitative point of view, irrelevant differences between samples were observed. Strong chemical variability depending on the origin of the samples was observed. The major compounds found were santolina alcohol (6.7-21.8%, for the first time detected in A. ligustica), borneol (3.4-20.8%), sabinol (2.1-15.5%), trans-sabinyl acetate (0.9-17.6%), alpha-thujone (0.4-25.8%), and, among sesquiterpenes, viridiflorol (0.7-3.6%). No significant differences were detected between essential oils extracted by hydrodistillation and simultaneous distillation-extraction with CH2Cl2 and n-hexane. Antioxidant activity as DPPH radical scavenging activity was expressed in TEAC and ranged between 0.40 and 0.88 mmol/L. The antimicrobial and antifungal activities were investigated on Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, Penicillium commune, Fusarium oxysporum, Rizoctonia solani, and Aspergillus flavus, showing low activity.     

Chemical composition and larvicidal activity of the essential oils from Eupatorium betonicaeforme (D.C.) Baker (Asteraceae)

The volatile composition of the essential oils from leaves and roots of Eupatorium betonicaeforme (D.C.) Baker was analyzed by GC-MS. A total of 12 compounds were identified. beta-Caryophyllene (12.4-41.7%), alpha-humulene (11.7-14.6%), gamma-muurolene (10.4-19.0%), bicyclogermacrene (15.0-17.5%), 2,2-dimethyl-6-vinylchroman-4-one (10.3-25.5%), and 2-senecioyl-4-vinylphenol (8.5-41.0%) were the most prominent constituents. The former two compounds were isolated and characterized by spectroscopic data. The essential oils and the isolated compounds were tested against Aedes aegypti larvae survival. The results obtained show that the essential oil from roots and 2,2-dimethyl-6-vinylchroman-4-one (10.3-25.5%) could be considered as natural larvicidal agents.     

Chemical composition and antifungal activity of Salvia macrochlamys and Salvia recognita essential oils

Essential oils of Salvia macrochlamys and Salvia recognita were obtained by hydrodistillation of dried aerial parts and characterized by gas chromatography and gas chromatography-mass spectrometry. One hundred and twenty identified constituents representing 97.7% in S. macrochlamys and 96.4% in S. recognita were characterized, and 1,8-cineole, borneol, and camphor were identified as major components of the essential oils. The oils were evaluated for their antimalarial, antimicrobial, and antifungal activities. Antifungal activity of the essential oils from both Salvia species was nonselective at inhibiting growth and development of reproductive stroma of the plant pathogens Colletotrichum acutatum, Colletotrichum fragariae, and Colletotrichum gloeosporioides. S. macrochlamys oil had good antimycobacterial activity against Mycobacterium intracellulare; however, the oils showed no antimicrobial activity against human pathogenic bacteria or fungi up to a concentration of 200 microg/mL. S. recognita oil exhibited a weak antimalarial activity against Plasmodium falciparum.     

Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens

The volatile metabolites of Salvia fruticosa plants, growing wild in 15 localities scattered across Greece, were analyzed by means of GC and GC-MS. The essential oil content ranged from 0.69 to 4.68%, and the results of the analyses showed a noticeable variation in the amounts of the five main components [1,8-cineole, alpha-thujone, beta-thujone, camphor, and (E)-caryophyllene]. The antifungal activities of the essential oils from two localities, belonging in two different groups of cluster and principal component analysis, and their main components (1,8-cineole and camphor) were evaluated in vitro against five phytopathogenic fungi. Both oils were slightly effective against Fusarium oxysporum f. sp. dianthi and Fusarium proliferatum, whereas against Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium solani f. sp. cucurbitae the oils exhibited high antifungal activities.     

Composition and antifungal activity on soil-borne pathogens of the essential oil of Salvia sclarea from Greece

The hydrodistilled essential oils of the aerial parts of wild-growing Salvia sclarea originated from two localities in Greece were analyzed by GC-MS. Sixty-six compounds, representing 93.26-98.19% of the oils, were identified. Linalyl acetate (19.75-31.05%), linalool (18.46-30.43%), geranyl acetate (4.45-12.1%), and alpha-terpineol (5.08-7.56%) were the main components. The antifungal activity of the oil of one locality and of the main components, linalyl acetate and linalool, was evaluated in vitro against three soil-borne pathogens.     

Essential oils produced by in vitro shoots of sage (Salvia officinalis L.)

In vitro shoots of sage (Salvia officinalis L.) were established under eight different hormonal supplementations and proliferated by subculture of nodal shoot segments. The respective essential oils, obtained by hydrodistillation, were composed of more than 75 compounds, 65 of which were identified. The 10 major compounds were, by order of retention time, alpha-pinene (4.1-5.4%), camphene (6-7.1%), beta-pinene (9.3-14.5%), limonene (2-2.3%), 1,8-cineole (3.6-5.6%), (-)-thujone (13.2-16.1%), (+)-isothujone (6.6-7.4%), camphor (19.8-24%), alpha-humulene (5.1-6.8%), and manool (4.2-7.7%). Notwithstanding the eight different hormonal supplementations tested, the percentage composition of the shoot essential oils were kept in a narrow range of variation. However, the type and concentration of growth regulators apparently influenced the accumulation of essential oils. The highest accumulation of essential oils and the highest shoot biomass growth were obtained with 2.0 mg/L kinetin and 0.05 mg/L 2,4-dichlorophenoxyacetic acid.     

Effect of maturation on the composition and biological activity of the essential oil of a commercially important Satureja species from Turkey: Satureja cuneifolia Ten. (Lamiaceae)

The essential oil obtained by hydrodistillation from aerial parts of Satureja cuneifolia Ten., collected in three different maturation stages such as preflowering, flowering, and postflowering, were analyzed simultaneously by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Thymol (42.5-45.2%), p-cymene (19.4-24.3%), and carvacrol (8.5-13.2%) were identified as the main constituent in all stages. At the same time, the essential oils and main components were evaluated for their antimicrobial activity using a microdilution assay resulting in the inhibition of a number of common human pathogenic bacteria including methicillin-resistant Staphylococcus aureus (MRSA) and the yeasts Candida albicans and Candida tropicalis. The minimum inhibitory concentrations (MIC) varied between 62.5 and 250 microg/mL within a moderate antimicrobial activity range. Furthermore, the antioxidant capacity of the essential oils and major components thymol and carvacrol were examined in vitro. The essential oils obtained from S. cuneifolia in three different stages and its main components were interacted with 1,1-diphenyl-2-picrylhydrazyl (DPPH (*)) as a nitrogen-centered stable radical, resulting in IC 50 = 1.6-2.1 mg/mL. In addition, the effects on inhibition of lipid peroxidation of the essential oils were assayed using the beta-carotene bleaching method. All of the tested oils inhibited the linoleic acid peroxidation at almost the same level as butylated hydroxytoluene (BHT) (93.54-94.65%). BHT and ascorbic acid were used as positive controls in the antioxidant assays.     

Chemical composition of volatiles in Sardinian myrtle (Myrtus communis L.) alcoholic extracts and essential oils

The chemical composition of the volatile fraction of myrtle (Myrtus communis L.) alcoholic extracts and essential oils from leaves and berries collected in different places in Sardinia (Italy) was studied. A simple and rapid liquid-liquid extraction method was used to isolate volatile compounds from myrtle alcoholic extracts followed by GC and GC-MS analysis allowing the detection of 24 compounds. The volatile fraction was characterized by the terpenes fraction corresponding to that of the essential oils and by a fatty acid ethyl esters fraction. The variation during extraction of the volatile fraction in alcoholic extracts of berries and leaves was evaluated. Essential oils were obtained by hydrodistillation, and the yields were on average 0.52 +/- 0.03% (v/w dried weight) and 0.02 +/- 0.00% for leaves and berries, respectively. The essential oils were analyzed by GC and GC-MS, and a total of 27 components were detected, accounting for 90.6-98.7% of the total essential oil composition. Strong chemical variability depending on the origin of the samples was observed. The major compounds in the essential oils were alpha-pinene (30.0 and 28.5%), 1,8-cineole (28.8 and 15.3%), and limonene (17.5 and 24.1%) in leaves and berries, respectively, and were characterized by the lack of myrtenyl acetate.     

Comparison of the essential oils of Glehnia littoralis from Northern and Southern Japan.

The essential oils from aerial and root parts of Glehnia littoralis were investigated by GC and GC-MS, and 125 compounds were identified. Plants were obtained from Northern and Southern Japan, and samples from the same locations were cultivated either exposed or unexposed to sunlight. The main constituents of the essential oils were found to be alpha-pinene (0.03-13.40%), limonene (0.15-10.71%), beta-phellandrene (0.03-22.93%), germacrene B (0.27-8.33%), spathulenol (0.24-6.50%), beta-oplopenone (0.06-6.47%), panaxynol (0.38-24.58%), propyl octanoate (3.44-27.85%), hexadecanoic acid (0.45-27.80%), and linoleic acid (0.16-17.56%). Terpenoid compounds were found in higher concentrations in the Northern type oils than in the Southern types, whereas the concentration of polyacetylenic compounds was higher in one of the Southern samples, except from the aerial parts of those cultivated exposed. Consequently, the constitution of the essential oils from G. littoralis could be separated into Northern and Southern types.     

Composition of the essential oil of Citrus tamurana Hort. ex Tanaka (Hyuganatsu)

The composition of the essential oil of Citrus tamurana Hort. ex Tanaka (Hyuganatsu), isolated by the cold-pressing method, was investigated by capillary GC and GC-MS. The effects of harvesting time, degree of freshness, and size of fruits on the composition of Hyuganatsu peel oils were also determined. A total of 126 volatile constituents were confirmed in the Hyuganatsu oils. The Hyuganatsu oils contained hydrocarbons (95.95-96.95%), aldehydes (0.33-0.62%), alcohols (1.91%-2.64%), ketones (0.40-0.62%), esters (0.28-0.39%), oxides (0.04-0.06%), acids (0.01%), and trace amounts of fugenol methyl ether. Monoterpene hydrocarbons were predominant. Limonene (80.35-82.39%), gamma-terpinene (7.71-9.03%), myrcene (2.11-2.28%), linalol (1.37-2.01%), and alpha-pinene (1.17-1.43%) were the most abundant components in Hyuganatsu oils. The principal sesquiterpene hydrocarbon was trans-beta-farnesene (0.60-1.04%), and its content in Hyuganatsu oils was higher than in oils of other citrus fruits. The number of ketones and the content of l-carvone in Hyuganatsu oils were higher than in other citrus oils.     

Determination of the chemical composition and antioxidant activity of the essential oil of Artemisia dracunculus and of the antifungal and antibacterial activities of Turkish Artemisia absinthium, A. dracunculus, Artemisia santonicum, and Artemisia spicigera essential oils

The essential oil isolated from Turkish tarragon (Artemisia dracunculus) by hydrodistillation was analyzed by GC-MS. Thirty compounds representing 99.5% of total oil were identified. The predominant components in the oil were (Z)-anethole (81.0%), (Z)-beta-ocimene (6.5%), (E)-beta-ocimene (3.1%), limonene (3.1%), and methyleugenol (1.8%). The antibacterial and antifungal activities of the essential oils isolated from A. dracunculus, Artemisia absinthium, Artemisia santonicum, and Artemisia spicigera oils were also evaluated. In general, the oils exhibited potent antifungal activity at a wide spectrum on the growth of agricultural pathogenic fungi. Among the oils, the weakest antifungal activity was shown by the oil of A. dracunculus. In many cases, the oils of A. absinthium, A. santonicum, and A. spicigera completely inhibited the growth of some fungal species. As compared with antibacterial activities of all of tested oils, A. santonicum and A. spicigera oils showed antibacterial activities over a very wide spectrum. However, the essential oils tested showed lower inhibition zones than the inhibition zones of penicillin. In addition, antioxidant and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities of tarragon oil were determined, and weak antioxidant and DPPH radical scavenging activities were found in comparison to butylated hydroxytoluene.     

Relationship Between Grazing Intensity and Qualitative and Quantitative Changes in Artemisia Sieberi Besser Essential Oil Compounds in Kashan Province of Iran

The relationship between grazing intensity and qualitative and quantitative changes in Artemisia sieberi Besser essential oil compounds in Kashan province of Iran was evaluated in this study. For this purpose, vegetation sites of Artemisia sieberi under three grazing intensities (heavy, moderate, and ungrazed) with the same ecological conditions based on the distance to the water resource were selected in Kashan-Ghamsar road rangelands and near Natural Essential Oils Institute, University of Kashan, Iran. Within each site, individual plants were sampled at random in the full flowering stage in a completely randomized (CR) design with three replications. The oils were extracted by hydrodistillation of the air-dried samples and were analyzed by gas chromatography-mass spectrometry (GC-MS). The main constituents of the oils were as follows: ungrazed site; 1,8-cineol (29.9%), myrcene (14.1%), moderate grazed site; myrcene (15.9%), 1,8cineol (15.1%), Eudesm-7(11)-en-4-ol (11.1%), and heavy grazed site; 4-tepinyl acetate (23.3%), davanone (21.9%), p-cymene (19%). Among the compounds from the three sites, 4 thepenyl acetat allocated the highest amount in heavy grazed site. The analysis of essential oils showed that there were significant quantitative and qualitative differences found within the natural populations under the three different grazing sites.     

Organ- and season-dependent variation in the essential oil composition of Salvia officinalis L. cultivated at two different sites.

More than 50 compounds were identified in essential oils from stems and leaves of Salvia officinalis L. plants harvested in July, in Arouca, in northern Portugal. About 40 of those compounds were also present in flower essential oils, collected from the same plants. alpha-Thujone was the major compound, representing about 55, 30, and 18% of the essential oils from stems, leaves, and flowers, respectively. Significant percentage variations in the main compound classes of the essential oils from shoots sampled over the year were recorded at two different sites in northern Portugal. From December to April, oxygenated monoterpenes (MO) decreased from approximately 67-72% to values of 42-43% of the essential oils. During the same time interval, the percentage of monoterpene hydrocarbons (MH) rose from 8-11% to 17-22%. At both sites, sesquiterpene hydrocarbons (SH) rose from approximately 7% in February to 19-22% in April, decreasing thereafter to approximately 9% in July. Oxygenated sesquiterpenes (SO) increased from a minimum of approximately 5% in July to a maximum of 8-11% in February, decreasing thereafter. The compounds that mostly accounted for the essential oil composition variation were alpha-pinene, beta-pinene, and camphene, as MH; alpha-thujone and camphor, as MO; alpha-humulene and beta-caryophyllene, as SH; and viridiflorol, as SO.     

Chemical composition and antifungal activity of essential oils from different tissues of Japanese Cedar (Cryptomeria japonica)

In this study antifungal activities of essential oils from different tissues of Japanese cedar (Cryptomeria japonica D. Don) against four wood decay fungi and six tree pathogenic fungi were investigated. In addition, the yields of essential oils obtained by water distillation were compared and their constituents determined by GC-MS analyses. The yield of essential oils from four tissues of Japanese cedar is in the decreasing order of leaf (27.38 mL/kg) > bark (6.31 mL/kg) > heartwood (3.80 mL/kg) > sapwood (1.27 mL/kg). Results obtained from the antifungal tests demonstrate that the essential oil of Japanese cedar heartwood used against Laetiporus sulphureus and Trametes versicolor and sapwood essential oil used against L. sulphureus had strong antifungal activities at 500 mug/mL, with IC(50) values of 39, 91, and 94 microg/mL, respectively. Besides, the essential oils of Japanese cedar heartwood used against Rhizoctonia solani, Collectotrichum gloeosporioides, Fusarium solani, and Ganoderma australe had strong antifungal activities at 500 microg/mL, with IC(50) values of 65, 80, 80, and 110 microg/mL, respectively. GC-MS analyses showed that the sesquiterpene hydrocarbon compounds dominate in the essential oil from Japanese cedar heartwood, amounting to a total percentage of 82.56%, with the major compounds of delta-cadinene (18.60%), isoledene (12.41%), and gamma-muurolene (11.82%). It is proposed that the excellent antifungal activities of Japanese cedar heartwood essential oils might correlate with the presence of these compounds.     

GC-MS analysis of essential oils from some Greek aromatic plants and their fungitoxicity on Penicillium digitatum

The isolated essential oils from seven air-dried plant species were analyzed by gas chromatography-mass spectrometry (GC-MS). Thymus vulgaris (thyme), Origanum vulgare (oregano), and Origanumdictamus (dictamus) essential oils were found to be rich in phenolic compounds representing 65.8, 71.1, and 78.0% of the total oil, respectively. Origanum majorana (marjoram) oil was constituted of hydrocarbons (42.1%), alcohols (24.3%), and phenols (14.2%). The essential oil from Lavandula angustifolia Mill. (lavender) was characterized by the presence of alcohols (58.8%) and esters (32.7%). Ethers predominated in Rosmarinus officinalis (rosemary) and Salvia fruticosa (sage) essential oils, constituting 88.9 and 78.0%, respectively. The radial growth, conidial germination, and production of Penicillium digitatum were inhibited completely by oregano, thyme, dictamus, and marjoram essential oils at relatively low concentrations (250-400 microg/mL). Lavender, rosemary, and sage essential oils presented less inhibitory effect on the radial growth and conidial germination of P. digitatum. Conidial production of P. digitatum was not affected by the above oils at concentrations up to 1000 microg/mL. Apart from oregano oil, all essential oils were more effective in the inhibition of conidial germination than of radial growth. The monoterpene components, which participate in essential oils in different compositions, seem to have more than an additive effect in fungal inhibition.     

Composition of the essential oils of Thymus and Origanum species from Algeria and their antioxidant and antimicrobial activities

The composition of the essential oils of Origanum and Thymus species restricted to Algeria and the North Africa region was determined. Antioxidant and antibacterial activities of the isolated essential oils were also determined. The oils of oregano plants were strongly characterized by p-cymene (16.8-24.9%), gamma-terpinene (16.8-24.9%), thymol (8.4-36.0%), and carvacrol (1.1-29.7%), a thymol chemotype for Origanum floribundum and a alpha-terpineol chemotype for Thymus numidicus being described for the first time. The strains of Listeria monocytogenes tested were relatively resistant to the action of essential oils of either Origanum or Thymus species. All essential oils possessed antioxidant activity, but this was dependent on the specific chemical composition and the method employed to determine such activity.     

Chemical composition and mosquito larvicidal activity of essential oils from leaves of different Cinnamomum osmophloeum provenances

Chemical compositions of leaf essential oils from eight provenances of indigenous cinnamon (Cinnamomum osmophloeum Kaneh.) were compared. According to GC-MS and cluster analyses, the leaf essential oils of the eight provenances and their relative contents were classified into five chemotypes-cinnamaldehyde type, linalool type, camphor type, cinnamaldehyde/cinnamyl acetate type, and mixed type. The larvicidal activities of leaf essential oils and their constituents from the five chemotypes of indigenous cinnamon trees were evaluated by mosquito larvicidal assay. Results of larvicidal tests demonstrated that the leaf essential oils of cinnamaldehyde type and cinnamaldehyde/cinnamyl acetate type had an excellent inhibitory effect against the fourth-instar larvae of Aedes aegypti. The LC(50) values for cinnamaldehyde type and cinnamaldehyde/cinnamyl acetate type against A. aegypti larvae in 24 h were 36 ppm (LC(90) = 79 ppm) and 44 ppm (LC(90) = 85 ppm), respectively. Results of the 24-h mosquito larvicidal assays also showed that the effective constituents in leaf essential oils were cinnamaldehyde, eugenol, anethole, and cinnamyl acetate and that the LC(50) values of these constituents against A. aegypti larvae were <50 ppm. Cinnamaldehyde had the best mosquito larvicidal activity, with an LC(50) of 29 ppm (LC(90) = 48 ppm) against A. aegypti. Comparisons of mosquito larvicidal activity of cinnamaldehyde congeners revealed that cinnamaldehyde exhibited the strongest mosquito larvicidal activity.     

Chemical composition of the essential oils of Juniperus from ripe and unripe berries and leaves and their antimicrobial activity

The composition of the essential oil from ripe and unripe berries and leaves of Juniperus oxycedrus L. ssp. oxycedrus, Juniperus phoenicea ssp. turbinata and Juniperus communis ssp. communis was analyzed by GC-MS, and microbiological assays were carried out. Samples were collected in different localities (Sardinia, Italy) and hydro distilled. The yields ranged between 2.54% +/- 0.21 (v\w dried weight) and 0.04% +/- 0.00. A total of 36 components were identified. The major compounds in the essential oils were alpha-pinene, beta-pinene, delta-3-carene, sabinene, myrcene, beta-phellandrene, limonene, and D-germacrene. Both qualitative and quantitative differences between species and between different parts of the plant were observed. The essential oils and their major compounds were tested against Candida albicans, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa, and the minimum inhibitory concentration and minimum bactericidal concentration were determined. The results obtained led to a nonsignificant inhibitory effect, although all the essential oils from Juniperus phoenicea ssp. turbinata and the essential oil from leaves of Juniperus oxycedrus ssp. oxycedrus exhibited rather good or weak activity against Candida albicans and Staphylococcus aureus.