Comparison of composition and antifungal activity of Artemisia argyi Lévl. et Vant inflorescence essential oil extracted by hydrodistillation and supercritical carbon dioxide

Essential oil of Artemisia argyi Lévl. et Vant inflorescence was obtained by supercritical CO(2) extraction and hydrodistillation. The oil was analyzed by gas chromatography/mass spectrometry to characterize its components and was also tested for antifungal activity. A total of 61 compounds were identified in the hydrodistilled oil. The major components were 1,8-cineole (4.46%), borneol (3.58%), terpinol (10.18%), spathulenol (10.03%), caryophyllene oxide (6.51%), juniper camphor (8.74%), Camazulene (2.05%), and camphor (3.49%). By using supercritical CO(2) at 50 degrees C and 10 MPa, the concentrations of previous main components were lower than oil obtained by hydrodistillation, while miscellaneous compounds were higher. The essential oil extracted by these two methods exhibited antifungal activity against Botrytis cinerea and Alternaria alternate, two common storage pathogens of fruits and vegetables. The inhibition of B. cinerea and A. alternate were 93.3 and 84.7% for oil extracted by hydrodistillation when exposed to a concentration of 1,000 mg L(-1), while values of 70.8 and 60.5% were observed from oil extracted by supercritical CO(2).     

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.     

Essential oil composition of four endemic Ferulago species growing in Turkey

The essential oils from aerial parts of Ferulago pachyloba (Fenzl) Boiss., F. platycarpa Boiss. & Bal., F. isaurica Penmen, and F. longistylis Boiss. (Apiaceae) were obtained by hydrodistillation and analyzed by GC and GC-MS. The highest oil yield (1.50%) was obtained from F. pachyloba followed by F. longistylis (0.16%), F. isaurica (0.08%) and F. platycarpa (0.07%). Fifty-three compounds were identified in the oil of F. pachyloba with (Z)-beta-ocimene (25.7%) and alpha-pinene (9.8%) as main constituents; sixty-seven in the oil of F. platycarpa with 2,3,6-trimethylbenzaldehyde (29.8%) and cis-chrysanthenyl acetate (24.2%) as main components; seventy-eight in the oil of F. isaurica with nonacosane (25.5%) and hexadecanoic acid (14.8%) as main constituents; and fifty-nine in the oil of F. longistylis with 2,3,6-trimethylbenzaldehyde (32.7%) and bornyl acetate (12.6%) as main components. Quantitative and qualitative differences in the oil compositions of these four species were observed.     

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.     

Chemical composition and antimicrobial activity of essential oil of Heracleum rigens

The essential oil was extracted from the seeds of Heracleum rigens by hydrodistillation and a total of twenty compounds accounting for 98.5% of the total oil composition were identified. Physicochemical properties and chemical composition of the oil was determined by a combination GC/FID and GC/MS analysis. The major compounds identified were bornyl acetate (51.2%), alpha-pinene (22.6%), limonene (9.62%), octyl acetate (3.94%), rho-cymene (2.85%) and gamma-terpinene (1.93%). The antimicrobial activity of the oil was screened by the disc diffusion method against nine pathogenic bacterial strains. Maximum antimicrobial activity was noted against Klebsiella pneumonia and Bacillus subtillis. This investigation corroborates the traditional claim of H. rigens as an effective antimicrobial agent.     

Contribution to the analysis of the essential oil of Helichrysum italicum (Roth) G. Don. Determination of ester bonded acids and phenols

The essential oil of Helichrysum italicum (Roth) G. Don (everlasting or Immortelle essential oil) was isolated by hydrodistillation and analysed by GC and GCMS. Forty four compounds were identified. The main components were alpha-pinene(12.8%), 2-methyl-cyclohexyl pentanoate (11.1 %), neryl acetate (10.4%), 1,7-di-epi-alpha-cedrene (6.8%) and other compounds. The oil was fractionated and ester-containing fraction was hydrolysed with KOH/H(2)SO(4). The liberated volatiles were analysed by GC and GC-MS: three phenols and twenty seven volatile carboxylic acids were identified[70% low fatty acids (C(2)-C(5)), 15% C(10)-C(12) acids and 15% other acids]. The main acids were acetic acid (24.3%) propanoic acid (17.2%), 2-methylpropanoic acid (11.4%),dodecanoic acid (8.7%), 2-methylbutanoic acid (8.3%), (Z)-2-methylbutenoic acid(5.1%) and decanoic acid (4.6%). With respect to the identified bonded carboxylic acids,the minimal number of esters in the oil was twenty seven, but their overall quantity was probably larger due to different possible combinations of alcohols with acids to form esters. On the other hand, only six main esters were identified in the oil before fractionation and hydrolysis.     

Comparison of different extraction methods for the analysis of volatile secondary metabolites of Lippia alba (Mill.) N.E. Brown, grown in Colombia, and evaluation of its in vitro antioxidant activity

Hydrodistillation (HD), simultaneous distillation solvent extraction (SDE), microwave-assisted hydrodistillation (MWHD), and supercritical fluid (CO2) extraction (SFE) were employed to isolate volatile secondary metabolites from fresh leaves and stems of Colombian Lippia alba (Mill.) N.E. Brown. Kovàts indices, mass spectra or standard compounds were used to identify around 40 components in the various volatile fractions. Carvone (40-57%) was the most abundant component, followed by limonene (24-37%), bicyclosesquiphellandrene (5-22%), piperitenone (1-2%), piperitone (ca. 1.0%), and beta-bourbonene (0.6-1.5%), in the HD, SDE, MWHD, and SFE volatile fractions. Static headspace (S-HS), simultaneous purge and trap in solvent (CH2Cl2) (P&T), and headspace solid-phase microextraction (HS-SPME) were used to sample volatiles from fresh L. alba stems and leaves. The main components isolated from the headspace of the fresh plant material were limonene (27-77%), carvone (14-30%), piperitone (0.3-0.5%), piperitenone (ca. 0.4%), and beta-bourbonene (0.5-6.5%). The in vitro antioxidant activity of L. alba essential oil, obtained by hydrodistillation was evaluated by determination of hexanal, the main carbonyl compound released by linoleic acid subjected to peroxidation (1 mm Fe2+, 37 degrees C, 12 h), and by quantification of this acid as its methyl ester. Under the same conditions, L. alba HD-essential oil and Vitamin E exhibited similar antioxidant effects.     

Essential oil composition of Nepeta satureioides from Iran

The essential oil of Nepeta satureioides Boiss. from Iran was isolated by hydrodistillation in yield of 0.06% (w/w). The chemical composition of the essential oil was analyzed by GC and GC-MS. Forty-five compounds accounting for 97.4% of the total oil were identified. The major components were linalool (23.8%), (Z,E)-farnesol (14.7%), linalyl acetate (11.1%), β-caryophyllene (6.6%), lavandulol acetate (6.6%), caryophyllene oxide (6.4%), and (Z)-β-farnesene (3.4%). Oxygenated terpenoids were the main group of compounds. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 144–145, March–April, 2006.     

Chemical composition of essential oil from Jordanian Lupinus varius L.

The chemical composition of essential oil obtained by hydrodistillation from flowering shoots of Lupinus varius L. was analyzed by GC–FID and GC–MS. Chemical analysis of this oil showed that it includes a complex mixture of aldehydes, alcohols, esters and mono- and sesquiterpenes. Forty one compounds were characterized in the oil. The major components of the oil were 6,10,14-trimethyl-2-pentadecanone (20.5%), pentadecanal (10.2%), (E) nerolidol (8.43%), carracol ethyl ether (4.3%), α-humulene (3.6%), (2Z,13E)-ocatadeca-2,13-dien-l0-ol (3.2%) and caryophyllene-5-ol (2.7%).     

Chemical composition of the essential oil of Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon

The essential oil of aerial parts of Salvia multicaulis Vahl. var. simplicifolia Boiss. (Lamiaceae) growing wild in Lebanon was obtained by hydrodistillation and was analysed by GC and GC-MS. 67 compounds constituting 95.2% of the oil were identified, the major components being alpha-copaene (8.0%), alpha-pinene (6.6%), myrtenol (5.7%), trans-sabinyl acetate (5.3%).     

Chemical composition and antimicrobial activity of essential oils from Centaurea pannonica and C. jacea

The chemical composition and antimicrobial activity of the essential oils obtained by hydrodistillation from Centaurea pannonica (Heufel) Simonkai and C. jacea L. (Asteraceae), were investigated. The essential oils were analyzed by GC and GC-MS. Forty five and twenty nine compounds were identified in the two oils, respectively. C. pannonica oil was rich in fatty acids (43.7%), with 9-octadecanoic acid (34.0%) and (Z,Z)-9,12-octadecadienoic acid (8.6%) as the major compounds. In contrast, the essential oil of C. jacea was dominated by oxygenated sesquiterpenes (43.2%), among which caryophyllene oxide (23.5%) and spathulenol (8.9%) were the major constituents. However, the oil was also characterized by an important fatty acid fraction (15.5%), with 9-octadecanoic acid (8.9%) and hexadecanoic acid (6.6%) being the main components. The antimicrobial activities of the essential oils were evaluated by the microdilution method against three Gram-positive and three Gram-negative bacteria, and one yeast. Both oils exhibited significant antimicrobial activity, especially against Gram-positive bacteria.     

Essential oil composition of three Australian endemic species of Darwinia (Myrtaceae)

The essential oils from the aerial parts of three rare Australian endemic species of Darwinia have been extracted by hydrodistillation and analyzed by gas chromatography (GC) and gas chromatography coupled to mass spectrometry (GC-MS). In D. procera, myrtenyl acetate (6.1-29.6%), alpha-pinene (6.9-25.1%), gamma-terpinene (6.2-13.6%), bicyclogermacrene (5.5-10.8%) and (E)-nerolidol (3.4-9.7%) were the principal components detected. D. fascicularis ssp. fascicularis produced an oil in which (E)-nerolidol (33.0%), alpha-pinene (15.1%) and gamma-terpinene (10.2%) were the principal components. In D. peduncularis the major constituents were alpha-pinene (33.5%), gamma-terpinene (23.1%) and bicyclogermacrene (6.7%).     

Volatile constituents of aerial parts of three endemic Centaurea species from Turkey: Centaurea amanicola Hub.-Mor., Centaurea consanguinea DC. and Centaurea ptosimopappa Hayek and their antibacterial activities

The volatile constituents of the aerial parts of Centaurea amanicola Hub.-Mor., Centaurea consanguinea DC. and Centaurea ptosimopappa Hayek were extracted by hydrodistillation and analysed by GC and GC-MS. Altogether 94 components were identified. Sesquiterpenoids, fatty acids and carbonylic compounds were the most abundant components in the oils. Hexadecanoic acid and (Z,Z )-9,12-octadecadienoic acid were the main fatty acids in all the examined samples, that showed different patterns of composition. The study on the biological activity of the oils showed an action mainly against the Gram-positive pathogens.     

Composition and enantiomeric analysis of the essential oil of the fruits and the leaves of Pistacia vera from Greece

The essential oils of the fruits and the leaves of pistachio (Pistacia vera L.) were analyzed by GC and GC/MS. Fresh unripe pistachio fruits were richer in essential oil (0.5%, w/w) than the leaves (0.1%, w/w). Twenty one compounds were identified in the essential oil of the fruits and the major components were (+)-alpha-pinene (54.6%) and terpinolene (31.2%). The enantiomeric ratio of the major constituents of the essential oil of the fruits was determined using chiral GC/MS and it was found that the (+)/(-)-alpha-pinene ratio was 99.5:0.5, (+)/(-)-limonene 80:20, (+)/(-)-beta-pinene 96:4, and (+)/(-)-alpha-terpineol 0:100. Thirty three compounds were identified in the essential oil of the leaves and the major components were found to be alpha-pinene (30.0%), terpinolene (17.6%) and bornyl acetate (11.3%).     

Hydrodistillation-headspace solvent microextraction, a new method for analysis of the essential oil components of Lavandula angustifolia Mill

A new method involving concurrent headspace solvent microextraction combined with continuous hydrodistillation (HD-HSME) for the extraction and pre-concentration of the essential oil of Lavandula angustifolia Mill. into a microdrop is developed. A microdrop of n-hexadecane containing n-heptadecane (as internal standard) extruded from the needle tip of a gas chromatographic syringe was inserted into the headspace above the plant sample. After extraction for an optimized time, the microdrop was retracted into the syringe and injected directly into a GC injection port. The effects of the type of extracting solvent, sample mass, microdrop volume and extraction time on HD-HSME efficiency were investigated and optimized. Using this method, thirty-six compounds were extracted and identified. Linalool (32.8%), linalyl acetate (17.6%), lavandulyl acetate (15.9%), alpha-terpineol (6.7%) and geranyl acetate (5.0%) were found to be the major constituents. To the best of our knowledge this is the first report on the use of continuous headspace solvent microextraction coupled with hydrodistillation for investigation of essential oil components.     

Combined analysis by GC (RI), GC-MS and 13C NMR of the supercritical fluid extract of Abies alba twigs

Two samples (leaves and twigs) of Abies alba Miller from Corsica were extracted using supercritical CO2 and their chemical compositions were compared with those of the essential oils obtained from the same batch of plant material. In total 45 components were identified using combined analysis by GC (RI), GC-MS and 13C NMR. It was observed that the contents of monoterpenes (mainly represented by limonene, alpha-pinene and camphene) were significantly lower in the supercritical fluid extract (SFE) than in the essential oil (EO). Conversely, the proportions of sesquiterpenes were much higher in CO2 extracts than in essential oils (around 30% vs 4%). Cis-abienol, a diterpene alcohol, was identified only in SFE, and the proportions of this constituent (7.5% and 17.3%) were determined using quantitative 13C NMR since it was under estimated using the standard conditions of GC.     

Volatile organic compounds from Centaurium erythraea Rafn (Croatia) and the antimicrobial potential of its essential oil

GC and MS were used for the analysis of Croatian Centaurium erythraea Rafn essential oil (obtained by hydrodistillation) and headspace (applying headspace solid-phase microextraction). The headspace contained numerous monoterpene hydrocarbons (the major ones were terpinene-4-ol, methone, p-cymene, γ-terpinene and limonene). Oxygenated monoterpenes were present in the headspace and oil, while 1,8-cineole, bornyl acetate and verbenone were present only in the headspace. High headspace percentages of toluene and naphthalene were found, followed by hemimellitene. Lot of similarities were observed with Serbian C. erythraea oil [neophytadiene (1.4%), thymol (2.6%), carvacrol (6.1%) and hexadecanoic acid (5.7%)], but different features were also noted such as the presence of menthol, menthone and phytone. The oil fractionation enabled identification of other minor compounds not found in total oil such as norisoprenoides, alk-1-enes or chromolaenin. The essential oil showed antimicrobial potential on Escherichia coli, Salmonella enteritidis, Staphylococcus aureus and Bacillus cereus. On the other hand, no antibacterial activity of the oil was observed on Pseudomonas fluorescens and Lysteria monocytogenes.     

Chemical composition and bioactivity of Citrus medica L. cv. Diamante essential oil obtained by hydrodistillation, cold-pressing and supercritical carbon dioxide extraction

The chemical composition of the essential oil of Citrus medica L. cv. Diamante peel obtained by hydrodistillation, cold-pressing and supercritical carbon dioxide extraction techniques was determined by GC/MS analysis. Forty-six components were fully characterised. Limonene and γ-terpinene were the major components of the oils obtained by hydrodistillation (HD) and cold-pressing (CP), while citropten was the major constituent in the oil obtained by supercritical carbon dioxide extraction (SFE). Acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities were evaluated. The essential oil obtained by hydrodistillation exerted the highest inhibitory activity against BChE (IC?? value of 154.6 μg mL?1) and AChE (IC?? value of 171.3 μg mL?1. Interestingly, the oil obtained by cold-pressing exhibited a selective inhibitory activity against AChE. The essential oils have also been evaluated for the inhibition of NO production in LPS induced RAW 264.7 macrophages. The oil obtained by hydrodistillation exerted a significant inhibition of NO production with an IC?? value of 17 μg mL?1 (IC?? of positive control 53 μg mL?1).     

气相色谱/质谱法分析柏树叶挥发油的化学成分

采用水蒸气蒸馏技术提取了3种柏树叶的挥发油,经气相色谱/质谱分析,共分离和鉴定了64种化学成分,其主要成分为萜烯类,其他成分为烷烃类、醇类、酚类和酯类等。其中圆柏树叶中分离鉴定出33种挥发性成分,主要萜类为桧烯(20.99%)和柠檬烯(19.78%);中山柏树叶中分离鉴定出37种挥发性成分,主要为α-蒎烯(10.39%)、桧烯(11.19%)和δ-3-蒈烯(8.88%);龙柏树叶中分离鉴定出37种挥发性成分,主要为柠檬烯(24.56%)和β-月桂烯(8.04%)。分离鉴定出3种柏树叶的共有成分14种。     

川芎水蒸气蒸馏和超临界CO2提取物化学成分的GC-MS分析鉴别

用水蒸气蒸馏和超临界CO2提取方法对川芎药材中的化学成分进行提取,用气相色谱-质谱联用技术(GC-MS)对提取物进行分析,分别鉴定出30和34个化合物,测定了其相对含量。 结果表明,水蒸气蒸馏和超临界CO2提取物的主要成分均为(Z)-藁本内酯。 超临界CO2提取方法能提取出较多的川芎药效物质,如丁基酞内酯、丁烯基酞内酯、川芎内酯A、(Z)-藁本内酯、(E)-藁本内酯和川芎内酯I。 而水蒸气蒸馏提取物中除了川芎药效物质外,还含有较多的萜烯类化合物。 结果表明,超临界CO2对川芎药效物质的提取比水蒸气蒸馏法的效率高。 通过对川芎中带不饱和侧链与饱和侧链内酯类化合物质谱裂解规律的解析归纳,鉴别了川芎中不饱和侧链内酯类化合物如(Z)-藁本内酯、(E)-藁本内酯、丁烯基酞内酯和川芎内酯I以及饱和侧链内酯类化合物如丁基酞内酯和川芎内酯A。