germacrene-d and caryophyllene

Ironwort (

Topics: Diterpenes; Lamiaceae; Oils, Volatile; Phytotherapy; Plant Extracts; Plants, Medicinal; Serbia; Sideritis; Teucrium

To gain insight into the differences in the composition and volatile components content in ancient

Topics: Plant Leaves; Solid Phase Microextraction; Thuja; Trees; Volatile Organic Compounds

This work represents the first multi-scale study on Teucrium fruticans L. cultivated at the Ghirardi Botanic Garden (Lombardy, Northern Italy), combining a micromorphological and a phytochemical survey on the plant's aerial parts. Micromorphological investigations, performed by Light Microscopy, Fluorescence Microscopy and Scanning Electron Microscopy, highlighted the presence of five trichomes morphotypes, distinguished by a different distribution pattern: peltates, short-stalked and ball-like medium-stalked capitates, ubiquitous on the whole plant, medium-stalked and long-stalked capitates, exclusive to the floral whorls. Both peltates and medium-stalked capitates were recognized as the main terpene production sites. Phytochemical characterization focused on the essential oils (EOs), obtained by Clevenger-type hydrodistillation in February and April 2022 and characterized by Gas Chromatography-Mass Spectrometry (GC/MS), which resulted mainly formed by sesquiterpene hydrocarbons. The February EO profile was characterized by β-caryophyllene (28.30 %) and germacrene D (19.16 %) as main compounds, while in April β-myrcene was detected at high percentage (13.77 %), in addition to the previous two components (15.72 % and 11.55 %, respectively). Literature data, dealing with the biological activities of the main oil constituents, highlighted an anti-microbial, anti-inflammatory, and anti-tumor potential, due to the high content in sesquiterpenes and, particularly, of β-caryophyllene and germacrene D.

Topics: Oils, Volatile; Sesquiterpenes; Teucrium; Trichomes

Topics: Anti-Infective Agents; Calcium; Echinacea; Gas Chromatography-Mass Spectrometry; Humans; Oils, Volatile; Steam

The chemical composition of the essential oil of

Topics: Biphenyl Compounds; Free Radical Scavengers; Gas Chromatography-Mass Spectrometry; Inhibitory Concentration 50; Malaysia; Monocyclic Sesquiterpenes; Myristicaceae; Oils, Volatile; Picrates; Polycyclic Sesquiterpenes; Sesquiterpenes, Germacrane

Hydro-distilled essential oil from leaves of

Topics: Cells, Cultured; Cytostatic Agents; Gas Chromatography-Mass Spectrometry; Humans; Lymphocytes; Micronucleus Tests; Mutagens; Oils, Volatile; Plant Leaves; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes, Germacrane; Xylopia

It is known that the first osmotic phase affects the growth rates of roots immediately upon addition of salt; thus, dissecting metabolites profiling provides an opportunity to throw light into the basis of plant tolerance by searching for altered signatures that may be associated with tolerance at this organ. This study examined the influence of salt treatment on fatty acid composition and chemical composition of the essential oil of

Topics: Aldehydes; Citrus; Fatty Acids, Monounsaturated; Lipidomics; Oils, Volatile; Plant Roots; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Sodium Chloride

Topics: Antioxidants; Artemisia; Artemisia annua; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Russia; Sesquiterpenes, Germacrane

Secretory structures are common in Asteraceae, where they exhibit a high degree of morphological diversity. The species Verbesina macrophylla, popularly known as assa-peixe, is native to Brazil where it is widely used for medicinal purposes. Despite its potential medical importance, there have been no studies of the anatomy of this species, especially its secretory structures and secreted compounds. This study examined leaves of V. macrophylla with emphasis on secretory structures and secreted secondary metabolites. Development of secretory ducts and the mechanism of secretion production are described for V. macrophylla using ultrastructure, yield and chemical composition of its essential oils. Verbesina macrophylla has a hypostomatic leaf blade with dorsiventral mesophyll and secretory ducts associated with vascular bundles of schizogenous origin. Histochemistry identified the presence of lipids, terpenes, alkaloids and mucopolysaccharides. Ultrastructure suggests that the secretion released into the duct lumen is produced in plastids of transfer cells, parenchymal sheath cells and stored in vacuoles in these cells and duct epithelial cells. The essential oil content was 0.8%, and its major components were germacrene D, germacrene D-4-ol, β-caryophyllene, bicyclogermacrene and α-cadinol. Secretory ducts of V. macrophylla are squizogenous. Substances identified in tissues suggest that both secretions stored in the ducts and in adjacent parenchyma cells are involved in chemical defence. The essential oil is rich in sesquiterpenes, with germacrene D and its derivatives being notable components.

Topics: Mesophyll Cells; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes; Verbesina

Topics: Acyclic Monoterpenes; Antioxidants; Benzothiazoles; Biphenyl Compounds; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Picrates; Plant Extracts; Polycyclic Sesquiterpenes; Scutellaria; Sesquiterpenes; Sesquiterpenes, Germacrane; Sulfonic Acids; Uzbekistan

The chemical composition of essential oil obtained from the aerial parts of Ajuga comata Stapf. was analyzed by GC and GC/MS. Thirty-seven components were identified in the oil. (E)-β-caryophyllene (30.9%), caryophyllene oxide (24.9%), (E)-β-farnesene (12.6%), β-eudesmol (3.2%), δ-cadinene (3.1%) and germacrene D (3.0%) were the main compounds in the EOs. The chemical composition of A. comata Stapf. from the Southern Zagros of Iran is reported for the first time.

Topics: Ajuga; Gas Chromatography-Mass Spectrometry; Iran; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Eudesmane; Sesquiterpenes, Germacrane

Various species of the genus Phlomis have been reported to produce metabolites demonstrating significant pharmacological efficiency. In this study, the essential oils from twelve populations of Phlomis olivieri collected from natural habitats were investigated for their chemical components. The hydrodistillated essential oil analyzed by GC-FID and GC/MS. Analyses revealed 27 compounds, constituting 90.52 - 98.51% of the essential oils. Results indicated that the major components of the essential oils from various populations of P. olivieri were germacrene D (26.54 - 56.41%), bicyclogermacrene (6.38 - 30.55%), β-caryophyllene (5.32 - 24.52%) and α-pinene (1.29 - 15.53%). Principal component analyses (PCA) was used to identify any geographical variations in essential oil composition. Notably, three groups of Iranian P. olivieri populations were determined according to the major compounds. Results of the in vitro antibacterial activity indicated that P. olivieri essential oils showed good inhibitory activities against bacteria, especially Bacillus subtilis. The results of this study gave new insights for cultivation and industrial uses of P. olivieri in Iran.

Topics: Anti-Bacterial Agents; Bacillus subtilis; Bicyclic Monoterpenes; Gas Chromatography-Mass Spectrometry; Iran; Monoterpenes; Oils, Volatile; Phlomis; Polycyclic Sesquiterpenes; Principal Component Analysis; Sesquiterpenes; Sesquiterpenes, Germacrane

Magnolia grandiflora (Magnoliaceae) is an evergreen tree with fragrant and showy flowers native to southeastern USA but widely cultivated all over the world and used in cosmetics industry in treatment of skin diseases. Here, we report on the chemical analysis of the essential oil obtained from flowers of plants cultivated in Iran, together with the evaluation of its antioxidant and cytotoxic activities. The essential oil composition was dominated by bioactive sesquiterpenes, namely β-elemene, bicyclogermacrene, germacrene D and (E)-caryophyllene. The oil exhibited moderate radical scavenging activity towards the [Formula: see text] radical, and mild non-selective inhibitory effects against A375, MDA-MB 231 and T98 G tumour cell lines. The latter were influenced by the presence of the anticancer β-elemene. These results provided new insights for potential application of M. grandiflora volatile oil in the pharmaceutical and cosmetics industry where only the non-volatile magnolol and honokiol have hitherto been fully exploited.

Topics: Antineoplastic Agents, Phytogenic; Antioxidants; Cell Line, Tumor; Flowers; Humans; Iran; Magnolia; Oils, Volatile; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

GC/FID and GC-MS analysis revealed germacrene D, bicyclogermacrene, α-cadinol and cubenol as major compounds from aril. Germacrene D, bicyclogermacrene, trans-caryophyllene and δ-elemene are major compounds in fruits. Germacrene D, spathulenol, trans-caryophyllene and caryophyllene oxide are major compounds in leaves. Furthermore, multivariate analysis revealed distinct groups between the composition of essential oils from aril and fruit, when compared with terpene production found in leaves. Lipid composition found in arils could be protected by the presence of non-oxygenated sesquiterpenes, as germacrene D and bicyclogermacrene. Chemical profiles of essential oils from the fruits, arils and leaves of Copaifera langsdorffii Desf. revealed different compositions, which could be related to environmental pressures. Thereby, non-oxygenated sesquiterpenes can also work against herbivory, pathogens and predator's attack, emphasising the importance of further studies among terpenes, ecology interactions and plant physiology.

Topics: Fabaceae; Fruit; Gas Chromatography-Mass Spectrometry; Oils, Volatile; Plant Leaves; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes

Essential oil from the leaves of Guatteria australis was obtained by hydrodistillation, analyzed by Gas Chromatography coupled to Mass Spectromery (GC-MS) and their antiproliferative, antileishmanial, antibacterial, antifungal and antioxidant activities were also evaluated. Twenty-three compounds were identified among which germacrene B (50.66%), germacrene D (22.22%) and (E)-caryophyllene (8.99%) were the main compounds. The highest antiproliferative activity was observed against NCI-ADR/RES (TGI = 31.08 μg/ml) and HT-29 (TGI = 32.81 μg/ml) cell lines. It also showed good antileishmanial activity against Leishmania infantum (IC50 = 30.71 μg/ml). On the other hand, the oil exhibited a small effect against Staphylococcus aureus ATCC 6538, S. aureus ATCC 14458 and Escherichia coli ATCC 10799 (MIC = 250 μg/ml), as well as small antioxidant activity (457 μmol TE/g) assessed through ORACFL assay. These results represent the first report regarding chemical composition and bioactivity of G. australis essential oil.

Topics: Anti-Bacterial Agents; Antineoplastic Agents, Phytogenic; Antioxidants; Antiprotozoal Agents; Guatteria; HT29 Cells; Humans; Oils, Volatile; Plant Leaves; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

Dendranthema indicum (L.) Des Moul. is a perennial herb commonly used as a traditional Chinese medicine for a long time. In this work, we took Dendranthema indicum as a target plant and two stored insects which include Tribolium castaneum and Stegobium paniceum adults as target insects. Essential oil obtained from Dendranthema indicum was analyzed by gas chromatography-mass spectrometry (GC-MS). A total of 31 components representing 92.44% of the oil were identified and the main compounds were found to be chamazulene (15.93%), β-caryophyllene (13.78%), germacrene D (9.11%), and b-cis-farnesene (6.59%). With a further isolation, three constituents were obtained from the essential oil and identified as chamazulene, β-caryophyllene and eucalyptol. Significantly, in the progress of assay, it showed that the essential oil and chamazulene exhibited stronger insecticidal and repellent activities against Stegobium paniceum than Tribolium castaneum. The results indicate that additional to its traditional use as Chinese medicinal herb, the essential oil of Dendranthema indicum aerial parts and isolated compounds have potential to be developed into natural insecticides or repellents for control of insects in stored grains.

Topics: Animals; Asteraceae; Azulenes; Coleoptera; Cyclohexanols; Drugs, Chinese Herbal; Edible Grain; Eucalyptol; Food Storage; Gas Chromatography-Mass Spectrometry; Insect Repellents; Insecticides; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

Zornia brasiliensis, popularly known as "urinária", "urinana", and "carrapicho", is a medicinal plant used in Brazilian northeast folk medicine as a diuretic and against venereal diseases. The aim of this study was to investigate the chemical composition and antitumor potential of the leaf essential oil of Z. brasiliensis. The essential oil was obtained by hydrodistillation using a Clevenger-type apparatus and analyzed by GC-MS and GC-FID. Its composition was characterized by the presence of trans-nerolidol, germacrene D, trans-caryophyllene, α-humulene, and farnesene as major constituents. In vitro cytotoxicity of the essential oil and some of its major constituents (trans-nerolidol, trans-caryophyllene, and α-humulene) was evaluated for tumor cell lines from different histotypes using the Alamar blue assay. The essential oil, but not the constituents tested, presented promising cytotoxicity. Furthermore, mice inoculated with B16-F10 mouse melanoma were used to confirm its in vivo effectiveness. An in vivo antitumor study showed tumor growth inhibition rates of 1.68-38.61 % (50 and 100 mg/kg, respectively). In conclusion, the leaf essential oil of Z. brasiliensis presents trans-nerolidol, germacrene D, trans-caryophyllene, α-humulene, and farnesene as major constituents and is able to inhibit cell proliferation in cultures as well as in tumor growth in mice.

Topics: Animals; Antineoplastic Agents, Phytogenic; Cell Proliferation; Fabaceae; Male; Melanoma, Experimental; Mice, Inbred C57BL; Monocyclic Sesquiterpenes; Oils, Volatile; Phytotherapy; Plant Extracts; Plant Leaves; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

Analysis of the morphological traits of leaves, genetic variability (analyzed by AFLP) and chemical composition of essential oils (analyzed by GC-MS) was conducted on eleven populations of the endemic Illyric-Balcanic species Teucrium arduini L. in Croatia, Bosnia and Herzegovina, and Montenegro. Average blade length and width ranged from 20.00 to 31.47mm and from 11.58 to 15.66mm, respectively. Multivariate analysis (PCA, UPGMA) of morphological traits distinguished two continental Bosnian populations from the remaining populations. AFLP analysis separated the investigated populations into two groups based primarily on geographical distance. Essential oil analysis showed a total of 52 compounds, with two chemotypes distinguished based on the essential oil profile. The first was a sesquiterpene chemotype, with β-caryophyllene, germacrene D or caryophyllene oxide as the major compounds, while the second was an oxygenated monoterpene chemotype, with pulegone and piperitone oxide as the main components. The Mantel test showed a stronger correlation between the morphological traits and AFLP than between the essential oil profile and AFLP. The test also showed a stronger association between the essential oil profile and geographical position than between the morphological traits and geographical position.

Topics: Amplified Fragment Length Polymorphism Analysis; Gas Chromatography-Mass Spectrometry; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Teucrium

This work aimed to investigate chemical composition of essential oils obtained from Zanthoxylum dissitum leaves and roots and their insecticidal activities against several stored product pests, namely the cigarette beetle (Lasioderma serricorne), red flour beetle (Tribolium castaneum) and black carpet beetle (Attagenus piceus). The analysis by GC-MS of the essential oils allowed the identification of 28 and 22 components, respectively. It was found that sesquiterpenoids comprised a fairly high portion of the two essential oils, with percentages of 74.0% and 80.9% in the leaves and roots, respectively. The main constituents identified in the essential oil of Z. dissitum leaves were δ-cadinol (12.8%), caryophyllene (12.7%), β-cubebene (7.9%), 4-terpineol (7.5%) and germacrene D-4-ol (5.7%), while humulene epoxide II (29.4%), caryophyllene oxide (24.0%), diepicedrene-1-oxide (10.7%) and Z,Z,Z-1,5,9,9-tetramethyl-1,4,7-cycloundecatriene (8.7%) were the major components in the essential oil of Z. dissitum roots. The insecticidal activity results indicated that the essential oil of Z. dissitum roots exhibited moderate contact toxicity against three species of storage pests, L. serricorne,T. castaneum and A. piceus, with LD50 values of 13.8, 43.7 and 96.8 µg/adult, respectively.

Topics: Animals; Coleoptera; Insect Repellents; Insecticides; Monocyclic Sesquiterpenes; Oils, Volatile; Plant Leaves; Plant Roots; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes; Zanthoxylum

The essential oils obtained by steam distillation from needles of six China endemic Pinus taxa (P. tabulaeformis, P. tabulaeformis f. shekanensis, P. tabulaeformis var. mukdensis, P. tabulaeformis var. umbraculifera, P. henryi and P. massoniana) were analysed by GC/MS. A total of 72 components were separated and identified by GC/MS from the six taxa. The major constituents of the essential oils were: α-pinene (6.78%-20.55%), bornyl acetale (3.32%-12.71%), β-caryophellene (18.26%-26.31%), α-guaiene (1.23%-8.19%), and germacrene D (1.26%-9.93%). Moreover, the essential oils were evaluated for antioxidant potential by three assays (DPPH, FRAP and ABTS) and tested for their total phenolic content. The results showed that all essential oils exhibited acceptable antioxidant activities and these strongly suggest that these pine needles may serve as a potential source of natural antioxidants for food and medical purposes.

Topics: Antioxidants; Bicyclic Monoterpenes; Camphanes; China; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Oxidation-Reduction; Oxidative Stress; Phenols; Pinus; Plant Leaves; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

This investigation focused on the qualitative and quantitative composition of essential oil compounds of European Origanum vulgare. Extracts of 502 individual O. vulgare plants from 17 countries and 51 populations were analyzed via GC. Extracts of 49 plants of 5 populations of Israeli Origanum syriacum and 30 plants from 3 populations of Turkish Origanum onites were included to exemplify essential oil characteristics of 'high-quality' oregano. The content of essential oil compounds of European O. vulgare ranged between 0.03% and 4.6%. The monoterpenes were primarily made up of sabinene, myrcene, p-cymene, 1,8-cineole, β-ocimene, γ-terpinene, sabinene hydrate, linalool, α-terpineol, carvacrol methyl ether, linalyl acetate, thymol and carvacrol. Among the sesquiterpenes β-caryophyllene, germacrene D, germacrene D-4-ol, spathulenol, caryophyllene oxide and oplopanone were often present in higher amounts. According to the proportions of cymyl-compounds, sabinyl-compounds and the acyclic linalool/linalyl acetate three different main monoterpene chemotypes were defined. The cymyl- and the acyclic pathway were usually active in plants from the Mediterranean climate whereas an active sabinyl-pathway was a characteristic of plants from the Continental climate.

Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Cyclohexane Monoterpenes; Cyclohexanols; Cyclohexenes; Cymenes; Eucalyptol; Europe; Monoterpenes; Oils, Volatile; Origanum; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Thymol

As a peculiar folk medicinal plant, Acanthopanax brachypus was widely used to treat various diseases in China. At present, however, there is not a good quality standard for its quality evaluation. In this study, on the basis of the validation tests of precision, stability and repeatability, the chromatographic fingerprint of A. brachypus was established by using gas chromatography (GC)-flame ionization detector (FID) and GC-MS techniques, as well as computer aided similarity evaluation system. Thirty-two different batches of samples collected from the different producing regions and the different parts of A. brachypus were studied. The results showed that the dominant constituents of all oils were monoterpenes and sesquiterpenes, as well as oxygenated monoterpenes and sesquiterpenes. The fingerprinting profiles were found to be consistent for the fresh stem bark acquired from various production areas, 48 common peaks were determined, but the relative abundance of peaks was varied. β-Pinene, linalool, p-cymene, spathulenol, camphene, endo-borneol, verbenone, β-caryophyllene, γ-terpinene, germacrene-D, camphor, β-thujone and β-cadinene were the main constituents of the fresh stem bark oil. Except for the leaf, the chemical components among different medicinal parts of fresh plant were inconsistent with the stem bark. Besides, the varieties and relative levels of chemical components in the fresh stem bark were more abundant than in the dry counterpart. The GC-MS fingerprint can be successfully applied to distinguish the substitute or adulterant, and further assess the differences of A. brachypus grown in various areas of China.

Topics: Acyclic Monoterpenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexane Monoterpenes; Cymenes; Eleutherococcus; Gas Chromatography-Mass Spectrometry; Monoterpenes; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes

The water-distilled essential oil from the aerial parts of Anthemis tricolor Boiss. (Asteraceae), an endemic taxon from Cyprus, was analysed by GC and GC-MS. The analysis revealed 40 compounds accounting for 84.5% of the oil. Muurola-4,11-diene (20.2%), β-caryophyllene (9.1%) and germacrene-D (5.5%) were the main compounds of A. tricolor. To the best of our knowledge, this is the first detailed study of the essential oil composition of A. tricolor collected from Cyprus.

Topics: Anthemis; Chromatography, Gas; Cyprus; Gas Chromatography-Mass Spectrometry; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

The chemical constituents of essential oils from the leaf, stem bark and resins of Canarium parvum Leen., and Canarium tramdenanum Dai et Yakovl. (Burseracea) grown in Vietnam are being reported. The hydrodistilled oils were analysed for their chemical constituents by means of gas chromatography-flame ionisation detector and gas chromatography coupled with mass spectrometry. The main compounds of C. parvum were β-caryophyllene (18.7%), (E)-β-ocimene (12.9%), (Z)-β-ocimene (11.9%), germacrene D (8.8%) and α-humulene (8.4%) in the leaf; β-caryophyllene (30.4%), α-copaene (20.5%) and (E)-β-ocimene (7.7%) in the stem. However, germacrene D (23.2%), α-amorphene (14.9%), α-copaene (9.8%) and β-elemene (8.6%) were present in the resin. The leaf of C. tramdenanum comprises β-caryophyllene (16.8%), α-phellandrene (15.9%), γ-elemene (13.1%) and limonene (11.8%), while limonene (25.7%), α-phellandrene (21.7%), α-pinene (12.3%) and β-caryophyllene (10.9%) were present in the stem. However, δ-elemene (14.6%) and bulnesol (16.0%) are the main constituents in the resin.

Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Burseraceae; Cyclohexane Monoterpenes; Cyclohexenes; Gas Chromatography-Mass Spectrometry; Limonene; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Leaves; Plant Oils; Plant Stems; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes; Vietnam

Pistacia palaestina Boiss. (Anacardiaceae), a sibling species of P. terebinthus also known as turpentine tree or terebinth tree, is common in the Levant region. The aphid Baizongia pistaciae L. manipulates the leaves of the plant to form large galls, which provide both food and protection for its developing offspring. We analyzed the levels and composition of mono-and sesquiterpenes in both leaves and galls of ten naturally growing trees. Our results show that monoterpene hydrocarbons are the main constituents of P. palaestina leaves and galls, but terpene levels and composition vary among trees. Despite this inter-tree variation, terpene levels and compositions in galls from different trees resemble each other more than the patterns displayed by leaves from the same trees. Generally, galls contain 10 to 60 fold higher total terpene amounts than leaves, especially of the monoterpenes α-pinene and limonene. Conversely, the leaves generally accumulate more sesquiterpenes, in particular E-caryophyllene, germacrene D and δ-cadinene, in comparison to galls. Our results clearly show that the terpene pattern in the galls is not a simple reflection of that of the leaves and suggest that aphids have a strong impact on the metabolism of their host plant, possibly for their own defense.

Topics: Animals; Aphids; Bicyclic Monoterpenes; Cyclohexenes; Israel; Limonene; Monoterpenes; Pistacia; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes

The stem-derived essential oil of Aglaia odorata Lour. was obtained by hydrodistillation using a Clevenger-type system. Gas chromatography-mass spectrometry analysis of the oil revealed the identification of 39 compounds, representing 76.4% of the oil; germacrene D (20.3%), α-humulene (17.1%), α-himachalene (12.7%) and β-caryophyllene (10.2%) were the major components. Ar-turmerone (1) and eichlerialactone (2) were isolated from the stem oil and ethanolic stem extract of this plant species, respectively. Antimicrobial activities of the oil and ethanol extract were tested against both Gram-positive and Gram-negative bacterial strains including Bacillus cereus ATCC 11778, Staphylococcus aureus ATCC 25923, Acinetobacter baumannii ATCC 19606 and Escherichia coli ATCC 25922, as well as three rice fungal pathogens Bipolaris oryzae, Pyricularia oryzae and Rhizoctonia solani using broth microdilution method. The oil and 1 exhibited significant antifungal activity against the three rice pathogens tested, whereas 2 exhibited good antibacterial activity against both the Gram-positive pathogens tested.

Topics: Aglaia; Anti-Bacterial Agents; Antifungal Agents; Gas Chromatography-Mass Spectrometry; Gram-Negative Bacteria; Ketones; Microbial Sensitivity Tests; Monocyclic Sesquiterpenes; Oils, Volatile; Oryza; Plant Stems; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Staphylococcus aureus; Stereoisomerism

The chemical composition and antimicrobial activity studies on the essential oils of Hypericum rochelii Griseb. & Schenk and Hypericum umbellatum A. Kern. have been carried out for the first time. Seventy-nine compounds were identified in the essential oil of H. rochelii with n-nonane (24.7%), β-pinene (22.4%), germacrene D (7.5%), n-undecane (6.8%) and α-pinene (5.8%) as main constituents. One hundred and twenty-six compounds were identified in H. umbellatum essential oil with germacrene D (6.1%), (E)-nerolidol (4.4%), n-nonane (4.0%), (E)-caryophyllene (3.0%) and caryophyllene oxide (3.0%) as the most abundant components. Both oils were characterized by the presence of many components which could have numerous applications in food, pharmaceutical and perfume industries. Taxa studied herein belong to the section Drosocarpium Spach, and their intrasectional placement based on the essential oil profiles was discussed. The oils were tested in a broth microdilution assay against five bacterial and two fungal strains and found to have mainly moderate antimicrobial effects.

Topics: Alkanes; Anti-Infective Agents; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Hypericum; Monoterpenes; Oils, Volatile; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

The variation of the essential-oil composition among ten wild populations of Stachys lavandulifolia VAHL (Lamiaceae), collected from different geographical regions of Iran, was assessed by GC-FID and GC/MS analyses, and their intraspecific chemical variability was determined. Altogether, 49 compounds were identified in the oils, and a relatively high variation in their contents was found. The major compounds of the essential oils were myrcene (0.0-26.2%), limonene (0.0-24.5%), germacrene D (4.2-19.3%), bicyclogermacrene (1.6-18.0%), δ-cadinene (6.5-16.0%), pulegone (0.0-15.1%), (Z)-hex-3-enyl tiglate (0.0-15.1%), (E)-caryophyllene (0.0-12.9), α-zingiberene (0.2-12.2%), and spathulenol (1.6-11.1%). For the determination of the chemotypes and the chemical variability, the essential-oil components were subjected to cluster analysis (CA). The five different chemotypes characterized were Chemotype I (germacrene D/bicyclogermacrene), Chemotype II (germacrene D/spathulenol), Chemotype III (limonene/δ-cadinene), Chemotype IV (pulegone), and Chemotype V (α-zingiberene). The high chemical variation among the populations according to their geographical and bioclimatic distribution imposes that conservation strategies of populations should be made appropriately, taking into account these factors. The in situ and ex situ conservation strategies should concern all populations representing the different chemotypes.

Topics: Acyclic Monoterpenes; Alkenes; Cyclohexane Monoterpenes; Cyclohexenes; Gas Chromatography-Mass Spectrometry; Iran; Limonene; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Stachys; Terpenes

Essential oils from leaves of Xylopia frutescens (XFMJ) and two specimens of Xylopia laevigata (XLMC and XLSI) were obtained by hydrodistillation using a Clevenger-type apparatus, and analyzed by GC-MS and GC-FID. Sesquiterpenes dominated the essential oils. The main constituents of XFMJ were (E)-caryophyllene (24.8%), bicyclogermacrene (20.8%), germacrene D (17.0%), beta-elemene (7.9%), and (E)-beta-ocimene (6.8%). XLMC contained significant quantities of germacrene D (18.9%), bicyclogermacrene (18.4%), beta-elemene (9.5%), delta-selinene (9.2%), (E)-caryophyllene (8.5%), germacrene B (5.7%) and gamma-muurolene (5.7%), while germacrene D (27.0%), bicyclogermacrene (12.8%), (E)-caryophyllene (8.6%), gamma-muurolene (8.6%), delta-cadinene (6.8%), and germacrene B (6.0%) were the main components of XLSI. The essential oils had trypanocidal activity against the Y strain of Trypanosoma cruzi, with IC50 values lower than 30 microg x mL(-1) and 15 microg x mL(-1) against epimastigote and trypomastigote forms of T. cruzi, respectively, and were also able to reduce the percentage in vitro of T. cruzi-infected macrophages and the intracellular number of amastigotes at concentrations that were non-cytotoxic to macrophages.

Topics: Acyclic Monoterpenes; Alkenes; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Trypanocidal Agents; Trypanosoma cruzi; Xylopia

The chemical composition of the essential oils obtained by hydrodistillation of different parts of Eremanthus erythropappus, including leaves, branches and inflorescences, was investigated by Gas Chromatography and Gas Chromatography/Mass Spectrometry. The antimicrobial activity of the oils was assessed by the disc diffusion and microdilution methods, while the antioxidant activity was evaluated by DPPH and reducing power tests. The main compounds found in the essential oils derived from the inflorescences and leaves were β-caryophyllene, germacrene-D, α-copaene and β-pinene. α-Bisabolol was the major component in the branches. The oils were active against Staphylococcus aureus, Streptococcus pyogenes and fungi, but not Escherichia coli and Pseudomonas aeruginosa. The MIC values ranged from 0.01 to 0.50 mg/mL. Using the DPPH test, the IC50 values ranged from 38.77 ± 0.76 to 102.24 ± 1.96 μg/mL, while the reducing power test produced IC50 values between 109.85 ± 1.68 and 169.53 ± 0.64 μg/mL. The results revealed that the E. erythropappus oils are new promising potential sources of antimicrobial and antioxidant compounds with good future practical applications for human health.

Topics: Anti-Infective Agents; Antioxidants; Asteraceae; Escherichia coli; Microbial Sensitivity Tests; Monocyclic Sesquiterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Pseudomonas aeruginosa; Sesquiterpenes; Sesquiterpenes, Germacrane; Staphylococcus aureus; Streptococcus pyogenes

Artemisia phaeolepis, a perennial herb with a strong volatile odor, grows on the grasslands of Mediterranean region. Essential oil obtained from Artemisia phaeolepis was analyzed by gas chromatography-flame ionization detection and gas chromatography-mass spectrometry. A total of 79 components representing 98.19% of the total oil were identified, and the main compounds in the oil were found to be eucalyptol (11.30%), camphor (8.21%), terpine-4-ol (7.32%), germacrene D (6.39), caryophyllene oxide (6.34%), and caryophyllene (5.37%). The essential oil showed definite inhibitory activity against 10 strains of test microorganisms. Eucalyptol, camphor, terpine-4-ol, caryophyllene, germacrene D and caryophyllene oxide were also examined as the major components of the oil. Camphor showed the strongest antimicrobial activity; terpine-4-ol, eucalyptol, caryophyllene and germacrene D were moderately active and caryophyllene oxide was weakly active. The study revealed that the antimicrobial properties of the essential oil can be attributed to the synergistic effects of its diverse major and minor components.

Topics: Artemisia; Aspergillus niger; Camphor; Chromatography, Gas; Cyclohexanols; Drug Resistance, Microbial; Drug Synergism; Eucalyptol; Flame Ionization; Fusarium; Gas Chromatography-Mass Spectrometry; Gram-Negative Bacteria; Gram-Positive Bacteria; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes

In this study, the chemical composition and the in vitro schistosomicidal properties of the essential oil obtained from Bidens sulphurea flowers (Bs-EO) were investigated. Its major constituents were identified as being 2,6-di-tert-butyl-4-methylphenol (44.98%), germacrene D (33.70%) and β-caryophyllene (10.23%). Bs-EO at 100 µg mL(-1) caused death of all the adult worms and promoted separation of the couple pairs into individual male and female within 48 h, besides leading to a significant decrease in the motility of the parasites. This oil was also responsible for a remarkable reduction in the number of eggs and the percentage of developed eggs produced by adult worms. These results suggest that the Bs-EO can be considered a promising source for the development of new schistosomicidal agents.

Topics: Animals; Asteraceae; Flowers; Oils, Volatile; Polycyclic Sesquiterpenes; Schistosomicides; Sesquiterpenes; Sesquiterpenes, Germacrane

The antibacterial activity of nine selected essential oils (EOs) against a panel of oral pathogens was investigated in terms of their minimum inhibitory concentrations (MICs) by using the broth microdilution method. Most of the EOs displayed weak activity or were inactive against the selected oral pathogens, with MIC values ranging from 500 to 4000 μg/mL. However, the EO obtained from the leaves of Bidens sulphurea (Asteraceae) was found to display moderate activity against Streptococcus mutans (MIC = 250 μg/mL) and significant activity against Streptococcus mitis (MIC = 31.25 μg/mL). Germacrene D (38.3%), trans-caryophyllene (18.0%), β-elemene (13.9%) and bicyclogermacrene (13.1%) were identified as the main chemical components of this oil. 2,6-Di-tert-butyl-4-methylphenol, previously described as the major constituent in the EO from the flowers of B. sulphurea, was not detected in this study.

Topics: Anti-Infective Agents; Asteraceae; Bacteria; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Streptococcus mutans

Xylopia laevigata, popularly known as "meiú" and "pindaíba", is a medicinal plant used in the folk medicine of the Brazilian Northeast for several purposes. The chemical constituents of the essential oil from leaves of X. laevigata, collected from wild plants growing at three different sites of the remaining Atlantic forest in Sergipe State (Brazilian Northeast), were analyzed by GC/FID and GC/MS. The effect of the essential oil samples was assessed on tumor cells in culture, as well on tumor growth in vivo. All samples of the essential oil were dominated by sesquiterpene constituents. A total of 44 compounds were identified and quantified. Although some small differences were observed in the chemical composition, the presence of γ-muurolene (0.60-17.99%), δ-cadinene (1.15-13.45%), germacrene B (3.22-7.31%), α-copaene (3.33-5.98%), germacrene D (9.09-60.44%), bicyclogermacrene (7.00-14.63%), and (E)-caryophyllene (5.43-7.98%) were verified as major constituents in all samples of the essential oil. In the in vitro cytotoxic study, the essential oil displayed cytotoxicity to all tumor cell lines tested, with the different samples displaying a similar profile; however, they were not hemolytic or genotoxic. In the in vivo antitumor study, tumor growth inhibition rates were 37.3-42.5%. The treatment with the essential oil did not significantly affect body weight, macroscopy of the organs, or blood leukocyte counts. In conclusion, the essential oil from the leaves of X. laevigata is chemically characterized by the presence of γ-muurolene, δ-cadinene, germacrene B, α-copaene, germacrene D, bicyclogermacrene, and (E)-caryophyllene as major constituents and possesses significant in vitro and in vivo anticancer potential.

Topics: Animals; Antineoplastic Agents, Phytogenic; Brazil; Cell Line, Tumor; Cells, Cultured; Erythrocytes; Gas Chromatography-Mass Spectrometry; Humans; Leukocytes, Mononuclear; Male; Medicine, Traditional; Mice; Oils, Volatile; Plant Leaves; Plant Oils; Plants, Medicinal; Polycyclic Sesquiterpenes; Sarcoma 180; Sesquiterpenes; Sesquiterpenes, Germacrane; Xylopia

The essential oils from aerial parts of Scutellaria laeteviolacea was analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The characteristic odor components were also detected in the oil using gas chromatography-olfactometry (GC-O) analysis and aroma extraction dilution analysis (AEDA). As a result, 100 components (accounting for 99.11 %) of S. laeteviolacea, were identified. The major components of S. laeteviolacea oil were found to be 1-octen-3-ol (27.72 %), germacrene D (21.67 %),and β-caryophyllene (9.18 %). The GC-O and AEDA results showed that 1-octen-3-ol, germacrene D, germacrene B, and β-caryophyllene were the most characteristic odor components of the oil. These compounds are thought to contribute to the unique flavor of this plant.

Topics: Chromatography, Gas; Gas Chromatography-Mass Spectrometry; Octanols; Odorants; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Scutellaria; Sesquiterpenes; Sesquiterpenes, Germacrane

The essential oils of four wild growing Origanum vulgare L. (family Lamiaceae) collected from different locations in Kumaon region (Uttarakhand, India) were analysed by capillary GC and GC/MS. The comparative results of O. vulgare L. collected from four different regions showed differences in the chemical constituents of the essential oils. The oil of O. vulgare L. collected from Dhoulchina and Champawat (chemotype I) shows p-cymene (6.7-9.8%), γ-terpinene (12.4-14.0%), thymol (29.7-35.1%) and carvacrol (12.4-20.9%) as major constituents while the oil from Kilbury and Rushi village (chemotype II) shows linalool (6.7-9.7%), bornyl acetate (12.6-16.8%), β-caryophyllene (10.5-13.8%) and germacrene D (6.3-11.3%) as the major constituents. These features highlight the chemosystematics of this genus.

Topics: Acyclic Monoterpenes; Biomarkers; Camphanes; Chromatography, Gas; Cyclohexane Monoterpenes; Cymenes; Gas Chromatography-Mass Spectrometry; Geography; India; Monoterpenes; Oils, Volatile; Origanum; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Species Specificity; Thymol

The essential oil of the Greek endemic species Marrubium thessalum Boiss. & Heldr. (Lamiaceae) was obtained by the hydrodistillation of its aerial parts during the flowering stage. The composition of the oil was analysed by GC and GC-MS. Thirty compounds were identified. The oil was devoid of monoterpenes, while sesquiterpenes constituted the major fraction. The main components of the oil were caryophyllene oxide (21.7%), β-caryophyllene (17.6%), germacrene D (15.3%), β-bisabolene (12.6%) and trans-β-farnesene (8.1%).

Topics: Chromatography, Gas; Gas Chromatography-Mass Spectrometry; Greece; Marrubium; Monocyclic Sesquiterpenes; Oils, Volatile; Plant Components, Aerial; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

The essential oil from the flowering aerial parts of Bupleurum hamiltonii Balak syn. Bupleurum tenue family Apiaceae (Umbellifereae) was obtained by steam distillation and analysed by a combination of GC (RI) and GC-MS. The chemical composition of the isolated oil is reported here for the first time. Twenty-seven compounds were identified, which represent 92.7% of the total oil. The chemical composition of the isolated oil was characterised by a high proportion of sesquiterpene hydrocarbons (61.9%), among which germacrene-D (17.8%), trans-β-farnesene (14.7%) and β-caryophyllene (13.1%) were the predominant compounds. The monoterpene hydrocarbons (16.6%) represented the second major fraction of the same oil followed by the oxygenated sesquiterpenes (7.9%).

Topics: Bupleurum; India; Oils, Volatile; Plant Components, Aerial; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

The chemical composition of essential oils obtained by hydrodistillation from the flower, leaf and stem of Falcaria vulgaris Bernh., which is endemic to Iran, were analysed by GC and GC/MS (samples were from two different localities: A from Ardabil and B from Khalkhal). α-Pinene was the major constituent in all the three oils (flower, leaf and stem) from sample A (43.8%, 33.0% and 50.9%, respectively). The oil of F. vulgaris flower was characterised by a higher amount of β-caryophyllene (25.2%) and 1,8-cineole (12.8%) among the eight components comprising 96.2% of the total oil detected. α-Terpinyl acetate (23.2%) and limonene (14.4%) predominated in the leaf oil. In the oils of sample B, α-pinene (16.1% in the flower oil, 31.5% in the leaf oil and 34.5% in the stem oil) was the major compound. Limonene (14.2%) and germacrene D (32.1%) were also the main constituents found in the leaf oil from sample B. α-Terpinyl acetate (21.9% in the leaf oil) and limonene (29.8% in stem oil) were the other major compounds obtained from this sample. Antibacterial activity was determined by the measurement of growth inhibitory zones.

Topics: Anti-Bacterial Agents; Bicyclic Monoterpenes; Chromatography, Gas; Cyclohexanols; Cyclohexenes; Eucalyptol; Gas Chromatography-Mass Spectrometry; Iran; Limonene; Microbial Sensitivity Tests; Monoterpenes; Oils, Volatile; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes

Considerable difference in artemisinin and its direct precursors, artemisinic acid and dihydroartemisinic acid, was detected between two chemotypes within the species Artemisia annua (A. annua). These two chemotypes showed differential metabolic response to methyl jasmonate (MeJA) elicitation. Exogenous application of MeJA resulted in an accumulation of dihydroartemisinic acid and artemisinin in Type I plants. In Type II plants, however, artemisinic acid and artemisinin level decreased dramatically under MeJA elicitation. Squalene and other sesquiterpenes, (e.g., caryophyllene, germacrene D), were stimulated by MeJA in both chemotypes. The effect of MeJA elicitation was also studied at the transcription level. Real time RT-PCR analysis showed a coordinated activation of most artemisinin pathway genes by MeJA in Type I plants. The lack of change in cytochrome P450 reductase (CPR) transcript in Type I plants indicates that the rate-limiting enzymes in artemisinin biosynthesis have yet to be identified. Other chemotype-specific electron donor proteins likely exist in A. annua to meet the demand for P450-mediated reactions in MeJA-mediated cellular processes. In Type II plants, mRNA expression patterns of most pathway genes were consistent with the reduced artemisinin level. Intriguingly, the mRNA transcript of aldehyde dehydrogenase1 (ADHL1), an enzyme which catalyzes the oxidation of artemisinic and dihydroartemisinic aldehydes, was upregulated by MeJA. The differential metabolic response to MeJA suggests a chemotype-dependent metabolic flux control towards artemisinin and sterol production in the species A. annua.

Topics: Acetates; Aldehyde Dehydrogenase 1 Family; Alkyl and Aryl Transferases; Artemisia annua; Artemisinins; Cyclopentanes; Cytochrome P-450 Enzyme System; Gas Chromatography-Mass Spectrometry; Gene Expression Regulation, Plant; Isoenzymes; NADPH-Ferrihemoprotein Reductase; Oxidoreductases; Oxylipins; Plant Growth Regulators; Plant Leaves; Plant Proteins; Polycyclic Sesquiterpenes; Retinal Dehydrogenase; Reverse Transcriptase Polymerase Chain Reaction; RNA, Messenger; Sesquiterpenes; Sesquiterpenes, Germacrane; Squalene; Terpenes

The essential oil from Vismia macrophylla Kunth (Guttiferae) leaves, extracted by hydrodistillation, was analyzed by GC/MS. The oil obtained (yield 0.11%) contained twenty-eight compounds, which were identified from their retention indices and by comparison of their mass spectra with those in the Wiley GC-MS Library data base. The major components were beta-caryophyllene (20.1%), germacrene D (11.6%) and beta-elemene (7.0%).

Topics: Clusiaceae; Gas Chromatography-Mass Spectrometry; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

The essential oils yield and composition of the aerial parts of A. annua var. CIM-Arogya grown in Uttarakhand, India were analyzed and compared by capillary GC and GC-MS at different stages of development. The analysis led to the identification of 81 constituents forming 91.0%-97.1% of the essential oils compositions. The essential oil content of the aerial parts was found to vary from 0.3% to 0.7% at different stages of growth. A. annua crop harvested at full flowering and seed setting stage gave higher yield of essential oil (0.6%, 0.7%) than that harvested at pre flowering (0.5%), late vegetative (0.4%, 0.5%), mid vegetative (0.4%, 0.4%) and early vegetative stages (0.3%, 0.3%). The essential oils at different stages of growth showed monoterpenoids (38.5%-72.0%) and sesquiterpenoids (22.2%-48.2%) as major grouped constituents. The major constituents identified were camphor (22.8%-42.6%), 1,8-cineole (3.7%-8.4%), linalool (<0.1%-11.9%), beta-caryophyllene (2.0%-9.2%), (E)-beta-farnesene (1.3%-8.5%), germacrene D (0.5%-7.3%) and 1-epi-cubenol (0.7%-5.2%) in essential oil samples collected at different crop stages.

Topics: Acyclic Monoterpenes; Artemisia annua; Camphor; Cyclohexanols; Eucalyptol; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

The chemical compositions of the essential oils obtained by hydrodistillation from the aerial parts of Scutellaria diffusa, Scutellaria heterophylla and Scutellaria salviifolia were separately identified simultaneously by gas chromatography and gas chromatography-mass spectrometry. The main components were determined as hexadecanoic acid (30%) and caryophyllene oxide (9%) in the oil of S. diffusa. Germacrene D (21%), hexadecanoic acid (16%) and β-caryophyllene (13%) were found as major components in the oil of S. heterophylla. The main components of the oil of S. salviifolia were germacrene D (40%), bicyclogermacrene (14%) and β-caryophyllene (11%). Overall, individually 63, 68 and 43 constituents were identified in the aerial parts of S. diffusa, S. heterophylla and S. salviifolia essential oils representing 92.1%, 89.9% and 90% of the total, respectively.

Topics: Chromatography, Gas; Gas Chromatography-Mass Spectrometry; Oils, Volatile; Palmitic Acid; Polycyclic Sesquiterpenes; Scutellaria; Sesquiterpenes; Sesquiterpenes, Germacrane; Species Specificity; Turkey

Chemical composition, antioxidant and antimicrobial activities of the fresh leaves and stems oils of Piper caninum were investigated. A total of forty eight constituents were identified in the leaves (77.9%) and stems (87.0%) oil which were characterized by high proportions of phenylpropanoid, safrole with 17.1% for leaves and 25.5% for stems oil. Antioxidant activities were evaluated by using β-carotene/linoleic acid bleaching, DPPH radical scavenging and total phenolic content. Stems oil showed the highest inhibitory activity towards lipid peroxidation (114.9 ± 0.9%), compared to BHT (95.5 ± 0.5%), while leaves oil showed significant total phenolic content (27.4 ± 0.5 mg GA/g) equivalent to gallic acid. However, the essential oils showed weak activity towards DPPH free-radical scavenging. Evaluation of antimicrobial activity revealed that both oils exhibited strong activity against all bacteria strains with MIC values in the range 62.5 to 250 μg/mL, but weak activity against fungal strains. These findings suggest that the essential oils can be used as antioxidant and antimicrobial agents for therapeutic, nutraceutical industries and food manufactures.

Topics: Anti-Infective Agents; Antioxidants; beta Carotene; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Gas Chromatography-Mass Spectrometry; Linoleic Acid; Lipid Peroxidation; Microbial Sensitivity Tests; Monoterpenes; Oils, Volatile; Phenols; Piper; Plant Extracts; Plant Leaves; Plant Stems; Polycyclic Sesquiterpenes; Safrole; Sesquiterpenes; Sesquiterpenes, Germacrane

Senecio rufinervis D.C (Asteraceae) is a tall aromatic herb, commonly found in Uttarakhand, India. No investigations on the biological activity of this plant have been published so far. Hence, this plant species became a subject of our scientific interest.. The aim of the study was to investigate the chemical composition and analgesic activity of Senecio rufinervis essential oil in mice using both thermal and chemical models of pain.. Essential oil from dried leaves of Senecio rufinervis was extracted by steam distillation and then subjected to GC-MS analysis. Varying doses of essential oil were given to mice, 30 min prior to the induction of abdominal constrictions and determination of mean reaction time in hot-plate maintained at 55° ± 0.5°C.. The main component detected in the essential oil of Senecio rufinervis was germacrene D (40.19%) followed by β-pinene (12.23%), β-caryophyllene (6.21%) and β-longipinene (4.15%). Essential oil exhibited significant and dose-dependent analgesic activity against acetic acid-induced writhing in mice. The percentage inhibition in number of writhes produced by 25, 50 and 75 mg/kg doses was, respectively, 69, 80 and 85%. The oil, at doses 50 and 75 mg/kg, significantly increased the mean latency in the hot-plate after 15 and 30 min of drug administration as compared to the control group.. The results depicted both central and peripheral analgesic activity of S. rufinervis essential oil which was attributed to the presence of terpenes.

Topics: Abdominal Pain; Analgesics; Animals; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Dose-Response Relationship, Drug; Gas Chromatography-Mass Spectrometry; Hot Temperature; Hyperalgesia; India; Male; Mice; Mice, Inbred Strains; Monoterpenes; Oils, Volatile; Pain; Pain Measurement; Phytotherapy; Plant Leaves; Plant Oils; Polycyclic Sesquiterpenes; Rotarod Performance Test; Senecio; Sesquiterpenes; Sesquiterpenes, Germacrane

The essential oils obtained by simultaneous distillation and extraction (SDE) from the fresh and dried needles and dried berries of Juniperus communis L. of Estonian origin were subjected to GC-FID and GC-MS analyses. The yields of the oils ranged between 0.2% and 0.6% from juniper berries and between 0.5% and 1.0% from needles (dried weight). A total of 87 compounds were identified, representing over 95% of the oil. The major compounds in the needle oil were monoterpenes α-pinene (33.3-45.6%), sabinene (0.2-15.4%), limonene (2.8-4.6%) and sesquiterpenes (E)-β-caryophyllene (0.8-10.3%), α-humulene (0.8-6.2%) and germacrene D (3.0-7.8%). The juniper berry oil was rich in α-pinene (53.6-62.3%), β-myrcene (6.5-6.9%) and germacrene D (4.5-6.1%). The main oxygenated terpenoids found in the needle oil were germacrene D-4-ol (0.4-4.0%) and α-cadinol (to 2.7%). The oil from fresh needles contained high amounts of (E)-2-hexenal (3.7-11.7%).

Topics: Bicyclic Monoterpenes; Cyclohexenes; Estonia; Fruit; Juniperus; Limonene; Monoterpenes; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes

The volatile constituents in the flowers of Aglaia odorata were extracted by supercritical CO2 fluid under 25 MPa and 40 degrees C for 80 min. The oil yield was 2.64%. These volatile constituents were separated and identified by capillary gas chromatography-mass spectrometry (GC-MS). Experiments were performed on an Agilent 6890 GC Chromatograph with Agilent 5973N Mass Selective Detector. The GC separation conditions was carried out on an HP-5MS capillary column (60 m x 250 microm, 0.25 microm); oven temperature, 50 degrees C (held for 2 min) to 280 degrees C at a rate of 5 degrees C/min, and held for 8 min; split ratio, 1 : 10; injector temperature, 270 degrees C. Mass spectra were collected in the scan range of m/z 50 - 550. The measurements were performed with electron bombardment ion (EI) source with electron energy of 70 eV and electron multiplier voltage of 1.65 kV. The results showed that 54 peaks were separated and 48 compounds were identified for the essential oil extracted from Aglaia odorata L. There were 18 terpenes, 12 esters and other constituents in the volatile oil fraction. The constituents in the oil fraction were alpha-humulene, followed by ethyl linolenate, germacrene D, beta-elemene, copaene, caryophyllene, methyl jasmonate, beta-humulene-7-ol, ethyl palmitate, etc.

Topics: Acetates; Aglaia; Cyclopentanes; Flowers; Gas Chromatography-Mass Spectrometry; Linolenic Acids; Monocyclic Sesquiterpenes; Oils, Volatile; Oxylipins; Palmitic Acids; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Temperature

The composition of the spasmolytic essential oil of the medicinal species Brickellia veronicaefolia was established by NMR spectroscopy in addition to GC-MS analysis and HPLC studies. Seven major compounds, representing ca. 86% of the oil, were identified as benzyl 2,6-dimethoxybenzoate (1), 2-hydroxybenzyl 2'-methoxybenzoate (2), chamazulene (3), beta-caryophyllene (4), germacrene D (5), bicyclogermacrene (6), and beta-eudesmol (7). A sensitive and accurate analytical 1H NMR method has been developed for the quantification of the major compounds in the essential oil of B. veronicaefolia. The method was validated using benzyl 2,6-dimethoxybenzoate (1) and beta-caryophyllene (4), two of the active principles in the oil, and successfully applied to the determination of these pharmacologically active compounds in three different batches of the oil collected in different geographical regions and/or seasons.

Topics: Asteraceae; Hydroxybenzoate Ethers; Hydroxybenzoates; Magnetic Resonance Spectroscopy; Mexico; Molecular Structure; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Eudesmane; Sesquiterpenes, Germacrane

The aim of this work was to analyze the essential oil content and its composition in the drug (Serpylli herba) of wild thyme (Thymus serpyllum L.) originating from 20 different natural places of growth in Estonia.. The quantitative content of essential oil was determined according to the method of European Pharmacopoeia. Gas chromatographic analysis of essential oils was carried out using a gas chromatography with flame ionization detector on two fused silica capillary columns with bonded stationary phases NB-30 and SW-10. The identification of the oil components was accomplished by comparing their retention indices on two columns with the retention indices values of standard compounds, with our retention indices data bank and with literature data. The results obtained were confirmed by gas chromatography / mass spectrometry.. The content of essential oil is between 0.6 and 4 ml/kg and usually is not in conformity with European Pharmacopoeia standard (3 ml/kg). There were 55 components identified in the essential oil of wild thyme of Estonian origin. Differently from the data in the literature of foreign countries, thymol and carvacrol are not the main components of the essential oil of wild thyme growing in Estonia. The main components here are (E)-nerolidol, caryophyllene oxide, myrcene, (E)-beta-caryophyllene and germacrene D.. In Estonia, the (E)-nerolidol-caryophyllene oxide, (E)-nerolidol-myrcene and myrcene chemotypes of wild thyme drug are distinguishable.

Topics: Anti-Inflammatory Agents, Non-Steroidal; Chromatography, Gas; Estonia; Humans; Mass Spectrometry; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Thymus Plant

Fresh aerial parts of Angelica glauca, growing wild in Kashmir valley in higher Himalaya (Jammu and Kashmir, India), collected at flowering stage from different locations, on hydro-distillation provided a refreshing light pale coloured essential oil with characteristic floral woody flavour. The oil was found to be a complex mixture of mono- and sesquiterpenes and 34 compounds accounting for nearly 97.4% of the oil were characterized with the help of capillary GC, GC-MS, and NMR. Major compounds of the oil were characterized as alpha-phellandrene (13.5%), trans-carveol (12.0%), beta-pinene (11.7%), thujene (7.5%), beta-caryophyllene oxide (7.2%), beta-caryophyllene (7.0%), gamma-terpinene (6.7%), nerolidol (6.5%), beta-bisabolene (5.2%) and germacrene D (4.5%). It is the first report to exploit the essential oil from Himalayan A. glauca herb collected at flowering stage.

Topics: Angelica; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexane Monoterpenes; India; Monoterpenes; Oils, Volatile; Plant Components, Aerial; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

Plants release complex mixtures of volatiles, including chiral constituents. In the search for the biologically relevant plant odorants, gas chromatography linked to electrophysiological recordings from single receptor neurons has been employed. In heliothine moths, including the females of the Eurasian cotton bollworm moth Helicoverpa armigera, a major type of receptor neurons is identified, showing high sensitivity and selectivity for the sesquiterpene germacrene D. In the present study, gas chromatography with a chiral column linked to single cell recordings were performed. It was found that all germacrene D neurons belonged to one type; all responded to both enantiomers, but (-)-germacrene D had approximately 10 times stronger effect than (+)-germacrene D. Parallel dose-response curves for the two enantiomers were obtained by direct stimulations. The enantiomeric composition of germacrene D, which differed in six plant species and in different individuals of one species, was determined on the basis of the neuron responses. The results, showing the presence of one neuron type for receiving the information about germacrene D in the various plants, suggests that the two enantiomers mediate the same kind of information to the moth, but with different intensity.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Chromatography, Gas; Dose-Response Relationship, Drug; Female; Models, Chemical; Moths; Neurons; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Species Specificity; Time Factors

Twenty-one volatile compounds were identified for the first time by GC-MS in umbu-caja and in camu-camu, plus 30 volatile compounds were identified in araça-boi samples. Terpenic compounds predominated among the volatile compounds in these fruit samples, with the major compounds being identified as cis-beta-ocimene and caryophyllene in the northeastern fruit; alpha-pinene and d-limonene were the most abundant volatile compounds in the headspace of the Amazonian fruit camu-camu. Sesquiterpenes were the most abundant compounds in the araça-boi sample, with germacrene D presenting a higher relative percentage. The chemical class of esters predominated in the cupuaçu sample. Ethyl butyrate and hexanoate were the major compounds in the headspace of this Amazonian fruit.

Topics: Bicyclic Monoterpenes; Brazil; Cyclohexenes; Fruit; Gas Chromatography-Mass Spectrometry; Limonene; Monoterpenes; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes

The essential oils of Torilis japonica (Houtt.) DC. (Japanese name, Yabujirami) of the family Umbelliferae were prepared from fresh whole herbs and fruits, and investigated by using gas chromatographic and mass spectrometric analyses. The fruits of this plant had been used as a substitute in Japan for a Chinese crude drug Zya-syo-si: Cnidii Monnieri Fructus. Fifty three components were positively identified in the essential oils. The main components of the essential oil were germacrene-D (57.9-71.8% in the oil), alpha-humulene (2.4-13.2%), bicyclogermacrene (1.9-5.4%), beta-caryophyllene (1.5-4.6%), and delta-cadinene (1.0-1.9%).

Topics: Monocyclic Sesquiterpenes; Oils, Volatile; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane