caryophyllene and sabinene

The present study reports the chemical composition and antioxidant activities of the essential oil extracted from the leaves and tender branches of Hypericum gaitii Haines (Hypericaceae) - an endemic plant of Eastern India. On hydrodistillation, the fresh leaves and tender parts of H. gaitii yielded 0.43% (v/w) of pale yellowish essential oil. Gas chromatography mass spectrometry analysis revealed the presence of 40 compounds, which represent 96.9% of the total oil. Monoterpene hydrocarbons (79.3%) predominated followed by sesquiterpene hydrocarbons (12.6%). Of these, α-pinene (69.5%), β-caryophyllene (10.5%), sabinene (5.6%), myrcene (3.0%) and geranyl acetate (2.0%) were the main constituents. Antioxidant activities of oil were evaluated by three different systems namely 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) and reducing power assay. Essential oil exhibited moderate antioxidant activities compared to butylated hydroxytoluene (BHT) and ascorbic acid.

Topics: Acetates; Acyclic Monoterpenes; Antioxidants; Bicyclic Monoterpenes; Butylated Hydroxytoluene; Gas Chromatography-Mass Spectrometry; Hypericum; India; Monoterpenes; Oils, Volatile; Plant Extracts; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes

A detailed phytochemical analysis of Origanum vulgare L. ssp. viride (Boiss.) Hayek was carried out and the antioxidant activities of five different crude extracts were determined. The antiproliferative activities of the extracts were determined using the xCELLigence system (Real Time Cell Analyzer).. Differences between the essential oil and volatile organic compound profiles of the plant were shown. The main component of the essential oil was caryophyllene oxide, while the main volatile organic compounds were sabinene and eucalyptol as determined by HS-GC/MS. Phenolic contents of the extracts were determined qualitatively and quantitatively by HPLC/TOF-MS. Ten phenolic compounds were found in the extracts from O. vulgare and Origanum acutidens: rosmarinic acid (in highest abundance), chicoric acid, caffeic acid, p-coumaric acid, gallic acid, quercetin, apigenin-7-glucoside, kaempferol, naringenin and 4-hydroxybenzaldehyde.. This study provides first results on the antiproliferative and antioxidant properties and detailed phytochemical screening of O. vulgare ssp. viride (Boiss.) Hayek.

Topics: Antineoplastic Agents, Phytogenic; Antioxidants; Bicyclic Monoterpenes; Cell Proliferation; Cyclohexanols; Drug Discovery; Ethnopharmacology; Eucalyptol; Flowers; HeLa Cells; Humans; Medicine, Traditional; Molecular Structure; Monoterpenes; Oils, Volatile; Origanum; Phenols; Plant Components, Aerial; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes; Turkey; Volatile Organic Compounds

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

This article reports the chemical components identified in the essential oil from the leaf and stem barks of Polyalthia harmandii (Pierre) Fin. and Gagnep., Polyalthia jucunda (Pierre) Fin. and Gagnep. and Polyalthia thorelii (Pierre) Fin. and Gagnep. The compounds identified in all the samples were α-pinene (0.2-3.2%), myrcene (0.3-4.1%), (E)-β-ocimene (0.2-9.6%), bicycloelemene (0.2-18.0%), β-elemene (0.3-4.9%), β-caryophyllene (0.1-17.8%), germacrene D (4.4-20.1%), bicyclogermacrene (4.2-27.9%) and δ-cadinene (0.2-4.5%). Besides, benzyl benzoate (9.7%) and ishwarane (8.0%), respectively, were the other prominent compounds in the leaf and stem of P. harmandii. In addition, δ-3-carene (8.2%), α-amorphene (6.5%), β-phellandrene (5.5%) and β-pinene (5.1%) were identified in P. jucunda leaf, while sabinene (30.9%) and β-phellandrene (10.2%) occurred largely in the stem. Moreover, γ-elemene (22.3% and 12.3%), germacrene D (10.5% and 6.9%) and spathulenol (9.1% and 11.8%) were identified in the leaf and stem of P. thorelii, while α-terpinene (7.8%) and β-gurjunene (5.2%) were identified only in the leaf oil.

Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexane Monoterpenes; Cyclohexenes; Cyclopropanes; Monoterpenes; Oils, Volatile; Plant Leaves; Plant Stems; Polyalthia; Polycyclic Sesquiterpenes; Sesquiterpenes; Vietnam

This article reports the compounds identified in the leaf oils of five Clauseana species growing in Vietnam. The hydrodistilled oils were analysed for their chemical constituents by using gas chromatography-flame ionisation detector and gas chromatography coupled with mass spectrometry. The major compounds identified in Clausena dentata (Willd.) M. Roem. were α-pinene (21.7%), sabinene (18.3%) and β-myrcene (14.3%). Clausena dimidiata Tanaka comprised mainly of safrole (56.9%) and α-terpinolene (22.1%). However, 1-menthone (70.6%) and β-phellandrene (13.0%) were the most abundant compounds of Clausena indica (Dalz.) Oliver. Sesquiterpene compounds represented mainly by β-caryophyllene (16.7%), spathulenol (11.9%) and bicyclogermacrene (7.5%) were the major constituents of Clausena excavata Burm. f., while those of Clausena engleri Tanaka include bicycloelemene (12.1%), bicyclogermacrene (11.0%) and (E)-nerolidol (6.6%). This is the first report on the chemical analysis of essential oils of C. dimidiata and C. engleri.

Topics: Acyclic Monoterpenes; Bicyclic Monoterpenes; Chromatography, Gas; Clausena; Cyclohexane Monoterpenes; Cyclohexenes; Monoterpenes; Plant Leaves; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Vietnam

Dormant buds are recognized as valuable side product of the blackcurrant cultivation. Four blackcurrant varieties cultivated in Serbia, i.e., Ben Sarek, Ometa, Ben Lomond, and Ben Nevis, were evaluated for the content, chemical composition, and antimicrobial activity of their bud essential oils. The oil yields of buds harvested during two different growth periods ranged from 1.2-2.0%, and the variety Ometa had the highest yield among the tested varieties. GC-FID and GC/MS analysis of the oils allowed the identification of eight main components, i.e., α-pinene (1.6-5.4%), sabinene (1.9-38.4%), δ-car-3-ene (13.0-50.7%), β-phellandrene (2.9-18.0%), terpinolene (6.6-11.9%), terpinen-4-ol (0.9-6.6%), β-caryophyllene (3.8-10.4%), and α-humulene (0.2-4.1%). In addition, the similarity degree of the essential-oil compositions of buds harvested from the upper and lower parts of the shrubs was investigated by hierarchical clustering. All essential oils originating from the same genotype were grouped in the same cluster, indicating the reliability of essential oils as chemotaxonomic markers. For more detailed chemotaxonomic investigations, the three compounds with the greatest variance were chosen, i.e., sabinene, δ-car-3-ene, and β-phellandrene, which proved to be efficient for the variety distinction. Factor analysis showed that the essential-oil composition as chemotaxonomic marker in blackcurrants was more reliable for variety Ben Sarek than for variety Ben Nevis. Moreover, it was demonstrated that the essential oils had very strong inhibitory activity against all tested microorganisms. Fungi were more sensitive than bacteria; indeed their growth was completely inhibited at much lower concentrations. In comparison to commercial antibiotics, significantly lower concentrations of the oils were necessary for the complete inhibition of fungal growth.

Topics: Anti-Infective Agents; Bicyclic Monoterpenes; Biomarkers; Cyclohexane Monoterpenes; Cyclohexenes; Drug Resistance, Bacterial; Gas Chromatography-Mass Spectrometry; Microbial Sensitivity Tests; Molecular Typing; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Principal Component Analysis; Ribes; Serbia; Sesquiterpenes; Terpenes

The secondary organic aerosol (SOA) mass yields from NO3 oxidation of a series of biogenic volatile organic compounds (BVOCs), consisting of five monoterpenes and one sesquiterpene (α-pinene, β-pinene, Δ-3-carene, limonene, sabinene, and β-caryophyllene), were investigated in a series of continuous flow experiments in a 10 m(3) indoor Teflon chamber. By making in situ measurements of the nitrate radical and employing a kinetics box model, we generate time-dependent yield curves as a function of reacted BVOC. SOA yields varied dramatically among the different BVOCs, from zero for α-pinene to 38-65% for Δ-3-carene and 86% for β-caryophyllene at mass loading of 10 μg m(-3), suggesting that model mechanisms that treat all NO3 + monoterpene reactions equally will lead to errors in predicted SOA depending on each location's mix of BVOC emissions. In most cases, organonitrate is a dominant component of the aerosol produced, but in the case of α-pinene, little organonitrate and no aerosol is formed.

Topics: Aerosols; Air Pollutants; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexenes; Kinetics; Limonene; Monoterpenes; Nitrates; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Volatile Organic Compounds

Melittis melissophyllum (Lamiaceae) is a perennial herb, typical of woody places, occurring in Italy with two subspecies, i.e., melissophyllum and albida. So far, the classification of these two taxa was only based on morphology, i.e., the presence of glandular trichomes, the dimension of the leaves, and the number of teeth on each side as the main discriminant characters. To find marker compounds to chemically discriminate the subsp. melissophyllum with respect to the subsp. albida, a solid-phase microextraction SPME analysis coupled with GC/FID (=flame ionization detector) and GC/MS was carried out. SPME proved to be a chemotaxonomically useful technique that permitted a clearly differentiation of the two subspecies at headspace level. The subsp. melissophyllum was characterized by high amount of the mushroom alcohol oct-1-en-3-ol and the phenolic coumarin, whilst the subsp. albida exhibited a high content in monoterpenes and sesquiterpenes, α-pinene, sabinene, and (E)-caryophyllene being the major compounds. Multivariate chemometric techniques, such as cluster analysis (CA) and principal-component analysis (PCA), were used to support chemical data and characterize the population according to the taxonomy. In addition, the micromorphology and distribution of glandular trichomes of both subspecies were studied by scanning electron microscopy (SEM).

Topics: Bicyclic Monoterpenes; Complex Mixtures; Coumarins; Gas Chromatography-Mass Spectrometry; Italy; Lamiaceae; Monoterpenes; Octanols; Oils, Volatile; Phylogeography; Plant Leaves; Polycyclic Sesquiterpenes; Principal Component Analysis; Sesquiterpenes; Solid Phase Microextraction

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