caryophyllene and alpha-pinene

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

Terpenes possess a wide range of medicinal properties and are potential therapeutics for a variety of pathological conditions. This study investigated the acute effects of two cannabis terpenes, β-caryophyllene and α-pinene, on zebrafish locomotion, anxiety-like, and boldness behaviour using the open field exploration and novel object approach tests. β-caryophyllene was administered in 0.02%, 0.2%, 2.0%, and 4% doses. α-pinene was administered in 0.01%, 0.02%, and 0.1% doses. As α-pinene is a racemic compound, we also tested its (+) and (-) enantiomers to observe any differential effects. β-caryophyllene had only a sedative effect at the highest dose tested. α-pinene had differing dose-dependent effects on anxiety-like and motor variables. Specifically, (+)-α-pinene and (-)-α-pinene had significant effects on anxiety measures, time spent in the thigmotaxis (outer) or center zone, in the open field test, as well as locomotor variables, swimming velocity and immobility. (+ /-)-α-pinene showed only a small effect on the open field test on immobility at the 0.1% dose. This study demonstrates that α-pinene can have a sedative or anxiolytic effect in zebrafish and may have different medicinal properties when isolated into its (+) or (-) enantiomers.

Topics: Animals; Anti-Anxiety Agents; Bicyclic Monoterpenes; Biomarkers; Cannabis; Hallucinogens; Hypnotics and Sedatives; Polycyclic Sesquiterpenes; Terpenes; Zebrafish

Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Glycyrrhiza; Iran; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes

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

The chemical constituents identified in the essential oils hydrodistilled from the leaves of Amomum gagnepainii T.L.Wu, K.Larsen and Turland and Amomum repoense Pierre ex Gagnep (Zingiberaceae) of Vietnam origin are reported. The chemical analyses were performed by means of gas chromatography-flame ionisation detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC-MS). The main compounds of A. gagnepainii were farnesyl acetate (18.5%), zerumbone (16.4%) and β-caryophyllene (10.5%). On the other hand, Amomum repoense comprised of monoterpenes dominated by β-pinene (33.5%), (E)-β-ocimene (9.6%), γ-terpinene (9.1%) and α-pinene (8.4%). This is the first report on the essential oils of A. gagnepainii and A. repoense grown in Vietnam or elsewhere.

Topics: Acyclic Monoterpenes; Alkenes; Amomum; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexane Monoterpenes; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Plant Leaves; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Vietnam; Zingiberaceae

The essential oils (EOs) extracted from Evodia lenticellata Huang and Evodia rutaecarpa (Juss.) Benth. leaves are screened to evaluate their contact toxicity and repellency towards Tribolium castaneum (Coleoptera: Tenebrionidae), Lasioderma serricorne (Coleoptera: Anobiidae) and Liposcelis bostrychophila (Psocoptera: Liposcelididae) adults. The EOs are obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC-MS). The principal components in the E. lenticellata EO are identified to be caryophyllene oxide (28.5%), β-caryophyllene (23.1%), β-elemene (14.5%), and β-cubebene (4.7%), while the main components of the E. rutaecarpa EO are α-pinene (39.4%), β-elemene (13.5%), α-ocimene (7.6%), and α-selinene (4.0%). These two kinds of EOs and their individual compounds all showed different levels of contact toxicity and repellent activity against three stored-product insects.

Topics: Acyclic Monoterpenes; Alkenes; Animals; Bicyclic Monoterpenes; Coleoptera; Distillation; Evodia; Gas Chromatography-Mass Spectrometry; Insect Repellents; Monoterpenes; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Tribolium

Cannabis (Cannabis sativa) plants produce and accumulate a terpene-rich resin in glandular trichomes, which are abundant on the surface of the female inflorescence. Bouquets of different monoterpenes and sesquiterpenes are important components of cannabis resin as they define some of the unique organoleptic properties and may also influence medicinal qualities of different cannabis strains and varieties. Transcriptome analysis of trichomes of the cannabis hemp variety 'Finola' revealed sequences of all stages of terpene biosynthesis. Nine cannabis terpene synthases (CsTPS) were identified in subfamilies TPS-a and TPS-b. Functional characterization identified mono- and sesqui-TPS, whose products collectively comprise most of the terpenes of 'Finola' resin, including major compounds such as β-myrcene, (E)-β-ocimene, (-)-limonene, (+)-α-pinene, β-caryophyllene, and α-humulene. Transcripts associated with terpene biosynthesis are highly expressed in trichomes compared to non-resin producing tissues. Knowledge of the CsTPS gene family may offer opportunities for selection and improvement of terpene profiles of interest in different cannabis strains and varieties.

Topics: Acyclic Monoterpenes; Alkenes; Alkyl and Aryl Transferases; Bicyclic Monoterpenes; Cannabis; Cyclohexenes; Gene Expression Regulation, Plant; Inflorescence; Isoenzymes; Limonene; Metabolic Networks and Pathways; Monocyclic Sesquiterpenes; Monoterpenes; Multigene Family; Phylogeny; Polycyclic Sesquiterpenes; RNA, Messenger; Sesquiterpenes; Terpenes

Rhus coriaria, also known as Sumac, has been traditionally used in many countries as spice, condiment, dying agent, and medicinal herb. The chemical composition of essential oils (EOs) and the volatile emissions from different organs of this species collected in Sicily (Italy) were analyzed by gas chromatography-flame ionization detection and gas chromatography/mass spectrometry. Monoterpene and sesquiterpene hydrocarbons were the most abundant class in the volatile emissions with β-caryophyllene and α-pinene were the main constituents in the majority of the examined samples. The EO composition was characterized by high amount of monoterpene and sesquiterpene hydrocarbons together with diterpenes. The main compounds in the EO obtained from the leaves and both stages of fruit maturation were cembrene and β-caryophyllene, while α-pinene and tridecanoic acid were the key compounds in the flower EO. All the data were submitted to multivariate statistical analysis showing many differences among the different plant parts and their ontogenetic stages.

Topics: Bicyclic Monoterpenes; Cluster Analysis; Fruit; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Plant Leaves; Plant Roots; Plant Stems; Polycyclic Sesquiterpenes; Principal Component Analysis; Rhus; Sesquiterpenes; Solid Phase Microextraction; Volatile Organic Compounds

Melicope belahe (Baill.) T.G. Hartley (Rutaceae) is an endemic species to Madagascar. The chemical composition of leaf essential oil is reported for the first time. A sample was extracted by hydrodistillation and analysis was carried out by combination of chromatographic (GC), spectroscopic and spectrometric (MS,

Topics: Acyclic Monoterpenes; Bicyclic Monoterpenes; Madagascar; Magnetic Resonance Spectroscopy; Monoterpenes; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Rutaceae; Sesquiterpenes

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

The chemical composition of the essential oils isolated from the aerial parts of Anthemis arvensis L. subsp. arvensis, Anthemis cretica subsp. messanensis (Brullo) Giardina & Raimondo and from flowers and leaves of Anthemis cretica subsp. columnae (Ten.) Frezén were determinated by GC-FID and GC-MS analyses. Torreyol (85.4%) was recognised as the main constituent of the Anthemis arvensis subsp. arvensis essential oil, while in the essential oils of Anthemis cretica subsp. messanensis, collected on the rock and cultivated in Hortus Botanicus Panormitanus, (E)-chrysanthenyl acetate (28.8 and 24.2% resp.), 14-hydroxy-α-humulene (8.1 and 5.3% resp.), santolina triene (8 and 5.8% resp.) and α-pinene (6.7 and 5.4% resp.) prevailed. 18-cineole (13.3 and 12.2% resp.), was the main component of both flower and leaf oils of Anthemis cretica subsp. columnae together with δ-cadinene (9.0 and 8.2% resp.) and (E)-caryophyllene (8.3 and 5.6% resp.).

Topics: Anthemis; Anti-Infective Agents; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexanols; Drug Evaluation, Preclinical; Eucalyptol; Flowers; Gas Chromatography-Mass Spectrometry; Microbial Sensitivity Tests; Monoterpenes; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Sicily

Lophostemon suaveolens is a relatively unexplored endemic medicinal plant of Australia. Extracts of fresh leaves of L. suaveolens obtained from sequential extraction with n-hexane and dichloromethane exhibited antibacterial activity in the disc diffusion and MTT microdilution assays against Streptococcus pyogenes and methicillin sensitive and resistant strains of Staphylococcus aureus (minimum bactericidal concentration < 63 μg/mL). The dichloromethane extract and chromatographic fractions therein inhibited nitric oxide in RAW264.7 murine macrophages (IC50 3.7-11.6 μg/mL) and also PGE2 in 3T3 murine fibroblasts (IC50 2.8-19.7 μg/mL). The crude n-hexane, dichloromethane and water extracts of the leaves and chromatographic fractions from the dichloromethane extract also showed modest antioxidant activity in the ORAC assay. GC-MS analysis of the n-hexane fraction showed the presence of the antibacterial compounds aromadendrene, spathulenol, β-caryophyllene, α-humulene and α-pinene and the anti-inflammatory compounds β-caryophyllene and spathulenol. Fractionation of the dichloromethane extract led to the isolation of eucalyptin and the known anti-inflammatory compound betulinic acid.

Topics: 3T3 Cells; Animals; Anti-Bacterial Agents; Anti-Inflammatory Agents; Australia; Azulenes; Betulinic Acid; Bicyclic Monoterpenes; Flavonoids; Mice; Microbial Sensitivity Tests; Monocyclic Sesquiterpenes; Monoterpenes; Myrtaceae; Nitric Oxide; Pentacyclic Triterpenes; Plant Extracts; Plant Leaves; Plants, Medicinal; Polycyclic Sesquiterpenes; RAW 264.7 Cells; Sesquiterpenes; Staphylococcus aureus; Streptococcus pyogenes; Triterpenes; Tumor Necrosis Factor-alpha

Ferula communis is a showy herbaceous plant typical of the Mediterranean area where it is used as a traditional medicine. The plant is a source of bioactive compounds such as daucane sesquiterpenes and prenylated coumarins. In Italy, most of phytochemical studies focused on Sardinian populations where poisonous and nonpoisonous chemotypes were found, while investigations on peninsular populations are scarce. In this work, we report the chemical characterisation of the essential oils obtained from different parts of F. communis growing in central Italy. The chemical profiles of the plant parts, as detected by GC-FID and GC-MS, were different from each other and from those reported in insular populations. Notably, α-pinene (10.5%), γ-terpinene (7.6%) and hedycariol (8.4%) were the major volatile constituents in flowers; α-pinene (55.9%), β-pinene (16.8%) and myrcene (5.9%) in fruits; β-eudesmol (12.1%), α-eudesmol (12.1%) and hedycariol (10.3%) in leaves; (E)-β-farnesene (9.5%), β-cubebene (8.2%) and (E)-caryophyllene (7.2%) in roots. The volatile profiles detected did not allow to classify the investigated central Italy population into the poisonous and nonpoisonous chemotypes previously described in Sardinia.

Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Coumarins; Cyclohexane Monoterpenes; Ferula; Flowers; Fruit; Gas Chromatography-Mass Spectrometry; Italy; Monoterpenes; Oils, Volatile; Plant Leaves; Plant Roots; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Eudesmane

Mosquito-borne diseases represent a deadly threat for millions of people worldwide. Eco-friendly mosquitocides are a priority. In Ayurvedic medicine, Plectranthus species have been used to treat heart disease, convulsions, spasmodic pain and painful urination. In this research, we evaluated the acute toxicity of essential oil from Plectranthus barbatus and its major constituents, against larvae of the malaria vector Anopheles subpictus, the dengue vector Aedes albopictus and the Japanese encephalitis vector Culex tritaeniorhynchus. The chemical composition of P. barbatus essential oil was analyzed by gas chromatography-mass spectroscopy. Nineteen components were identified. Major constituents were eugenol (31.12%), α-pinene (19.38%) and β-caryophyllene (18.42%). Acute toxicity against early third-instar larvae of An. subpictus, Ae. albopictus and Cx. tritaeniorhynchus was investigated. The essential oil had a significant toxic effect against larvae of An. subpictus, Ae. albopictus and Cx. tritaeniorhynchus, with 50% lethal concentration (LC50) values of 84.20, 87.25 and 94.34 μg/ml and 90% lethal concentration (LC90) values of 165.25, 170.56 and 179.58 μg/ml, respectively. Concerning major constituents, eugenol, α-pinene and β-caryophyllene appeared to be most effective against An. subpictus (LC50 = 25.45, 32.09 and 41.66 μg/ml, respectively), followed by Ae. albopictus (LC50 = 28.14, 34.09 and 44.77 μg/ml, respectively) and Cx. tritaeniorhynchus (LC50 = 30.80, 36.75 and 48.17 μg/ml, respectively). Overall, the chance to use metabolites from P. barbatus essential oil against mosquito vectors seems promising, since they are effective at low doses and could be an advantageous alternative to build newer and safer mosquito control tools.

Topics: Aedes; Animals; Anopheles; Bicyclic Monoterpenes; Culex; Dengue; Encephalitis, Japanese; Eugenol; Gas Chromatography-Mass Spectrometry; India; Insect Vectors; Insecticides; Larva; Lethal Dose 50; Malaria; Monoterpenes; Mosquito Control; Oils, Volatile; Plant Extracts; Plectranthus; Polycyclic Sesquiterpenes; Sesquiterpenes; Specific Pathogen-Free Organisms

The compositions of the essential oils obtained from leaves and stems of Gynura bicolor DC. were analyzed by GC-MS. One hundred eight components of these oils were identified. (E)-β-caryophyllene (31.42 %), α-pinene (17.11 %), and bicyclogermacrene (8.09 %) were found to be the main components of the leaf oil, while α-pinene (61.42 %), β-pinene (14.39 %), and myrcene (5.10 %) were the major constituents of the stem oil. We found 73 previously unidentified components in these oils from G. bicolor. The oils were also subjected to odor evaluation. Eleven and 12 aroma-active compounds were detected in the leaf and stem oils, respectively. The abilities of these oils to inhibit acetylcholinesterase (AChE) activity were determined. The sesquiterpenoids in the oils were found to inhibit AChE activity more strongly than the monoterpenoids in the oils did. It was suggested that the three main components in each essential oil act synergistically against AChE activity. These results show that the essential oils obtained from G. bicolor are a good dietary source of AChE activity inhibition.

Topics: Acetylcholinesterase; Acyclic Monoterpenes; Alkenes; Asteraceae; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cholinesterase Inhibitors; Gas Chromatography-Mass Spectrometry; Humans; Monoterpenes; Odorants; Oils, Volatile; Plant Extracts; Plant Leaves; Plant Stems; Polycyclic Sesquiterpenes; Sesquiterpenes

The composition and variability of the terpenes and their derivatives isolated from the needles of a representative pool of 114 adult trees originating from four natural populations of dwarf mountain pine (Pinus mugo Turra) from the Julian Alps were investigated by GC-FID and GC/MS analyses. In total, 54 of the 57 detected essential-oil components were identified. Among the different compound classes present in the essential oils, the chief constituents belonged to the monoterpenes, comprising an average content of 79.67% of the total oil composition (74.80% of monoterpene hydrocarbons and 4.87% of oxygenated monoterpenes). Sesquiterpenes were present in smaller amounts (average content of 19.02%), out of which 16.39% were sesquiterpene hydrocarbons and 2.62% oxygenated sesquiterpenes. The most abundant components in the needle essential oils were the monoterpenes δ-car-3-ene, β-phellandrene, α-pinene, β-myrcene, and β-pinene and the sesquiterpene β-caryophyllene. From the total data set of 57 detected compounds, 40 were selected for principal-component analysis (PCA), discriminant analysis (DA), and cluster analysis (CA). The overlap tendency of the four populations suggested by PCA, was as well observed by DA. CA also demonstrated similarity among the populations, which was the highest between Populations I and II.

Topics: Acyclic Monoterpenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cluster Analysis; Cyclohexane Monoterpenes; Cyclohexenes; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Pinus; Polycyclic Sesquiterpenes; Principal Component Analysis; Sesquiterpenes

Essential oil from fresh leaves of the shrub Piper corcovadensis (Miq.) C. DC was obtained in 0.21% (w/w) yield by hydrodistillation in a Clevenger type apparatus. Thirty-one components, accounting for 96.61% of the leaf oil, were identified by gas chromatography-mass spectrometry. The major constituents of the oil were 1-butyl-3,4-methylenedioxybenzene (30.62%), terpinolene (17.44%), trans -caryophyllene (6.27%), α-pinene (5.92%), δ-cadinene (4.92%), and Limonene (4.46%). Bioassays against larvae of the Dengue mosquito (Aedes aegypti) revealed that leaf oil (LC50 = 30.52 ppm), terpinolene (LC50 = 31.16 ppm), and pure 1-butyl-3,4-methylenedioxybenzene (LC50 = 22.1 ppm) possessed larvicidal activities and are able to interfere with the activity of proteases from L4 gut enzymes. Additionally, the essential oil exhibited a strong oviposition deterrent activity at 50 and 5 ppm. This paper constitutes the first report of biological activities associated with the essential oil of leaves of P. corcovadensis.

Topics: Aedes; Animals; Bicyclic Monoterpenes; Biological Assay; Cyclohexane Monoterpenes; Cyclohexenes; Dengue; Electrophoresis, Polyacrylamide Gel; Gas Chromatography-Mass Spectrometry; Larva; Limonene; Monoterpenes; Mosquito Vectors; Oils, Volatile; Oviposition; Peptide Hydrolases; Piper; Plant Leaves; Polycyclic Sesquiterpenes; Protease Inhibitors; Sesquiterpenes; Terpenes; Trypsin

In this study the chemical composition of the essential oil from aerial parts of Moluccella spinosa L. collected in Sicily was evaluated by GC and GC-MS. The main components of M. spinosa L. were α-pinene (26.6%), caryophyllene oxide (16.8%) and β-caryophyllene (8.6%). A comparison with other studied oils of genus Moluccella is made. Antibacterial and antifungal activities against some microorganisms infesting historical textiles were also determined.

Topics: Anti-Bacterial Agents; Antifungal Agents; Bicyclic Monoterpenes; Lamiaceae; Microbial Sensitivity Tests; Monoterpenes; Oils, Volatile; Plant Components, Aerial; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Sicily; Textiles

The chemical composition of essential oils obtained from the hydrodistillation of different parts of Amomum maximum Roxb and Amomum muricarpum C. F. Liang & D. Fang (Zingiberaceae) grown in Vietnam are reported. The analysis was performed by means of gas chromatography-flame ionisation detectoorand gas chromatography coupled with mass spectrometry. The major compounds identified in the oils of A. maximum were β-pinene (20.4-40.8%), α-pinene (6.8-15.0%), β-elemene (2.5-12.8%) and β-caryophyllene (2.3-10.3%). Moreover, β-phellandrene (11.6%) was present in the root oil. The main compound identified in all the oil samples of A. muricarpum was α-pinene (24.1-54.7%) and β-pinene (9.2-25.9%). In addition, limonene (7.4%) and δ-3-carene (9.4%) were present in the leaves and stem oils, respectively. However, while β-phellandrene (8.3%) could be seen prominent in the root oil, the fruits contained significant amount of zingiberene (6.3%). The largest amount of τ-muurolol (13.0%) was found in the flower oil.

Topics: Amomum; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexane Monoterpenes; Cyclohexenes; Gas Chromatography-Mass Spectrometry; Limonene; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Leaves; Plant Oils; Plant Roots; Plant Stems; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Vietnam; Volatile Organic Compounds

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

The reactivity of secondary organic material (SOM) of variable viscosity, ranging from nonliquid to liquid physical states, was studied. The SOM, produced in aerosol form from terpenoid and aromatic precursor species, was reacted with ammonia at variable relative humidity (RH). The ammonium-to-organic mass ratio (MNH4+/MOrg) increased monotonically from <5% RH to a limiting value at a threshold RH, implicating a transition from particle reactivity limited by diffusion at low RH to one limited by other factors at higher RH. For the studied size distributions and reaction times, the transition corresponded to a diffusivity above 10-17.5 ± 0.5 m2 s-1. The threshold RH values for the transition were <5% RH for isoprene-derived SOM, 35-45% RH for SOM derived from α-pinene, toluene, m-xylene, and 1,3,5-trimethylbenzene, and >90% for β-caryophyllene-derived SOM. The transition RH for reactivity differed in all cases from the transition RH of a nonliquid to a liquid state. For instance, for α-pinene-derived SOM the transition for chemical reactivity of 35-45% RH can be compared to the nonliquid to liquid transition of 65-90% RH. These differences imply that chemical transport models of atmospheric chemistry should not use the SOM liquid to nonliquid phase transition as one-to-one surrogates of SOM reactivity.

Topics: Aerosols; Ammonia; Benzene Derivatives; Bicyclic Monoterpenes; Butadienes; Diffusion; Hemiterpenes; Humidity; Monoterpenes; Pentanes; Phase Transition; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Toluene; Viscosity; Xylenes

Amomum maximum Roxb. is a perennial herb distributed in South China and Southeast Asia. The objective of this work was to analyze the chemical constituents and assess insecticidal and repellent activities of the essential oil from Amomum maximum fruits against Tribolium castaneum (Herbst) and Liposcelis bostrychophila (Badonnel). The essential oil was obtained by hydrodistillation and analyzed by gas chromatography-flame ionization detector and gas chromatography-mass spectrometry. The main components of the essential oil were identified to be β-pinene (23.39%), β-caryophyllene (16.43%), α-pinene (7.55%), sylvestrene (6.61%) and ç-cadinene (4.19%). It was found that the essential oil of A. maximum fruits possessed contact and fumigant toxicities against T. castaneum adults (LD50 = 29.57 μg/adult and LC(50) = 23.09 mg/L air, respectively) and showed contact toxicity against L. bostrychophila (LD(50) = 67.46 μg/cm(2)). Repellency of the crude oil was also evaluated. After 2 h treatment, the essential oil possessed 100% repellency at 78.63 nL/cm(2) against T. castaneum and 84% repellency at 63.17 nL/cm(2) against L. bostrychophila. The results indicated that the essential oil of A. maximum fruits had the potential to be developed as a natural insecticide and repellent for control of T. castaneum and L. bostrychophila.

Topics: Amomum; Animals; Asia, Southeastern; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; China; Distillation; Flame Ionization; Fruit; Fumigation; Gas Chromatography-Mass Spectrometry; Insect Repellents; Insecticides; Lethal Dose 50; Monoterpenes; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Tribolium

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

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

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

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

Essential oils of the resins of Pinus brutia and Pinus pinea were evaluated for their biological potential. Essential oils were characterized using GC-MS and GC/FID. in vitro antimicrobial, phytotoxic, antioxidant, and insecticidal activities were carried out using the direct contact and the fumigant assays, respectively. The chemical profile of the essential oils of the resins of P. pinea and P. brutia included mainly α-pinene (21.39% and 25.40%), β-pinene (9.68% and 9.69%), and caryophyllene (9.12% and 4.81%). The essential oils of P. pinea and P. brutia exerted notable antimicrobial activities on Micrococcus luteus and Bacillus subtilis, insecticidal activities on Ephestia kuehniella eggs, phytotoxic activities on Lactuca sativa, Lepidium sativum, and Portulaca oleracea, as well as antioxidant potential. Indications of the biological activities of the essential oils suggest their use in the formulation of ecofriendly and biocompatible pharmaceuticals.

Topics: Animals; Anti-Infective Agents; Antioxidants; Bacillus subtilis; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Gas Chromatography-Mass Spectrometry; Insecta; Insecticides; Lactuca; Lepidium; Mediterranean Region; Micrococcus luteus; Monoterpenes; Oils, Volatile; Pinus; Plant Extracts; Plant Oils; Polycyclic Sesquiterpenes; Portulaca; Resins, Plant; Sesquiterpenes; Terpenes

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 defensive secretion of the frontal gland from termite soldiers is a mixture of monoterpenes, sesquiterpenes and diterpenes, the latter being the most representative. Analyses of the dichloromethane extract from soldiers of the Brazilian termite, Nasutitermes macrocephalus (Silvestri, 1903) (Isoptera, Nasutitermitinae), described for the first time, allowed to identify the presence of two monoterpenes (alpha-pinene and limonene) and two sesquiterpenes (beta-trans-caryophyllene and gamma-selinene) [corrected] by GC-EIMS, and the isolation of one rippertane and six trinervitane diterpenes by RP-HPLC. The chemical structures of the purified compounds were elucidated by interpretation of their spectroscopic data (1D and 2D NMR, EIMS, HRESIMS, and specific optical rotation) and the complete unequivocal assignment of the 3a-hydroxy-trinervita-1(15),8(19)-dien-2-one (6) was included in this paper, to complement the lack of information in the literature. Antibacterial, antifungal and cytotoxicity against cancer cell lines activities were evaluated. In particular, the compounds 2alpha,3beta-dihydroxytrinervita-l(15),8(19)-diene (2) and 3alpha-hydroxy-15-rippertene (7) exhibited the better activities against the clinically isolated Gram-positive bacterium methicillin-resistant Staphylococcus aureus BMB 9393, both with a MIC value of 31.2 microg mL(-1). This is the first description of a rippertane diterpene (7) as an antibacterial agent.

Topics: Animals; Anti-Infective Agents; Bicyclic Monoterpenes; Cell Line, Tumor; Cyclohexenes; Drug Screening Assays, Antitumor; Humans; Isoptera; Limonene; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Monoterpenes; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes

Essential oils hydrodistilled from the leaves and stem barks of Goniothalamus macrocalyx Ban., Goniothalamus albiflorus Ban. and Goniothalamus tamirensis Pierre ex Fin. & Gagnep. growing in Vietnam were analysed by gas chromatography (GC) and GC-coupled with mass spectrometry. α-Pinene (1.7-50.0%), β-pinene (tr-6.8%), β-myrcene (tr-1.5%), (E)-β-ocimene (tr-4.6%), β-caryophyllene (9.9-12.8%), aromadendrene (0.2-6.0%), α-humulene (1.7-6.9%), α-cadinol (1.2-14.5%), δ-cadinene (0.1-10.3%) and n-hexadecanoic acid (0.2-1.9%) were common to the oil samples. α-Pinene (50.0%) was the most abundant single constituent of the leaf oil of G. macrocalyx, whereas the major compounds of the stem were α-cadinol (14.5%), β-caryophyllene (10.3%) and octadecanoic acid (8.2%). Benzoic acid (18.4%), β-caryophyllene (12.4%) and α-pinene (10.3%) were present in the leaf of G. albiflorus, whereas limonene (21.2%), β-caryophyllene (12.8%) and α-phellandrene (9.3%) were identified in the stem. The leaf oil of G. tamirensis was characterised by abundance of α-pinene (33.4%), viridiflorol (18.5%) and β-caryophyllene (12.4%), whereas γ-gurjunene (11.2%), β-caryophyllene (10.9%) and δ-cadinene (10.3%) predominates in the stem oil.

Topics: Acyclic Monoterpenes; Alkenes; Azulenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Chromatography, Gas; Cyclohexane Monoterpenes; Gas Chromatography-Mass Spectrometry; Goniothalamus; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Bark; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes

Cotton plants accumulate gossypol and related sesquiterpene aldehydes, which function as phytoalexins against pathogens and feeding deterrents to herbivorous insects. However, to date little is known about the biosynthesis of volatile terpenes in this crop. Herein is reported that 5 monoterpenes and 11 sesquiterpenes from extracts of a glanded cotton cultivar, Gossypium hirsutum cv. CCRI12, were detected by gas chromatography-mass spectrometry (GC-MS). By EST data mining combined with Rapid Amplification of cDNA Ends (RACE), full-length cDNAs of three terpene synthases (TPSs), GhTPS1, GhTPS2 and GhTPS3 were isolated. By in vitro assays of the recombinant proteins, it was found that GhTPS1 and GhTPS2 are sesquiterpene synthases: the former converted farnesyl pyrophosphate (FPP) into β-caryophyllene and α-humulene in a ratio of 2:1, whereas the latter produced several sesquiterpenes with guaia-1(10),11-diene as the major product. By contrast, GhTPS3 is a monoterpene synthase, which produced α-pinene, β-pinene, β-phellandrene and trace amounts of other monoterpenes from geranyl pyrophosphate (GPP). The TPS activities were also supported by Virus Induced Gene Silencing (VIGS) in the cotton plant. GhTPS1 and GhTPS3 were highly expressed in the cotton plant overall, whereas GhTPS2 was expressed only in leaves. When stimulated by mechanical wounding, Verticillium dahliae (Vde) elicitor or methyl jasmonate (MeJA), production of terpenes and expression of the corresponding synthase genes were induced. These data demonstrate that the three genes account for the biosynthesis of volatile terpenes of cotton, at least of this Upland cotton.

Topics: Acetates; Alkyl and Aryl Transferases; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexane Monoterpenes; Cyclohexenes; Cyclopentanes; Gas Chromatography-Mass Spectrometry; Gossypium; Intramolecular Lyases; Monocyclic Sesquiterpenes; Monoterpenes; Oxylipins; Phytoalexins; Polycyclic Sesquiterpenes; Polyisoprenyl Phosphates; Sesquiterpenes; Sesquiterpenes, Guaiane; Terpenes; Volatile Organic Compounds

Cotton (Gossypium hirsutum L.) plants damaged by insects emit a blend of volatiles, including monoterpenes and sesquiterpenes, which can directly repel herbivores and/or indirectly protect the plant by attracting natural enemies of the herbivores. To understand the molecular basis of terpene biosynthesis and regulation in cotton, two terpene synthase genes, GhTPS1 and GhTPS2, were heterologously expressed and characterized. Recombinant GhTPS1 accepted farnesyl pyrophosphate as substrate and produced (E)-β-caryophyllene and α-humulene. GhTPS2 was characterized as a monoterpene synthase which formed α-pinene and β-pinene using geranyl pyrophosphate as substrate. Quantitative real-time PCR analysis revealed that GhTPS1 and GhTPS2 gene expression was elevated after methyl jasmonate (MeJA) treatment in cotton leaves. Moreover, feeding of the green plant bug Apolygus lucorum, a major cotton pest in northern China, resulted in increased GhTPS2 expression in young leaves, suggesting that GhTPS2 might be involved in plant defense in cotton.

Topics: Acetates; Adaptation, Physiological; Alkyl and Aryl Transferases; Animals; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Carbon-Oxygen Lyases; China; Cyclopentanes; Gene Expression; Genes, Plant; Gossypium; Herbivory; Insecta; Monocyclic Sesquiterpenes; Monoterpenes; Oxylipins; Plant Diseases; Plant Leaves; Plant Proteins; Polycyclic Sesquiterpenes; Polyisoprenyl Phosphates; Sesquiterpenes; Terpenes

Salvia x jamensis J. Compton is a hybrid between Salvia greggii A. Gray and Salvia microphylla Kunt. In this study, we describe three hair types identified by Scanning Electron Microscopy. In the essential oil of the aerial parts of S. jamensis 56 different compounds were identified. The two main constituents were β-caryophyllene (14.8%) and β-pinene (6.8%). Cytotoxic-apoptotic activity of S. x jamensis essential oil has been investigated by using U937 cell line. The essential oil EC50 for cell number and for cell apoptosis have been shown to be 360 and 320 µg mL(-1), respectively. Among the constituents of the oil examined, only β-caryophyllene, β-pinene and α-pinene displayed cytotoxic and apoptotic activities. For the first time, it has been demonstrated that some of the pure constituents identified within S. x jamensis essential oil are responsible for its cytotoxic-apoptotic activity when properly combined.

Topics: Apoptosis; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cell Line, Tumor; Humans; Microscopy, Electron, Scanning; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Salvia; Sesquiterpenes; Trichomes

Terpenes are specialized plant metabolites that act as attractants to pollinators and as defensive compounds against pathogens and herbivores, but they also play an important role in determining the quality of horticultural food products. We show that the genome of cultivated apple (Malus domestica) contains 55 putative terpene synthase (TPS) genes, of which only 10 are predicted to be functional. This low number of predicted functional TPS genes compared with other plant species was supported by the identification of only eight potentially functional TPS enzymes in apple 'Royal Gala' expressed sequence tag databases, including the previously characterized apple (E,E)-α-farnesene synthase. In planta functional characterization of these TPS enzymes showed that they could account for the majority of terpene volatiles produced in cv Royal Gala, including the sesquiterpenes germacrene-D and (E)-β-caryophyllene, the monoterpenes linalool and α-pinene, and the homoterpene (E)-4,8-dimethyl-1,3,7-nonatriene. Relative expression analysis of the TPS genes indicated that floral and vegetative tissues were the primary sites of terpene production in cv Royal Gala. However, production of cv Royal Gala floral-specific terpenes and TPS genes was observed in the fruit of some heritage apple cultivars. Our results suggest that the apple TPS gene family has been shaped by a combination of ancestral and more recent genome-wide duplication events. The relatively small number of functional enzymes suggests that the remaining terpenes produced in floral and vegetative and fruit tissues are maintained under a positive selective pressure, while the small number of terpenes found in the fruit of modern cultivars may be related to commercial breeding strategies.

Topics: Acyclic Monoterpenes; Alkyl and Aryl Transferases; Base Sequence; Bicyclic Monoterpenes; Flowers; Fruit; Gas Chromatography-Mass Spectrometry; Gene Expression Profiling; Gene Expression Regulation, Enzymologic; Gene Expression Regulation, Plant; Genomics; Malus; Molecular Sequence Data; Monoterpenes; Multigene Family; Phylogeny; Plant Proteins; Polycyclic Sesquiterpenes; Reverse Transcriptase Polymerase Chain Reaction; Sequence Homology, Nucleic Acid; Sesquiterpenes; Species Specificity; Terpenes; Volatile Organic Compounds; Volatilization

Ambient aerosol samples were collected at an urban site and an upwind rural site of Beijing during the CAREBEIJING-2008 (Campaigns of Air quality REsearch in BEIJING and surrounding region) summer field campaign. Contributions of primary particles and secondary organic aerosols (SOA) were estimated by chemical mass balance (CMB) modeling and tracer-yield method. The apportioned primary and secondary sources explain 73.8% ± 9.7% and 79.6% ± 10.1% of the measured OC at the urban and rural sites, respectively. Secondary organic carbon (SOC) contributes to 32.5 ± 15.9% of the organic carbon (OC) at the urban site, with 17.4 ± 7.6% from toluene, 9.7 ± 5.4% from isoprene, 5.1 ± 2.0% from α-pinene, and 2.3 ± 1.7% from β-caryophyllene. At the rural site, the secondary sources are responsible for 38.4 ± 14.4% of the OC, with the contributions of 17.3 ± 6.9%, 13.9 ± 9.1%, 5.6 ± 1.9%, and 1.7 ± 1.0% from toluene, isoprene, α-pinene, and β-caryophyllene, respectively. Compared with other regions in the world, SOA in Beijing is less aged, but the concentrations are much higher; between the sites, SOA is more aged and affected by regional transport at the urban site. The high SOA loading in Beijing is probably attributed to the high regional SOC background (~2 μg m(-3)). The toluene SOC concentration is high and comparable at the two sites, implying that some anthropogenic components, at least toluene SOA, are widespread in Beijing and represents a major factor in affecting the regional air quality. The aerosol gaseous precursor concentrations and temperature correlate well with SOA, both affecting SOA formation. The significant SOA enhancement with increasing water uptake and acidification indicates that the aqueous-phase reactions are largely responsible SOA formation in Beijing.

Topics: Aerosols; Air Pollutants; Air Pollution; Bicyclic Monoterpenes; Butadienes; Carbon; China; Hemiterpenes; Models, Molecular; Monoterpenes; Particle Size; Pentanes; Polycyclic Sesquiterpenes; Sesquiterpenes; Toluene

Tomato plants respond to herbivory by emitting volatile organic compounds (VOCs), which are released into the surrounding atmosphere. We analyzed the tomato herbivore-induced VOCs and tested the ability of tomato receiver plants to detect tomato donor volatiles by analyzing early responses, including plasma membrane potential (V(m)) variations and cytosolic calcium ([Ca²⁺](cyt)) fluxes. Receiver tomato plants responded within seconds to herbivore-induced VOCs with a strong V(m) depolarization, which was only partly recovered by fluxing receiver plants with clean air. Among emitted volatiles, we identified by GC-MS some green leaf volatiles (GLVs) such as (E)-2-hexenal, (Z)-3-hexenal, (Z)-3-hexenyl acetate, the monoterpene α-pinene, and the sesquiterpene β-caryophyllene. GLVs were found to exert the stronger V(m) depolarization, when compared to α-pinene and β-caryophyllene. Furthermore, V(m) depolarization was found to increase with increasing GLVs concentration. GLVs were also found to induce a strong [Ca²⁺](cyt) increase, particularly when (Z)-3-hexenyl acetate was tested both in solution and with a gas. On the other hand, α-pinene and β-caryophyllene, which also induced a significant V(m) depolarization with respect to controls, did not exert any significant effect on [Ca²⁺](cyt) homeostasis. Our results show for the first time that plant perception of volatile cues (especially GLVs) from the surrounding environment is mediated by early events, occurring within seconds and involving the alteration of the plasma membrane potential and the [Ca²⁺](cyt) flux.

Topics: Acetates; Aldehydes; Animals; Bicyclic Monoterpenes; Calcium; Cell Membrane; Cytosol; Ecosystem; Gas Chromatography-Mass Spectrometry; Herbivory; Host-Parasite Interactions; Membrane Potentials; Monoterpenes; Moths; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Signal Transduction; Solanum lycopersicum; Spodoptera; Time Factors; Volatile Organic Compounds

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

Herbivory, mechanical injury or pathogen infestation to vegetative tissues can induce volatile organic compounds (VOCs) production, which can provide defensive functions to injured and uninjured plants. In our studies with 'McNeal' wheat, 'Otana' oat, and 'Harrington' barley, plants that were mechanically injured, attacked by either of two Oulema spp. (melanopus or cyanella) beetles, or infected by one of the three Fusarium spp. (graminearum, avenaceum, or culmorum), had significant VOC induction compared to undamaged plants. Mechanical injury to the main stem or one leaf caused the induction of one green leaf volatile (GLV) - (Z)-3-hexenol, and three terpenes (β-linalool, β-caryophyllene, and α-pinene) with all three grasses; wheat and barley also showed β-linalool oxide induction. The blend of induced VOCs after Fusarium spp. infestation or Oulema spp. herbivory was dominated by GLVs ((Z)-3-hexenal, (E)-2-hexenal, (E)-2-hexenol, (Z)-3-hexenyl acetate, and 1-hexenyl acetate) and β-linalool and β-caryophyllene; beetle herbivory also induced (E)-β-farnesene. Different ratios of individual VOCs were induced between the two Oulema spp. for each cereal grass and different ratios across the three cereals for each beetle species. Also, different ratios of individual VOCs were induced between the three Fusarium spp. for each cereal grass and different ratios across the three cereals for each fungal pathogen species. Our results are preliminary since we could not simultaneously measure VOC induction from controls with each of the ten different injury treatments for each of the three cereals. However, the comparison of mechanical injury, insect herbivory, and fungal infection has not been previously examined with VOC responses from three different plant species within the same family. Also, our work suggests large qualitative and quantitative overlap of VOC induction from plants of all three cereals having beetle herbivory injury when compared to infection injury from necrotrophic fungal pathogens.

Topics: Acyclic Monoterpenes; Animals; Bicyclic Monoterpenes; Coleoptera; Fusarium; Hexanols; Monoterpenes; Plant Diseases; Plant Leaves; Poaceae; Polycyclic Sesquiterpenes; Sesquiterpenes; 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

Secondary organic aerosol (SOA) consists of compounds with a wide range of volatilities and its ambient concentration is sensitive to this volatility distribution. Recent field studies have shown that the typical mass spectrum of ambient oxygenated organic aerosol (OOA) as measured by the Aerodyne Aerosol Mass Spectrometer (AMS) is quite different from the SOA mass spectra reported in smog chamber experiments. Part of this discrepancy is due to the dependence of SOA composition on the organic aerosol concentration. High precursor concentrations lead to higher concentrations of the more volatile species in the produced SOA while at lower concentrations the less volatile compounds dominate the SOA composition. alpha-Pinene, beta-pinene, d-limonene, and beta-caryophyllene ozonolysis experiments were performed at moderate concentration levels. Using a thermodenuder the more volatile SOA species were removed achieving even lower SOA concentration. The less volatile fraction was then chemically characterized by an AMS. The signal fraction of m/z44, and thus the concentration of C02+, is significantly higher for the less volatile SOA. High NO(x) conditions result in less oxidized SOA than low NO(x) conditions, while increasing relative humidity levels results in more oxidized products for limonene but has little effect on alpha-and beta-pinene SOA. Combining a smog chamber with a thermodenuder model employing the volatility basis-set framework, the AMS SOA mass spectrum for each experiment and for each precursor is deconvoluted into low, medium, and high volatility component mass spectra. The spectrum of the surrogate component with the lower volatility is quite similar to that of ambient OOA.

Topics: Aerosols; Air Pollutants; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Environmental Monitoring; Mass Spectrometry; Monoterpenes; Organic Chemicals; Oxygen; Ozone; Polycyclic Sesquiterpenes; Sesquiterpenes; Smog; Temperature; Terpenes

Secondary organic carbon (SOC) concentrations in steady-state aerosol were measured in a series of alpha-pinene/NOx and one series of beta-caryophyllene/NOx irradiation experiments. The acidity of the inorganic seed aerosol was varied while the hydrocarbon and NOx concentrations were held constant in each series of experiments. Measurements were made for acidity levels and SOC concentrations much closer to ambient levels than had been previously achieved for alpha-pinene, while there are no previous measurements for SOC increases due to acidity for beta-caryophyllene. The observed enhancement in SOC concentration linearly increases with the measured hydrogen ion concentration in air for each system. For the conditions of these studies, SOC increased by 0.04% per nmol H+ m(-3) for alpha-pinene under two conditions where the organic carbon concentration differed by a factor of 5. For alpha-pinene, this level of response to acidic aerosol was a factor of 8 lower than was reported by Surratt et al. for similar series of experiments for SOC from the photooxidation of isoprene/NOx mixtures. By contrast, SOC from beta-caryophyllene showed an increase of 0.22% per nmol H+ m(-3), roughly two-thirds of the response in the isoprene system. Mass fractions for SOC particle-phase tracers for alpha-pinene decreased slightly with increasing aerosol acidity, although remaining within previously stated uncertainties. Below 200 nmol H+ m(-3), the mass fraction of beta-caryophyllenic acid, the only identified tracer for beta-caryophyllene SOC, was constant although beta-caryophyllenic acid showed a substantial decrease for acidities greater than 400 nmol H+ m(-3).

Topics: Aerosols; Air Pollutants; Bicyclic Monoterpenes; Hydrogen-Ion Concentration; Monoterpenes; Nitrogen Oxides; Polycyclic Sesquiterpenes; Sesquiterpenes; Ultraviolet Rays

The essential-oil compositions of Pinus heldreichii Christ. from Montenegro and Serbia are reported at the population level. Whitebark pine is a sub-endemic high-mountain Balkan pine relict of an anthropogenically reduced area, with large morphological diversity and insufficiently clear taxonomic position. In the pine-needle terpene profile from three populations from Montenegro, and one from Serbia, 101 compounds were detected, 72 of which could be identified (Table 3). The dominant constituents are limonene (26.3%), alpha-pinene (17.5%), germacrene D (13.5%), and beta-caryophyllene (10.4%), comprising ca. 67.7% of the essential oil. Medium-to-high contents (0.5-10%) of the following 16 additional components were found: beta-pinene, beta-myrcene, alpha-humulene, delta-cadinene, alpha-muurolene, (E)-hex-2-enal, beta-gurjunene, gamma-muurolene, isopimarol, camphene, gamma-cadinene, aromadendrene, beta-bisabolene, trans-beta-farnesene, alpha-cadinene, and (Z)-hex-3-en-1-ol. The similarity of the populations and the within-population variability was visualized by principle-component analysis (PCA) of eleven selected terpenes in 97 tree samples. Cluster and genetic analyses suggest closest connection between the two spatially most-distant populations I (Montenegro) and IV (Serbia). Based on the profile of the main sesquiterpene components, the studied populations from Montenegro and Serbia are more similar to the populations from Greece and the Central Balkan peninsula (Bosnia and Serbia-Kosovo) than to those on the furthest eastern margin of their natural range (Bulgaria).

Topics: Acyclic Monoterpenes; Azulenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexenes; Limonene; Monoterpenes; Oils, Volatile; Pinus; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Yugoslavia

Some essential oils obtained from the branches of four Pinus species (P. pinea L., P. halepensis Mill., P. pinaster Soil in Ait., and P. nigra Arnold) have been evaluated for their acaricidal activity by aerial diffusion against the stored food mite Tyrophagus putrescentiae (L.). All the essential oils showed a good efficacy, but P. pinea oil and its two constituents 1,8-cineole and limonene were the most effective compounds, showing 100% acaricidal activity at 8 microL; 1,8-cineole showed the same activity at 6 microL.

Topics: Acyclic Monoterpenes; Animals; Bicyclic Monoterpenes; Cyclohexanols; Cyclohexenes; Eucalyptol; Food Contamination; Insecticides; Limonene; Mites; Monoterpenes; Oils, Volatile; Pinus; Plant Oils; Plant Structures; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes

Volatile compounds were isolated from Costa Rican guava fruit by simultaneous steam distillation-solvent extraction according to the Likens-Nickerson method. Compounds were identified by capillary GC-MS and sensorially characterized by sniffing-GC. One hundred and seventy-three components were identified in the aroma concentrate, from which (E)-beta-caryophyllene, alpha-terpineol, alpha-pinene, alpha-selinene, beta-selinene, delta-cadinene, 4,11-selinadiene, and alpha-copaene were found to be the major constituents. The amounts of aliphatic esters and terpenic compounds were thought to contribute to the unique flavor of this fruit.

Topics: Bicyclic Monoterpenes; Chromatography, Gas; Costa Rica; Cyclohexane Monoterpenes; Cyclohexenes; Esters; Fruit; Gas Chromatography-Mass Spectrometry; Humans; Monoterpenes; Odorants; Polycyclic Sesquiterpenes; Psidium; Sesquiterpenes; Smell; Taste; Terpenes; Volatilization

Headspace solid-phase microextraction coupled to gas chromatography/ion trap mass spectrometry-65 microm polydimethylsiloxane/divinylbenzene (PDMS/DVB) was used to identify and monitor the emission patterns of biogenic volatile organic compounds from leaves of Eucalyptus dunnii, Eucalyptus saligna, and Eucalyptus citriodora in situ. Short extractions (1 min) were performed every 30 min for periods of 8-10 h during 24 days taking advantage of the high capacity of this porous polymer coating. Forty-two compounds were detected and 20 identified in the headspace of E. saligna leaves, and 19 of 27 compounds were identified in the headspace of E. dunnii leaves. The emission pattern of (E)-beta-ocimene and rose oxide suggests that they may play a bioactive role in Eucalyptus.

Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Cymenes; Eucalyptus; Gas Chromatography-Mass Spectrometry; Monoterpenes; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Volatilization

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

We examined the effects of six volatile compounds on alfalfa pellet consumption by lambs. In each experiment, 45 lambs were individually fed alfalfa pellets sprayed with a selected compound (camphor, limonene, cis-jasmone, beta-caryophyllene, borneol, or alpha-pinene) at one of five concentrations. Treatment concentrations were multiples (0, .5, 1, 2, and 10) of the concentration of a specific compound (X) that was related to differential herbivory of tarbush by livestock in previous studies. Treatments were applied to alfalfa pellets (.64 kg x lamb(-1) x d(-1), DM basis), and consumption was measured during a 20-min interval each morning for 5 d. Lambs were adapted to handling procedures and the pelleted diet (without treatments) for 10 d. Lambs were maintained and fed (approximately 4.5 to 5% of BW) as one group except during 20-min tests. A negative linear effect of treatment concentration on intake was observed for camphor (P < .02) and alpha-pinene (P < .01), and a quadratic response was detected for borneol (P < .02). The other three compounds had no discernible effect on consumption. Although volatile compounds generally had only minor influences on consumption, the negative influences of alpha-pinene and camphor concentrations on pellet consumption suggest that these monoterpenes may partially explain differential herbivory of individual tarbush plants by livestock.

Topics: Administration, Oral; Analysis of Variance; Animals; Bicyclic Monoterpenes; Camphanes; Camphor; Cyclohexenes; Cyclopentanes; Diet; Digestion; Dose-Response Relationship, Drug; Eating; Limonene; Medicago sativa; Monoterpenes; Oxylipins; Polycyclic Sesquiterpenes; Random Allocation; Sesquiterpenes; Sheep; Terpenes; Time Factors

The chemical constituents of volatile oils of Metasequoia glyptostroboides leave were analyzed by GC-MS-DS. 27 constituents were identified, alpha-pinene (70.65%) and caryophyllene (10.38%) of them are main components.

Topics: Bicyclic Monoterpenes; Chromatography, Gas; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Plant Leaves; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes

The chemical constituents of the essential oils obtained from the leaves of Vitex negundo var. cannabifolia, V. negundo var. heterophylla, V. negundo and V. trifolia were analysed by GC-MS. Forty compounds including alpha-pinene, linalool, terpinyl acetate, beta-caryophyllene and caryophyllene oxide, etc. were identified. Their percentages in oils were given.

Topics: Acyclic Monoterpenes; Bicyclic Monoterpenes; Drugs, Chinese Herbal; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes