caryophyllene and beta-phellandrene

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

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

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 volatile components of Murraya koenigii fresh leaves, collected from Surat Thani province, Thailand were studied by using headspace (HS) solid-phase microextraction (SPME) coupled with gas chromatography-mass spectrometry (GC-MS). The four fibers employed to extract the volatiles were polydimethylsiloxane (PDMS), polydimethylsiloxane-divinylbenzene (PDMS-DVB), carboxane-polydimethylsiloxane (CAR-PDMS) and polydimethylsiloxane-divinylbenzene-carboxane (PDMS-DVB-CAR). The volatile constituents of M. koenigii fresh leaves were also extracted by hydrodistillation and analyzed by GC-MS. Fifty-one compounds were identified by these fibers. Five major compounds, γ-terpinene, β-caryophyllene, β-phellandrene, a-selinene and a-pinene, were detected in all fibers. The PDMS-DVB-CAR fiber was considered as the best for trapping key volatiles of M. koenigii fresh leaves.

Topics: Cyclohexane Monoterpenes; Cyclohexenes; Gas Chromatography-Mass Spectrometry; Monoterpenes; Murraya; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Solid Phase Microextraction

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

Volatiles emitted from the leaves of Lycopersicon esculentum at the two-, ten-leaf and anthesis periods were collected by a gas absorbing method and analyzed by gas chromatography (GC)-mass spectrometry. In total, 33 compounds of volatiles emitted from three developmental stage plants were separated and identified, and quantitatively analyzed by the internal standard addition method. All of the samples of volatile were found to be rich in monoterpenes and sesquiterpenes. beta-phellandrene and caryophyllene predominated in the volatiles of the leaves of plants at the two- and ten-leaf stages. Furthermore, (E)-2-hexenal were the dominant components in the volatiles emitted from anthesis plants. The results of volatiles analyzed show that the compositions varied depending on the developmental stages. The volatiles emitted from crushed tomato leaves of plants at the anthesis stage had the most strongly inhibitory activity against the spore germination and hyphal growth of Botrytis cinerea and Fusarium oxysporum, followed by ten- and two-leaf plants. However, the activity of volatiles, emitted from the leaves of plants at the two-leaf stage, in inhibiting F. oxysporum was greater than B. cinerea.

Topics: Botrytis; Cyclohexane Monoterpenes; Cyclohexenes; Fusarium; Gas Chromatography-Mass Spectrometry; Hexobarbital; Hyphae; Monoterpenes; Plant Exudates; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Solanum lycopersicum; Spores, Fungal; Volatilization