caryophyllene and gamma-terpinene

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

A greenhouse experiment was conducted to study the effects of four irrigation intervals (4, 8, 12, and 16 days) and six harvests (2, 4, 6, 8, 10, and 12 months after transplanting) on biomass, essential oil content, and composition of Plectranthus amboinicus (Lour.) Spreng. Fresh weight and essential oil yield decreased with increasing irrigation interval; whereas, essential oil content was stimulated by water stress and increased as the irrigation interval increased. Fresh weight of Plectranthus amboinicus irrigated every 4 days peaked when harvested at 6 months, but essential oil content peaked when irrigated every 16 days and harvested at 2 months after transplantation. On the other hand, essential oil yield peaked when irrigated every 8 days and harvested at 6 months. Thymol, p-cymene, γ-terpinene, and β-caryophyllene were the major compounds, and they peaked at different irrigation intervals and harvest times. This study showed biomass, essential oil content, and yield as well as the major and minor constituents of Plectranthus amboinicus are influenced by irrigation interval and the timing of harvest.

Topics: Agricultural Irrigation; Biomass; Crop Production; Cyclohexane Monoterpenes; Cymenes; Monoterpenes; Oils, Volatile; Plectranthus; Polycyclic Sesquiterpenes; Sesquiterpenes; Stress, Physiological; Thymol; Time Factors; Water

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

Essential oil composition of Plectranthus asirensis grown in Saudi Arabia was chemically analysed for the first time by various gas chromatography techniques (GC-MS, GC-FID, Co-GC, LRI determination and database and literature searches) using two different stationary phase columns (polar and nonpolar). This analysis led to the characterisation of a total of 124 components representing 98.5% of the total oil composition. The results revealed that P. asirensis oil was mainly dominated by monoterpenoids (90.7%) in which most representative constituents were thymol (66.0 ± 0.36%), γ-terpinene (14.0 ± 0.18%), p-cymene (5.2 ± 0.06%) and β-caryophyllene (3.0 ± 0.03%). It is worth mentioning here that this is the first report on the phytochemical constituents of P. asirensis.

Topics: Chromatography, Gas; Cyclohexane Monoterpenes; Cymenes; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Plectranthus; Polycyclic Sesquiterpenes; Saudi Arabia; Sesquiterpenes; Thymol

This study was conducted to evaluate the phytochemical composition and larvicidal effect of leaf essential oil from Murraya exotica against early fourth-instar larvae of Aedes aegypti, Anopheles stephensi and Culex quinquefasciatus. Gas chromatography (GC) and gas chromatography mass spectrometry (GC-MS) analyses revealed that the essential oil contained 27 components. The major chemical components identified were β-humulene (40.62%), benzyl benzoate (23.96%), β-caryophyllene (7.05%) and α-terpinene (5.66%). The larval mortality was observed after 12 and 24 h of exposure period. The results revealed that essential oil showed varied levels of larvicidal activity against A. aegypti, A. stephensi and C. quinquefasciatus. After 12 h of exposure period, the larvicidal activities were LC₅₀ = 74.7 and LC₉₀ = 152.7 ppm (A. aegypti), LC₅₀ = 56.3 and LC₉₀ = 107.8 ppm (A. stephensi ), and LC₅₀ = 74.4 and LC₉₀ = 136.9 ppm (C. quinquefasciatus) and the larvicidal activities after 24 h of exposure period were LC₅₀ = 35.8 and LC₉₀ = 85.4 ppm (A. aegypti), LC₅₀ = 31.3 and LC₉₀ = 75.1 ppm (A. stephensi), and LC₅₀ = 43.2 and LC₉₀ = 103.2 ppm (C. quinquefasciatus). These results suggest that leaf essential oil from M. exotica is a promising and eco-friendly source of natural larvicidal agent against A. aegypti, A. stephensi and C. quinquefasciatus.

Topics: Aedes; Animals; Anopheles; Benzoates; Culex; Cyclohexane Monoterpenes; Insecticides; Larva; Monocyclic Sesquiterpenes; Monoterpenes; Murraya; Oils, Volatile; Plant Leaves; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes

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

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

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

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

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

Solid-phase microextraction technique coupled with gas chromatography-flame ionisation detector and gas chromatography-mass spectrometry was used to investigate the inter- and intra-population chemical polymorphism in volatile constituents of three populations of Thymus pannonicus growing in Slovakia. To have an idea on what really the plant emits under different environmental and physiological conditions, a total of 86 individuals were separately analysed using low extraction temperatures (30°C). Data were analysed using a chemometric approach such as the principal component analysis which revealed a significant intra-population variability with the existence of up to four chemotypes: the most abundant is the p-cymene/γ-terpinene chemotype, followed by the geraniol and linalool chemotypes, and, only in one population, by the γ-muurolene/(E)-caryophyllene chemotype. This differentiation of individual plants inside the populations allows better adaptation to ecological conditions of localities and is probably connected with intrinsic genetic diversity of the species.

Topics: Acyclic Monoterpenes; Cyclohexane Monoterpenes; Cymenes; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Principal Component Analysis; Sesquiterpenes; Slovakia; Solid Phase Microextraction; Terpenes; Thymus Plant

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

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

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

The need for new anthelmintic with no chemical residues is becoming urgent. In a program aiming at the evaluation of plant as sources of new active molecules, the anthelmintic activities of the essential oils (EOs) obtained from either Zanthoxylum zanthoxyloides seeds or Newbouldia laevis leaves were evaluated against Strongyloides ratti by analyzing the results of two in vitro bioassays. These two plants and their tested parts were retained after an ethnopharmacology survey that confirmed their use by small-scale farmers for treatment of small ruminants affected by digestive helminths. The plants were harvested in Benin, and their EO were obtained by hydrodistillation. The EO yield of extraction was 0.65% (w/w) of for Z. zanthoxyloides seeds and 0.05% (w/w) for N. laevis. The chemical compositions of the two EOs were analyzed by gas chromatography coupled with mass spectrometry. The major constituents of the EO from Z. zanthoxyloides consisted of the following compounds: γ-terpinene (18 %), undecane (15 %), valencene (8.3 %), decanal (8.3 %), and 3-carene (6.7 %). In contrast, the major constituents of the EO from N. laevis leaves consisted of the following compounds: β-caryophyllene (36 %) and eugenol (5.8 %). An egg-hatching inhibition (EHI) assay was developed and a larval migration inhibition assay was used on S. ratti to examine the effects of the EOs and to evidence their inhibitory concentrations (IC(50) and IC(90)) values on this nematode. Furthermore, the toxicity of the two EOs on Vero cell line was evaluated. When tested on S. ratti egg hatching, the two EOs resulted in similar IC(50) values (19.5 and 18.2 μg/ml for Z. zanthoxyloides and N. laevis, respectively), which were about sevenfold higher than that of the control (thiabendazole, IC(50) = 2.5 μg/ml). Larval migration was inhibited at similar concentrations for: Z. zanthoxyloides (IC(50) = 46 μg/ml), N. laevis (IC(50) = 51 μg/ml), and the control [levamisole (IC(50) = 36 μg/ml)]. No cytotoxicity was found on Vero cells because both EOs had IC(50) values higher than 50 μg/ml. Therefore, we have concluded that the EOs from two plants, used in folk medicine, may contain compounds with anthelmintic activity and could be used as improved traditional medicines or, at least, as food additives in a combined treatment for the control of helminth infections.

Topics: Aldehydes; Alkanes; Animals; Anthelmintics; Benin; Bicyclic Monoterpenes; Bignoniaceae; Chlorocebus aethiops; Cyclohexane Monoterpenes; Inhibitory Concentration 50; Levamisole; Male; Medicine, Traditional; Monoterpenes; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Rats; Rats, Wistar; Sesquiterpenes; Strongyloides ratti; Thiabendazole; Vero Cells; Zanthoxylum

In the present study, we reported a comparative analysis of the chemical composition and pharmacological properties of the essential oils obtained from 2 Mexican oreganos, Poliomintha longiflora and Lippia graveolens. The gas chromatography-mass spectrometry (GC-MS) profiles of the oils showed high amounts of oxygenated monoterpenes, mainly carvacrol (%[mg/100 g dry matter]) (18.36 [459.0] in P. longiflora and 13.48 [164.7] in L. graveolens). In addition, these oils contained marked quantities of p-cymene (14.09 [352.2] and 7.46 [37.3], respectively), β-caryophyllene oxide, β-caryophyllene, and carvacrol acetate. Headspace analyses of the leaves of both species using different coated fibers revealed that γ-terpinene, eucalyptol, and p-cymene were the principal light volatile components. Chromatographic fingerprints and a suitable analytical method for quantifying the main components of both essences were established using high-performance liquid chromatography (HPLC) as analytical tool. The essential oils of both species were not toxic in the acute toxicity studies in mice performed according to the Lorke procedure (DL(50) > 5000 mg/kg). The oils and the major constituents, carvacrol and p-cymene, displayed a moderate in vitro antibacterial activity, with minimum inhibitory concentration values ranging from 128 to 512 μg/mL. In addition, these samples demonstrated a marginal antispasmodic activity in vivo and provoked a concentration-dependent inhibition of the carbachol- and histamine-induced contractions using the isolated guinea-pig ileum preparation. In particular, p-cymene exerts good selective inhibitory activity on the carbachol-induced contractions (IC(50) = 9.85 μg/mL).. The analytical methods using GC-MS and HPLC techniques will be useful for establishing quality control as well as preclinical pharmacological and toxicological parameters of the crude drug P. longiflora, which is widely used as substitute of L. graveolens for medicinal and flavorings purposes. This overall information will be also useful for elaborating scientific and pharmacopoeic monographs of this very Mexican medicinal plant.

Topics: Animals; Anti-Bacterial Agents; Chromatography, High Pressure Liquid; Cyclohexane Monoterpenes; Cyclohexanols; Cymenes; Eucalyptol; Gas Chromatography-Mass Spectrometry; Gastrointestinal Motility; Guinea Pigs; Lamiaceae; Lippia; Male; Mice; Mice, Inbred ICR; Microbial Sensitivity Tests; Monoterpenes; Oils, Volatile; Origanum; Parasympatholytics; Plant Extracts; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes

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

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

The volatile composition of the headspace from Citrus unshiu Marcov. forma Miyagawa-wase blossom was investigated. The volatile constituents were absorbed by a solid-phase microextraction (SPME) fiber and directly transferred to a GC-MS. Volatile compositional changes of C. unshiu blossom prepared via different drying methods (shade, microwave, and freeze-drying methods) were also determined. A total of 96 volatile constituents were confirmed in the headspace from these samples. Monoterpene hydrocarbons were prominent in the headspace volatiles of C. unshiu blossom: fresh, 84.1%; shade-dried, 60.0%; microwave-dried, 88.4%; and freeze-dried, 29.9%. p-Cymene (23.3%) was the most abundant component in the headspace of fresh C. unshiu blossom; gamma-terpinene was the most abundant in shade- and microwave-dried samples (26.8 and 31.2%, respectively) and beta-caryophyllene (10.5%) in freeze-dried sample. By using an electronic nose consisting of six metal oxide sensors, principal component analysis of the volatile compounds showed a clear aroma discrimination of the fresh and all dried blossom samples.

Topics: Chromatography, Gas; Citrus; Cyclohexane Monoterpenes; Cyclohexenes; Electronics; Flowers; Freeze Drying; Gas Chromatography-Mass Spectrometry; Microwaves; Monoterpenes; Odorants; Oxides; Polycyclic Sesquiterpenes; Sesquiterpenes; Smell; Terpenes; Volatilization

In the present study, essential oil from the leaves of Syrian oreganum [Origanum syriacum L. (Lauraceae)] grown in Turkish state forests of the Dortyol district, Turkey, was obtained by steam distillation. The chemical composition of oil was analysed by GC and GC-MS, and was found to contain 49.02% monoterpenes, 36.60% oxygenated monoterpenes and 12.59% sesquiterpenes. The major components are as follows: gamma-terpinene, carvacrol, p-cymene and beta-caryophyllene. Subsequently, the reducing power, antioxidant and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activities of the essential oil were studied. The reducing power was compared with ascorbic acid, and the other activities were compared with 2,6-di-tert-butyl-4-methyl phenol (BHT, butylated hydroxytoluene). The results showed that the activities were concentration dependent. The antioxidant activities of the oil were slightly lower than those of ascorbic acid or BHT, so the oil can be considered an effective natural antioxidant. Antimicrobial activities of the essential oil from the leaves of Origanum syriacum was also determined on 16 microorganisms tested using the agar-disc diffusion method, and showed antimicrobial activity against 13 of these.

Topics: Ampicillin; Anti-Infective Agents; Antioxidants; Ascorbic Acid; Biphenyl Compounds; Cyclohexane Monoterpenes; Cymenes; Dose-Response Relationship, Drug; Drug Evaluation, Preclinical; Escherichia coli; Free Radical Scavengers; Klebsiella pneumoniae; Micrococcus luteus; Monoterpenes; Nystatin; Oils, Volatile; Origanum; Picrates; Plant Leaves; Plant Oils; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes; Staphylococcus aureus; Streptomycin; Turkey