humulene and caryophyllene

Plants have been the predominant source of medicines throughout the vast majority of human history, and remain so today outside of industrialized societies. One of the most versatile in terms of its phytochemistry is cannabis, whose investigation has led directly to the discovery of a unique and widespread homeostatic physiological regulator, the endocannabinoid system. While it had been the conventional wisdom until recently that only cannabis harbored active agents affecting the endocannabinoid system, in recent decades the search has widened and identified numerous additional plants whose components stimulate, antagonize, or modulate different aspects of this system. These include common foodstuffs, herbs, spices, and more exotic ingredients: kava, chocolate, black pepper, and many others that are examined in this review.

Topics: Amidohydrolases; Cannabinoids; Cannabis; Endocannabinoids; Humans; Phytotherapy; Plants, Medicinal; Polycyclic Sesquiterpenes; Probiotics; Sesquiterpenes; TRPV Cation Channels

The annual production of hops (Humulus lupulus L.) exceeds 100,000 mt and is almost exclusively consumed by the brewing industry. The value of hops is attributed to their characteristic secondary metabolites; these metabolites are precursors which are transformed during the brewing process into important bittering, aromatising and preservative components with rather low efficiency. By selectively transforming these components off-line, both their utilisation efficiency and functionality can be significantly improved. Therefore, the chemical transformations of these secondary metabolites will be considered with special attention to recent advances in the field. The considered components are the hop alpha-acids, hop beta-acids and xanthohumol, which are components unique to hops, and alpha-humulene and beta-caryophyllene, sesquiterpenes which are highly characteristic of hops.

Topics: Beer; Flavonoids; Humulus; Monocyclic Sesquiterpenes; Oxidation-Reduction; Polycyclic Sesquiterpenes; Propiophenones; Sesquiterpenes

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

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

Hops (Humulus lupulus L.) are a dioecious climbing perennial, with the dried mature "cones" (strobili) of the pistillate/female inflorescences being widely used as both a bittering agent and to enhance the flavour of beer. The glandular trichomes of the bract and bracteole flowering structures of the cones produce an abundance of secondary metabolites, such as terpenoids, bitter acids and prenylated phenolics depending on plant genetics, developmental stage and environment. More knowledge is required on the functional and allelic diversity of terpene synthase (TPS) genes responsible for the biosynthesis of volatile terpenes to assist in flavour-directed hop breeding.. Major volatile terpene compounds were identified using gas chromatography-mass spectrometry (GC-MS) in the ripe cones of twenty-one hop cultivars grown in New Zealand. All cultivars produced the monoterpene β-myrcene and the sesquiterpenes α-humulene and β-caryophyllene, but the quantities varied broadly. Other terpenes were found in large quantities in only a smaller subset of cultivars, e.g. β-farnesene (in seven cultivars) and α-pinene (in four). In four contrasting cultivars (Wakatu™, Wai-iti™, Nelson Sauvin™, and 'Nugget'), terpene production during cone development was investigated in detail, with concentrations of some of the major terpenes increasing up to 1000-fold during development and reaching maximal levels from 50-60 days after flowering. Utilising the published H. lupulus genome, 87 putative full-length and partial terpene synthase genes were identified. Alleles corresponding to seven TPS genes were amplified from ripe cone cDNA from multiple cultivars and subsequently functionally characterised by transient expression in planta. Alleles of the previously characterised HlSTS1 produced humulene/caryophyllene as the major terpenes. HlRLS alleles produced (R)-(-)-linalool, whilst alleles of two sesquiterpene synthase genes, HlAFS1 and HlAFS2 produced α-farnesene. Alleles of HlMTS1, HlMTS2 and HlTPS1 were inactive in all the hop cultivars studied.. Alleles of four TPS genes were identified and shown to produce key aroma volatiles in ripe hop cones. Multiple expressed but inactive TPS alleles were also identified, suggesting that extensive loss-of-function has occurred during domestication and breeding of hops. Our results can be used to develop hop cultivars with novel/improved terpene profiles using marker-assisted breeding strategies to select for, or against, specific TPS alleles.

Topics: Alleles; Humulus; Plant Breeding; Terpenes

The most frequently reported use of medical marijuana is for pain relief. However, its psychoactive component Δ9-tetrahydrocannabinol (THC) causes significant side effects. Cannabidiol (CBD) and β-caryophyllene (BCP), two other cannabis constituents, possess more benign side effect profiles and are also reported to reduce neuropathic and inflammatory pain. We evaluated the analgesic potential of CBD and BCP individually and in combination in a rat spinal cord injury (SCI) clip compression chronic pain model. Individually, both phytocannabinoids produced dose-dependent reduction in tactile and cold hypersensitivity in male and female rats with SCI. When co-administered at fixed ratios based on individual A50s, CBD and BCP produced enhanced dose-dependent reduction in allodynic responses with synergistic effects observed for cold hypersensitivity in both sexes and additive effects for tactile hypersensitivity in males. Antinociceptive effects of both individual and combined treatment were generally less robust in females than males. CBD:BCP co-administration also partially reduced morphine-seeking behavior in a conditioned place preference (CPP) test. Minimal cannabinoidergic side effects were observed with high doses of the combination. The antinociceptive effects of the CBD:BCP co-administration were not altered by either CB2 or μ-opioid receptor antagonist pretreatment but, were nearly completely blocked by CB1 antagonist AM251. Since neither CBD or BCP are thought to mediate antinociception via CB1 activity, these findings suggest a novel CB1 interactive mechanism between these two phytocannabinoids in the SCI pain state. Together, these findings suggest that CBD:BCP co-administration may provide a safe and effective treatment option for the management of chronic SCI pain.

Topics: Analgesics; Animals; Cannabidiol; Cannabinoid Receptor Agonists; Cannabis; Chronic Pain; Dronabinol; Female; Hallucinogens; Male; Rats; Spinal Cord Injuries

In recent years, there has been increased accessibility to cannabis for recreational and medicinal use. Incidentally, there has been an increase in reports describing allergic reactions to cannabis including exacerbation of underlying asthma. Recently, multiple protein allergens were discovered in cannabis, yet these fail to explain allergic sensitization in many patients, particularly urticaria and angioedema. Cannabis has a rich chemical profile including cannabinoids and terpenes that possess immunomodulatory potential. We examined whether major cannabinoids of cannabis such as cannabidiol (CBD) and the bicyclic sesquiterpene beta-caryophyllene (β-CP) act as contact sensitizers. The repeated topical application of mice skin with β-CP at 10 mg/mL (50 µL) induced an itch response and dermatitis at 2 weeks in mice, which were sustained for the period of study. Histopathological analysis of skin tissues revealed significant edema and desquamation for β-CP at 10 mg/mL. For CBD and β-CP, we observed a dose-dependent increase in epidermal thickening with profound thickening observed for β-CP at 10 mg/mL. Significant trafficking of CD11b cells was observed in various compartments of the skin in response to treatment with β-CP in a concentration-dependent manner. Mast cell trafficking was restricted to β-CP (10 mg/mL). Mouse proteome profiler cytokine/chemokine array revealed upregulation of complement C5/5a (anaphylatoxin), soluble intracellular adhesion molecule-1 (sICAM-1) and IL-1 receptor antagonist (IL-1RA) in animals dosed with β-CP (10 mg/mL). Moreover, we observed a dose-dependent increase in serum IgE in animals dosed with β-CP. Treatment with β-CP (10 mg/mL) significantly reduced filaggrin expression, an indicator of barrier disruption. In contrast, treatment with CBD at all concentrations failed to evoke scratching and dermatitis in mice and did not result in increased serum IgE. Further, skin tissues were devoid of any remarkable features, although at 10 mg/mL CBD we did observe the accumulation of dermal CD11b cells in skin tissue sections. We also observed increased filaggrin staining in mice repeatedly dosed with CBD (10 mg/mL). Collectively, our studies indicate that repeated exposure to high concentrations of β-CP can induce dermatitis-like pathological outcomes in mice.

Topics: Angioedema; Animals; Cannabidiol; Cannabinoid Receptor Agonists; Cannabis; Complement C5; Complement C5a; Dermatitis; Filaggrin Proteins; Hallucinogens; Humans; Immunoglobulin E; Inflammation; Mice; Pruritus

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

Cannabis contains over 500 distinct compounds, which include cannabinoids, terpenoids, and flavonoids. However, very few of these compounds have been studied for their beneficial effects. There is an emerging concept that the constituents of the cannabis plant may work in concert to achieve better therapeutic benefits. This study is aimed at determining if the combination of a minor cannabinoid (cannabidiol, CBD) and a terpene (beta-caryophyllene, BCP) works in concert and if this has any therapeutic value. We used an inflammatory pain model (formalin) in mice to test for any functionality of CBD and BCP in combination. First, we determined the analgesic effect of CBD and BCP individually by establishing dose-response studies. Second, we tested the analgesic effect of fixed-ratio combinations and monitored any adverse effects. Finally, we determined the effect of this combination on inflammation. The combination of CBD and BCP produces a synergistic analgesic effect. This effect was without the cannabinoid receptor-1 side effects. The analgesic effect of CBD and BCP in combination involves an inflammatory mechanism. The combination of these two constituents of the cannabis plant, CBD and BCP, works in concert to produce a therapeutic effect with safety profiles through an inflammatory mechanism.

Topics: Analgesics; Animals; Cannabidiol; Cannabinoids; Cannabis; Dronabinol; Drug-Related Side Effects and Adverse Reactions; Mice; Polycyclic Sesquiterpenes; Terpenes

The chemical composition of the essential oil of

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

It is well known that duration of pre-drying storage impacts on hop quality. However, little knowledge exists regarding its actual effects on valuable hop components. To investigate these effects, fresh hop cones were stored for 5 or 24 h and dried for 210 min at 65 °C thereafter. Furthermore, to understand the effect of freezing hop cones on the essential oil content, both fresh and stored samples were frozen before and after drying.. The results from gas chromatography analysis show an increase in linalool, β-caryophyllene, humulene, geraniol content and decrease in myrcene content dependent on the period of storage. Total colour difference ΔE values of 4.61 and 5.27 were obtained for fresh and stored hops respectively, indicating discoloration of hops during storage. Modelling of moisture curves revealed the Wang and Singh model to be suitable, with. The results from this study provide an in-depth understanding on the changes occurring within the hop cones both during storage and drying and will further help hop processors optimize their storage times.

Topics: Acyclic Monoterpenes; Alkenes; Chromatography, Gas; Desiccation; Food Handling; Hot Temperature; Humulus; Monocyclic Sesquiterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Time Factors

Secondary metabolites produced in glandular trichomes of tomato are involved in interactions with herbivores. In cultivated tomato (Solanum lycopersicum) glandular trichomes accumulate a blend of abundant monoterpenes and smaller amounts of a few sesquiterpenes. These mono- and sesquiterpenes are synthesized by three terpene synthases, TPS20 as well as TPS9 and TPS12, respectively. To study effects of these terpenes on performance and choice behavior of potato aphid (Macrosiphum euphorbiae), we utilized two tomato trichome mutants, hairless and odorless-2, that are differently affected in mono- and sesquiterpene production. Non-choice assays demonstrated that longevity and fecundity of M. euphorbiae were increased when kept on the trichome mutants. A principal component analysis of these aphid performance parameters and terpene production in the trichome mutants indicated that longevity and fecundity of M. euphorbiae were negatively correlated with production of the TPS12-derived sesquiterpenes β-caryophyllene and α-humulene. While we had previously shown that addition of pure β-caryophyllene/α-humulene to an artificial feeding diet affected M. euphorbiae apterae survivorship and feeding behavior, no such effects were observed here upon addition of a mixture of pure TPS20-derived monoterpenes. In olfactometer assays M. euphorbiae alates displayed differential choice behaviors towards the hairless and odorless-2 mutants suggesting a role of TPS20-derived monoterpenes in aphid attraction, which was further confirmed using a mixture of pure monoterpenes. Our analyses revealed contrasting roles of glandular trichome-derived terpenes in S. lycopersicum. While TPS12-derived sesquiterpenes contribute to host plant resistance against M. euphorbiae, TPS20-derived monoterpenes appear to be exploited as cue for host plant orientation by aphids.

Topics: Animals; Aphids; Fertility; Longevity; Monocyclic Sesquiterpenes; Monoterpenes; Olfactometry; Polycyclic Sesquiterpenes; Solanum lycopersicum; Trichomes

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

Compounds having insecticidal activity can be used to control Aedes aegypti mosquitoes, a major worldwide vector, and several plants have a source of such molecules. A principal component analysis (PCA) was carried out to determine the criterion to select larvicidal metabolites. The insecticidal activity of seven selected metabolites by PCA was validated by determining its lethal concentrations 50 (LC

Topics: Acetates; Acyclic Monoterpenes; Aedes; Animals; Insecticides; Mitochondria; Monocyclic Sesquiterpenes; Mosquito Control; Oxidation-Reduction; Polycyclic Sesquiterpenes; Secondary Metabolism

Ageratum conyzoides is an aromatic plant. It is considered as an invasive and cosmopolite weed, widely spread in tropical and subtropical regions. Phytochemicals such as benzopyrenes, flavonoids, and terpenoids are reported from A. conyzoides.. Development and validation of a reversed-phase HPLC-photodiode array (PDA) detection method for simultaneous identification and quantification of coumarin, precocene-I, β-caryophyllene oxide, α-humulene, and β-caryophyllene in extracts of A. conyzoides and essential oils was carried out.. Separation of analytes was achieved on a RP-18 (250 mm × 4.6 mm, 5 µm) column using a solvent system comprising of a mixture of acetonitrile and water with 0.05% trifluoroacetic acid in gradient elution mode at ambient temperature with flow rate of 1 mL/min.. The retention time of coumarin, precocene-I, β-caryophyllene oxide, α-humulene, and β-caryophyllene was 4.38, 12.86, 20.10, 33.34, and 35.11 min, respectively. Limits of detection for coumarin, precocene-I, β-caryophyllene oxide, α-humulene, and β-caryophyllene were 2.5, 2.5, 2.5, 0.025, and 2.5 µg/mL, respectively. Similarly, LOQ were 10, 10, 10, 0.10, and 10 µg/mL for coumarin, precocene-I, β-caryophyllene oxide, α-humulene, and β- caryophyllene, respectively. Repeatabilities (RSD, %) values for intraday and interday precision for coumarin, precocene-I, β-caryophyllene oxide, α-humulene, and β-caryophyllene was 0.765-2.086 and 0.886-2.128; 0.879-1.672 and 0.979-1.825; 0.696-2.418 and 0.768-2.592; 1.728-2.362 and 1.965-2.378; 1.615-2.897 and 1.658-2.906, respectively.. The separation of five analytes was achieved within 50 min. The developed and validated HPLC-PDA method was successfully applied for identification and quantification of above five analytes in A. conyzoides extracts and essential oils. The method could be used for meeting the characterization criteria of phytoformulations.

Topics: Ageratum; Chromatography, High Pressure Liquid; Coumarins; Monocyclic Sesquiterpenes; Oils, Volatile; Plant Extracts; Polycyclic Sesquiterpenes

The hydro-distilled essential oil from aerial parts of

Topics: Bicyclic Monoterpenes; Cyclohexane Monoterpenes; Gas Chromatography-Mass Spectrometry; Lamiaceae; Monocyclic Sesquiterpenes; Oils, Volatile; Orthosiphon; Polycyclic Sesquiterpenes; Sesquiterpenes

The effect of exogenous application of jasmonic acid (JA) on the concentration of main terpenes and density of glandular trichomes was investigated in the Mexican oregano, propagated from seeds from 3 localities. JA 1 mM was applied locally and to the whole plant. JA locally applied increased the number of trichomes, with a mean of 20 trichomes more with respect to the controls in plants from Tecomavaca and Zapotitlán Salinas, and significantly increased the thymol concentration by 185% systemically and 255% locally, compared to the control. JA applied to the whole plant decreased the number of trichomes and increased the concentration of caryophyllene from 0.79 to 1.7 mg g

Topics: Cyclopentanes; Lippia; Mexico; Monocyclic Sesquiterpenes; Monoterpenes; Origanum; Oxylipins; Polycyclic Sesquiterpenes; Terpenes; Thymol; Trichomes; Verbenaceae

The investigation of the stem essential oil of

Topics: Asteraceae; Cote d'Ivoire; Cyclohexane Monoterpenes; Cymenes; Epoxy Compounds; Gas Chromatography-Mass Spectrometry; Magnetic Resonance Spectroscopy; Molecular Structure; Monocyclic Sesquiterpenes; Oils, Volatile; Plant Stems; Polycyclic Sesquiterpenes; Sesquiterpenes, Eudesmane; Stereoisomerism

Sesquiterpenes, the main components of plant essential oils, are bioactive compounds with numerous health-beneficial activities. Sesquiterpenes can interact with concomitantly administered drugs due to the modulation of drug-metabolizing enzymes (DMEs). The aim of this study was to evaluate the modulatory effects of six sesquiterpenes (farnesol,

Topics: Aged; Aged, 80 and over; Aldo-Keto Reductases; Carbonyl Reductase (NADPH); Cytochrome P-450 CYP3A; Cytochrome P-450 Enzyme System; Cytochrome P450 Family 2; Farnesol; Female; Hep G2 Cells; Hepatocytes; Humans; Liver; Male; Metabolic Clearance Rate; Middle Aged; Monocyclic Sesquiterpenes; Polycyclic Sesquiterpenes; Pregnane X Receptor; Receptors, Aryl Hydrocarbon; RNA, Messenger; Sesquiterpenes

The process of urbanization of natural environments has dramatically increased the incidence of pest insects. To control these organisms in urban environments, the last decades have been marked by an increase in the use of synthetic insecticides. However, the intensive and indiscriminate use of synthetic insecticides has provoked a series of environmental problems and human health. In this way, the concern and the searching for environmentally safer alternatives for the control of urban pests is increasing. In the present study we evaluated the lethal and sublethal effects of essential oils (EOs) of six accessions of Varronia curassavica (Jacq.) (Cordiaceae) and their constituents (E)-caryophyllene and α-humulene on the ant Dorymyrmex thoracicus Gallardo, 1916 (Formicidae: Dolichoderinae), a species commonly found in urban environments and which can cause damage to human health. Bioassays of fumigation toxicity and locomotor activity in partially treated arenas were performed. The lethal concentrations to kill 50% of the D. thoracicus population ranged from 0.69 to 2.48 μL/L for EOs and from 3.75 to 1.49 μL/L for the (E)-caryophyllene and α-humulene compounds. The survival of the ants exposed to LC

Topics: Animals; Ants; Insect Repellents; Insecticides; Monocyclic Sesquiterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes

Volatile terpenes represent the largest group of

Topics: Acyclic Monoterpenes; Anti-Bacterial Agents; Bacteria; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cannabinoids; Cannabis; Gas Chromatography-Mass Spectrometry; Microbial Sensitivity Tests; Monoterpenes; Oils, Volatile; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes

The profile and bioactivity of hops (Humulus lupulus L.) essential oil, a complex natural product extracted from cones via steam distillation, depends on genetic and environmental factors, and may also depend on extraction process. We hypothesized that compound mixtures eluted sequentially and captured at different timeframes during the steam distillation process of whole hop cones would have differential chemical and bioactivity profiles. The essential oil was collected sequentially at 8 distillation time (DT) intervals: 0-2, 2-5, 5-10, 10-30, 30-60, 60-120, 120-180, and 180-240 min. The control was a 4-h non-interrupted distillation. Nonlinear regression models described the DT and essential oil compounds relationship. Fractions yielded 0.035 to 0.313% essential oil, while control yielded 1.47%. The oil eluted during the first hour was 83.2%, 9.6% during the second hour, and only 7.2% during the second half of the distillation. Essential oil (EO) fractions had different chemical profile. Monoterpenes were eluted early, while sequiterpenes were eluted late. Myrcene and linalool were the highest in 0-2 min fraction, β-caryophyllene, β-copaene, β-farnesene, and α-humulene were highest in fractions from middle of distillation, whereas α- bergamotene, γ-muurolene, β- and α-selinene, γ- and δ-cadinene, caryophyllene oxide, humulne epoxide II, τ-cadinol, and 6-pentadecen-2-one were highest in 120-180 or 180-240 min fractions. The Gram-negative Escherichia coli was strongly inhibited by essential oil fractions from 2-5 min and 10-30 min, followed by oil fraction from 0-2 min. The strongest inhibition activity against Gram-negative Yersinia enterocolitica, and Gram-positive Clostridium perfringens, Enterococcus faecalis, and Staphylococcus aureus subs. aureus was observed with the control essential oil. This is the first study to describe significant activity of hops essential oils against Trypanosoma brucei, a parasitic protozoan that causes African trypanosomiasis (sleeping sickness in humans and nagana in other animals). Hops essential oil fractions or whole oil may be used as antimicrobial agents or for the development of new drugs.

Topics: Acyclic Monoterpenes; Alkenes; Antiprotozoal Agents; Bridged Bicyclo Compounds; Clostridium perfringens; Distillation; Drug Resistance, Bacterial; Enterococcus faecalis; Escherichia coli; Humulus; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes; Staphylococcus aureus; Steam; Trypanosoma brucei brucei; Yersinia enterocolitica

Topics: Aedes; Animals; Anopheles; Biological Control Agents; Culex; Female; Insecticides; Larva; Monocyclic Sesquiterpenes; Mosquito Vectors; Myrtaceae; Oils, Volatile; Oviposition; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Syzygium

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

The main challenge in schistosomiasis control has been the emergence of drug-resistant parasites. Since the 1970's, praziquantel (PZQ) is the single drug for treatment. This fact highlights the importance to research news chemotherapeutic agents. In the last years, S. mansoni excretory system and tegument have been major targets for drug development. The purpose of this study was to evaluate the effect of sesquiterpenes, alpha-humulene and trans-caryophyllene on S. mansoni survival, excretory system and membrane integrity, after in vitro exposure. The in vitro studies, showed that sesquiterpenes reduced egg production and motor activity of worms at sublethal concentrations, and caused death in a concentration-dependent manner (100 and 200μg/mL). Tegumental analysis by Scanning Electron Microscopy (SEM), showed tegument damage. Additionally, it was possible to observe lesions, evidenced by intense marking trough Hoechst probe, in the tegument and suckers of worms exposed to 200μg/mL. In this study, we also showed that resorufin is only capable of identifying the interaction of sesquiterpenes in males excretory system, Pgp expression and inferring that females are more tolerant to treatments. Thus, the present study results contribute to an understanding of alpha-humulene and trans-caryophyllene effect over these targets, contributing for the development of schistosomicidal drugs.

Topics: Animals; Female; Male; Membranes; Microscopy, Electron, Scanning; Monocyclic Sesquiterpenes; Oxazines; Polycyclic Sesquiterpenes; Schistosoma mansoni; Schistosomiasis mansoni; Schistosomicides; Sesquiterpenes

Chemical composition and biological (antimicrobial, antioxidant and cytotoxic) activities of essential oils (EO) obtained from the aerial parts of Glycyrrhiza triphylla Fisch. & C.A.Mey (G. triphylla) were evaluated in the present study. The EO was isolated and analyzed using gas chromatography-mass spectrometry (GC-MS). Fifty-five compounds representing 99.3% of the total oil composition were identified. Major components of the oil were β-caryophyllene (25.4%), limonene (16.7%), β-myrcene (16.0%) and α-humulene (4.4%). The oil composition was dominated by the presence of sesquiterpene hydrocarbons comprising 43.6% of the total oil. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of the oil were determined against eight bacterial strains and one fungus. The EO showed a good antibacterial activity against both Gram-positive and Gram-negative bacteria. The most susceptible strain was Micrococcus luteus (MIC = 2.7 μg/mL, MBC = 43.6 μg/mL). The antioxidant potential of the EO was examined using DPPH and β-carotene/linoleic acid (BCB) assays. The oil was considerably active in the DPPH assay (IC

Topics: Acyclic Monoterpenes; Animals; Anti-Bacterial Agents; Anti-Infective Agents; Antifungal Agents; Antioxidants; Bacteria; beta Carotene; Cell Line; Cell Survival; Cyclohexenes; Fungi; Gas Chromatography-Mass Spectrometry; Glycyrrhiza; Humans; Iran; Limonene; Mice; Microbial Sensitivity Tests; Monocyclic Sesquiterpenes; Monoterpenes; NIH 3T3 Cells; Oils, Volatile; Plant Extracts; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes

Sesquiterpenes, the main components of plant essential oils, are often taken in the form of folk medicines and dietary supplements. Several sesquiterpenes possess interesting biological activities but they could interact with concurrently administered drugs via inhibition of drug-metabolizing enzymes. Therefore, the present study was designed to test the potential inhibitory effect of tree structurally relative sesquiterpenes β-caryophyllene (CAR), β-caryophyllene oxide (CAO) and α-humulene (HUM) on the activities of the main drug-metabolizing enzymes. For this purpose, rat and human hepatic subcellular fractions were incubated with CAR, CAO or HUM together with specific substrates for oxidation, reduction and conjugation enzymes and their coenzymes. HPLC, spectrophotometric and spectrofluorimetric analyses of product formations were used. All tested sesquiterpenes significantly inhibited cytochromes P4503A (CYP3A) activities in rats as well as in human hepatic microsomes, with CAO being the strongest inhibitor. A non-competitive type of inhibition was found. On the other hand, none of the tested sesquiterpenes significantly affected the activities of carbonyl-reducing enzymes (CBR1, AKRs, NQO1) or conjugation enzymes (UGTs, GSTs, SULTs, COMT). As CYP3A enzymes metabolize many drugs, their inhibition by CAO, CAR and HUM might affect the pharmacokinetics of concurrently administered drugs. Similar results obtained in rat and human hepatic microsomes indicate that rats could be used for further testing of possible drug-sesquiterpenes interactions in vivo.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Cytochrome P-450 CYP1A2; Cytochrome P-450 CYP3A; Humans; Inhibitory Concentration 50; Kinetics; Liver; Male; Microsomes, Liver; Monocyclic Sesquiterpenes; Polycyclic Sesquiterpenes; Rats; Rats, Wistar; Sesquiterpenes

The antifungal effects of four essential oils viz., clove (Syzygium aromaticum), lemongrass (Cymbopogon citratus), mint (Mentha × piperita) and eucalyptus (Eucalyptus globulus) were evaluated against wilt causing fungus, Fusarium oxysporum f. sp. lycopersici 1322. The inhibitory effect of oils showed dose-dependent activity on the tested fungus. Most active being the clove oil, exhibiting complete inhibition of mycelial growth and spore germination at 125 ppm with IC

Topics: Antifungal Agents; Cymbopogon; Eucalyptus; Eugenol; Fusarium; Inhibitory Concentration 50; Mentha; Microbial Sensitivity Tests; Monocyclic Sesquiterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Solanum lycopersicum; Syzygium

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

Mosquitoes (Diptera: Culicidae) are important vectors of terms of public health relevance, especially in tropical and sub-tropical regions. The continuous and indiscriminate use of conventional pesticides for the control of mosquito vectors has resulted in the development of resistance and negative impacts on non-target organisms and the environment. Therefore, there is a need for development of effective mosquito control tools. In this study, the larvicidal and repellent activity of Zingiber nimmonii rhizome essential oil (EO) was evaluated against the malaria vector Anopheles stephensi, the dengue vector Aedes aegypti, and the lymphatic filariasis vector Culex quinquefasciatus. The chemical composition of the EO was analyzed by gas chromatography-mass spectroscopy (GC-MS). GC-MS revealed that the Z. nimmonii EO contained at least 33 compounds. Major constituents were myrcene, β-caryophyllene, α-humulene, and α-cadinol. In acute toxicity assays, the EO showed significant toxicity against early third-stage larvae of An. stephensi, Ae. aegypti, and Cx. quinquefasciatus, with LC50 values of 41.19, 44.46, and 48.26 μg/ml, respectively. Repellency bioassays at 1.0, 2.0, and 5.0 mg/cm(2) of Z. nimmonii EO gave 100 % protection up to 120, 150, and 180 min. against An. stephensi, followed by Ae. aegypti (90, 120, and 150 min) and Cx. quinquefasciatus (60, 90, and 120 min). Furthermore, the EO was safer towards two non-target aquatic organisms, Diplonychus indicus and Gambusia affinis, with LC50 values of 3241.53 and 9250.12 μg/ml, respectively. Overall, this research adds basic knowledge to develop newer and safer natural larvicides and repellent from Zingiberaceae plants against malaria, dengue, and filariasis mosquito vectors.

Topics: Acyclic Monoterpenes; Aedes; Alkenes; Animals; Anopheles; Culex; Dengue; Elephantiasis, Filarial; Gas Chromatography-Mass Spectrometry; Insect Repellents; Insecticides; Larva; Malaria; Monocyclic Sesquiterpenes; Monoterpenes; Mosquito Control; Mosquito Vectors; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Zingiberaceae

The formation of highly oxidized multifunctional organic compounds (HOMs) from the ozonolysis of three sesquiterpenes, α-cedrene, β-caryophyllene, and α-humulene, was investigated for the first time. Sesquiterpenes contribute 2.4% to the global carbon emission of biogenic volatile organic compounds (BVOCs) and can be responsible for up to 70% of the regional BVOC emissions. HOMs were detected with chemical ionization-atmospheric pressure interface-time-of-flight mass spectrometry and nitrate and acetate ionization. Acetate ions were more sensitive toward highly oxidized RO2 radicals containing a single hydroperoxide moiety. Under the chosen reaction conditions, product formation was dominated by highly oxidized RO2 radicals which react with NO, NO2, HO2, and other RO2 radicals under atmospheric conditions. The ozonolysis of sesquiterpenes resulted in molar HOM yields of 0.6% for α-cedrene (acetate), 1.8% for β-caryophyllene (acetate), and 1.4% for α-humulene (nitrate) afflicted with an uncertainty factor of 2. Molar yields of highly oxidized RO2 radicals were identical with HOM yields measuring the corresponding closed-shell products. HOM formation from ozonolysis of α-cedrene was explained by an autoxidation mechanism initiated by ozone attack at the double bond similar to that found in the ozonolysis of cyclohexene and limonene.

Topics: Acetates; Atmosphere; Free Radicals; Ions; Mass Spectrometry; Monocyclic Sesquiterpenes; Nitrates; Oxidation-Reduction; Oxygen; Ozone; Polycyclic Sesquiterpenes; Sesquiterpenes; Volatile Organic Compounds

Absorption of hop volatiles by crown cork liner polymers and can coatings was investigated in beer during storage. All hop volatiles measured were prone to migrate into the closures, and the absorption kinetics was demonstrated to fit Fick's second law of diffusion well for a plane sheet. The extent and rate of diffusion were significantly dissimilar and were greatly dependent upon the nature of the volatile. Diffusion coefficients ranged from 1.32 × 10(-5) cm(2)/day (limonene) to 0.26 × 10(-5) cm(2)/day (α-humulene). The maximum amounts absorbed into the material at equilibrium were in the following order: limonene > α-humulene > trans-caryophyllene > myrcene ≫ linalool > α-terpineol > geraniol. With the application of low-density polyethylene (LDPE) liners with oxygen-scavenging functionality, oxygen-barrier liners made up from high-density polyethylene (HDPE) or liner polymers from a different manufacturer had no significant effect on the composition of hop volatiles in beers after prolonged storage of 55 days; however, significantly higher amounts of myrcene and limonene were found in the oxygen-barrier-type crown cork, while all other closures behaved similarly. Can coatings were demonstrated to absorb hop volatiles in a similar pattern as crown corks but to a lesser extent. Consequently, significantly higher percentages of myrcene were found in the beers.

Topics: Acyclic Monoterpenes; Alkenes; Beer; Cyclohexane Monoterpenes; Cyclohexenes; Gas Chromatography-Mass Spectrometry; Humulus; Limonene; Monocyclic Sesquiterpenes; Monoterpenes; Polycyclic Sesquiterpenes; Polyethylene; Polymers; Sesquiterpenes; Terpenes

The genus Ocimum has a unique blend of diverse secondary metabolites, with major proportion of terpenoids including mono- and sesquiterpenes. Although, β-Caryophyllene, bicyclic sesquiterpene, is one of the major terpene found in Ocimum species and known to possess several biological activities, not much is known about its biosynthesis in Ocimum. Here, we describe isolation and characterization of β-caryophyllene synthase gene from Ocimum kilimandscharicum Gürke (OkBCS- GenBank accession no. KP226502). The open reading frame of 1629 bp encoded a protein of 542 amino acids with molecular mass of 63.6 kDa and pI value of 5.66. The deduced amino acid sequence revealed 50-70% similarity with known sesquiterpene synthases from angiosperms. Recombinant OkBCS converted farnesyl diphosphate to β-caryophyllene as a major product (94%) and 6% α-humulene. Expression variation of OkBCS well corroborated with β-caryophyllene levels in different tissues from five Ocimum species. OkBCS transcript revealed higher expression in leaves and flowers. Further, agro-infiltration based transient expression manipulation with OkBCS over-expression and silencing confirmed its role in β-caryophyllene biosynthesis. These findings may potentially be further utilized to improve plant defense against insect pests.

Topics: Agrobacterium; Alkyl and Aryl Transferases; Amino Acid Sequence; Gas Chromatography-Mass Spectrometry; Gene Expression Regulation; Gene Silencing; Magnoliopsida; Molecular Sequence Data; Monocyclic Sesquiterpenes; Ocimum; Open Reading Frames; Phylogeny; Plant Leaves; Plant Proteins; Polycyclic Sesquiterpenes; Polyisoprenyl Phosphates; Recombinant Proteins; Sequence Homology, Amino Acid; Sesquiterpenes

E-(β)-caryophyllene is a sesquiterpene volatile emitted by plants and involved in many ecological interactions within and among trophic levels and it has a kairomonal activity for many insect species. In grapevine it is a key compound for host-plant recognition by the European grapevine moth, Lobesia botrana, together with other two sesquiterpenes. In grapevine E-(β)-caryophyllene synthase is coded by the VvGwECar2 gene, although complete characterization of the corresponding protein has not yet been achieved. Here we performed the characterization of the enzyme after heterologous expression in E. coli, which resulted to produce in vitro also minor amounts of the isomer α-humulene and of germacrene D. The pH optimum was estimated to be 7.8, and the K

Topics: Alkyl and Aryl Transferases; Arabidopsis; Escherichia coli; Monocyclic Sesquiterpenes; Polycyclic Sesquiterpenes; Polyisoprenyl Phosphates; Sesquiterpenes; Stereoisomerism; Vitis; Volatile Organic Compounds

The composition of essential oil isolated from Senecio nudicaulis Wall. ex DC. growing wild in Himachal Pradesh, India, was analysed, for the first time, by capillary gas chromatography (GC) and GC-mass spectrometry. A total of 30 components representing 95.3% of the total oil were identified. The essential oil was characterised by a high content of oxygenated sesquiterpenes (54.97%) with caryophyllene oxide (24.99%) as the major component. Other significant constituents were humulene epoxide-II (21.25%), α-humulene (18.75%), β-caryophyllene (9.67%), epi-α-cadinol (2.90%), epi-α-muurolol (2.03%), β-cedrene (1.76%), longiborneol (1.76%), 1-tridecene (1.16%) and citronellol (1.13%). The oil was screened for antioxidant activity using DPPH, ABTS and nitric oxide-scavenging assay. The oil was found to exhibit significant antioxidant activity by scavenging DPPH, ABTS and nitric oxide radicals with IC50 values of 10.61 ± 0.14 μg mL(- 1), 11.85 ± 0.28 μg mL(- 1) and 11.29 ± 0.42 μg mL(- 1), respectively.

Topics: Acyclic Monoterpenes; Alkenes; Antioxidants; Gas Chromatography-Mass Spectrometry; India; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Oils; Plants, Medicinal; Polycyclic Sesquiterpenes; Senecio; Sesquiterpenes; Terpenes

The objectives of this study were to chemically characterise and evaluate the antioxidant potential of the essential oil from Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia. The volatile oil was extracted by hydrodistillation of the aerial parts in a Clevenger type apparatus. Forty constituents were identified via GC and GC-MS analysis. β-caryophyllene (32.5%) and α-humulene (17.8%) were the most abundant components. The evaluation of free radical scavenging activity using stable DPPH free radical showed that the volatile oil exhibits a moderate antioxidant activity and reduces DPPH to 50% at EC50 value of 1230 μg mL(-1).

Topics: Antioxidants; Gas Chromatography-Mass Spectrometry; Molecular Structure; Monocyclic Sesquiterpenes; Oils, Volatile; Plant Components, Aerial; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Teucrium; Tunisia

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

The stabilizing features of a macrocyclic sesquiterpene-derived cation were explored using quantum mechanical calculations. The monocyclic humulyl cation, the product of 11,1-cyclization of farnesyl diphosphate, is the product of the first committed step in the enzymatic synthesis of a range of structurally diverse sesquiterpenes, including humulene (monocyclic); caryophyllene (bicyclic); and protoilludene, pentalenene, and isocomene (tricyclic). These natural products are formed via carbocation cascades that are directed in part by the conformation of the humulyl cation. Understanding the mechanistic details of product formation requires an understanding of the conformational preferences of this fundamental intermediate. Replacing the carbocation with borane (preserving π-accepting capabilities), ammonium (preserving positive charge), and methylene (preserving neither π-accepting capabilities nor charge) provides a systematic method to distinguish electrostatic and orbital effects on structure and internal stabilization. Several modes of internal stabilization—hyperconjugation, transannular π(alkene)···C(+) and transannular C-H···C(+) interactions—were uncovered, confirming and extending previous studies on this and similar systems.

Topics: Cations; Cyclization; Electrons; Hydrogen Bonding; Macrocyclic Compounds; Molecular Conformation; Monocyclic Sesquiterpenes; Polycyclic Sesquiterpenes; Polyisoprenyl Phosphates; Quantum Theory; Sesquiterpenes; Stereoisomerism

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

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

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

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

The present study focuses on the volatile compounds with characteristic odor of essential oil from the leaves of Magnolia obovata by hydrodistillation (HD) and solvent-assisted flavor evaporation (SAFE) method. Eighty-seven compounds, representing 98.0% of the total oil, were identified using HD. The major compounds of HD oil were (E)-β-caryophyllene (23.7%), α-humulene (11.6%), geraniol (9.1%), and borneol (7.0%). In SAFE oil, fifty-eight compounds, representing 99.7% of the total oil, were identified. The main compounds of SAFE oil were (E)-β-caryophyllene (48.9%), α-humulene (15.7%), and bicyclogermacrene (4.2%). In this study, we newly identified eighty-five compounds of the oils from M. obovata leaves. These oils were also subjected to aroma evaluation by gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA). As a result, twenty-four (HD) and twenty-five (SAFE) aroma-active compounds were detected. (E)-β-Caryophyllene, α-humulene, linalool, geraniol, 1,8-cineole, and bicyclogermacrene were found to impart the characteristic odor of M. obovata leaves. These results imply that the oils of M. obovata leaves must be investigated further to clarify their potential application in the food and pharmaceutical industries.

Topics: Acyclic Monoterpenes; Camphanes; Chromatography, Gas; Cyclohexanols; Distillation; Eucalyptol; Magnolia; Monocyclic Sesquiterpenes; Monoterpenes; Odorants; Oils, Volatile; Olfactometry; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Solvents; Terpenes; Volatilization; Water

To analyze the volatile oil in Piper hongkongense from five different habitats.. The volatile oil was analyzed by GC-MS.. The volatile components oil of each sample varied significantly. Caryophyllene, α-caryophyllene and nerolidol 2 were common constituents of five samples. The volatile oil and chemical constituent contents of fresh sample were higher than that of the old sample.. The volatile oil and chemical constituent contents of Piper hongkongense from different habitats have sig- nificant differences, which are affected by habitats, harvest season, storage time and so on.

Topics: Ecosystem; Gas Chromatography-Mass Spectrometry; Monocyclic Sesquiterpenes; Oils, Volatile; Piper; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes

Aedes aegypti is responsible for the transmission of dengue, a disease that infects millions of people each year. Although essential oils are well recognized as sources of compounds with repellent and larvicidal activities against the dengue mosquito, much less is known about their oviposition deterrent effects. Commiphora leptophloeos, a tree native to South America, has important pharmacological properties, but the chemical profile and applicability of its essential oil in controlling the spread of the dengue mosquito have not been investigated. The aim of this study was to determine the composition of C. leptophloeos leaf oil and to evaluate its larvicidal and oviposition deterrent effects against A. aegypti. Fifty-five components of the essential oil were detected by gas chromatography (GC)-mass spectrometry, with α-phellandrene (26.3%), (E)-caryophyllene (18.0%) and β-phellandrene (12.9%) identified as the major constituents. Bioassays showed that the oil exhibited strong oviposition deterrent effects against A. aegypti at concentrations between 25 and 100 ppm, and possessed good larvicidal activity (LC50 = 99.4 ppm). Analysis of the oil by GC coupled with electroantennographic detection established that seven constituents could trigger antennal depolarization in A. aegypti gravid females. Two of these components, namely (E)-caryophyllene and α-humulene, were present in substantial proportions in the oil, and oviposition deterrence assays confirmed that both were significantly active at concentrations equivalent to those present in the oil. It is concluded that these sesquiterpenes are responsible, at least in part, for the deterrent effect of the oil. The oviposition deterrent activity of the leaf oil of C. leptophloeos is one of the most potent reported so far, suggesting that it could represent an interesting alternative to synthetic insecticides. The results of this study highlight the importance of integrating chemical and electrophysiological methods for screening natural compounds for their potential in combating vectors of insect-borne diseases.

Topics: Aedes; Animals; Anti-Inflammatory Agents, Non-Steroidal; Commiphora; Electrophysiology; Female; Gas Chromatography-Mass Spectrometry; Monocyclic Sesquiterpenes; Oils, Volatile; Oviposition; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes

This study evaluated ultrasound-assisted supercritical carbon dioxide (USC-CO2) extraction for determining the extraction yields of oils and the contents of eugenol, β-caryophyllene, eugenyl acetate and α-humulene from clove buds. Compared to traditional SC-CO2 extraction, USC-CO2 extraction might provide a 13.5% increase in the extraction yield for the oil while utilizing less severe operating parameters, such as temperature, pressure, CO2 flow rate and the time consumed by the process. Our results were comparable to those obtained using the heat reflux extraction method, though the yield was improved by 20.8% using USC-CO2. In kinetic studies, the USC-CO2 extraction of clove oil followed second-order kinetics. The activation energy for the oil extraction was 76.56kJ/mol. The USC-CO2 procedure facilitated the use of mild extraction conditions, improved extraction efficiency and the quality of products and is a potential method for industry.

Topics: Carbon Dioxide; Chemical Fractionation; Eugenol; Flowers; Kinetics; Monocyclic Sesquiterpenes; Particle Size; Plant Oils; Polycyclic Sesquiterpenes; Pressure; Sesquiterpenes; Solvents; Syzygium; Temperature; Time Factors; Ultrasonics

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

Perilla is the genus of herbaceous plants of Lamiaceae family. The essential oil of Perilla is believed to be essential part of the herb. It was claimed to have anti-inflammatory, anti-hyperlipidemia, antioxidative and antimicrobial activities. Apart from pharmaceutical and nutrition purposes, It is an edible plant frequently used as a fresh vegetable. It was also applied to produce perfume and cosmetics. Due to the importance of the essential oil from the P. nanakinensis and the lack of detailed studies of them, our work aimed investigation of contents of essential compositions by GC- TOF/MS method. The materials of the study were the aerial parts of P. nankinesis collected at full flowering stage, Guria Region, Georgia. A qualitative analysis of the individual compounds in P. nankinensis essential oil performed by gas chromatography (GC) coupled with time-of-flight mass spectrometer (TOF/MS) for the identification of the resolved peaks. 28 components, which accounted for 77,7% of the oil, were identified. The main components of this essential oil were 1,3,6,10-Dodecatetraene, 3,7,11-trimethyl-, (Z,E)- (α-Farnesene) (34.3%), Caryophyllene oxide (10.2%), 1,6-Octadien-3-ol, 3,7-dimethyl- (linalool) (10.2%). Essential oil also contained humulene (3.9%),caryophyllene (1.9%), methyl salicilate (1.15%), 2-hexanoylfuran (1.0%), gernacrene (1.1%). Based on the results of our experimental data and literature reviews, Perilla essential oil can represent special interest and can be used as an important natural substance for obtaining medicinal and preventive products with the several biological activities.

Topics: Gas Chromatography-Mass Spectrometry; Georgia (Republic); Monocyclic Sesquiterpenes; Oils, Volatile; Perilla; Polycyclic Sesquiterpenes; Sesquiterpenes

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

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

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

To date, volatile sex pheromones have not been identified in the Coccinellidae family; yet, various studies have suggested that such semiochemicals exist. Here, we collected volatile chemicals released by virgin females of the multicolored Asian lady beetle, Harmonia axyridis (Pallas), which were either allowed or not allowed to feed on aphids. Virgin females in the presence of aphids, exhibited "calling behavior", which is commonly associated with the emission of a sex pheromone in several Coleoptera species. These calling females were found to release a blend of volatile compounds that is involved in the remote attraction (i.e., from a distance) of males. Gas Chromatography-Mass Spectrometry (GC-MS) analyses revealed that (-)-β-caryophyllene was the major constituent of the volatile blend (ranging from 80 to 86%), with four other chemical components also being present; β-elemene, methyl-eugenol, α-humulene, and α-bulnesene. In a second set of experiments, the emission of the five constituents identified from the blend was quantified daily over a 9-day period after exposure to aphids. We found that the quantity of all five chemicals significantly increased across the experimental period. Finally, we evaluated the activity of a synthetic blend of these chemicals by performing bioassays which demonstrated the same attractive effect in males only. The results confirm that female H. axyridis produce a volatile sex pheromone. These findings have potential in the development of more specific and efficient biological pest-control management methods aimed at manipulating the behavior of this invasive lady beetle.

Topics: Animals; Aphids; Coleoptera; Eating; Eugenol; Gas Chromatography-Mass Spectrometry; Monocyclic Sesquiterpenes; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Guaiane; Sex Attractants; Sexual Behavior, Animal

Trans-caryophyllene is a sesquiterpene present in many medicinal plants' essential oils, such as Ocimum gratissimum and Cannabis sativa. In this study, we evaluated the antinociceptive activity of trans-caryophyllene in murine models of acute and chronic pain and the involvement of trans-caryophyllene in the opioid and endocannabinoid systems. Acute pain was determined using the hot plate test (thermal nociception) and the formalin test (inflammatory pain). The chronic constriction injury (CCI) of the sciatic nerve induced hypernociception was measured by the hot plate and von Frey tests. To elucidate the mechanism of action, mice were pre-treated with naloxone or AM630 30 min before the trans-caryophyllene treatment. Afterwards, thermal nociception was evaluated. The levels of IL-1β were measured in CCI-mice by ELISA. Trans-caryophyllene administration significantly minimized the pain in both the acute and chronic pain models. The antinociceptive effect observed during the hot plate test was reversed by naloxone and AM630, indicating the participation of both the opioid and endocannabinoid system. Trans-caryophyllene treatment also decreased the IL-1β levels. These results demonstrate that trans-caryophyllene reduced both acute and chronic pain in mice, which may be mediated through the opioid and endocannabinoid systems.

Topics: Acute Pain; Administration, Oral; Analgesics; Animals; Cannabis; Chronic Pain; Formaldehyde; Hot Temperature; Hyperalgesia; Inflammation; Interleukin-1beta; Male; Mice; Mice, Inbred C57BL; Naloxone; Ocimum; Oils, Volatile; Phytotherapy; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes

Genetic manipulation of plant volatile emissions is a promising tool to enhance plant defences against herbivores. However, the potential costs associated with the manipulation of specific volatile synthase genes are unknown. Therefore, we investigated the physiological and ecological effects of transforming a maize line with a terpene synthase gene in field and laboratory assays, both above- and below ground. The transformation, which resulted in the constitutive emission of (E)-β-caryophyllene and α-humulene, was found to compromise seed germination, plant growth and yield. These physiological costs provide a possible explanation for the inducibility of an (E)-β-caryophyllene-synthase gene in wild and cultivated maize. The overexpression of the terpene synthase gene did not impair plant resistance nor volatile emission. However, constitutive terpenoid emission increased plant apparency to herbivores, including adults and larvae of the above ground pest Spodoptera frugiperda, resulting in an increase in leaf damage. Although terpenoid overproducing lines were also attractive to the specialist root herbivore Diabrotica virgifera virgifera below ground, they did not suffer more root damage in the field, possibly because of the enhanced attraction of entomopathogenic nematodes. Furthermore, fewer adults of the root herbivore Diabrotica undecimpunctata howardii were found to emerge near plants that emitted (E)-β-caryophyllene and α-humulene. Yet, overall, under the given field conditions, the costs of constitutive volatile production overshadowed its benefits. This study highlights the need for a thorough assessment of the physiological and ecological consequences of genetically engineering plant signals in the field to determine the potential of this approach for sustainable pest management strategies.

Topics: Alkyl and Aryl Transferases; Animals; Genetic Engineering; Herbivory; Insecta; Monocyclic Sesquiterpenes; Nematoda; Plant Development; Plant Roots; Plants, Genetically Modified; Polycyclic Sesquiterpenes; Risk Assessment; Sesquiterpenes; Terpenes; Volatile Organic Compounds; Zea mays

Hop cones, the immature inflorescences of the female plant of Humulus lupulus L., have been used for centuries to improve the flavor of beer and can be also used for a great variety of other products. Four samples of hop, belonging to three different cultivars (Nugget, Saaz and Perle), were studied in the present work. Headspace solid-phase microextraction and hydrodistillation techniques were used to obtain the volatile profiles of the samples.. Independent of the technique employed, over 40 volatile compounds were detected in the hop pellet samples (esters, monoterpenes, monoterpenoids, sesquiterpenes and sesquiterpenoids). Sesquiterpenes and sesquiterpenoids represented the majority of the total aromatic compounds. The main compounds for all cultivars were myrcene, β-caryophyllene and humulene, but the presence of high amounts of β-farnesene in Saaz cultivar was highlighted.. Both techniques were suitable for studying qualitatively the volatile composition of hop pellets, but some differences were shown when studying the proportion of the main constituents of the volatile profiles. Understanding these differences may help researchers design future studies to advise the industry how to exploit the potential of each hop cultivar.

Topics: Acyclic Monoterpenes; Alkenes; Beer; Distillation; Humulus; Inflorescence; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Solid Phase Microextraction; Species Specificity

Entomopathogenic nematodes (EPNs) respond to a variety of stimuli when foraging. In a laboratory investigation, we tested the chemotactic responses of 8 EPN strains (Steinernema and Heterorhabditis) to three mechanically damaged maize root compounds (linalool, α-caryophyllene and β-caryophyllene). We hypothesized that the EPN directional response to the tested volatile compounds would vary among the species and volatile compound and may be related to foraging strategies. The nematodes with an intermediate foraging strategy (Steinernema feltiae) proved to be less active in their movement toward volatile compounds in a comparison with the ambushers (Steinernema carpocapsae) and cruisers (Steinernema kraussei and Heterorhabditis bacteriophora); β-caryophyllene was found to be the most attractive substance in our experiment. The results of our investigation showed that the cruisers were more attracted to β-caryophyllene than the ambushers and intermediates. The foraging strategy did not affect the movement of the IJs toward the other tested volatile compounds or the control. Our results suggest that the response to different volatile cues is more a strain-specific characteristic than a different host-searching strategy. Only S. carpocapsae strain B49 displayed an attraction to linalool, whereas S. kraussei showed a retarded reaction to β-caryophyllene and α-caryophyllene in our experiment. The EPN strains showed only a weak attraction to α-caryophyllene, suggesting that this volatile compound could not have an important role in the orientation of IJs to the damaged roots of maize plants. These results expand our knowledge of volatile compounds as the cues that may be used by EPNs for finding hosts or other aspects of navigation in the soil.

Topics: Acyclic Monoterpenes; Analysis of Variance; Animals; Chemotaxis; Monocyclic Sesquiterpenes; Monoterpenes; Movement; Plant Roots; Polycyclic Sesquiterpenes; Rhabditida; Rhabditoidea; Sesquiterpenes; Soil; Time Factors; Volatilization; Zea mays

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

The sesquiterpene isomers, β-Cariofileno (CAR) and α-Humuleno (HUM) are the primary constituents of the copaiba oleoresin species. These natural products are primarily used by the Amazonian population and marketed as phytotherapies and cosmetics. The aim of this study was to develop and validate a method that simultaneously assays the isomers present in copaiba oleoresins by high performance liquid chromatography using the Box-Behnken design. After preliminary studies, the reverse phase chromatographic system was selected using a cyano column and a mobile phase consisting of acetonitrile and phosphate buffer. The Box-Behnken design was applied at three levels and with four independent variables: flow rate (X1), gradient slope time (X2), proportion of organic compounds at the end of the gradient (X3) and at the beginning of the gradient (X4). Also, the responses of the dependent variables: CAR retention time (Y1) and the resolution between the CAR and HUM peaks (Y2) was assessed. The mathematical model obtained from the regression results was satisfactory (R(2)>0.98, n=27) and showed a quadratic relationship where the effects of interactions between the variables, was observed by response surface graphs. The simultaneous optimization method was used to establish the best compromise of the resolution between the CAR and HUM isomers while adjusting the retention time of CAR. This method was successfully optimized by BBD obtaining chromatographic peaks with good symmetry, resolution and separation efficiency. The validation of the developed method confirmed its specificity, precision, accuracy and linearity in the range of 5.0-11.0 and 0.4-1.0μg/mL for CAR and HUM, respectively, and is considered suitable for routine applications which assure quality control.

Topics: Chromatography, High Pressure Liquid; Fabaceae; Isomerism; Linear Models; Monocyclic Sesquiterpenes; Plant Preparations; Polycyclic Sesquiterpenes; Reproducibility of Results; Research Design; Sensitivity and Specificity; Sesquiterpenes

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

Plant-based whole foods provide thousands of bioactive metabolites to the human diet that reduce the risk of developing chronic diseases. β-Caryophyllene (CAR) is a common constituent of the essential oil of numerous plants, vegetables, fruits and medicinal herbs, and has been used as a flavouring agent since the 1930 s. Here, we report the antioxidant activity of CAR, its protective effect on liver fibrosis and its inhibitory capacity on hepatic stellate cell (HSC) activation. CAR was tested for the inhibition of lipid peroxidation and as a free radical scavenger. CAR had higher inhibitory capacity on lipid peroxidation than probucol, α-humulene and α-tocopherol. Also, CAR showed high scavenging activities against hydroxyl radical and superoxide anion. The activity of 5-lipoxygenase, an enzyme that actively participates in fibrogenesis, was significantly inhibited by CAR. Carbon tetrachloride-treated rats received CAR at 2, 20 and 200 mg/kg. CAR significantly improved liver structure, and reduced fibrosis and the expression of Col1a1, Tgfb1 and Timp1 genes. Oxidative stress was used to establish a model of HSC activation with overproduction of extracellular matrix proteins. CAR (1 and 10 μm) increased cell viability and significantly reduced the expression of fibrotic marker genes. CAR, a sesquiterpene present in numerous plants and foods, is as a natural antioxidant that reduces carbon tetrachloride-mediated liver fibrosis and inhibits hepatic cell activation.

Topics: alpha-Tocopherol; Animals; Antioxidants; Arachidonate 5-Lipoxygenase; Carbon Tetrachloride Poisoning; Cell Line; Cell Survival; Dietary Supplements; Female; Flavoring Agents; Free Radical Scavengers; Hepatic Stellate Cells; Lipid Peroxidation; Lipoxygenase Inhibitors; Liver; Monocyclic Sesquiterpenes; Oxidative Stress; Polycyclic Sesquiterpenes; Probucol; Random Allocation; Rats; Rats, Wistar; Sesquiterpenes

Copaifera species (Leguminoseae) are popularly known as "copaiba" or "copaíva". The oleoresins obtained from the trunk of these species have been extensively used in folk medicine and are commercialized in Brazil as crude oil and in several pharmaceutical and cosmetic products. This work reports a complete validated method for the quantification of β-caryophyllene, α-copaene, and α-humulene in distinct copaiba oleoresins available commercially. Thus, essential oil samples (100μL) were dissolved in 20mL of hexanes containing internal standard (1,2,4,5-tetramethylbenzene, 3.0mM) in a 25mL glass flask. A 1μL aliquot was injected into the GC-FID system. A fused-silica capillary column HP-5, coated with 5% phenyl-methylsiloxane was used for this study. The developed method gave a good detection response with linearity in the range of 0.10-18.74mM. Limits of detection and quantitation variety ranged between 0.003 and 0.091mM. β-Caryophyllene, α-copaene, and α-humulene were recovered in a range from 74.71% to 88.31%, displaying RSD lower than 10% and relative errors between -11.69% and -25.30%. Therefore, this method could be considered as an analytical tool for the quality control of different Copaifera oil samples and its products in both cosmetic and pharmaceutical companies.

Topics: Anti-Inflammatory Agents, Non-Steroidal; Balsams; Fabaceae; Flame Ionization; Gas Chromatography-Mass Spectrometry; Limit of Detection; Medicine, Traditional; Monocyclic Sesquiterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Quality Control; Reproducibility of Results; Sesquiterpenes; Statistics as Topic; Technology, Pharmaceutical

The root and leaf essential oils, present in trace amounts in Amsonia illustris Woods. (Apocynaceae), were isolated by steam distillation and their chemical constituents identified by GC-FID and GC-MS. More than 80% of the thirty volatile compounds in the leaf oil were identified, the major constituents being mainly sesquiterpenes like a-humulene (14.5%), beta-caryophyllene (12.4%) and guaiol (11.6%). The volatile ingredients of the root oil were pinocampheol, methyl salicylate, (2E,4E)- decadienal, eugenol and trans-isoeugenol.

Topics: Amsonia; Eugenol; Gas Chromatography-Mass Spectrometry; Monocyclic Sesquiterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Salicylates; Sesquiterpenes; Sesquiterpenes, Guaiane

To analyze the compositions of the essential oil from the leaves of Callicarpa integerrima.. GC-MS method was used.. 42 chemical constituents, accounting for 97.62% of total content were identified.. The main components were beta-caryophyllene (33.74%), Elixene (12.86%), tau-Cadinene (9.57%) and (-) -Spathulenol (8.99%). Besides, some sesquiterpenes and their oxides, such as Copaene (4.21%), Globulol (3.81%), alpha-Caryophyllene (2.48%), 2-Naphthalenemethanol, decahydro-alpha, alpha, 4a-trimethyl-8-methylene-[2R-(2alpha, 4aalpha, 8alphabeta)]-(2.37%) and 1,6-Cyclodecadiene (2.24%) had also relatively high contents.

Topics: Callicarpa; Gas Chromatography-Mass Spectrometry; Molecular Weight; Monocyclic Sesquiterpenes; Oils, Volatile; Plant Leaves; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes

The objective of this work was to investigate the antiulcerogenic and anti-inflammatory activities of the essential oil from Pterodon emarginatus seeds.. The following tests were used: ulcers induced by ethanol, indometacin and HCl/ethanol, and pleurisy induced by carrageenan in Swiss albino rats. The rats were treated by the oral route with essential oil of P. emarginatus seeds.. The essential oil at 100, 300 and 500 mg/kg exhibited significant protection against ulcers induced by ethanol, indometacin and HCl/ethanol (P < 0.001). The essential oil caused a marked reduction in the exudate volume and inhibited leucocyte and neutrophil influx (P < 0.05) in carrageenan-induced pleurisy. Moreover, the essential oil significantly decreased nitric oxide (NO) and interleukin-1 (IL-1) levels, without affecting tumour necrosis factor-alpha production.. The results demonstrated the marked antiulcerogenic and anti-inflammatory effects of the essential oil from P. emarginatus, which are, at least in part, a consequence of NO and IL-1 modulation. P. emarginatus or its constituents might represent new therapeutic options to treat gastric ulcers and inflammatory diseases.

Topics: Administration, Oral; Alkyl and Aryl Transferases; Animals; Anti-Inflammatory Agents; Anti-Ulcer Agents; Brazil; Carrageenan; Disease Models, Animal; Dose-Response Relationship, Drug; Ethanol; Fabaceae; Indomethacin; Interleukin-1alpha; Male; Medicine, Traditional; Mice; Monocyclic Sesquiterpenes; Nitric Oxide; Oils, Volatile; Omeprazole; Peptic Ulcer; Pleurisy; Polycyclic Sesquiterpenes; Ranitidine; Seeds; Sesquiterpenes; Tumor Necrosis Factor-alpha

The chemical composition of the essential oils from the leaves and stem bark of Eclipta prostrata (L.) L. and the aerial parts of Vernonia amygdalina Delile (Asteraceae) have been analyzed by capillary gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The investigation led to the identification of 33 and 30 compounds in the oils of the leaves and stem of E. prostrate, respectively, and 40 compounds in the oil of V. amygdalina. While the oil of the leaves of E. prostrata was highly dominated by sesquiterpenoids (89.3%), the stem bark was comprised of sesquiteprenoids (47.7%), straight chain hydrocarbons (25.6%) and monoterpenoids (11.1%). The main constituents of both oils were P-caryophyllene (47.7% and 15.9%) and a-humulene (31.8 and 12.9%) in the leaves and stem, respectively. In addition, (E)-beta-farnesene (10.0%) was also identified in significant amount in the stem bark. On the other hand, the major component of V. amygdalina oil was alpha-muurolol (45.7%).

Topics: Eclipta; Gas Chromatography-Mass Spectrometry; Monocyclic Sesquiterpenes; Oils, Volatile; Plant Components, Aerial; Polycyclic Sesquiterpenes; Sesquiterpenes; Vernonia

This study is aimed to evaluate the in vitro cytotoxicity of Senecio stabianus Lacaita (Asteraceae) against renal adenocarcinoma ACHN, hormone-dependent prostate carcinoma LNCaP, amelanotic melanoma C32 and human breast adenocarcinoma MCF-7 cell lines. The n-hexane extract showed an interesting activity with IC(50) values of 62.7 and 71.1 microg mL(-1) against C32 and LNCaP, respectively. Two compounds identified in the n-hexane extract, linalool and beta-caryophyllene, were found to be active against C32 cells (IC(50) values of 23.2 and 20.1 microg mL(-1), respectively). Among tested constituents, the highest activity was found when alpha-humulene was applied to LNCaP cells (IC(50) of 11.2 microg mL(-1)). In order to complete the phytochemical study on S. stabianus, which has not been investigated previously, the most characteristic secondary metabolites of Senecio genus, pyrrolizidine alkaloids (PAs), were analysed. Here we report the isolation, structural elucidation and identification of nine PAs.

Topics: Acyclic Monoterpenes; Cell Line, Tumor; Cell Proliferation; Cell Survival; Gas Chromatography-Mass Spectrometry; Hexanes; Humans; Monocyclic Sesquiterpenes; Monoterpenes; Plant Extracts; Polycyclic Sesquiterpenes; Pyrrolizidine Alkaloids; Senecio; Sesquiterpenes

To study the volatile oil of Murraya exotica.. The volatile oil of Murraya exotica was extracted by steam-stilling and was identified by GC-MS-DS.. More than 90 compounds were separated, and 59 compounds were identified, accounting for 93.9% of the total essential oil of Murraya exotica. The major constituents of volatile oil were bicyclogermacrene (26.0%), beta-caryophyllene (20.8%), alpha-caryophyllene (5.8%), delta-cadinene (4.7%), spathulenol (4.3%), trans-alpha-bergamotene (4.1%), germacrene D (3.7%), beta-bisabolene (3.0%), ar-Curcumene (2.5%).. The major components of Murraya exotica are the terpenoids, including 80.6% of sesquiterpenoids and 11.9% of monoterpenoids. Bicyclogermacrene is identified in Murraya genus for the first time.

Topics: Bridged Bicyclo Compounds; Gas Chromatography-Mass Spectrometry; Monocyclic Sesquiterpenes; Murraya; Oils, Volatile; Plant Leaves; Plant Stems; Plants, Medicinal; Polycyclic Sesquiterpenes; Seasons; Sesquiterpenes; Sesquiterpenes, Germacrane

Direct episulfidations of caryophyllene or humulene with elemental sulfur were examined by means of gas chromatography. Caryophyllene-6,7-episulfide was formed at an early stage in a reaction of the caryophyllene and elemental sulfur at 120 degrees C. Caryophyllene-3,6-sulfide and polymer compounds were formed after the episulfidation. Formations of the these compounds were related to the disappearance of the caryophyllene-6,7-episulfide. Isomerization from the caryophyllene to isocaryophyllene was also observed during the reaction. In the reaction of humulene with elemental sulfur, humulene-6,7-episulfide was initially produced and then converted to humulene-9,10-episulfide. It was assumed that the polymer compound in the reaction of humulene with sulfur was related to the disappearance of the both humulene episulfides.

Topics: Monocyclic Sesquiterpenes; Polycyclic Sesquiterpenes; Sesquiterpenes; Sulfides; Sulfur

The psychoactive cannabinoids from Cannabis sativa L. and the arachidonic acid-derived endocannabinoids are nonselective natural ligands for cannabinoid receptor type 1 (CB(1)) and CB(2) receptors. Although the CB(1) receptor is responsible for the psychomodulatory effects, activation of the CB(2) receptor is a potential therapeutic strategy for the treatment of inflammation, pain, atherosclerosis, and osteoporosis. Here, we report that the widespread plant volatile (E)-beta-caryophyllene [(E)-BCP] selectively binds to the CB(2) receptor (K(i) = 155 +/- 4 nM) and that it is a functional CB(2) agonist. Intriguingly, (E)-BCP is a common constituent of the essential oils of numerous spice and food plants and a major component in Cannabis. Molecular docking simulations have identified a putative binding site of (E)-BCP in the CB(2) receptor, showing ligand pi-pi stacking interactions with residues F117 and W258. Upon binding to the CB(2) receptor, (E)-BCP inhibits adenylate cylcase, leads to intracellular calcium transients and weakly activates the mitogen-activated kinases Erk1/2 and p38 in primary human monocytes. (E)-BCP (500 nM) inhibits lipopolysaccharide (LPS)-induced proinflammatory cytokine expression in peripheral blood and attenuates LPS-stimulated Erk1/2 and JNK1/2 phosphorylation in monocytes. Furthermore, peroral (E)-BCP at 5 mg/kg strongly reduces the carrageenan-induced inflammatory response in wild-type mice but not in mice lacking CB(2) receptors, providing evidence that this natural product exerts cannabimimetic effects in vivo. These results identify (E)-BCP as a functional nonpsychoactive CB(2) receptor ligand in foodstuff and as a macrocyclic antiinflammatory cannabinoid in Cannabis.

Topics: Administration, Oral; Animals; Binding Sites; Binding, Competitive; Cannabinoids; Cannabis; Carrageenan; Cells, Cultured; Computational Biology; Diet; Edema; Enzyme Activation; Extracellular Signal-Regulated MAP Kinases; GTP-Binding Protein alpha Subunits, Gi-Go; Humans; Interleukin-1beta; JNK Mitogen-Activated Protein Kinases; Ligands; Lipopolysaccharides; Mice; Monocytes; Oils, Volatile; Polycyclic Sesquiterpenes; Receptor, Cannabinoid, CB2; Sesquiterpenes; Signal Transduction; Tumor Necrosis Factor-alpha

The anti-inflammatory and anti-allergic effects of the essential oil of Cordia verbenacea (Boraginaceae) and some of its active compounds were evaluated. Systemic treatment with the essential oil of Cordia verbenacea (300-600mg/kg, p.o.) reduced carrageenan-induced rat paw oedema, myeloperoxidase activity and the mouse oedema elicited by carrageenan, bradykinin, substance P, histamine and platelet-activating factor. It also prevented carrageenan-evoked exudation and the neutrophil influx to the rat pleura and the neutrophil migration into carrageenan-stimulated mouse air pouches. Moreover, Cordia verbenacea oil inhibited the oedema caused by Apis mellifera venom or ovalbumin in sensitized rats and ovalbumin-evoked allergic pleurisy. The essential oil significantly decreased TNFalpha, without affecting IL-1beta production, in carrageenan-injected rat paws. Neither the PGE(2) formation after intrapleural injection of carrageenan nor the COX-1 or COX-2 activities in vitro were affected by the essential oil. Of high interest, the paw edema induced by carrageenan in mice was markedly inhibited by both sesquiterpenic compounds obtained from the essential oil: alpha-humulene and trans-caryophyllene (50mg/kg, p.o.). Collectively, the present results showed marked anti-inflammatory effects for the essential oil of Cordia verbenacea and some active compounds, probably by interfering with TNFalpha production. Cordia verbenacea essential oil or its constituents might represent new therapeutic options for the treatment of inflammatory diseases.

Topics: Animals; Anti-Allergic Agents; Anti-Inflammatory Agents; Carrageenan; Cordia; Cyclooxygenase 1; Cyclooxygenase 2; Dinoprostone; Edema; Interleukin-1beta; Mice; Monocyclic Sesquiterpenes; Neutrophils; Oils, Volatile; Peroxidase; Phytotherapy; Plant Extracts; Plant Leaves; Plants, Medicinal; Polycyclic Sesquiterpenes; Rats; Rats, Wistar; Sesquiterpenes; Tumor Necrosis Factor-alpha

Comptonia peregrina (L.) Coulter, a native plant from Canada used in traditional medicine against cancer, was extracted by hydrodistillation. Two fractions were collected, one over 0-30 min and one over 30-60 min, to assess the influence of time of hydrodistillation on the composition of essential oil. The chemical composition of these two extracts was determined by GC and GC-MS analyses. Fifty five components were identified: beta-caryophyllene (23.69% and 15.16%) and alpha-humulene (9.67% and 7.43%) were the major components in the 0-30 min and 30-60 min fractions, respectively, while beta-myrcene was detected in a higher amount in the 0-30 min fraction (12.58%) than in the 30-60 min fraction (0.15%). The cytotoxic activities of these fractions were assessed against human lung carcinoma cell line A-549 and human colon adenocarcinoma cell line DLD-1. Only the 30-60 min fraction was found to be active against both tumor cell lines, with GI(50) values of 66 +/- 12 microg/mL for A-549 and of 46 +/- 7 microg/mL for DLD-1. Two sesquiterpenes present in the oil, alpha-humulene and (E)-nerolidol, have been found to be cytotoxic against both tumor cell lines.

Topics: Cell Line, Tumor; Cell Proliferation; Cell Survival; Chromatography, Gas; Gas Chromatography-Mass Spectrometry; Humans; Monocyclic Sesquiterpenes; Myricaceae; Plant Leaves; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes

This study evaluated the anti-inflammatory properties of two sesquiterpenes isolated from Cordia verbenacea's essential oil, alpha-humulene and (-)-trans-caryophyllene. Our results revealed that oral treatment with both compounds displayed marked inhibitory effects in different inflammatory experimental models in mice and rats. alpha-humulene and (-)-trans-caryophyllene were effective in reducing platelet activating factor-, bradykinin- and ovoalbumin-induced mouse paw oedema, while only alpha-humulene was able to diminish the oedema formation caused by histamine injection. Also, both compounds had important inhibitory effects on the mouse and rat carrageenan-induced paw oedema. Systemic treatment with alpha-humulene largely prevented both tumor necrosis factor-alpha (TNFalpha) and interleukin-1beta (IL-1beta) generation in carrageenan-injected rats, whereas (-)-trans-caryophyllene diminished only TNFalpha release. Furthermore, both compounds reduced the production of prostaglandin E(2) (PGE(2)), as well as inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX-2) expression, induced by the intraplantar injection of carrageenan in rats. The anti-inflammatory effects of alpha-humulene and (-)-trans-caryophyllene were comparable to those observed in dexamethasone-treated animals, used as positive control drug. All these findings indicate that alpha-humulene and (-)-trans-caryophyllene, derived from the essential oil of C. verbenacea, might represent important tools for the management and/or treatment of inflammatory diseases.

Topics: Administration, Oral; Animals; Anti-Inflammatory Agents; Anti-Inflammatory Agents, Non-Steroidal; Brazil; Cordia; Cyclooxygenase 2; Dexamethasone; Dinoprostone; Edema; Interleukin-1beta; Male; Medicine, Traditional; Mice; Monocyclic Sesquiterpenes; Nitric Oxide Synthase Type II; Oils, Volatile; Plant Components, Aerial; Plants, Medicinal; Polycyclic Sesquiterpenes; Rats; Rats, Wistar; Sesquiterpenes; Tumor Necrosis Factor-alpha

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

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

beta-caryophyllene is a sesquiterpene widely distributed in essential oils of various plants. Several biological activities are attributed to beta-caryophyllene, such as anti-inflammatory, antibiotic, antioxidant, anticarcinogenic and local anaesthetic activities. In this work, the potentiating effect of beta-caryophyllene on the anticancer activity of alpha-humulene, isocaryophyllene and paclitaxel against MCF-7, DLD-1 and L-929 human tumour cell lines was evaluated. A non-cytotoxic concentration of beta-caryophyllene significantly increased the anticancer activity of alpha-humulene and isocaryophyllene on MCF-7 cells: alpha-humulene or isocaryophyllene alone (32 microg mL(-1)) inhibited cell growth by about 50% and 69%, respectively, compared with 75% and 90% when combined with 10 microg mL(-1) beta-caryophyllene. Moreover, beta-caryophyllene potentiated the anticancer activity of paclitaxel on MCF-7, DLD-1 and L-929 cell lines. The highest potentiating effect was obtained in DLD-1 cells treated with paclitaxel combined with 10 microg mL(-1) beta-caryophyllene, which increased the paclitaxel activity about 10-fold. The intracellular accumulation of paclitaxel-oregon green was evaluated in combination with concentrations of beta-caryophyllene ranging from 2.5 to 40 microg mL(-1). beta-Caryophyllene (10 microg mL(-1)) significantly increased the intracellular accumulation of paclitaxel-oregon green (about 64% over controls). Moreover, beta-caryophyllene induced intracellular accumulation of calcein but not verapamil, an inhibitor of P-glycoprotein and multidrug resistance related protein transporters, suggesting that beta-caryophyllene promotes drug accumulation by a different mechanism of action. These results suggest that beta-caryophyllene facilitates the passage of paclitaxel through the membrane and thus potentiates its anticancer activity.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Antineoplastic Agents; Cell Line, Tumor; Cell Proliferation; Dose-Response Relationship, Drug; Drug Synergism; Humans; Inhibitory Concentration 50; L Cells; Mice; Molecular Structure; Monocyclic Sesquiterpenes; Paclitaxel; Polycyclic Sesquiterpenes; Sesquiterpenes

An HPLC method has been developed for the simultaneous determination of aromatic and terpenic constituents of cloves on a C8 RP column, with the mobile phase consisting of a pH 3.5 phosphate buffer-triethylamine (30%) and acetonitrile (70%); a flow rate of 1.2 mL/min and a diode-array detector were used. Complete separation of all analytes (eugenol (EUG), eugenol acetate (AEUG), beta-caryophyllene, a-humulene and caryophyllene oxide) was achieved within 7 min. Good linearity was found in the range 0.125-40.0 microg/mL for EUG and AEUG and in the range 0.250-20.0 microg/mL for the terpenic compounds. After validation, the method was successfully applied to the analysis of clove oil and clove extract samples. The results obtained indicate good accuracy (recovery percentage mean value corresponding to 99.9%) and satisfactory precision.

Topics: Calibration; Chromatography, High Pressure Liquid; Eugenol; Humans; Molecular Structure; Monocyclic Sesquiterpenes; Plant Extracts; Plant Oils; Polycyclic Sesquiterpenes; Reproducibility of Results; Sensitivity and Specificity; Sesquiterpenes; Syzygium

The antioxidant activity of a commercial rectified clove leaf essential oil (Eugenia caryophyllus) and its main constituent eugenol was tested. This essential oil comprises in total 23 identified constituents, among them eugenol (76.8%), followed by beta-caryophyllene (17.4%), alpha-humulene (2.1%), and eugenyl acetate (1.2%) as the main components. The essential oil from clove demonstrated scavenging activity against the 2,2-diphenyl-1-picryl hydracyl (DPPH) radical at concentrations lower than the concentrations of eugenol, butylated hydroxytoluene (BHT), and butylated hydroxyanisole (BHA). This essential oil also showed a significant inhibitory effect against hydroxyl radicals and acted as an iron chelator. With respect to the lipid peroxidation, the inhibitory activity of clove oil determined using a linoleic acid emulsion system indicated a higher antioxidant activity than the standard BHT.

Topics: Antioxidants; Biphenyl Compounds; Butylated Hydroxyanisole; Butylated Hydroxytoluene; Eugenol; Free Radical Scavengers; Linoleic Acid; Monocyclic Sesquiterpenes; Oils, Volatile; Picrates; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Syzygium; Thiobarbituric Acid Reactive Substances

The traceability of Asiago mountain cheese was established by analyzing samples of herbaceous species, milk, and cheese of mountain origin using the head-space solid-phase microextraction sampling procedure coupled with gas chromatography-mass spectrometry. As preliminary work had highlighted the characteristic presence of sesquiterpenes in Asiago mountain cheese, these species were considered effective markers of mountain origin. Systematic qualitative analysis, carried out using a carboxen/polydimethylsiloxane fiber, revealed several sesquiterpenes in mountain herbage and milk, in particular beta-caryophyllene and alpha-humulene, in Asiago mountain cheese, confirming sesquiterpenes as markers of cheese produced from animals grazing on mountain pastures. Analysis was performed on 19 samples of herbage, 8 of milk, and 8 of cheese, collected in summer from 4 mountain farms on the Asiago plateau. For quantitative analysis of caryophyllene in cheese, polydimethylsiloxane fiber sampling, coupled with the standard addition method to eliminate matrix effect, was preferred. The amount of beta-caryophyllene found ranged from 21 to 65 microg/kg.

Topics: Altitude; Animals; Cheese; Gas Chromatography-Mass Spectrometry; Geography; Milk; Monocyclic Sesquiterpenes; Polycyclic Sesquiterpenes; Sesquiterpenes

The objective of this study was to determine harvest yield and essential oil composition of six hop cultivars ("Fredos derlingieji", "Alta", "Granit", "Marynka", "Dubskij zeleniak" and "Aromat polessja") cultivated in Lithuania. It was found that the highest crop can be obtained from early and middle harvest varieties, which mature during the first decade of September and the third decade of August. Late harvest cultivars are not suitable for cultivation, however they can be used for the development of new cultivars. Essential oils were isolated by hydrodistillation and analyzed by gas chromatography and mass spectrometry. The highest amount of essential oil was determined in Marynka cultivar (2.10 ml/100 g), the lowest one in Dubskij zeleniak 18 (0.46 ml/100 g). Totally, 62 compounds were identified in all cultivars. Myrcene, beta-caryophyllene, alpha-humulene and beta-farnesene (E) were major constituents in the essential oils. The differences in the content of other essential oil constituents were determined. Some cultivars were rich in esters and ketones.

Topics: Chromatography, Gas; Climate; Humans; Humulus; Lithuania; Mass Spectrometry; Monocyclic Sesquiterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Seasons; Sesquiterpenes

Atherosclerosis is a vascular disorder involving inflammation, a narrowed vascular lumen in the entire tunica intima, and reduced elasticity of the arterial wall. It has been found that Hsp60 from Chlamydia pneumoniae, an obligate bacterial pathogen associated with atheroma lesions, mimics human Hsp60, thereby causing attacks by immune cells on stressed endothelial cells expressing endogenous Hsp60 on their surface. Furthermore, Hsp60 from C. pneumoniae has been shown to promote the growth of vascular smooth muscle cells (VSMCs). To explore probes that can be used for studying signal transduction elicited by the chlamydial Hsp60, we have tested several natural products for their inhibitory actions on the Hsp60-induced proliferation of rat arterial smooth muscle cells. Sesamol, vanillyl alcohol, and trans-ferulic acid exhibited moderate inhibitory actions on the Hsp60-induced cell proliferation; zerumbone, humulene, and caryophylene effectively inhibited it at low concentrations with IC(50) values of 529, 122, and 110 nM, respectively. The results indicated that the 11-membered alicyclic ring is favorable for interactions with receptors involved in the Hsp60-induced VSMC proliferation.

Topics: Animals; Benzodioxoles; Cell Division; Chaperonin 60; Chlamydophila pneumoniae; Monocyclic Sesquiterpenes; Muscle, Smooth, Vascular; Phenols; Polycyclic Sesquiterpenes; Rats; Sesquiterpenes

To study the chemical constituents of the essential oil from the roots and rhizomes of Patrinia rupestris.. The essential oil was extracted by steam distillation. The components were separated and identified by gas chromatography mass spectrometry and elucidated on the standard mass spectral data. Gas chromatography showed their percentages by area normalization method.. Seventeen constituents were identified which make up 74.57% of the oil.. Transcaryophyllene (38.41%) was the main constituent, and other constituents include alpha-gurjunene, caryophyllene oxide, humulene, 9,12-octadecadienoic acid, etc.

Topics: Gas Chromatography-Mass Spectrometry; Monocyclic Sesquiterpenes; Oils, Volatile; Patrinia; Plant Roots; Plants, Medicinal; Polycyclic Sesquiterpenes; Rhizome; Sesquiterpenes; Stereoisomerism

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

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

Humulene cyclase and caryophyllene cyclase, two enzymes which catalyze the cyclization of farnesyl pyrophosphate to the respective sesquiterpene olefins, have been partially purified from the supernatant fraction of a sage (Salvia officinalis) leaf epidermis extract and separated from each other by a combination of hydrophobic interaction, gel filtration, and ion-exchange chromatography. The molecular weight of both cyclases was estimated by gel filtration to be 57,000 and both cyclases exhibited a pH optimum of 6.5 and preferred Mg2+ (Km approximately 1.5 mM) as the required divalent metal cation. Both enzymes possessed a Km of about 1.7 microM for farnesyl pyrophosphate, were strongly inhibited by p-hydroxymercuribenzoate, and exhibited comparable sensitivities to a variety of other potential inhibitors. The properties of the two sesquiterpene olefin cyclases, which are the first from a higher plant source to be examined in detail, were very similar to each other and to other monoterpene, sesquiterpene, and diterpene cyclases previously described.

Topics: Chromatography, Gel; Chromatography, Ion Exchange; Cyclization; Isomerases; Monocyclic Sesquiterpenes; Plants; Polycyclic Sesquiterpenes; Polyisoprenyl Phosphates; Sesquiterpenes; Transferases

A soluble enzyme preparation obtained from sage (Salvia officinalis) leaves was shown to catalyze the divalent metal-ion dependent cyclization of trans, trans-farnesyl pyrophosphate to the macrocyclic sesquiterpene olefins humulene and caryophyllene. The identities of the biosynthetic products were confirmed by radiochromatographic analysis and by preparation of crystalline derivatives, and the specificity of labeling in the cyclization reaction was established by chemical degradation of the olefins derived enzymatically from [1-3H2]farnesyl pyrophosphate. These results constitute the first report on the cyclization of farnesyl pyrophosphate to humulene and caryophyllene, two of the most common sesquiterpenes in nature, and the first description of a soluble sesquiterpene cyclase to be isolated from leaves of a higher plant.

Topics: Chemical Phenomena; Chemistry; Chromatography, Gas; Cyclization; Monocyclic Sesquiterpenes; Plants; Polycyclic Sesquiterpenes; Polyisoprenyl Phosphates; Radiochemistry; Sesquiterpenes; Solubility