caryophyllene and nerolidol

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

Terpenoids are a large group of important secondary metabolites that are involved in a variety of physiological mechanisms, and many are used commercially in the cosmetics and pharmaceutical industries. During the past decade, the topic of seasonal variation in terpenoid biosynthesis has garnered increasing attention. Formosan sweet gum ( Liquidambar formosana Hance) is a deciduous tree species. The expression of terpene synthase and accumulation of terpenoids in leaves may vary in different seasons. Here, four sesquiterpene synthases (i.e., LfTPS01, LfTPS02, LfTPS03, and LfTPS04) and a bifunctional mono/sesquiterpene synthase ( LfTPS05) were identified from Formosan sweet gum. The gene expression of LfTPS01, LfTPS02, and LfTPS03 showed seasonal diversification, and, in addition, expression of LfTPS04 and LfTPS05 was induced by methyl jasmonate treatment. The major products LfTPS01, LfTPS02, LfTPS04, and LfTPS05 are hedycaryol, α-selinene, trans-β-caryophyllene, α-copaene/δ-cadinene, and nerolidol/linalool, respectively. The data indicated that the sesquiterpenoid content in the essential oil of Formosan sweet gum leaves shows seasonal differences that were correlated to the sesquiterpene synthase gene expression.

Topics: Acyclic Monoterpenes; Alkyl and Aryl Transferases; Gene Expression; Liquidambar; Monoterpenes; Plant Leaves; Plant Proteins; Polycyclic Sesquiterpenes; Seasons; Sesquiterpenes

Topics: Acyclic Monoterpenes; Alkenes; Animals; Anti-Bacterial Agents; Bacillus subtilis; Drug Synergism; Lipopolysaccharides; Mice; Microbial Sensitivity Tests; Monoterpenes; Nitric Oxide; Oils, Volatile; Plant Extracts; Polycyclic Sesquiterpenes; Pseudomonas aeruginosa; Rubiaceae; Sesquiterpenes; Streptomycin

African rice gall midge, Orseolia oryzivora Harris and Gagné, is a major pest of rice in Africa. Depsite its economic importance, its chemical ecology is not well understood. Here, we assessed behavioral and electrophysiological responses of O. oryzivora to host plant volatiles. In olfactometer bioassays, mated female O. oryzivora were attracted to volatiles emitted from intact rice plants but were repelled by volatiles collected from plants infested by conspecifics. In a choice test, there was a preference for volatiles from uninfested plants over those from infested plants. Coupled gas chromatography-electroantennography analyses of panicle volatiles isolated four electrophysiologically active components: (S)-linalool, 4,8-dimethyl-1,3,7-nonatriene, (E)-caryophyllene, and (R/S)-(E)-nerolidol. A synthetic blend of volatiles at the same concentration and ratio as that from an intact plant was attractive to mated females, whereas a blend based on the ratio of volatiles from an infested plant was repellent. This suggests that O. oryzivora uses olfaction for host plant recognition. The identification of blends of volatiles emitted by plants that can both attract and repel O. oryzivora may aid the development of sustainable control measures.

Topics: Acyclic Monoterpenes; Animals; Behavior, Animal; Diptera; Electrophysiological Phenomena; Female; Gas Chromatography-Mass Spectrometry; Host-Parasite Interactions; Monoterpenes; Odorants; Olfactometry; Oryza; Polycyclic Sesquiterpenes; Seedlings; Sesquiterpenes; Terpenes; Volatilization

In natural habitats plants can be exposed to brief and light contact with neighbouring plants. This mechanical stimulus may represent a cue that induces responses to nearby plants. However, little is known about the effect of touching on plant growth and interaction with insect herbivores. To simulate contact between plants, a soft brush was used to apply light and brief mechanical stimuli to terminal leaves of potato Solanum tuberosum L. The number of non-glandular trichomes on the leaf surface was counted on images made by light microscope while glandular trichomes and pavement cells were counted on images made under scanning electronic microscope. Volatile compounds were identified and quantified using coupled gas chromatography-mass spectrometry (GC-MS). Treated plants changed their pattern of biomass distribution; they had lower stem mass fraction and higher branch and leaf mass fraction than untouched plants. Size, weight and number of tubers were not significantly affected. Touching did not cause trichome damage nor change their total number on touched terminal leaves. However, on primary leaves the number of glandular trichomes and pavement cells was significantly increased. Touching altered the volatile emission of treated plants; they released higher quantities of the sesquiterpenes (E)-β-caryophyllene, germacrene D-4-ol and (E)-nerolidol, and lower quantities of the terpenes (E)-ocimene and linalool, indicating a systemic effect of the treatment. The odour of touched plants was significantly less preferred by the aphids Macrosiphum euphorbiae and Myzus persicae compared to odour of untouched plants. The results suggest that light contact may have a potential role in the detection of neighbouring plants and may affect plant-insect interactions.

Topics: Acyclic Monoterpenes; Alkenes; Animals; Aphids; Herbivory; Mechanotransduction, Cellular; Monoterpenes; Plant Leaves; Plant Stems; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Solanum tuberosum; Touch; Trichomes

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

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

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

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

The chemical composition and antimicrobial activity studies on the essential oils of Hypericum rochelii Griseb. & Schenk and Hypericum umbellatum A. Kern. have been carried out for the first time. Seventy-nine compounds were identified in the essential oil of H. rochelii with n-nonane (24.7%), β-pinene (22.4%), germacrene D (7.5%), n-undecane (6.8%) and α-pinene (5.8%) as main constituents. One hundred and twenty-six compounds were identified in H. umbellatum essential oil with germacrene D (6.1%), (E)-nerolidol (4.4%), n-nonane (4.0%), (E)-caryophyllene (3.0%) and caryophyllene oxide (3.0%) as the most abundant components. Both oils were characterized by the presence of many components which could have numerous applications in food, pharmaceutical and perfume industries. Taxa studied herein belong to the section Drosocarpium Spach, and their intrasectional placement based on the essential oil profiles was discussed. The oils were tested in a broth microdilution assay against five bacterial and two fungal strains and found to have mainly moderate antimicrobial effects.

Topics: Alkanes; Anti-Infective Agents; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Hypericum; Monoterpenes; Oils, Volatile; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane

To study the chemical components and antitumor activities of essential oil from the fruits of Dasymaschalon trichophorum.. The essential oil from the fruits of Dasymaschalon trichophorum was extracted by steam-stilling and analyzed by GC-MS. The inhibitory effect of extract of Dasymaschalon trichophorum on SPCA-1,BEL-7402, SGC-7901 and K-562 cell proliferation was assayed using the MTU.. GC-MS result showed that there were 55 peaks and 30 compounds were identified which weighed 74.98%. The major components were nerolidol (19.887%), caryophyllene (16.714%) and beta-myrcene (9.29%). The essential oil exhibited strong antitumor activity against SPCA-1 human tumor cell line with IC50 value of 6.61 microg/mL.. This experiment provides scientific foundation for further utilization of Dasymaschalon trichophorum.

Topics: Acyclic Monoterpenes; Annonaceae; Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Cell Survival; Fruit; Gas Chromatography-Mass Spectrometry; Hot Temperature; Humans; Inhibitory Concentration 50; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes

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

The aim of this work was to analyze the essential oil content and its composition in the drug (Serpylli herba) of wild thyme (Thymus serpyllum L.) originating from 20 different natural places of growth in Estonia.. The quantitative content of essential oil was determined according to the method of European Pharmacopoeia. Gas chromatographic analysis of essential oils was carried out using a gas chromatography with flame ionization detector on two fused silica capillary columns with bonded stationary phases NB-30 and SW-10. The identification of the oil components was accomplished by comparing their retention indices on two columns with the retention indices values of standard compounds, with our retention indices data bank and with literature data. The results obtained were confirmed by gas chromatography / mass spectrometry.. The content of essential oil is between 0.6 and 4 ml/kg and usually is not in conformity with European Pharmacopoeia standard (3 ml/kg). There were 55 components identified in the essential oil of wild thyme of Estonian origin. Differently from the data in the literature of foreign countries, thymol and carvacrol are not the main components of the essential oil of wild thyme growing in Estonia. The main components here are (E)-nerolidol, caryophyllene oxide, myrcene, (E)-beta-caryophyllene and germacrene D.. In Estonia, the (E)-nerolidol-caryophyllene oxide, (E)-nerolidol-myrcene and myrcene chemotypes of wild thyme drug are distinguishable.

Topics: Anti-Inflammatory Agents, Non-Steroidal; Chromatography, Gas; Estonia; Humans; Mass Spectrometry; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Thymus Plant