caryophyllene-oxide and caryophyllene

Medicinal plants and herbal preparations are gaining attention in the scientific community today, as they are often used intermittently in the treatment of various diseases. The genus of Polygonum (Polygonaceae), known locally as “madimak”, is an aromatic plant widely used in world flavors. The chemical composition of the essential oils of dried aerial parts of seven of Polygonum was analyzed by GC-MS. These species are Polygonum lapathifolium L., Polygonum persicaria L., Polygonum arenastrum Bor., Polygonum bellardii All., Polygonum arenarium Waldst. Et Kit., Polygonum aviculare L., and Polygonum cognatum Meissn. Qualitative and quantitative differences were found in the essential oil analysis of the seven Polygonum species. The major compounds were determined as (E)-β-farnesene (19. 46%), dodecanal (15.92%), β-caryophyllene (12.95%), in P. aviculare; (E)-β-farnesene (25.00%), dodecanal (20.45%), β-caryophyllene (9.38%), and caryophyllene oxide (8. 26%) in P. persicaria; dodecanal (25.65%), caryophyllene oxide (13.35%), β-caryophyllene (7.95%), and (E)-β-farnesene (6.20%) in P. lapathifolium, and dodecanal (19.65%), (E)-β-farnesene (13.86%), β-caryophyllene (8.06%), and α-terpineol (7.2%) in P. arenarium, dodecanal (16.23%), β-caryophyllene (16.09%), (E)-β-farnesene (12.26%), caryophyllene oxide (7.94%) in P. bellardii, (E)-β-farnesene (20.75%), dodecanal (17.96%), β-caryophyllene (13.01%), α-terpineol (4.97%) in P. arenastrum, (E)-β-farnesene (9.49%), dodecanal (14.01%), β-caryophyllene (11.92%), geranyl acetate (9.49%), and undecanal (7.35%) in P. cognatum. This study is the most comprehensive study conducted to determine the essential oil components of Polygonum species. In addition, a literature review on the composition of the essential oils of these Polygonum taxa was performed. The essential oil components of the species in our study were revealed for the first time with this study.

Topics: Oils, Volatile; Plant Oils; Polygonum; Turkey

Sesquiterpene compounds are applied as permeation promoters in topical formulations. However, studies exploring their impact on nanostructured systems, changes in permeation profile, and consequently, its biological activity are restricted. This study aimed to investigate the correlation between the skin permeation of the major sesquiterpenes, beta-caryophyllene, and caryophyllene oxide from the oleoresin of

Topics: Anti-Inflammatory Agents; Polycyclic Sesquiterpenes; Sesquiterpenes

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

Topics: Animals; Behavior, Animal; Female; HEK293 Cells; Horses; Humans; Male; Manure; Mice, Inbred C57BL; Phylogeny; Polycyclic Sesquiterpenes; Pyrimidinones; Rats, Wistar; Temperature; TRPM Cation Channels; Ursidae

Topics: Antioxidants; Artemisia; Artemisia annua; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Russia; Sesquiterpenes, Germacrane

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 essential oil isolated from Erica spiculifolia Salisb. by hydrodistillation was analysed by GC-MS. One hundred compounds representing 92.6% of total oil were identified. Among the detected compounds 38 were monoterpenoids (46.2%), 30 were sesquiterpenoids (31.7%), 2 diterpene (0.4%) and 30 compounds (14.3%) were with various non-terpenoid structures. Oxygenated monoerpenes were by far the main class (45.3%) with α-terpineol (7.5%) endo-borneol (7.2%), pinocarveol (5.9%) and thymol (3.7%) as the major compounds. The predominant components of sesquiterpenes were caryophyllene oxide (5.0%), caryophyllene (4.2%), τ -murrolol (3.5%), spathulenol (2.9) and α-cadinol (2.3%).

Topics: Bicyclic Monoterpenes; Cyclohexane Monoterpenes; Cyclohexenes; Ericaceae; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes

In the present study, the ability of the natural sesquiterpene β-caryophyllene (CRY) and its metabolite β-caryophyllene oxide (CRYO) to inhibit the genotoxicity of a condensate of cigarette smoke (CSC) was evaluated both in bacterial and mammalian cells. Also, the inhibition of the CSC-mediated STAT3 phosphorylation and intracellular oxidative stress was evaluated as potential chemopreventive mechanism. Under our experimental conditions, both the sesquiterpenes exhibited antimutagenic properties, being CRY the most potent compound. The antimutagenicity was highlighted in all experimental protocols, being particularly strong in the co- and post-treatments. The test substances also reduced the micronuclei frequency induced by CSC, with a major effectiveness of CRY. CRY was also able to reduce the CSC-mediated increase of the Y705- pSTAT3 levels, in spite of a lacking effect of CRYO. Furthermore, the sesquiterpenes CRY and CRYO displayed a moderate antioxidant activity, with a 25 % and 40 % inhibition of the ROS-levels increased by CSC, respectively. On the basis of these results, CRY seems to be a multi-target chemopreventive agent, although the genoprotective and antioxidant effects of CRYO suggest that both compounds deserve to be deeply investigated for a possible application in the prevention and treatment of different smoke-related ailments.

Topics: Bacteria; DNA Damage; Gene Expression Regulation; Hep G2 Cells; Humans; Micronucleus Tests; Molecular Structure; Nicotiana; Polycyclic Sesquiterpenes; Reactive Oxygen Species; Sesquiterpenes; Smoke; STAT3 Transcription Factor

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

The natural sesquiterpenes β-caryophyllene (CRY) and β-caryophyllene oxide (CRYO) were evaluated for their potential chemosensitizing properties.. CRY and CRYO cytotoxicity was tested against the Caco-2, CCRF/CEM and CEM/ADR5000 human cancer cell lines. Furthermore, combination experiments were carried out in order to study the ability of the sesquiterpenes to increase doxorubicin cytotoxicity. The possible interference of CRY and CRYO with functionality of ATP-binding cassette (ABC)-transporters was also investigated by Rhodamine123 efflux assay.. Despite a low cytotoxicity, both substances were able to enhance the cytotoxicity of doxorubicin in all cell lines, with CRYO being the most effective reversal agent. Both sesquiterpenes were also able to increase the Rho123 content into cells, likely due to inhibition of the efflux pumps.. Our results highlight a potential role of CRY and CRYO as new chemosensitizing agents for doxorubicin chemotherapy and to re-sensitize cancer-resistant cells.

Topics: Antineoplastic Combined Chemotherapy Protocols; Caco-2 Cells; Cell Line, Tumor; Cell Survival; Dose-Response Relationship, Drug; Doxorubicin; Drug Resistance, Multiple; Drug Resistance, Neoplasm; Drug Screening Assays, Antitumor; Humans; Inhibitory Concentration 50; Polycyclic Sesquiterpenes; Rhodamine 123; Sesquiterpenes

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 chemical composition of essential oil obtained from the aerial parts of Ajuga comata Stapf. was analyzed by GC and GC/MS. Thirty-seven components were identified in the oil. (E)-β-caryophyllene (30.9%), caryophyllene oxide (24.9%), (E)-β-farnesene (12.6%), β-eudesmol (3.2%), δ-cadinene (3.1%) and germacrene D (3.0%) were the main compounds in the EOs. The chemical composition of A. comata Stapf. from the Southern Zagros of Iran is reported for the first time.

Topics: Ajuga; Gas Chromatography-Mass Spectrometry; Iran; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Eudesmane; Sesquiterpenes, Germacrane

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

Cigarette filters pose a serious litter and toxic waste disposal problem, because of their not biodegradability and to the leaching of toxins in the environment. Therefore, cigarette butts need to be manipulated as special waste, with potential risks to human health and environment. In the present study, the genotoxic potential of a methanol extract from commonly discharged cigarette butts (CBE) was evaluated in the bacterial reverse mutation assay on Salmonella typhimurium TA98 and TA100 and Escherichia coli WP2uvrA strains, both in the absence and presence of the S9 exogenous metabolic activator. Furthermore, the ability of the natural sesquiterpenes β-caryophyllene (CRY) and β-caryophyllene oxide (CRYO) to inhibit the mutagenicity of CBE was studied as a possible preventive strategy. In order to identify the potential antimutagenic mechanisms, three different protocols (pretreatment, cotreatment, and posttreatment) were applied. CBE showed to increase the number of revertant colonies in all the strains tested in presence of S9, so resulting mutagenic. In the antimutagenicity assay, both CRY and CRYO significantly reduced the revertant colonies induced by CBE, although with different potency and specificity. For both sesquiterpenes, the antimutagenicity was strong in all experimental conditions, except for the cotreatment of CRY with CBE in WP2uvrA, which produced a moderate inhibition. Both desmutagenic and bioantimutagenic mechanisms seem to be involved in the antimutagenicity of the test substances. Taking into account the potential genotoxicity of cigarette butts, CRY and CRYO appear as possible further candidates as environmental decontaminants against this hazardous waste. © 2015 Wiley Periodicals, Inc. Environ Toxicol 31: 1319-1328, 2016.

Topics: Biological Assay; Escherichia coli; Humans; Mutagenicity Tests; Polycyclic Sesquiterpenes; Protective Agents; Salmonella typhimurium; Sesquiterpenes; Tobacco Products

The chemical composition of the essential oil obtained from aerial parts of Nepeta graciliflora was analysed, for the first time, by GC-FID and GC-MS. A total of 27 compounds were identified, constituting over 91.44% of oil composition. The oil was strongly characterised by sesquiterpenes (86.72%), with β-sesquiphellandrene (28.75%), caryophyllene oxide (12.15%), α-bisabolol (8.97%), α-bergamotene (8.51%), β-bisabolene (6.33%) and β-Caryophyllene (5.34%) as the main constituents. The in vitro activity of the essential oil was determined against four micro-organisms in comparison with chloramphenicol by the agar well diffusion and broth dilution method. The oil exhibited good activity against all tested organisms.

Topics: Anti-Bacterial Agents; Bridged Bicyclo Compounds; Gas Chromatography-Mass Spectrometry; Microbial Sensitivity Tests; Monocyclic Sesquiterpenes; Nepeta; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes

The essential oils from leaves, twigs and trunk bark of Onychopetalum amazonicum R.E. Fr. (Annonaceae), obtained by hydrodistillation, were analysed by GC and GC-MS, and also were evaluated for in vitro antimicrobial activity. Forty-one compounds, which correspond to 75.0-92.2% of the oil components, were identified. Major compounds were sesquiterpenes, including (E)-caryophyllene, caryophyllene oxide, spathulenol, α-gurjunene, allo-aromadendrene and α-epi-cadinol. The oils were evaluated for antimicrobial activities against four bacteria strains and five pathogenic fungi. The oil of the trunk bark exhibited good activity against Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 10538 and Kocuria rhizophila ATCC 9341, with a minimal inhibitory concentration of 62.5 μg/mL. The essential oil composition and the antimicrobial evaluation are reported for the first time for the genus Onychopetalum.

Topics: Annonaceae; Anti-Infective Agents; Azulenes; Escherichia coli; Gas Chromatography-Mass Spectrometry; Microbial Sensitivity Tests; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Staphylococcus epidermidis; Terpenes

The therapeutic agents for dementia are limited due to the complex system underlying the mechanisms. Taking a preventive point of view, we focused on the inhibition of β-secretase and acetylcholinesterase (AChE). In addition, plant resources including herbs and spices have been widely consumed, and further, may be consumed for a long period over a lifetime. Considering this background, we screened β-secretase and AChE inhibitors from curry spices. Amongst them, curry leaf, black pepper, and turmeric extracts were effective to inhibit β-secretase. Furthermore, black pepper and turmeric extracts were also effective to inhibit AChE. Having these results in hand, we focused on the investigation of β-secretase inhibitors since the inhibitor of this enzyme has not previously been well investigated. As a result, α- and β-caryophyllene, β-caryophyllene oxide (from curry leaf), piperine (from black pepper), curcumin, demethoxycurcumin, and bisdemethoxycurcumin (from turmeric) were successfully identified as low molecular inhibitors. This is the first report to determine α- and β-caryophyllene, β-caryophyllene oxide, and piperine as β-secretase inhibitors. These compounds may pass through the blood brain barrier since their molecular weights are relatively low.

Topics: Acetylcholinesterase; Alkaloids; Amyloid Precursor Protein Secretases; Benzodioxoles; Cholinesterase Inhibitors; Curcuma; Curcumin; Diarylheptanoids; Murraya; Piper nigrum; Piperidines; Plant Extracts; Polycyclic Sesquiterpenes; Polyunsaturated Alkamides; Sesquiterpenes

The aim of this study was to analyse the composition of the essential oil (EO) of Lavandula coronopifolia from Morocco and to evaluate its in vitro antibacterial activity against antibiotic-resistant bacteria isolated from clinical infections. The antimicrobial activity was assessed by a broth micro-well dilution method using multiresistant clinical isolates of 11 pathogenic bacteria: Klebsiella pneumoniae subsp. pneumoniae, Klebsiella ornithinolytica, Escherichia coli, Enterobacter cloacae, Enterobacter aerogenes, Providencia rettgeri, Citrobacter freundii, Hafnia alvei, Salmonella spp., Acinetobacter baumannii and methicillin-resistant Staphylococcus aureus. The main compounds of the oil were carvacrol (48.9%), E-caryophyllene (10.8%) and caryophyllene oxide (7.7%). The oil showed activity against all tested strains with minimal inhibitory concentration (MIC) values ranging between 1% and 4%. For most of the strains, the MIC value was equivalent to the minimal bactericidal concentration value, indicating a clear bactericidal effect of L. coronopifolia EO.

Topics: Anti-Bacterial Agents; Cymenes; Drug Resistance, Multiple, Bacterial; Lavandula; Microbial Sensitivity Tests; Monoterpenes; Morocco; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes

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

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

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

GC/FID and GC-MS analysis revealed germacrene D, bicyclogermacrene, α-cadinol and cubenol as major compounds from aril. Germacrene D, bicyclogermacrene, trans-caryophyllene and δ-elemene are major compounds in fruits. Germacrene D, spathulenol, trans-caryophyllene and caryophyllene oxide are major compounds in leaves. Furthermore, multivariate analysis revealed distinct groups between the composition of essential oils from aril and fruit, when compared with terpene production found in leaves. Lipid composition found in arils could be protected by the presence of non-oxygenated sesquiterpenes, as germacrene D and bicyclogermacrene. Chemical profiles of essential oils from the fruits, arils and leaves of Copaifera langsdorffii Desf. revealed different compositions, which could be related to environmental pressures. Thereby, non-oxygenated sesquiterpenes can also work against herbivory, pathogens and predator's attack, emphasising the importance of further studies among terpenes, ecology interactions and plant physiology.

Topics: Fabaceae; Fruit; Gas Chromatography-Mass Spectrometry; Oils, Volatile; Plant Leaves; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes

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

Aegle marmelos (Indian Bael) is a tree which belongs to the family of Rutaceae. It holds a prominent position in both Indian medicine and Indian culture. We have screened various fractions of Aegle marmelos extracts for their anticancer properties using in vitro cell models. Gas chromatography-Mass spectrometry (GC-MS) was employed to analyze the biomolecules present in the Aegle marmelos extract. Jurkat and human neuroblastoma (IMR-32) cells were treated with different concentrations of the fractionated Aegle marmelos extracts. Flow cytometric analysis revealed that optimal concentration (50 µg/ml) of beta caryophyllene and caryophyllene oxide fractions of Aegle marmelos extract can induce apoptosis in Jurkat cell line. cDNA expression profiling of pro-apoptotic and anti-apoptotic genes was carried out using real time PCR (RT-PCR). Down-regulation of anti-apoptotic genes (bcl-2, mdm2, cox2 and cmyb) and up-regulation of pro-apoptotic genes (bax, bak1, caspase-8, caspase-9 and ATM) in Jurkat and IMR-32 cells treated with the beta caryophyllene and caryophyllene oxide fractions of Aegle marmelos extract revealed the insights of the downstream apoptotic mechanism. Furthermore, in-silico approach was employed to understand the upstream target involved in the induction of apoptosis by the beta caryophyllene and caryophyllene oxide fractions of Aegle marmelos extract. Herein, we report that beta caryophyllene and caryophyllene oxide isolated from Aegle marmelos can act as potent anti-inflammatory agents and modulators of a newly established therapeutic target, 15-lipoxygenase (15-LOX). Beta caryophyllene and caryophyllene oxide can induce apoptosis in lymphoma and neuroblastoma cells via modulation of 15-LOX (up-stream target) followed by the down-regulation of anti-apoptotic and up-regulation of pro-apoptotic genes.

Topics: Aegle; Anti-Inflammatory Agents; Apoptosis; Apoptosis Regulatory Proteins; Arachidonate 15-Lipoxygenase; Chemical Fractionation; Computer Simulation; Humans; India; Jurkat Cells; Lymphoma; Molecular Targeted Therapy; Neuroblastoma; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes; Transcriptome

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

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

The aim of this research was to determine chemical composition and insecticidal activity of the essential oil of Illicium pachyphyllum fruits against two grain storage insects, Sitophilus zeamais and Tribolium castaneum, and to isolate any insecticidal constituents from the essential oil. The essential oil of I. pachyphyllum fruits was obtained by hydrodistillation and analyzed by GC-MS. A total of 36 components of the essential oil were identified, with the principal compounds in the essential oil being trans-ρ-mentha-1(7),8-dien-2-ol (24.56%), D-limonene (9.79%), caryophyllene oxide (9.32%), and cis-carveol (5.26%) followed by β-caryophyllene (4.63%) and bornyl acetate. Based on bioactivity-guided fractionation, the three active constituents were isolated and identified as trans-ρ-mentha-1(7),8-dien-2-ol, D-limonene and caryophyllene oxide. The essential oil of I. pachyphyllum fruits exhibited contact toxicity against S. zeamais and T. castaneum adults, with LD(50) values of 17.33 μg/adult and 28.94 μg/adult, respectively. trans-p-Mentha-1(7),8-dien-2-ol (LD(50) = 8.66 μg/adult and 13.66 μg/adult, respectively) exhibited stronger acute toxicity against S. zeamais and T. castaneum adults than either caryophyllene oxide (LD(50) = 34.09 μg/adult and 45.56 μg/adult) and D-limonene (LD(50) = 29.86 μg/adult and 20.14 μg/adult). The essential oil of I. pachyphyllum possessed fumigant toxicity against S. zeamais and T. castaneum adults with LC(50) values of 11.49 mg/L and 15.08 mg/L, respectively. trans-p-Mentha-1(7),8-dien-2-ol exhibited stronger fumigant toxicity against S. zeamais and T. castaneum adults, respectively, with LC(50) values of 6.01 mg/L and 8.14 mg/L, than caryophyllene oxide (LC(50) = 17.02 mg/L and 15.98 mg/L) and D-limonene (LC(50) = 33.71 mg/L and 21.24 mg/L). The results indicate that the essential oil of I. pachyphyllum fruits and its constituent compounds have potential for development into natural insecticides or fumigants for the control of insects in stored grains.

Topics: Animals; Camphanes; Cyclohexane Monoterpenes; Cyclohexenes; Edible Grain; Food Preservation; Food Storage; Fruit; Gas Chromatography-Mass Spectrometry; Illicium; Inhibitory Concentration 50; Insecticides; Limonene; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Tribolium; Weevils

The essential oil composition of Coleus aromaticus Benth. (family Lamiaceae) was examined by capillary GC and GC-MS. Analyses revealed the presence of 28 constituents, of which 16 were identified. Thymol (83.39%) was found to be the major compound, while 1-octen-3-ol, terpine-4-ol, eugenol, trans-caryophyllene, caryophyllene oxide and α-cadinol were present as minor constituents.

Topics: Chromatography, Gas; Coleus; Eugenol; Gas Chromatography-Mass Spectrometry; India; Octanols; Oils, Volatile; Plant Components, Aerial; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Thymol

The essential oils of Anthospermum emirnense Baker and Anthospermum perrieri Homolle ex Puff, obtained by hydrodistillation in 0.03 and 0.02% yield, respectively, were analyzed by GC/MS. In both cases, the major constituents consisted of sesquiterpene hydrocarbons and oxygenated sesquiterpenes. The two species showed an important qualitative similarity, with 40 compounds common to A. emirnense and A. perrieri, including β-elemene, trans-β-caryophyllene, caryophyllene oxide, and τ-cadinol, which were major components in both cases. When tested for antimicrobial activity, both essential oils showed similar profiles and exhibited interesting minimal-inhibitory-concentration (MIC) values towards Bacillus subtilis, Chryseobacterium indologenes, Flavimonas oryzihabitans, and Yersinia enterocolitica.

Topics: Anti-Infective Agents; Gas Chromatography-Mass Spectrometry; Microbial Sensitivity Tests; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Rubiaceae; Sesquiterpenes; Terpenes

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

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

The chemical compositions of the essential oils obtained by hydrodistillation from the aerial parts of Scutellaria diffusa, Scutellaria heterophylla and Scutellaria salviifolia were separately identified simultaneously by gas chromatography and gas chromatography-mass spectrometry. The main components were determined as hexadecanoic acid (30%) and caryophyllene oxide (9%) in the oil of S. diffusa. Germacrene D (21%), hexadecanoic acid (16%) and β-caryophyllene (13%) were found as major components in the oil of S. heterophylla. The main components of the oil of S. salviifolia were germacrene D (40%), bicyclogermacrene (14%) and β-caryophyllene (11%). Overall, individually 63, 68 and 43 constituents were identified in the aerial parts of S. diffusa, S. heterophylla and S. salviifolia essential oils representing 92.1%, 89.9% and 90% of the total, respectively.

Topics: Chromatography, Gas; Gas Chromatography-Mass Spectrometry; Oils, Volatile; Palmitic Acid; Polycyclic Sesquiterpenes; Scutellaria; Sesquiterpenes; Sesquiterpenes, Germacrane; Species Specificity; Turkey

Nemania aenea SF 10099-1, a basidiomycete isolated from a forest soil sample, regio- and stereoselectively epoxidized β-caryophyllene (Car) to (-)-β-caryophyllene oxide (Car-Ox) in a liquid-liquid interface bioreactor (L-L IBR) consisted of a liquid medium (a bottom phase), a fungus-ballooned microsphere (MS) mat (a middle phase), and an organic phase containing Car (a top phase). The cultivation conditions, such as carbon and nitrogen sources, kind of MS, initial medium pH and Car concentration, were optimized in the L-L IBR system. The best carbon and nitrogen sources were xylose and tryptone, respectively. The most suitable polyacrylonitrile MS was MMF-DE-1 (former MFL-80SDE; non-coated type). Although the strain could not grow below pH 5.5, the endocyclic epoxidation of Car efficiently proceeded at a wide range of initial medium pH (6.0 to 9.0). The bioconversion system exhibited an excellent alleviation effect toward substrate and product inhibitions. While Car could be added into an organic phase (KF-96L-1CS, dimethyl silicone oil) at 50% (w/v), the accumulation of Car-Ox reached over 30g/l in spite of these strong microbial toxicities. Moreover, the epoxidation reaction smoothly proceeded in a novel L-L IBR system, a multistory L-L IBR systems, consisted of 5 stacked reactor units. The optical rotation of Car-Ox produced was (-) and the enantiomeric excesses of (-)-β-Car-Ox purified by 1st and 2nd recrystallization from methanol reached 97.51 and 99.33%, respectively.

Topics: Animals; Bioreactors; Carbon; Microspheres; Nitrogen; Polycyclic Sesquiterpenes; Sesquiterpenes; Xylariales

The chemical composition of the essential oil from Heracleum rechingeri was analysed using GC-MS. Twenty-seven compounds, accounting for 94.62% of the extracted essential oil, were identified. The main oil compounds were octyl acetate (29.49%), elemicine (23.06%), (E)-caryophyllene (9.26%), caryophyllene oxide (6.42%), terpinolene (6.12%) and (Z)-3-octenyl acetate (4.72%). The antimicrobial activity of the essential oil was tested against three different bacteria by disc diffusion method and showed maximum inhibitory activity against Gram-positive bacteria, especially Bacillus subtilis.

Topics: Acetates; Anti-Bacterial Agents; Cyclohexane Monoterpenes; Gas Chromatography-Mass Spectrometry; Heracleum; Iran; Microbial Sensitivity Tests; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Staphylococcus aureus; Terpenes

The volatile constituents of the flowerheads of Centaurea nicaeensis All., C. parlatoris Helder and C. solstitialis L. ssp. schouwii (DC.) Dostál were extracted by hydrodistillation and analysed by GC and GC-MS. Altogether 113 components were identified. Fatty acids and hydrocarbons were the most abundant components in the oils. Caryophyllene and caryophyllene oxide were the main compounds of the sesquiterpene fraction. The study on the biological activity of the oils shows no significant activity.

Topics: Bacillus subtilis; Candida albicans; Centaurea; Chromatography, Gas; Flowers; Fusarium; Gas Chromatography-Mass Spectrometry; Italy; Microbial Sensitivity Tests; Oils, Volatile; Palmitic Acid; Plant Extracts; Plant Oils; Polycyclic Sesquiterpenes; Pseudomonas aeruginosa; Saccharomyces cerevisiae; Sesquiterpenes; Terpenes

To compare the chemical constituents of Aetherolea and Alcohol Extraction of purple common perilla of ChangBai Mountain.. We used water vapor distillation and alcohol extraction method, then analyzed identification by thin-layer chromatography and GC-MS.. The main chemical compositions of aetherolea were caryophyllen, caryophyllene oxid, ylangene, 4-(2-Methylcyclohex-1-enyl)-but-2-enal and 3,7-dimethyl-1,6-Octadien-3-ol and the main chemical compositions of alcohol extraction were 10-hendeca-acetylene-1-alcohol, n-hexsdecanoic acid (E)-7,11-dimethyl-3-methylene- 1,6,10-Dodecatriene and so on.. Other specific compositions including tau. -Muurolol,3H-3a,7-Methanoazulene,2 ,4,5,6,7,8-hexahydro-1,4,9,9-Tetram-ethyl-, [3aR-(3a. alpha, 4. beta 7. alpha)], Astaxanthin and Curan-17-oicacid, 19-acetyl-2,16-didehydro-20-hydroxy-, methyl ester, (19S) have special functions of sterilizing, cancer preventing and immunity improving, which are significantly different from the compositions extracted from other species.

Topics: beta Carotene; China; Chromatography, Thin Layer; Ethanol; Gas Chromatography-Mass Spectrometry; Oils, Volatile; Palmitic Acid; Perilla frutescens; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes; Technology, Pharmaceutical

Composition of the essential oil obtained from dried flowering aerial parts of Teucrium scordium L. (Labiatae) was analyzed by GC and GC/MS. Fifty-six components were identified in the essential oil of T. scordium. The major constituents of the oil were beta-caryophyllene (22.8%), (E)-beta-farnesene (10.4%), caryophyllene oxide (8.6%), 1,8-cineole (6.1%) and beta-eudesmol (5.1%).

Topics: Chromatography, Gas; Cyclohexanols; Eucalyptol; Flowers; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Eudesmane; Teucrium

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