caryophyllene-oxide and humulene

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

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 present study is designed to find out if sesquiterpenes, α-humulene (HUM), valencene (VAL), β-caryphyllene-oxide (CAO) and trans-nerolidol (NER), are able to improve the antiproliferative effect of classical cytostatic drugs, 5-fluorouracil (FU) and oxaliplatin (1,2-diaminocyclohexaneoxalato-platinum, OxPt), in colon cancer cell lines Caco-2 and SW-620. In addition, the possible mechanisms of sesquiterpene action are studied. The results show significant ability of HUM and especially of CAO to enhance the anti-proliferative effects of FU and OxPt in cancer cell lines Caco-2 and SW-620. On the other hand, VAL and NER are ineffective. The action of CAO could be partly based on its ability to disrupt the mitochondrial membrane potential and to activate initiator caspases, but other mechanisms are probably also involved. Based on these results, CAO seems to have the potential for combination therapy of colon cancers and deserves further study.

Topics: Caco-2 Cells; Cell Line, Tumor; Cell Proliferation; Colonic Neoplasms; Fluorouracil; Humans; Membrane Potential, Mitochondrial; Monocyclic Sesquiterpenes; Oxaliplatin; Polycyclic Sesquiterpenes; Sesquiterpenes

The chemical composition of the essential oil (EO) obtained from the aerial parts of Rydingia michauxii (Briq.) Scheen & V.A. Albert was analysed by gas chromatography and gas chromatography/mass spectrometry (GC/MS). Eighty components were identified in the oil with caryophyllene oxide (20.1%), trans-verbenol (10.2%), linalool (5.3%) and humulene epoxide II (4.6%) as main constituents. We reported here the chemical compositions of R. michauxii EOs from southern Zagros of Iran with a distinct chemical profile for the first time.

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

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

Topics: Cell Line, Tumor; Cell Proliferation; Cell Survival; Doxorubicin; Drug Resistance, Multiple; Drug Synergism; Drug Therapy, Combination; Humans; Monocyclic Sesquiterpenes; Myrica; Oils, Volatile; Polycyclic Sesquiterpenes; Precursor Cell Lymphoblastic Leukemia-Lymphoma; 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 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

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

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

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

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