caryophyllene and aromadendrene

Pamburus missionis (Wight) Swingle (Rutaceae) is traditionally used in the treatment of swellings, chronic rheumatism, paralysis and puerperal diseases. In a previous study the authors demonstrated apoptotic activity of Pamburus missionis essential oil (EO) on A431 and HaCaT cells. The major components of EO were β-caryophyllene (25.40%), 4(14),11- eudesmadiene (7.17%), aromadendrene oxide 2 (14.01%) (AO-(2) and phytol (6.88%).. To investigate the role as well as the interactions among EO components inducing apoptosis in A431 and HaCaT cells.. Isobolographic analysis and combination index methods were used to detect the type of interactions among the essential oil (EO) components. Cell viability was used to detect cytotoxic activity. Mechanism of cell death was studied using Annexin V-FITC/PI binding assay, cell cycle analysis, measurement of MMP and ROS generation by flow cytometry. Expression of apoptosis associated proteins was investigated by western blot.. Combination of P. missionis EO components: β-caryophyllene/ aromadendrene oxide 2 (β-C/AO-(2)), β-caryophyllene/phytol (β-C/P) and aromadendrene oxide 2 /phytol (AO-(2)/P) inhibited growth and colony formation ability of skin epidermoid A431 and precancerous HaCaT cells. Synergistic interaction was observed between β-C/AO-(2) and β-C/P combination while AO-(2)/P exhibited an additive effect. Combination of components induced chromatin condensation, phosphatidylserine externalisation, increase in sub-G1 DNA content, cell cycle arrest at G0/G1 phase and intracellular ROS accumulation. Inhibition of intracellular ROS by N-acetyl cysteine treatment blocked apoptosis induced by the combinations. The combinations induced apoptosis in A431 and HaCaT cells mediated by loss of mitochondrial membrane potential (ΔΨm), increase in Bax/Bcl-2 ratio, release of cytosolic cytochrome c and activation of caspases (cleaved form of caspase-3, caspase-8, caspase-9) and by PARP cleavage.. The present study demonstrates interactions among β-C, AO-(2) and P in the induction of apoptosis on A431 and HaCaT cells. These data suggest the combination of β-caryophyllene with aromadendrene oxide 2 and phytol could be potential therapeutics for the treatment of skin epidermoid cancer and precancerous cells.

Topics: Apoptosis; Azulenes; Carcinoma, Squamous Cell; Caspases; Cell Cycle Checkpoints; Cell Survival; Cytochromes c; Humans; Keratinocytes; Membrane Potential, Mitochondrial; Oils, Volatile; Phytol; Polycyclic Sesquiterpenes; Reactive Oxygen Species; Rutaceae; Sesquiterpenes

The genus Pamburus (Rutaceae) comprises the only species, Pamburus missionis (Wight) Swingle. Pamburus missionis is traditionally used in the treatment of swellings, chronic rheumatism, paralysis and puerperal diseases.. The present study investigates the cancer chemotherapeutic potential of essential oil (EO) from P. missionis.. EO was isolated by steam distillation and chemical composition was determined by GC-MS. Cell viability was used to detect cytotoxic activity. Mechanism of cell death was studied using Annexin V-FITC/PI binding, cell cycle analysis, measurement of MMP and ROS generation by flow cytometry. Expression of apoptosis related proteins was investigated by western blot.. GC-MS analysis of the essential oil revealed the presence of 51 components. The major components were β-Caryophyllene, 4(14),11-Eudesmadiene, Aromadendrene oxide-(2) and Phytol. EO inhibited the growth and colony formation ability of A431 and HaCaT cells. EO treatment induced nuclear condensation and loss of membrane integrity, DNA fragmentation, increase in sub-G1 DNA content and increase in intracellular ROS level. Inhibition of intracellular ROS by ascorbic acid and N-acetyl cysteine treatment blocked EO induced apoptosis, revealing that apoptotic activity was by ROS accumulation. EO induced apoptosis was found to be due to the loss of mitochondrial membrane potential (ΔΨm), increase in Bax/Bcl-2 ratio, release of cytochrome c and activation of caspases (cleaved form of caspase-3, caspase-8, caspase-9) and by PARP cleavage.. The present study revealed cancer chemotherapeutic potential of EO from P. missionis. EO induces cell death through intrinsic (mitochondrial) and extrinsic apoptotic pathway in A431 and HaCaT cells. These results suggest that EO could be used as a potential therapeutic agent for the treatment of skin epidermoid cancer.

Topics: Apoptosis; Azulenes; Carcinoma, Squamous Cell; Caspases; Cell Cycle; Cell Line, Tumor; Cell Survival; Cytochromes c; Humans; Membrane Potential, Mitochondrial; Mitochondria; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Reactive Oxygen Species; Rutaceae; Sesquiterpenes; Signal Transduction; Spheroids, Cellular

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

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

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

The essential-oil compositions of Pinus heldreichii Christ. from Montenegro and Serbia are reported at the population level. Whitebark pine is a sub-endemic high-mountain Balkan pine relict of an anthropogenically reduced area, with large morphological diversity and insufficiently clear taxonomic position. In the pine-needle terpene profile from three populations from Montenegro, and one from Serbia, 101 compounds were detected, 72 of which could be identified (Table 3). The dominant constituents are limonene (26.3%), alpha-pinene (17.5%), germacrene D (13.5%), and beta-caryophyllene (10.4%), comprising ca. 67.7% of the essential oil. Medium-to-high contents (0.5-10%) of the following 16 additional components were found: beta-pinene, beta-myrcene, alpha-humulene, delta-cadinene, alpha-muurolene, (E)-hex-2-enal, beta-gurjunene, gamma-muurolene, isopimarol, camphene, gamma-cadinene, aromadendrene, beta-bisabolene, trans-beta-farnesene, alpha-cadinene, and (Z)-hex-3-en-1-ol. The similarity of the populations and the within-population variability was visualized by principle-component analysis (PCA) of eleven selected terpenes in 97 tree samples. Cluster and genetic analyses suggest closest connection between the two spatially most-distant populations I (Montenegro) and IV (Serbia). Based on the profile of the main sesquiterpene components, the studied populations from Montenegro and Serbia are more similar to the populations from Greece and the Central Balkan peninsula (Bosnia and Serbia-Kosovo) than to those on the furthest eastern margin of their natural range (Bulgaria).

Topics: Acyclic Monoterpenes; Azulenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexenes; Limonene; Monoterpenes; Oils, Volatile; Pinus; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Yugoslavia

The essential oil from flowers of Mikania micrantha H.B.K were extracted and its chemical constituents were analyzed by GC/MS. Forty-two compounds were identified and the main compounds with high contents were beta-cubebene (12.95%), allo-aromadendrene (11.67%), beta-caryophyllene (9.17%), 1H-inden-1-one, 5-(1, 1-dimethylethyl)-2, 3-(6.23%), beta-himaohalene (4.56%), trans-alpha-bergamotene (4.09%), limonene (3.68%), beta-ocimene (2.53%).

Topics: Azulenes; Cyclohexenes; Flowers; Gas Chromatography-Mass Spectrometry; Limonene; Mikania; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes