caryophyllene and spathulenol

Topics: Brazil; Gas Chromatography-Mass Spectrometry; Myrtaceae; Oils, Volatile; Plant Leaves

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

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 purpose of this work was to study the chemical composition and antimycoplasmic and anticholinesterase activities of the essential oil of Eugenia hiemalis leaves collected throughout the year. A total of 42 compounds were identified by CG, and are present in almost every seasons. Sesquiterpenes were dominant (86.01-91.48%), and non-functionalised sesquiterpenes comprised the major fraction, which increased in the summer; monoterpenes were not identified. The major components were spathulenol (5.36-16.06%), δ-cadinene (7.50-15.93%), bicyclogermacrene (5.70-14.24%) and β-caryophyllene (4.80-9.43%). The highest oil yield was obtained in summer and autumn. Essential oils presented activity against three evaluated Mycoplasma strains, but no activity was observed in the anticholinesterase assay.

Topics: Anti-Bacterial Agents; Eugenia; Monoterpenes; Mycoplasma; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Seasons; 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

Water-distilled essential oil from Clinopodium chinense (Labiatae) aerial parts at the flowering stage was analyzed by gas chromatography-mass spectrometry. Thirty-five compounds, accounting for 99.18% of the total oil, were identified, and the main components of the essential oil of C. chinense were spathulenol (18.54%), piperitone (18.9%), caryophyllene (12.04%), and bornyl acetate (8.14%). Based on bioactivity-directed fractionation, bornyl acetate, caryophyllene, and piperitone were identified from the essential oil. The essential oil possessed fumigant toxicity against booklice (Liposcelis bostrychophila) with a 50% lethal concentration (LC50) value of 423.39 μg/liter, while the isolated constituents, bornyl acetate and piperitone, had LC50 values of 351.69 and 311.12 μg/liter against booklice, respectively. The essential oil also exhibited contact toxicity against L. bostrychophila with an LC50 value of 215.25 μg/cm(2). Bornyl acetate, caryophyllene, and piperitone exhibited acute toxicity against booklice with LC50 values of 321.42, 275.00, and 139.74 μg/cm(2), respectively. The results indicated that the essential oil and its isolated constituents have potential for development into natural insecticides or fumigants for control of insects in stored grains.

Topics: Animals; Camphanes; Cyclohexane Monoterpenes; Dose-Response Relationship, Drug; Gas Chromatography-Mass Spectrometry; Insecta; Insecticides; Lamiaceae; Lethal Dose 50; Monoterpenes; Oils, Volatile; Plant Components, Aerial; Polycyclic Sesquiterpenes; Sesquiterpenes; Toxicity Tests, Acute

As a peculiar folk medicinal plant, Acanthopanax brachypus was widely used to treat various diseases in China. At present, however, there is not a good quality standard for its quality evaluation. In this study, on the basis of the validation tests of precision, stability and repeatability, the chromatographic fingerprint of A. brachypus was established by using gas chromatography (GC)-flame ionization detector (FID) and GC-MS techniques, as well as computer aided similarity evaluation system. Thirty-two different batches of samples collected from the different producing regions and the different parts of A. brachypus were studied. The results showed that the dominant constituents of all oils were monoterpenes and sesquiterpenes, as well as oxygenated monoterpenes and sesquiterpenes. The fingerprinting profiles were found to be consistent for the fresh stem bark acquired from various production areas, 48 common peaks were determined, but the relative abundance of peaks was varied. β-Pinene, linalool, p-cymene, spathulenol, camphene, endo-borneol, verbenone, β-caryophyllene, γ-terpinene, germacrene-D, camphor, β-thujone and β-cadinene were the main constituents of the fresh stem bark oil. Except for the leaf, the chemical components among different medicinal parts of fresh plant were inconsistent with the stem bark. Besides, the varieties and relative levels of chemical components in the fresh stem bark were more abundant than in the dry counterpart. The GC-MS fingerprint can be successfully applied to distinguish the substitute or adulterant, and further assess the differences of A. brachypus grown in various areas of China.

Topics: Acyclic Monoterpenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexane Monoterpenes; Cymenes; Eleutherococcus; Gas Chromatography-Mass Spectrometry; Monoterpenes; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes

This article reports the chemical components identified in the essential oil from the leaf and stem barks of Polyalthia harmandii (Pierre) Fin. and Gagnep., Polyalthia jucunda (Pierre) Fin. and Gagnep. and Polyalthia thorelii (Pierre) Fin. and Gagnep. The compounds identified in all the samples were α-pinene (0.2-3.2%), myrcene (0.3-4.1%), (E)-β-ocimene (0.2-9.6%), bicycloelemene (0.2-18.0%), β-elemene (0.3-4.9%), β-caryophyllene (0.1-17.8%), germacrene D (4.4-20.1%), bicyclogermacrene (4.2-27.9%) and δ-cadinene (0.2-4.5%). Besides, benzyl benzoate (9.7%) and ishwarane (8.0%), respectively, were the other prominent compounds in the leaf and stem of P. harmandii. In addition, δ-3-carene (8.2%), α-amorphene (6.5%), β-phellandrene (5.5%) and β-pinene (5.1%) were identified in P. jucunda leaf, while sabinene (30.9%) and β-phellandrene (10.2%) occurred largely in the stem. Moreover, γ-elemene (22.3% and 12.3%), germacrene D (10.5% and 6.9%) and spathulenol (9.1% and 11.8%) were identified in the leaf and stem of P. thorelii, while α-terpinene (7.8%) and β-gurjunene (5.2%) were identified only in the leaf oil.

Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexane Monoterpenes; Cyclohexenes; Cyclopropanes; Monoterpenes; Oils, Volatile; Plant Leaves; Plant Stems; Polyalthia; Polycyclic Sesquiterpenes; Sesquiterpenes; Vietnam

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 variation of the essential-oil composition among ten wild populations of Stachys lavandulifolia VAHL (Lamiaceae), collected from different geographical regions of Iran, was assessed by GC-FID and GC/MS analyses, and their intraspecific chemical variability was determined. Altogether, 49 compounds were identified in the oils, and a relatively high variation in their contents was found. The major compounds of the essential oils were myrcene (0.0-26.2%), limonene (0.0-24.5%), germacrene D (4.2-19.3%), bicyclogermacrene (1.6-18.0%), δ-cadinene (6.5-16.0%), pulegone (0.0-15.1%), (Z)-hex-3-enyl tiglate (0.0-15.1%), (E)-caryophyllene (0.0-12.9), α-zingiberene (0.2-12.2%), and spathulenol (1.6-11.1%). For the determination of the chemotypes and the chemical variability, the essential-oil components were subjected to cluster analysis (CA). The five different chemotypes characterized were Chemotype I (germacrene D/bicyclogermacrene), Chemotype II (germacrene D/spathulenol), Chemotype III (limonene/δ-cadinene), Chemotype IV (pulegone), and Chemotype V (α-zingiberene). The high chemical variation among the populations according to their geographical and bioclimatic distribution imposes that conservation strategies of populations should be made appropriately, taking into account these factors. The in situ and ex situ conservation strategies should concern all populations representing the different chemotypes.

Topics: Acyclic Monoterpenes; Alkenes; Cyclohexane Monoterpenes; Cyclohexenes; Gas Chromatography-Mass Spectrometry; Iran; Limonene; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Stachys; Terpenes

The essential oils obtained by hydrodistillation from the leaves of Tabernaemontana catharinensis had their composition analysed by GC-MS. A total of 18 substances were identified, consisting of a complex mixture of sesquiterpenes (83.52%), monoterpenes (5.46%) and triterpenes (4.56%). The main components in the oil were β-caryophyllene (56.87%), α-cadinol (12.52%), 8S,13-cedran-diol (5.41%), α-terpineol (3.99%), β-eudesmol (2.54%), caryophyllene oxide (2.51%) and ethyl iso-allocholate (2.03%) along with β-cubebene, γ-cadinene, cubenol, 1,8-cineol, o-cymene, curcumenol, spathulenol, friedeline and β-sitosterol as minor constituents. An antioxidant property was tested with the oil obtained by means of 1,1-diphenyl-2-picrylhydrazyl assay; the oil presented interesting radical scavenging activity. To the best of our knowledge, this is the first study of the composition and antioxidant activity of essential oil from the T. catharinensis collected from Brazil.

Topics: Antioxidants; Cyclohexane Monoterpenes; Cyclohexanols; Cyclohexenes; Eucalyptol; Monoterpenes; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Eudesmane; Sitosterols; Tabernaemontana; Terpenes

The objective of this study was to investigate in vitro antimicrobial activity and composition of the essential oil of Cyclotrichium leucotrichum growing wild in Iran. The essential oil was obtained by hydro-distillation and analysed by GC-FID and GC/MS. Fifty-nine components representing 98.9% of the total oil were characterised. The essential oil which has 1,8-cineol (14.8%), elemol (12.6%), spathulenol (9.4%), E-caryophyllene (5.7%) and hinesol (5.7%) as its main components, exhibited moderate activity against seven bacteria and a yeast, Candida albicans, with minimum inhibitory concentration values ranging from 0.5 to 64 mg mL(-1) and minimum bactericidal concentration values ranging from 2 to >64 mg mL(-1), respectively. The best inhibitory effects were against three gram-positive bacteria and tested yeast, C. albicans.

Topics: Anti-Infective Agents; Candida albicans; Iran; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Spiro Compounds

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

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