germacrene-d and beta-ocimene

Annona vepretorum Mart. (Annonaceae), popularly known as 'bruteira', has nutritional and medicinal uses. This study investigated the chemical composition and antitumour potential of the essential oil of A. vepretorum leaf alone and complexed with β-cyclodextrin in a microencapsulation. The essential oil was obtained by hydrodistillation using a Clevenger-type apparatus and analysed using GC-MS and GC-FID. In vitro cytotoxicity of the essential oil and some of its major constituents in tumour cell lines from different histotypes was evaluated using the alamar blue assay. Furthermore, the in vivo efficacy of essential oil was demonstrated in mice inoculated with B16-F10 mouse melanoma. The essential oil included bicyclogermacrene (35.71%), spathulenol (18.89%), (E)-β-ocimene (12.46%), α-phellandrene (8.08%), o-cymene (6.24%), germacrene D (3.27%) and α-pinene (2.18%) as major constituents. The essential oil and spathulenol exhibited promising cytotoxicity. In vivo tumour growth was inhibited by the treatment with the essential oil (inhibition of 34.46%). Importantly, microencapsulation of the essential oil increased in vivo tumour growth inhibition (inhibition of 62.66%).

Topics: Acyclic Monoterpenes; Adult; Alkenes; Animals; Annona; Antineoplastic Agents, Phytogenic; beta-Cyclodextrins; Bicyclic Monoterpenes; Cell Line, Tumor; Cyclohexane Monoterpenes; Cyclohexanones; Disease Models, Animal; Drug Compounding; Gas Chromatography-Mass Spectrometry; Hep G2 Cells; Humans; Inhibitory Concentration 50; Male; Melanoma, Experimental; Mice; Mice, Inbred C57BL; Monoterpenes; Oils, Volatile; Plant Leaves; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes; Young Adult

This investigation focused on the qualitative and quantitative composition of essential oil compounds of European Origanum vulgare. Extracts of 502 individual O. vulgare plants from 17 countries and 51 populations were analyzed via GC. Extracts of 49 plants of 5 populations of Israeli Origanum syriacum and 30 plants from 3 populations of Turkish Origanum onites were included to exemplify essential oil characteristics of 'high-quality' oregano. The content of essential oil compounds of European O. vulgare ranged between 0.03% and 4.6%. The monoterpenes were primarily made up of sabinene, myrcene, p-cymene, 1,8-cineole, β-ocimene, γ-terpinene, sabinene hydrate, linalool, α-terpineol, carvacrol methyl ether, linalyl acetate, thymol and carvacrol. Among the sesquiterpenes β-caryophyllene, germacrene D, germacrene D-4-ol, spathulenol, caryophyllene oxide and oplopanone were often present in higher amounts. According to the proportions of cymyl-compounds, sabinyl-compounds and the acyclic linalool/linalyl acetate three different main monoterpene chemotypes were defined. The cymyl- and the acyclic pathway were usually active in plants from the Mediterranean climate whereas an active sabinyl-pathway was a characteristic of plants from the Continental climate.

Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Cyclohexane Monoterpenes; Cyclohexanols; Cyclohexenes; Cymenes; Eucalyptol; Europe; Monoterpenes; Oils, Volatile; Origanum; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Thymol

The chemical constituents of essential oils from the leaf, stem bark and resins of Canarium parvum Leen., and Canarium tramdenanum Dai et Yakovl. (Burseracea) grown in Vietnam are being reported. The hydrodistilled oils were analysed for their chemical constituents by means of gas chromatography-flame ionisation detector and gas chromatography coupled with mass spectrometry. The main compounds of C. parvum were β-caryophyllene (18.7%), (E)-β-ocimene (12.9%), (Z)-β-ocimene (11.9%), germacrene D (8.8%) and α-humulene (8.4%) in the leaf; β-caryophyllene (30.4%), α-copaene (20.5%) and (E)-β-ocimene (7.7%) in the stem. However, germacrene D (23.2%), α-amorphene (14.9%), α-copaene (9.8%) and β-elemene (8.6%) were present in the resin. The leaf of C. tramdenanum comprises β-caryophyllene (16.8%), α-phellandrene (15.9%), γ-elemene (13.1%) and limonene (11.8%), while limonene (25.7%), α-phellandrene (21.7%), α-pinene (12.3%) and β-caryophyllene (10.9%) were present in the stem. However, δ-elemene (14.6%) and bulnesol (16.0%) are the main constituents in the resin.

Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Burseraceae; Cyclohexane Monoterpenes; Cyclohexenes; Gas Chromatography-Mass Spectrometry; Limonene; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Leaves; Plant Oils; Plant Stems; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Terpenes; Vietnam

Essential oils from leaves of Xylopia frutescens (XFMJ) and two specimens of Xylopia laevigata (XLMC and XLSI) were obtained by hydrodistillation using a Clevenger-type apparatus, and analyzed by GC-MS and GC-FID. Sesquiterpenes dominated the essential oils. The main constituents of XFMJ were (E)-caryophyllene (24.8%), bicyclogermacrene (20.8%), germacrene D (17.0%), beta-elemene (7.9%), and (E)-beta-ocimene (6.8%). XLMC contained significant quantities of germacrene D (18.9%), bicyclogermacrene (18.4%), beta-elemene (9.5%), delta-selinene (9.2%), (E)-caryophyllene (8.5%), germacrene B (5.7%) and gamma-muurolene (5.7%), while germacrene D (27.0%), bicyclogermacrene (12.8%), (E)-caryophyllene (8.6%), gamma-muurolene (8.6%), delta-cadinene (6.8%), and germacrene B (6.0%) were the main components of XLSI. The essential oils had trypanocidal activity against the Y strain of Trypanosoma cruzi, with IC50 values lower than 30 microg x mL(-1) and 15 microg x mL(-1) against epimastigote and trypomastigote forms of T. cruzi, respectively, and were also able to reduce the percentage in vitro of T. cruzi-infected macrophages and the intracellular number of amastigotes at concentrations that were non-cytotoxic to macrophages.

Topics: Acyclic Monoterpenes; Alkenes; Oils, Volatile; Plant Leaves; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Germacrane; Trypanocidal Agents; Trypanosoma cruzi; Xylopia