caryophyllene-oxide and carvacrol

In this study, the essential oil composition of

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

Micromeria persica Boiss. is medicinal and aromatic plant, belonging to the Lamiaceae family. The chemical composition of the essential oils (EOs) from aerial parts of M. persica were extracted using hydro-distillation method and analysed using GC and GC-MS. Fifty-two compounds were identified in the EOs of aerial parts of M. persica. The main chemical compositions were n-hexadecanoic acid (14.9%), thymol (9.5%), linoleic acid (8.0%), carvacrol (5.6%), (E)-nerolidol (5.5%), linolenic acid (5.5%), α-cadinol (2.7%), linalool (2.7%), borneol (2.6%), caryophyllene oxide (2.3%) and pulegone (2.0%). Presence of borneol, thymol, carvacrol and pulegone suggests the potential of this plant as a flavouring source in the food industry, being used in perfumery and cosmetics industry, vitamin E synthesis and exhibit strong fungicidal, antibacterial and antimicrobial activities.

Topics: Acyclic Monoterpenes; Camphanes; Cyclohexane Monoterpenes; Cymenes; Gas Chromatography-Mass Spectrometry; Iran; Lamiaceae; Monoterpenes; Oils, Volatile; Plant Components, Aerial; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Thymol

The antileishmanial activity of the essential oil (EO) from Chenopodium ambrosioides L. has been demonstrated in vitro and in animal models, attributed to the major components of the EO. This study focused on the effects of the three major EO compounds carvacrol, caryophyllene oxide (Caryo), and the antileishmanial endoperoxide ascaridole (Asc) on mitochondrial functions in Leishmania tarentolae promastigotes (LtP). EO and Caryo were able to partially inhibit the leishmanial electron transport chain, whereas other components failed to demonstrate a direct immediate effect. Caryo demonstrated inhibition of complex III activity in LtP and in isolated complex III from other species. The formation of superoxide radicals was studied in Leishmania by electron spin resonance spectroscopy in the presence of iron chelators wherein selected compounds failed to trigger a significant immediate additional superoxide production in LtP. However, upon prolonged incubation of Leishmania with Asc and especially in the absence of iron chelators (allowing the activation of Asc), an increased superoxide radical production and significant impairment of mitochondrial coupling in Leishmania was observed. Prolonged incubation with all EO components resulted in thiol depletion. Taken together, the major components of EO mediate their leishmanicidal activity via different mitochondrial targets and time profiles. Further studies are required to elucidate possible synergistic effects of carvacrol and Asc and the influence of minor compounds.

Topics: Animals; Antiprotozoal Agents; Cattle; Chenopodium ambrosioides; Cyclohexane Monoterpenes; Cymenes; Leishmania; Mitochondria; Monoterpenes; Oils, Volatile; Peroxides; Polycyclic Sesquiterpenes; Saccharomyces cerevisiae; Sesquiterpenes; Superoxides

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

To date there are no vaccines against Leishmania and chemotherapy remains the mainstay for the control of leishmaniasis. The drugs currently used for leishmaniasis therapy are significantly toxic, expensive, and result in a growing frequency of refractory infections. In this study, we evaluated the effect of combinations of the main components of essential oil from Chenopodium ambrosioides (ascaridole, carvacrol, and caryophyllene oxide) against Leishmaniaamazonensis. Anti-leishmanial effects of combinations of pure compounds were evaluated in vitro and the fractional inhibitory concentration (FIC) indices were calculated. BALB/c mice infected with L. amazonensis were treated with different concentrations of ascaridole-carvacrol combinations by intralesional doses every 4 days. Disease progression and parasite burden in infected tissues were determined. In vitro experiments showed a synergistic effect of the combination of ascaridole-carvacrol against promastigotes of Leishmania with a FIC index of 0.171, while indifferent activities were observed for ascaridole-caryophyllene oxide (FIC index=3.613) and carvacrol-caryophyllene oxide (FIC index=2.356) combinations. The fixed ratio method showed that a 1:4 ascaridole-carvacrol ratio produced a better anti-protozoal activity on promastigotes, lower cytotoxicity, and synergistic activity on intracellular amastigotes (FIC index=0.416). Significant differences (p<0.05) in lesion size and parasite burden were demonstrated in BALB/c mice experimentally infected and treated with the ascaridole-carvacrol combinations compared with control animals. Carvacrol showed significant higher anti-radical activity in the DPPH assay compared with caryophyllene oxide. Electron spin resonance spectroscopy in combination with spin trapping suggested the presence of carbon-centered radicals after activation of ascaridole by Fe(2+). The intensity of the signals is preferably decreased upon addition of carvacrol. The ascaridole-carvacrol combination could represent a future alternative to monotherapeutic anti-leishmanial agents.

Topics: Animals; Antiprotozoal Agents; Chenopodium ambrosioides; Cyclohexane Monoterpenes; Cymenes; Drug Combinations; Drug Dosage Calculations; Leishmania; Leishmaniasis, Cutaneous; Mice; Mice, Inbred BALB C; Monoterpenes; Oils, Volatile; Peroxides; Phytotherapy; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes

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

Chenopodium ambrosioides have been used for centuries in the Americas as a popular remedy for parasitic diseases. The essential oil of this plant possesses anthelmintic activity and is still used in some regions to treat parasitosis and leishmaniasis. However, the Chenopodium oil caused also some fatalities, leading to its commercial disuse. In this work, we studied the mechanism of toxicity of the essential oil and its major pure ingredients (carvacrol, caryophyllene oxide, and ascaridole, which was synthesized from alpha-terpinene) with respect to mammalian cells and mitochondria. We observed that all products, but especially caryophyllene oxide, inhibited the mitochondrial electron transport chain. This effect for carvacrol and caryophyllene oxide was mediated via direct complex I inhibition. Without Fe2+, ascaridole was less toxic to mammalian mitochondria than other major ingredients. However, evidence on the formation of carbon-centered radicals in the presence of Fe2+ was obtained by ESR spin-trapping. Furthermore, it was shown that Fe2+ potentiated the toxicity of ascaridole on oxidative phosphorylation of rat liver mitochondria. The increase of the alpha-tocopherol quinone/alpha-tocopherol ratio under these conditions indicated the initiation of lipid peroxidation by Fe2+-mediated ascaridole cleavage. Further ESR spin-trapping experiments demonstrated that in addition to Fe2+, reduced hemin, but not mitochondrial cytochrome c can activate ascaridole, explaining why ascaridole in peritoneal macrophages from BALB/c mice exhibited a higher toxicity than in isolated mitochondria.

Topics: Animals; Chenopodium ambrosioides; Cyclohexane Monoterpenes; Cymenes; Electron Spin Resonance Spectroscopy; Lipid Peroxidation; Magnetic Resonance Spectroscopy; Male; Mice; Mice, Inbred BALB C; Mitochondria, Liver; Monoterpenes; Oils, Volatile; Oxidative Phosphorylation; Peroxides; Polycyclic Sesquiterpenes; Rats; Rats, Sprague-Dawley; Sesquiterpenes