bisabolol and alpha-pinene

Leucas aspera (Willd.) Link (Lamiaceae) is an annual, branched herb used in traditional medicine as an antipyretic and insecticide. The hydro-distilled essential oil was obtained from the aerial parts of L. aspera growing wild in North West Karnataka region of India and analyzed by gas chromatography equipped with flame ionization detector and gas chromatography coupled with mass spectrometry. Forty-three compounds were identified, representing 98.1% of the total oil. The main constituents were identified as β-caryophyllene (34.2%), 1-octen-3-ol (14.8%), α-humulene (6.3%), α-pinene (5.8%), epi-α-bisabolol (4.6%) and limonene (4.5%). The oil was found to be rich in sesquiterpene hydrocarbons (47.7%), followed by others (long chain hydrocarbons (LCH), oxygenated LCH and phenyl derivative constituents) (20.2%), monoterpene hydrocarbons (14.8%), oxygenated sesquiterpenes (14.8%) and oxygenated monoterpenes (0.6%) type compounds.

Topics: Bicyclic Monoterpenes; Cyclohexenes; Gas Chromatography-Mass Spectrometry; India; Lamiaceae; Limonene; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Components, Aerial; Plant Extracts; Sesquiterpenes; Solvents; Terpenes; Water

The aim of this study was to evaluate the antimycobacterial activity of the essential oil (EO) of Mutellina purpurea L. and its main constituents against the M. tuberculosis H37Ra strain.. The M. purpurea EO was obtained by hydrodistillation, while its main constituents were purchased. The minimal inhibitory concentration values were determined by the log2 dilution method. Visualization of the effects of the tested substances on M. tuberculosis was performed using a transmission electron microscope (TEM). Mathematical shape descriptors such as area, circularity, aspect ratio and roundness were calculated to describe morphological changes in bacterial cell shape.. The EO of M.purpurea and all substances tested in this experiment showed a significant antimycobacterial activity. The most active was α-pinene followed by bisabolol and myrcene (8, 16 and 32 µg/ml, respectively). The EO and limonene exhibited the same antimicrobial activity (64 µg/ml). The TEM images and shape descriptors showed significant changes in the overall tuberculosis cell shape and cytoplasm homogeneity (uniformity and consistency). In this study, the low molecular weight compounds of mono- and sesquiterpenes penetrated/destabilized the complex mycobacterial cell wall and decreased its viability. There is a need for further experiments to explain the mechanism of action of these small particles.

Topics: Anti-Bacterial Agents; Apiaceae; Bicyclic Monoterpenes; Cell Shape; Cyclohexenes; Cytoplasm; Dose-Response Relationship, Drug; Humans; Limonene; Microbial Sensitivity Tests; Microscopy, Electron, Transmission; Monocyclic Sesquiterpenes; Monoterpenes; Mycobacterium tuberculosis; Oils, Volatile; Sesquiterpenes; Terpenes

The chemical composition of the essential oils obtained by hydrodistillation from the pastinocello carrot, Daucus carota ssp. major (Vis.) Arcang. (flowers and achenes), and from nine different commercial varieties of D. carota L. ssp. sativus (achenes) was investigated by GC/MS analyses. Selective breeding over centuries of a naturally occurring subspecies of the wild carrot, D. carota L. ssp. sativus, has produced the common garden vegetable with reduced bitterness, increased sweetness, and minimized woody core. On the other hand, the cultivation of the pastinocello carrot has been abandoned, even if, recently, there has been renewed interest in the development of this species, which risks genetic erosion. The cultivated carrot (D. carota ssp. sativus) and the pastinocello carrot (D. carota ssp. major) were classified as different subspecies of the same species. This close relationship between the two subspecies urged us to compare the chemical composition of their essential oils, to evaluate the differences. The main essential-oil constituents isolated from the pastinocello fruits were geranyl acetate (34.2%), α-pinene (12.9%), geraniol (6.9%), myrcene (4.7%), epi-α-bisabolol (4.5%), sabinene (3.3%), and limonene (3.0%). The fruit essential oils of the nine commercial varieties of D. carota ssp. sativus were very different from that of pastinocello, as also confirmed by multivariate statistical analyses.

Topics: Acetates; Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Cluster Analysis; Cyclohexenes; Daucus carota; Flowers; Fruit; Gas Chromatography-Mass Spectrometry; Limonene; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Principal Component Analysis; Sesquiterpenes; Terpenes

In the current investigation, the influence of the plant growth stages (prior to emergence of flower heads or vegetative, anthesis and fruiting) on the essential oil content and composition in the aerial parts of Prangos uloptera DC. was studied. Quantitative and qualitative differences were found among oil of aerial parts at three phenological stages. The principle compounds of the oil before emergence of flower heads were saferole (21.6%) and α-pinene (20%), while the oil at anthesis was composed of α-bisabolol (30.5%), saferole (19.11%) and (+)-spathulenol (12.9%). The oil at fruiting stage displayed γ-terpinene (35.5%) and trans-anethole (23.5%) as major constituents. These findings may confer valuable information regarding chemical composition of P. uloptera DC., which could be beneficial in the fields of herbal medicine.

Topics: Allylbenzene Derivatives; Anisoles; Apiaceae; Bicyclic Monoterpenes; Cyclohexane Monoterpenes; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Components, Aerial; Plant Oils; Plants, Medicinal; Safrole; Sesquiterpenes

The analysis of the essential oil from rhizome and roots of Ferula hermonis Boiss. (Apiaceae) by GC-FID, GC-MS and ¹³C NMR allowed the identification of 79 constituents, more than 90% of the oil, the major one being α-pinene (43.3%), followed by α-bisabolol (11.1%) and the unusual acetylenic compound 3,5-nonadiyne (4.4%). The antifungal activity of the essential oil before and after fractionation was assayed against several yeasts and filamentous fungi. Purification of the active fractions afforded 3,5-nonadiyne, α-bisabolol, jaeschkeanadiol angelate, α-bisabolol oxide B and trans-verbenol, as well as two purified fractions, one of them (JB73) with 73% of jaeschkeanadiol benzoate and the other with 50% of spathulenol. Determination of MIC and MFC values of all these products evidenced strong antifungal activities for JB73 and 3,5-nonadiyne. Particularly, against the dermatophyte Tricophyton mentagrophytes, MIC and MFC values were 0.25 μg/ml for JB73, and 8 μg/ml for 3,5-nonadiyne, the former being more active than amphotericin B and nystatin.

Topics: Alkynes; Antifungal Agents; Bicyclic Monoterpenes; Chemical Fractionation; Ferula; Fungi; Microbial Sensitivity Tests; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Plant Roots; Rhizome; Sesquiterpenes

A study on the volatile oil of Ferula behboudiana by gas chromatography and gas chromatography-mass spectrometry showed the presence of 27 compounds. Two disulphide derivatives, 1-sec-butyl-2-[(E)-3-(methylthio) prop-1-enyl] disulphane (1) and 1-sec-butyl-2-[(Z)-3-(methylthio)prop-1-enyl] disulphane (2) (59.4%), were isolated from the oil by thin layer chromatography and their structures were elucidated by spectroscopic techniques. Glubolol (12.5%), α-pinene (8.8%), α-bisabolol (6.1%) and β-pinene (3.9%) were the other major compounds.

Topics: Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Chromatography, Gas; Chromatography, Thin Layer; Disulfides; Ferula; Gas Chromatography-Mass Spectrometry; Molecular Structure; Monocyclic Sesquiterpenes; Monoterpenes; Oils, Volatile; Sesquiterpenes