caryophyllene-oxide and 1-1-diphenyl-2-picrylhydrazyl

The essential oil extracted from Desfontaine's rupturewort, Herniaria fontanesii J. Gay subsp. fontanesii growing wildly in Tunisia, was analyzed using GC and GC-MS techniques. The free radical scavenging capacity and total phenol contents of three crude extracts having different polarities (n-hexane, ethyl acetate and methanol) were examined. Thus, a total of 35 constituents were identified in the Desfontaine's rupturewort essential oil representing 89.8% of the whole constituents. The oil was dominated by hexadecanoic acid, caryophyllene oxide, terpin-4-ol, khusimone and trans-sabinene hydrate. The total phenolic contents ranged from 16.91 to 92.27 mg of gallic acid/g of dry weight and they were found to be significantly higher in methanol than in polar ethyl acetate and hexane extracts. Correlations were observed between the phenolic contents and the antioxidant properties. Thus, the antioxidant activity of the methanol extract was superior to that of all samples tested (IC50 = 0.21 ± 0.04 mg/mL).

Topics: Acetates; Bicyclic Monoterpenes; Biphenyl Compounds; Caryophyllaceae; Free Radical Scavengers; Gallic Acid; Gas Chromatography-Mass Spectrometry; Hexanes; Methanol; Monoterpenes; Oils, Volatile; Palmitic Acid; Picrates; Plant Components, Aerial; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes; Solvents; Terpenes; Tunisia

The essential oil composition of the aerial parts of Nepeta erecta Benth. (Family: Lamiaceae) from Uttarakhand, India was analysed by capillary gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 34 constituents were identified representing 94.6% of the oil composition. Oxygenated monoterpenes (74.0%) constituted the major proportion of the oil, dominated by isoiridomyrmecin (70.6%) as a single major constituent. Other significant constituents were caryophyllene oxide (9.6%), β-Bourbonene (2.0%), humulene epoxide II (1.7%) and linalool (1.0%). The in vitro antioxidant activity (AOA) was assessed using β-Carotene bleaching assay, reducing power, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and inhibition of lipid peroxidation methods. The oil was found to exhibit AOA by inhibiting β-Carotene bleaching (54.6 ± 2.52%) and by scavenging DPPH free radical (IC(50) = 0.74 ± 0.12 mg mL(-1)). The AOA of the essential oil of N. erecta and its major compound isoiridomyrmecin has not been reported so far.

Topics: Acyclic Monoterpenes; Antioxidants; Biphenyl Compounds; Chromatography, Gas; Gas Chromatography-Mass Spectrometry; India; Iridoids; Molecular Structure; Monoterpenes; Nepeta; Oils, Volatile; Picrates; Polycyclic Sesquiterpenes; Sesquiterpenes

GC-MS analyses of the essential oils of leaves, stems and flower of Nasturtium officinale resulted in the identification of 9, 8 and 15 compounds, representing 97%, 100% and 94.7% of the oils, respectively. The main compounds of the oil of leaves were myristicin (57.6%), α-terpinolene (8.9%) and limonene (6.7%). Caryophyllene oxide (37.2%), p-cymene-8-ol (17.6%), α-terpinolene (15.2%) and limonene (11.8%) were the main components in stems, whereas limonene (43.6%), α-terpinolene (19.7%), p-cymene-8-ol (7.6%) and caryophyllene oxide (6.7%) were the major constituents in the oil of flowers. All the samples were subjected to a screening for their possible antioxidant activities using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and β-carotene-linoleic acid assays. In the above tests, methanol extracts of leaves showed higher antioxidant activity than the oils and methanol extracts of stems and flowers.

Topics: Allylbenzene Derivatives; Antioxidants; Benzyl Compounds; Biphenyl Compounds; Cyclohexenes; Cymenes; Dioxolanes; Flavonoids; Flowers; Gas Chromatography-Mass Spectrometry; Iran; Limonene; Methanol; Monoterpenes; Nasturtium; Oils, Volatile; Phenols; Picrates; Plant Leaves; Plant Stems; Polycyclic Sesquiterpenes; Pyrogallol; Sesquiterpenes; Terpenes

Citrus aurantium leaves' essential oils (EOs) were evaluated for chemical composition and antioxidant and antibacterial activities. The vegetable material, taken 5 times during the year, has undergone the hydrodistillation to prepare EO. Chemical characterization by gas chromatography/mass spectrometry and GC/flame ionization detection allowed the identification of 46 compounds, and a notable quantitative and qualitative differences between the different Petitgrain samples according to the harvest time. Linalool (43.2% to 65.97%), linalyl acetate (0.77% to 24.77%), and α-terpineol (9.29% to 12.12%) were the main components. The most important number of components was registered for summer EOs (July and September). The 5 EOs submitted biological activities screening, namely, antioxidant and antimicrobial activities. Weak antioxidant activities (IC(50) values >10000 mg/L) were registered by both 1,1-diphenyl-2-picrylhydrazyl and 2,2'-azinobis-3-ethylbenzothiazoline-6-sulphonate assays, mostly because the weak amount of phenols in EOs. Antibacterial activities (12 microorganisms) were registered against Gram-positive bacteria [Bacillus subtilis (MIC = 2.7 mg/mL), Staphylococcus aureus (4.8 mg/mL)], and moderated ones against yeasts [Saccharomyces cerevisiae (9.2 mg/mL)] and fungi [Mucor ramannianus (5 mg/mL)]. Positive correlations between the identified compounds and the antimicrobial activities were noted. Many compounds were correlated to antimicrobial activity mainly caryophyllene oxide against Escherichia coli (R(2) = 0.99), S. cerevisiae (R(2) = 0.99), and Fusarium culmorum (R(2) = 0.99).

Topics: Acyclic Monoterpenes; Anti-Infective Agents; Antioxidants; Bacillus subtilis; Biphenyl Compounds; Citrus; Cyclohexane Monoterpenes; Cyclohexenes; Escherichia coli; Flame Ionization; Food Contamination; Food Microbiology; Fusarium; Gas Chromatography-Mass Spectrometry; Microbial Sensitivity Tests; Monoterpenes; Mucor; Oils, Volatile; Picrates; Plant Leaves; Polycyclic Sesquiterpenes; Saccharomyces cerevisiae; Seasons; Sesquiterpenes; Staphylococcus aureus

Incubation of alpha-cedrol and caryophyllene oxide with Neurospora crassa afforded 12beta-hydroxy cedrol, 10alpha-hydroxy cedrol, and 3beta-hydroxy cedrol, and 12beta-hydroxy caryophyllene oxide as major metabolites, respectively. The antibacterial and radical scavenging activities of the metabolites were evaluated in vitro using broth microdilution and bioauthographic techniques. However, no significant antibacterial and antioxidant activities were observed when compared with those of standard substances.

Topics: Anti-Bacterial Agents; Biotransformation; Biphenyl Compounds; Free Radical Scavengers; Microbial Sensitivity Tests; Neurospora crassa; Picrates; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes