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Chemical composition and antimicrobial activity of the essential oils of Anthemis xylopoda O. Schwarz from Turkey.

The chemical composition and the antimicrobial activity of the essential oils isolated from the leaves (LEO) and flowers (FEO) of Anthemis xylopoda, an endemic taxon of Turkey, were investigated. Borneol was the major constituent of both the oils studied (30.15 and 31.85%, respectively). The antimicrobial activities of both oils were separately evaluated against 13 microorganisms. The disc diffusion method was used for the antimicrobial activity test. Results showed that both oils of Anthemis xylopoda exhibited a significant antimicrobial activity.

Anthemis↗

A new flavonoid: tinctosid from Anthemis tinctoria L.

Patuletin 7-O-beta-D-(6"-caffeoylglucoside) was isolated from the methanolic extract of the flowers of Anthemis tinctoria L. (Asteraceae). The isolated compound was identified by spectroscopic means and by comparison with authentic samples after enzymatic hydrolysis. A new flavonoid glycoside, tinctosid, from Anthemis tinctoria L. was isolated from a plant source for the first time.

Anthemis↗

Analysis of the essential oil composition of eight Anthemis species from Greece.

The volatile composition of eight Anthemis species has been studied. The essential oils were obtained by hydrodistillation in a modified Clevenger-type apparatus, and their analyses were performed by GC and GC-MS. Identification of the substances was made by comparison of mass spectra and retention indices with literature records. A total of 284 different compounds were identified and significant qualitative and quantitative differences and similarities were observed among the samples. The main constituents of the investigated populations of each taxon have been revealed as follows: A. altissima: (-)-linalool, trans-caryophyllene, cis-chrysanthenyl acetate; A. auriculata: spathulenol, trans-caryophyllene, beta-eudesmol; A. chia: cis-chrysanthenyl acetate, trans-caryophyllene, germacrene-d; A. cotula: germacrene-d, spathulenol A. tinctoria: spathulenol, (-)-caryophyllene oxide, T-cadinol; A. melanolepis: p-cymene, chrysanthenone, trans-verbenol, (-)-caryophyllene oxide; A. tomentosa: (-)-linalool, 1,8-cineole; A. werneri subsp. werneri: nopol, terpineol-4, trans-caryophyllene. Sesquiterpene hydrocarbons were shown to be the main group of constituents of all taxa.

Anthemis↗

Linear sesquiterpene lactones from Anthemis auriculata and their antibacterial activity.

Three linear sesquiterpene lactones, anthecotulide (1), hydroxyanthecotulide (2), and acetoxyanthecotulide (3), were isolated from the aerial parts of Anthemis auriculata. Five known flavonoids, taraxa-20(30)en-3beta-ol (4), and methyl vanillate (5) were also isolated. The structures and the relative configuration of the new compounds 2 and 3 were deduced by spectroscopic methods. The in vitro activity of compounds 1-5 against 10 bacterial species and one fungus was tested using the microdilution method.

Anthemis↗

Biosynthesis of anthecotuloide, an irregular sesquiterpene lactone from Anthemis cotula L. (Asteraceae) via a non-farnesyl diphosphate route.

Retrobiosynthetic analysis of the allergenic sesquiterpene lactone, anthecotuloide, suggested that this natural product could be formed either by head to head condensation of geranyl diphosphate with dimethylallyl diphosphate, or from farnesyl diphosphate (FPP), the accepted regular sesquiterpene precursor via the rearrangement of a germacranolide precursor. Isotopic labelling of anthecotuloide has now been achieved by feeding [1-(13)C]-glucose, [U-13C6]-glucose and [6,6-(2)H2]-glucose to aseptically grown plantlets of Anthemis cotula(family Asteraceae). Analysis of labelling patterns and absolute 13C abundances using quantitative 13C NMR spectroscopy showed that the isoprene building blocks of this sesquiterpene are formed exclusively via the MEP terpene biosynthetic pathway. This was supported by results from an experiment using [U-13C6]-glucose. A deuterium labelling experiment using [6,6-(2)H2]-glucose supported the original proposal and showed that anthecotuloide is formed from a non FPP precursor. Isotope ratio mass spectrometry suggested that there were two pathways for sesquiterpene biosynthesis in A. cotula.

Anthemis↗

The essential oil constituents and antimicrobial activity of Anthemis aciphylla BOISS. var. discoidea BOISS.

The essential oil of aerial parts, leaves and flowers of the endemic Anthemis aciphylla BOISS. var. discoidea BOISS. (Asteraceae) were obtained by hydrodistillation. The oils were analyzed both by GC and GC-MS on a polar column. The monoterpenes alpha-pinene (9-49%) and terpinen-4-ol (22-32%) were characterized as the main constituents. An unknown component isolated from the essential oil was characterized by means of MS, HR-MS, FT-IR, 1D- and 2D-NMR techniques as isofaurinone (1). Furthermore, the biological activity of the essential oils was evaluated in various human pathogenic microorganisms using the broth microdilution method. Weak to moderate inhibitions (0.06-1.0 mg/ml) was observed.

Anthemis↗

Sesquiterpene lactones from Anthemis carpatica Willd.

Four new eudesmanolides and two new guaianolides were isolated from the aerial parts of Anthemis carpatica Willd. and their structures elucidated by spectral methods. In addition, seven known sesquiterpene lactones were identified.

Anthemis↗

Chemical composition and biological activity of the volatiles of Anthemis melampodina and Pluchea dioscoridis.

The volatile fractions obtained by hydrodistillation of the fresh leaves of Anthemis melampodina and Pluchea dioscoridis were analysed by GC-MS technique. Of 38 components identified in the volatile oil of A. melampodina, santolinatriene was the major component (27.33%). The oil was characterized by a high percentage of monoterpene hydrocarbons (49.94%) while sesquiterpene hydrocarbons and oxygenated sesquiterpenes represented only 7.41% and 11.43% of the oil. 36 components were identified in the volatile oil of P. dioscoridis. Farnesol was the major component (16.50%) accompanied by a high percentage of sesquiterpene alcohols. Oxygenated sesquiterpenes (26.43%) and sesquiterpene hydrocarbons (39.43%) represented the main constituents in the oil. P. dioscoridis showed a marked mosquito larvicidal activity against Culex pipiens (LC(50) 71.86 ppm), while A. melampodina was moderately active (LC(50) 139.42 ppm).

Animals↗

Sedative, anti-inflammatory and anti-diuretic effects induced in rats by essential oils of varieties of Anthemis nobilis: a comparative study.

The pharmacological properties of essential oils obtained from two varieties of Anthemis nobilis was studied. The two varieties, named "white-headed" or double flowered and "yellow-headed", present considerable morphological differences and yield essential oils with different composition. These essential oils proved to possess interesting anti-inflammatory and sedative properties, especially that derived from the "White-headed" variety.

Animals↗

Further sesquiterpene lactones from Anthemis carpatica.

A new germacranolide, (E)-1alpha, 10beta-epoxy-3beta-acetoxy-6alpha-hydroxygermacra-4,11 (13)-dien-12,8alpha-olide, together with nine new highly oxygenated guaiadien-12,6alpha-olides of anthemolide, and cumambrin type were identified in the repeated examination of the aerial parts of the flowering Anthemis carpatica. In addition, six known guaianolides belonging to the same groups, also isolated previously from A. carpatica, along with two guaianolides, 2beta-hydroxyepiligustrin and cumambrin B, not found before in this species, were isolated this time.

Asteraceae↗

Antimicrobial activity of flowers from Anthemis cotula.

The flavonoid containing total extract of Anthemis cotula flowers, tested at the concentration of 200 microg/ml, showed interesting antimicrobial activity against both Gram-negative and Gram-positive microorganisms.

Anti-Bacterial Agents↗

Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity.

Seven sesquiterpene lactones, (-) sivasinolide (1), a new naturally occurring eudesmanolide (altissin, 2), desacetyl-beta-cyclopyrethrosin (3), tatridin-A (4), 1-epi-tatridin B (5), 1alpha,10beta-epoxy-6-hydroxy-1,10H-inunolide (6), and spiciformin (7), were isolated from Anthemis altissima. Also isolated were 10 known flavonoids, namely, apigenin (8), kaempferol 4'-methyl ether (9), quercetin (10), quercetin 3-methyl ether (11), isorhamnetin (12), rhamnetin (13), 6-hydroxyquercetin 3,6,4'-trimethyl ether (14), isoquercetrin (15), taxifolin (16), and eriodictyol (17), and one phenolic acid, chlorogenic acid (18). The structure and the stereochemistry of compound 2 were deduced by spectroscopic methods. The in vitro activity of the sesquiterpene lactones (1-5) against Helicobacter pylori, as well as against three Gram-positive and three Gram-negative bacteria growing aerobically, was tested using the microdilution method. Compounds 8-18 have also been tested against H. pylori.

Asteraceae↗

Terpenoids from Anthemis austriaca Jacq.

The aerial parts of Anthemis austriaca Jacq. afforded five new sesquiterpene lactones (two of which are dimeric guaianolides) and three new guaiane type sesquiterpene acids In addition, seven known terpenoids were also found in the studied species. Their structures were elucidated by spectral methods.

Asteraceae↗

Antibacterial activity of crude methanolic extract and its fractions of aerial parts of Anthemis tinctoria.

The antibacterial activity of the methanolic extract and its fractions of aerial parts of Aniheinis tinctoria (Asteraceae) was investigated against representative gram-positive Staphylococcus aureus (ATCC 25923) and Enterococcus faecalis (ATCC 29212) and gram-negative strains Escherichia coli (ATCC 25922) and Pseudomonas aeruginosa (ATCC 27853). The activity was concentrated mainly in the dichloromethane (DCM) and hexane fractions of crude methanolic extract. The 5 mg of DCM extract per disk produced 15-16 mm of inhibition zone against S. aureus and P. aeruginosa, however, no activity was found against E. faecalis and E. coli. The hexane fraction showed activity against S. aureus, P. aeruginosa and E. faecalis. As DCM fraction showed the highest antibacterial activity in the disk diffusion assay, the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of only this fraction was determined against S. aureus and P. aeruginosa. These values were found to be in the range of 1.25 to 10 mg/ml.

Anthemis↗