Novel acetylated chalcone and biflavonoid glycosides from Trigonosciadium brachytaenium (Boiss.) Alava.

A new acetylated chalcone glycoside, trans-2',6'-dihydroxy-4'-O-(4″-acetyl-rhamnoside)-4-methoxychalcone (1) and a new biflavonoid glycosides, 5,3',5″,4″'-tetrahydroxy-3″',5″'dimethoxy-biflavone (4' → 8″)-7-O-((2-rhamnoside) rhamnoside) (2) were isolated from the ethyl acetate soluble fraction of the methanol extract obtained from Trigonosciadium brachytaenium and have been purified by column chromatography and preparative TLC. Those structures were elucidated by UV, (1)H NMR and (13)C NMR, HMBC, EI-MS and IR spectra. The antioxidant activity of ethyl acetate extract was evaluated by 1,1-diphenyl-2-picrylhydrazyl method. The results indicate that ethyl acetate extract from aerial part of T. brachytaenium possesses considerable antioxidant activity.

Constituents and antimicrobial activity of the essential oils from flower, leaf and stem of Helichrysum armenium.

The chemical constituents from the flower, leaf and stem of Helichrysum armenium DC. (Asteraceae) growing in Iran were obtained by hydrodistillation and analyzed by GC and GC/MS. The oil of flower was characterized by higher amount of limonene (21.2%), alpha-cadinol (18.2%), borneol (11.9%), delta-cadinene (9.0%), bornyl acetate (8.0%) and alpha-humulene (7.3%). Twenty one constituents representing 96.2% of the chromatographical leaf oil were identified of which limonene (29.2%), alpha-pinene (14.4%), caryophyllene oxide (6.5%), alpha-gurjunene (6.3%), bornyl acetate (5.5%) and torreyol (5.2%) were the major components. The main components of the stem oil were limonene (23.6%), alpha-pinene (13.4%), spathulenol (6.4%), alpha-gurjunene (6.3%), caryophyllene oxide (5.3%), bornyl acetate (5.2%), beta-cubebene (4.8%) and delta-cadinene (4.3%). The composition of the oils is different, although the most abundant components are identical in leaf oil (96.2%). The antimicrobial effect of flower, leaf and stem essential oils from Helichrysum armenium was studied according to the agar diffusion cup method. The essential oils had a moderate effect on the Gram-positive and Gram-negative bacteria and had a substantial fungicidal effect on the fungi under study.

Antibacterial activity and GC/MS analysis of the essential oils from flower, leaf and stem of Origanum vulgare ssp. viride growing wild in north-west Iran.

Essential oils obtained from flowers, leaves and stems of Origanum vulgare L. ssp. viride (Boiss.) Hayek., growing wild in Ardabil Province (north-west Iran), were analyzed by GC and GC/MS. beta-Caryophyllene was the major constituent in all three oils (48.1%, 50.1% and 60.2%, respectively). Of the 19 components detected in the flower oil, comprising 96.3% of the total, the major components were 1,8-cineole (11.6%), alpha-pinene (6.9%), and gamma-cadinene (4.8%). 1-Octen-3-ol (23.8%), and 1,8-cineole (8.5%) predominated in the leafoil. In the stem oil, other main constituents were bicyclogermacrene (9.8%), 1,8-cineole (6.4%), borneol (5.1%), and pinocarvone (4.4%). The essential oils were evaluated for their antibacterial activity against 10 selected microorganisms. The data obtained contribute to the future use of certain essential oils as natural preservatives for food products, due to their safety and positive effect on shelf life.

Comparison of volatile constituents, and antioxidant and antibacterial activities of the essential oils of Thymus caucasicus, T. kotschyanus and T. vulgaris.

A comparison of the chemical composition, and antioxidant and antibacterial activities of the essential oils obtained from the aerial parts of Thymus caucasicus, T. kotschyanus, and T vulgaris was carried out. The oils, obtained by hydrodistillation, were analyzed by GC and GC/MS. Twenty, 29 and 22 compounds representing 94.8%, 96.6% and 98.2% of the essential oils of T. caucasicus, T. kotschyanus and T. vulgaris, respectively, have been identified. The oil of T. caucasicus was characterized by 1,8-cineol (21.5%), thymol (12.6%), beta-fenchyl alcohol (8.7%), nerolidol (7.8%), terpinolene (7.2%), alpha-pinene (7.0%) and myrcene (6.8%). In the oil of T. kotschyanus, carvacrol (24.4%), beta-caryophyllene (14.5%), gamma-terpinene (12.4%), alpha-phellandrene (10.8%), p-cymene (9.8%) and thymol (6.8%) were the predominant compounds, whereas the main components of T. vulgaris oil were thymol (43.8%), p-cymene (15.2%), germacrene-D (11.7%), terpinolene (3.4%), carvacrol (3.2%), beta-caryophyllene (2.8%) and alpha-thujene (2.2%). In all three plants oil, hydrocarbon monoterpenes predominated over sesquiterpenes. Antioxidant activities were assessed by determining IC50 values in the DPPH radical scavenging assay. Antibacterial activity was determined by measuring minimum inhibitory concentration (MIC) using the broth dilution method. The essential oils of T. caucasicus, T. kotschyanus and T. vulgaris showed free radical scavenging and antibacterial activity.

Antioxidant, antimicrobial activities and fatty acid components of flower, leaf, stem and seed of Hypericum scabrum.

The hexane extracts of flower, leaf, stem, and seed of Hypericum scabrum, which were collected from northwestern Iran, were obtained by extraction in a Soxhlet apparatus. The fatty acids were converted to methyl esters and determined by gas chromatography/flame ionization detector (GC/FID) and gas chromatography/mass spectrometry (GC/MS) systems. The hexane extract from the flower, leaf, stem, and seed contained 39.1%, 43.2%, 29.0%, and 37.6% of omega-3 fatty acids, respectively. The other main components of the flower extract were tetracosane (12.2%) and palmitic acid (9.3%), and that of the leaf extract was palmitic acid (7.4%). The stem and seed extracts contained bis(2-ethylhexyl)phthalate (18.7% and 35.7%), nonacosane (11.7% and 3.9%) and linoleic acid (6.5% and 6.9%) as major components. The hexane extracts of different parts from H. scabrum represent an important source of omega-3 fatty acids in several Hypericum species. The antioxidant activity of all hexane extracts was evaluated by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging method. The results indicate that hexane extracts from different parts of H. scabrum possess considerable antioxidant activity. The highest radical scavenging activity was detected in seed, which had an IC50 = 165 microg/mL. The antimicrobial activity of the extracts of those samples were determined against seven Gram-positive and Gram-negative bacteria (Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, S. epidermidis, Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae), as well as three fungi (Candida albicans, Saccharomyces cerevisiae, and Aspergillus niger). The bioassay showed that the oil exhibited moderate antimicrobial activity. This study reveals that the all parts of this plant are attractive sources of fatty acid components, especially the essential ones, as well as of effective natural antioxidants.

Antimicrobial activity and volatile constituents of the essential oil of Pulsatilla albana from Iran.

The essential oil obtained by hydrodistillation of the aerial flowering parts of Pulsatilla albana (Stev.) Bercht. & Presl. was analyzed by GC and GC/MS. Twenty-five compounds representing 97.5% of oil were identified, among them pulegone (39.1%), piperitenone (17.2%), menthone (16.1%), 1, 8-cineole (8.9%) and p-mentha-3,8-diene (4.2%). In this essential oil oxygenated monoterpenes (87.9%) predominated over monoterpene hydrocarbons (8.3%) and sesquiterpenes (1.3%). Nonterpene hydrocarbons were not found among the identified components. Antibacterial screening of the oil showed moderate activity against certain strains of Gram-positive and Gram-negative bacteria.

Free radical scavenging and antibacterial activities, and GC/MS analysis of essential oils from different parts of Falcaria vulgaris from two regions.

The chemical composition of the essential oils obtained by hydrodistillation from flower, leaf and stem of Falcaria vulgaris Bernh., from two different localities in Iran, were analyzed by GC and GC/MS (sample A from Ardabil and sample B from Khalkhal area), alpha-Pinene was the major constituent of the flower, leaf and stem oils from sample A: (43.8%, 33.0% and 50.9%, respectively). Of the 10 components detected in the oil of F. vulgaris flower, high amounts of beta-caryophyllene (25.2%) and 1,8-cineole (12.8%) were recorded, alpha-Terpinyl acetate (23.2%) and limonene (14.4%) were major constituents of the leaf oil. In the oils of sample B: alpha-pinene (16.1% in the flower oil, 31.5% in the leaf oil and 34.5% in the stem oil) was again the major compound. Limonene (14.2%) and germacrene D (32.1%) were also main constituents of the leaf oil. alpha-Terpinyl acetate (21.9% in the leaf oil) and limonene (29.8% in stem oil) were the other major compounds obtained from this sample. Antibacterial activity was determined by measurement of growth inhibitory zones, and the antioxidant activity was tested using the DPPH radical scavenging method. The essential oils from different parts and localities of Falcaria vulgaris showed free radical scavenging and antibacterial activity.

Nepetalactone content and antibacterial activity of the essential oils from different parts of Nepeta persica.

The essential oils from the flower, leaf, stem and root of Nepeta persica Boiss., analyzed by GC and GC/MS, were shown to contain 4abeta,7alpha,7abeta-nepetalactone (58.5%, 62.3%, 66.2% and 27.1%, respectively), and 4aalpha,7alpha,7abeta-nepetalactone (33.0%, 28.3%, 24.9% and 7.6%, respectively). The other main component of the flower and stem oils was alpha-pinene (3.6% and 4.4%) and of the leaf oil beta-ocimene (3.6%). In the root oil, other main constituents were alpha-pinene (40.4%), alpha-amorphene (5.3%), gamma-cadinene (2.9%), and cis-calamenene (2.5%). Nepetalactone was the major component of the flower, leaf and stem oils, which are thus important sources of nepetalactone. Antibacterial activities of the flower, leaf, stem and root oils were evaluated using the micro-dilution broth method. Inhibitory effects on Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Enterococcus faecalis were recorded. The flower, leaf, stem, and root oils had difference activities against the test microorganisms. The antibacterial property of the essential oils might be ascribed to their high content of nepetalactone isomers.

Composition and antibacterial activity of essential oils from leaf, stem and root of Chrysanthemum parthenium (L.) Bernh. from Iran.

The water distilled essential oils from leaves, stems and roots of Chrysanthemum parthenium (L.) Bernh. were analyzed by GC and GC/MS methods. The leaf oil was characterized by a high amount of camphor (56.4%), whereas in the stem oil, camphor (26.0%), trans-beta-ocimene (23.6%) and germacrene-d (15.0%) were the major constituents. The main components of the root oil were alpha-pinene (50.0%), trans-beta-farnesene (13.8%) and bicyclogermacrene (11.0%). Antibacterial activity of the leaf, stem and root oil were evaluated using the micro-dilution broth method. The oils showed inhibitory effects on Escherichia coli and Salmonella typhi, but were not active against Staphylococcus aureus.

Antibacterial activity and composition of essential oils from flower, leaf and stem of Chaerophyllum macropodum Boiss. from Iran.

The hydrodistilled essential oils from flower, leaf and stem of Chaerophyllum macropodum Boiss. were analyzed by GC and GC/MS. The flower oil was characterized by high amounts of myristicin (42.5%) and trans-beta-ocimene (41.0%). In the leaf oil eighteen constituents, representing 99.3% of the total, were identified of which trans-beta-ocimene (24.9%), myristicin (15.7%), terpinolene (14.5%), fenchyl acetate (13.9%), cis-beta-ocimene (6.3%) and sabinene (6.1%) were major components. The main components of the stem oil were trans-beta-ocimene (54.2%), myristicin (22.4%) and sabinene (8.9%). Antibacterial activities of the flower, leaf and stem oils were evaluated using the micro-dilution broth method. Inhibitory effects on Escherichia coli and Salmonella typhi were recorded.

Composition and antibacterial activity of essential oils of Artemisia fragrans Willd. leaves and roots from Iran.

Hydrodistillation of leaves and roots of Artemisia fragrans Willd. (Asteraceae) yielded 0.9% and 0.1% (v/w) essential oils, respectively. GC/MS analysis allowed identification of 19 components, which made up 91.1% of the total oil from the leaves, while only 9 compounds (93.8%) were identified in the roots. The main components of the leaf oil were chrysanthenon (23.8%), 1, 8-cineole (23.7%), beta-caryophyllene (9.6%), p-cymene (7.7%), filifolide-A (5.7%) and filifolone (5.7%). In the root oil, the main constituents were camphor (67.0%) and camphene (16.9%). Antibacterial activity was tested against Gram-positive and Gram-negative bacteria using the agar diffusion method. Activity was observed against two Gram-positive and one Gram- negative bacteria.