Chemical Composition,Biological Activities and In Silico Analysis of Essential Oils of Three Endemic Prangos Species from Turkey

In this study, the essential oils (EOs) obtained from three endemic Prangos species from Turkey (P. heyniae, P. meliocarpoides var. meliocarpoides, and P. uechtritzii) were studied for their chemical composition and biological activities. β-Bisabolenal (12.2%) and caryophyllene oxide (7.9%) were the principal components of P. heyniae EO, while P. meliocarpoides EO contained sabinene (16.7%) and p-cymene (13.2%), and P. uechtritzii EO contained p-cymene (24.6%) and caryophyllene oxide (19.6%), as the most abundant components. With regard to their antioxidant activity, all the EOs were found to possess free radical scavenging potential demonstrated in both DPPH and ABTS assays (0.43–1.74 mg TE/g and 24.18–92.99 mg TE/g, respectively). Additionally, while no inhibitory activity was displayed by P. meliocarpoides and P. uechtritzii EOs against both cholinesterases (acetyl- and butyryl-cholinesterases). Moreover, all the EOs were found to act as inhibitors of tyrosinase (46.34–69.56 mg KAE/g). Molecular docking revealed elemol and α-bisabolol to have the most effective binding affinity with tyrosinase and amylase. Altogether, this study unveiled some interesting biological activities of these EOs, especially as natural antioxidants and tyrosinase inhibitors and hence offers stimulating prospects of them in the development of anti-hyperpigmentation topical formulations.     

Investigation of the composition and stability of the essential oils of origanum vulgare ssp.vulgare L. andO. vulgare ssp.hirtum (Link) letswaart

Summary The essential oils ofOriganum vulgare L. ssp.hirtum (Link) letswaart andOriganum vulgare L ssp.vulgare (Fam. Lamiaceae), cultivated in Hungary, have been studied by GC and GC-MS and the qualitative and quantitative chemical composition of the essential oils in the two species have been compared.O. vulgare ssp.hirtum oil was found to contain carvacrol (76.4%), γ-terpinene (6.6%), thymol (0.23%), andp-cymene (4.7%) as the main constituents whereas the major compounds inO. vulgare ssp.vulgare oil werep-cymene (22.3%), caryophyllene oxide (10.2%), sabinene (7.9%), γ-terpinene (5.1%), thymol (0.34%), and spathulenol (4.8%). The stability of content and composition of the oils during the flowering period (economically beneficial period) were observed. The effect of long-term storage on the composition of the oil was also investigated for both the crude and distilled oil ofOriganum vulgare ssp.vulgare. Presented at Balaton Symposium '01 on High-Performance Separation Methods, Siófok, Hungary, September 2–4, 2001     

Chemical Compositions of the Essential Oils of Stems,Leaves, and Roots of <Emphasis Type="Italic">Prangos latiloba</Emphasis>

Hydrodistilled volatile oils from crushed dry stems, leaves, and roots of Prangos latiloba Korov. (Umbelliferae) growing wild in Sabzevar (Iran) were analyzed by GC and GC/MS. Eight compounds constituting 84.72% of stem oil, twelve compounds constituting 95.39% of leaf oil, and nine compounds constituting 88.73% of root oil have been identified. The main components of stem oil were γ-cadinene (30.39%), α-pinene (25.47%), and sabinene (12.55%). The main components of leaf oil were germacrene D (27.79%), α-pinene (17.81%), β-caryophyllene (12.75%), and β-pinene (11.23%). The main components of root oil were spathulenol (29.5%), 1,8-cineol (19.42%), p-cymene (17.03%), and α-bisabolol (15.33%). __________ Published in Kimiya Prirodnikh Soedinenii, No. 5, pp. 443–444, September–October, 2005.     

Investigation of the chemical composition–antibacterial activity relationship of essential oils by chemometric methods

The antibacterial effects of Thymus vulgaris (Lamiaceae), Lavandula angustifolia (Lamiaceae), and Calamintha nepeta (Lamiaceae) Savi subsp. nepeta var. subisodonda (Borb.) Hayek essential oils on five different bacteria were estimated. Laboratory control strain and clinical isolates from different pathogenic media were researched by broth microdilution method, with an emphasis on a chemical composition–antibacterial activity relationship. The main constituents of thyme oil were thymol (59.95%) and p-cymene (18.34%). Linalool acetate (38.23%) and β-linalool (35.01%) were main compounds in lavender oil. C. nepeta essential oil was characterized by a high percentage of piperitone oxide (59.07%) and limonene (9.05%). Essential oils have been found to have antimicrobial activity against all tested microorganisms. Classification and comparison of essential oils on the basis of their chemical composition and antibacterial activity were made by utilization of appropriate chemometric methods. The chemical principal component analysis (PCA) and hierachical cluster analysis (HCA) separated essential oils into two groups and two sub-groups. Thyme essential oil forms separate chemical HCA group and exhibits highest antibacterial activity, similar to tetracycline. Essential oils of lavender and C. nepeta in the same chemical HCA group were classified in different groups, within antibacterial PCA and HCA analyses. Lavender oil exhibits higher antibacterial ability in comparison with C. nepeta essential oil, probably based on the concept of synergistic activity of essential oil components.     

Composition and Antimicrobial Activity of the Essential Oils of Two Endemic Species from Turkey: <Emphasis Type="Italic">Sideritis cilicica</Emphasis> and <Emphasis Type="Italic">Sideritis bilgerana</Emphasis>

Aerial parts of Sideritis cilicica Boiss. & Bal. and Sideritis bilgerana P.H. Davis (Lamiaceae) were hydrodistilled to obtain essential oils that were then analyzed by GC and GC/MS. β-Pinene (39%), α-pinene (28%), and β-phellandrene (20%) were the main components in the oil of S. cilicica, while β-pinene (48%), and α-pinene (32%) were the major constituents in the oil of S. bilgerana. The antimicrobial activities of the oils were evaluated by using the microdilution broth method. Both of the oils showed good inhibitory effects on C. albicans. __________ Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 559–561, November–December, 2005.     

Identification by GC—MS of cymene isomers and 3,7,7-trimethylcyclohepta-1,3,5-triene in essential oils

Retention indices of cymene isomers published in popular GC—MS atlases were found to be erroneous by analyzing synthetic samples. The following retention indices (RI) were found using a nonpolar phase (diphenyl: dimethylpolysiloxane, 5:95) for four essential-oil components with indistinguishable mass spectra: 3,7,7-trimethylcyclohepta-1,3,5-triene (RI = 970), m-cymene (RI = 1022), p-cymene (RI = 1024), and o-cymene (RI = 1039). The relative distributions of these compounds were evaluated based on the analysis of about 1000 essential oils. Simple methods were given for preparing standard mixtures of isomeric compounds for identification by GC—MS. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 569–571, November–December, 2006.     

Authenticity control of essential oils containing citronellal and citral by chiral and stable-isotope gas-chromatographic analysis

Enantioselective capillary GC on a Supelco β-DEX 225 column (heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin SPB 20poly—20% diphenyl, 80% dimethylsiloxane) and isotope-ratio mass spectrometry, coupled online with capillary GC on an HP5 column have been used for origin-specific analysis and authenticity control of essential oils, for example lemon (Citrus limon), lemongrass (Cymbopogon citratus and Cymbopogon flexuosus), citronella (Cymbopogon nardus L.—Ceylon type and Cymbopogon winterianus—Java type), Litsea cubeba, Lippia citriodora, lemon myrtle (Backhousia citriodora), lemon gum (Eucalyptus citriodora), and, especially, precious lemon balm oil (Melissa officinalis L.). Isotope data (δ¹³C_PDB and δ²H_V-SMOW) for citral (neral + geranial) and citronellal from on-line GC–C/Py–IRMS and chiral data for citronellal in these essential oils are reported. The possibility of using these data to determine the origin of these essential oils and to detect adulteration is discussed. Principal-components analysis (PCA) of specific compounds in two essential oils of lemongrass and Litsea cubeba was performed as a practical statistical method for distinguishing between these two types of oil.     

Chemical composition,antimicrobial and antioxidant activities of the essential oils of three Uzbek Lamiaceae species

The chemical composition of the essential oil from the aerial parts of three Lamiaceae species from Uzbekistan was investigated by GC-MS analysis. β-Linalool (26.6%), α-terpineol (10.0%), coumarin (8.9%) and 4,5,7,7α-tetrahydro-4,4,7α-trimethyl-2(6H)-benzofuranone (5.4%) resulted as the main components of Ajuga turkestanica essential oil, while camphene (17.1%), 1,8-cineole (15.9%), β-cymene (7.9%) and limonene (7.4%) in Phlomis regelii. The essential oil of Thymus seravschanicus was dominated by thymol (37.5%), phellandral (26.0%), τ-terpinene (6.6%) and β-cymene (5.2%). The essential oils had considerable antimicrobial activity against different bacterial strains and fungi. Among the tested samples of essential oils, P. regelii essential oil has the significant antioxidant activity with IC₅₀ value of 117.8 ± 8.02 μg/mL.     

Chemical composition and antimicrobial activity of the essential oils of Ferula latisecta and Mozaffariania insignis from Iran

The hydrodistilled oils from the aerial parts of Ferula latisecta and Mozaffariania insignis, which is endemic to Iran, were analyzed by GC and GC/MS. (Z)-Ocimenone (32.4%), (E)-ocimenone (20.3%), and cis-pinocarvone (11.4%) were the main components among the 22 constituents characterized in the oil of F. latisecta, representing 87.7% of the total components detected. Twenty-five compounds were identified in the oil of M. insignis, representing 99.0% of the total oil, with octyl acetate (41.1%), β-pinene (30.3%), and α-pinene (23.9%) as the main constituents. The essential oils were examined for their potential antimicrobial activities. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 561–563, November–December, 2006.     

Component composition of essential oils from four species of the genus Achillea growing in Kazakhstan

The component composition of the four species Achillea filipendulina, A. sudetica, A. ledebourii, and A. cartilaginea was studied by GC-MS. It was found that the principal components of the essential oil (%) were santolina alcohol (29.1) and borneol (27.9) for A. filipendulina, linalool (11.8) and caryophyllene (8.9) for A. sudetica, germacrene D (20.55) for A. ledebourii, and α-thujone (26.15) and β-thujone (11.76) for A. cartilaginea. The chemical composition of the essential oils from A. sudetica, A. ledebourii, and A. cartilaginea was studied for the first time. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 243–245, May–June, 2006.     

Senna occidentalis (L.) Link and Senna hirsuta (L.) H. S. Irwin & Barneby: constituents of fruit essential oils and antimicrobial activity

Senna occidentalis and S. hirsuta are mostly gathered from the wild for medicinal use and have a disagreeable odour when crushed. The volatile oils isolated from fresh fruits of S. occidentalis and S. hirsuta were subjected to gas chromatography (GC), gas chromatography-mass spectrometry (GC-MS) and antimicrobial assays. GC and GC-MS analyses permitted the identification of 58 constituents. S. occidentalis oil was dominated by cyperene (10.8%), β-caryophyllene (10.4%), limonene (8.0%) and caryophyllene oxide (6.8%). The main components of S. hirsuta fruit oil were benzyl benzoate (24.7%), τ-cadinol (18.9%), 2,5-dimethoxy-p-cymene (14.6%) and β-caryophyllene (5.1%). S. occidentalis fruit oil exhibited better antimicrobial activity (MIC 78–312 μg/mL) against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Aspergillus niger compared with S. hirsuta oil. The compositions and the activities of the fruit essential oils of S. occidentalis and S. hirsuta are reported for the first time.     

Buffers for the physiological pH range: Thermodynamic constants of substituted aminopropanesulfonic acids from 5 to 55°C

ThepK ₂ values for 3-[(l,l-Dimethyl-2-hydroxymethyl)amino]-2-hydroxypropanesulfonic acid (AMPSO), and 3-[N,N-Bis(-hydroxyethyl)amino]-2-hydroxypropanesulfonic acid (DIPSO) have been determined at 12 temperatures over the range 5 to 55‡C by measurements of the emf of cells without liquid junction containing hydrogen and silver-silver chloride electrodes. The values of pK ₂ for AMPSO and DIPSO were found to be 9.138 and 7.576, respectively, at 25‡C. The thermodynamic quantities, δG‡, δH‡, δS‡, and δC _p ^‡ were calculated from the change of the equilibrium constants with temperature. These buffer substances are useful as secondary pH standards in the physiological region of pH 7 to 9. Camille and Henry Dreyfus Fellow, 1994–1996.     

Chemotyping of diverse Eucalyptus species grown in Egypt and antioxidant and antibacterial activities of its respective essential oils

The chemical composition of the essential oil from the leaves of Eucalyptus camaldulensis, Eucalyptus camaldulensis var. obtusa and Eucalyptus gomphocephala grown in northern Egypt was analysed by using GC-FID and GC–MS techniques. The antibacterial (agar disc diffusion and minimum inhibitory concentration methods) and antioxidant activities (2,2′-diphenypicrylhydrazyl) were examined. The main oils constituents were 1,8-cineole (21.75%), β-pinene (20.51%) and methyleugenol (6.10%) in E. camaldulensis; spathulenol (37.46%), p-cymene (17.20%) and crypton (8.88%) in E. gomphocephala; spathulenol (18.37%), p-cymene (19.38%) and crypton (16.91%) in E. camaldulensis var. obtusa. The essential oils from the leaves of Eucalyptus spp. exhibited considerable antibacterial activity against Gram-positive and Gram-negative bacteria. The values of total antioxidant activity were 70 ± 3.13%, 50 ± 3.34% and 84 ± 4.64% for E. camaldulensis, E. camaldulensis var. obtusa and E. gomphocephala, respectively. The highest antioxidant activity value of 84 ± 4.64% could be attributed to the high amount of spathulenol (37.46%).     

Chemical composition and antimicrobial activity of Erodium species: E. ciconium L., E. cicutarium L., and E. absinthoides Willd. (Geraniaceae)

The present study gives results of chemical composition analyses and antimicrobial activity testing of three Erodium species: E. ciconium L., E. cicutarium L., and E. absinthoides Willd. Essential oils were obtained by hydro-distillation from air-dried entire plants and analyzed by GC and GC-MS. A total of 209 different compounds were identified: 162 for E. cicutarium, 107 for E. ciconium, and 79 for E. absinthoides. Antimicrobial activity (broth microdilution method) of the oils was screened against a panel of Gram positive and Gram negative bacteria and a number of fungi. Moderate susceptibility of all tested strains was observed. Determined MIC values were 0.156–5 mg mL⁻¹ (bacterial strains) and 0.039–0.325 mg mL⁻¹ (fungal strains). Major component of the most active oil, palmitic acid, was also tested for activity together with stearic and myristic acids.     

Volatile constituents of flowers and leaves of Anthemis hyalina

The chemical composition of the essential oils of the flowers and leaves of Anthemis hyalina were analyzed by GC and GC-MS for the first time. The oils were found to contain seventy-two components. cis-Chrysanthenyl acetate (14.9% and 17.8%), camphor (11.6% and 1.7%), terpinen-4-ol (8.3% and 1.2%), germacrene-D (5.1% and 2.1%), β-caryophyllene (4.1% and 5.4%), myrcene (3.6% and 16.9%), bicyclogermacrene (3.5% and 0.9%), α-pinene (2.3% and 4.1%), cis-β-ocimene (2.1% and 4.3%) and isospathulenol (0.4% and 4.3%) were found to be the major constituents of the oils of flowers and leaves respectively. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 428–429, September–October, 2006.     

Essential Oil Composition of Four <Emphasis Type="Italic">Achillea</Emphasis> Species from the Balkans and Its Chemotaxonomic Significance

The chemical composition of the essential oils of Achillea clavennae L., Achillea holosericea Sibth. & Sm., Achillea lingulata W. & K., and Achillea millefolium L. from the Balkans was determined by GC and GC/MS analyses. The main components were 1,8-cineole in A. holosericea, camphor in A. clavennae, β-pinene in A. millefolium, and τ-cadinol in A. lingulata. A detailed chemotaxonomic discussion is presented. __________ Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 555–558, November–December, 2005.     

Electrophysical properties of materials based on BaGdCo2O5 + δ

The phase composition, linear thermal expansion coefficient, electroconductivity (in the temperature interval 600–900°C and partial pressures of oxygen 10⁻⁵–0.21 atm) of solid-oxide materials based on gadolinium-barium cobaltite doped with 3d-elements BaGdCo_{2 − x} Me _x O_{5 + δ}, Me = Cu, Fe; x = 0.0, 0.2, …, 2.0 were investigated. The homogeneity regions of samples were established by means of X-ray phase analysis. It was shown that the linear thermal expansion coefficient of cobaltite decreases with an increase in the copper or iron concentration. It was established that the electroconductivity of BaGdCo_{2 − x} Me _x O_{5 + δ} decreases with an increase in x. We concluded that upon a decrease in p(O₂), the electroconductivity of samples first decreases and then reaches a horizontal plateau.     

Chemical composition and antimicrobial activity of the essential oil of <Emphasis Type="Italic">Anthemis wiedemanniana</Emphasis> from Turkey

The chemical composition and antimicrobial activity of the essential oil from aerial parts of Anthemis wiedemanniana, an endemic taxon of Turkey, were investigated. Linalool (12.75%), 1,8-cineole (8.49%), hexadecanoic acid (6.09%), and chrysanthenone (5.67%) were found to be the main components among the 122 compounds characterized in the essential oil of Anthemis wiedemanniana. Antimicrobial activities were reported against 12 microorganisms and five yeast-like fungi by the disc diffusion method. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 40–43, January–February, 2007.     

Study of the essential oil composition of Pinus sylvestris from Turkey

The needle oils of Pinus sylvestris L. were analyzed by GC and GC-MS. The results showed some qualitative and quantitative variations. Forty-three components were identified in the oils of P. sylvestris. All the samples of essential oils contained α-pinene, camphene, and β-pinene as major constituents. Chemical variations of P. sylvestris samples were discussed. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 22–25, January–February, 2006.     

Chemical composition and antimicrobial evaluation of the essential oils of Bocageopsis pleiosperma Maas

Essential oils from the leaves, twigs and barks of Bocageopsis pleiosperma Maas were obtained by using hydrodistillation and analysed by using gas chromatography coupled to mass spectrometry. Several compounds (51) were detected and identified, being β-bisabolene the main component in all aerial parts of the plant, with higher concentration in the leaves (55.77%), followed by barks (38.53%) and twigs (34.37%). In order to increase the biological knowledge about the essential oil of Bocageopsis species, antimicrobial activities were evaluated against the microorganisms Escherichia coli, Staphylococcus epidermidis, Enterobacter aerogenes, Candida tropicalis, Candida dubliniensis, Candida glabrata and Candida albicans. The essential oil obtained from the barks exhibited a moderate effect against S. epidermidis ATCC 1228 (MIC = 250 μg/mL), while the other oils did not exhibit antimicrobial activity. These results represent the first report about the chemical composition of B. pleiosperma and the first antimicrobial evaluation with a Bocageopsis species.