The composition and antifungal bioassay of the essential oils of differentBetula species growing in Turkey

FiveBetula species,B. pendula, B. browicziana, B. medwediewii, B. litwinowii, andB. recurvata, were collected from different parts of Turkey. The leaves of these species were hydrodistilled to yield the consequent essential oils. The essential oil compositions were investigated by GC/MS. 14-Hydroxy--caryophyllene was the main constituent in the oil ofB. pendula. 14-Hydroxy-4,5-dihydro--caryophyllene, a new compound, was identified as the main constituent in the oils ofB. browicziana, B. litwinowii, and B. recurvata. In the oil ofB. medwediewii methyl salicylate was the main compound. Various phytopathogenic fungi were studied by the agar tube dilution technique to test the antifungal activities of the essential oils at 400 g/ml concentration. The essential oils showed strong antifungal activity againstCephalosporium aphidicola, Drechslera sorokinianse, Fusarium solani, andRhizoctonia cerealis.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 126–130, March–April, 2000.     

Constituents and biological activity of the chloroform extract and essential oil of <Emphasis Type="Italic">Cupressus sempervirens</Emphasis>

The essential oil of the leaves of Cupressus sempervirens L. was isolated by hydrodistillation and tested against gram positive and gram negative bacteria, showing remarkable antimicrobial activity against Bacillus subtilis with minimum inhibitory concentration (MIC) 75%. The antiviral activity of the essential oil was tested against Herpes simplex virus type 1 (HSV-1), showing antiviral activity with virucidal percentages of 68.0% and 53.2% at concentrations of 1:32 and 1:64, respectively. We firstly reported the isolation of two epi-betulin esters of fatty acids from the CHCl₃ fraction of Cupressus sempervirens L. leaves, which were isolated and purified using HPLC, and identified using PMR and MS. The CHCl₃ fraction showed significant cytotoxicity against HeLa cells. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 265–268, May–June, 2009.     

Fatty Acid Composition of Seed Oils of Twelve Salvia Species Growing in Turkey

Seed oils of 12 Salvia species collected from different regions in Turkey (S. Albimaculata Hedge & Hub.-Mor., S. Candidisima Vahl., S. Cedronella Boiss., S. Cryptantha Montbret & Aucher ex Bentham, S. Forskahlei L., S. Fruticosa Miller (Sin. S. Triloba L. Fil), S. Halophila Hedge, S. Hypargeia Fisch. & Mey., S. Sclarea L., S. Tomentosa Miller, S. Tchihatcheffii (Fisch. & Mey.) Boiss., S. Virgata Jacq.) were obtained by Soxhlet apparatus using hexane. The oil yields were found to be between 2.0% and 20.9%. Fatty acids in the oils were converted to methyl esters and determined by GC/MS in methyl ester form. The main fatty acid components of S. halophila, S. Hypargeia, and S. Sclarea are unsaturated oleic, linoleic, and linolenic acids. In others except S. Candidissima, the dominant acids are oleic, linoleic and palmitic acids.     

Determination of the volatile constituents and total phenolic contents of some endemic Stachys taxa from Turkey

The total phenolic contents and the essential oil compositions of the previously unknown Stachys taxa (Labiatae), including Stachys pinardii Boiss, Stachys cretica L. subsp. mersinaea (Boiss.) Rech., and Stachys aleurites Boiss. & Heldr., all endemic to Turkey, were studied. Their essential oil compositions were investigated by GC-MS. It was found that the main constituents were α-curcumene (34.10%) for S. cretica, cedrandiol (25.26%) and caryophyllene dioxide (22.15%) for S. pinardii, and (Z)-β-caryophyllene (31.60%) for S. aleurites. The total phenolic contents, by the Folin-Ciocalteu colorimetric method, of the S. pinardii, S. cretica subsp. mersinaea, and S. aleurites methanolic extract were found to be 600.74±0.23, 1200.94±0.11, and 900.61±0.06 mg gallic acid equivalent (GAE)/100 g in dried herb, respectively. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 141–143, March–April, 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.     

Antifungal and phytotoxic activity of essential oil from root of Senecio amplexicaulis Kunth. (Asteraceae) growing wild in high altitude-Himalayan region

This work was aimed to evaluate the essential oil from root of medicinally important plant Senecio amplexicaulis for chemical composition, antifungal and phytotoxic activity. The chemical composition analysed by GC/GC–MS showed the presence of monoterpene hydrocarbons in high percentage with marker compounds as α-phellandrene (48.57%), o-cymene (16.80%) and β-ocimene (7.61%). The essential oil exhibited significant antifungal activity against five phytopathogenic fungi, Sclerotium rolfsii, Macrophomina phaseolina, Rhizoctonia solani, Pythium debaryanum and Fusarium oxysporum. The oil demonstrated remarkable phytotoxic activity in tested concentration and significant reduction in seed germination percentage of Phalaris minor and Triticum aestivum at higher concentrations. The roots essential oil showed high yield for one of its marker compound (α-phellandrene) which makes it important natural source of this compound.     

Synthesis and biological activity of a cyclic hexapeptide from Dianthus superbus

Plant-originated cyclopolypeptide (XIII) was synthesized by coupling of dipeptide Boc-l-asn(bzh)-l-phe-OH and tetrapeptide gly-l-leu-l-ala-l-tyr-OMe followed by cyclization of a linear hexapeptide segment. Structure elucidation of XIII was done on basis of detailed spectral analysis including FTIR, ¹H NMR, ¹³C NMR, FAB MS and elemental analysis. From the results of pharmacological screening, it was concluded that XIII possesses high cytotoxic activity against DLA and EAC cell lines with CTC₅₀ values of 15.1 μM and 18.6 μM, and potent antimicrobial activity against pathogenic fungi C. albicans with MIC of 6 μg mL⁻¹. Moreover, XIII possesses moderate anthelmintic activity against earthworms M. konkanensis, P. corethruses, and Eudrilus sp. at 2 mg mL⁻¹ dose level.     

Chemical composition of the resin essential oil of Canarium album from Vietnam

The composition of the essential oil obtained from the resin of Canarium album (Lour.) Raeusch, Burseraceae, growing in Vietnam, was studied by GC and GC/MS. Twenty-nine compounds representing 95.2% of the oil were identified. Monoterpenoids made up 93.2% of the oil, with β-pinene (33.3%), α-terpinene (19.4%), γ-terpinene (14.1%), and terpinen-4-ol (11.9%) as the main components. Sesquiterpenoids made up 2.0% of the oil, and the content of each individual was below 0.5% of the oil. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 421–422, September–October, 2006.     

Chemical composition of the essential oil of Jacobaea maritima (L.) Pelser & Meijden and Jacobaea maritima subsp. bicolor (Willd.) B. Nord. & Greuter (Asteraceae) collected wild in Croatia and Sicily,respectively

In this study, the chemical compositions of the essential oils from aerial parts (JmA) and radices (JmR) of Jacobaea maritima (L.) Pelser & Meijden, collected in Croatia, and of Jacobaea maritima subsp. bicolor (Willd.) B. Nord. & Greuter, collected in Sicily, were evaluated by using gas chromatography and gas chromatography–mass spectrometry. The main components of the essential oil from J. maritima, both in JmA and JmR, were pentacosane (15.7%), heptacosane (13.1%) and nonacosane (8.1%) whereas the essential oil from J. maritima subsp. bicolor was characterised by the presence of hexadecanoic acid (14.6%), caryophyllene oxide (9.3%) and hexahydrofarnesylacetone (6.5%). The comparison of the essential oil with other studied oils of the genus Jacobaea is discussed.     

Production of essential oil from Cumin seeds

Steam distillation of cumin (Cuminum cyminum L.) seeds was studied to show the effects of particle size, batch size, and distillation rate on their essential oil recovery. Experiments were carried out both on bench and pilot scale. The composition of the oil was analyzed by GC/MS.Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 214–216, May–June, 2000.     

<Emphasis Type="Italic">Ferula gummosa</Emphasis> Fruits: An Aromatic Antimicrobial Agent

Ferula gummosa Boiss. (Apiaceae) fruit volatile oil was analyzed by GC/MS. Seventy-three components (96.89%) were identified, and the major components were β-pinene (43.78%), α-pinene (27.27%), and myrcene (3.37%). The antimicrobial activity of the oil was tested on three strains of Gram positive bacteria (Staphylococcus aureus, S. epidermis, and Bacillus subtilis), three strains of Gram negative bacteria (Escherichia coli, Salmonella typhi, and Pseudomonas aeruginosa), and two strains of fungi (Candida albicans and C. kefyr). The essential oil remarkably inhibited the growth of the tested microorganisms. The results indicate that the fruits have potential for use as an aromatic antimicrobial agent.__________Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 252–254, May–June, 2005.     

Thermal analysis and gas chromatography coupled mass spectrometry analyses of hydroxypropyl-β-cyclodextrin inclusion complex containing Lippia gracilis essential oil

Inclusion complexation with cyclodextrins is an effective way to improve stability and turn liquid materials into re-dispersible and easy-to-handle powders. In the present work, the complexation of L. gracilis essential oil, already recognized as a potent larvicide material, with hydroxylpropyl-β-cyclodextrin was performed using slurry and paste procedures and the complexes obtained were evaluated. The gas chromatography coupled to mass spectrometry (GC/MS) analysis showed a total volatile content of 99.24% in the L. gracilis oil. The characterization of the complex involved the analysis of the original essential oil, the surface, and the total extracted oils. The major components in L. gracilis essential oil were identified as carvacrol (23.52%), p-cymene (15.82%), γ-terpinene (14.17%), and thymol (7.27%). GC/MS results showed significant differences between the original oil, the slurry, and paste complexation. Thermal characterization indicates the occurrence of complexation, mainly in paste complexes, which presents a TG–DTA peak at 230–275 °C, probably related to oil loss.     

Comparison of different extraction methods for the determination of essential oils and related compounds from aromatic plants and optimization of solid-phase microextraction/gas chromatography

Different extraction methods for the subsequent gas chromatographic determination of the composition of essential oils and related compounds from marjoram (Origanum majorana L.), caraway (Carum carvi L.), sage (Salvia officinalis L.), and thyme (Thymus vulgaris L.) have been compared. The comparison was also discussed with regard to transformation processes of genuine compounds, particularly in terms of expenditure of time. Hydrodistillation is the method of choice for the determination of the essential oil content of plants. For investigating the composition of genuine essential oils and related, aroma-active compounds, hydrodistillation is not very useful, because of discrimination and transformation processes due to high temperatures and acidic conditions. With cold solvent extraction, accelerated solvent extraction, and supercritical fluid extraction, discrimination of high and non-volatile aroma-active components as well as transformation processes can be diminished, but non-aroma-active fats, waxes, or pigments are often extracted, too. As solid-phase microextraction is a solvent-free fully automizable sample preparation technique, this was the most sparing to sensitive components and the most time-saving method for the rapid determination of the aroma compounds composition in marjoram, caraway, sage, and thyme. Finally, solid-phase microextraction could be successfully optimized for the extraction of the aroma components from the plants for their subsequent gas chromatographic determination.     

First report of toxicity of Xylopiaparviflora (A. Rich.) Benth (Annonaceae) root bark's essential oil against cowpea seed bruchid,Callososbruchus maculatus Fabricius (Coleoptera: Chrysomelidae: Bruchinae)

The fumigant toxicity of Xylopia parviflora (A. Rich.) Benth (Annonaceae) root bark's essential oil (EO) against cowpea seed bruchid, Callosobruchus maculatus, was investigated in the laboratory. Dose had significant (P < 0.0001) effect on mortality at 6 hours after treatment (HAT) at a concentration of 6.25 μL/mL air which exerted 81.70% mortality, while there was no mortality in all other lower doses. At 12 HAT, 75.05% and 90.00% mortality were observed at doses of 3.15 and 6.25 μL/mL air, respectively. It was significantly (P < 0.05) higher than the mortality (50.58%) observed when 0.78 μL/mL air was applied. The lethal time for 50% of assayed adults (LT₅₀) obtained when the bruchid was exposed to X. parviflora EO at a dose of 6.25 μL/mL air (2.71 h) was significantly lower than LT₅₀ obtained at exposure of bruchid to other lower doses of 0.78–3.15 μL/mL air.     

The Antimicrobial Activity,Mosquito Larvicidal Activity,Antioxidant Property and Tyrosinase Inhibition of Piper Betle

The essential oil and methanolic and aqueous extracts of Piper betle L. were assayed for their antimicrobial activity, mosquito larvicidal activity, antioxidant property and mushroom tyrosinase inhibition. The methanolic and aquaous extracts showed strong activity against the yeasts: C. albicans, and M. pachydermatis. The crude essential oil exhibited a broad‐spectrum strong antimicrobial activity against all test organisms. The strongest activity was observed against C. albicans, followed by S. aureus and M. pachydermatis. The chemical composition of the essential oil and its fractions was analyzed by GC/MS analysis. Eugenol (36.2%), chavibetol acetate (16.9%), 4‐allylphenyl acetate (9.4%) and 4‐allylphenol (7.2%) were the main components, comprising 69.7% of the oil. The fractionation of the essential oil gave two fractions. Fraction I was rich in eugenol (71.3%) and fraction II in eugenol (46.4%), chavibetol acetate (19.4%) and 4‐allylphenyl acetate (11.8%). The essential oil exhibited the mosquito larvicidal activity with 2 h and 24 h LD₅₀ value of 86 and 48 ppm, respectively. The methanolic extract of P. betle showed larvicidal activity with 2 h and 24 h LD₅₀ value of 153 and 125 ppm, respectively, whereas the aqueous extract showed slight active. The individual antioxidant assays such as DPPH scavenging activity, chelating effect of ferrous ions and reducing power have been used. P. betle showed remarkable antioxidant activity in DPPH and reducing power assays. The activity observed can be attributed to the presence of the phenolic compounds. The essential oil exhibited concentration‐dependent inhibition of mushroom tyrosinase, giving an IC₅₀ value of 126 ppm. The fraction I showed a strong inhibition of tyrosinase activity, giving an IC₅₀ value of 115 ppm. The presence of 4‐allylphenolic components in the essential oil may play an important role in the inhibition of tyrosinase. In conclusion, the results presented here show that Piper betle essential oil could be considered as a natural antimicrobial, mosquito larvicidal, antioxidant and tyrosinase inhibition source.     

Composition and Antimicrobial Activity of <Emphasis Type="Italic">Helichrysum italicum</Emphasis> Essential Oil and Its Terpene and Terpenoid Fractions

The essential oil of Helichrysum italicum (Roth) G. Don from Croatia has been fractionated into terpene and terpenoid fractions and analyzed using GC/MS. Fifty-two compounds were identified. The main hydrocarbons of the oil were α-pinene (10.2%), α-cedrene (9.6%) aromadendrene (4.4%), β-caryophyllene (4.2%), and limonene (3.8%), while the main oxygen-containing compounds were neryl acetate (11.5%), 2-methylcyclohexyl pentanoate (8.3%), 2-methylcyclohexyl octanoate (4.8%), and geranyl acetate (4.7%). The essential oil and its terpene and terpenoid fractions were evaluated for antibacterial and antifungal activities. The screening of antimicrobial activity was conducted by a disc diffusion test and the minimum inhibitory concentration was determined against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Candida albicans. The essential oil and its terpenoid fraction exhibited higher antimicrobial activity with respect to the terpene fraction. The antimicrobial activities of the oil and its terpenoid fraction were more pronounced against Staphylococcus aureus and Candida albicans.__________Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 29–32, January–February, 2005.     

Essential oil composition of <Emphasis Type="Italic">Santolina etrusca</Emphasis> from Italy

The essential oil composition of aerial parts of Santolina etrusca Marchi & D’Amato from Italy was analyzed by GC and GC/MS. Twenty-nine compounds of oil were identified representing 97.1% of the oil. The most abundant compounds were viridiflorol (17.9%), terpinen-4-ol (14.4%), myrcene (11.8%), β-pinene (9.9%), and cis-muurola-4(14),5-diene (9.9%). To the best of our knowledge, this is the first report on the GC/MS determination of the essential oil composition of S. etrusca. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 38–39, January–February, 2007.     

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.     

Effects of gamma irradiation on the yields of volatile extracts of Angelica gigas Nakai

The study was carried out to determine the effects of gamma irradiation on the volatile flavor components including essential oils, of Angelica gigas Nakai. The volatile organic compounds from non- and irradiated A. gigas Nakai at doses of 1, 3, 5, 10 and 20 kGy were extracted by a simultaneous steam distillation and extraction (SDE) method and identified by GC/MS analysis. A total of 116 compounds were identified and quantified from non- and irradiated A. gigas Nakai. The major volatile compounds were identified 2,4,6-trimethyl heptane, α-pinene, camphene, α-limonene, β-eudesmol, α-murrolene and sphatulenol. Among these compounds, the amount of essential oils in non-irradiated sample were 77.13%, and the irradiated samples at doses of 1, 3, 5, 10 and 20 kGy were 84.98%, 83.70%, 83.94%, 82.84% and 82.58%, respectively. Oxygenated terpenes such as β-eudesmol, α-eudesmol, and verbenone were increased after irradiation but did not correlate with the irradiation dose. The yields of active substances such as essential oil were increased after irradiation; however, the yields of essential oils and the irradiation dose were not correlated. Thus, the profile of composition volatiles of A. gigas Nakai did not change with irradiation.     

Analysis of terpenoic composition of conifer needle oils by steam distillation/extraction,gas chromatography and gas chromatography-mass spectrometry

Summary The essential oils of Estonian spruce and pine needles have been analysed by a combination of steam distillation/extraction, GC and GC-MS. According to their monoterpene composition Estonian pines belong to a high carene chemotype with monoterpenes representing up to 85% of total oil. Estonian spruce needle oil contains up to 70% of oxygenated terpenes and more limonene and 1,8-cineole than the same spruce species [Picea abies (L.) Karst.] from other localities.A total of 60 components were identified. Coefficients of variation describe the range of component contents in individual trees within the population.