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.     

Chemotypical Variability of Leaf Oils in <Emphasis Type="Italic">Elephantopus scaber</Emphasis> from 12 Locations in China

The chemical constituents of leaf oils of Elephantopus scaber L. from 12 locations in Southern China, including three provinces and Hong Kong, were investigated using GC/MS. A total of 24 compounds were detected, of which 20 were identified by their mass spectra fragmentation patterns. The major compounds include hexadecanoic acid (8.19–39.22%), octadecadienoic acid (trace - 29.22%), five alkane homologues, i.e., n-tetradecane (1.19–5.26%), n-pentadecane (3.22–12.05%), n-hexadecane (2.38–16.26%), n-heptadecane (2.48–15.32%), and n-octadecane (1.39–9.59%), as well as tetramethylhexadecenol (2.06–4.31%). Hierarchical cluster analysis classified the leaf oils into two groups. Two main chemotypes of leaf oils in E. scaber were thus identified, one rich in hexadecanoic acid and octadecadienoic acid, and the other rich in the five alkane homologues. __________ Published in Kimiya Prirodnikh Soedinenii No. 5, pp. 403–404, September–October, 2005.     

Essential Oil Composition of <Emphasis Type="Italic">Nepeta involucrata</Emphasis> from Iran

The essential oil of Nepeta involucrata (Bunge) Bornm. (Lamiaceae) obtained by hydrodistillation from the aerial parts during the flowering stage was analyzed by GC and GC-MS. Forty-eight compounds representing 97.2% of total oil were identified. The main compounds of the oil were 1,8-cineol (23.1%), germacrene-D (15.1%), and β-pinene (12.2%). No traces of nepetalactone isomers were found as oil constituents. __________ Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 562–564, November–December, 2005.     

Composition of the Essential Oil of <Emphasis Type="Italic">Rhabdosciadium strausii</Emphasis> from Iran

The essential oil from the aerial parts of Rhabdosciadium strausii (Apiaceae) growing wild in Iran was obtained by hydrodistillation and analyzed by GC and GC-MS. Forty-two compounds were characterized, representing 97.5% of the total oil. β-Elemene (37.9%) and germacrene-D (32.2%) were identified as the major constituents. __________ Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 333–334, July–August, 2005.     

Essential oil of <Emphasis Type="Italic">Laurus nobilis</Emphasis> from Montenegro

Steam distilled oil from the shoots, separated leaves, and stem, as well as from the flower of laurel (Laurus nobilis), grown in Montenegro, were analyzed by GC and GC/MS. The yield of essential oil was as follow: 1.4% in young shoots, 1.5% in the separated leaves, and 0.7% in separated stems. The main constituents of all investigated oils were 1,8-cineole, methyleugenol, and α-terpinyl acetate. Besides, α-pinene, β-pinene, sabinene, and linalool were also present. It was interesting and important for commercial samples of laurel essential oil that there was no significant difference among the essential oil obtained from young shoots and those obtained from leaves and stem. The main constituents of the flower oil were 1,8-cineole (15.7%), β-caryophyllene (9.5%), γ-muurolene (7.1%), α-terpinyl acetate (6.5%), and methyleugenol (3.9%). Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 337–339, July–August, 2007.     

Host–Guest Complexation of <Emphasis Type="Italic">β</Emphasis>-, <Emphasis Type="Italic">γ</Emphasis>-Cyclodextrin with Alkyl Trimethyl Ammonium Bromides in Aqueous Solution

As a continuation of our previous investigation, interactions between cyclodextrin (β-CD), γ-cyclodextrin (γ-CD) and alkyl trimethylammonium bromides in aqueous solutions have been studied with titration calorimetry and ¹H NMR at 298.15 K. The results are discussed in terms of the amphiphilic interaction of CD with surfactants and the iceberg structure formed by water molecules existing around the hydrophobic tail of surfactant molecules. The stoichiometry of the β-CD–surfactant system is 1:1 whereas that of the γ-CD–surfactant system is 1:2. The corresponding formation enthalpy (negative) of the complexes of the two systems decreases with an increase in the number of carbon atoms (n) in hydrophobic chain of surfactant molecule, C _n H_2n+1, whereas the entropy increases with the enlargement of n.     

Composition of essential oils from <Emphasis Type="Italic">Salvia anatolica</Emphasis>, a new species endemic from Turkey

The component composition of essential oils produced by steam distillation from flower heads, leaves, and stems of Salvia anatolica (Lamiaceae), a recently described new species endemic from Turkey, was studied by GC/FID and GC/MS. A total of 127 volatile components representing 96% of the oil was identified in essential oil from flower heads and leaves. It was found that the principal oil components of flower heads and leaves were α-pinene (10.9%), β-pinene (6.7%), α-copaene (6.3%), heptacosane (6.2%), and hexadecanoic acid (5.0%). A total of 109 volatile compounds representing 87.9% of the oil was characterized in essential oil isolated from stems. The principal oil components of stems were identified as hexadecanoic acid (27.2%), tetradecanoic acid (15.2%), dodecanoic acid (5.5%), and α-copaene (5.0%). __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 552–555, November–December, 2007.     

The chemical composition of fruits of <Emphasis Type="Italic">Pistacia atlantica</Emphasis> desf. subsp. <Emphasis Type="Italic">atlantica</Emphasis> from Algeria

The chemical composition of the fruits of the north algerian ecotype Pistacia atlantica subsp. atlantica was determined and compared to other fruits of different species in the genus growing in south Algeria and other Mediterranean regions. These fruits were analyzed for their dry matter, protein, crude oil, ash, fatty acids, and phytosterol content. The main fatty acids identified by gas chromatography were oleic (54.15%), linoleic (28.84%), and palmitic (12.21%) acids. The fruits of the north ecotype were found to be rich in protein, oil, fiber, and unsaturated fatty acids, suggesting that they may be valuable for food uses. The sterols isolated were campesterol, stigmasterol, β-sitosterol, and Δ⁵-avenasterol with β-sitosterol as the major constituent (85%±0.85). The biochemical data indicated an elevated MUFA rate (∼56%) in pistacia oil which may be important against certain pathologies for its nutritional and preventive virtues. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 103–105, March–April, 2007.     

Reaction of frangula-emodin with <Emphasis Type="Italic">α</Emphasis>-bromoalkylmethylketones

The alkylation of 1,6,8-trihydroxy-3-methylanthraquinone (frangula-emodin) by α-bromoalkylmethylketones was investigated. Hydroxyls in the 1-and 8-positions of the β-derivatives were O-acylated. The compositions and structures of the prepared compounds were confirmed by elemental analysis and UV, IR, PMR, and ¹³C NMR spectroscopy. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 324–326, July–August, 2007.     

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.     

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.     

Triterpene glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXVI. Glycosides from <Emphasis Type="Italic">A. sieversianus</Emphasis>

Nine compounds including six cycloartane glycosides cyclosieversiosides A, B, F, G, and H and astrasieversianin IX; β-sitosterol, β-sitosterol β-D-glucopyranoside, and D-3-O-methyl-chiro-inositol were isolated and identified from roots of Astragalus sieversianus Pall. (Leguminosae) growing in the Republic of Kyrgyzstan. Presented at the 6th International Symposium on the Chemistry of Natural Compounds (SCNC, Ankara, Turkey, June 28–29, 2005. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 253–256, May–June, 2008.     

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.     

The volatile constituents of <Emphasis Type="Italic">Dracocephalum kotschyi</Emphasis> oils

The chemical composition of the essential oils of Dracocephalum kotschyi (Lamiaceae) aerial parts, grown in Iran and obtained from three different methods, were determined by GC and GC/MS. Fifty-seven compounds (93.3%) in the hydrodistillate oil, 55 compounds (94.2%) in the steam distillate oil, and 34 compounds (98.4%) in the hydrolate were identified. The major compounds in the hydrodistillate oil were α-pinene (12.1%), methyl geranate (11.2%), β-ocimene (8.6%), and limonene (7.2%). α-Pinene (15%), methyl geranate (14.5%), limonene (11.2%), and β-ocimene (8.4%) were the most abundant components in the steam distillate oil. The percentages of geraniol (13%), trans-verbenol (11.6%), and terpinen-4-ol (11.2%) were more than other constituents in the hydrolate. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 35–37, January–February, 2007.     

GC-MS analyses of flower ether extracts of <Emphasis Type="Italic">Prunus domestica</Emphasis> L. and <Emphasis Type="Italic">Prunus padus</Emphasis> L. (Rosaceae)

Volatiles of fresh flowers of Prunus domestica L. and Prunus padus L. (their diethyl ether extracts) were analyzed by GC and GC-MS. 110 and 33 constituents were identified in P. domestica and P. padus extracts, respectively. 32 of the identified constituents were previously unreported as metabolites of taxa belonging to the genus Prunus. Six of them (4-methoxybenzyl palmitate, isoamyl stearate, isoamyl eicosanoate, isoamyl docosanoate and penta-O-acetyl-α- and β-D-glucopyranoses) are compounds reported for the first time from a natural source and one (isoamyl tetracosanoate) is a new compound in general. The major component of P. domestica extract was kaempferol (35.0 %), while P. padus extract was found to be rich in (Z)-8-hydroxylinalool (30.4 %), benzaldehyde (19.8 %) and 2-phenylethanol (15.1 %). Both extracts (P. domestica and P. padus) contained rather large amounts of shikimate metabolites (51.7 % and 39.1 %, respectively) and anther related odd-carbon numbered alkanes (23.2 % and 27.0 %, respectively). The observed differences between P. domestica and P. padus extracts corroborate the placement of P. domestica and P. padus in separate subgenera (Prunus and Cerasus, respectively) of the genus Prunus.     

Glycolipids from Leaves of <Emphasis Type="Italic">Eminium Lehmanii</Emphasis>

The quantitative composition of glycolipids from leaves of Eminium Lehmanii (Araceae) was established. It was shown that the predominant glycolipids were monogalactosyldiglycerides and digalactosyldiglycerides. The fatty-acid compositions of six glycolipids, of which digalactosyldiglycerides and sterylglycoside esters contained greater than 70% linoleic acid, were determined by GC. The main carbohydrate component of the leaf glycolipids was galactose. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 409–410, September–October, 2005.     

Composition of the essential oil of <Emphasis Type="Italic">Stachys acerosa</Emphasis> growing in central Iran

The essential oil of aerial parts of Stachys acerosa, which belongs to the Lamiaceae family and grows in central Iran, was obtained by a hydrodistileation method and analyzed by GC and GC-MS apparatus. Fourteen compounds representing 98.8% of the oil were identified. Among them N-methylisatin (30%), α-pinene (25%), sabinene (12.3%), and 2-hydroxyacetophenone (11.2%) were the major constituents of the oil, which was obtained in 0.1% yield. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 32–34, January–February, 2007.     

Chemical Composition of the Essential Oil of <Emphasis Type="Italic">Rhodiola quadrifida</Emphasis> from Xinjiang,China

The chemical composition of a hydrodistilled oil of Rhodiola quadrifida (Pall.) Fisch. et Mey. growing wild in Xinjiang Uygur Autonomous Region, China was analyzed by GC/MS. Twenty-three constituents were identified. The major components of the oil were hexadecanoic acid (45.39%), 9,12-octadecadienoic acid (33.38%), 9-hexadecenoic acid (3.08%), myristic acid (1.95%), a-terpineol (1.74%), and octadecanoic acid (1.07%). __________ Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 337–338, July–August, 2005.     

Mercaptan addition to 1-<Emphasis Type="Italic">O</Emphasis>-allyl-2,3,4,6-tetra-<Emphasis Type="Italic">O</Emphasis>-acetyl-<Emphasis Type="Italic">β</Emphasis>-D-galactopyranose

Addition of ethyl-, propyl-, and n-butylmercaptans to 1-O-allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose in the presence of benzoyl peroxide catalyst was studied for the first time. The products were 1-O-(3-ethylthiopropyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose, 1-O-(3-propylthiopropyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose, and 1-O-(3-butylthiopropyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose. Deacetylation of 1-O-(3-ethylthiopropyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose produced 1-O-(3-ethylthiopropyl)-β-D-galactopyranose. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 209–211, May–June, 2007.     

Composition of <Emphasis Type="Italic">Carlina acanthifolia</Emphasis> Root Essential Oil

The root of Carlina acanthifolia All. (Asteraceae) contained 1.0% of essential oil (expressed in g per 100 g of dried plant material). Using GC and GC/MS, nine components were identified (100% of total oil). The structure of benzyl 2-furylacetylene (carlina oxide), which is the principal component of the oil (91.5%), was spectrometrically identified. __________ Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 331–332, July–August, 2005.