Isolation and identification of flower oil components from four <Emphasis Type="Italic">Staphylea</Emphasis> L. species

Chemical composition of the hydrodistilled volatile fraction from flowers of four Staphylea L. species (Staphylea colchica Stev., Staphylea elegans Zab., Staphylea holocarpa Hemsl., Staphylea pinnata L.) was determined by the GC/MS method. Compounds in fresh and dried flowers (stored for 1 year) were determined. Mostly, structures of different oxygenated aliphatic hydrocarbons in all four species were found. Different aldehydes, ketones, esters of higher fatty acids, and hexadecanoic acid were identified, with dominating content of tricosane, hexadecanoic acid and also of heneicosane, pentacosane, heptacosane, and nonacosane. In S. pinnata L. (fresh flowers) some nonaliphatic hydrocarbons, and in S. holocarpa Hemsl. (fresh flowers) esters of higher fatty acids were found.     

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 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.     

Chemical Composition of the Essential Oils of <Emphasis Type="Italic">Bunium elegans</Emphasis> and <Emphasis Type="Italic">Bunium caroides</Emphasis>

Analyses of the essential oils of Bunium elegans (Fenzl) Freyn and B. caroides (Boiss.) Hausskn. ex Bornm., using GC, GC/MS, and¹³ C-NMR spectroscopy resulted in identification of their chemical constituents. The oils of both species contain mainly the sesquiterpene hydrocarbons germacrene-D and E-caryophyllene, which amounted to 24.1% and 38% for B. elegans and 22.1% and 26.6% for B. caroides respectively. The oil of B. caroides contained the monoterpenes α-pinene and Z-β-ocimene in 4.1 and 5.9% respectively, while traces of monoterpenes were detected for B. elegans. On the other hand, in B. caroides the phenylpropanoid derivatives asaricin (7.5%) and dillapiole (10.2%) were among the major constituents. __________ Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 335–336, July–August, 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.     

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.     

Components of <Emphasis Type="Italic">Artemisia pontica</Emphasis>

Chemical components from the aerial part of the Kazakhstan population of Artemisia pontica, from which the rarely encountered flavonoids 7-O-methyl- and 4′,7-di-O-methyl-esters of apigenin were isolated for the first time, were identified. The complete chemical composition of the essential oil was established using GC-MS.__________Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 143–145, March–April, 2005.     

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.     

Synthesis of 4<Emphasis Type="Italic">E</Emphasis>,7<Emphasis Type="Italic">Z</Emphasis>-tridecadien-1-ylacetate,a component of the <Emphasis Type="Italic">Phthorimaea opercucella</Emphasis> sex pheromone

A new synthetic approach to 4E,7Z-tridecadien-1-ylacetate, a component of the Phthorimaea opercucella (Zeller) potato moth sex pheromone, was developed using a highly stereoselective Claisen rearrangement and Wittig reaction. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 235–236, May–June, 2007.     

Chemical Composition of the Essential Oil of <Emphasis Type="Italic">Salvia macilenta</Emphasis> from Iran

The hydrodistilled essential oil composition from the aerial parts of Salvia macilenta (Lamiaceae) from Iran was analyzed by GC and GC-MS. The oil analysis confirmed the characterization of thirty-one compounds, accounting for 99.4% of the total oil. Analysis of the oil showed that the oil of S. macilenta was rich in monoterpene hydrocarbons with a-pinene (60%) as the main component followed by γ-elemene (6.1%), thymol (5.2%), elemol (4.7%), and β-caryophyllene (4.1%).__________Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 136–137, March–April, 2005.     

<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.     

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.     

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.     

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.     

Structure of a New Diterpene Alcohol from <Emphasis Type="Italic">Pinus sibirica</Emphasis> Buds

The newditerpene alcohol (1) in addition to the known metabolitesisoagatholal (2) and β-sitosterol glucoside (as the tetraacetate) (3) were isolated from buds of Siberian pine. The structure of the new compound was established as abieto-8(14)-en-18-ol 9α,13α-endoperoxide. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 343–344, July–August, 2005.     

Aryltetralin Lignans from <Emphasis Type="Italic">Linum mucronatum</Emphasis> Bertol. ssp. <Emphasis Type="Italic">mucronatum</Emphasis>

The dried and aerial part of Linum mucronatum ssp. mucronatum was analyzed by gas chromatography-mass spectrometry (GC-MS). Two aryltetralin lignans, podophylloyoxin, 6-methoxypodophylloyoxin, and β-peltatin, were identified. This is the first report of the analysis of L. mucronatum ssp. mucronatum.__________Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 24–25, January–February, 2005.     

Synthesis of 2,3-<Emphasis Type="Italic">cis</Emphasis> Stereomeric Emetamines <Emphasis Type="Italic">via Reissert</Emphasis> Compounds

Summary. Alkylation of Reissert compounds with certain benzoquinolizinone derivatives followed by hydrolytic cleavage afforded the core of the title compounds in a two step sequence. Finally, the lactam intermediates were reduced with DIBAH giving the target compounds, the structural and stereochemical assignments of which were achieved by ¹³C NMR spectroscopy. Part of PhD thesis, LMU München, D     

Reaction sites of <Emphasis Type="Italic">N,N′</Emphasis>-substituted <Emphasis Type="Italic">p</Emphasis>-phenylenediamine antioxidants

The geometries of N,N′-diphenylbenzene-1,4-diamine (DPPD), N-phenyl-N′-(1-phenylethyl)benzene-1,4-diamine (SPPD), N-(4-methylpentan-2-yl)-N′-phenylbenzene-1,4-diamine (6PPD), N-propan-2-yl-N′-phenylbenzene-1,4-diamine (IPPD), N-(2-methoxybenzyl)-N′-phenylbenzene-1,4-diamine (MBPPD), and N-phenyl-N′-(2-phenylpropan-2-yl)benzene-1,4-diamine (CPPD) as well as of their dehydrogenation products were optimized by the semiempirical AM1 method. The results support the idea of stable N_B=C_X structures formation during the consecutive dehydrogenation of SPPD, 6PPD, IPPD, and MBPPD antioxidants. The biradicals formed during the second step of dehydrogenation of substituted phenylenediamines might be important for their antioxidant effectiveness. Dedicated to Professor Vladimír Kvasnička, DrSc., in honour of his 65th birthday     

Chemotaxonomy of <Emphasis Type="Italic">Ballota</Emphasis> Species

Sixteen taxa of Ballota were investigated by analyzing the contents of diterpenoid and flavonoid compositions, and the relationships were compared with their morphological properties. HPLC chromatograms of diterpenoids and flavonoids from acetone extracts of sixteen Ballota taxa revealed the presence of thirteen compounds. Isolated compounds from Ballota species were evaluated by the unweighted pair-group arithmetic average (UPGMA) clustering method. B. glandulosissima is distinct from all other taxa in the dendogram, and this species is morphologically different from other taxa by having a high number of glandular hairs. The second group is composed of B. saxatilis ssp. saxatilis and B. inaequidens; these two species are in close kinship as evidenced by their morphology (similar calyx shape). In the latter clusters at most, the affinities among taxa, as suggested by diterpenoid and flavonoid pattern, are only partially congruent with affinities based on other evidence. In general, morphologic, anatomic characters, distributions, and habitats are not concordant with the clusters. Also, no concordance was found between the sections, phylogenetic order [1], and those of the groups formed by cluster analyses.__________Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 242–244, May–June, 2005.     

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.