An investigation of the component composition of the essential oil of Monarda fistulosa

The composition of the essential oil of wild bergamot bee balm introduced into the Krasnodarsk Krai has been analyzed by chromatomass spectrometry. The essential oil contains 34 components of which the main ones are -pinene (3.5%), -pinene (2.9%), -terpinene (1.7%), p-cymene (32.5), an aliphatic aldehyde (6.3%), sabinene hydrate (1.9%), -caryophyllene (1.1%), the methyl ether of carvacrol (5.5%), citronellyl acetate (1.6%), thymol (12.6%), and carvacrol (24.0%). The compounds were identified on the basis of their mass-spectrometric characteristics and arithmetical retention indices.A. N. Severtsov Institute of Animal Evolutionary Morphology and Ecology, Academy of Sciences of the USSR, Moscow. All-Union Scientific-Research Institute of Drugs, Moscow. Translated from Khimiya Prirodnykh Soedinenii, Vol. 5, pp. 646–649, September–October, 1989.     

Essential oil ofPeucedanum oreoselinum fruits collected near Vilnius

Fruits ofPeucedanum oreoselinum (L.) Moench, were collected at three sites in 1995–1998 and contained 1.5–5.0% essential oil. Analyses were performed using GLC and GC-MS. The main component of the essential oil is limonene (44.1–82.4%). The majority of examined samples contained more limonene than has been reported in the literature. Only in sunny locations do plants synthesize significant quantities of γ-terpinene (12.2–17.5%) and β-pinene (8.5–14.5%). Small quantities of α-pinene are present in all studied samples of essential oil (4.0–8.3%). Monoterpenes comprise 97.1–98.6% of the essential oil. The remainder consists of sesquiterpenes. Institute of Chemistry, ul. Goshtauto, 9, Vilnius, Lithuania. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 743–745, November–December, 1999.     

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.     

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 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.     

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.     

Chemical variation in leaf oils of Pistacia chinensis from five locations in China

Hydrodistilled leaf oils of Pistacia chinensis Bunge from five locations in China were analyzed using GC/MS. A total of 58 compounds was identified in the oils, and a relatively high variation in their contents was found. The major compounds include β-phellandrene (0.54–53.86%), α-pinene (4.74–54.44%), β-pinene (0.49–42.90%), caryophyllene (5.64–20.01%), cis-ocimene (tr−43.93%), eudesmadiene (0–15.06%), and camphene (tr−20.57%). Cluster analysis classified the leaf oils into two chemotypes: one rich in α-pinene and β-pinene, and the other rich in β-phellandrene. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 341–343, July–August, 2006.     

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 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 <Emphasis Type="Italic">Pinus silvestris</Emphasis> essential oil from contaminated areas

The chemical composition of Pinus silvestris essential oil from contaminated areas was studied. An apparent effect of radionuclides and toxic elements on the biosynthesis of terpenoids in common pine essential oil was found. Increasing contamination apparently increased the content of sesquiterpenes and O-containing substances and decreased the content of monoterpenes in the essential oil. The contents of α-pinene, camphene, and limonene increased and those of 3-carene, terpinolene, and β-pinene decreased in the monoterpene fraction. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 47–49, January–February, 2007.     

Transannular cyclization of the E,E-germacradienolide hanphyllin

The results are reported of the interaction of the trans,trans-germacradienolide hanphyllin with m-chloroperbenzoic acid and with 50% sulfuric acid. This leads to a cyclization reaction with the formation of eudesmanolides: 1β-hydroxy-3-oxo-1,4,5,7α(H),6β(H)-eudesm-11(13)-en-6,12-olide, ridentin B, and 3β-hydroxy-5,7α(H),6β(H)-eudesma-4(15),11(13)-dien-6,12-olide; and also products of the opening of the lactone ring as a consequence of transesterification. The structures of the compounds obtained are discussed on the basis of spectral results (IR, PMR, and mass spectra) and of x-ray structural analysis. Institute of Organic Synthesis and Coal Chemistry, Kazakhstan Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 508–517, September–October, 1992.     

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.     

Essential oils of mongolian plants

1. The following compounds have been isolated by gas-liquid chromatography from the essential oil ofArtemisia rutifolia Steph. ex Spreng. growing in the Mongolian People's Republic and have been identified by their IR spectra: 1,8-cineole (35%), α-thujone andβ-thujone (11%), (+)-camphor (18%), (−)-α-terpineol (5%), and (−)-terpinen-4-ol (7%). By analytical gas chromatography α-pinene,β-pinene, camphene, limonene,β-phellandrene, and p-cymene have been identified in the hydrocarbon fraction. It has been shown that apart from compounds of a terpene nature the oil contains 4-phenylbutan-2-one, (±)-4-phenyl-butan-2-ol, and (±)-4-phenylbut-2-yl acetate. This is the first time that (±)-4-phenylbutan-2-ol and its acetate has been found in plant material.     

Comparative thermolysis of β-and α-pinenes in supercritical ethanol: the reaction characterization and enantiomeric ratios of products

The thermolysis of β-pinene and the co-thermolysis of an equimolar mixture of β-and α-pinenes in supercritical ethanol were carried out. The reaction of β-pinene affords β-myrcene as the major product (>70%). Considerable differences in the temperature dependence of the reaction rate were revealed for the transformations of β-pinene into β-myrcene and of α-pinene into limonene. The pre-exponential factors and the activation energies were calculated. The enantiomeric ratios of the thermolysis products of β-and α-pinenes and limonene were estimated. The starting monoterpenes do not undergo racemization during thermolysis. The thermolysis of enantiomerically pure α-pinene affords racemic (±)-limonene, whereas (−)-β-pinene gives (−)-limonene. The enantiomeric ratio in the latter remains equal to the enantiomeric purity of the starting β-pinene. Dedicated to the memory of Academician N. N. Vorozhtsov on the 100th anniversary of his birth. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1188–1192, June, 2007.     

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.     

Kinetics and thermodynamics of liquid phase isomerization of α- and β-pinene over Pd/C catalyst

The kinetics and thermodynamics of the liquid phase isomerization of an α- and β-pinene mixture on a Pd/C catalyst were studied. The effects of pinene concentration, catalyst particle size, stirring rate, reaction temperature (293–423 K) and hydrogen pressure (0.5–11 bar) on the rate of α- and β-pinene isomerization were investigated. The reaction rate of the α-pinene isomerization has the first order with respect to the α-pinene concentration and 0.5 order with respect to the hydrogen pressure. The thermodynamic parameters of the isomerization (Gibbs energy, reaction enthalpy and reaction entropy) and the equilibrium ratio of pinenes under the conditions studied were determined. The general scheme of the reaction mechanism of α- and β-pinene isomerization over the Pd/C catalyst was proposed.     

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.     

Anolide — A new guaianolide fromAchillea nobilis

The new sesquiterpene lactone anolide has been isolated from the epigeal part ofAchillea nobilis. From its spectral characteristics and the results of an x-ray structural investigation, the structure of 3α,4β-dihydroxy-1,5,7α(H),6β(H)-guaia-10(14),11(13)-dien-6,12-olide is proposed for anolide. Institute of Organic Synthesis and Coal Chemistry, National Academy of Sciences of the Republic of Kazakhstan, Karaganda. A. N. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 500–504, July–August, 1994.     

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.     

Molecular and crystal structure of the germacranolide argolide from Artemisia glabella

The new germacranolide argolide has been isolated from the epigeal part ofArtemisia glabella, and its structure has been shown by its conversion into oxopelenolide B. From the results of an x-ray investigation it is suggested that argolide has the spatial structure of 3-oxo-4α,7α,6β(H)-germacra-1(10),11(13)-dien-6,12-olide. Institute of Organic Synthesis and Coal Chemistry, Kazakh Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Organometallic Chemistry, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–657, September–October, 1991.