Variation in the volatile constituents of Artemisia annua var. CIM-Arogya during plant ontogeny

The essential oils yield and composition of the aerial parts of A. annua var. CIM-Arogya grown in Uttarakhand, India were analyzed and compared by capillary GC and GC-MS at different stages of development. The analysis led to the identification of 81 constituents forming 91.0%-97.1% of the essential oils compositions. The essential oil content of the aerial parts was found to vary from 0.3% to 0.7% at different stages of growth. A. annua crop harvested at full flowering and seed setting stage gave higher yield of essential oil (0.6%, 0.7%) than that harvested at pre flowering (0.5%), late vegetative (0.4%, 0.5%), mid vegetative (0.4%, 0.4%) and early vegetative stages (0.3%, 0.3%). The essential oils at different stages of growth showed monoterpenoids (38.5%-72.0%) and sesquiterpenoids (22.2%-48.2%) as major grouped constituents. The major constituents identified were camphor (22.8%-42.6%), 1,8-cineole (3.7%-8.4%), linalool (<0.1%-11.9%), beta-caryophyllene (2.0%-9.2%), (E)-beta-farnesene (1.3%-8.5%), germacrene D (0.5%-7.3%) and 1-epi-cubenol (0.7%-5.2%) in essential oil samples collected at different crop stages.     

Influence of growth phase on the essential oil composition and antimicrobial activities of Satureja hortensis

The variations in quantity and quality of essential oils (EOs) from the aerial parts of cultivated Satureja hortensis were determined at different stages of harvesting. The EOs of air-dried samples were obtained by hydrodistillation and analyzed by gas chromatography/mass spectrometry (GC/MS). The antimicrobial activity of the EOs was investigated by broth microdilution methods. The amount of EOs (w/w, %) were 2.3, 2.5, 2.0, and 1.8% at floral budding, full flowering, immature fruit, and ripened fruit stages, respectively. gamma-Terpinene was the major compound of the EO at all developmental stages, except the ripened fruit stage when it was replaced by carvacrol (46.4%). The EOs exhibited strong antibacterial activities against the tested bacteria. Moreover, the EOs either inhibited or killed the examined yeasts at concentrations ranging from 0.03-8.0 microL/mL. Considering the wide range of antimicrobial activities of the examined EOs, they might have potential to be used in the management of infective agents.     

Volatile constituent distribution of Prangos coryombosa Boiss at two stages of growth

The volatile constituents obtained by hydrodistillation of the aerial parts of Prangos coryombosa at the vegetative and flowering stages were analysed by GC and GC-MS. Twenty-one and 28 compounds were identified from the oils obtained from the plant's aerial parts at the vegetative and flowering stages, respectively. The oil from the vegetative stage was dominated by β-elemene (22%) and spathulenol (12.5%), whereas the oil from the flowering period was characterised by β-elemene (40.7%) and kessane (10.7%). The main compounds of the oil at the flowering stage were isolated by TLC and their structures were elucidated by (1)H and (13)C NMR. The results have ecological and taxonomical significance.     

Variation of bioactive substances in Hypericum montbretii during plant growth

The present study was conducted to determine phenologic and morphogenetic variation of chlorogenic acid and flavonoids, as rutin, hyperoside, apigenin-7-O-glucoside, quercitrin, quercetin and viteksin content of Hypericum montbretii growing in Turkey. Wild growing plants were harvested at vegetative, floral budding, full flowering, fresh fruiting and mature fruiting stages and dissected into stem, leaf and reproductive tissues and assayed for bioactive compounds by HPLC method. Accumulation of rutin and quercetin was not detected in plant parts of H. montbretii during plant growth. Chlorogenic acid and hyperoside content in whole plant was decreased linearly with advancing of development stages and reached their highest level at vegetative stage. On the contrary, apigenin-7-O-glucoside, quercitrin and viteksin content in whole plant increased during the course of seasonal development and the highest level of those compounds was observed at the stage of full flowering. Leaves did not produce apigenin-7-O-glucoside, while viteksin was not detectable in stem and reproductive tissues. Depending on development stages, reproductive parts had the highest level of apigenin-7-O-glucoside and leaves produced major amount of chlorogenic acid, hyperoside and viteksin whereas accumulation of quercitrin was prevailed in stem tissue. Such kind of data could be useful for elucidation of the chemotaxonomical significance of these compounds and medicinal evaluation of this species.     

Variation of hyperforin in Hypericum montbretii during its phenological cycle

Hypericum montbretii, a perennial herbaceous plant from Turkish flora has a great pharmaceutical potential with its well-documented chemical content. In the present study, morphogenetic and phenological variations of hyperforin were investigated in this species for the first time. Wild growing plants were harvested at vegetative, floral budding, full flowering, fresh fruiting, and mature fruiting stages and dissected into stem, leaf and reproductive tissues and assayed for hyperforin by HPLC method. Phenological changes in hyperforin content were found to be significant. After decreasing at floral budding slightly, hyperforin concentration in whole shoots increased with advancing of plant development and the highest level was reached at fresh fruiting. Among different parts of the plant, reproductive tissues namely green capsules and full opened flowers accumulated significantly higher amount of hyperforin when compared to stems and leaves. Such kind of data could be useful for elucidation of the chemotaxonomical significance of hyperforin and phytochemical evaluation of H. montbretii.     

Volatile constituents of Origanum vulgare L., 'thymol' chemotype: variability in North India during plant ontogeny

Essential oils derived from six different phenophases, namely early vegetative stage, late vegetative stage, early flowering stage, full flowering stage (FFS), late flowering stage and seed shattering stage of Origanum vulgare L. grown in Kumaon region of Uttarakhand, India were investigated by GC and GC-MS. A total of 38 constituents, representing 97.4-99.7% of the total oil composition, were identified. Major components of oils were thymol (40.9-63.4%), p-cymene, (5.1-25.9%), γ-terpinene (1.4-20.1%), bicyclogermacrene (0.2-6.1%), terpinen-4-ol (3.5-5.9%), α-pinene (1.6-3.1%), 1-octen-3-ol (1.4-2.7%), α-terpinene (1.0-2.2%), carvacrol (<0.1-2.1%), β-caryophyllene (0.5-2.0%) and β-myrcene (1.2-1.9%). Thymol, terpinen-4-ol, 3-octanol, α-pinene, β-pinene, 1,8-cineole, α-cubebene and (E)-β-ocimene were observed to be higher during FFS. The study showed that plant stage had a significant effect on the essential oil content and composition of O. vulgare grown in the hilly tracks of Northern India.     

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.     

Comparison of the components of the essential oils from leaves and fruits of Grammosciadium platycarpum

The composition of the hydrodistilled essential oils obtained from dried leaves and fruits of Grammosciadium platycarpum Boiss. & Hausskn. were determined by GC and GC/MS. Twenty-five compounds (87.0%) and sixteen constituents (96.2%) were identified in the leaf and fruit oils, respectively. Linalool (26.1 and 53.9%), (E,E)-α-farnesene (24.1 and 20.4% ) and (Z)-β-santalol (10.6 and 10.9%) were the major components in the leaf and fruit oils. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 559–560, November–December, 2006.     

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 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.     

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.     

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.     

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.     

Chemical diversity of the essential oils of twenty populations of Tanacetum polycephalum Sch. Bip. from Iran

Chemical diversity of the essential oils of twenty wild populations of Tanacetum polycephalum Sch. Bip., was investigated. The aerial parts of T. polycephalum were collected at full flowering stage from West Azerbaijan Province of Iran, air-dried; hydrodistilled to produce essential oils. The essential oils were analyzed by GC-FID and GC-MS. A total of forty compounds were identified accounting for 96.4–99.9% of the total oils. The most principal compounds were cis-thujone (0–82.3%), trans-thujone (0–79.8%), camphor (1.3–75.0%), 1,8-cineole (4.5–43.3%), borneol (1.0–36.2%) and bornyl acetate (0–26.8%). Hierarchical cluster analysis based on the percentages (>0.5%) of the essential oils components was carried out to determine the chemical diversity among the populations studied. The cluster analysis resulted in the identification of four main chemotypes namely: ‘camphor + 1,8-cineole’, ‘mixed’, ‘cis-thujone’ and ‘trans-thujone’.     

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.     

Variability of essential oils of Betonica officinalis (Lamiaceae) from different wild populations in Kosovo

The aerial parts and roots of Betonica officinalis were collected from three localities characterized by different ecological conditions to study the natural variability of the chemical composition of the essential oils in this plant. The leaves and inflorescences were collected during the flowering time, whereas the roots were collected at the end of the vegetative period. The plant material was dried at room temperature. The essential oils were obtained by micro-steam hydrodistillation and analyzed using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Overall, 69 constituents were identified in all localities and plant parts. The main compositions of the leaves in all localities were alpha-pinene, 1-octen-3-ol, beta-bourbonene, (E)-caryophyllene and germacrene D. The essential oil of the inflorescences was characterized by these main constituents: alpha-pinene, (E)-caryophyllene and trans-beta-farnesene. In all localities, the percentages of alpha-pinene and (E)-caryophyllene were higher in the inflorescences than in the leaves, whereas nonane was the main constituent in the roots.     

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     

Kinetic Study of Microwave Extraction of Essential Oil of Nigella sativa L. Seeds

The Nigella sativa L. is widely cultivated in the Algerian Sahara and primarily used for its health benefits. Extraction experiments were carried out by a microwave energy, performed at atmospheric pressure with a small quantity of water for 10 min. This method enabled a best yield (0.54–0.57%) and a high amount of the volatile fraction with a shorter extraction time and a reduction of energy consumption. The kinetic study of essential oils extraction was quantitatively studied. Thus, the qualitative and quantitative composition of the essential oils extracted for 10 min and in different periods was examined by capillary gas chromatography and by gas chromatography-mass spectrometry. The percentage of the main constituents such as p-cymene, thymoquinone, α-thujene, 4-terpineol and carvacrol was reported. The family classes present a significant variation according to the extraction time. Kinetic and extraction rate profile of microwave process (yield) showed that it is possible to reduce the extraction time.     

Chemical composition of essential oils from leaves, stems, flower heads and roots of Conyza bonariensis L. from Tunisia

The essential oils isolated at the flowering stage in spring, summer and autumn of the aerial and underground parts of Conyza bonariensis L. growing in Tunisia were analysed by GC and GC/MS; 143 constituents were identified, and among them 20 were major. The oils of C. bonariensis gathered in spring were rich in matricaria ester (1.2-67.3%), (Z)-nerolidol (0.3-19.9%) and caryophyllene oxide (0.8-14.3%). In the summer samples, the oils of C. bonariensis were rich in matricaria ester (1.6-76.4%), caryophyllene oxide (1.6-22.6%) and (E)-β-farnesene (1.1-22.7%). The main constituents in the autumn samples were matricaria ester (trace to 63.5%), geranyl acetone (0.0-25.3%), trans-α-bergamotene (0.0-24.3%) and limonene (2.7-15.3%). The oils showed significant variation among the seasons. Remarkable differences were found between the constituent percentages of the different studied organs. The C. bonariensis sample from Tunisia was a matricaria ester chemotype and was quite different from the samples of other countries of origin.     

Analysis of essential oils from Voacanga africana seeds at different hydrodistillation extraction stages: chemical composition,antioxidant activity and antimicrobial activity

In this study, essential oils from Voacanga africana seeds at different extraction stages were investigated. In the chemical composition analysis, 27 compounds representing 86.69–95.03% of the total essential oils were identified and quantified. The main constituents in essential oils were terpenoids, alcohols and fatty acids accounting for 15.03–24.36%, 21.57–34.43% and 33.06–57.37%, respectively. Moreover, the analysis also revealed that essential oils from different extraction stages possessed different chemical compositions. In the antioxidant evaluation, all analysed oils showed similar antioxidant behaviours, and the concentrations of essential oils providing 50% inhibition of DPPH-scavenging activity (IC₅₀) were about 25 mg/mL. In the antimicrobial experiments, essential oils from different extraction stages exhibited different antimicrobial activities. The antimicrobial activity of oils was affected by extraction stages. By controlling extraction stages, it is promising to obtain essential oils with desired antimicrobial activities.