Composition of the essential oil of Stachys benthamiana Boiss. from the south of Iran

The chemical composition of the essential oil (EO) obtained from the aerial parts of Stachys benthamiana Boiss. was analysed by using GC and GC/MS. Thirty-three components were identified in the oil. β-Bisabolene (19.2%), humulene epoxide II (10.7%), epi-α-bisabolol (7.2%), (E)-γ-bisabolene (6.9%), n-decanal (6.8%) and caryophyllene oxide (6.6%), were the main compounds in the EOs. This is the first report on the different chemical compositions of S. benthamiana EOs from the south of Iran.     

Pesticides Residues Rapid Extraction from Panax Ginseng Using a Modified QuEChERS Method for GC–MS

A modified quick, easy, cheap, effective, rugged and safe (QuEChERS) rapid detection method followed by gas chromatography–tandem mass spectrometry (GC–MS) has been developed for the simultaneous determination of 42 pesticides in Panax ginseng. This method can be different from the other QuEChERS methods in the sense that it uses acetone and n-hexane solution rather than acetonitrile to extract and partition pesticides. This acetone, water and n-hexane solution QuEChERS method consists essentially of two steps: extraction/partitioning and purification. In step 1, P. ginseng was mixed with acetone, water and n-hexane solution, and then partitioned by vortex. In step 2, the top layer (n-hexane) was transferred into a centrifuge tube containing primary secondary amine, activated carbon and C₁₈ for purification. After the centrifuge supernatant was injected into GC–MS. The QuEChERS method was applied in P. ginseng detection and we confirmed that this method can easily extract various types of pesticides from P. ginseng. The rates of recovery for pesticides studied were satisfactory, ranging from 75.3 to 119.4 % for most of the pesticides with a relative standard deviation of less than 13 %. The LOQs ranged between 0.5 and 1.2 µg kg⁻¹. The modified QuEChERS method and GC–MS could enable complex pretreatment in P. ginseng analysis quickly and easily.

     

A new ester coumarin from Ferula Persica wild,indigenous to Iran

Ferula persica wild (Apiaceae) is a perennial herb indigenous to Iran. It has been used in folk medicine for treatment of diabetes, lowering of blood pressure and for antispasmodic, carminative, laxative and expectorant effects in central Iran. Dried ground roots of F. persica (150 g) were extracted sequentially with n-hexane, dichloromethane and methanol (MeOH), 500 ml each, using a Soxhlet apparatus. The n-hexane extract of the roots (3 g) was subjected to vacuum liquid chromatography on silica gel, eluting with solvent mixtures of increasing polarity: 100% n-hexane–ethyl acetate (EtOAc), to yield a number of fractions, Fraction 4 (80% EtOAc in n-hexane) was further analysed by preparative TLC (mobile phase was 12% acetone in chloroform) to yield a coumarin ester (10.1 mg, R_f = 0.31, blue florescent). The structure of the isolated compound was elucidated by spectroscopic means. The compound is 7-O-(4,8,12 -trihydroxy-4,8,12-trimethyl-tridecanoyl)-coumarin, named, ferulone C as a new natural product.     

Chemical composition and antimicrobial activity of the essential oil of Mentha mozaffarianii Jamzad growing wild and cultivated in Iran

The aerial parts of wild and cultivated Mentha mozaffarianii Jamzad were collected at full flowering stage from two provinces (Hormozgan and Fars) of Iran. The essential oils were extracted by a Clevenger approach and analysed using GC and GC–MS. The main components in wild plants were piperitenone (33.85%), piperitone (21.18%), linalool (6.89%), pulegone (5.93%), 1, 8.cineole (5.49%), piperitenone oxide (5.17%) and menthone (4.69%) and in cultivated plants, cis-piperitone epoxide (28.89%), linalool (15.36%), piperitone (11.57%), piperitenone oxide (10.14%), piperitenone (8.42%),1,8-cineole (3.60%) were the main constituents in essential oil. The in vitro antimicrobial activity of the essential oil of M. mozaffarianii was studied against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli and Candida albicans. The results of the bioassays showed that the oil exhibited high antimicrobial activity against all the tested pathogens.     

Phytochemical screening and biological activities of the oil components of Prunus domestica Linn

Phytochemical screening of three different oil fractions, obtained from n-hexane extract of Prunus domestica shoots were analyzed by GC and GC–MS. It resulted in the identification of 9, 16 and 24 compounds which representing 92.56%, 90.6% and 90.69% of these oil fractions, respectively. The main components identified from fraction 1, 2 and 3 were hentricontane (35.7%), ethyl hexadecanoate (21.7%) and linoleic acid (16.16%), respectively. Bioassay screening of oil showed moderate antibacterial activity against Salmonella group (Gram +ve and ?ve) by agar well diffusion method, moderate antifungal activity against Microsporum canis by agar tube dilution method and good antioxidant activity by DPPH radical scavenging method.     

Improvement of GC‐MS Analysis of Shahrbabak Ziziphora tenuior Essential Oil by Using Multivariate Curve Resolution Approaches

Essential oil of aerial parts of Ziziphora tenuior growing in Shahrbabak in central Iran are isolated by hydrodistillation. Due to complexity of essential oils, there are fundamental problems such as co‐elution in their direct gas chromatography‐mass spectrometry analysis. These problems can result in low similarity matches in MS library search, so that true identification and determination of individual components may fail. In the present work, each component was identified and determined using GC‐MS coupled with multivariate curve resolution (MCR) techniques. In this way, more information along with higher accuracy and precision can be extracted from pure experimental GC‐MS data. The number of identified components found increased from 37 in direct similarity search to 80 in GC‐MS/MCR method. To identify each individual component, similarity search and Kovat's retention index comparison were implemented. The results found showed that pulegone (38.3%), 3′,5′‐dihydroxyacetophenone (22.83%), isomenthone (7.06%), 2‐methyl‐5‐(1‐methylethyl)‐phenol (3.41%), limonene (2.59%) and 2‐acetyl‐4,4‐dimethyl‐cyclopent‐2‐enone (2.49%) were the most abundant components. The reported compounds accounted for 94.39% of total content of the essential oil. A characteristic feature of the Iranian Ziziphora tenuior is the absence of piperitenone in its constituents compared with the oil of other Ziziphora species from Turkey.     

Chemical composition of the essential oils and headspace volatiles of Ferulago sylvatica (Besser) Reichenb. from Serbia

Abstract

Chemical composition of the headspace volatiles and essential oils isolated from different parts of Ferulago sylvatica was determined by GC and GC/MS analyses. The results showed that headspace volatiles obtained from the aerial parts and roots were similar regarding the number of identified compounds and main components. However, essential oils obtained from different plant organs showed significant differences in chemical composition. Myrcene was the most abundant component of the inflorescences and shoots volatiles, while α-pinene make up over 50% of the root volatiles. Only three components were identified in the root essential oil with 2,3,6-trimethyl benzaldehyde (92.7%) as the main component. In the shoots sample the terpenoid fractions represented 56% of the oil, unevenly distributed between monoterpenoids and sesquiterpenoids with germacrene D (32.5%) recognized as the main constituent. On the other hand, more than 94% of the inflorescences oils were monoterpenoids with myrcene as the most abundant contributor (29.2%).     

Chemical Composition of the Volatile Oil from the Roots of Selinum tenuifolium Wall.

The essential oil from the underground parts of Selinum tenuifolium Wall. (Apiaceae) was extracted by hydrodistillation using a Clevenger‐type apparatus, and analyzed by GC/FID and GC/MS. Nine constituents, representing 97.7% of the total oil, were identified, five of which belong to the class of polyacetylenes. The structures of the compounds 1 – 5 were elucidated by using IR, MS, and ¹H‐ and ¹³C‐NMR data after purification by column chromatography. The major constituent detected was nona‐3,5‐diyne ( 1 ; 85.6% of the total volatiles), followed by nona‐3,5‐diyn‐2‐one ( 2 ), nona‐4,6‐diyn‐3‐one ( 3 ), nona‐3,5‐diyn‐2‐ol ( 4 ), and nona‐4,6‐diyn‐3‐ol ( 5 ), accounting for 3.0, 2.5, 2.2, and 3.1% of the total volatiles, respectively. The latter four polyacetylenes, 2 – 5 , were never reported in plants so far, and, therefore should be regarded as novel compounds.     

Reinvestigation of carvotanacetone after 100 years along with minor terpenoid constituents of Blumea malcolmii Hook. F. essential oil

Reinvestigation of essential oil constituents of Blumea malcolmii Hook. F. (Asteraceae) was carried out after 100 years using gas chromatography equipped with flame ionisation detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). Eighteen constituents, representing 99.2% of the total oil, were identified. The major compound was identified by GC/MS and NMR (¹H and ¹³C) as carvotanacetone (92.1%). The minor compounds of essential oil have also been identified for the first time in B. malcolmii. The oil was found to be rich in oxygenated monoterpene-type constituents (95.0%).     

Chemical composition of the essential oils from the aerial parts of two Malagasy endemic species (Apiaceae): Billburttia capensoides Sales & Hedge and Billburttia vaginoides Sales & Hedge

The chemical composition of twenty-five essential oil samples from the aerial parts of two Malagasy endemic species Billburttia capensoides Sales & Hedge and B. vaginoides Sales & Hedge, were investigated for the first time. Based on chromatographic profiles, three selected samples were investigated using GC(RI), GC-MS and ¹³C NMR. The content of the main components varied drastically from sample to sample: p-mentha-1,3,8-triene (0.2–52.7%), terpinolene (2.8–40.7%) and dill apiole (0.0–22.2%). Statistical analysis of the 25 oil compositions allowed the distinction of two well-differentiated groups. Samples of group I contained mainly p-mentha-1,3,8-triene while the Group II was dominated by terpinolene and dill apiole.     

Variation in essential oil composition of Teucrium hircanicum L. from Iran-A rich source of (E)-α-bergamotene

In present work, the chemical composition of the essential oils obtained from dried flowering aerial parts of Teucrium hircanicum L. (Labiatae) originated from ten wild populations in Iran was analyzed by a GC-FID and GC/MS system. The oil yields varied from 0.04% to 0.1%. A total of thirty-two compounds representing 67.6–97.7% of the oil were identified. The essential oil was found to be rich in sesquiterpene hydrocarpons (E)-α-bergamotene (17.5–86.9%) and (E)-β-farnesene (0.5–21.4%). Of the total identified compounds, sesquiterpene hydrocarpons (36.1–89.7%) were included the greatest essential oil fraction in all the populations, followed by oxygenated monoterpenes (2.2–21.6%), oxygenated sesquiterpenes (0.0–14.4%) and monoterepene hydrocarbons (0.0–9.5%). Hierarchical Cluster Analysis (HCA) and Principal Component Analysis (PCA) were used to distinguish any geographical variations, indicating that the clustering of populations is related to their geographic origin. According to the GC/MS analysis, two chemotypes consisting of (E)-α-bergamotene and (E)-α-bergamotene-(E)-β-farnesene were identified in the populations.     

Essential oil composition of Rydingia michauxii (Briq.) Scheen & V.A. Albert endemic of Iran

The chemical composition of the essential oil (EO) obtained from the aerial parts of Rydingia michauxii (Briq.) Scheen & V.A. Albert was analysed by gas chromatography and gas chromatography/mass spectrometry (GC/MS). Eighty components were identified in the oil with caryophyllene oxide (20.1%), trans-verbenol (10.2%), linalool (5.3%) and humulene epoxide II (4.6%) as main constituents. We reported here the chemical compositions of R. michauxii EOs from southern Zagros of Iran with a distinct chemical profile for the first time.     

Temperature-programmed desorption of n-hexane from hydrated HZSM-5 and NH4ZSM-5 zeolites

Temperature-programmed desorption coupled with mass spectrometer as a detector (TPD), IR and ¹³C NMR measurements are used to study the adsorption of n-hexane on hydrated HZSM-5 and NH₄ZSM-5 zeolites. The ¹³C NMR measurements show that n-hexane can access the pore structure of ZSM-5 zeolites previously saturated with water. TPD spectra of n-hexane are monitored in the temperature region 50–300°C, in the case of fully or partially hydrated samples; two-stage desorption of n-hexane is found. Simultaneous desorption of water and n-hexane in the same temperature region are found, in all investigated samples.     

Phenolic profile,antioxidant capacity and anti-inflammatory activity of Anethum graveolens L. essential oil

This study reports the chemical composition, antioxidant and anti-inflammatory properties of Anethum graveolens essential oil and its main compounds. The essential oil was obtained from the aerial parts of the plant by hydrodistillation and analysed by using GC/MS. α-Phellandrene (19.12%), limonene (26.34%), dill ether (15.23%), sabinene (11.34%), α-pinene (2%), n-tetracosane (1.54%), neophytadiene (1.43%), n-docosane (1.04), n-tricosane (1%), n-nonadecane (1%), n-eicosane (0.78%), n-heneicosane (0.67%), β-myrcene (0.23%) and α-tujene (0.21%) were found to be the major constituents of the oil. A. graveolens oil exhibit a higher activity in each antioxidant system with a special attention for β-carotene bleaching test (IC₅₀: 15.3 μg/mL) and reducing power (EC₅₀: 11.24 μg/mL). The TLC-bioautography screening and fractionation resulted in the separation of the main antioxidant compounds, which were identified as limonene (45%) and sabinene (32%). The essential oil and its main compounds exhibited a potent NO-scavenging effect and inhibited the expression of inducible NO synthase.     

Chemical composition and antibacterial activity of essential oil of Nepeta graciliflora Benth. (Lamiaceae)

The chemical composition of the essential oil obtained from aerial parts of Nepeta graciliflora was analysed, for the first time, by GC–FID and GC–MS. A total of 27 compounds were identified, constituting over 91.44% of oil composition. The oil was strongly characterised by sesquiterpenes (86.72%), with β-sesquiphellandrene (28.75%), caryophyllene oxide (12.15%), α-bisabolol (8.97%), α-bergamotene (8.51%), β-bisabolene (6.33%) and β-Caryophyllene (5.34%) as the main constituents. The in vitro activity of the essential oil was determined against four micro-organisms in comparison with chloramphenicol by the agar well diffusion and broth dilution method. The oil exhibited good activity against all tested organisms.     

Isolation and Identification of the Major Chemical Components Found in the Upper Parts of Teucrium Pofium Plants Grown in Khuzestan Province of Iran

Teucrium polium is a dwarf sub-shrub usually 30-60 cm high with many branches, which is fairly distributed throughout Iran, with its flowering being season mainly from April to July. The plant was collected during its flowering season in Baghmalek region in the North-East of Khuzestan province, Iran. After the identification of the genus, species and variety of the plant, the dried whole plant （flowers, fruits and the leaves） was steam distilled with different methods. The isolated essential oil was dried over anhydrous sodium sulphate and stored at 4-6 ℃. Analysis of the essential oil was carried out by GC-MS technique. At least 10 major components were identified （3-carene/α-pinene, β-phellandrene, limonene, germacrene, β-bourbonene, β-caryophylene, γ-muurolene, γ-elemene, spathulenol, β-eudesmol） （totally 97.02%）. Also, successive TLC and column chromatography of the essential oil resulted in the separation of four fractions. Based upon 1^H NMR, IR and mass spectra, the fractions with Rf=0.12 and 0.93 were determined as gualol and a mixture of α-pinene, β-phellandrene and limonene, respectively.     

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 oil constituents,phenolic content and antioxidant activity of Lavandula stricta Delile growing wild in southern Iran

Lavandula stricta belongs to the Lamiaceae family and is considered as an endemic medicinal plant in southern Iran. Essential oil composition, total phenolic content and antioxidant activity from two different populations of L. stricta were studied for the first time. A GC and GC/MS analysis of essential oil isolated from the aerial part of L. stricta identified 31 constituents; the major constituents were α-pinene (58.34–63.52%), linalool (8.85–9.36%), 3-methyl butyl 2-methyl butanoate (7.45–7.70%), sabinene (2.84–3.56%), limonene (2.87–3.21%) and myrcene (2.25%). The total phenolic content of methanolic extracts was determined with the Folin–Ciocalteu reagent and the antioxidant activity of methanolic extract and essential oil were determined with the 2, 2-diphenyl-1-picryl hydrazyl free radical scavenging assay, respectively. Total phenols varied from 61.05 to 64.45 mg GAE/g dry weight, and IC₅₀ values in the radical scavenging assay ranged from 334.11 to 395.23 μg/mL in methanolic extracts and 420–475 μg/mL in essential oil.     

Development of an efficient method for the preparative isolation and purification of chlorophyll a from a marine dinoflagellate Amphidinium carterae by high-speed counter-current chromatography coupled with reversed-phase high-performance liquid chromatography

In our research into chlorophylls of marine dinoflagellates, chlorophyll a was separated rapidly from the hexane extract of Amphidinium carterae in three steps. The first step was silica gel column chromatography, where elution was performed with 0–50% ethyl acetate in n-hexane. The second was high-speed counter-current chromatography using a two-phase solvent system consisting of n-hexane–ethyl acetate–methanol–water (5:5:5:1, v/v), and the third step was preparative reversed-phase high-performance liquid chromatography using a solvent system of acetone–water (89:11, v/v). HPLC analysis showed that the purity of chlorophyll a from the second step was over 83%, and after the third it was over 99%. Thirty milligrams of chlorophyll a was isolated from a crude sample of 250 mg of chlorophylls, and its structure was identified by analyzing its MS, ¹H NMR and ¹³C NMR spectra.     

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.