GC-MS analysis of Ziziphora clinopodioides essential oil from North Xinjiang, China

The essential oils of Ziziphora clinopodioide Lam. from four different production areas (Banfang ditch; Altay mountains; Tuoli; Terks) were investigated. The oils were extracted by hydro-distillation and analyzed by gas chromatography-mass spectrometry (GC-MS). Seventeen constituents were identified in the essential oil from Banfang ditch, 20 in that from the Altay mountains, 12 in the Tuoli essential oil, and 9 in the Terks sample. The major components of the oils were pulegone (67.6%, 32.5%, 86.4%, and 82.1%) and p-menthanone (14.8%, 43.7%, 3.2%, and 8.2% from the Banfang ditch, Tuoli, Altay mountains, and Terks samples, respectively).     

Monoterpene glucosides from Ziziphora clinopodioides (Labiatae)

Three new monoterpene glucosides, ziziphoroside A (1), B (2), and C (3), together with fifteen known compounds were isolated from the whole herb of Z. clinopodioides. The structures of new compounds were determined primarily from 1D-, 2D-NMR and circular dichroism (CD) spectroscopic analyses. The isolated compounds were evaluated for their inhibitory activity against nitric oxide (NO) production by lipopolysaccharide (LPS) and interferon (IFN)-γ activated macrophages, RAW 264.7. Shizonepetoside A (8) and flavones (11, 12, 13) showed potent inhibitory activity against NO production.     

循环制备液相色谱分离芳香新塔花中的化学成分

建立了交替循环和直接循环液相色谱相结合的方法用于制备芳香新塔花中的化学成分.芳香新塔花样品经溶剂提取、柱色谱和中压制备色谱初步分离后得到芳香新塔花的不同馏分.以甲醇-水为流动相,利用双柱交替循环法对组分进行分离,同时,流动相经恒流泵循环输入色谱柱.以馏分Ⅰ和馏分Ⅱ为例,在混合循环模式下分离得到5个化合物.通过核磁共振对其进行鉴定,确定分别为乔松素-7-O-芸香糖苷、白杨素-7-O-芸香糖苷、金合欢素-7-O-芸香糖苷、云杉素和原儿茶酸.实验结果表明,该制备方法分离效率高,节省流动相,是分离天然产物的有效手段.     

Chemical composition and antimicrobial activity of essential oils from Centaurea pannonica and C. jacea

The chemical composition and antimicrobial activity of the essential oils obtained by hydrodistillation from Centaurea pannonica (Heufel) Simonkai and C. jacea L. (Asteraceae), were investigated. The essential oils were analyzed by GC and GC-MS. Forty five and twenty nine compounds were identified in the two oils, respectively. C. pannonica oil was rich in fatty acids (43.7%), with 9-octadecanoic acid (34.0%) and (Z,Z)-9,12-octadecadienoic acid (8.6%) as the major compounds. In contrast, the essential oil of C. jacea was dominated by oxygenated sesquiterpenes (43.2%), among which caryophyllene oxide (23.5%) and spathulenol (8.9%) were the major constituents. However, the oil was also characterized by an important fatty acid fraction (15.5%), with 9-octadecanoic acid (8.9%) and hexadecanoic acid (6.6%) being the main components. The antimicrobial activities of the essential oils were evaluated by the microdilution method against three Gram-positive and three Gram-negative bacteria, and one yeast. Both oils exhibited significant antimicrobial activity, especially against Gram-positive bacteria.     

Antibacterial activities of essential oils extracted from leaves of Murraya koenigii by solvent-free microwave extraction and hydro-distillation

Solvent-free microwave extraction (SFME) for the isolation of essential oil from leaves of Murraya koenigii L. (Rutaceae) has been compared with the conventional hydro-distilled oil (HD) in terms of yield, composition, antioxidant activity, and antibacterial activity against Listeria innocua. The yield of essential oil obtained from 30 min of SFME was similar to that of HD for 180 min. By GC-MS analysis, the major compounds of the essential oil extracted by SFME, which were obtained in somewhat lower amounts than in the essential oil obtained by HD, were alpha-copaene (44.3%), beta-gurjunene (25.5%), isocaryophyllene (12.1%), beta-caryophyllene (8.7%) and germacrene D (2.9%). The content of oxygenated terpenes, slightly higher for the SFME-essential oil (2.3%) than the HD-essential oil (1.4%), were much lower than that of nonoxygenated terpenes in both oils. DPPH radical scavenging activities of both essential oils were relatively low (10%-24%). Complete inhibition of growth of L. innocua was observed with both SFME and HD essential oils, at 400 and 600 microg/mL (minimum inhibitory concentration), respectively. The SFME-essential oil at 300 microg/mL provided 92% inhibition, indicating its potential as a natural antimicrobial agent.     

Chemical composition and possible in vitro antigermination activity of three Hypericum essential oils

The essential oils of Hypericum perforatum, H. perfoliatum and H. hircinum, growing in Southern Italy, were analyzed by GC and GC/MS. In the three oils, 111 compounds in all were identified: 53 for the oil of H. hircinum (93.7% of the total oil), 55 for H. perforatum (96.5% of the total oil) and 63 for H. perfoliatum (98.7% of the total oil). The major fraction of the essential oils of H. perforatum and H. hircinum was represented by sesquiterpene hydrocarbons, while the monoterpene alpha-pinene, and the phenol thymol were the most abundant compounds in the essential oil of H. perfoliatum. The oils were evaluated for their potential in vitro phytotoxic activity against germination and early radicle elongation of Raphanus sativus and Lepidium sativum. The germination of this latter was significantly inhibited by the essential oil of H. hircinum, at the highest doses tested, whereas radicle elongation of garden cress was significantly inhibited by the essential oils of H. perfoliatum and H. hircinum. The radicle elongation of radish was inhibited by the essential oil of H. hircinum to a major extent and by H. perforatum and perfoliatum in a minor measure.     

GC/MS analysis and antimicrobial activity of the essential oil of fresh leaves of Eucalytus globulus, and leaves and stems of Smyrnium olusatrum from Constantine (Algeria)

The essential oils of fresh leaves of Eucalyptus globulus L. (Myrtaceae), and leaves and stems of Smyrnium olusatrum L. (Apiaceae), obtained by hydrodistillation in a Clevenger-type apparatus, were analyzed by GC/MS. Twenty compounds were characterized, representing 98.3% of the essential oil of E. globulus, with 1,8-cineole (48.6%), globulol (10.9%), trans-pinocarveol (10.7%), and alpha-terpineol (6.6%) as main components, while thirty-three compounds were characterized, representing 94.3% of the essential oil of S. olusatrum, with sabinene (27.1%), curzerene (13.7%), methyl-1-benzyl-2-oxocyclooctane carboxylate (12.3%), alpha-pinene (7.2%), cryptone (7.1%) and beta-pinene (5.7%) as the major components. The essential oils of E. globulus and S. olusatrum were tested against a wide range of fungal and bacterial strains. Both oils showed significant antimicrobial activity.     

Composition and antimicrobial activity of the leaf and twig oils of Litsea acutivena from Taiwan

The chemical composition, and antimicrobial and anti-wood-decay fungal activities of the essential oils isolated from the leaves and twigs of Litsea acutivena of Taiwan were investigated. The essential oils from the fresh leaves and twigs were isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. Ninety-five and fifty-two compounds were identified in the leaf and twig oils, respectively. The main components of the leaf oil were gamma-patchoulene (11.0%), delta-cadinene (6.3%), trans-muurola-3,5-diene (5.9%), and beta-selinene (5.3%), whereas the main components of the twig oil were tau-cadinol (13.1%), beta-selinene (9.6%), trans-beta-ocimene (6.2%) and alpha-cadinol (7.7%). Bioactivity studies demonstrated that twig oil had excellent antimicrobial and anti-wood-decay fungal activities, superior to those of the leaf oil. For the antimicrobial and anti-wood-decay fungal activities of the twig oil, the active compounds were determined to be tau-cadinol and alpha-cadinol.     

Comparative analysis by gas chromatography-mass spectrometry of the essential oils from bark and leaves of Cedrelopsis grevei Baill, an aromatic and medicinal plant from Madagascar

The essential oils from bark and leaves of Cedrelopsis grevei Baill (Ptaeroxylaceae), an aromatic and medicinal plant from Madagascar, are widely used in folk medicine. These two commercially available oils have been examined separately by means of GC-MS. The oil constituents were identified according to their mass spectra and their relative retention indices determined on both polar and non-polar stationary phase capillary columns. A total of 55 compounds have been identified constituting 76.7% (bark) and 91.6% (leaves) of the volatile constituents. Both oils were found to have a similar composition; however the relative percentages of some compounds notably differed. The bark essential oil contained beta-pinene (17.1%), cis-sesquisabinene hydrate (12.8%) and caryophyllene oxide (7.0%) as the main components whereas the leaf essential oil was largely dominated by trans-beta-farnesene (35.6%); beta-pinene (12.8%), cis-sesquisabinene hydrate (9.8%) and ar-curcumene (8.6%) were also present as major components. As far as we know, this is the first report on the Cedrelopsis grevei bark and leaf essential oils which therapeutic properties may be attractive for aromatherapy.     

Chemical composition of essential oils from a multiple shoot culture of Telekia speciosa and different plant organs

The composition of essential oil from Telekia speciosa leaves, flowers, roots, stems and in vitro regenerated shoots was studied by GC-MS-FID leading to the determination of 112 compounds. The qualitative composition of the essential oil from the examined plant material was similar, whereas quantities of individual components of the oils varied widely depending on the kind of plant material. The most striking differences were observed between the oils produced by aerial and underground parts of the intact plant, as well as between oils produced by in vitro grown shoots and leaves of the intact plant. The main volatiles of leaf essential oil were: (E,E)-famesol (21.2%) and (E)-nerolidol (17.9%), while isoalantolactone was the predominant component of the root (62.3%) and flower oils (23.0%). Numerous thymol derivatives were also found, among them 10-isobutyryloxy-8,9-epoxythymol isobutyrate, which was one of the main components found in the flower oil (20.5%) and that from the in vitro cultures (20.2%).     

Comparison of volatile constituents, and antioxidant and antibacterial activities of the essential oils of Thymus caucasicus, T. kotschyanus and T. vulgaris

A comparison of the chemical composition, and antioxidant and antibacterial activities of the essential oils obtained from the aerial parts of Thymus caucasicus, T. kotschyanus, and T vulgaris was carried out. The oils, obtained by hydrodistillation, were analyzed by GC and GC/MS. Twenty, 29 and 22 compounds representing 94.8%, 96.6% and 98.2% of the essential oils of T. caucasicus, T. kotschyanus and T. vulgaris, respectively, have been identified. The oil of T. caucasicus was characterized by 1,8-cineol (21.5%), thymol (12.6%), beta-fenchyl alcohol (8.7%), nerolidol (7.8%), terpinolene (7.2%), alpha-pinene (7.0%) and myrcene (6.8%). In the oil of T. kotschyanus, carvacrol (24.4%), beta-caryophyllene (14.5%), gamma-terpinene (12.4%), alpha-phellandrene (10.8%), p-cymene (9.8%) and thymol (6.8%) were the predominant compounds, whereas the main components of T. vulgaris oil were thymol (43.8%), p-cymene (15.2%), germacrene-D (11.7%), terpinolene (3.4%), carvacrol (3.2%), beta-caryophyllene (2.8%) and alpha-thujene (2.2%). In all three plants oil, hydrocarbon monoterpenes predominated over sesquiterpenes. Antioxidant activities were assessed by determining IC50 values in the DPPH radical scavenging assay. Antibacterial activity was determined by measuring minimum inhibitory concentration (MIC) using the broth dilution method. The essential oils of T. caucasicus, T. kotschyanus and T. vulgaris showed free radical scavenging and antibacterial activity.     

Chemical composition and insecticidal activity against Sitophilus zeamais of the essential oils derived from Artemisia giraldii and Artemisia subdigitata

The aim of this research was to determine the chemical composition and insecticidal activity of the essential oils derived from flowering aerial parts of Artemisia giraldii Pamp. and A. subdigitata Mattf. (Family: Asteraceae) against the maize weevil (Sitophilus zeamais Motsch.). Essential oils of aerial parts of A. giraldii and A. subdigitata were obtained from hydrodistillation and investigated by GC and GC-MS. A total of 48 and 33 components of the essential oils of A. giraldii and A. subdigitata were identified, respectively. The principal compounds in A. giraldii essential oil were β-pinene (13.18%), iso-elemicin (10.08%), germacrene D (5.68%), 4-terpineol (5.43%) and (Z)-β-ocimene (5.06%). 1,8-Cineole (12.26%) and α-curcumene (10.77%) were the two main components of the essential oil of A. subdigitata, followed by β-pinene (7.38%), borneol (6.23%) and eugenol (5.87%). The essential oils of A. giraldii and A. subdigitata possessed fumigant toxicity against the maize weevils with LC50 values of 6.29 and 17.01 mg/L air, respectively. The two essential oils of A. giraldii and A. subdigitata also exhibited contact toxicity against S. zeamais adults with LD50 values of 40.51 and 76.34 μg/adult, respectively. The results indicated that the two essential oils show potential in terms of fumigant and contact toxicity against grain storage insects.     

Investigation of the chemical composition–antibacterial activity relationship of essential oils by chemometric methods

The antibacterial effects of Thymus vulgaris (Lamiaceae), Lavandula angustifolia (Lamiaceae), and Calamintha nepeta (Lamiaceae) Savi subsp. nepeta var. subisodonda (Borb.) Hayek essential oils on five different bacteria were estimated. Laboratory control strain and clinical isolates from different pathogenic media were researched by broth microdilution method, with an emphasis on a chemical composition–antibacterial activity relationship. The main constituents of thyme oil were thymol (59.95%) and p-cymene (18.34%). Linalool acetate (38.23%) and β-linalool (35.01%) were main compounds in lavender oil. C. nepeta essential oil was characterized by a high percentage of piperitone oxide (59.07%) and limonene (9.05%). Essential oils have been found to have antimicrobial activity against all tested microorganisms. Classification and comparison of essential oils on the basis of their chemical composition and antibacterial activity were made by utilization of appropriate chemometric methods. The chemical principal component analysis (PCA) and hierachical cluster analysis (HCA) separated essential oils into two groups and two sub-groups. Thyme essential oil forms separate chemical HCA group and exhibits highest antibacterial activity, similar to tetracycline. Essential oils of lavender and C. nepeta in the same chemical HCA group were classified in different groups, within antibacterial PCA and HCA analyses. Lavender oil exhibits higher antibacterial ability in comparison with C. nepeta essential oil, probably based on the concept of synergistic activity of essential oil components.     

Chemical constituents and antioxidant activity of essential oil and organic extract from the peel and kernel parts of Citrus japonica Thunb. (kumquat) from Iran

The constituents of essential oils and organic extracts from peel and kernels of Citrus japonica were analysed by GC and GC/MS. The content of essential oil in peel and kernel was 1.1 and 0.8% based on dry weight. The essential oil of C. japonica peel and kernel was characterised by a higher amount of limonene (51.0 and 47.1%) and germacrene D (12.1 and 6.3%), and the hexane extracts of its peel and kernel were characterised by a higher amount of dodecanol-1(12.9 and 20.8%) and linolenic acid (13.1 and 16.3%), respectively. The antioxidant activities of oils were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method. The results indicate that both oils from different parts of C. japonica possess considerable antioxidant activity. The fruit peel and kernel essential oil could thus be useful in the industries, chiefly in the food and pharmaceutical industries.     

A myristicin-rich essential oil from Daucus sahariensis growing in Algeria

The essential oils obtained by hydrodistillation from leaves and fruits of Daucus sahariensis Murb. were analyzed by GC/MS. The main constituents of the essential oil from the leaves were myristicin (34.3%), alpha-pinene (5.4%), cis-chrysanthenyl acetate (5.3%) and epi-alpha-bisabolol (4.8%), and those from the fruits myristicin (43.9%), alpha-pinene (13.1%), limonene (9.4%), and cis-chrysanthenyl acetate (7.4%). Myristicin, the main constituent of both essential oils, is generally absent in the oils from other Daucus species, permitting the hypothesis that this compound is a chemical marker of this Saharan species.     

Chemical composition and antioxidant, antimicrobial, and larvicidal activities of the essential oils of Annona salzmannii and A. pickelii (Annonaceae)

The essential oils from the leaves of Annona salzmannii and A. pickelii (Annonaceae) growing in Sergipe, northeastern region of Brazil, were obtained by hydrodistillation using a Clevenger-type apparatus, and analyzed by GC/MS and GC/FID. Thirty-four compounds were identified in the essential oil of A. salzmannii and twenty-seven in that of A. pickelii; sesquiterpenes predominated in both essential oils. Bicyclogermacrene (20.3%), (E)-caryophyllene (19.9%), delta-cadinene (15.3%), alpha-copaene (10.0%), and allo-aromadendrene (5.7%) were the main components of A. salzmannii, and bicyclogermacrene (45.4%), (E)-caryophyllene (14.6%), and alpha-copaene (10.6%) of A. pickelii. The essential oils showed significant antioxidant capacity in the ORAC(FL) and DPPH assays. The antimicrobial activity of these essential oils was also evaluated against bacteria and fungi, as well as the larvicidal activity against Aedes aegypti larvae.     

Composition of Satureja kitaibelii essential oil and its antimicrobial activity

The composition of the essential oil obtained by hydrodistillation from the aerial parts of Satureja kitaibelii from Rtanj mountain (Serbia), collected during three years, was studied. Thirty-nine components were identified in each sample of S. kitaibelii essential oil, representing about 87% of the oils. p-Cymene was the most dominant compound in all three oils (27.9%, 14.7% and 24.4%, respectively). The simple formulation of a lozenge with 0.2% of S. kitaibelii essential oil was prepared and the antimicrobial activity of the essential oil and the lozenge with essential oil was tested using a broth microdilution assay. Both essential oil and lozenge possessed strong antimicrobial activity with MIC values of 0.10-25 microg/mL, and 0.97-15.6 mg/mL, respectively.     

The essential oils of the aerial parts of two Hypericum taxa (Hypericum triquetrifolium and Hypericum aviculariifolium subsp. depilatum var. depilatum (Clusiaceae)) from Turkey

In this study, essential oil compositions of two Hypericum L. taxa (Hypericum triquetrifolium Turra. and Hypericum aviculariifolium Jaub. et Spach subsp. depilatum var. depilatum (Freyn et Bornm.) Robson) naturally grown in Turkey were determined using gas chromatography and gas chromatography-mass spectrometry systems. The essential oils were obtained by hydrodistillation from the aerial parts of plants. A total of 45 compounds were identified in the essential oils of H. triquetrifolium; 1-hexanal (18.8%), 3-methylnonane (12.5%) and α-pinene (12.3%). In this study, 41 components were identified in H. aviculariifolium subsp. depilatum var. depilatum oil; α-pinene (52.1%), germacrene D (8.5%) and β-pinene (3.6%) were the predominant constituents. The essential oil analysis showed that monoterpene concentrations were higher than that of the sesquiterpenes in both oils. The results were discussed in the meaning of the usefulness of these plants and their chemicals as natural products and potential usage in chemotaxonomy.     

Essential oil composition of two unique ginger (Zingiber officinale Roscoe) cultivars from Sikkim

Volatile oils from two most popular cultivars from Sikkim namely, Bhaisa and Majulay, were isolated, characterised by analytical GC and GC-MS. Sixty constituents accounting for 94.9% and 92.6% of the Bhaisa and Majulay oils were identified. The major compounds of Bhaisa oil were geranyl acetate (18.8%), zingiberene (16.3%) and geranial (8.2%) and those of Majulay oil were zingiberene (19.8%) and geranial (16.5%). Compared to other ginger cultivar oils, the Bhaisa oil had higher content of oxygenated compounds (43.1%). This is the first report on the essential oils from Sikkim ginger cultivars.     

Comparison of MAHD with UAE and Hydrodistillation for the Analysis of Volatile Oil From Four Parts of Perilla frutescens Cultivated in Southern China

Three different isolation techniques, specifically microwave-assisted hydrodistillation (MAHD), ultrasound-assisted extraction (UAE), and conventional hydrodistillation (HD) were employed to obtain essential oils from whole plants, leaves, roots, and stems of Perilla frutescens. The essential oils were analyzed using gas chromatography with flame ionization detection and gas chromatography with mass spectrometry. Variations in chemical composition were observed; these were attributed to differences in plant organs. Variations in the percentages of the main constituents of the oils extracted based on plant organ were irregular and affected the quantity and composition of the oils. Oil yields were affected by the method of extraction and extraction organ variation. The maximum volume of oil was extracted from leaves via MAHD and the minimum was extracted from roots via UAE. Oil yields ranged from 0.05% to 0.53%. The contents of essential oil varied significantly with the plant organ. In the essential oils of the plant parts studied were showed a predominance of oxygenated monoterpenes. Variation of extraction methods and organs may influence the oil components either qualitatively or quantitatively.