Headspace Solid Phase Microextraction for Terpenes and Volatile Compounds Determination in Mastic Gum Extracts,Mastic Oil and Human Urine by GC– MS

A reliable analytical method was developed, which is based on Headspace Solid Phase Microextraction (HS-SPME) and Gas Chromatography–Mass Spectrometry (GC-MS) for the detection of volatile components of the gum and the essential oil of Pistacia lentiscus var. chia, commonly known as mastic gum and mastic oil respectively. The conditions of the HS-SPME were optimized and aqueous-ethanolic extracts of mastic gum and solutions of mastic oil in ethanol-water were analyzed by GC-MS. Almost 26 volatile components in mastic gum and 34 in mastic oil were identified in the gum and the oil respectively. The major constituents of the mastic gum and the mastic oil were α-pinene (63% and 76%, respectively), β-myrcene (15% and 14%), β-pinene (4% and 4%), limonene (2.5% and 1.5%), and caryophyllene (5% and 1%). The quantitative determination of six of the aforementioned substances in multi-analyte standard solutions was achieved with good performance features. The repeatability (RSD%) was <4.2% and the limits of detection were 1.2 µg/L for α-pinene, 0.09 µg/L for β-pinene, 0.7 µg/L for β-myrcene, 0.02 µg/L for camphene, 0.02 µg/L for p-cymene, and 0.07 µg/L for α-terpineol. The HS-SPME/GC-MS procedure was successfully applied to samples of human urine samples after dietetic use of various mastic products such as mastic gum, mastic oil and Greek traditional highly viscous white mastic sweet. Traces of several constituents of mastic, such as α-pinene, β-myrcene, limonene, p-methyl anisole, terpinene, carveol, myrtenol, caryophyllene, α-caryophyllene, and so forth, were detected in the collected urine samples.     

Volatiles composition and antioxidant activity Inula oculus-christi L. from Serbia

Abstract

The chemical composition of the essential oil and the volatiles obtained by static headspace (HS) of Inula oculus-christi L. is presented. The GC-MS analysis of the hydrodistilled oil resulted in the identification of 90 components, representing 92.7% of the oil. The most abundant compounds were: caryophyllene oxide (9.8%), trans-longipinocarveol (9.2%), eucalyptol (7.3%) and intermedeol (6.2%). The major constituent of I. oculus-christi L. HS volatiles was eucalyptol (87.4%). The antioxidant activity was evaluated by four different methods: 2,2-diphenyl-1-picryl-hydrazylhydrate free radical assay (DPPH), 2,2-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method, total reducing power (TRP), ferric reducing antioxidant power (FRAP), and cupric reducing antioxidant capacity (CUPRAC). Total phenolic content in (TPC) examined oil was 177.95?µg GAE/mg oil. Radical scavenging potential of the oil was promising RSC-DPPH was 57.4% and RSC-ABTS was 82.7%.

     

Chemical composition and antimicrobial activity of the essential oils from flowers and leaves of Grindelia integrifolia DC

Essential oils from flowers and leaves of Grindelia integrifolia DC. were investigated for the first time in terms of chemical composition and antimicrobial activity. The GC-FID/MS analysis allowed for the identification of 58 and 72 volatiles, comprising 92.4 and 90.1% of the oils, respectively. The major components of the flower oil were α-pinene (34.9%) and limonene (13.1%), while myrcene (16.9%), spathulenol (12.3%), β-eudesmol (11.9%) and limonene (10.1%) dominated among the leaf volatiles. The antimicrobial activity, evaluated against 12 selected bacteria and fungus, was found moderate, with the strongest effect of both oils observed against C. albicans (MIC = MBC: 0.63 and 0.31 mg/mL for flower and leaf oil, respectively).     

Dynamic capillary diffusion system for monoterpene and sesquiterpene calibration: quantitative measurement and determination of physical properties

This article describes a method for preparation of low concentration gas standard mixtures of biogenic volatile organic compounds (BVOCs) emitted primarily by plants. A set of 10 plant volatiles including α-pinene, β-pinene, 3-carene, linalool, methyl salicylate, α-cedrene, β-caryophyllene, β-farnesene, aromadendrene and α-humulene was used in the study. Gas standard mixture of these compounds was generated using a capillary diffusion system (CDS). Diffusion coefficient (D) and saturation vapour pressure (p _s) data of these compounds were calculated from experimentally determined gas chromatographic retention indices (RI) and empirical relationships between D and p _s versus RI. A comparison of the calculated and measured concentrations of investigated compounds has proved that designed CDS can be successfully used for the proper quantification of BVOCs.     

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.     

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%).     

Determination of volatile organic compounds in the dried leaves of Salvia species by solid-phase microextraction coupled to gas chromatography mass spectrometry

Salvia spp. are used throughout the world both for food and pharmaceutical purposes. In this study, a method involving headspace solid-phase microextraction combined with gas chromatography–mass spectrometry was developed, to establish the volatiles profile of dried leaves of four Iranian Salvia spp.: Salvia officinalis L., Salvia leriifolia Benth, Salvia macrosiphon Boiss. and two ecotypes of Salvia reuterana Boiss. A total of 95 volatiles were identified from the dried leaves of the five selected samples. Specifically, α-thujone was the main component of S. officinalis L. and S. macrosiphon Boiss. (34.40 and 17.84%, respectively) dried leaves, S. leriifolia Benth was dominated by β-pinene (27.03%), whereas α-terpinene was the major constituent of the two ecotypes of S. reuterana Boiss. (21.67 and 13.84%, respectively). These results suggested that the proposed method can be considered as a reliable technique for isolating volatiles from aromatic plants, and for plant differentiation based on the volatile metabolomic profile.     

Insecticidal properties of essential oils against Tribolium castaneum (Herbst) and their inhibitory effects on acetylcholinesterase and adenosine triphosphatases

Essential oils from 20 Egyptian plants were obtained by using hydrodistillation. The chemical composition of the isolated oils was identified by gas chromatograph/mass spectrometer. Fumigant and contact toxicities of the essential oils were evaluated against the adults of Tribolium castaneum. In fumigation assays, the oil of Origanum vulgare (LC₅₀ = 9.97 mg/L air) displayed the highest toxicity towards the adults of T. castaneum. In contact assays, the oils of Artemisia monosperma (LC₅₀ = 0.07 mg/cm²) and O. vulgare (LC₅₀ = 0.07 mg/cm²) were the most potent toxicants against the adults of T. castaneum. Biochemical studies showed that the tested oils caused pronounced inhibition of acetylcholinesterase (AChE) and adenosine triphosphatases (ATPases) isolated from the larvae of T. castaneum. The oil Cupressus macrocarpa (IC₅₀ = 12.3 mg/L) was the most potent inhibitor of AChE, while the oil of Calistemon viminals (IC₅₀ = 4.4 mg/L) was the most potent inhibitor of ATPases.     

GC-MS Analysis of the Essential Oil from the Oleoresin of Pistacia atlantica var. mutica

The oleoresin of Pistacia atlantica var. mutica, growing in different regions of Iran, is a popular naturally occurring chewing gum and has been used traditionally in the treatment of peptic ulcer. The GC-MS analysis of the essential oil, obtained from steam distillation of the oleoresin of P. Atlantica var. mutica, has led to the identification and quantification of eleven terpenoids, -pinene (70%), -pinene (1.94%), 3-carene (0.2%), carveol (2.18%), epoxypinene (2.15%), limonene oxide (9%), myrtenol (5.31%), limonene (0.62%), citral (5.72%), -phellandrene (0.2%), and -myrcene (0.3%). The total amount of essential oil obtained was 22% v/w which is higher than any other species of the genus Pestacia.     

Isolation and Screening of Microorganisms for R-(+)-Limonene and (−)-β-Pinene Biotransformation

This work is focused on the biotransformation of R-(+)-limonene and (?)-β-pinene to bioflavor production. To carry out the present study, 405 microorganisms were tested for their ability to bioconvert the substrates. From the isolated microorganisms, 193 were selected in the prescreening using mineral medium for limonene degradation. At the screening step, eight strains were able to convert R-(+)-limonene and 15 to transform (?)-β-pinene, both in α-terpineol. The highest concentration in α-terpineol from R-(+)-limonene was about 3,450 mg/L for Penicillium sp. isolated from eucalyptus steam. From (?)-β-pinene, the highest product concentration of 675.5 mg/L was achieved using an Aspergillus sp. strain isolated from orange tree stem.     

Evaluation of chemical profile and antioxidant activity of Tripleurospermum insularum,a new species from Turkey

This article presents the very first phytochemical investigation on new species Tripleurospermum insularum Inceer &; Hay?rl?oglu-Ayaz. The volatile profile of odorous parts of the plant was analysed by GC/MS, and compounds were identified in headspace and essential oil obtained from aerial parts, representing 70.81% and 92.44% in total, respectively. The major volatiles were n-alkanes (38.43–59.22%), while essential oil was also rich in globulol (13.45%) and β-sesquiphellandrene (9.29%). The content of phenolic compounds in methanolic extract and oil was 3621.62 and 14.4 mg GAE/100 g of dry plant, respectively. Moreover, potential medicinal effects were found in mean of antioxidant activity of this plant measured by using two different assays: radical-scavenging activity and ferric-reducing activity. Samples revealed values ranging from 0.33 to 146.80 μmol TE/100 g for DPPH assay, and from 2.29 to 5414.17 μmol AAE/100 g for FRAP assay.     

Separation and purification of six compounds from the flowers of Cerasus yedoensis (Matsum.) by high-speed countercurrent chromatography in stepwise elution mode

Six compounds from the flower of Cerasus yedoensis (Matsum.) were successfully isolated by high-speed countercurrent chromatography (HSCCC) and preparative high performance liquid chromatography using stepwise elution with a pair of two-phase solvent systems composed of ethyl acetate–n-butanol–formic acid–water at volume ratio of 4:1.5:0.15:5 and ethyl acetate–ethanol–formic acid–water at volume ratio of 4:1:0.15:5 for the first time. This separation process produced (a) 141 mg of 1-O-caffeoyl-β-D-glucopyranoside, (b) 28 mg of p-coumaric acid glucoside, (c) 13 mg of chlorogenic acid, (d) 21 mg of quercetin-3-O-β-D-glucopyranoside, (e) 19 mg of kaempferol 3-O-β-D-glucopyranoside, and (f) 25 mg of caffeic acid from 400 mg of crude sample with the purities of 96.51, 98.82, 94.96, 99.01, 82.51, and 82.45%, respectively. MS, ¹H NMR, and ¹³C NMR analyses were used for the chemical structure identification.     

Chemical composition and biological activities of Iranian Achillea wilhelmsii L. essential oil: a high effectiveness against Candida spp. and Escherichia strains

In the case of Achillea wilhelmsii, 30 compounds were identified representing 94.48% of the total oil with a yield of 0.82% w/w. The major constituents of the oil were described as α-thujene (6.11%), α-pinene (5.11%), sabinene (5.23%), p-cymene (7%), 1,8-cineole (6%), linalool (10%), camphor (8.43%), thymol (18.98%) and carvacrol (20.13%). A. wilhelmsii oil exhibited higher antibacterial and antifungal activities with a high effectiveness against Escherichia coli and Candida albicans with the lowest minimum inhibitory concentration and minimum bactericidal concentration/minimum fungicidal concentration value (2 ± 0.0–2 ± 0.0 g/mL, 1 ± 0.5–1 ± 0.5 g/mL), respectively. Results showed that A. wilhelmsii oil exhibits a higher activity in each antioxidant system with a special attention for β-carotene bleaching test (IC₅₀: 19 μg/mL) and reducing power (EC₅₀: 10 μg/mL). Antioxidant activity-guided fractionation of the oil was carried out by TLC-bioautography screening and fractionation resulted in the separation of main antioxidant compounds which were identified as thymol (65%) and carvacrol (19%). In conclusion, these results support the use of the essential oil and its main compounds for their antioxidant properties and antimicrobial activity.     

Cationic grafting of olefins from PVC: The effect of reaction conditions

The cationic grafting of isobutylene, styrene, α-methylstyrene, and β-pinene from a poly(vinyl chloride) (PVC) backbone was investigated. Grafting-from was induced by Et₂AlCl in 1,2-dichloroethane and methylene dichloride solutions from 20 to −70 °C. The effects of temperature and proton trap [2,6-di-tert-butylpyridine (DtBP)] on grafting-from efficiency (G_eff), extent of grafting, branch length (molecular weight), and number of branches per PVC molecule were determined. Reducing the temperature invariably increased the G_eff and the molecular weight of polyisobutylene, polystyrene, poly(α-methylstyrene), and poly(β-pinene) branches attached to PVC. The magnitude of the effects was different with the various olefins and depended on the reaction conditions. The effect of DtBP was examined in the 5 × 10⁻⁴–4 × 10⁻³ mol/L range. By increasing the DtBP concentration the G_eff increased; however, the number-average molecular weight of the grafted branches decreased. The lengths of the grafted branches can be controlled, and G_eff's close to 100% were obtained. The fact that the proton trap reduced the molecular weights of grafted branches suggests that besides proton scavenging, DtBP may also abstract protons from the growing carbenium ion site. © 2001 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 1675–1680, 2001     

Chemical composition and antimicrobial activities of Perovskia artemisioides Boiss. essential oil

The Perovskia artemisioides Boiss. essential oil obtained by hydrodistillation method of flowers growing wild in the north of Iran. The study led to the identification of 29 compositions by a combination of HP-5 GC–FID and GC–MS analytical techniques. The constituents were identified in P. artemisioides essential oil with 1,8-cineole (29.9%), camphor (29.5%) and α-pinene (7.8%) as main constituents as well as δ-3-carene (5.1%), camphene (3.3%) and β-pinene (2.7%). The oil was identified by a much larger amount of monoterpenes (87.7%) and sesquiterpenes (6.3%). The results of antimicrobial activity exhibit that the extracted essential oil has presented a high inhibiting activity against five microbial strains up to 18 mm. Also, the MIC and MBC results displayed that Staphylococcus aureus, Escherichia coli and Salmonella typhi were inhibited by P. artemisioides essential oil. Therefore, determination of essential oils in this research showed a relatively similar pattern to those published for the other species of Perovskia.     

Densities and Refractive Indices of Binary Mixtures of Olive Oil + Alkanols at 298.15 K

Densities and refractive indices of mixing of olive oil with the alkanols: methanol, ethanol, 1-propanol, 2-propanol and 1-butanol, have been measured as a function of the composition at T = 298.15 K. Excess molar volumes, $ V_{\text{m}}^{\text{E}} $ , and deviation in refractive index, Δn _D, were calculated and correlated by a Redlich–Kister type function, to derive the coefficients and estimate the standard error. For mixtures of olive oil with alkanols, $ V_{\text{m}}^{\text{E}} $ is positive, except with ethanol and methanol where a sigmoidal variation is observed. Δn _D is positive over the entire range of mole fraction. The effect of chain length of the alkanols on the excess molar volumes and deviation in refractive index of the mixtures with olive oil are discussed.     

Physicochemical characteristics of the Lasiococca comberi Haines seeds

Physicochemical characteristics and fatty acid composition of Lasiococca comberi Haines (Euphorbiaceae), an endangered forest tree species, were determined for the first time. The oil, protein, crude fibre and carbohydrate contents in seeds were 41.5, 13.8, 22.2 and 11.6%, respectively. The refractive index, pH, specific gravity, saponification value, iodine value, peroxide value and p-anisidine value of seed oil were 1.4781, 6.4, 0.9, 178.4 mg KOH/g, 196 g I₂/100 g of oil, 5.1 mEq O₂/kg and 188.4, respectively. The predominant fatty acids were linolenic acid (65.3%), oleic acid (13.8%), linoleic acid (7.1%) and palmitic acid (5.3%). HPLC analysis revealed the presence of α-tocopherol (13.2 mg/100 g) and γ-tocopherol (6.3 mg/100 g) as the major tocopherols. The results indicated that L. comberi seed oil can be classified as drying oil having possible applications in different industries and as an important dietary source of omega-3 fatty acids.     

Chemical composition and antimicrobial activities of essential oil from Wedelia urticifolia growing wild in Hunan Province,China

The essential oil obtained from Wedelia urticifolia growing in Hunan Province, China, was analyzed for the first time by capillary GC and GC-MS. A total of 67 constituents, representing 98.68% in essential oil were identified. The major constituents of the oil were: α-pinene (8.85%), limonene (6.38%), carvacrol (6.15%), caryophyllene (6.08%), spathulenol (5.49%), sabinene (5.36%), camphor (4.34%). Antimicrobial potential of oil against bacterial strains (Pseudomonas aeruginosa, Escherichia coli and Bacillus subtilis, and Staphylococcus aureus), yeast strains (Hansenula anomala and Saccharomy cescerevisiae) and molds (Aspergillus niger, Chaetomium globosum, Mucor racemosus, and Monascus anka) was determined by disc diffusion method and broth micro dilution method, respectively. The oil exhibited promising antimicrobial effect as a diameter of zones of inhibition (16.8–24.9 mm). Minimum inhibitory concentration values of oil were ranged 62.5–1000 μg/mL.     

Phytochemical Investigation by Microwave‐Assisted Extraction of Essential Oil of the Leaves of Walnut Cultivated in Algeria

Walnut (Juglans regia L.) leaves are used traditionally as an herbal tea indicated for non‐insulin‐dependent diabetics. In recent years, the type‐II diabetes is occurring worldwide with increasing frequency. Thus, there is an urgent need to explore the new beneficial biomolecules on the human health. Our objective was to investigate, for the first time, the volatiles profile of Juglans regia L. leaves from Algiers region. The extraction of essential oil of fresh plant material was performed by microwave‐assisted hydrodistillation (MAHD), for the first time, a relatively recent method, then by the conventional hydrodistillation technique (HD) for comparison. The collected extracts were analyzed by GC‐FID and GC/MS using two capillary columns with different polarity. Extraction time of 1 h by MAHD provided higher yields (0.050±0.001% (w/w)) than by HD (0.030±0.006% (w/w)) after 3 h. A total of 38 compounds were identified using both techniques. Essential oils had similar qualitative but different quantitative composition in terms of chemical compounds. The MAHD method improved yield while reducing the extraction time. The sesquiterpenes were the dominant family in both MAHD and HD essential oils with β‐caryophyllene being the major constituent. Monoterpenes, including hydrocarbon and oxygenated, prevail in HD volatile fraction with β‐pinene and eucalyptol, respectively, as major components.     

Chemical composition and biological activities of essential oil from Filifolium sibiricum (L.) Kitam

The essential oil from Filifolium sibiricum (L.) Kitam were extracted using hydrodistillation and GC-MS was used to analyse the essential oil. The main components were espatulenol (8.55%), geranyl acetate (8.03%), caryophyllene oxide (5.47%), calamenene (4.79%), geraniol (4.28%), calamenene (4.53%), geraniol (4.06%), cedrene epoxide (3.23%), myrtenol (3.18%), transgeranylgeranio (3.13%), etc. The essential oil showed intensive inhibitory effects against MCF-7 with IC₅₀ level of 0.78 mg/mL, HepG-2 with IC₅₀ level of 0.44 mg/mL, SKOV-3 with IC₅₀ level of 0.27 mg/mL, BGC-823 with IC₅₀ level of 0.34 mg/mL. In the antibacterial test, the essential oil showed the significant antibacterial activities. The MIC and MBC values were 5.20 and 5.20 mg/mL against Staphylococcus aureus.