Phytochemical analysis of the essential oil of Achillea millefolium L. from various European Countries

Variations in the essential oil composition of Achillea millefolium L. growing in Estonia and in other European countries, were determined. The oils were obtained in yields of 0.9-9.5 mL kg-1. A total of 102 components were identified. The quantitatively most important components of yarrow were sabinene, beta-pinene, 1,8-cineole, artemisia ketone, linalool, alpha-thujone, beta-thujone, camphor, borneol, fenchyl acetate, bornyl acetate, (E)-beta-caryophyllene, germacrene D, caryophyllene oxide, beta-bisabolol, delta-cadinol, chamazulene etc. Samples from Estonia contained high amounts of monoterpenes and chamazulene. High amounts of monoterpenes and chamazulene were also found in samples from Hungary, Greek, Moldavia, Latvia, Lithuania and Germany. The oils from France, Belgium, Russia, Armenia, Spain and Italy were rich in oxygenated monoterpenes and contained a little amount of chamazulene. The drugs from Greece, Estonia, Moldavia and Scotland were rich in sesquiterpenes. The Millefolii herba grown in Estonia conforms to the European Pharmacopoeia (EP) standards in the aspect of the essential oil contents.     

Composition of the essential oil of Salvia officinalis L. from various European countries

Variations in the essential oil composition of Salvia officinalis L. growing in Estonia and in other European countries were determined. The oils were obtained in yields of 2.2-24.8 mL kg(-1). In three samples, the content of essential oil did not conform to the EP standard (10 mL kg(-1)). Variations in the essential oil composition of sage were studied using capillary gas chromatographic methods. A total of 40 components were identified. The principal components in the sage oils were 1,8-cineole, camphor, alpha-thujone, beta-thujone, borneol, and viridiflorol. The chemotypes of sage were not determined in investigated samples. The concentration of the main compounds in the drugs cultivated in Estonia varied in about the same range as the concentrations of these compounds in the oils of drugs obtained from other countries. The comparatively high concentration of toxic thujones seem to be characteristic to sage leaves cultivated in Estonia.     

Essential oil composition of Foeniculum vulgare Mill. fruits from pharmacies in different countries

Variations in the essential oil composition of Foeniculum vulgare Mill. commercial fruits obtained from retail pharmacies in Estonia, Norway, Austria and Moldova and from a spice shop in Turkey were determined using capillary GC techniques. The essential oil content of all the samples was 5-51 mL?kg(-1) and between 22 and 51 mL?kg(-1) in fennel fruits bought from pharmacies. A total of 34 compounds were identified. The major component was trans-anethole (34.8-82.0%); the other principal compounds in oils were fenchone (1.6-22.8%), estragole (2.4-17.0%), limonene (0.8-16.5%), and cis-anethole (0.1-8.6%). The yield of essential oil (5.0?mL?kg(-1)) and content of trans-anethole was very low (34.8%) in the Turkish spice sample. Maximum yield of essential oil was found in fennel from Norway and Austria (50.7 and 50.5?mL?kg(-1), respectively); these samples were rich in fenchone (21.2% and 22.8%), but contained less trans-anethole (64.6-63.7) than samples from Estonia and Moldova (82.0% and 80.9%). The typical samples of sweet fennel (bought from Estonia and Moldova) and bitter fennel (from Norway and Austria) were found to conform completely or partially to EP standards, although fennel type was always not marked on the packages.     

Essential oil composition of Pimpinella anisum L. fruits from various European countries

Variations in the essential oil composition of Pimpinella anisum L. fruits obtained from different geographical areas of Europe were determined using capillary GC and GC-MS techniques. The essential oil content of the samples was 10.0-53.6 mL kg(-1) and did not confirm to the European Pharmacopoeia standard in 5 samples out of 14. A total of 21 compounds were identified and significant quantitative differences were observed among the samples. The major component was trans-anethole (76.9-93.7%); the other principal compounds in oils were gamma-himachalene (0.4-8.2%), trans-pseudoisoeugenyl 2-methylbutyrate (0.4-6.4%), p-anisaldehyde (tr-5.4%) and methylchavicol (0.5-2.3%). The highest content of trans-anethole (>90%) was found in the samples from Greece, Hungary, Scotland, Lithuania, Italy, and Germany (2 samples). Essential oil of aniseed from Estonia was rich in gamma-himachalene (8.2%) and trans-pseudoisoeugenyl 2-methylbutyrate (6.4%). The sample from France contained the highest amount of anisaldehyde (5.4%) comparing with other samples (0-3.1%). beta-Bourbonene and alpha-farnesene are determined in anise oil for the first time.     

Characterization and TLC-Bioautographic Detection of Essential Oils from Some Thymus Taxa. Determination of the Activity of the Oils and their Components Against Plant Pathogenic Bacteria

JPC – Journal of Planar Chromatography – Modern TLC - The chemical composition of the oils of four thyme (Lamiaceae) chemotypes (Thymus vulgaris L., Thymus serpyllum L., Thymus x...     

Comparison of antibacterial activity of natural and hydroformylated essential oil of Thymus capitatus growing wild in north Sardinia with commercial Thymus essential oils

Thymus capitatus growing wild in Sardinia showed different essential oil composition if grown surrounding Cagliari than in north Sardinia. Here we verify the composition and antimicrobial activity of the oil to make it suitable for the cosmetic and confectionery industries. With the aim of improving the scent and the antimicrobical activity of T. capitatus essential oil, a hydroformylation reaction was carried out to transform the unsaturated components of the oil into the corresponding aldehydes. The essential oil of T. capitatus exhibited a significant antibacterial activity (MIC 0.125-0.5 mg/mL), and was also found effective on C. albicans (MIC 0.125 mg/mL). After hydroformylation, several new irregular terpenoid aldehydes were detected. The perfume of the new terpenic-like aldehydes is very agreeable and, therefore, the acceptability of the aroma is remarkably improved, but the antimicrobial activity was not increased.     

Antimicrobial and antioxidant activities of essential oils of Satureja thymbra growing wild in Libya

The composition of essential oil isolated from Satureja thymbra, growing wild in Libya, was analyzed by GC and GC-MS. The essential oil was characterized by γ-terpinene (39.23%), thymol (25.16%), p-cymene (7.17%) and carvacrol (4.18%) as the major constituents. Antioxidant activity was analyzed using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. It possessed strong antioxidant activity (IC50 = 0.0967 mg/mL). The essential oil was also screened for its antimicrobial activity against eight bacterial and eight fungal species, showing excellent antimicrobial activity against the microorganisms used, in particular against the fungi. The oil of S. thymbra showed bacteriostatic activity at 0.001-0.1 mg/mL and was bactericidal at 0.002-0.2 mg/mL; fungistatic effects at 0.001-0.025 mg/mL and fungicidal effects at 0.001-0.1 mg/mL. The main constituents thymol, carvacrol and γ-terpinene also showed strong antimicrobial activity. The commercial fungicide bifonazole showed much lower antifungal activity than the tested oil.     

Comparative chemical, cytotoxicity and antileishmanial properties of essential oils from Chenopodium ambrosioides

In countries where leishmaniasis is endemic, there are not very many treatment alternatives and most options have problems associated with their use. Plants and their natural products constitute good sources of interesting lead compounds that could be potentially active against Leishmania. Chenopodium ambrosioides is a plant that is widely used in popular medicine and its antiparasitic effects have been documented, including the antileishmanial potentialities of Chenopodium oil. The objective of this study was to determine the chemical composition, in-vitro cytotoxicity and antileishmanial activity of essential oils extracted from C. ambrosioides, which received different treatments prior to extraction. The chemical characterization by GC-MS of the three essential oil samples showed similar composition and the major components were alpha-terpinene (17.0-20.7%), p-cymene (20.2-21.1%) and ascaridole (30.5-47.1%). The essential oils exhibited similar antileishmanial activities against intracellular amastigote form, with IC50 values between 4.7 and 12.4 microg/mL. However, a lower cytotoxicity was displayed by the essential oil extracted from fresh green vegetable material, which was statistically different (P < 0.05) from the other samples. This study demonstrated that the prior treatment of plant material did not interfere with the antiparasitic activity of essential oils from C. ambrosioides but did change their cytotoxicity, which should be taken into account in further studies.     

Identification of bioactive compounds in the leaves and stems of Aegopodium podagraria by various analytical techniques

The composition of essential oils of the leaves and stems of the Aegopodium podagraria growing wild in Estonia was determined using gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS). A total of 69 compounds representing over 95% of the total oil were identified. The oil from the stems of A. podagraria was rich in monoterpenes (92.0%). In the leaves oil mainly monoterpenes (43.8%) and sesquiterpenes (29.8%) were identified. The total and extractable content of six mineral elements and two trace elements of the leaves and stems of A. podagraria were determined by atomic absorption spectroscopy (AAS). Capillary electrophoresis (CE) was employed in the fingerprint analysis of A. podagraria extracts.     

Detailed analysis of the essential oil from Cistus albidus L. by combination of GC/RI, GC/MS and 13C-NMR spectroscopy

The composition of the essential oil of Cistus albidus (L.) obtained from plants growing wild in Provence (France) has been investigated using GC-RI (RI = retention indices), GC/MS and (13)C-NMR. Eighty-eight components were reported accounting for 81.8% of the essential oil. This essential oil was characterized by a high content of sesquiterpenes with alpha-zingiberene (12.8%), alpha-curcumene (7.7%), (E)-beta-caryophyllene (5.9%), alpha-cadinol (5.4%), alpha-bisabolol (4.1%), caryophyllene oxide (3.8%), allo-aromadendrene (3.4%), delta-cadinene (3.4%), and germacrene D (3.1%) being the main components.     

Chemical composition and antioxidant activity of the essential oil of Schisandra chinensis fruits

This study was designed to examine the composition and in vitro antioxidant activity of the essential oil of Schisandra chinensis fruits. Gas chromatography/mass spectrometry was used to determine the composition of the essential oil. Forty components were identified, representing 90.80% of the oil; ylangene (37.72%), β-himachalene (10.46%) and α-bergamotene (8.57%) were the main components. Antioxidant and radical-scavenging properties were evaluated by means of 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and β-carotene bleaching assay. In the DPPH assay, IC(50) value of the S. chinensis essential oil was determined as 4.17 mg mL(-1). In the β-carotene bleaching assay, the essential oil (1.0 mg mL(-1)) exhibited 25.89% inhibition against linoleic acid oxidation. In both systems, antioxidant capacity of butylated hydroxytoluene was also determined in parallel experiments.     

Essential oil composition of Valeriana officinalis L. roots cultivated in Iran. Comparative analysis between supercritical CO2 extraction and hydrodistillation

The composition of essential oil extracted from Valeriana officinalis L. roots growing wild in Iran was studied by hydrodistillation and supercritical CO2 extraction. Forty-seven components representing 89.3% and 35 constituents varying from 86.1% to 95.1% of the oil obtained by hydrodistillation and supercritical CO2 were identified, respectively. The major components in the extracted oil from supercritical CO2 were isovaleric acid (18.7-41.8%), valerenic acid (8.2-11.8%), acetoxyvaleranone (5.6-9.6%), (Z)-valernyl acetate (4.5-6.5%), bornyl acetate (2.3-7.7%) and valerenol (3.7-5.2%), whereas by hydrodistillation were bornyl acetate (11.6%), valerenic acid (8.0%), (Z)-valernyl acetate (7.9%) and acetoxyvaleranone (7.6%). The analysis of the extracts was performed by capillary GC and GC/MS.     

Application of PLE for the determination of essential oil components from Thymus vulgaris L

Essential plants, due to their long presence in human history, their status in culinary arts, their use in medicine and perfume manufacture, belong to frequently examined stock materials in scientific and industrial laboratories. Because of a large number of freshly cut, dried or frozen plant samples requiring the determination of essential oil amount and composition, a fast, safe, simple, efficient and highly automatic sample preparation method is needed.Five sample preparation methods (steam distillation, extraction in the Soxhlet apparatus, supercritical fluid extraction, solid phase microextraction and pressurized liquid extraction) used for the isolation of aroma-active components from Thymus vulgaris L. are compared in the paper. The methods are mainly discussed with regard to the recovery of components which typically exist in essential oil isolated by steam distillation.According to the obtained data, PLE is the most efficient sample preparation method in determining the essential oil from the thyme herb. Although co-extraction of non-volatile ingredients is the main drawback of this method, it is characterized by the highest yield of essential oil components and the shortest extraction time required. Moreover, the relative peak amounts of essential components revealed by PLE are comparable with those obtained by steam distillation, which is recognized as standard sample preparation method for the analysis of essential oils in aromatic plants.     

Chemical composition and biological activity of the volatile extracts of Achillea millefolium

In this study, flowering aerial parts of wild Achillea millefolium growing on the Mediterranean coast (Sardinia Island, Italy) and on the Atlantic coast (Portugal- Serra de Montemuro) were used as a matrix for supercritical extraction of volatile oil with CO2 (SFE). The collected extracts were analyzed by GC-FID and GC-MS methods and their composition were compared with that of the essential oil isolated by hydrodistillation. A strong chemical variability in essential oils depending on the origin of the samples was observed. The results showed the presence of two type oils. The Italian volatile extracts (SFE and essential oil) are predominantly composed by alpha-asarone (25.6-33.3%, in the SFE extract and in the HD oil, respectively), beta-bisabolene (27.3-16.6%) and alpha-pinene (10.0-17.0%); whereas the main components of the Portuguese extracts are trans-thujone (31.4-29.0%), trans-crhysanthenyl acetate (19.8-15.8%) and beta-pinene (1.2-11.1%). The minimal inhibitory concentration (MIC) and the minimal lethal concentration (MLC) were used to evaluate the antifungal activity of the oils against Candida albicans, C. tropicalis, C. krusei, C. guillermondii, C. parapsilosis, Cryptococcus neoformans, Trichophyton rubrum, T. mentagrophytes, T. mentagrophytes var. interdigitale, T. verrucosum, Microsporum canis, M. gypseum, Epidermophyton floccosum, Aspergillus niger, A. fumigatus and A. flavus. The oils showed the highest activity against dermatophyte strains, with MIC values ranging from 0.32-1.25 microL mL(-1).     

Determination of the Component Composition of Essential Oil of Thyme Species by the Method of Gas Chromatography

Abstract—A comparative study of the component composition of the essential oil of cultivars of Thymus serpyllum L. and similar kinds to expose marker connections for the authentication of raw material is conducted by the method of gas chromatography. In the essential oil of one of the specimen the propionates discovered are typical representatives of the Lamiaceae family.     

Influence of harvesting time on composition of the essential oil of Thymus capitatus (L.) Hoffmanns. & Link. growing wild in northern Sicily and its activity on microorganisms affecting historical art crafts

One of the main factors affecting historical art crafts material is the biodeterioration performed by bacteria and fungi, in archives, museums or private collections. Several microorganisms cause degradation to the natural organic material such as fibers, woods, and dyes as well as to stone objects. These alterations produce deterioration of physical, chemical, mechanical and esthetic properties. Consequently, in this publication, we report the high antibacterial and antifungal activities of wild thyme essential oil, oil that can be used as an alternative natural tool in the fight against microorganisms affecting historical art crafts.Essential oil of the Thymus capitatus growing wild in northern Sicily has been extracted by hydrodistillation from aerial parts collected at different growth times. The constituents of the essential oil have been characterized by gas chromatography (GC) and GC–mass spectrometry.Fifty-five compounds have been identified. Essential oils were characterized by a high content of carvacrol (81.2–14.2%), γ-terpinene (34.4–2.6%) and p-cymene (22.8–5.0%) of the total oil content. Essential oil yield and composition vary throughout the vegetation time of the plant. The best time to harvest this species of thyme, for phenol content, is during or immediately before the full bloom. The related oils (Tc2 and Tc3) showed a good antibacterial activity against Bacillus subtilis and Staphylococcus epidermidis and excellent antifungal properties against Fusarium oxysporum and Aspergillus niger.     

Chemical composition of bioactive pressurized extracts of Romanian aromatic plants

In this contribution, pressurized liquid extraction (PLE) has been employed to isolate bioactive compounds from three native Romanian plants, oregano (Origanum vulgare), tarragon (Artemisia dracunculus) and wild thyme (Thymus serpyllum). Different PLE conditions have been tested including extraction with water, ethanol and their mixtures in a wide range of extraction temperatures (50-200°C), and the antioxidant capacity of the extracts was measured using different assays (DPPH radical scavenging, TEAC assay and Folin-Ciocalteau assay to measure total phenols). Moreover, a complete chemical characterization by using LC-MS/MS was carried out to be able to correlate the bioactivity with the particular chemical composition of each extract and plant. The use of PLE with water as a solvent at the highest temperature tested (200°C) always provided the highest extraction yields for the three studied plants, being maximum for oregano (>60%). Besides, oregano's pressurized water extracts at lower temperatures (50°C) presented the highest content on total phenols (184.9 mg gallic acid/g extract) and the best antioxidant activities (EC(50) 6.98 μg/ml). In general, oregano extracts were the most active, followed by wild thyme extracts. The antioxidant capacity measured by DPPH assay was highly correlated with the amount of total phenols. Moreover, the use of a LC-MS/MS method allowed the identification of 30 different phenolic compounds in the different extracts, including phenolic acids, flavones, flavanones and flavonols, which have an important influence on the total antioxidant capacity of the different extracts.     

Essential oil composition and biological activity from Artemisia caerulescens subsp. densiflora (Viv.) Gamisans ex Kerguélen & Lambinon (Asteraceae), an endemic species in the habitat of La Maddalena Archipelago

The purpose of this study was to investigate the composition of the essential oil obtained from a population of Artemisia caerulescens subsp. densiflora growing in Razzoli, an island in the La Maddalena Archipelago (Sardinia, Italy). A. caerulescens sups. densiflora Viv. (Asteraceae), a wild herb, seldom studied in the Mediterranean, represents one of the many rare endemic species growing in North Sardinia. The essential oil composition was analysed by means of GC/MS analysis, which showed davana ethers as the major volatile components, accounting together for 17.5%, followed by (E)-nerolidol (4.5%), β-oplopenone (3.3%), cis-sabinene hydrate (5.2%) and terpinen-4-ol (4.7%). The oil was tested for antioxidant activity by means of DPPH test, inhibition of lipid oxidation test and hypochlorous acid test, which showed a quite interesting scavenger capacity. For the first time, we reported the cytotoxic activity of the essential oil of A. caerulescens subsp. densiflora, against three human tumour cell lines (A375, MDA-MB231 and HCT116), with IC₅₀ values in the range 5.20–7.61 μg/mL, which deserved further studies to support its use as chemopreventive agent. Finally, the antimicrobial activity of the essential oil, displayed on a panel of human pathogens, was very low.     

Antifungal activity and chemical composition of essential oils from Smyrnium olusatrum L. (Apiaceae) from Italy and Portugal

The essential oils and supercritical CO? extracts of wild Smyrnium olusatrum L. growing in Sardinia (Italy) and in Portugal were investigated. For the study, oils were isolated from total plant aerial part (umbels containing seeds). The content of β-phellandrene (67.3% vs. 42.7%) and α-pinene (31.9% vs. 1.2%), respectively, the main components of Portuguese and Italian essential oils, declined during the maturation stage of the umbels. Contrarily, some other important components, particularly curzerene, germacrene B, germacrone, alexandrofuran, 1-β-acetoxyfurano-4(15)-eudesmene and 1-β-acetoxyfurano-3-eudesmene, increased in fruiting umbels. The chemical composition of the Sardinian oil is rather different from those of other origin. The composition of the supercritical extracts and the essential oils is markedly different, particularly due to the high amount of furanosesquiterpenoids in the supercritical fluid extraction. The minimal inhibitory concentration (MIC) and the minimal lethal concentration were used to evaluate the antifungal activity of the oils against Candida albicans, Candida tropicalis, Candida krusei, Candida guillermondii, Candida parapsilosis, Cryptococcus neoformans, Trichophyton rubrum, Trichophyton mentagrophytes, Microsporum canis, Microsporum gypseum, Epidermophyton floccosum, Aspergillus niger, Aspergillus fumigatus and Aspergillus flavus. The oils were particularly active against dermatophyte strains and C. neoformans, with MIC values in the range of 0.32-0.64?μL?mL?1.     

The composition of the essential oils ofThymus marschallianus

The essential oil ofThymus marschallianus was obtained by steam distillation of freshly-gathered flowering plants growing at various heights of the Trans-Ili Ala-Tau range (Kazakhstan). The number of components detected was 49, of which 35 were identified. No appreciable differences in the composition of the essential oil with a change in the height of growth of the plant were observed. The essential oil ofTh. marschallianus and of a number of species growing in various countries have been compared.