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.     

Characteristics of fatty acids and essential oil from sweet fennel (Foeniculum vulgare Mill. var. dulce) and bitter fennel fruits (F. vulgare Mill. var. vulgare) growing in Turkey

Oil content in sweet and bitter fennels was obtained 12.22% and 14.41%, respectively. The C(18:1 c6), C(18:2), C(18:1 c9) and C(16:0) acids corresponding to approximately 97% of total oil was recorded as principal fatty acids. The ratios of essential oil from sweet and bitter fennels were found similar (average 3.00%). trans-Anethole, estragole and fenchone were found to be the main constituents in both fennels. The compound with the highest value in the two oil samples was trans-anethole as 95.25% (sweet) and 75.13% (bitter). While estragole was found in bitter fennel oil in a remarkable amount (15.51%), sweet fennel oil contained small amounts of estragole (2.87%). Fenchone was found <1% in sweet and approximately 5% in bitter fennel. p-Anisaldehyde in bitter fennel essential oil, and alpha-pinene and gamma-terpinene in sweet fennel essential oil were not recorded, and these compounds were found very low or <1%.     

Chemical composition and larvicidal activity of Algerian Foeniculum vulgare seed essential oil

A laboratory study was conducted to determine the effect of three extraction parameters (soaking time, extraction time and the ratio of solid to liquid) on the yield and chemical composition of Foeniculum vulgare seeds essential oils. The bioactivity of the essential oil extracted for the optimum extraction parameters was assessed against Culex pipiens mosquito. F. vulgare essential oil composition included large amounts of phenylpropanoids. Through an extraction time of 6 h and a ratio solid to liquid of 300 g/L we can get over than 72% of trans-anethol without soaking the seeds. With bioassays, essential oils showed different activities on C. pipiens larvae and pupae. Results show that a concentration at 40 mg/L was sufficient to register 50% mortality for the second instars larvae and this, after 2 h exposition time. Moreover, concentration at 60 mg/L ensured after 4 h exposition time 90% mortality for the fourth instars larvae. However, pupae needed 24 h exposition time to show promising mortalities when using concentration at 200 mg/L. Even if laboratory bioassays are only the first step towards the use of essential oils in practical applications, these substances represent a potential alternative to chemical insecticides in some markets.     

Hydrodistillation–Headspace Solvent Microextraction: An Efficient Method for Analysis of the Essential Oil from the Seeds of Foeniculum vulgare Mill.

Hydrodistillation–headspace solvent microextraction (HD–HSME) has been used for isolation and preconcentration of the essential oil from the seeds of Foeniculum vulgare Mill. The effect on extraction efficiency of different conditions, for example sample mass, extraction time, microdrop volume, and choice of solvent, was studied and all were optimized. The results were compared with those from hydrodistillation, as reference method. Fourteen compounds were identified; the main components were trans-anethole (70.4%), fenchone (9.3%), and p-allylanisole (8.8%). The results were in good agreement with those obtained by hydrodistillation.     

小茴香超临界CO_2萃取产物脂肪酸成分分析

通过脂肪酸的衍生化处理，再利用色谱（GC）和色谱一质谱（GC－MS）等分析手段，对小茴香超临界CO2萃取产物的脂肪酸成分进行了剖析，共鉴定出九种脂肪酸，其中，十八碳一烯酸、十八碳二烯酸和棕榈酸是其主要成分，分别占脂肪酸总量的75．12％、15．18％和5．34％．     

小茴香不同炮制品活性成分的动态变化研究

按《中华人民共和国药典》分别对净制后的小茴香进行清炒、盐制、醋制、酒制和姜汁制,并提取出活性挥发油,采用气相色谱-质谱联用仪和薄层色谱对提取物进行分析。小茴香经不同辅料炮制后挥发油含量显著降低;与生品相比,炮制品均含有相同的主要活性成分,其中反式-茴香脑含量最高,顺式-番桧烯水合物、顺式-罗勒烯、α-松油烯、4-松油烯、对位-烯丙基茴香醚和枯敬醛为首次在小茴香药材中检测到;鉴定出的24种化合物经不同方法炮制后含量均发生了明显变化,且发生了相应的转化,这是导致不同炮制品具有不同药性和功效的重要原因。     

Antimycobacterial activity of constituents from Foeniculum vulgare var. dulce grown in Mexico

Bioassay guided fractionation of an antimycobacterial extract of Foeniculum vulgare var dulce (Apiaceae) led to the isolation and characterization of 5-hydroxyfurano-coumarin. The chemical structure of this compound was elucidated by 1H and 13C (1D and 2D) Nuclear Magnetic Resonance (NMR) spectroscopy. In addition, the active fractions were analyzed by GC-MS and seventy eight compounds were identified; the major compounds were 1,3-benzenediol, 1-methoxycyclohexene, o-cymene, sorbic acid, 2-hydroxy-3-methyl-2-cyclopenten-1-one, estragole, limonene-10-ol and 3-methyl-2-cyclopenten-1-one. Twenty compounds identified in the active fractions were tested against one sensitive and three MDR strains of Mycobacterium tuberculosis using the Alamar Blue microassay. Compounds that showed some degree of antimycobacterial activity against all strains tested were the following: linoleic acid (MIC 100 μg/mL), oleic acid (MIC 100 μg/mL), 1,3-benzenediol (MIC 100-200 μg/mL), undecanal (MIC 50-200 μg/mL), and 2,4-undecadienal (MIC 25-50 μg/mL), the last being the most active compound. To our knowledge, this is the first report of the presence of 5-hydroxy-furanocoumarin in F. vulgare.     

Essential oil composition of the different parts of Eryngium bourgatii Gouan from Spain

The essential oil extracted from the different parts of Eryngium bourgatii Gouan: stems + leaves (E.b.SL), inflorescences (E.b.I) and roots (E.b.R), have been extracted by steam distillation and analysed by gas chromatography (GC) and gas chromatography coupled to mass spectrometry (GC-MS). Quantitative but not qualitative differences have been found between the analysed parts. The principal compounds from the inflorescences oil were found to be phyllocladene (37.6%) and bicyclogermacrene (15.1%), while the oil from stems and leaves showed phyllocladene (20.4%), gamma-muurolene (11.8%) and (E)-caryophyllene (10.1%) as main ones. The oil from the roots presented gamma-muurolene (15.4%) and phyllocladene (15.0%) as major constituents. It is worth mentioning the presence of a diterpene, phyllocladene, as main compound of the essential oil. This is the first report on the essential oil of this species.     

Essential oil composition of Nepeta satureioides from Iran

The essential oil of Nepeta satureioides Boiss. from Iran was isolated by hydrodistillation in yield of 0.06% (w/w). The chemical composition of the essential oil was analyzed by GC and GC-MS. Forty-five compounds accounting for 97.4% of the total oil were identified. The major components were linalool (23.8%), (Z,E)-farnesol (14.7%), linalyl acetate (11.1%), β-caryophyllene (6.6%), lavandulol acetate (6.6%), caryophyllene oxide (6.4%), and (Z)-β-farnesene (3.4%). Oxygenated terpenoids were the main group of compounds. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 144–145, March–April, 2006.     

Essential oil composition of Prasium majus from Croatia

The essential oils from the aerial parts of Prasium majus L., collected during two years in Croatia, were analysed by GC and GC/MS. Fifty-two compounds were identified, representing 90.3-91.8% of the total oils. The major constituents in both samples were fatty acids (particularly hexadecanoic acid and (Z)-octadec-9-enoic acid), lower aliphatic alcohols, aldehydes and acids (major ones oct-1-en-3-ol and (E,E)-hepta-2,4-dienal) and phenylpropane derivatives (e.g. eugenol). Beta-Caryophyllene was the most abundant terpene and (E)-beta-ionone was the major norisoprenoid.     

Essential oil composition of the different parts of Eryngium corniculatum Lam. (Apiaceae) from Spain

The essential oil from the different parts (inflorescences, stems+leaves and roots) of E. corniculatum Lam. gathered in Guadalajara (Spain) has been extracted by steam distillation and analysed by gas chromatography and gas chromatography coupled to mass spectrometry. Quantitative and qualitative differences have been found between the analysed parts, although all of them contained the same principal compound, 2,4,6-trimethylbenzaldehyde, representing the 50.8%, 50.0%, and 29.8% of the total oil for inflorescences, stems+leaves and roots, respectively. Other representative constituents of the oil were similar in the different fractions: in the inflorescences compounds were found to be alpha-pinene (4.0%), chrysanthenyl acetate (4.0%), 2,4,5-trimethylbenzaldehyde (3.3%), (2Z,6E)-farnesol (2.0%), (E)-nerolidol (2.1%) and (Z)-beta-ocimene (2.1%), while the stems+leaves oil showed 2,4,5-trimethylbenzaldehyde (3.8%), alpha-pinene (3.4%), (E)-nerolidol (2.4%) and (2Z,6E)-farnesol (2.1%), and in the roots oil a phyllocladene isomer (13.0%), (E)-nerolidol (9.4%), beta-eudesmol (4.1%) and (2Z,6E)-farnesol (2.1%) were found. The presence of C-10 compounds as the main fraction for an Eryngium species is worth mentioning. This is the first report on the chemical composition of this Mediterranean endemic species.     

Essential oil composition of Eucalyptus procera Dehnh. leaves from central Iran

The chemical composition of the essential oil of leaves of Eucalyptus procera Dehnh., cultivated in central Iran, was obtained by hydrodistillation and analysed by GC-MS. Forty-five constituents representing 99.6% of the total oil were identified. The main constituents of the oil were found to be 1,8-cineole (35.9%), α-pinene (25.6%) and viridiflorol (7.7%). Other representative compounds were identified as α-terpineol (3.6%), aromadendrene (3.5%) and trans-pinocarveol (3.0%).     

Analysis and evaluation of the antimicrobial and anticancer activities of the essential oil isolated from Foeniculum vulgare from Hamedan,Iran

In this study, biological properties of the essential oil isolated from seeds of Foeniculum vulgare (F. vulgare) were evaluated. GC-MS analysis revealed Trans-Anethole (80.63%), L-Fenchone (11.57%), Estragole (3.67%) and Limonene (2.68%) were the major compounds of the essential oil. Antibacterial activity of the essential oil against nine Gram-positive and Gram-negative strains was studied using disc diffusion and micro-well dilution assays. Essential oil exhibited the antibacterial activity against three Gram-negative strains of Pseudomonas aeruginosa, Escherichia coli, and Shigella dysenteriae. The preliminary study on toxicity of seed oil was performed using Brine Shrimp lethality test (BSLT). Results indicated the high toxicity effect of essential oil (LC50 = 10 μg/mL). In vitro anticancer activity of seed oil was investigated against human breast cancer (MDA-Mb) and cervical epithelioid carcinoma (Hela) cell lines by MTT assay. Results showed the seed oil behave as a very potent anticancer agent with IC50 of lower than 10 μg/mL in both cases.