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.     

Volatile fraction of lavender and bitter fennel infusion extracts

The relative proportions of chemical classes (hydrocarbons, oxides, alcohols/ethers, aldehydes/ketones, acids/esters/lactones) in the essential oil of lavender (Lavendula angustifolia Mill., family Lamiaceae) and bitter fennel (Foeniculum vulgare Mill. subsp. vulgare var. vulgare (Mill.) Thellung, family Apiaceae) and in the volatile fraction of infusion extracts were examined and showed remarkable differences. The volatile compounds of infusions were isolated by hydrodistillation and solid phase extraction (SPE). Their qualitative and semiquantitative compositions were compared with the essential oil isolated by hydrodistillation directly from the plant material and analyzed by GC-MS. Furthermore, quantification of the major constituents of lavender oil and of the volatile fraction obtained by hydrodistillation of the infusion was performed. Comparison of the total essential oil yield quantified by hydrodistillation of the lavender infusion (0.7% v/w, corresponding to plant material) with the essential oil yield of the blossoms (5.1% v/w) revealed that only 13.9% of the initial oil could be extracted by infusion. The main constituents of the volatile fraction of the lavender infusion were (hydrodistillation/SPE): linalool (39.3%/28.2%), 1,8 cineole (24.8%/18.9%), cis-linalool oxide (furanoid) (5.8%/8.0%), trans-linalool oxide (furanoid) (4.1%/7.1%), camphor (5.3%/4.0%) and alpha-terpineol (4.0%/3.0%). The major constituents of lavender essential oil were linalool (28.8%), 1,8-cineole (18.05%), linalyl acetate (13.9%) and alpha-terpineol (4.0%). Most intriguing, in the volatile fraction of lavender infusion a significant proportional decrease of linalyl acetate and an increase of linalool oxides was recognized. The essential oil yield of fennel fruits was 12.5% v/w, whereas 1.8% v/w volatile fraction (corresponding to plant material) was obtained by hydrodistillation of the fennel infusion, which is equivalent to 14.5% of the initial fennel essential oil. The main constituents of the volatile fraction of the fennel infusion were (hydrodistillation/SPE): trans-anethole (56.4%/54.8%), fenchone (36.2%/39.5%) and estragole (2.5%/2.2%), which were also the major compounds of the genuine bitter fennel essential oil. In infusions, the proportion of ethers vs. ketones was shifted significantly towards a higher proportion of the latter compared with the essential oil obtained from the fruits.     

Composition of the essential oils from Anthriscus cerefolium var. trichocarpa and A. caucalis growing wild in the urban area of Vienna (Austria)

The composition of the essential oil from the different above ground plant parts of Anthriscus cerefolium and A. caucalis collected in the urban area of Vienna has been studied. The essential oils of A. cerefolium were dominated by estragole (= methylchavicol) and 1-allyl-2,4-dimethoxybenzene, occurring in various proportions. The oils from young flowering plants had more estragole than 1-allyl-2,4-dimethoxybenzene. Fruits from one location reached 95% estragole in the essential oil. In A. caucalis, the main compound of all oils was cis-chrysanthenyl acetate (up to 74%) followed by cis-chrysanthenol (up to 16%). The fruit oils displayed a higher proportion of cis-chrysanthenyl acetate than the leaf or stem oils.     

Chemical composition, antimicrobial and antioxidant activities of essential oils from organically cultivated fennel cultivars

Essential oils of the fruits of three organically grown cultivars of Egyptian fennel (Foeniculum vulgare var. azoricum, Foeniculum vulgare var. dulce and Foeniculum vulgare var. vulgare) were examined for their chemical constituents, antimicrobial and antioxidant activities. Gas chromatography/mass spectrometry analysis of the essential oils revealed the presence of 18 major monoterpenoids in all three cultivars but their percentage in each oil were greatly different. trans-Anethole, estragole, fenchone and limonene were highly abundant in all of the examined oils. Antioxidant activities of the essential oils were evaluated using the DPPH radical scavenging, lipid peroxidation and metal chelating assays. Essential oils from the azoricum and dulce cultivars were more effective antioxidants than that from the vulgare cultivar. Antimicrobial activities of each oil were measured against two species of fungi, two species of Gram negative and two species of Gram positive bacteria. All three cultivars showed similar antimicrobial activity.     

Development and validation of a high-performance liquid chromatographic method for the analysis of antioxidative phenolic compounds in fennel using a narrow bore reversed phase C18 column

A simple high-performance liquid chromatography (HPLC) method for the separation and quantitative determination of the main antioxidant phenolic compounds from bitter fennel, Foeniculum vulgare, was developed. The use of a narrow bore reversed phase (RP) C₁₈ column and an acidic mobile phase enabled ten compounds (caffeoylquinic acids, dicaffeoylquinic acids, flavonoids and rosmarinic acid) to be separated within a 40 min time analysis. The method was validated to demonstrate its selectivity, linearity, precision, accuracy and robustness. In addition, some parameters were studied to optimize the complete extraction of the phenolic compounds. The method was applied to the evaluation of three different fennel materials: distilled and non-distilled aerial parts, as well as defatted fruits. Distilled fennel was found to contain a higher proportion of antioxidant phenolic compounds than the non-distilled plan material.     

碱催化法衍生化气相色谱/质谱法分析青海湖裸鲤鱼油中的脂肪酸

用碱催化法将青海湖裸鲤鱼油甲酯化,以气相色谱/质谱法分析鱼油中的脂肪酸。青海湖裸鲤可食用部分中鱼油含量为25.13%。从鱼油中共鉴定出47种脂肪酸,包括直链、单支链、多支链饱和脂肪酸,单不饱和、多不饱和脂肪酸,环丙烷基、呋喃基脂肪酸等。不饱和脂肪酸含量为73.6%,其中多不饱和脂肪酸含量为25.4%,以C18∶2(4.9%),C18∶3(3.1%),C20∶4(1.3%),C20∶5(二十碳五烯酸（EPA）, 9.4%)和C22∶6(二十二碳六烯酸（DHA）, 6.7%)为主。单不饱和脂肪酸含量为48.2%,主要由C16∶1(20.3%),C18∶1(25.9%)构成。饱和脂肪酸含量为25.7%,主要有C14∶0(3.4%),C16∶0 (19.4%)和C18∶0(1.1%)。青海湖裸鲤鱼油中还存在不常见的环丙烷基和呋喃基脂肪酸及多种奇数碳链和支链脂肪酸。因此,青海湖裸鲤是功能性脂肪酸的重要膳食来源。     

Evaluation of essential oils for maintaining postharvest quality of Thompson seedless table grape

The effects of postharvest spraying of essential oils from sweet basil (Ocimum basilicum), fennel (Foeniculum vulgare), summer savory (Satureja hortensis) and thyme (Thymus vulgaris) on fungal decay and quality parameters of the 'Thompson seedless' table grape stored at 0?±?1°C for 60 days were evaluated. Results showed that the essential oils, especially of thyme and fennel, have a good inhibitory effect on the development of fungal decay in Thompson table grapes. In addition, essential oils reduced weight loss, berry and rachis browning and had no considerable adverse effect on the flavour of the fruits. GC-MS analysis showed that the main compounds identified in sweet basil, fennel, summer savory and thyme oils are linalool (65.25%), trans-anethole (64.72%), carvacrol (54.14%) and β-ocimene (12.62%), respectively. Therefore, these essential oils have good potential for use as an alternative to synthetic fungicides for the preservation and storage of table grapes.     

杏仁油的物化性能及其脂肪酸组成的分析

用３种不同溶剂萃取杏仁得到杏仁油,并对其物化常数进行测定。杏仁油用饱和氢氧化钾 甲醇皂化,再用甲醇 硫酸（体积比为４∶１）甲酯化后,将乙醚萃取液作气相色谱分析。太原杏仁油中脂肪酸的主要成分为油酸（Ｃ１８∶１,质量分数约６８％）和亚油酸（Ｃ１８∶２,质量分数约２５％）,少量棕榈酸（Ｃ１６∶０）、棕榈烯酸（Ｃ１６∶１）和硬脂酸（Ｃ１８∶０）,微量花生酸（Ｃ２０∶０）。     

Characterization of essential oil recovered from fennel horticultural wastes

Fennel crop has been traditionally used as spice in cooking and fragrances, and in folk medicine for its spectrum of useful properties. Mediterranean is the elective natural cultivation area for this plant with Italy being a leader producer. A limit of this production is due to the high amount of wastes derived still rich of phytochemicals, which are usually underused. Hence, the extraction and characterization of essential oil from residues of fennel horticultural market was investigated to understand the potential profit of their recycling. Forty-eight compounds resulted for fennel oil waste, analysed by GC-FID-MS, with the most abundant among components was anethole. Other constituents contributing to fennel flavour were the monoterpenes limonene and nerol. The exploitation of this oil as a good source of bioactive compounds was assessed by means of its antioxidant power measured with DPPH test.     

Contribution to the analysis of the essential oil of Helichrysum italicum (Roth) G. Don. Determination of ester bonded acids and phenols

The essential oil of Helichrysum italicum (Roth) G. Don (everlasting or Immortelle essential oil) was isolated by hydrodistillation and analysed by GC and GCMS. Forty four compounds were identified. The main components were alpha-pinene(12.8%), 2-methyl-cyclohexyl pentanoate (11.1 %), neryl acetate (10.4%), 1,7-di-epi-alpha-cedrene (6.8%) and other compounds. The oil was fractionated and ester-containing fraction was hydrolysed with KOH/H(2)SO(4). The liberated volatiles were analysed by GC and GC-MS: three phenols and twenty seven volatile carboxylic acids were identified[70% low fatty acids (C(2)-C(5)), 15% C(10)-C(12) acids and 15% other acids]. The main acids were acetic acid (24.3%) propanoic acid (17.2%), 2-methylpropanoic acid (11.4%),dodecanoic acid (8.7%), 2-methylbutanoic acid (8.3%), (Z)-2-methylbutenoic acid(5.1%) and decanoic acid (4.6%). With respect to the identified bonded carboxylic acids,the minimal number of esters in the oil was twenty seven, but their overall quantity was probably larger due to different possible combinations of alcohols with acids to form esters. On the other hand, only six main esters were identified in the oil before fractionation and hydrolysis.     

Investigation of the composition and stability of the essential oils of origanum vulgare ssp.vulgare L. andO. vulgare ssp.hirtum (Link) letswaart

Summary The essential oils ofOriganum vulgare L. ssp.hirtum (Link) letswaart andOriganum vulgare L ssp.vulgare (Fam. Lamiaceae), cultivated in Hungary, have been studied by GC and GC-MS and the qualitative and quantitative chemical composition of the essential oils in the two species have been compared.O. vulgare ssp.hirtum oil was found to contain carvacrol (76.4%), γ-terpinene (6.6%), thymol (0.23%), andp-cymene (4.7%) as the main constituents whereas the major compounds inO. vulgare ssp.vulgare oil werep-cymene (22.3%), caryophyllene oxide (10.2%), sabinene (7.9%), γ-terpinene (5.1%), thymol (0.34%), and spathulenol (4.8%). The stability of content and composition of the oils during the flowering period (economically beneficial period) were observed. The effect of long-term storage on the composition of the oil was also investigated for both the crude and distilled oil ofOriganum vulgare ssp.vulgare. Presented at Balaton Symposium '01 on High-Performance Separation Methods, Siófok, Hungary, September 2–4, 2001     

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.     

Oil composition and some morphological characters of Crambe orientalis var. orientalis and Crambe tataria var. tataria from Turkey

Native Crambe orientalis var. orientalis and Crambe tataria var. tataria collected from Kahramanmaras flora were morphologically examined and seed oil composition was determined. Volatile acid and fatty acid composition of seeds were examined with GC and GC/MS and the ratio of volatile acids to total oil was 3.49% in C. orientalis and 17.49% in C. tataria. The ratio of fatty acids to total oil was 92.03 and 67.28% in C. orientalis, and C. Tataria, respectively. The amount of erucic acid was 39.29% in C. orientalis and 29.87% in C. tataria. High linolenic acid (21.21%) and linoleic acid (12.42%) was found in C. orientalis oil, and high linolenic acid (15.01%) and linoleic acid (9.00%) was also found in C. tataria oil.     

<em>In Vitro</em> Anti-diabetic Activities and Chemical Analysis of Polypeptide-k and Oil Isolated from Seeds of <em>Momordica charantia</em> (Bitter Gourd)

The amino acid and fatty acid composition of polypeptide k and oil isolated from the seeds of Momordica charantia was analysed. The analysis revealed polypeptide k contained 9 out of 11 essential amino acids, among a total of 18 types of amino acids. Glutamic acid, aspartic acid, arginine and glycine were the most abundant (17.08%, 9.71%, 9.50% and 8.90% of total amino acids, respectively). Fatty acid analysis showed unusually high amounts of C18-0 (stearic acid, 62.31% of total fatty acid). C18-1 (oleic acid) and C18-2 (linoleic acid) were the other major fatty acid detected (12.53% and 10.40%, respectively). The oil was devoid of the short fatty acids (C4-0 to C8-0). Polypeptide k and oil were also subjected to in vitro α-glucosidase and α-amylase inhibition assays. Both polypeptide k and seed oil showed potent inhibition of α-glucosidase enzyme (79.18% and 53.55% inhibition, respectively). α-Amylase was inhibited by 35.58% and 38.02%, respectively. Collectively, the in vitro assay strongly suggests that both polypeptide k and seed oil from Momordica charantia are potent potential hypoglycemic agents.     

Method development for the analysis of trans-fatty acids in hydrogenated oils by capillary electrophoresis

A novel capillary electrophoresis methodology using UV indirect detection (224 nm) for the analysis of trans-fatty acids in hydrogenated oils was proposed. The electrolyte consisted of a pH 7 phosphate buffer at 15 mmol x L(-1) concentration containing 4 mmol.L(-1) sodium dodecylbenzenesulfonate, 10 mmol x L(-1) polyoxyethylene 23 lauryl ether (Brij 35), 2% 1-octanol and 45% acetonitrile. Under the optimized conditions, ten fatty acids, C12:0, C13:0 (internal standard), C14:0, C16:0, C18:0, C18:1c, C18:1t, C18:2cc, C18:2tt and C18:3ccc were baseline-separated in less than 12 min. The proposed methodology was applied to monitor the formation of trans-fatty acids during hydrogenation of Brazilnut oil. A crude oil sample (42.1% linoleic acid, 37.3% oleic acid, 13.4% palmitic acid, and 7.0% stearic acid) was mixed with 0.25% of a nickel-based catalyst and submitted to two independent hydrogenation conditions: 175 degrees C, 3 atm, 545 rpm for 60 min (GH(1) sample), and 150 degrees C, 1 atm, 545 rpm for 30 min (GH(2) sample). For the most severe hydrogenation condition (higher temperature and pressure, under longer reactional period), a more complete conversion of linoleic and oleic acids into stearic acid occurred with concomitant formation of the trans-species, elaidic acid (C18:1t). For the milder hydrogenation procedure that generated sample GH(2), larger amounts of linoleic and oleic acids remained, in addition to the transformations already observed in the GH(1) sample.     

Selective measurement of chromium(VI) by fluorescence quenching of ruthenium

The oxidative deterioration of polyunsaturated fatty acids (PUFAs) in culinary oils and fats during episodes of heating associated with normal usage (80-300 degrees C, 20-40 min) has been monitored by Fourier transform infrared spectroscopy (FTIR). The thermal oxidation of PUFAs is a free radical chain reaction, in which hydroperoxides are generally recognized as the primary major products. Hydroperoxides of PUFAs are easily decomposed into a very complex mixture of secondary products with the decrease in unsaturation. The oxidative advance of PUFAs during heating was studied by the determination of unsaturation percentage at different temperatures and heating times. Oils frequently used in food frying such as olive oil, sunflower oil, corn oil and seeds oil (sunflower, safflower and canola seed) were studied. The results show there is a decrease in unsaturation starting at 150 degrees C and becoming more pronounced at temperatures around 250 degrees C. The following variations were found in the unsaturation percentage, expressed as methyl linoleate, between the original sample and the sample heated at 300 degrees C for 40 min: olive oil (19-6%), sunflower oil (29-12%), corn oil (28-18%) and seeds oil (23-11%). This variation in unsaturation grade provides evidence of the transformation of essential PUFAs and subsequent decrease in the oils' nutritional value. The internal standard method is suitably precise when the n-valeronitrile is used as standard as shown by the 1-2% relative standard deviation (R.S.D.) found for seven replicates.     

Extraction and separation of volatile and fixed oils from berries of Laurus nobilis L. by Supercritical CO2

Isolation of volatile and fixed oils from dried berries of Laurus nobilis L. from Tunisia have been obtained by supercritical fractioned extraction with carbon dioxide. Extraction experiments were carried out at a temperature of 40 degrees C and pressures of 90 and 250 bar. The extraction step performed at 90 bar produced a volatile fraction mainly composed of (E)-beta-ocimene (20.9%), 1,8-cineole (8.8%), alpha-pinene (8.0%), beta-longipinene (7.1%), linalool acetate (4.5%), cadinene (4.7%), beta-pinene (4.2%), alpha-terpinyl acetate (3.8%) and alpha-bulnesene (3.5%). The oil yield in this step of the process was 0.9 % by weight charged. The last extraction step at 250 bar produced an odorless liquid fraction, in which a very small percentage of fragrance compounds was found, whereas triacylglycerols were dominant. The yield of this step was 15.0 % by weight. The most represented fatty acids of the whole berry fixed oil were 12:0 (27.6%), 18:1 n-9 (27.1%), 18:2 n-6 (21.4%), and 16:0 (17,1%), with the 18:1 n-9 and 18:2 n-6 unsaturated fatty acids in particular averaging 329 microg/mg of oil.     

Ultrasound-assisted temperature-controlled ionic-liquid dispersive liquid-phase microextraction method for simultaneous determination of anethole,estragole, and para-anisaldehyde in different plant extracts and human urine: a comparative study

In this study, the performances of four ionic-liquid-based microextraction methods, ionic-liquid-based dispersive liquid–liquid microextraction (IL-DLLME), ionic-liquid-based ultrasound-assisted emulsification microextraction (IL-USA-ME), temperature-controlled ionic-liquid dispersive liquid-phase microextraction (TC-IL-DLME), and ultrasound-assisted temperature-controlled ionic-liquid dispersive liquid-phase microextraction (USA-TC-IL-DLME), were investigated for extraction of three bioactive compounds (anethole, estragole, and anisaldehyde) from different plant extracts and human urine. Anethole and estragole were chosen because they can alter cellular processes positively or negatively, and an efficient method is needed for their extraction and sensitive determination in the samples mentioned. Because there is no previous report on the separation of anethole and estragole (structural isomers), first, simultaneous gradient elution and flow programming were used. The microextraction methods were then applied and compared for analysis of these compounds in plant extracts and human urine by use of high-performance liquid chromatography (HPLC). The effect of conditions on extraction efficiency was studied and under the optimum conditions, the best enrichment factors (58–64), limits of detection (14–18 ng mL^?1), limits of quantification (47–60 ng mL^?1), and recovery (94.4–101.7 %) were obtained by use of USA-TC-IL-DLME. The optimized conditions were used to determine anethole, estragole, and para-anisaldehyde in fennel, anise, and tarragon extracts and in human urine.     

Determination of Estragole in Fennel Herbal Teas by HS-SPME and GC–MS

Estragole, a volatile phenylpropanoid contained in a variety of edible herbs, has been demonstrated to be genotoxic and carcinogenic, and its addition as a flavoring substance to foodstuffs has been banned by the regulatory bodies of the European Union. Fast and accurate analytical methods for its determination in herbs are thus necessary to assess the dietary exposure of this substance in humans and, in particular, to sensitive groups. In the present study, headspace solid-phase microextraction (HS-SPME) combined with gas chromatography–mass spectrometry (GC–MS) was applied for determination of estragole in infusions from different widely used commercial herbal teas based on Foeniculum vulgare (fennel) seeds. The optimized HS-SPME extraction conditions involved the use of a polydimethylsiloxane fiber exposed to the herbal infusion for 20 min at 50°C followed by GC–MS analysis. The method was fully validated for linearity, sensitivity, accuracy, and precision and applied to real samples; the level of estragole in infusions of commercial fennel seed teas was found to be within 50–250 µ`^?1.     

Chemical composition, antioxidant properties and anti-cholinesterase activity of Cordia gilletii (Boraginaceae) leaves essential oil

This study aimed to investigate for the first time the chemical composition, the antioxidant properties and the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity of the essential oil from the leaves of Cordia gilletii De Wild (Boraginaceae). The essential oil, characterized by 23 constituents (90.1% of the total oil), was constituted by terpene derivatives (25.6%) and non-terpene derivatives (64.5%), among which aldehydes, fatty acids and alkanes were present with the percentage of 16.5%, 18.8% and 23.1%, respectively. The antioxidant activity of C. gilletii essential oil was screened by two in vitro tests: DPPH and beta-carotene bleaching test. The essential oil revealed antioxidant activity with an IC50 value of 75.0 and 129.9 microg/mL on DPPH radical and beta-carotene decoloration tests, respectively. Moreover, C. gilletii inhibited AChE enzyme with an IC50 value of 105.6 microg/mL.