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Chemical composition of the volatile oil from different plant parts of Anethum graveolens L. (Umbelliferae) cultivated in Romania



The essential oil from dried leaves, flowers and fruits of Anethum graveolens L. (dill) cultivated in Romania was isolated by hydrodistillation and analysed by gaschromatography coupled with mass spectrometry (GC-MS). The main components in leaves were α- phellandrene (62.71%), limonene (13.28%) and anethofuran (16.42%). The main components in flowers were α- phellandrene (30.26%), limonene (33.22%) and anethofuran (22%). Cis-carvone and limonene are the major constituents of seeds volatile oil with 75.2% and, respectively 21.56%.
FARMACIA, 2010, Vol.58, 5
University of Medicine and Pharmacy “Carol Davila”, Faculty of
Pharmacy, 6 Traian Vuia, 020956, Bucharest, Romania
*corresponding author:
The essential oil from dried leaves, flowers and fruits of Anethum graveolens L.
(dill) cultivated in Romania was isolated by hydrodistillation and analysed by gas-
chromatography coupled with mass spectrometry (GC-MS). The main components in
leaves were α- phellandrene (62.71%), limonene (13.28%) and anethofuran (16.42%). The
main components in flowers were α- phellandrene (30.26%), limonene (33.22%) and
anethofuran (22%). Cis-carvone and limonene are the major constituents of seeds volatile
oil with 75.2% and, respectively 21.56%.
Uleiul volatil obţinut din frunze, flori şi fructe uscate de Anethum graveolens L.
(mărar) cultivat în România, a fost izolat prin hidrodistilare şi analizat prin cromatografie
de gaze cuplată cu spectrometrie de masă (GC-MS). Principalii componenţi din frunze au
fost α-felandrenul (62,71%), limonenul (13,28%) şi anetofuranul (16,42%). Principalii
componenţi din flori au fost α-felandrenul (30,26%), limonenul (33,22%) şi anetofuranul
(22%). Cis-carvona şi limonenul sunt principalii compuşi din uleiul volatil obţinut din
seminţe, reprezentând 75,2% şi, respectiv, 21,56%.
Keywords: Anethum graveolens, dill, essential oil, carvone, limonene.
Anethum graveolens L. or dill, belonging to Apiaceae
(Umbelliferae) family, is an annual aromatic herb known for culinary and
medicinal use since ancient times. It is cultivated in the most parts of
Europe and the United States of America. A variant called east Indian dill or
sowa (Anethum sowa Roxb.) is cultivated in India, Egipt and Japan. The
chemical composition of the essential oil of the two chimiotypes of dill and
sowa differs mainly by the dillapiole content. The typical flavour of herb
dill oil is due to α-phellandrene, limonene and dill ether (anethofuran). For
flavouring purposes the herb oil with low content of carvone is preferred
[1]. The dill seed oil contains a small quantity of dillapiole up to 3% when
grown in tropical climate [1, 2]. In the east Indian dill (sowa) the content of
FARMACIA, 2010, Vol.58, 5
dillapiole ranges from 5 to 27% [3].
In recent years the scientific literature reports pharmacological
effects of dill such as antibacterial [4, 5], antimycobacterial [6], antioxidant
[7-10], cancer chemopreventive [11]. The well-known properties of dill
from the traditional medicine, such as carminative, stomachic, diuretic have
been reported [12, 13]. The dill essential oil has hypolipidemic activity and
could be a cardioprotective agent [14]. Many studies showed that dill
essential oil quantity and chemical composition varies depending on the
plant parts and the developing stage of the plant at harvest time [13, 15-17].
The scientific literature data concerning chemical composition of volatile oil
from different plant parts of Anethum graveolens L. are poor and differ from
one author to the other [3, 13-15, 18].
The aim of this paper is to elucidate the chemical composition of the
essential oil from leaves, flowers and fruits of dill cultivated in Romania. In
order to study the complex chemical composition of volatile compound
from plants, advanced analytical GC-MS techniques must be used, these
allowing the identification of compounds even in minute quantities [23, 24].
Materials and methods
Reagents and solvents
All solvents and reagents were purchased from Merck, Darmstadt,
Germany: dichloromethane, supraSolv for gas chromatography, anhydrous
Na2SO4 granulated for organic trace analysis, the C8-C20 and C21-C40 n-
alkanes used for the determination of Kovats retention indices.
Plant material
The raw material consisted of the leaves (harvested during the plant's
flowering), flowers (on the blossom stage), and fruits (at their full maturity)
of Anethum graveolens L., dill (Apiaceae) harvested in 2008 from Arges
county (the southern part of Romania; 500 m altitude). The products were
naturally dried in shadow and stored in controlled laboratory conditions.
Isolation of the essential oil
100 grams of fragmented dried vegetal products were hydrodistilled
with 500 mL water in a Clevenger-type apparatus without organic solvent
for 3h [25]. The essential oil was dried over anhydrous Na2SO4, stored in a
dark glass bottle and kept at 4°C until analysis.
FARMACIA, 2010, Vol.58, 5
Gas chromatography-mass spectrometry
GC-MS analyses was performed on a Fisons Instrument GC 8000
equipped with an electron impact quadrupole, MD 800 mass spectrometer
detector. The electron ionisation energy was 70 eV, ion-source temperature
200°C and the interface temperature 280°C.
A fused silica capillary column 5% phenyl-poly-dimethyl-siloxane
(DB-5MS 30 m x 0.32 mm i.d. and 0.25 µm film thickness, J&W Scientific)
was used. The column temperature was programmed as follows: from 40°C
(3 min hold) raised at 4°C/min to 250 °C and finally held at 250 °C for 10
min. A split-splitless injection (split ratio 1:30) at 280 °C was employed.
The carrier gas (helium) flow rate was 2 mL/min. Two µL of sample were
injected. Data acquisition was performed with MassLab software for the
mass range 30 - 600 u with a scan speed of 1 scan/s. The identification of
compounds was performed by comparing their mass spectra with data from
Adams [19], US National Institute of Standards and Technology (NIST,
USA), WILEY 1996 Ed. mass spectra library and a personal library of 600
spectra. The identification of compounds was also based on the Kovats
retention indices.
The Kovats retention indices were calculated using n-alkanes C8-C20
and C21-C40 and the experimental values were compared with those reported
in literature [20, 21].
Results and discussion
The average content in essential oil of Anethum graveolens samples
(3 determinations) was: 12 mL/kg for leaves, 32 mL/kg for flowers and 34
mL/kg for fruits (the results were calculated with reference to the dried
material). These values are comparable with the results mentioned in the
scientific literature about Anethum graveolens [3, 22].
In figure 1 are shown the chromatograms of essential oil from leaves
(a), flowers (b) and fruits (c).
FARMACIA, 2010, Vol.58, 5
c) fruits
a) leaves
b) flowers
Figure 1.
Chromatograms of leaves, flowers and fruits essential oil from Anethum
Table I shows the relative content of volatile compounds from
essential oil, expressed as percentage from total area.
FARMACIA, 2010, Vol.58, 5
Table I.
Chemical composition of essential oil from leaves,
flowers and fruits of Anethum graveolens L.
In the essential oil from Anethum graveolens L. leaves 21
compounds were identified, adding up to 97.55% of the total area.
Monoterpenic hydrocarbons were found predominant in the leaves oil
representing 79.14% of the total content, where α-phellandrene (62.71%)
constituted the major compound. This result is in agreement with that
reported by Amin and Sleem [13]. The oxygenated compounds reached up
to 16.56% with 16.42% dill ether (3,9-epoxy-1-p-menthen), which was the
major compound. The n-alkanes from C19-C27were found in small quantities
between 0.05 – 0.19% totalling 1.14%.
tR /min*
Dill Ether
Identified from total area
FARMACIA, 2010, Vol.58, 5
In the flower essential oil 13 compounds were identified adding up
to 99.83% of the total area. The main components of the volatile oil from
flowers are monoterpenic hydrocarbons: α-phellandrene (30.26%) and
limonene (33.22%), total monoterpenic hydrocarbons representing 65.21%.
In flowers essential oil the content of α-phellandrene is only 30.26%
compared with 62.71% in the leaves oil. On the other hand, the content of
limonene and dill ether in flowers oil is higher (33.22% and respectively
22.00%) than the one determined in leaves oil.
In the leaves oil, the ketonic compound carvone was not present but
in the flowers oil its content is 10.29%. In the essential oil of fruits, carvone
is the main compound with 75.21%.
Another ketonic compound absent in the leaves essential oil was
present in the flowers and fruits oils as cis- and trans-dihydrocarvone
isomers. The fruit essential oil was rich in limonene 21.56% and cis- and
trans-dihydrocarvone adding up to 3.06%. The amount of α-phellandrene in
leaves oil and flowers oil was 62.71%, respectively 30.26%, and only 0.12%
in fruits oil.
The chemical composition of dill volatile oil varies depending on the
plant parts. In the leaves oil monoterpenic hydrocarbons are predominant,
amounting to 79.14% (62.71% α-phellandrene and 13.28% limonene). In
the flowers oil the content of α-phellandrene and limonene is 32.26% and
33.22%, respectively. Anethofuran (dill ether) is present in leaves and
flowers with 16.42% and 22%, respectively, but is missing in the fruit oil.
The main compound in fruits essential oil is carvone (75.21%), while the
content of α-phellandrene is only 0.12% and limonene is 21.56%.
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Manuscript received: December 5th 2009
... According to this table, the principal components were dodecenyl acetate, N-octyl 2-methyl butyrate, octyl butyrate, Geraniol, Anethole, Geranyl acetate, n-Octyl acetate, trans-Anethole and octyl ester. The compounds in the present research have been found in other studies with different percentages, which is probably the reason for this difference, weather conditions, soil type, plant species and geographical region (Babri, Khokhar, Mahmood, & Mahmud, 2012;Jirovetz, Buchbauer, Stoyanova, Georgiev, & Damianova, 2003;Peerakam, Wattanathorn, Punjaisee, Buamongkol, Sirisa-ard, & Chansakaow, 2014;Radulescu, Popescu, & Ilies, 2010). ...
... Major components of dill herb are α-and β-phellandrenes, p-cymene, 3,9-oxy-p-menth-1-ene (dill ether), and 3,9-epoxy-p-menth-1-ene, and in fruits, depending on the variety, these are d-limonene, carvone, dihydrocarvone, dillapiol [30][31][32][33][34]. Although α-phellandrene is a very common cyclic monoterpene found in the EO of many types of medicinal and aromatic plants, the herb Anethum graveolens is one of the best sources, with a high content (50 to 70%) combined with easy extraction. ...
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... According to this table, the principal components were dodecenyl acetate, N-octyl 2-methyl butyrate, octyl butyrate, Geraniol, Anethole, Geranyl acetate, n-Octyl acetate, trans-Anethole and octyl ester. The compounds in the present research have been found in other studies with different percentages, which is probably the reason for this difference, weather conditions, soil type, plant species and geographical region (Babri, Khokhar, Mahmood, & Mahmud, 2012;Jirovetz, Buchbauer, Stoyanova, Georgiev, & Damianova, 2003;Peerakam, Wattanathorn, Punjaisee, Buamongkol, Sirisa-ard, & Chansakaow, 2014;Radulescu, Popescu, & Ilies, 2010). ...
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... They have been shown to stimulate bile salt secretion and digestive enzyme activities of intestinal mucosa and pancreas (Hernandez et al. 2004). Also, numerous studies showed that, the improvement of body weight and weight gain are due to active materials found in dill essential oil causing greater efficiency in utilization of feed, resulting in enhanced growth (Radulescu et al. 2010 andHippenstie et al. 2011). ...
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Adams, R. P. 2007. Identification of essential oil components by gas chromatography/ mass spectrometry, 4th Edition. Allured Publ., Carol Stream, IL Is out of print, but you can obtain a free pdf of it at
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The macrocyclic cyclodextrins (enzymic conversion products of starch) were dis- covered in 1891, and the structures were elucidated in the mid-1930s. Their industrial sig- nificance become obvious in the 1970s, and by now thousand of tons of the three cyclo- dextrins (α-, β-, and γCD) and of their chemical derivatives and inclusion complexes are produced industrially. The outer surface of these doughnut-shaped molecules is hydrophilic, but they possess an axial open cavity, which is of hydrophobic character and capable of including other apo- lar molecules (or their moiety) in case of geometric compatibility. This is the essence of mo- lecular encapsulation by inclusion complex formation.
The hydro-distilled and the infusion obtained from Tilia platyphyllos (Tiliaceae) flowers were extracted on 500mg octadecylsilane (C18) cartridges. The volatile compounds retained on C18 cartridge were eluted with dichloromethane. The hydro-distilled and infusion extracts were analyzed by gas chromatography coupled with mass spectrometry (GC/MS). In hydro-distilled and infusion extracts were identified 36 and 20 compounds, respectively. The main constituents of hydro-distilled were 2-phenylethanol with 26.07%, six monoterpenic hydrocarbons, eight monoterpenic alcohols, four phenol-ethers, eight carbonylic compounds, four esters and four alkanes. In the infusion extract, 2-phenylethanol represented 29.48% of the total area; other important compounds were: six monoterpenic hydrocarbons (totalling 12.23%) and six alkanes (22.17%). A few other major compounds were also identified: 2-phenylethyl butanoate (12.11%), 4-methyl-2.6-ditertbuthylphenol (5.01%), vomifoliol (4.44%).
The composition of the hydrodistilled volatile oil from the aerial parts (before flowering stage) of Anethum graveolens L. family Apiaceae was investigated by GC/MS. Twenty eight components representing 99.76% of the total chemical composition of the oil were identified. Monoterpene hydrocarbons were found predominating in the studied oil amounting (80.81%) where - phellandrene (63 %) constituted the major compound. Meanwhile, oxygenated compounds reached up to (8.26%) with dill-ether (6.20%) which was the major compound. The unsaponifiable matter and fatty acids methyl esters of the aerial parts were identified and estimated by GLC analysis. - Sitosterol (3.92%) was the major sterol, followed by campesterol (2.50%) and stigmasterol (2.01%) and n-dotriacontane (58.40%) represented the major hydrocarbon in the unsaponifiable fraction. Linoleic acid (20.51%) was the major fatty acid present followed by Nonadecanoic acid (9.95%). The aqueous infusion of the herb being the mode of administration in pharmaceutical formula in the market was studied. The n-hexane extract of the aqueous infusion showed spots similar to essential oil spots when compared by TLC. Also the ethyl acetate extract of the aqueous infusion showed spots of furanocoumarines which are characteristic to the family. The essential oil exhibited significant antibacterial activity against gram positive as well as gram negative bacteria and showed moderate antifungal effect. The petroleum ether extract showed broad spectrum antibacterial activity and antifungal effect but was being less active than essential oil. Meanwhile the aqueous extract had no antimicrobial and antifungal at the concentration used in the experiment (4 mg / disc). The essential oil showed high antimycobacterial effect at a minimum inhibitory concentration (MIC) ranging from 3 to 50 µl/ml. The LD50 for essential oil and aqueous extract was determined. The volatile oil as well as aqueous extract of the aerial parts exhibited a significant diuretic effect, anti-inflammatory effect and cytotoxic activity against three cell lines. The antispasmodic effect of aqueous infusion was also studied and showed to be significant. Egyptian Journal of Biomedical Sciences Vol. 23 (1) 2007: pp. 73-90
: The antioxidant, antifungal, and antibacterial potentials of essential oil and acetone extract of Anethum graveolens L. were investigated in the present study. The extract has shown excellent activity for the inhibition of primary and secondary oxidation products for rapeseed oil in comparision with butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT), which were evaluated using peroxide, thiobarbituric acid, p-anisidine, and carbonyl values. The activity of extract was further confirmed using other antioxidant properties such as ferric thiocyanate method inlinoleic acid system, which reducing power and scavenging effect (%) on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. Using inverted Petri plate method, the volatile oil completely inhibited the growth of Fusarium graminearum at 6 μL dose. Moreover, using poison food technique, the essential oil was found to be highly effective for controlling the growth of Penicillium citrinum and Aspergillus niger. In antibacterial investigations, using agar well diffusion method, the extract has shown better activity for Staphylococcus aureus and Bacillus cereus in comparison with commercial bactericide. However, essential oil has shown better activity for Pseudomonas aeruginosa. Gas chromatographic-mass spectroscopy studies on essential oil resulted in the identification of 35 components, which account for the 98.9% of the total amount. The major component was carvone (55.2%) followed bylimonene (16.6%), dillapiole (14.4%), andlinalool (3.7%). The analysis of acetone extract showed the presence of 25 components, which account for 94.5% of the total amount. The major components were dill apiole (43.2%), linoleic acid (23.1%), trans-anethole (11.0%), 2-propanone, 1-(4-methoxyphenyl) (4.6%), carvone (3.1%), p-anisaldehyde (2.7%), and myristicin (1.5%). In conclusion, the results presented here show that dill essential oil could be considered as a source for natural antimicrobial, whereas its extract could be considered as an alternative source of natural antioxidant.
The analysis of the δ13CPDB-values and the enantiomeric distribution in combination with the composition of the essential oil of dill (Anethum graveolens L.) at various developing stages of different plant parts allows us to draw valuable conclusions about the biosynthesis of the monoterpenes in the entire plant. The composition of the essential oil is different for the various plant parts and changes significantly during the ripening of the dill umbels. While α-phellandrene, β-phellandrene, dill ether and carvone occur enantiomerically pure in all investigated plant parts and during all stages of maturity, both enantiomers of limonene are detected. The enantiomeric composition of limonene is different for the various plant parts and changes during the development of the umbels. The δ13CPDB-values of the different monoterpenes also change with development. (R)-Limonene and carvone show absolutely the same behaviour in their δ13CPDB-values during the whole development of the umbels up to the seeds. In addition the δ13CPDB-values themselves are absolutely the same. Also α-phellandrene and dill ether show the same behaviour in their δ13CPDB-values, but the δ13CPDB-values themselves differ around 1.5–2‰. Based on the results of these investigations, a biochemical pathway of the monoterpenes in dill is postulated, according to which a very close biogenetic relationship is established for limonene and carvone and also for α-phellandrene and dill ether. © 1997 John Wiley & Sons, Ltd.
Abstract The composition of the steam distilled oil of the air-dried powdered fruits of A. graveolens L., grown in Egypt, was investigated by GC/MS. Seventeen components were identified of which limonene (30.3%), dillapiole (26.8%) and carvone (22%) were major and amounted to 79%. Piperitone (8.2%). the fourth major component, D8-dehydrop-cymene, camphor and linalylacetate are reported in the oil for the first time.
Meloxicam is a non steroidal anti inflammatory drug, used in the treatment of rheumatoid and osteoarthiritis. It is practically insoluble in water and its prolonged use is associated with the incidence of side effects like gastro intestinal perforations, ulcerations and bleeding. Therefore, an attempt has been made to improve the aqueous solubility of the drug by making an inclusion complex using hydroxy propyl β cyclodextrin(HPβ-CD). The complexes were prepared by physical mixture and freeze drying method. The different methods employed for evaluation such as DSC, XRD, SEM and FT-IR studies indicated complete formation of the complex by freeze drying method in a molar ratio of 1:2. The prepared complexes showed improved in-vitro dissolution profile as compared to the pure drug.