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Essential Oil Composition of Pulicaria dysenterica (L.)

Bernh from Iran
a a b c
Hasan Mumivand , Ali-Reza Rustaii , Kambiz Jahanbin & Dara Dastan
a
Department of Horticulture, Faculty of Horticulture and Plant Protection , University of
Tehran , Karaj , Iran , 31587–11167
b
Department of Food Science and Technology, Faculty of Biosystem Engineering , University
of Tehran , Karaj , Iran , 31587–11167
c
Medicinal Plants and Drug Research Institute , Shahid Beheshti University, Evin , Tehran ,
Iran Phone: 1983963113
Published online: 12 Mar 2013.

To cite this article: Hasan Mumivand , Ali-Reza Rustaii , Kambiz Jahanbin & Dara Dastan (2010) Essential Oil
Composition of Pulicaria dysenterica (L.) Bernh from Iran, Journal of Essential Oil Bearing Plants, 13:6, 717-720, DOI:
10.1080/0972060X.2010.10643884

To link to this article: http://dx.doi.org/10.1080/0972060X.2010.10643884

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 Jeobp 13 (6) 2010 pp 717 - 720 717

Journal of Essential Oil Bearing Plants

ISSN Print: 0972-060X ISSN Online: 0976-5026
www.jeobp.com

Essential Oil Composition of Pulicaria dysenterica (L.) Bernh from Iran

Hasan Mumivand 1, Ali-Reza Rustaii 1, Kambiz Jahanbin 2, Dara Dastan 3*

Downloaded by [University of Newcastle, Australia] at 12:44 08 January 2015

1
Department of Horticulture, Faculty of Horticulture and Plant
Protection, University of Tehran, Karaj, 31587-11167, Iran
2
Department of Food Science and Technology, Faculty of Biosystem
Engineering, University of Tehran, Karaj, 31587-11167, Iran
3
Medicinal Plants and Drug Research Institute, Shahid Beheshti
University, Evin, Tehran, 1983963113, Iran
Received 14 August 2009; accepted in revised form 04 April 2010

Abstract: The chemical composition of the essential oil from flowering aerial parts of
Pulicaria dysenterica (L.) Bernh (Asteraceae), growing wild in Iran, was determined by GC and
GC-MS. Nineteen compounds, representing about 96.0 % of the oil, were identified. Oxygenated
sesquiterpenes (43.5 %) and sesquiterpene hydrocarbons (41.5 %) were found to be the major
fraction of the oil. Also ar-curcumene (28.3 %), epi-α-cadinol (16.4 %) and (E)-coniferyl alcohol
(11.0 %) were the main components of the oil.

Key words: Pulicaria dysenterica, Asteraceae, essential oil, ar-curcumene, tau epi-
α-cadinol, (E)-coniferyl alcohol.

Introduction: The genus Pulicaria, belongs to the Astraceae family (tribe Inuleae),
comprises approximately 80 species which are widely distributed from Europe into North
Africa and Asia 1. Pulicaria dysenterica (L.) Bernh. is a perennial plant, up to 100 cm
height, with yellow flowers, growing on damp places and is founded in Europe, Anatolia,
Iraq, Iran, Turcomania, Afghanistan, Pakistan, Caucasus and North Africa 2. The plant
contains flavonoids, acetylenes, sesquiterpenelactons, isocomene and essential oil 3,4. It is
used to treat diarrhea and dysentery and has insecticidal property 4.
A chemical study on the essential oil of P. dysenterica from two different locations in
Greece revealed that β-caryophyllene, caryophyllene oxide, (Z)-nerolidol and (E)-nerolidiol
were the main components in oil samples 4. Since the chemical composition of the essential
oil depends on various parameters such as environmental conditions 5, this study was carried

*Corresponding author (Dara Dastan)

E- mail: < dara962@gmail.com > © 2011, Har Krishan Bhalla & Sons
 Dara Dastan et al. / Jeobp 13 (6) 2010 pp 717 - 720 718

out to investigate the constituents of the oil of P. dysenterica from Iran.

Experimental
Plant materials: The flowering aerial parts of P. dysenterica were collected in June
2008 from Malayer, Hamedan province, west of Iran. Voucher specimen (24474 [FUMH])
was deposited in the Ferdowsi University of Mashhad Herbarium (FUMH), Mashhad, Iran.

Essential oil isolation: Plant materials were air-dried in the shade, then subjected to
hydrodistillation for 4 h using a Clevenger-type apparatus. The obtained oil which had
yellowish color with a strong odor, was dried over anhydrous sodium sulfate and stored at
Downloaded by [University of Newcastle, Australia] at 12:44 08 January 2015

4°C prior to analysis.

GC analysis: GC analysis was performed by using a Thermoquest gas chromatograph

with a flame ionization detector (FID). The analysis was carried out using a fused silica
capillary DB-5 column (30 m × 0.25 mm i.d.; film thickness 0.25 μm). The operating
conditions were as follows: injector and detector temperatures were 250°C and 280°C,
respectively; nitrogen was used as the carrier gas at a flow rate of 1 ml/min; oven temperature
was programmed from 60°C-250°C at the rate of 4 °C/min; and finally held isothermally for
10 min. The split ratio was 1/50.

GC-MS analysis: GC-MS analysis was performed by using a Thermoquest-Finnigan

gas chromatograph equipped with above mentioned column and coupled to a TRACE mass
quadrapole analyzer. The analysis was carried out using a fused silica capillary DB-5 column
(60 m × 0.25 mm i.d.; film thickness 0.25 μm). Temperature programming conditions were
as given for GC. Helium was used as the carrier gas with ionization voltage of 70 eV. Ion
source and interface temperatures were 200°C and 250°C, respectively. Mass range was
from m/z 43-456.
The constituents of the oil were identified by calculation of their retention indices
under temperature programmed conditions for n-alkanes (C6-C24) and the oil on a DB-5
column under the same chromatographic conditions. Identification of individual compounds
was made by comparison of their mass spectra and retention indices with those authentic
samples and those given in the literature 6. Quantification of the relative amount of the
individual components was performed according to the area percentage method without
consideration of calibration factor.

Results and discussion: The oil yield from the aerial parts of P. dysenterica was 0.4
%, based on the dry weight. The constituents identified in the oil and their relative percentages
are presented in table 1. A total of 19 compounds were characterized, comprising about 96.0
% of the essential oil. Oxygenated sesquiterpenes (43.5 %) constituted the principle fraction
of the oil with epi-α-cadinol (16.4 %), neryl isovalerate (5.5 %), α-cadinol (4.5 %) germacrene
D-4-ol (4.5 %) and 10-epi-italicene ether (4.1 %) as the major components., Sesquiterpene
hydrocarbons accounted to 41.5 % of the oil by ar-curcumene (28.3 %), α-cadinene (4.9%)
and (trans)-caryophylene (2.5 %) as the main constituents. Finally, phenolic compounds
 Dara Dastan et al. / Jeobp 13 (6) 2010 pp 717 - 720 719

with (E)-conyferyl alcohol made up 11.0 % of the total oil.

Comparing results of this study with those from the Greece showed that the composition
of oils has significant differences for relative percentage of constituents and for the main
components 4. Morevere, none of the essential oil constituents reported in the literature for
other Pulicaria species were dominated by ar-curcumene, epi-α-cadinol and E-conyferyl
alcohol 7,8.

References
1. Williams, C.A., Harborne, J.B., Greenham, J.R., Grayer, R.J., Kite, G.C. and
Eagles J. (2003). Variations in lipophilic and vacuolar flavonoids among European
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Pulicaria species. Phytochemistry. 64: 275-283.

2. Lack, H.W. (1980). Pulicaria. In: Rechinger K.H. (ed.), Flora Iranica, Inuleae, Vol.
145, pp. 116-117. Academische Druck and Verlagsanstalt, Graz.
3. Marco, J.A., Sanz, J.F. and Albiach, R. (1992). Caryophyllene derivatives from
Pulicaria dysenterica. Phytochemistry. 31: 2409-2413.
4. Basta, A., Tzakou, O., Couladis, M. and Pavlovic, M. (2007). Chemical Composition
of Pulicaria dysenterica (L.) Bernh. from Greece. Essential Oil Research. 19: 333-
335.
5. Morteza-Semnani, K., Akbarzadeh, M. and Rostami, B. )2005). The essential oil
composition of Teucrium chamaedrys L. from Iran. Flavour Fragr. 20: 544-546
6. Adams, R.P. (2001). Identification of Essential Oil Components by Gas Chromato-
graphy/Quadrupole Mass Spectroscopy. Allured Publishing Corporation, Carol Stream,
IL.
7. Weyerstahl, P., Marschall, H., Wahlburg, H.C., Christiansen, C., Rustaiyan, A.
and Mirdjalili, F. (1999). Constituents of the essential oil of Pulicaria gnaphalodes
(Vent.) Boiss. from Iran. Flavour Fragr. 14: 121-130.
8. Hanbali, F.E.L., Akssira, M., Ezoubeiri, A., Gadhi C.A., Mellouki, F., Benherraf,
A., Blazquez, A.M. and Boira, H. (2005). Chemical composition and antibacterial
activity of essential oil of Pulicaria odora L. Ethnopharmacology. 99: 399-401.
 Dara Dastan et al. / Jeobp 13 (6) 2010 pp 717 - 720 720

Table 1. Chemical composition of the essential oil of Pulicaria dysenterica

No Compound RI %

1 Silphiperfol-6-ene 1379 1.9

2 Italicene 1406 1.1
3 trans-Caryophyllene 1419 2.5
4 β-Gurjunene 1434 1.3
5 ar-Curcumene 1481 28.3
6 α-Muurolene 1500 0.7
γ-Cadinene
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7 1514 0.8
8 Italicene ether-(10-epi) 1516 4.1
9 α-Cadinene 1539 4.9
10 Ledol 1569 0.4
11 Germacrene D-4-ol 1576 4.5
12 Caryophyllene oxide 1583 2.6
13 Neryl isovalerate 1584 5.5
14 Helifolen-(2-a) 1620 1.8
15 (trans)-isolongifolanone 1627 1.2
16 Cadinol-(epi-α) 1640 16.4
17 α-Cadinol 1654 4.5
18 α-Bisabolol 1686 2.5
19 (E)-Coniferyl alcohol 1735 11

Oxygenated sesquiterpenes 43.5

Sesquiterpene hydrocarbons 41.5
Phenolic compounds 11.0
Total 96.0

RI : retention indices relative to C6-C24 n-alkanes on the DB-5 column