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Comparison of Essential Oil Constituents of Scirpus Littoralis Schrad and Scirpus Wardianus J. R. Drumm. from Iran

DOI:10.1155/2011/580409
Authors:
Alireza Feizbakhsh at Islamic Azad University
Alireza Feizbakhsh
A. Naeemy at Tehran University of Medical Sciences
A. Naeemy
A. Aghassi
A. Aghassi
A. Aghassi
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Abstract

The essential oils obtained by hydrodistillation of aerial part of S. littoralis and S. wardianus grown in Iran were analyzed by GC/MS. Twenty seven components of S. littoralis and S. wardianus representing 85.5% and 86% of the oils were identified respectively. The major components in both oils were cyperene and cyperotundone, representing 18.7% and 14.8% in S. litoralis and 24.1% and 11.1%, in S. wardianus. Both oils were richer in sesquiterpene hydrocarbon and oxygenated sesquiterpene.
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ISSN: 0973-4945; CODEN ECJHAO
E-Journal of Chemistry
http://www.e-journals.net 2011, 8(S1), S289-S292
Comparison of Essential Oil Constituents of
Scirpus Littoralis Schrad. and
Scirpus Wardianus J. R. Drumm. from Iran
A. FEIZBAKHSH*, A. NAEEMY and A. AGHASSI
*Department of Chemistry, Islamic Azad University
Central Tehran Branch (IAUCTB), P.O.Box 14676-86831, Tehran, Iran
Department of Chemistry, K.N. Toosi University of Technology
P.O. Box 15875-4416, Tehran, Iran
a.feizbakhsh@yahoo.com
Received 26 August 2010; Accepted 25 October 2010
Abstract: The essential oils obtained by hydrodistillation of aerial part of
S. littoralis and S. wardianus grown in Iran were analyzed by GC/MS. Twenty
seven components of S. littoralis and S. wardianus representing 85.5% and 86%
of the oils were identified respectively. The major components in both oils were
cyperene and cyperotundone, representing 18.7% and 14.8% in S. litoralis and
24.1% and 11.1%, in S. wardianus. Both oils were richer in sesquiterpene
hydrocarbon and oxygenated sesquiterpene.
Keywords: Scirpus littoralis, Scirpus wardianus, Essential oil composition, Cyperene,
Cyperotundone
Introduction
The plant genus scirpus consists of a large number of aquatic, grass-like species in the
family cyperceae and grows in wetlands and moist soil. Scirpus species are often
planted to inhibit soil erosion and provide habitat for other wildlife1. They have been
extensively used in constructed wetlands for wastewater treatment because they can
efficiently remove nutrients and pathogens from effluent2-7. Also, some species of
Scirpus may have a relatively low ability to take up heavy metals, for example,
S. robustus that efficiently removes selenium (Se) from contaminated water
demonstrating potential for Se phytoremediation by wetlands8,9. On the other hand, it
has been reported that the rhizomes of S. yagara Ohwi, as a commonly used
traditional Chinese medicine (TCM), have the therapeutic functions of promoting
S290 A. FEIZBAKHSH et al.
blood circulation, removing stagnation, relieving pain, etc. It has been used solely or
as an important ingredient in some traditional prescriptions for the treatment of
hyperemesis gravidarum, postpartum abdominal pain, dyspepsia and amenorrhea10.
Two species of this genus, which grow wild in the east and southern east of Iran, are
Scirpus littoralis Schrad. and Scirpus wardianus J. R. Drummond11,12. To date, no
information on the chemical composition of the essential oil of S. littoralis and
S. wardianus of Iran origin is available. So we decided to examine this oil.
Experimental
The aerial parts of the S. littoralis species were collected between Zabol and Takht
adalat around Hamun Lake in Province of Sistan va Balutchestan, Iran, in April 2007
at the flowering stage and S. wardianus from around Hirmand River, Province of
Sistan va Balutchestan, Iran, in June 2007. Voucher specimens have been deposited at
the herbarium of Research Institute of Forests and Rangelands (TARI).
Hydrodistillation
The aerial parts of the plant after grinding had been submitted to hydrodistillation
with a Clevenger type apparatus according to the standard procedure described in the
European Pharmacopoeia13. The essential oil had been co-distilled with water for 3 h,
collected, dried under anhydrous sodium sulfate and stored at 4 ºC until used. The
yield of the oil was 1.5% and 1.2% (v/w), based on dry plant weight.
Gas chromatography-mass spectrometry
The essential oils were analyzed by gas chromatography coupled to mass spectrometry
(GC–MS) (Hewlett- Packard computerized system comprising a 6890 gas
chromatograph coupled to a 5973 mass spectrometer) using a capillary column, Hp-5Ms
(5% phenylmethyl siloxane) (30 m × 0.25 mm, film thickness 0.25 µm). Oven
temperature was programmed 60 ºC for 20 min, and then increased to 220 ºC at a rate of
4 ºC/min, finally holding at 220 ºC for 20 min. Helium was used as carrier gas at a flow
rate of 1 ml/min. The ionization energy was 70 eV with a scan time of 1 s and mass
range of 40–300 amu. Retention indices for all the compounds were determined
according to the Kovats method using n-alkanes as standards. The identification of the
oil components was accomplished by comparison of their GC retention indices as well
as their mass spectra with corresponding data of authentic compounds or of components
of reference oils14,15. Relative percentage was calculated from TIC by the computer.
Results and Discussion
Data obtained from qualitative and quantitative determination of the oil samples are
shown in Table 1. Twenty seven components were identified in the oil of S. littoralis
which represented 85.5% of the total composition of the oil. Cyperene (18.7%) was
the dominant constituent. The second major compound was cyperotundone (14.8%).
Also, the oil had significant amounts of isorotundene (8.2%), β-selinene (5.6%),
isocyperol (5.3%) and β-pinene (4.5%).
Chemical analysis of the oil of S. wardianus resulted in the identification of
twenty seven components, accounting for 86% of the oil content (Table 1). The main
constituents of the oil were cyperene (24.1%), cyperotundone (11.1%), cyperol
(6.1%), isorotundene (5.9%), mustacone (5.1%) and isocyperol (4.8%).
Comparison of Essential Oil Constituents of Scirpus Littoralis Schrad. S291
Table 1. Percentage compound of the oil of S. littoralis and S. wardianus
Composition RIa 1 2
α-Pinene 937 1.7 2.3
α-Sabinene 970 0.1 -
β-Pinene 974 4.5 3.1
Sabinene hydrate trans 1060 0.2 0.7
Camphor 1126 - 0.9
Borneol 1155 - -
Cyprotene 1345 0.1 0.1
Cypera-2,4-diene 1351 - 0.3
α-Cubebene 1360 2.5 3.1
β-Cubebene 1387 0.1 -
α-Copaene 1387 - 0.2
Cyperene 1390 18.7 24.1
β-Damascone 1394 0.2 0.4
β-Caryophyllene 1418 0.3 -
Caryophyllane-2-6-
β
-oxide 1425 0.4 0.7
α-Humulene 1454 - 0.1
Rotundene 1460 - -
β-Selinene 1485 5.6 3.3
α-Selinene 1492 0.1 -
α-Calamenene 1498 - -
α-Muurolene 1499 - 0.2
t-Calamenene 1512 4.1 1.8
β-Calamenene 1514 - -
δ-Cadinene 1517 0.6 -
α-Calaocrene 1542 - -
Isorotundene 1560 8.2 5.9
Caryophyllene oxide 1576 0.2 0.4
Isocyperol 1593 5.3 4.8
Cyperol 1600 1.5 6.1
t-Cadinol 1616 2.5 3.1
Cubenol-1-epi 1619 0.1 0.2
α-Muurolol 1630 1.5 2.7
t-Muurolol 1632 2.2 0.3
Cubenol 1636 0.2 -
α-Cadinol 1640 2.4 1.8
Caryophyllene epoxide 1660 0.1 -
Mustacone 1670 3.4 5.1
Cyperotundone 1680 14.8 11.1
α-Cyperone 1706 3.9 3.2
Total -- 85.5 86
1 = S. littoralis, 2 = S. wardianus, a: Kovats Index
According to these results, in both species S. littoralis and S. wardianus
sesquiterpene hydrocarbons (56.6% and 52.9%, respectively) and oxygenated sesquiterpenes
S292 A. FEIZBAKHSH et al.
(22.2% and 25.7%, respectively) were the predominant groups. As can be seen, the
monoterpene fraction of both oils was relatively small, representing (6.7%) and
(7.4%), respectively of the total oils.
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