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Quantitative and Qualitative Study of Bioactive Compounds of Essential Oils of the Medicinal Plant Artemisia sieberi Grown in Lorestan (Iran) by use of GC-MS Technique
Organic Chemistry: Current Research

Organic Chemistry: Current Research
Open Access

ISSN: 2161-0401

+44 20 3868 9735

Research Article - (2012) Volume 1, Issue 4

Quantitative and Qualitative Study of Bioactive Compounds of Essential Oils of the Medicinal Plant Artemisia sieberi Grown in Lorestan (Iran) by use of GC-MS Technique

Noorkhoda Yousefzadeh1, Javad Zeinivand2* and Mohammad Hadi Meshkatalsadat3
1Lecturer of Organic Chemistry, Darreh Shahr Islamic Azad Uiversity, Iran
2Department of Chemistry, Faculty of Science, Ilam University, Ilam, Iran
3Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran
*Corresponding Author: Javad Zeinivand, Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran, Tel: +989188415394 Email: ,

Abstract

Artemisia sieberi belongs to the Asteraceae family and genus Artemisia. In this study, essential oils were extracted from all aerial parts of Artemisia sieberi by kelvenger set with the utilization of hydrodistillation method. By use of GC/ MS technique, the chemical components of essential oil were identified. About 50 components with the help of GC/MS technique were identified which encompassed 96.74% of the whole essential oil. The essential oil yield as a result of hydrodistillation, 0.48% (weight/weight) was obtained (it has been based on dried materials). Trans-para mentha-1(7), 8-dien-2-ol (22.9%), α-terpineol (10.23%), 1,8 cineole (10.22%), β-thujone (6.78%), cis-sabinol (6.78%), linalool (4.58%), dihydrocarveol (3.71%) and geranyl acetate (3.32%) were the major identified compounds. Oxygenated monoterpens group had the highest percentage of essential oil. Because the type and percentage of plant essential oil compounds in each region is different with other regions, therefore, the aim of this investigation was extraction and identification of the chemical compositions of essential oils in Artemisia sieberi for its uses in various medicinal purposes.

Keywords: Artemisia sieberi; α-terpineol; 1,8 cineole; β-thujone; GC/MS

Introduction

Artemisia sieberi belongs to the Asteraceae family and from genus Artemisia. In Iran, there are 34 species in this genus that are from one or several years and are scattered throughout Iran [1-4]. Exclusive species in Iran include:

Artemisia kermanensis, Artemisia melanilepis and Artemisia sieberi. Their main growth is located in mediterranean and temperate regions of Asia, but now grows around the world, especially in the regions of France, Central Europe, North Africa and Iran [1,2].

Artemisia sieberi plant which was examined in this study is known as “Torkh” and is locates in the dialect, those who live in the desert. This plant is very ramose grayish green, dense, colony form, with a taproot, split wood is thick at the end; the plant height is 30 to 50 cm. All plant organs including stems, leaves, flowers and fruits and seeds have a very spicy and penetrating aroma. These plants have a wide range of habitats in the loamy, sandy and clay loamy soils. Aerial parts of plants will be used as medicinal Artemisia organs. Local people use to kill the virus and prevent muscle cramps from the aerial parts of Artemisia sieberi [5,6].

Many Artemisia species are rich sources of various types of biologically active compounds and have antibacterial, antifungal and antioxidant activities [6-9]. This plant has carminative effects, resolving cough and headache, anti-worm, with disinfective and insecticidal properties. It also strengthens the heart and muscle relaxants. It is necessary to strengthen the weak spirit present in the first herbal medicine; in Chinese herbal medicine has used it for menstrual disorders. It stimulates the uterus and has anti-microbial properties. It is effective on dermatophyte fungi such as Epidermophyton floccosum, Trichophyton rubrum, Trichophyton mentagrophytes, Microsporum canis [1,2,10]. Researchers were investigated the effects of climatic factors on the development of mountain and plain Artemisia in Isfahan province using multivariate statistical methods [10]. The main components found in Artemisia [11-15] collected by GC/MS technique from different parts of Iran is in accordance with Table 1, has been reviewed by Iranian researchers on mountain Artemisia extract in plasma lipoproteins and the amount of colostrum in the past artroze hypertriglyceridemia in rabbits [16]. The purpose of this study was to identify the constituents in essential oils extracted from plants and also to determine the percentage of each compound in the essential oil of Artemisia sieberi which is to be used as a drug, according to type and percentage the plant essential oil compounds differs from region to region.

Entry Region Specie The main compounds
1 Tabriz [11] Artemisia fragrans 1,8-cineole (52.1%) and α-thujon (34.8%)
2 South of Khorasan [12] Artemisia sieberi bess. β-thujon, α-thujon, camphor, verbenol, para-mentha-1,5-dien-8-ol and davanon
3 South of Khorasan [13] Artemisia khorasanica Davanon (36.4%), para-cymene (16.55%), (Z) citral (8%) and β-ascaridol (5.95%)
3 Semnan [14] Artemisia sieberi Camphor (49.3%), 1,8-cineole (11.1%) and bornyl acetate (5.8%)
4 North of Tehran [15] Artemisia sieberi Camphor (44%), 1,8-cineole (19%) and camphene (5%)

Table 1: The main components found in aromatic Artemisia collected from Different parts of Iran.

Materials and Methods

Collection of plant material

The aerial parts (stem, leaf and flower) of Artemisia sieberi were gathered in surrounding areas Khorramabad, Lorestan in June 2011. Then, the samples dried for 10 days under the shadow of sunlight and sent to a lab in Lorestan University for analysis.

Extraction of the essential oil

For essential oil extraction, Clevenger system and hydrodistillation method was used. About 100 g of dried samples were submitted for 3.5 hours to hydrodistillation using a Clevenger apparatus to produce the essential oil. The gathered liquid was in two parts: oil (essential oil) and water. The oil part was separated by a special syringe. Then, it is dehydrated with sodium sulphate and stored in special tubes covered with aluminium foil (sheet) to keep from light. Keep the tubes in dry and cold refrigerators for the next step.

GC/MS analysis

The analysis of the essential oils was performed with Shimadzu gas chromatography model GC-17A coupled with Shimadzu mass spectroscopy model QP5050. Separation of compounds will be performed in fused silica capillary DBX-5 column (30 m×0.25 mm inner diameter, with 0.25 μm film thickness). The oven temperature was programmed from 40°C to 150°C at 3°C/min rate, then held isothermal for 10 min and finally raised to 250°C at 10°C/min. The quality of mass spectrometer was quite similar to gas spectrometer and for GC/MS detection an electron ionization system with ionization energy of 70 eV was used. Carrier gas was helium at a flow rate of 1.9 ml/min.

Identification of compounds

After providing an injection of essential oil to GC system, it was the best condition for separating. Then, by using of coupled gas chromatography with mass spectroscopy (GC-MS), the quantity and quality of essential oil components were recognized. The constituent compounds of the essential oils 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 compounds was made by comparison of their mass spectra with those of the internal reference mass spectra library data GC-MS system (wiley 229) and with authentic compounds and confirmed by comparison of their retention indices with authentic compounds or with the compounds reported in literature [17]. The relative percentage of each compound obtained according to it’s under peak area in GC chromatogram, without the use of correction factors.

Results and Discussion

In this study, essential oils were extracted from all aerial parts of Artemisia sieberi by kelvenger set with the utilization of hydrodistillation method. By use of Gas Chromatography-Mass Spectrometry (GC/MS) technique, about 50 compounds were identified which encompassed 96.74% of the whole essential oil. The essential oil yield 0.48% (w/w) was obtained. Trans-para mentha- 1(7), 8-dien-2-ol (22.9%), α-terpineol (10.23%), 1,8 cineole (10.22%), β-thujone (6.78%), cis-sabinol (6.78%), linalool (4.58%), dihydrocarveol (3.71%) and geranyl acetate (3.32%) were the major identified compounds. Compounds identified in Table 2 are consistent. Studies show that between different groups of monoterpenes, oxygenated monoterpenes has the highest concentration (79.04%).

Name of compounds RI A%
Santolina triene 909 0.19
Tricyclene 927 0.25
Artemisia triene 930 0.11
α-Pinene 939 0.45
Camphene 954 2.46
Verbenene 968 2.00
β-Pinene 979 0.22
Myrcene 991 0.27
Yomogi alcohle 999 2.50
α-Phellandrene 1003 0.81
α-Terpinene 1017 0.49
Ortho-Cymene 1026 1.38
1,8 Cineole 1031 10.22
Santolina alcohle 1040 0.81
-γ Terpinene   1060 0.99
Linalool oxide (cis) 1087 0.46
Terpinolene 1089 0.95
ρ-Cymenene 1091 0.76
Linalool 1097 4.58
β-Thujone 1114 6.78
Sabinol (cis) 1143 6.78
Pinene hydrate (cis) 1144 0.4
Thujol 1169 0.4
Santolinyl acetate 1175 1.3
(-) Lavandoulol 1181 1.51
ρ-Cymene 8-ol 1183 0.38
Mentha 1(7), 8-dien-2-ol (trans, para) 1189 22.9
α-Terpineole 1189 10.23
Dihydro carveole 1194 3.71
Verbenone 1205 0.57
Pulegone 1237 0.02
unknown - 0.85
Carvacrol methyl ether 1245 0.21
Piperitone 1253 0.12
Chrysanthenyl acetate (cis) 1265 1.26
Bornyl acetate 1289 1.17
Lavandulyl acetate 1290 0.12
Carvacrol 1299 0.69
Carvyl acetate (trans) 1342 0.1
α-Terpinyl acetate 1349 0.16
Geranyl acetate 1381 3.32
Jasmone (Z) 1393 0.44
 (+) Arromadendrene 1441 0.34
Geranyl iso butanoate 1515 0.32
Globulol 1585 1.1
Widdrol 1599 0.27
Hexa decane 1600 0.27
β-Oplopenone 1608 0.16
Hepta decane 1700 0.57
Benzoin 1804 0.39
Monoterpene hydrocarbons   11.33
Oxygenated monoterpenes   79.04
Sesquiterpene hydrocarbons   0.34
Oxygenated sesquiterpenes   2.03
Unknown compounds   0.85
Other compounds   3.15
Total   96.74

RI: retention indices relative to C6-C24 n-alkanes on the DB-5 column.
A: percentage of essential oils composition of Artemisia sieberi
Artemisia sieberi
by GC and GC/MS on DB-5 column

Table 2: Identification of essential oil compounds in the plant.

In this study, there are some similarities between the main components of essential oils in Artemisia and with the previous studies, for example, β-thujone is reported as one of the main components of essential oils in species of Artemisia sieberi and also para menta 1,5- dyen-8–ol, para menta 1 (7), 8–dyen-2–ol is reported as one of the main compounds [12]. Also, other researchers have been reported about the same species 1,8 cineol as one of the main essential oil compounds [11,14,15]. Furthermore, there are considerable qualitative and quantitative differences between essential oils composition of Artemisia sieberi in this study, with those of previously reported from different parts of Iran. In conclusion, chemical differentiation of Artemisia essential oils might be correlated with environmental conditions, geographic, climatic, and genetic, plant age, soil, phase of vegetation, anatomical part of plant and harvesting season [18-22], so there are essential differences between the compounds of plants that have been previously reported with this plant. Because the type and concentration of plant essential oils and chemical compounds is differs from one region to other. Therefore, in this case it is necessary to perform more studies in different places of Iran for various medicinal purposes.

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Citation: Yousefzadeh N, Zeinivand J, Meshkatalsadat MH (2012) Quantitative and Qualitative Study of Bioactive Compounds of Essential Oils of the Medicinal Plant Artemisia sieberi Grown in Lorestan (Iran) by use of GC-MS Technique. Organic Chem Curr Res 1: 109.

Copyright: ©2012 Yousefzadeh N, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.