Journal of Applied Chemical Research, 18, 29-34 (2011)

Journal of App l ied Chemical Research

www.jacr.k iau.ac. i r

Comparison of Essential Oils Composition of Stem, Leaf and Flower from Artemisia deserti Kracsh

M. Kazemi1*, S. Shafizadeh2, K. Larijani3

1*Department of Applied Chemistry, Qom Branch, Islamic Azad University, Qom, Iran. 2Department of Applied Chemistry, Shahr-e-Rey Branch, Islamic Azad University, Tehran. Iran.

3Department of Chemistry, Science and Research Campus, Islamic Azad University, Tehran. Iran.(Received 12 December 2010; Final version received 22 April 2011)

AbstractThe essential oils from different parts of Artemisia deserti Kracsh were determined by a combination of Gas Chromatography (GC) and Gas Chromatography-Mass Spectroscopy (GC-MS) methods. Among 42 identified compounds, camphor (15.9%, 22.5% and 18.0% in stem, leaf and flower respectively) was the main components while 1,8-cineole (12.6% and 10.4%) and trans-thujone (11.8% and 16.4%) were found as the other major constituents in leaf and flower, respectively. Keywords: Artemisia deserti, Compositae, Essential oil composition, camphor, 1,8-cineole, Trans-thujone.

IntroductionThe genus Artemisia (Family: Compositae) contains small herbs or shrubs found in northern temperate regions. Thirty-four species of the genus Artemisia are found in Iran, of which two are endemic; A. melanolepis Boiss. and A. kermanensis Podl. [1, 2]. Several Artemisia species has medicinal importance and are useful in traditional medicine for the treatment of a variety of diseases and complaints. Artemisia annua is a traditional medicinal herb in China. It is presently being cultivated on a commercial scale in China and Vietnam for its Compound sesquiterpene lactone

artemisinin [3]. In addition, A. annua is valued for its essential oil. Although the commercial significance of the oil is limited, it is sometimes used as a fragrance in perfume and cosmetic products [4]. The herb of A. vestita has been widely used in traditional Tibetan and Chinese medicine for a variety of inflammatory diseases, such as rheumatoid arthritis, contact dermatitis and sepsis [5]. A. dracunculus has been used orally as an antiepileptic remedy in which its anticonvulsant potential has been assessed [6]. The genus Artemisia has been investigated chemically in which acetylenic

compounds [7], flavonoids [8], coumarins

* Corresponding author: Dr. M. Kazemi, Assistant Prof., Department of Applied Chemistry, Qom Branch, Islamic Azad University, P.O.Box 37185/364, Qom, Iran. Email: smkazemit@yahoo.com. Tel: +98-251-7780001, Fax: +98-251-7780008.

M. Kazemi et al., J. Appl. Chem. Res., 18, 29-34 (2011)30

[9] and terpenoids, especially sesquiterpene

lactones have been reported [10]. The extract

of the aerial parts of A. deserti, was afforded,

in addition to germacranolide, guanolide,

some monoterpenes and sesquiterpenes [10].

Although numerous reports appear in the

literature on the essential oils of different

species of Artemisia [11-20], to our knowledge

no studies have been reported on the oils of

stems, leaves and flowers of A. deserti. So we

investigated their chemical compositions in

our present study.

Experimental

Plant materials

The aerial parts of A. deserti were collected

during the flowering stage in simindasht area,

province of Tehran, Iran, in August 2009. Voucher

specimens (No. 59084) have been deposited at

the Herbarium of the Research Institute of Forests

and Rangelands (RIFR), Tehran, Iran.

Isolation of the oils

The aerial parts of A. deserti was air-dried (in

the shade at room temperature) and divided

to stems (200 g), leaves (50.0 g) and flowers

(50.0 g). The different parts of A. deserti plant

were subjected separately to hydrodistillation

using a Clevenger-type apparatus for 3 hrs.

After decanting and drying over anhydrous

sodium sulfate, the corresponding yellowish

colored oils were recovered at yields of

0.1%, 0.2% and 0.3% w/w respectively. The

samples were stored in dark glass bottles in a

freezer (-5° C) until further use and analyze.

Gas Chromatography

Analysis was performed on a Shimadzu 15A

gas chromatograph equipped with a split/

splitless (ratio 1:30) injector (250° C) and a

flame ionization detector (250° C). N2 was

used as carrier gas (1 ml/min) and the capillary

column used was DB-5 (50 m × 0.2 mm, film

thickness 0.32 µm). The column temperature

was kept at 60° C for 3 min and then heated to

220° C with a 5° C/min rate and kept constant

at 220° C for 5 min. Relative percentages were

calculated from peak area using a Shimadzu

C-R4A chromatopac without the use of

correction factors.

Gas Chromatography-Mass Spectroscopy

Analysis was performed using a Hewlett-

Packard 5973 with a HP-5MS column (30 m x

0.25 mm, film thickness 0.25 µm). The column

temperature was kept at 60° C for 3 min and

programmed to 220° C at a rate of 5° C/min and

held isothermal at 220° C for 5 min. The flow

rate of Helium as carrier gas was 1 ml/min. MS

were taken at 70 eV, mass rang, 30 to 350 amu

and scan time, 2 scan/ sec. The compounds were

identified by comparing the RRI, DB5 with

those reported in the literature and by comparing

their mass spectra with either the Wiley library

or with published mass spectra [21-23]. The

retention indices for all the components were

M. Kazemi et al., J. Appl. Chem. Res., 18, 29-34 (2011) 31

determined according to the Van Den Dool

method, using n-alkanes as standards [24].

Results and DiscussionThe volatile constituents obtained from stem, leaf and flower of A. deserti are listed in Table

I in which the percentage and retention indices of the components are given. Analysis of the stem, leaf and flower oils of A. deserti resulted in the identification of 42 constituents, representing 92.9%, 94.9% and 93.0% of the oils, respectively (Table 1).

Table І. Comparative Percentage Composition of the Stem, Leaf and Flower Oils of A. deserti.

flowerleafstemRICompoundt.1.02.8700heptanet.3.28.8 .800octane0.7t.t.909santolina trien0.6t.t.930alpha-thujene4.03.03.0939alpha-pinene4.86.42.6954camphene1.90.7t.975sabinene1.5t.t.979beta-pinenet.0.82.71000decane0.8t.t.1017alpha-terpinene1.82.01.31025p-cymene10.412.66.510311,8-cineole1.20.5t.1060gamma-terpinene1.0t.t.1070cis-sabinene hydrate0.4t.t1089terpinolene0.4tt1091linalool1.90.9t.1102alpha-thujone16.411.86.01114trans-thujonet.0.5t.1128chrysanthenone0.4t.t.1133iso-3-thujamolt.t.5.11145trans-verbenol18.022.515.91146camphor2.32.0t.1162pinocarvone5.74.94.41164trans-chrysanthenol3.01.6t.1177terpinen-4-ol2.00.6t.1188alpha-terpineol1.60.5t.1194myrtenolt.0.5t.1196myrtenal0.9t.t.1205verbenone1.1t.t.1243carvone0.8t.t.1265chrysanthenyl acetate0.3t.t.1331(E)-patchenol0.2tt.1362neryl acetatet.0.5t.1379(E)-methyl cinnamate

M. Kazemi et al., J. Appl. Chem. Res., 18, 29-34 (2011)32

1.80.8t.1394(Z)-Jasmone

1.13.97.91524artedouglasia oxide C

1.14.27.91536artedouglasia oxide A

1.01.44.01561artedouglasia oxide D

2.63.94.31566davanone B

0.81.93.11578spathulenol

0.51.22.51583caryophyllene oxide

t.1.14.11608beta-oplopenone

93.094.992.9Total

Group components

15.910.65.6Monoterpene hydrocarbones

68.259.237.9Oxygenated monoterpenes

tttSesquiterpene hydrocarbones

7.117.633.8Oxygenated sesquiterpenes

1.87.515.6Other components

t = trace < than 0.05%

The main components in oils from three parts were camphor (15.0%, 22.5% and 18.0%). The other major constituents in leaf and flower were 1,8-cineole (12.6% and 10.4%) and trans-thujone (11.8% and 16.4%) respectively. Comparison of the main components of stem, leaf and flower of A. deserti and their chemical structures are shown in Figure 1 and 2 respectively.

Figure 1. Chemical Structures of the Main Compounds of A. deserti.

Figure 2. Comparison of the main components of stem, leaf and flower of A. deserti.

The leaf and flower oils of A. deserti were found to be rich in oxygenated monoterpenes (68.2% and 59.2% respectively) while oxygenated monoterpenes (37.9%) and sesquiterpenes (33.8%) were the major fractions in stem. The three samples were poor in sesquiterpene hydrocarbons and other compounds.

M. Kazemi et al., J. Appl. Chem. Res., 18, 29-34 (2011) 33

Oxygenated sesquiterpenes constitute are the minor fraction of the leaf and flower oils (7.1% and 17.6%), but monoterpene hydrocarbons amounted to 15.9%, 10.6% and 5.6% of the oils, respectively.In some studies on the essential oils of other Artemisia species, 1,8-cineole and bornane derivatives were reported as the main constituents.1,8-cineole (27.8%, 25.7%, 19.0%, 14.3%) and camphor (37.9%, 35.0%,44%, 45.5%) were obtained to be major constituents of the oils of A. scoparia [11], A. diffusa [12], A. sieberi [13] and A. aucheri [14]. In other researches, thujone derivatives were reported as the main constituents. These

compounds were obtained as the major

components of the oils of A. absinthium

[11], A. fragrans [15], A. herba-alba [16], A.

khorassanica [17] and A. verlotiorum [18].

The essential oil of areal parts from A.

deserti was investigated. Ahmadi et. al. [19]

and Rustaiyan et. al. [20] reported piperiton

(52.0% and 8.6%), camphor (15.7% and

45.5%) and 1,8-cineole (11.8% and 16.7%) as

the major components, respectively. In present

work, piperitone was not detected.

Other investigations on essential oils also

confirm our findings indicating the different

oil components depending on the species,

environment, flowering stage and etc.

Subsequently, the influence of environmental

factors as well as the quality of the seeds on the

composition of essential oils cannot be ruled

out [25]. The factors, such as day and night

temperatures, photoperiod and light intensity

are important in essential oil compositions

[26]. 1,8-Cineole and camphor are well-

known antimicrobial compounds isolated

from different plant species [27]. These oils

can be the potent antimicrobial agent.

Conclusion

In our work, the content and presence of

particular essential oil components were

followed in selected species of the Artemisia

genus. We have identified 42 major and minor

constituents of essential oils from selected

species. The proportional amount of these

compounds was different for various parts of

this herb such as stems, leaves and flowers.

The main constituents of different parts of A.

deserti are reported in such species of genus.

These results justify the traditional use of this

Artemisia.

Acknowledgment

This research supported by Department of

Applied Chemistry, Islamic Azad University,

Shahr-e-Rey Branch as MSc thesis.

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