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RESEARCH ARTICLE
Year : 2009  |  Volume : 1  |  Issue : 3  |  Page : 120-124 Table of Contents     

Chemical Composition and Antimicrobial Activity of Artemisiatschernieviana Besser from Iran


1 Department of Applied Chemistry and Faculty of Medicine, Qom Branch, Islamic Azad University, P.O.Box 37185/364, Qom, Iran
2 Department of Chemistry, Science and Research Campus, Islamic Azad University, Tehran, Iran
3 Iran Research Institute of Forests and Rangelands, Tehran, Iran

Date of Submission20-Feb-2009
Date of Acceptance09-Apr-2009
Date of Web Publication2-Jan-2010

Correspondence Address:
Masoud Kazemi
Department of Applied Chemistry and Faculty of Medicine, Qom Branch, Islamic Azad University, P.O.Box 37185/364, Qom
Iran
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Source of Support: None, Conflict of Interest: None


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   Abstract 

The oil obtained from hydrodistillation of the aerial parts of Artemisia tschernieviana was analyzed by GC and GC/MS. The main constituents of the 30 identified components were p-cymene (21.3%), β-pinene (17.8%), α-pinene (9.4%), γ-terpinene (9.1%), (Z)-cis-ocimene (8.8%), and α-cadinol (8.1%). This species is rich in monoterpenes. Antimicrobial activity was determined against six bacterial strains and one fungal strain. The results show that this oil is active against all the tested strains.

Keywords: Artemisia tschernieviana Besser; Essential oil; Antimicrobial activity; p-cymene; β-pinene; α-pinene; γ-terpinene; (Z)-beta-ocimene; α-cadinol


How to cite this article:
Kazemi M, Dakhili M, Rustaiyan A, Larijani K, Ahmadi MA, Mozaffarian V. Chemical Composition and Antimicrobial Activity of Artemisiatschernieviana Besser from Iran. Phcog Res 2009;1:120-4

How to cite this URL:
Kazemi M, Dakhili M, Rustaiyan A, Larijani K, Ahmadi MA, Mozaffarian V. Chemical Composition and Antimicrobial Activity of Artemisiatschernieviana Besser from Iran. Phcog Res [serial online] 2009 [cited 2020 Feb 25];1:120-4. Available from: http://www.phcogres.com/text.asp?2009/1/3/120/58120


   Introduction Top


Artemisia (Asteraceae) is one of the largest and most widely distributed genus of the approximately 60 genera in the Anthemideae tribe. This genus comprises more than 400 species, and is predominantly distributed in the northern temperate region of the world in the 0-50 cm precipitation area. Thirty-four of them have been reported in Iran and some are endemic [1],[2] . Some substances from the genus have shown antimalarial, antiviral, antitumoral, antipyretic, antihemorrhagic, anticoagulant, antianginat, antioxidant, antihepatitis, anti ulcerogenic, antispasmodic, anticomplementary and interferon­inducing activity [3],[4] . A. annua (Qinhaosu) is a traditional medicinal herb in China. It is now cultivated on a commercial scale in China and Vietnam for its antimalarial sesquiterpene(a lactone artemisinin) [5],[6] and essential oil. The extract of the aerial parts of A. diffusa collected in the Province of Khorassan (Iran) afforded, in addition to several eudesmanolides, a new type of sesquiterpene lactone (Tehranolide) with an endoperoxide group that probably has the same effect as the antimalarial agent artemisinin. The antimalarial properties of the extract and the fraction that contains sesquiterpene lactones including Tehranolide have been reported [7],[8] . A. austriaca and A. spicigera are odorous herbs used as antiseptics and stomachics in folk medicine [9] . A. vestita is a herb that has been widely used in traditional Tibetan and Chinese medicine for treating inflammatory diseases such as rheumatoid arthritis and contact dermatitis anepsis [10] . A. dracunculus has been used orally as an antiepileptic in which its anticonvulsant potential has been assessed [11] . Studies on Artemisia has ascertained the presence of coumarin [12] , acetylenic compounds and sesquiterpene lactones [13],[14],[15],[16],[17],[18] . Although literature f the essential oils of different species of Artemisia [19],[20],[21],[22],[23],[24],[25],[26],[27],[28],[29],[30],[31],[32],[33],[34],[35],[36],[37] and its antimicrobial effects [22],[23],[24],[25],[26],[27],[28],[29],[30],[31],[32],[33],[34],[35],[36] is prevalent, no studies have been reported on the oil of A. tschernieviana. Therefore, we decided to investigate its chemical compositions and antimicrobial activity.


   Material and Methods Top


Plant material - The aerial parts of A. tschernieviana were collected during the flowering stage in the Behshahr province of Mazandaran, Iran, in October 2007. Voucher specimens (no. 88489) have been deposited at the Herbarium of the Research Institute of Forests and Rangelands (TARI), Tehran, Iran.

Preparation of oil

The air-dried aerial parts of A. tschernieviana (110.0 g) were subjected to separate hydrodistillation for 3 h using a Clevenger-type apparatus. After decanting and drying over anhydrous sodium sulfate, the corresponding yellowish oil was recovered in yields of 0.80 % w/w.

GC-MS analysis

The oil was analyzed 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 kept constant at 220°C for 5 min. The flow rate of Helium as carrier gas was 1 mL/min. MS readings were taken at 70 eV, mass range, 30 to 350 amu, and scan time, 2 scan/ sec. The constituents of each oil was identified by comparing their mass spectra and retention indices (RIs) with those in the literature and those authentic samples [37] . GC analysis was performed on a Shimadzu 15A gas chromatograph equipped with a spilt/spiltless (ratio 1:30), injector (250°C) and a flame ionization detector (250°C). N 2 was used as carrier gas (1 mL/min) and DB­5 (50 m x 0.2 mm, film thickness 0.32 pin) was used as the capillary column . The column temperature was kept at 60°C for 3 min and then heated to 220°C with a 5°C/min rate and maintained constant at 220°C for 5 min. Relative percentage amounts were calculated from peak area using a Shimadzu C-R4A chromatopac without using correction factors.

Microorganisms and Antimicrobial Studies

The antibacterial and antifungal activity of the essential oil was evaluated by the disc diffusion method using Mueller-Hinton and Sabouraud Dextrose agar, respectively [38] . The bacteria included Staphylococcus aureus Scientific Name Search eus (ATCC 25923),  Escherichia More Details coli (ATCC 25922), Entobacter aerogenes (ATCC 49469), Klebsiella pneumoniae Scientific Name Search  (ATCC 27736), Bacillus creus (ATCC 6633), Bacillus subtilis Scientific Name Search  (ATCC 9372), and the fungi included Candida albicans (ATCC 6258). The microorganisms were obtained from the Research Center of Science and Industry, Tehran, Iran.

A serial dilution of the oil was prepared in Mueller­Hinton and Sabouraud dextrose broth for bacteria and fungi, respectively. The oil was diluted using water and ethanol solvents. The solvents, at an appropriate concentration, were also used as a negative control.The standardized suspension of bacteria and fungi was inoculated into each tube. The tubes were incubated at 37°C for 24 h for bacteria and at 30°C for 48-72 h for fungi. The lowest oil concentration, where there was no visible growth, was the minimum inhibitory concentration (MIC) when compared to control.

To determine the Minimum Bactericidal Concentration (MBC) and Minimum Fungicidal Concentration (MFC), for each set of test tubes in the MIC determination, a loopful of broth was collected from those tubes that did not show any growth and inoculated on Mueller­Hinton agar (for bacteria) and Sabouraud Dextrose Broth agar (for fungi) by streaking. Plates inoculated with bacteria and fungi were then incubated at 37°C for 24 h and 30 °° C for 48-72 h, respectively. After incubation, the concentration at which no visible growth was seen was noted as MBC (for bacteria) and MFC (for fungi). All the experiments were carried out in triplicate and the mean was calculated.


   Results and Discussion Top


The percentage and retention indices of the components of the volatile constituents obtained from A. tschernieviana are listed in [Table 1]. Thirty compounds, representing 98.3% of the total constituents in the oil of A. tschernieviana, were characterised by p-cymene (21.3%) and β-pinene (17.8%) followed by α-pinene (9.4%), γ-terpinene (9.1%), (Z)-cis-ocimene (8.8%), and α-cadinol (8.1%). Monoterpene hydrocarbons constitute the major fraction of the oil (72.9%), while sesquiterpene hydrocarbons accounted for 0.9%. Oxygenated monoterpenes and oxygenated sesquiterpenes amounted to 10.4% and 14.0% of the oil, respectively. This Artemisia is rich in monoterpenes.

In some studies on the essential oils of other Artemisia species, p-cymene (17.4%, 16.8%, 16.5%, and 16.5%) is also characteristic of the oils of A. scoparia [19] , A. absinthium [20],[21] , and A. khorassanica [22] .

Pinane derivatives are found in the oils of some Artemisia species, for example, α-pinene is found in the oils of A. annua [23] and A. biennis [24] , β-pinene in A. absinthium [21] A. campestris [25],[26] , A. scoparia [27] , and A. moorcroftiana [28] , and γ-­terpinene in A. scoparia [19] .

(Z)-β-ocimene
, the main component of the oil of A. tschernieviana, is also characteristic of the oils of A. glauca [29] and A. afro [30] .

In another study, β-Pinene (24.0-49.8%) was found to be the main component of the oil of A. campestris from Tunisia [31] . Monoterpene hydrocarbons were shown to be the major fraction (58.8-88.6%), and were mainly composed of β-Pinene (24.0-49.8%), α-pinene (5.9-12.5%), β-cymene (3.4-9.4%), limonene (4.9-9.3%), (Z)-β-ocimene (0.2-5.5%), and γ-terpinene (2.0-6.5%).

In a similar research, from four areas of south-eastern Tunisia [32] , β-Pinene (24.2-27.9%), p-cymene (17.4­22.3%), and α-pinene (4.1-11.0%) were observed to be the major constituents.

Camphor and 1,8-cineole were reported as the main constituents of many species of Artemisia [13] ; however, in our research these compounds were found in traces and as minor constituents, respectively.

Cadinane derivatives are characterized in the oils of A. campestris [31],[33] whereas in our study α-cadinol was detected.

Results of the antimicrobial activities of the oil are shown in [Table 2]. Antimicrobial activity was determined against six bacterial strains and one fungal strain. The results show that this oil is active against all the tested strains. The oil has shown a maximum zone of inhibition against Entobacter aerogenes. Staphylococcus aureus, Bacillus subtilis, and Candida albicans were the most sensitive microorganisms to the essential oil (having an MIC value of 312.5 pg/ml).

Previous studies showed that terpene alkoholes are well-known antimicrobial compounds isolated from different plant species [34] . The antimicrobial activity of the oil could, in part, be associated with terpene alkoholes such as linalool. These results may partly justify the traditional use of this Artemisia.

Composition and antimicrobial activity of the volatile oil of A. kopetdaghensis from Iran were investigated [35] . The minimum inhibitory concentration was determined and the oil showed a moderate antimicrobial activity.

In another study, the essential oil of A. lavandulaefolia exhibited considerable inhibitory effects against all obligate anaerobic bacteria tested, while its major compounds demonstrated different degrees of growth inhibition [36] .

 
   References Top

1.K.H. Rechinger. Artemisia in Flora Tranica. Compositae, No. 158, K.H. Rechinger, and I.C. Hedge, Akademische Druck and Verlagsanatalt, Graz, Austria, p. 185-216, (1980).  Back to cited text no. 1      
2.V. Mozaffarian. A Dictionary of Iranian Plant Names, Farhang Moaser Publishers, Tehran, Iran, (1996).  Back to cited text no. 2      
3.Rustaiyan, H. Nahrevanian and M. Kazemi. Effects of Extracts of Artemisia diffusa against plasmodium berghei, as a New Antmalarial Agent.BIT 's SthAnniversary congress of International Drug Discovery Science and Technology(IDDST) May 28-June 5, Shanghai, China, (2007).  Back to cited text no. 3      
4.R.X. Tan, W.F. Zheng and H.Q. Tang. Biologically Active Substances from the Genus Artemisia, Planta Medica. 64: 295-302, (1998).  Back to cited text no. 4      
5.G.Q. Li, X.B. Guo, R. Jin, Z.C. Wang, H.X. Ran and Z.Y. Li. Clinical studies on treatment of cerebral malaria with ginghaosu and its derivatives, J. Trad. Chin. Med. 2: 125-­130,(1982).  Back to cited text no. 5      
6.D.L. Klayman, A. J. Lin, N. Acton, J.P. Scovill, J.M. Hochu, W.K. Milkhous, A. D. Theoharides and A.S. Dobek. Isolation of artemisinin (Qinghaosu) from Artemisia aanu a growing In the United States, J. Nat. Prod. 47: 715-716, (1984).  Back to cited text no. 6      
7.Rustaiyan, H. Nahrevanian and M. Kazemi. A New antimalarial; effect of extracts of Artemisia diffiisa against plasmodium berghei. Phcog Mag. 17: 1-7(2009).  Back to cited text no. 7      
8.Rustaiyan, H. Sigari, J. Jakopovic and M. Grenz. A sesquiterpene lactonee from Artemisia diffusa. Phytochemistry, 28: 2723-2725, (1989).  Back to cited text no. 8      
9.Z. Guoevenalp, A. Caldr, M. Harmandar and H. Gleispach. The Essential oils of Artemisia austriaca and Artemisia spicigera C. Koch, from Turkey, Flavour and Fragr. J. 13: 26-28, (1998).  Back to cited text no. 9      
10.Y. Sun, Y.H. Li, X.X. Wu, W. Zheng, Z.H. Guo,Y. Li, T. Chen, Z.C. Hua and Q. Xu. Ethanol extract from Artemisia vestita, a traditional Tibetan medicine,exerts anti-sepsis action through down-regulating the MAPK and NF-KB pathways, Int. J. Mol. Med. 17: 957-962, (2006).  Back to cited text no. 10      
11.M. Savyah, L. Nadjafinia and M. Kamalinejad. Antconvulsant activity and chemical composition of Artemisia dracunculus L. essential oil, J. Ethnophannacol. 94: 283-287,(2004).  Back to cited text no. 11      
12.K.S. Rybalko, O.A. Konovalova, V.I. Sheichenko and P.I. Zakharov. Armin-A new coumarin from Artemisia ameniaca, Chem. Nat. Comp.12: 262-265, (1977).  Back to cited text no. 12      
13.Rustaiyan, S. Masoudi, M. Kazemi. Volatile Oils Constituents from Different Parts of Artemisia ciniformis Krasch. Et M. Pop. ex Poijak and Artemisia incana (L.) Druce. from Iran, J. Essent. Oil Res. 19: 548-55, (2007).  Back to cited text no. 13      
14.Rustaiyan, H. Sigari, J. Jakopuvic and M. Grenz. A sesquiterpene lactone from Artemisia diffusa. Phytochemistry. 28: 2723-2725,(1989).  Back to cited text no. 14      
15.Rustaiyan, K. Zare, M.T. Ganji and H.A. Sadri. A melampolide and two dihydro artemorin derivatives from Artemisia gypsacea. Phytochenaistiy. 28: 1535-1536, (1989).  Back to cited text no. 15      
16.J.A. Marco, F. Sanz-Cervera, F. Sancenon, A. Rustaiyan and M. Kardar. Sesquiterpene lactone from Iranian Artemisia species. Phytochemistry. 34: 1561-1564, (1993).  Back to cited text no. 16      
17.Rustaiyan, A. Bamoniri, M. Raffatrad, J. Jakupovic and F. Bohlman. Eudesmane derivatives and highly oxygenated monoterpene from Iranian Artemisia species. Phytochemistry. 26: 2307-2310, (1987).  Back to cited text no. 17      
18.J. Sanz, A. Rustaiyan and A. Marco. A melarnpolide from Artemisia oliveriana. Phytochemistry. 29: 2919-2921, (1990).  Back to cited text no. 18      
19.Kapoor, M. Ali, S.R. Mir, M. R.M. Rafiullah. Essential oil constituents of aerial parts of Artemisia scoparia Waldst. & Kit. Flav. Fragr. J. 19: 109-111, (2004).  Back to cited text no. 19      
20.Basta, O. Tzakou, M. Couladis and M. Pavlovic. Chemical Composition of Artemisia absinthium L. from Greece. J. Essent. Oil Res. 19: 316-318, (2007).  Back to cited text no. 20      
21.K. Morteza-Semnani, M. Akbarzadeh. Essential Oils Composition of Iranian Artemisia absinthium L. and Artemisia scoparia Waldst. et Kit., J. Essent. Oil Res. 17: 321-322, (2005).  Back to cited text no. 21      
22.J. Hadian, T. Ramak-Masoumi, M. Farzaneh, M.H. Miijalili, S. Nejad-Ebrahimi and M. Ghorbani. Chemical Compositions of Essential Oil of Artemisia khorassanica Podl. and its Antifungal Activity on Soil-Born Phytopathogens, J. Essent. Oil Bearing Plants. 10: 53-59, (2007).  Back to cited text no. 22      
23.Rasooli, M.B. Rezaee, M.L. Moosavi and K. Jaimand. Microbial Sensitivity to and Chemical Properties of the Essential Oil of Artemisia annua L., J. Essent. Oil Res. 15: 59-62, (2003).  Back to cited text no. 23      
24.F. Nematollahi, A. Rustaiyan, K. Larijani, M. Nadimi and S. Masoudi. Essential Oil Composition of Artemisia biennis Willd. and Pulicaria undulata (L.) C.A. Mey., Two Compositae Herbs Growing Wild in Iran. J. Essent. Oil Res. 18: 339-341, (2006).  Back to cited text no. 24      
25.Bellomaria, G. Valentini, E. Biondi. Chemotaxonomy of Artemisia variabilis ten. and A. eampestris L. ssp. glutinosa (Ten.) Briq. et Cavill. (Asteraceae) from Italy. J. Essent. Oil Res. 13:90-94,(2001).  Back to cited text no. 25      
26.J.C. Chalchat, P. Cabassu, S.D. Petrovic, Z.A. Maksimovic, M.S. Gorunovic. Composition of essential oil of Artemisia campestris L. from Serbia. J. Essent. Oil Res. 15: 251-253, (2003).  Back to cited text no. 26      
27.Safaei-Ghomi, A. Bamoniri, M.B. Sarafraz, H. Batooli. Volatile components from Artemisia scoparia Waldst et Kit growing in central Iran. Flav. Fragr. J. 20: 650 - 652, (2005).  Back to cited text no. 27      
28.P. Weyerstahl, H. Marschall, V.K. Kaul. The essential oil of Artemisia moorcroftiana wall. Flav. Fragr. J. 7: 73 - 77, (2006).  Back to cited text no. 28      
29.S. Shatar, X.D. Nguyen, D. Karashawa. Essential oil composition of some Mongolian Artemisia species. J. Essen. Oil Bearing Plants. 6: 203-206, (2003).  Back to cited text no. 29      
30.A.M. Viljoen, S.F. Van Vuuren, T. Gwebu, B. Demiroi, K. Baser, C. Husnti. Geographical Variation and Antinicrobial Activity of African Wormwood (Artemisia afra Jacq.) Essential Oil. J. Essent. Oil Res. 18: 19-25, (2006).  Back to cited text no. 30      
31.Akrout, R. Chemli, M. Simmonds, G. Kite, M. Hammami, I. Chreif. Seasonal variation of the essential oil of Artemisia campestris L. Journal of Essential Oil Research, 15: 333-336, (2003).  Back to cited text no. 31      
32.Akrout, R. Chemli, I. Chreif, M. Hammami. Analysis of the essential oil of Artemisia campestris L. Flav. and Fragr, J., 16:337-339, (2001).  Back to cited text no. 32      
33.A.J.D. Silvestre, A.M.S. Silva, L.M.P.M. Almeida, C.C.L. Pereira and J.A.S. Cavaleiro. The Essential Oil of Artemisia campestris L. subsp. maritima Arcangelis., Acta Horticulturae. 500: 93-96, (1999).  Back to cited text no. 33      
34.S. Inouye, T. Takizawa and H. Yamaguchi. Antibacterial activity of essential oils and their major constituents against respiratory tract pathogens by gaseous contact. Journal of Antimicrobial Chemotherapy. 47: 565-573, (2001).  Back to cited text no. 34      
35.M. Ramezani, J. Behravan, A. Yazdinezhad. Composition and antimicrobial activity of the volatile oil of Artemisia kopetdaghensis Krasch., M.Pop. & Linecz ex Poljak from Iran. Flav. Fragr. J. 21: 869 - 871, (2006).  Back to cited text no. 35      
36.Jeong-Dan, J. Mi-Ran, C. Hwa-Jung, J. Seung-L, M. Sang­Eun, Y. Soon-I, K. Young-Hoi, K. Bong-Seop and S. Yo­Han. Chemical Composition and Antimicrobial activity of the Essential oil of Artemisia lavandulaefolia. 71: 575-577, (2005).  Back to cited text no. 36      
37.R.P. Adams. Identification of Essential oil components by Gas Chromatography/Mass Spectroscopy. Allured Publishing Corp., Carol Stream, IL (1995).  Back to cited text no. 37      
38.E.J. Baron and S.M. Finegold. Bailey and Scott's Diagnostic microbiology, 8th ed. Mosby, St. Louis, MO, USA, (1995).  Back to cited text no. 38      



 
 
    Tables

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