Comparison of the volatile oils of Artemisia tournefortiana Reichenb. obtained by two different methods of extraction

Trends in Phytochemical Research

مقاله 1، دوره 1، شماره 2، شهریور 2017، صفحه 47-54   

نوع مقاله: Original Article

نویسندگان

Pegah Nazemizadeh Ardakani¹؛ Shiva Masoudi^{* 2}

¹Department of Medicinal Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran

²Department of Chemistry, Faculty of Science, Central Tehran Branch, Islamic Azad University, Tehran, Iran

چکیده

The essential oils obtained by hydrodistillation and solvent free microwave extraction from the aerial parts of Artemisia tournefortiana were analyzed by GC and GC/MS. Forty-six components representing 82.3% of the hydrodistilled oil and thirty-nine components representing 81.0% of the solvent free microwave extraction oil of the plant were identified. The main components of the water-distilled oils were (Z)-β- farnesene (34.2%) and nonadecane (8.1%), whereas in the microwave extraction method 2-propenoic acid, 2-ethyl hexyl ester (30.0%) and spathulenol (19.5%) were the major constituents. The water-distilled oil of Artemisia tournefortiana was rich with regard to sesquiterpenes (64.5%), whereas the solvent free microwave extraction oil was rich with regard to sesquiterpene hydrocarbons (40.0%) and non-terpenoid compounds (39.3%) and the monoterpene hydrocarbon fraction was relatively small, representing 1.7% of the total oil. According to this study, the composition of the two oils showed significant differences in the contents of the main components.

کلیدواژه‌ها

Artemisia tournefortiana؛ Essential oil؛ Gas Chromatography-Mass spectrometry (GC-MS)؛ Hydrodistillation؛ Microwave extraction

مراجع

Adams, R.P., 2007. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Allured Publishing Corporation.

Bandyukova, V., Konovalova, O., 1970. Coumarins of Artemisia chamaemelifolia. Chem. Nat. Compd. 6, 260-260.

Baytop, T., 1963. Medicinal and Poisonous Plants of Turkey. İstanbul University Publication, Turkey.

Bohlmann, F., Burkhardt, T., Zdero, C., 1973. Naturally Occurring Acetylenes. Academic Press London, United Kingdom.

Dob, T., Benabdelkader, T., 2006. Chemical composition of the essential oil of Artemisia herbaalba Asso grown in Algeria. J. Essent. Oil Res. 18, 685-690.

Firouznia, A., Akbari, M.T., Rustaiyan, A., Masoudi, S., Bigdeli, M., Anaraki, M.T., 2007. Composition of the essential oils of Artemisia turanica Krasch., Helichrysum oocephalum Boiss. and Centaurea ispahanica Boiss. three Asteraceae herbs growing wild in Iran. J. Essent. Oil-Bear. Plants 10, 88-93.

Güvenalp, Z., Çakir, A., Harmandar, M., Gleispach, H., 1998. The essential oils of Artemisia austriaca Jacq. and Artemisia spicigera C. Koch. from Turkey. Flav. Fragr. J. 13, 26-28.

Haider, F., Kumar, N., Naqvi, A.A., Bagchi, G., 2010. Oil constituents of Artemisia nilagirica var. septentrionalis growing at different altitudes. Nat. Prod. Commun. 5, 1959-1960.

Kazemi, M., Tabatabaei-Anaraki, M., Rustaiyan, A., Motevalizadeh, A., Masoudi, S., 2009. Chemical composition of the essential oils obtained from the flower, leaf and stem of Artemisia campestris L. from Iran. J. Essent. Oil Res. 21, 197-199.

Khafagy, S., Gharbo, S.A., Sarg, T., 1971. Phytochemical investigation of Artemisia herba alba. Planta Med. 20, 90-96.

Khazraei-Alizadeh, K., Rustaiyan, A., 2001. Composition of the volatile oil of Artemisia diffusa Krasch. ex Poljak. growing wild in Iran. J. Essent. Oil Res. 13, 185-186.

Kulisic, T., Radonic, A., Katalinic, V., Milos, M., 2004. Use of different methods for testing antioxidative activity of oregano essential oil. Food Chem. 85, 633-640.

Lawrence, B., 1990. Laurel Leaf oil. In: Progress in essential oils. Perfum. Flavor. 15, 67-68.

Libbey, L.M., Sturtz, G., 1989. Unusual essential oils grown in Oregon. I. Artemisia afra jacq. J. Essent. Oil Res. 1, 29-31.

Marco, J.A., Sanz-cervera, J.F., Manglano, E., Sancenon, F., Rustaiyan, A., Kardar, M., 1993a. Sesquiterpene lactones from Iranian Artemisia species. Phytochemistry 34, 1561-1564.

Marco, J.A., Sanz-Cervera, J.F., Morante, M., García-Lliso, V., Vallès-Xirau, J., Jakupovic, J., 1996. Tricyclic sesquiterpenes from Artemisia chamaemelifolia. Phytochemistry 41, 837-844.

Marco, J.A., Sanz, J.F., Sancenon, F., Rustaiyan, A., Saberi, M., 1993b. Sesquiterpene lactones from Artemisia species. Phytochemistry 32, 460-462.

Masoudi, S., Rustaiyan, A., Vahedi, M., 2012. Volatile oil constituents of different parts of Artemisia chamaemelifolia and the composition and antibacterial activity of the aerial parts of A. turcomanica from Iran. Nat. Prod. Commun. 7, 1519-1522.

Mirjalili, B.F., Meybody, M.H.H., Ardakani, M.M., Rustaiyan, A., Ameri, N., Masoudi, S., Bamoniri, A., 2006. Chemical composition of the essential oil from aerial parts, leaves, flowers and roots of Artemisia persica Boiss. from Iran. J. Essent. Oil Res. 18, 544-547.

Mohammadhosseini, M., 2017. Essential oils extracted using microwave-assisted hydrodistillation from aerial parts of eleven Artemisia species: Chemical compositions and diversities in different geographical regions of Iran. Rec. Nat. Prod. 11, 114-129.

Mohammadhosseini, M., Akbarzadeh, A., Hashemi-Moghaddam, H., Nafchi, A.M., Mashayekhi, H.A., Aryanpour, A., 2016. Chemical composition of the essential oils from the aerial parts of Artemisia sieberi by using conventional hydrodistillation and microwave assisted hydrodistillation: A comparative study. J. Essent. Oil-Bear. Plants 19, 32-45.

Mohammadpoor, S.K., Yari, M., Rustaiyan, A., Masoudi, S., 2002. Chemical constituents of the essential oil of Artemisia aucheri Boiss.-a species endemic to Iran. J. Essent. Oil Res. 14, 122-123.

Morteza-Semnani, K., Akbarzadeh, M., 2005. Essential oils composition of Iranian Artemisia absinthium L. and Artemisia scoparia Waldst. et Kit. J. Essent. Oil Res. 17, 321-322.

Mozaffarian, V., 1996. A Dictionary of Iranian Plant Names: Latin, English, Persian. Farhang Mo'aser, Tehran, Iran.

Nekoei, M., Mohammadhosseini, M., Akhlaghi, H., 2012. Chemical composition of the volatile oils from the aerial parts of Artemisia annua L.(Asteraceae) by using head space solid phase microextraction and hydrodistillation methods prior to gas chromatographic-mass spectrometric determination: A comparative investigation. J. Essent. Oil-Bear. Plants 15, 926-933.

Nematollahi, F., Rustaiyan, A., Larijani, K., Nadimi, M., Masoudi, S., 2006. Essential Oil Composition of Artemisia biennisz Willd. and Pulicaria undulata (L.) CA Mey., two Compositae herbs growing wild in Iran. J. Essent. Oil Res. 18, 339-341.

Padalia, R.C., Verma, R.S., Chauhan, A., Chanotiya, C.S., Yadav, A., 2011. Variation in the volatile constituents of Artemisia annua var. CIM-Arogya during plant ontogeny. Nat. Prod. Commun. 6, 239-242.

Rechinger, K., 1980. Artemisia. In: Flora Iranica, Compositae, No. 158. Akademische Druck and Verlagsanstalt, Graz, Austria.

Rustaiyan, A., Balalaei, S., Mohammadi, F., Masoudi, S., Yari, M., 2000a. Comparison of the volatile oils of Artemisia santolina Schrenk and Artemisia gypsacea Krasch., M. Pop. et Lincz. ex Poljak. from Iran. J. Essent. Oil Res. 12, 330-332.

Rustaiyan, A., Bamonieri, A., Raffatrad, M., Jakupovic, J., Bohlmann, F., 1987. Eudesmane derivatives and highly oxygenated monoterpenes from Iranian Artemisia species. Phytochemistry 26, 2307-2310.

Rustaiyan, A., Komeilizadeh, H., Masoudi, S., Monfared, A., Yari, M., Kardar, M., Shahgholi, A., 2000b. Composition of the volatile oil of Artemisia deserti Krasch and Artemisia oliveriana J. Gayex DC. from Iran. J. Sci. I. R. Iran 11, 213-216.

Rustaiyan, A., Masoudi, S., 2011. Chemical constituents and biological activities of Iranian Artemisia species. Phytochem. Lett. 4, 440-447.

Rustaiyan, A., Masoudi, S., Kazemi, M., 2007. Volatile oils constituents from different parts of Artemisia ciniformis Krasch. et M. Pop. ex Poljak and Artemisia incana (L.) Druce. from Iran. J. Essent. Oil Res. 19, 548-551.

Rustaiyan, A., Sigari, H., Jakupovic, J., Grenz, M., 1989a. A sesquiterpene lactone from Artemisia diffusa. Phytochemistry 28, 2723-2725.

Rustaiyan, A., Tabatabaei-Anaraki, M., Kazemi, M., Masoudi, S., Makipour, P., 2009. Chemical composition of essential oil of three Artemisia species growing wild in Iran: Artemisia kermanensis Podl., A. kopetdaghensis Krasch., M. Pop et Lincz. ex Poljak., and A. haussknechtii Boiss. J. Essent. Oil Res. 21, 410-413.

Rustaiyan, A., Zare, K., Ganj, M., Sadri, H., 1989b. A melampolide and two dihydro artemorin derivatives from Artemisia gypsacea. Phytochemistry 28, 1535-1536.

Rybalko, K., Konovalova, O., Sheichenko, V., Zakharov, P., 1976. Armin-a new coumarin from Artemisia armeniaca. Chem. Nat. Compd. 12, 262-265.

Sacco, T., Frattini, C., Bicchi, C., 1983. Constituents of essential oil of Artemisia arborescens. Planta Med. 47, 49-51.

Sanz, J.F., Marco, J.A., 1990. New eudesmane derivatives from Artemisia tournefortiana. Eur. J. Org. Chem. 1990, 541-545.

Setzer, W.N., Vogler, B., Schmidt, J.M., Leahy, J.G., Rives, R., 2004. Antimicrobial activity of Artemisia douglasiana leaf essential oil. Fitoterapia 75, 192-200.

Sharopov, F.S., Setzer, W.N., 2011. The essential oil of Artemisia scoparia from Tajikistan is dominated by phenyldiacetylenes. Nat. Prod. Commun. 6, 119-122.

Sun, Y., Li, Y.-H., Wu, X.-X., Zheng, W., Guo, Z.-H., Li, Y., Chen, T., Hua, Z.-C., Xu, Q., 2006. Ethanol extract from Artemisia vestita, a traditional Tibetan medicine, exerts anti-sepsis action through down-regulating the MAPK and NF-kappaB pathways. Int. J. Mol. Med. 17, 957.

Talzhanov, N., Rodichev, M., Raldugin, V., Gatilov, Y.V., Shakirov, M., Ivasenko, S., Turdybekov, K., Adekenov, S., 2007. Tourneforin, a novel eudesmanolide from Artemisia tournefortiana. Chem. Nat. Compd. 43, 555-557.

Trendafilova-Savkova, A.B., Todorova, M.N., Gussev, C.V., 2003. Silphiperfolane sesquiterpene acids from Artemisia chamaemelifolia Vill. l. Z. Naturforsch. C 58, 817-819.

Woerdenbag, H.J., Lugt, C.B., Pras, N., 1990. Artemisia annua L.: a source of novel antimalarial drugs. Pharm. Weekbl. 12, 169-181.

Wollenweber, E., Favre-Bonvin, H., Houl Ville, M., Rustaiyan, A., 1992. A phloracetophenone derivative and flavonoid aglycones from the lipophilic exudates of Artemisia aucheri. Phytochemistry 11, 105-107.

Zanousi, M.B.P., Nekoei, M., Mohammadhosseini, M., 2016. Composition of the essential oils and volatile fractions of Artemisia absinthium by three different extraction methods: Hydrodistillation, solvent-free microwave extraction and headspace solid-phase microextraction combined with a novel QSRR evaluation. J. Essent. Oil-Bear. Plants 19, 1561-1581.