417 0009-3130/16/5203-0417 © 2016 Springer Science+Business Media New York Chemistry of Natural Compounds, Vol. 52, No. 3, May, 2016 CHEMICAL COMPOSITION OF Artemisia aralensis S. M. Adekenov, 1* A. I. Makubaeva, 1 D. N. Kokkozov, 1 E. N. Kanafin, 1 V. S. Korneev, 1 Yu. V. Gatilov, 2,3 A. S. Kishkentaeva, 1 and G. A. Atazhanova 1 Essential oil and a CO 2 extract, the main constituent of which was geraniol, were obtained for the first time from Artemisia aralensis Krasch. The germacrane-type sesquiterpene lactone argracin was isolated for the first time from the CHCl 3 extract and studied by X-ray crystal structure analysis. Keywords: Artemisia aralensis, steam distillation, CO 2 extraction, 9-acetoxy-6,7(H)-germacra-4(5),1(10),11(13)- trien-6,12-olide, geraniol, essential oil, GC-MS, XSA, NMR, IR, HPLC. Artemisia aralensis Krasch. is an endemic species that grows in arid zones on clayey and sandy alkaline soils in the dry gullies of intermittent streams. It grows on the northern shore of the Aral Sea in the Syr Darya River bottoms. According to the literature [1], the plant has a distinct lemon aroma although the chemical composition of the essential oil has not been studied. The chemical composition of the aerial part of A. aralensis growing in Aktobe Oblast, Republic of Kazakhstan, was studied [2]. Raw material (flower heads, leaves, buds) was collected in June 2014 during budding in the vicinity of Shalkar, Aktobe Oblast, Republic of Kazakhstan. Essential oil was obtained by steam distillation from air-dried aerial part of A. aralensis. The isolation method [3] produced from raw material (100 g) essential oil as a thin yellow liquid with a pleasant citrus aroma. The yield was 0.312%; acid number 4.96; ester number 35.7; n D 0.901. CO 2 extracts of A. aralensis were also obtained on a USFE-5/2 laboratory CO 2 extractor (Russia) at pressures of 15 and 35 MPa and at 25 MPa with a co-solvent (EtOH). The CO 2 extracts of A. aralensis were light-yellow to green oils with a citrus aroma that were obtained in yields of 1.52, 6.5, and 7.41%, respectively. This raw material was extracted by liquid CO 2 for the first time. The qualitative and quantitative compositions of essential oil samples and CO 2 extracts were analyzed by GC-MS on an Agilent 7890/5975C GC with a mass-selective detector (Table 1). The chemical compositions of essential oils obtained by steam distillation and supercritical CO 2 extraction of A. aralensis were compared using GC-MS. Several compounds such as 1,8-cineol, linalool, and geraniol were present in essential oil obtained by steam distillation and CO 2 extraction. Moreover, the CO 2 extract contained constituents that were missing in the essential oil (heptadecane, octadecane, hexadecane, nonadecane, eicosane). Table 1 shows that the principal constituents of the essential oil were  3 -carene and geraniol. The principal constituents of the A. aralensis CO 2 extracts obtained at 15 and 35 MPa were geraniol and geranylacetate. The organoleptic properties and chemical composition of essential oil from A. aralensis differed sharply from those of the CO 2 extracts obtained under various conditions. The quantitative contents of the sesquiterpene lactone argracin in the CO 2 , CHCl 3 , EtOH, and aqueous extracts of A. aralensis were determined (Table 2). 1) Phytochemistry International Scientific-Production Holding Corp., Karaganda, 100009, Republic of Kazakhstan, fax: 8 (7212) 43 31 27, e-mail: phyto_pio@mail.ru; 2) N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 9 Lavrenteva Prosp., Novosibirsk, 630090, e-mail: gatilov@nioch.nsc.ru; 3) Novosibirsk State University, 2 Pirogova St., Novosibirsk, 630090. Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2016, pp. 365–368. Original article submitted September 9, 2015. DOI 10.1007/s10600-016-1662-z