DOI 10.1007/s10600-014-1120-8 Chemistry of Natural Compounds, Vol. 50, No. 5, November, 2014 [Russian original No. 5, September–October, 2014] CHEMICAL COMPOSITION OF THE ESSENTIAL OIL OF Geum rhodopeum D. L. Miladinovic,1* B. S. Ilic,1 J. S. Matejic,1 V. N. Randjelovic,2 D. M. Nikolic,3 T. M. Mihajilov-Krstev,2 and I. O. Mladenovic4 The genus Geum with ca. 60 species in the family Rosaceae is primarily found in temperate or montane regions of Europe, Asia, North and South America, Africa, and New Zealand [1]. Geum rhodopeum Stoj. & Stef. is representative of the East Moesian [moes. (E)] endemic taxa of the Balkan floristic subregion [2]. Geum species are used in traditional medicine and exhibit antiviral, anti-inflammatory, anticoagulant, antidizziness (Menierecs syndrome), angiogenesis, and myogenesis activities [3–6]. Phytochemical studies on the Geum species have revealed the occurrence of many secondary metabolites, such as terpenoids, flavonoids, tannins, and phenylpropanoids [7–10]. To the best of our knowledge, there is no report in the literature on the chemical composition of the essential oil of Geum rhodopeum Stoj. & Stef. Aerial parts of Geum rhodopeum were collected in June 2010 at Prestojceva mahala (Cemernik Mountain-42q44c45.43cc N, 22q18c40.01cc E, Elev. 1339 m). The plant material was authenticated by one of the authors (V. N. Randjelovic). A voucher specimen, with the accession number 16680, is deposited at the Herbarium of the Department of Botany, Faculty of Biology, University of Belgrade – Herbarium Code BEOU. Oil was obtained from air-dried aerial parts of the plant with 0.01% (w/w) yield by hydrodistillation for 4 h using a Clevenger-type apparatus. The oil analyses were performed simultaneously by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) systems. The GC analysis of the oils was carried out on a GC HP-5890 II apparatus equipped with a split-splitless injector, an HP-5MS capillary column (30 m u 0.25 mm, 0.25 Pm film thickness) with helium as the carrier gas (1 mL/min), and FID. Operating conditions: injector temperature 250qC and interface temperature 280qC, temperature program from 50qC (3 min) to 250qC at a rate of 3qC/min. Volume injected, 1 PL of the oil in ether (0.5%). GC/MS analyses, under the same gas-chromatograph conditions, were performed on an Agilent Technologies apparatus, Model GS 6890N coupled with a mass selective detector MSD 5975C. The MS operating parameters were as follows: ionization potential 70 eV; ion source temperature 250qC; quadrapole 150qC, solvent delay 3.0 min, mass range 50–550 amu, Em voltage 1435 V. Identification of the compounds was based on comparison of Kovats retention indexes (applying calibrated automated mass spectral deconvolution and identification system software (AMDIS ver. 2.64) in combination with selective ion analysis (SIA) resolution method [11]), comparison with the spectral data from the available literature [12], and comparison of their mass spectra to those from Wiley 275 and NIST/NBS libraries using various search engines. Relative retention indexes (RRI) were obtained by co-injection with an aliphatic C7–C40 hydrocarbon standard mixture. The results of GC and GC/MS analyses of the investigated oil are summarized in Table 1. Sixty-four compounds were identified, representing 91.0% of the total oil. The major component was D-bisabolol, constituting 12.7% of the oil. 1) Department of Pharmacy, Faculty of Medicine, University of Nis, Bul. Dr Zorana Djindjica 81, 18000 Nis, Serbia, fax: +381 18 4238770, e-mail: dragoljubm@gmail.com; 2) Department of Biology and Ecology, Faculty of Science and Mathematics, University of Nis, Visegradska 33, 18000 Nis, Serbia; 3) Department of Sanitary Chemistry, Institute of Public Health, Bul. Dr Zorana Djindjica 50, 18000 Nis, Serbia; 4) Institute of Chemistry, Technology, and Metallurgy-ICTM-MTSC, University of Belgrade, Njegoseva 12, 11000, Belgrade. Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2014, pp. 800–801. Original article submitted January 29, 2013. 926 0009-3130/14/5005-0926 ”2014 Springer Science+Business Media New York TABLE 1. Composition of the Essential Oil from Aerial Parts of Geum rhodopeum Compound RRI Content, % trans-2-Hexenal cis-3-Hexenol Benzaldehyde 1-Octen-3-ol 3-Octanol Octanal o-Cymene Benzene acetaldehyde 1-Octanol Linalool Nonanal Fenchol 6,6-Dimethylbicyclo[3.1.1]heptan-2-one Nonalol 4-Terpineol Myrtanal Methyl salicylate Myrtenal Safranal Decanal Fenchyl acetate E-Citronellol 7-Methylenebicyclo[3.3.1]nonan-3-ol Cuminal Carvotanacetone cis-Myrtanol Perillaldehyde Phellandral Undecanal E-Damascenone Tetradecane 1,7-Dimethylnaphthalene E-Caryophyllene 2,6-Dimethylnaphthalene 850 852 960 980 997 1003 1024 1043 1070 1099 1105 1119 1138 1172 1181 1185 1191 1196 1199 1206 1218 1226 1241 1242 1249 1264 1276 1278 1308 1378 1400 1417 1419 1421 0.1 0.2 0.2 5.3 0.9 0.3 0.2 0.7 0.3 1.9 0.9 0.4 0.6 0.4 0.2 5.8 0.6 9.5 0.5 0.2 3.8 0.5 0.5 0.2 1.4 1.3 0.6 2.2 0.4 1.1 0.2 0.2 0.2 0.2 Compound E -Cedrene D-Bergamotene Geranyl acetone D-Humulene Alloaromadendrene E -Ionene D-Curcumene D-Muurolene D-Bisabolene Tridecanal Lauric acid Caryophyllene oxide Hexadecane Ledol D-Bisabolol oxide B D-Bisabolol 1-Isopropyl-4,8-dimethyl spiro[4.5]dec-8-en-7-one Tetradecanal Myristic acid Phenanthrene Hexahydrofarnesyl acetone Diisobutyl phthalate (5E,9E)-6,10,14-Trimethyl-5,9,13pentadecatrien-2-one Methyl palmitate Isophytol Dibutyl phthalate Palmitic acid Phytol Oleic acid Dioctyl phthalate Total identified RRI Content, % 1424 1433 1447 1455 1459 1478 1480 1498 1507 1511 1563 1582 1600 1604 1655 1687 1688 0.3 0.3 0.4 0.2 0.6 1.2 0.3 0.2 0.2 0.6 0.5 0.7 0.3 1.4 0.5 12.7 7.7 1715 1759 1778 1841 1857 1908 0.5 0.3 0.4 4.0 2.6 0.2 1924 1945 1951 1965 2108 2135 2525 0.3 0.3 1.3 6.4 3.6 0.2 0.8 91.0 Significant compounds were myrtenal (9.5%), 1-isopropyl-4,8-dimethylspiro[4.5]dec-8-en-7-one (7.7%), palmitic acid (6.4%), myrtanal (5.8%), and 1-octen-3-ol (5.3%), while the other constituents were present in less than 5%. The essential oil of the aerial part of the Geum iranicum Khatamaz had palmitic acid (10.6%) and linoleic acid (9.6%) as the main constituents [13]. The major compounds in the oil of the roots and rhizomes of Geum kokanicum were eugenol (80.9%) and myrtenol (5.2%) [14]. ACKNOWLEDGMENT The authors are grateful to the Ministry of Education and Science of Serbia (Projects Nos. 171025 and 173030) for financial support. REFERENCES 1. 2. 3. J. E. E. Smedmark and T. Eriksson, Syst. Bot., 27, 303 (2002). V. N. Randjelovic, B. K. Zlatkovic, V. N. Milosavljevic, and N. V. Randjelovic, Phytol. Balcan., 14, 367 (2008). T. Liu, J. F. Wang, Z. Q. Liu, L. C. Zhang, G. L. Shang, J. X. Yang, and Y. Lai, J. Dali Univ., 5, 4 (2006). 927 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 928 W. Deng and Z. C. Li, Guizhou Med. J., 30, 1126 (2006). Y. M. Xu and L. S. Dong, J. Guiyang College Trad. Chin. Med., 14, 58 (1992). M. Li, C. M. Yu, L. Cheng, M. Wang, X. Gu, K. H. Lee, T. Wang, Y. T. Sung, and J. E. Sanderson, Clin. Chem., 52, 1460 (2006). Y. Q. Gao, E. Y. Wang, D. G. Zhao, J. H. Liu, and Y. Liu, Biotechnol., 15, 52 (2005). X. R. Cheng, H. Z. Jin, J. J. Qin, J. J. Fu, and W. D. Zhang, Chem. Biodivers., 8, 203 (2011). J. K. Li, H. W. Liu, N. L. Wang, M. Li, and X. S. Yao, J. Shenyang Pharm. Univ., 23, 694 (2006). L. Panizzi, S. Catalano, C. Miarelli, P. L. Cioni, and E. Campeol, Phytother. Res., 14, 561 (2000). B. Tan, Y. Liang, L. Yi, H. Li, Z. Zhou, X. Ji, and J. Deng, Metabolomics, 6, 219 (2010). R. P. Adams, Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, Allured Publishing Corporation, Carol Stream, 2007. S. Shahani, H. R. Monsef-Esfahani, R. Hajiaghaee, and A. R. Gohari, J. Essent. Oil Res., 23, 29 (2011). M. A. Faramarzi, M. Moghimi, H. R. Monsef-Esfahani, A. R. Shahverdi, and S. Khodaee, Chem. Nat. Compd., 44, 811 (2008).