Journal of Essential Oil Bearing

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Essential Oil Composition of stenolepis Kerner. from Turkey

Kaan Polatoglu, Ali Sen, Gizem Bulut, Leyla Bitis & Nezhun Gören

To cite this article: Kaan Polatoglu, Ali Sen, Gizem Bulut, Leyla Bitis & Nezhun Gören (2014) Essential Oil Composition of Centaurea￿stenolepis Kerner. from Turkey, Journal of Essential Oil Bearing Plants, 17:6, 1268-1278, DOI: 10.1080/0972060X.2014.935090 To link to this article: https://doi.org/10.1080/0972060X.2014.935090

Published online: 23 Feb 2015.

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Full Terms & Conditions of access and use can be found at https://www.tandfonline.com/action/journalInformation?journalCode=teop20 TEOP 17 (6) 2014 pp 1268 - 1278 1268 ISSN Print: 0972-060X ISSN Online: 0976-5026

Essential Oil Composition of Centaurea stenolepis Kerner. from Turkey

Kaan Polatoglu 1,4 *Ali Sen 2, Gizem Bulut 3, Leyla Bitis 2, Nezhun Gören 4

1 Department of Analytical Chemistry, Faculty of Pharmacy, 34217, Istanbul Kemerburgaz University, Istanbul, Turkey. 2 Department of Pharmacognosy, Faculty of Pharmacy, 34668, Marmara University, Istanbul, Turkey 3 Department of Pharmaceutical Botany, Faculty of Pharmacy, 34668, Marmara University, Istanbul, Turkey 4 Department of Biology and Genetics, Faculty of Science and Letters, 34210, Yildiz Technical University, Istanbul, Turkey Received 06 June 2013; accepted in revised form 25 December 2013

Abstract: Essential oil composition of Centaurea stenolepis Kerner flowers and stems were investigated with GC, GC-MS. Flowers and stems of C. stenolepis had very low essential oil yield <0.01 % (v/w). Twenty eight compounds were identified in the flower oil which represent 53.5 % of the oil. Main components of the flower oil include caryophyllene oxide 12.6 %, hexadecanoic acid 10.6 % and β-Eudesmol 7.2 %. Forty compounds were identified in the stem oils which represent 74.2 % of the oil. Main components of the stem oils include hexadecanoic acid 38.4 % and phytol 12.9 %. Both flower and stem oils were rich on oxygenated sesquiterpene hydrocarbons and fatty acids.

Key words: , Centaurea, Essential Oil, Hexadecanoic acid, Phytol, β-Eudesmol, Caryophyllene oxide. Introduction 6,7, sesquiterpene lactones (guaianolides, germa- Genus Centaurea L. (Astereceae) represented cronolides) 7-12, triterpenes 7 and alkaloids 13 from with more than 170 species in Turkey with a very Centaurea species. Previous reports on the high rate of endemism 1,2. Centaurea species are essential oil composition of Centaurea species well known with local names “devedikeni”, indicate main components as caryophyllene 14,15, “peygamber çiçegi”, “zerdali dikeni”, “çoban spathulenol 16,17, eudesmol 17-19, germacrene 16,20- kaldiran” and “Timur dikeni” in Turkey3. Many 24 as sesquiterpenes; hexadecanoic acid 5,18,25-35, folk medicinal uses of Centaurea species were tetradecanoic acid 29, dodecanoic acid 26,29,33 as reported, these uses include; wound healing, fatty acids; heptacosane 5,17,22,25,31,35,36, tricosane antidiabetic, antidiarrhetic, antirheumatic, anti- 22,31,35, pentacosane 22, nonacosane 5 as higher inflammatory, colagog, choleretic, digestive, alkanes and pinenes 16, terpinenes 16, carvacrol 29 stomachic, diuretic, menstrual, astringent, as monoterpenes. Until now 42 taxa of Centaurea hypotensive, antipyretic, cytotoxic, antibacterial were investigated for essential oil composition purposes3-5. from Turkey; main components of these oils were Previous reports indicate isolation of flavonoids given in Table 1. A previous investigation on

*Corresponding author (Kaan Polatoglu) E-mail: < [email protected] > © 2014, Har Krishan Bhalla & Sons Kaan Polatoglu et al., / TEOP 17 (6) 2014 1268 - 1278 1269 Centaurea stenolepis from Romania reports main guiacol (4.3 - 5.0 %) 17. essential oil components as caryophyllene oxide To the best of our knowledge this is the first (6.9 - 15.6 %), hexahydrofarnesyl acetone (6.5 - report on essential oil composition of Centaurea 4.4 %), heptacosane (6.0 - 4.9 %) and p-vinyl- stenolepis from Turkey.

Table 1. Essential oil composition of previously investigated Centaurea species from Turkey

Plant name Main Components of Essential Oil Amount %

C.aladaghensis 28 Caryophyllene oxide 6.6 Hexadecanoic acid 39.3 C. aladaghensis 23 β-Eudesmol 11.8 Caryophyllene oxide 7.5 Germacrene D 22.7 β-Caryophyllene 18.3 C. amanicola 34 4-Vinyl guaiacol 9.4 Caryophyllene 5.4 Caryophyllene oxide 12.0 Hexahydrofarnesyl acetone 6.0 Hexadecanoic acid 15.0 (Z,Z)-9,12 Octadecanoic acid 5.7 C. antiochia var. praealta 23 α-Bisabolol 5.3 Bicyclogermacrene 5.5 Germacrene D 45.1 C. antitauri 23 Bicyclogermacrene 5.0 Germacrene D 40.2 β-Caryophyllene 13.5 C. appendicigera 14 β-Caryophyllene 17.5 δ-Gurjunene 7.6 Caryophyllene oxide 17.1 C. armena 19 Calarene 10.3 β-Eudesmol 19.3 6,10,14-Trimethyl-2-pentadecanone 5.7 C. babylonica 23 Germacrene D 43.0 β-Caryophyllene 9.9 Heptanol acetate 7.1 p-Cymene 6.1 C. balsamita 23 Germacrene D 40.2 Bicyclogermacrene 7.1 C. cadmea 29 Carvacrol 14.7 - 16.6 Dodecanoic acid 4.4 - 5.3 Phytol 41.0 - 6.0 Hexadecanoic acid 23.1 - 19.5 C. calolepis 29 Carvacrol 18.9 Hexadecanoic acid 27.3 C. cariensis subsp. maculiceps 29 4-Methyl-4-hepten-3-one 12.8 Carvacrol 13.0 Hexadecanoic acid 4.9 Kaan Polatoglu et al., / TEOP 17 (6) 2014 1268 - 1278 1270

table 1. (continued).

Plant name Main Components of Essential Oil Amount %

C. cariensis subsp. microlepis 29 Carvacrol 28.4 Hexadecanoic acid 10.0 C. cheirolepidoides 23 Germacrene D 21.7 Caryophyllene oxide 6.1 β-Caryophyllene 14.4 β-Cedrene 5.1 C. chrysantha 20 Germacrene D 27.4 Bicyclogermacrene 5.4 Caryophyllene oxide 9.5 C. consanguinea 34 Guaiacol 14.9 Germacrene B 8.3 Caryophyllene oxide 7.3 Hexahydro farnesyl acetone 13.5 Hexadecanoic acid 14.2 (Z,Z)-9,12 Octadecanoic acid 5.7 C. 29 Carvacrol 25.5 Hexadecanoic acid 6.4 C. deflexa 23 Germacrene D 21.2 Caryophyllene oxide 12.8 β-Caryophyllene 33.9 C. depressa 29 Carvacrol 14.2 Tetradecanoic acid 8.8 Hexadecanoic acid 21.3 C. dichroa 37 Caryophyllene oxide 9.8 Spathulenol 5.8 Hexadecanoic acid 11.8 C. ensiformis 29 Carvacrol 17.4 Phytol 6.0 Hexadecanoic acid 13.2 C. ensiformis 39 β-Eudesmol 29.8 Hexadecanoic acid 8.0 Caryophyllene oxide 7.6 C. hadimensis 21 β-Caryophyllene 9.8 Germacrene D 44.3 Bicyclogermacrene 7.9 C. helenioides 14 Germacrene D 7.3 Caryophyllene oxide 18.2 cis-Phytol 6.2 C. hierapolitana 29 Carvacrol 13.3 Hexadecanoic acid 33.4 C. huber-morathii 38 Octanol 17.8 Hexadecanoic acid 8.0 C. iconiensis 23 1-Undecene 84.3 C. kotschyi var. decumbens 24 β-Caryophyllene 11.2 Kaan Polatoglu et al., / TEOP 17 (6) 2014 1268 - 1278 1271 table 1. (continued).

Plant name Main Components of Essential Oil Amount %

β-Cedrene 7.1 Germacrene D 29.4 C. kotschyi var. kotschyi 24 β-Caryophyllene 12.1 Germacrene D 44.2 Bicyclogermacrene 5.5 C. lanigera 23 Bicyclogermacrene 6.7 Germacrene D 43.1 β-Caryophyllene 13.7 C. luschaniana 5 Nonacosane 7.8 Dodecanoic acid 12.6 Hexadecanoic acid 40.0 C. mucronifera 20 β-Caryophyllene 7.3 Germacrene D 29.3 Caryophyllene oxide 5.2 β-Eudesmol 17.4 C. paphlagonica 33 Hexadecanoic acid 28.9 Dodecanoic acid 22.8 Caryophyllene oxide 9.2 C. pseudoscabiosa subsp. β-Caryophyllene 8.1 pseudoscabiosa 21 Germacrene D 36.0 β-Sesquiphellandrene 8.5 C. ptosimopappa 34 p-Cymen-8-ol 7.6 p-Methoxyacetophenone 6.8 β-Eudesmol 8.2 Hexadecanoic acid 13.6 (Z,Z)-9,12 Octadecanoic acid 6.1 C. ptosimopappoides 23 α-Eudesmol 9.1 Germacrene D 36.9 β-Caryophyllene 22.5 C. reuterana 29 Caryophyllene oxide 6.2 Carvacrol 14.9 Hexadecanoic acid 23.8 C. saligna 25 Phytol 8.2 Heptacosane 5.2 Hexadecanoic acid 41.9 C. sericea 39 Caryophyllene oxide 10.6 Nonacosane 8.6 Hexadecanoic acid 7.0 C. sessilis 19 Caryophyllene oxide 10.0 β-Eudesmol 12.4 cis-Phytol 6.4 C. tchihatcheffii 40 Caryophyllene oxide 15.1 Carvacrol 14.7 Kaan Polatoglu et al., / TEOP 17 (6) 2014 1268 - 1278 1272 table 1. (continued).

Plant name Main Components of Essential Oil Amount %

Acetophenone 6.2 Spathulenol 5.3 C. tossiensis 5 Pentacosane 5.8 Heptacosane 10.7 Nonacosane 11.6 Hexadecanoic acid 25.6 C. urvillei subsp. urvillei 29 Carvacrol 12.4 Dodecanoic acid 9.4 Hexadecanoic acid 26.4 C. wagenitzii 5 Caryophyllene oxide 7.3 Heptacosane 9.8 Nonacosane 12.0 Hexadecanoic acid 25.6

Materials and methods set at 250°C. Split ratio was set to 50:1. Innowax Plant material FSC column (60 m x 0.25 mm, 0.25 μm film Plant material was collected during the thickness) and helium as carrier gas (1 mL/min) flowering period in july 2009 from Istanbul - was used both in GC and GC-MS analysis. Oven Çatalça. Voucher specimens have been deposited temperature was programmed to 60°C for 10 min. at the Herbarium of the Faculty of Pharmacy, and raised to 220°C at rate of 4°C/min. Marmara University (Voucher no. MARE 11651), Temperature kept constant at 220°C for 10 min. Turkey. Plant materials were identified by Dr. and then raised to 240°C at a rate of 1°C/min. Gizem BULUT. Mass spectra were recorded at 70 eV with the mass range m/z 35 to 425. FID detector tempera- Essential oil isolation ture was set to 250°C. Relative percentage Flowers and stems (100 g each) of the plant amounts of the separated compounds were sample C. stenolepis from Istanbul - Çatalça calculated from integration of the peaks in FID location was subjected to hydro-distillation for 4 chromatograms. h using a Clevenger- type apparatus to produce Identification of essential oil components were the oils. Essential oil yields obtained from flowers carried out by comparison of their retention times and stem of C. stenolepis were <0.01 (v/w). Oils and mass spectra with authentic samples. Also were trapped in n-hexane and kept in amber by comparison of their relative retention indices bottles at -20°C until the analysis. (RRI) obtained by series of n-alkanes to the literature 5,29,37,41-49 and mass spectra comparison. Gas chromatography-Mass spectrometry Mass spectra comparison was done by computer The GC-MS analyses were performed with an matching with commercial Wiley 8th Ed./NIST Agilent 5975C Inert XL EI/CI MSD system 05 Mass Spectra library, Adams Essential Oil operating in EI mode. The GC analyses were done Mass Spectral Library, Pallisade 600K Complete with an Agilent 7890A GC system with same Mass Spectra Library and in-house Library built operational conditions employed in GC-MS by components of known oils was used for analysis. Essential oil samples were diluted 1/10 identification 43-45,47,48. (v/v) with n-hexane, simultaneous auto injection was done to obtain the same retention times. Results and Discussion Injector and MS transfer line temperatures were Essential oil composition of C. stenolepis Kaan Polatoglu et al., / TEOP 17 (6) 2014 1268 - 1278 1273 flower and stem oils were investigated with GC, of the essential oils of C. aladaghensis could be GC-MS; identified components of the oils were clearly seen in two different articles, reported by given in Table 2. Twenty eight compounds were different authors 23,28. These reports indicate that identified for the flower oil which represented C. aladaghensis oil which was collected from 53.5 % of the oil. Main components of the flower Nigde-Aladaglar region is mainly composed of oil were caryophyllene oxide (12.6 %), β- hexadecanoic acid (39.3 %), caryophyllene oxide eudesmol (7.2 %) and hexadecanoic acid (10.6 (6.6 %) 28 and β-eudesmol (11.8 %), germacrene %). Flower oil of C. stenolepis oil was mainly D (22.7 %), caryophyllene oxide (7.5 %), β- dominated with oxygenated sesquiterpenes,fatty caryophyllene (18.3 %) 23. One of the reports acids and higher alkanes. presented oil that was rich in fatty acids 28 and Forty compounds were identified in the stem the other report indicates an oil rich in sesqui- oil which represented 74.2 % of the oil. Main terpene type hydrocarbons 23. This differentiation components of the stem oil include phytol (12.9 could suggest a chemotype variation in C. %) and hexadecanoic acid (38.4 %). Stem oil of aladaghensis, since these different main compo- C. stenolepis oil was mainly dominated with fatty nents have different biosynthetic origins. Similar acids and higher alkanes. situation was also reported for C. ensiformis in Previous reports on the essential oil compo- two different articles that indicate different sition of Centaurea species did not indicate any essential oil compositions 29,39. One of the reports chemotype variation in this genus. However there indicate main essential oil components as is couple of independent reports on essential oil carvacrol (17.4 %), phytol (6.0 %), hexadecanoic compositions of the Centaurea species that were acid (13.2 %) 29 and the other one reports as β- reporting different oil composition for the same eudesmol (29.8 %), caryophyllene oxide (7.6 %) species. Serious variation in the main components and hexadecanoic acid (8.0 %) 39. These two Table 2. Flower and stem essential oil composition of Centaurea stenolepis Kerner from Turkey

No. RIa RI Compound Flower Stem Identification Lit.b Oilc Oilc Methodd

1 1212 1213 1.8-Cineole tri -RIe. MSf 2 1239 1244 2-Pentyl furan 0.6 0.2 RI. MS 3 1294 1296 Octanal - tr RI. MS 4 1399 1400 Nonanal tr 0.3 RI. MS 5 1500 1500 Pentadecanone tr - MS 6 1504 1497 α-Copaene tr - RI.MS 7 1505 1506 Decanal tr 0.1 RI.MS 8 1560 1562 Octanol - 0.1 RI.MS 9 1600 1600 Hexadecane tr tr MS. Acg 10 1608 1612 β-Caryophyllene 0.7 0.4 RI. MS 11 1693 1687 α-Humulene - 0.1 RI. MS 12 1700 1700 Heptadecane tr 0.1 MS. Ac 13 1723 1726 Germacrene D 0.9 2.5 RI. MS 14 1734 1661 Alloaromadendrene 0.3 - MS 15 1735 1740 Valencene - tr RI. MS 16 1748 1755 Bicyclogermacrene - 0.2 RI. MS 17 1800 1827 (E.E)-2.4-Decadienal - 0.2 RI. MS 18 1823 1838 (E)-α-Damascenone - 0.7 RI. MS 19 1864 1868 (E)-Geranyl acetone - 0.6 RI. MS 20 1900 1900 Nonadecane - tr MS. Ac Kaan Polatoglu et al., / TEOP 17 (6) 2014 1268 - 1278 1274 table 2. (continued).

No. RIa RI Compound Flower Stem Identification Lit.b Oilc Oilc Methodd

21 1940 1945 1.5-Epoxy salvial-4.(14)-ene 1.5 0.2 RI. MS 22 1954 1958 (E)-α-Ionone 0.5 0.9 RI. MS 23 2007 2008 Caryophyllene oxide 12.6 1.6 RI. MS 24 2031 2037 Salvial-4(14)-en-1-one 2.2 0.4 RI. MS 25 2036 2135 Hexadecanal - 0.3 MS 26 2063 2071 Humulene epoxide II 1.3 0.3 RI. MS 27 2100 2100 Heneicosane 0.3 0.2 RI. MS 28 2131 2131 Hexahydrofarnesyl acetone 2.4 1.5 RI. MS 29 2142 2144 Spathulenol 2.3 0.5 RI. MS 30 2150 2179 Nor-copaanone 0.9 0.2 RI. MS 31 2200 2200 Docosane - 0.1 MS. Ac 32 2239 2185 γ-Eudesmol 0.7 - MS 33 2253 2257 β-Eudesmol 7.2 0.8 RI. MS 34 2282 2298 Decanoic acid - 0.3 RI. MS 35 2300 2300 Tricosane 1.7 0.4 MS. Ac 36 2381 2384 Farnesyl acetone - 1.3 RI. MS 37 2400 2400 Tetracosane - 0.5 MS. Ac 38 2492 2503 Dodecanoic acid tr tr RI. MS 39 2500 2500 Pentacosane 2.5 1.1 MS. Ac 40 2614 2622 Phytol 2.5 12.9 RI. MS 41 2700 2700 Heptacosane 1.8 1.9 MS. Ac 42 2704 2670 Tetradecanoic acid - 2.4 RI. MS 43 2809 2822 Pentadecanoic acid - 1.4 RI. MS 44 2900 2900 Nonacosane - 1.1 MS. Ac 45 2917 2931 Hexadecanoic acid 10.6 38.4 RI. MS Monoterpene Hydrocarbons 0 0 Oxygenated Monoterpene 0.5 2.2 Hydrocarbons Sesquiterpene Hydrocarbons 1.9 3.2 Oxygenated Sesquiterpene 31.1 6.8 Hydrocarbons Others 20.0 62.0 Total 53.5 74.2

a Relative Retention Indices on FSC-Innowax Column (60 m x 0.25 mm. 0.25 μm film thickness) with a custom temperature program and Helium as carrier gas at 1 mL/min flow rate b Relative Retention Indices on FSC-Innowax Column with same temperature program and flow rate reported in the literature 5.29.37.41-49 c Relative percentage amounts of the separated compounds were calculated from integration of the peaks in FID chromatogram d Methods used for identification of the compound e RI: Relative retention index match with literature f MS: Mass spectra match (match e” 90 %). g Ac: Retention time and mass spectra match with authentic compound i tr : Trace amount ( < 0.1% ) Kaan Polatoglu et al., / TEOP 17 (6) 2014 1268 - 1278 1275 reports also suggest possibility of a chemotype species essential oil, non-volatile secondary variation in C. ensiformis. metabolite comparisons on samples of C. In our study with the essential oil composition stenolepis from different locations should be done of C. stenolepis, we have obtained oils from together with DNA comparisons and seasonal flowers and stems of the plant that have main variation studies. components different from the previous report on Previous studies on Centaurea species reports the essential oil composition of this plant 17. This systematical classification problems of this genus. report indicates main components of the essential In order to determine the exact systematic oils from two samples of C. stenolepis from separation patterns between taxa of this genus and Romania as caryophyllene oxide (6,9 - 15.6 %), also determine possible chemotypes, a systematic hexahydrofarnesyl acetone (6.5 - 4.4 %), study on the secondary metabolite profiles of heptacosane (6.0 - 4.9 %) and p-vinyl guiacol (4.3 Centaurea species is required. Until now nearly - 5.0 %) 17. The present study shows that flower 23 % of the Centaurea taxa were investigated for oil of C. stenolepis from Turkey is rich in their essential oil composition in Turkey. In order sesquiterpene hydrocarbons, hexadecanoic acid to contribute to the knowledge on the secondary and stem oil is rich in higher alkanes, fatty acids metabolite profiles of this genus essential oil unlike the previous report. These differences composition of Centaurea stenolepis Kerner from observed in both studies could be related to Turkey was investigated and differences were differences in collection time, ecological factors, pointed out with a previous report on the same climatic conditions, soil conditions, methods species from Romania. employed in the analysis and genetic differences. However differences in the biosynthetic origins Acknowledgment of the main compounds in both studies strongly This research was supported by State Planning suggest chemotype variation in this species exist. Organization (Project No. 27-DPT-01-07-01). In order to determine the exact situation in this

References 1. Davis, P.H. (1975). Flora of Turkey and the East Aegean Islands, Vol.5. Edinburgh University Press: Edinburgh. 2. Davis, P.H., Mill, R.R., Tan, K. (1988). In: Flora of Turkey and the East Aegean Islands Davis, P.H. Ed., Vol. 10, (Supplement I) Edinburgh University Press: Edinburgh. 3. Arif, R., Küpeli, E., Ergun, F. (2004). The biological activity of Centaurea L. species (Review). G.U. Journal of Science. 17(4): 149-164. 4. Yesilada, E., Sezik, E., Honda, G., Takaishi, Y., Takeda, Y., Tanaka, T. (1999). Traditional Medicine in Turkey IX: Folk Medicine in Northwest Anatolia. J. Ethnopharmacol. 64: 195-210. 5. Demirci, B., Kose, Y.B., Baser, K.H.C., Yucel, E. (2008). Composition of the Essential Oil of Three Endemic Centaurea Species From Turkey. J. Essent. Oil Res. 20: 335-338. 6. Flamini, G., Pardini, M., Morelli, I., Ertugrul, K., Dural, H., Bagci, Y., Kargioglu, M. (2002). Flavonoid glycosides from Centaurea pseudoscabiosa subsp. pseudoscabiosa from Turkey. Phytochemistry. 61: 433-437. 7. Flamini, G., Stoppelli, G., Morelli, I., Ertugrul, K., Dural, H., Tugay, O., Demirelma, H., (2004). Secondary metabolites from Centaurea isaurica from Turkey and their chemotaxonomical significance. Biochem. Syst. Ecol. 32: 533-557. 8. Massiot, G., Morfaux, A.M., Olivier, L.M., Bouquant, J., Madaci, A., Mahamoud, A., Chop- ova, M., Aclinou, P. (1985). Guaianolides from the of Centaurea incana. Phytochemistry. 25: 258-261. 9. Appendino, G., Gariboldi, P., Belliardo, F. (1986). Sesquiterpene lactones from Centaurea uniflora subsp. nervosa. Phytochemistry. 25: 2163-2165. Kaan Polatoglu et al., / TEOP 17 (6) 2014 1268 - 1278 1276 10. Oksuz, S., Serin, S., Topcu, G. (1994). Sesquiterpene lactones from Centaurea hermannii. Phyto- chemistry. 35: 435-438. 11. Youssef, D., Frahm, A.W. (1996). Circular dichroism of C-7, C-6 trans-fused guaianolides of Centaurea scoparia. Phytochemistry. 41: 1107-1111. 12. Oksuz, S., Putun, E. (1983). Guaianolides from Centaurea kotschyi. Phytochemistry. 22: 2615- 2616. 13. Sarker, S.D., Laird, A., Nahar, L., Kumarasamy, Y., Jaspars, M. (2001). Indole alkaloids from the seeds of (Asteraceae). Phytochemistry. 57: 1273-1276. 14. Yayli, N., Yasar, A., Yayli, N., Albay, C., Asamaz, Y., Coþkunçelebi, K., Karaoðlu, S. (2009). Chemical composition and antimicrobial activity of essential oils from Centaurea appendicigera and Centaurea helenioides. Pharm. Biol. 47 1: 7-12. 15. Dob, T., Dahmane, D., Gauriat-Desrdy, B., Daligault, V. (2009). Essential Oil Composition of Centaurea pullata L. J. Essent. Oil Res. 21: 417-422. 16. Salmanpour, S., Khalilzadeh, M.A., Sadeghifar, H. (2009). Chemical Composition of the Essential Oils From Leaves, Flowers, Stem and Root of Centaurea zuvandica Sosn. J. Essent. Oil Res. 21: 357-359. 17. Formisano, C., Senatore, F., Bancheva, S., Bruno, M., Maggio, A., Rosselli, S. (2010). Volatile Components of Aerial Parts of Centaurea nigrescens and C. stenolepis Growing Wild in the Balkans. Nat. Prod. Commun. 5, 2: 273-278. 18. Rosselli, S., Bruno, M., Maggio, A., Raccuglia, A.R., Bancheva, S., Senatore, F., Formisano, C. (2009). Essential oils from the aerial parts of Centaurea cuneifolia Sibth. & Sm. and C. euxina Velen., two species growing wild in Bulgaria. Biochem. Syst. Ecol., 37: 426-431. 19. Yayli, N., Yasar, A., Güleç, C., Usta, A., Kolayli, S., Coskunçelebi, K., Karaoglu, S. (2005). Composition and antimicrobial activity of essential oils from Centaurea sessilis and Centaurea armena. Phytochemistry. 66: 1741-1745. 20. Dural, H., Bagci, Y., Ertugrul, K., Demirelma, H., Flamini, G, Cioni, P.L., Morelli, I. (2003). Essential oil composition of two endemic Centaurea species from Turkey, Centaurea mucronifera and Centaurea chrysantha, collected in the same habitat. Biochem. Syst. Ecol. 31: 1417-1425. 21. Flamini, G., Ertugrul, K., Cioni, P.L., Morelli, I., Dural, H., Bagci, Y. (2002). Volatile consti- tuents of two endemic Centaurea species from Turkey: C. pseudoscabiosa subsp. pseudoscabiosa and C. hadimensis. Biochem. Syst. Ecol. 30: 953-959. 22. Senatore, F., Rigano, D., De Fusco, R., Bruno, M. (2003). Volatile components of Centaurea cineraria L. subsp. umbrosa (Lacaita) Pign. and Centaurea napifolia L. (Asteraceae), two species growing wild in Sicily. Flavour Fragr. J. 18: 248-251. 23. Flamini, G., Tebano, M., Cioni, P.L., Bagci, Y., Dural, H., Ertugrul, K., Uysal, T., Savran, A. (2006). A multivariate statistical approach to Centaurea classification using essential oil com- position data of some species from Turkey. Pl. Syst. Evol. 261: 217-228. 24. Ertugrul, K., Dural, H., Tugay, O., Flamini, G., Cioni, P.L., Morelli, I. (2003). Essential oils from flowers of Centaurea kotschyi var. kotschyi and C. kotschyi var. decumbens from Turkey. Flavour Fragr. J. 18: 95-97. 25. Altintas, A., Kose, Y.B. Kandemir, A., Demirci, B., Baser, K.H.C. (2009). composition of the essential oil of Centaurea saligna. Chem. Nat. Compd. 45, 2: 276-277. 26. Senatore, F., Apostolides, Arnold, N.A., Bruno, M. (2005). Volatile components of Centaurea eryngioides Lam. and Centaurea iberica Trev. var. hermonis Boiss. Lam., two Asteraceae growing wild in Lebanon. Nat. Prod. Res. 19, 8: 749-754. 27. Formisano, C., Mignola, E., Senatore, F., Bancheva, S., Bruno, M., Rosselli, S. (2008). Volatile constituents of aerial parts of Centaurea sibthorpii (Sect. Carduiformes, Asteraceae) from Greece and their biological activity. Nat. Prod. Res. 22, 10: 840-845. Kaan Polatoglu et al., / TEOP 17 (6) 2014 1268 - 1278 1277 28. Köse, Y.B., Iscan, G., Demirci, B., Baser, K.H.C., Çelik, S. (2007). Antimicrobial activity of the essential oil of Centaurea aladagensis. Fitoterapia. 78, 253-254. 29. Karamenderes, C., Demirci., B., Baser., K.H.C. (2008). Composition of Essential Oils of Ten Centaurea L. Taxa from Turkey. J. Essent. Oil Res. 20: 342-349. 30. Firouznia, A., Akbari, M.T., Rustaiyan, A., Masoudi, S., Bigdeli, M., Tabatabaei-Anaraki, M. (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 Bearing Plants. 10, 2: 88-93. 31. Senatore, F., Formisano, C., Raio, A., Bellone, G., Bruno, M. (2008). Volatile components from flower-heads of Centaurea nicaeensis All., C. parlatoris Helder and C. solstitialis L. ssp. schouwii (DC.) Dostál growing wild in southern Italy and their biological activity. Nat. Prod. Res. 22, 10: 825-832. 32. Esmaeili, A., Rustaiyan, A., Akbari, M.T., Moazami, N., Masoudi, S., Amiri, H. (2006). Composition of the Essential Oils of Xanthium strumarium L. and Centaurea solstitialis L. from Iran. J. Essent. Oil Res. 18: 427-429. 33. Kose, Y.B., Altintas, A., Demirci, B., Celik, S., Baser, K.H.C. (2009). Composition of the Essential Oil of Endemic Centaurea paphlagonica (Bornm.) Wagenitz From Turkey. Asian J. Chem. 21, 3: 1719-1724. 34. Formisano, C., Rigano, D., Senatore, F., Çelik, S., Bruno, M., Rosselli, S. (2008). Volatile constituents of aerial parts of three endemic Centaurea species from Turkey: Centaurea amanicola Hub.-Mor., Centaurea consanguinea DC. and Centaurea ptosimopappa Hayek and their anti- bacterial activities. Nat. Prod. Res. 22, 10: 833-839. 35. Senatore, F., Landolfi, S., Celik, S., Bruno, M. (2006). Volatile components of Centaurea calcitrapa L. and Centaurea sphaerocephala L. ssp. sphaerocephala, two Asteraceae growing wild in Sicily. Flavour Fragr. J. 21: 282-285. 36. Formisano, C., Rigano, D., Senatore, F., Bruno, M., Rosselli, S., Raimondo, F.M., Spadaro, V. (2008). Chemical composition of the essential oils of Centaterea sicana and C. giardinae growing wild in Sicily. Nat. Prod. Commun. 3, 6: 919-922. 37. Altintas, A., Kose, Y.B., Yucel, E., Demirci, B., Baser, K.H.C. (2006). Composition of the essential oil of Centaurea dichroa. Chem. Nat. Compd. 40, 6: 604-605. 38. Baser, K.H.C., Özek, G., Özek, T., Duran, A. (2006). Composition of the essential oil of Centaurea huber-morathii Wagenitz isolated from seeds by microdistillation. Flavour Fragr. J. 21: 568-570. 39. Kose, Y.B., Altintas, A., Tugay, O., Uysal, T., Demirci, B., Ertugrul, K., Baser, K.H.C. (2010). Composition of the Essential Oils of Centaurea sericeae Wagenitz and Centaurea ensiformis PH Davis from Turkey. Asian J. Chem. 22, 9: 7159-7163. 40. Altintas, A., Koca, U., Demirci, B., Baser, K.H.C. (2010). Essential Oil Composition of Endemic Centaurea tchihatcheffii Fisch and Mey. from Turkey. Asian J. Chem. 22, 6: 4711-4716. 41. Polatoglu, K. , Demirci, B., Goren, N., Baser, K.H.C. (2011). Essential oil composition of Tanacetum kotschyi from Turkey. Chem. Nat. Compd. 47, 2: 297-299. 42. Tabanca, N. Demirci, B., Baser, K.H.C., Aytac, Z., Ekici, M., Khan, S.I., Jacob, M.R., Wedge, D.E. (2006). Chemical Composition and Antifungal Activity of Salvia macrochlamys and Salvia recognita Essential Oils. J. Agric. Food Chem., 54, 18: 6593-6597. 43. Polatoglu, K., Demirci, F., Demirci, B., Gören, N., Baser, K.H.C. (2010). Essential Oil Com- position and Antibacterial Activity of Tanacetum argenteum (Lam.) Willd. ssp. argenteum and T. densum (Lab.) Schultz Bip. ssp. amani Heywood from Turkey. J. Oleo Sci. 59, 7: 361-367. 44. Polatoglu, K., Demirci, F., Demirci, B., Gören, N., Baser, K.H.C. (2012). Essential Oil Composition and Antimicrobial Activities of Tanacetum chiliophyllum (Fisch. & Mey.) Schultz Kaan Polatoglu et al., / TEOP 17 (6) 2014 1268 - 1278 1278 Bip. var. monocephalum Grierson from Turkey. Rec. Nat. Prod. 6, 2: 184-188. 45. Tabanca, N., Demirci, B., Ozek, T., Kirimer, N., Baser, K.H.C., Bedir, E., Khan, I.A., Wedge, D.E. (2005). Gas chromatographic–mass spectrometric analysis of essential oils from Pimpinella species gathered from Central and Northern Turkey. J. Chromatogr. A. 1097: 192-198. 46. Demirci, F., Güven, K., Demirci, B., Dadandi, M.Y., Baser, K.H.C. (2008). Antibacterial activity of two Phlomis essential oils against food pathogens. Food Control. 19, 12: 1159-1164. 47. Polatoglu, K., Gören, N., Baser, K.H.C., Demirci, B. (2009). The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey. J. Essent. Oil Res. 21, 2: 97-100. 48. Polatoglu, K., Demirci, B., Goren, N., Baser, K.H.C. (2011). Essential oil composition of endemic Tanacetum zahlbruckneri (Náb.) and Tanacetum tabrisianum (Boiss.) Sosn. and Takht. from Turkey. Nat. Prod. Res. 25, 6: 576-584. 49. Baser, K.H.C., Demirci, B., Tabanca, N., Özek, T., Gören, N. (2001). Composition of the essential oils of Tanacetum armenum (DC.) Schultz Bip., T. balsamita L., T. chiliophyllum (Fisch. & Mey.) Schultz Bip. var. chiliophyllum and T. haradjani (Rech. fil.) Grierson and the enantiomeric distribution of camphor and carvone. Flavour Fragr. J. 16: 195-200.