This article was downloaded by: [POLATOĞLU, Kaan][TÜBİTAK EKUAL] On: 14 March 2011 Access details: Access Details: [subscription number 772815469] Publisher Taylor & Francis Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House, 3741 Mortimer Street, London W1T 3JH, UK Natural Product Research Publication details, including instructions for authors and subscription information: http://www.informaworld.com/smpp/title~content=t713398545 Essential oil composition of endemic Tanacetum zahlbruckneri (Náb.) and Tanacetum tabrisianum (Boiss.) Sosn. and Takht. from Turkey Kaan Polatoğlua; Betül Demircib; Nezhun Görena; Kemal Hüsnü Can Başerb a Department of Biology, Faculty of Science & Letters, Yıldız Technical University, İstanbul 34210, Turkey b Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey Online publication date: 14 March 2011 To cite this Article Polatoğlu, Kaan , Demirci, Betül , Gören, Nezhun and Başer, Kemal Hüsnü Can(2011) 'Essential oil composition of endemic Tanacetum zahlbruckneri (Náb.) and Tanacetum tabrisianum (Boiss.) Sosn. and Takht. from Turkey', Natural Product Research, 25: 6, 576 — 584 To link to this Article: DOI: 10.1080/14786419.2010.483434 URL: http://dx.doi.org/10.1080/14786419.2010.483434 PLEASE SCROLL DOWN FOR ARTICLE Full terms and conditions of use: http://www.informaworld.com/terms-and-conditions-of-access.pdf This article may be used for research, teaching and private study purposes. Any substantial or systematic reproduction, re-distribution, re-selling, loan or sub-licensing, systematic supply or distribution in any form to anyone is expressly forbidden. The publisher does not give any warranty express or implied or make any representation that the contents will be complete or accurate or up to date. The accuracy of any instructions, formulae and drug doses should be independently verified with primary sources. The publisher shall not be liable for any loss, actions, claims, proceedings, demand or costs or damages whatsoever or howsoever caused arising directly or indirectly in connection with or arising out of the use of this material. Natural Product Research Vol. 25, No. 6, March 2011, 576–584 Essential oil composition of endemic Tanacetum zahlbruckneri (Náb.) and Tanacetum tabrisianum (Boiss.) Sosn. and Takht. from Turkey Kaan Polatoğlua*, Betül Demircib, Nezhun Görena and Kemal Hüsnü Can Bas° erb _ Department of Biology, Faculty of Science & Letters, Y{ld{z Technical University, Istanbul 34210, Turkey; bDepartment of Pharmacognosy, Faculty of Pharmacy, Anadolu University, Eskis° ehir 26470, Turkey a Downloaded By: [POLATOLU, Kaan][TÜBTAK EKUAL] At: 18:53 14 March 2011 (Received 16 February 2010; final version received 2 April 2010) In this study, water-distilled essential oils from the flowers of Tanacetum zahlbruckneri and flowers and stems of Tanacetum tabrisianum from Turkey were analysed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). The flower oil of T. zahlbruckneri was characterised by the sesquiterpenes germacrene D (29.7%) and spathulenol (12%). Flower (A) and stem (B) oil of T. tabrisianum was characterised by 1,8-cineole: 17.6% (A), 22.5% (B), hexadecanoic acid: 10.3% (A), 8% (B), decanoic acid: 5.8% (A) and trans-linalooloxide acetate: 5.3% (A), 4% (B). Unlike a previous report on the essential oil composition of T. tabrisianum, in this study a 1,8-cineole and hexadecanoic acid-rich oil with a low percentage of caryophyllene oxide and spathulenol was obtained. The composition of the essential oil of endemic T. zahlbruckneri was investigated for the first time. Keywords: Tanacetum zahlbruckneri; T. tabrisianum; Asteraceae; essential oils; 1,8-cineole; germacrene D; spathulenol; hexadecanoic acid 1. Introduction A summary of the previous investigations into the main essential oil components of Tanacetum species from Turkey is given in Table 1. Essential oils of Tanacetum species are usually represented by camphor, 1,8-cineole, -thujone and borneol, accompanied by various minor components. In some cases, carvone, -pinene, -eudesmol and trans-chrysanthenol have been observed as the main components. Chemovariation is usually encountered in Tanacetum species, which can be clearly seen in Table 1 and other references not given in the table (De Pooter, Vermeesch, & Schamp, 1989; Hendriks, Van Der Elst, Van Putten, & Bos, 1990; Holopainen, Hiltunen, & Von Schantz, 1987). Tanacetum tabrisianum occurs in southwest Asia, as well as in Turkey and Iran (Davis, 1975). A previous report on T. tabrisianum of Iranian origin revealed its essential oil composition (Habibi, Biniyaz, & Ghodrati, 2007). To the best of our knowledge, there is no previous report on the chemistry of this species. This investigation revealed differences in the oil compositions of T. tabrisianum from Iran *Corresponding author. Email: kaanpolatoglu@gmail.com ISSN 1478–6419 print/ISSN 1029–2349 online ß 2011 Taylor & Francis DOI: 10.1080/14786419.2010.483434 http://www.informaworld.com Downloaded By: [POLATOLU, Kaan][TÜBTAK EKUAL] At: 18:53 14 March 2011 Table 1. Comparison of the percentage of main essential oil components from the previous reports of Tanacetum species. Tanacetum species T. argyrophyllum var. argyrophyllum T. argenteum ssp. canum var. canum T. argenteum ssp. flabellifolium T. balsamita T. balsamita ssp. balsamita T. chiliophyllum var. chiliophyllum Fl L AP L Main components (%) -Thujone (62.8) -Thujone (51.8) -Thujone (69.9) AP Caryophyllene oxide (12.6) -Pinene (29.1) AP Borneol (28.1) Secondary components (%) – 1,8-Cineole (11.1) -Thujone (5.6) -Thujone (11.9) Minor compounds (5%  X%) – – – -Caryophyllene (5.1) (E )-Sesquilavandulol (15.9) Camphor (14) 1,8-Cineole (12.3) Bornyl acetate (10); terpinen-4-ol (7.1) – -Thujone (51.1) -Thujone (10) L AP 1,8-Cineole (31.3) Camphor (26.7) Camphor (8.6) 1,8-Cineole (11.3) AP AP Fl Carvone (52.4) trans-Chrysanthenol (22.3) Camphor (16.8) AP Camphor (17.9) -Thujone (11.7) Chrysanthenyl acetate (19.7) cis-Chrysanthenyl acetate (16.3) 1,8-Cineole (16.6) AP Camphor (28.5) 1,8-Cineole (17.1) Gören, Demirci, and Bas° er (2001) Akpulat, Tepe, Sokmen, Daferera, and Polissiou (2005) Gören et al. (2001) Tabanca, Demirci, Demirci, Wedge, and Bas° er (2007) Gören et al. (2001) -Terpineol (5.5) Borneol (10.6); -eudesmol (5.5) – Linalool oxide (11.5); camphor (7.5) -Thujone (12.5) Bas° er et al. (2001) Borneol (15.4); dihydro-cyclogeranyl hexanoate (10.1) Camphene (7.1); isobornyl propionate (5.4) Salamci et al. (2007) Bagci et al. (2008) Bas° er et al. (2001) Bagci et al. (2008) 577 AP References Natural Product Research T. praeteritum ssp. praeteritum T. praeteritum ssp. massicyticum T. armenum Plant part studied Downloaded By: [POLATOLU, Kaan][TÜBTAK EKUAL] At: 18:53 14 March 2011 578 Lf AP Camphor (15.9) -Patchoulene (17.5) 1,8-Cineole (10) Camphor (15.6) T. densum ssp. sivasicum Fl St AP AP 1,8-Cineole (21.1) 1,8-Cineole (28.3) Camphor (56.8) 1,8-Cineole (23.8) Camphor (19.2) Camphor (16.4) Camphene (12.7) Camphor (11.6) AP 1,8-Cineole (18.9) p-Cymene (15.7) Fl -Thujone (25) T. parthenium T. aucheranum T. cadmeum ssp. orientale St Rt cis-Linalool oxide (12.8) -Eudesmol (13.8) -Eudesmol (10.3) trans-Chrysanthenyl acetate (8.5) Hexadecanoic acid (6) Fl St Camphor (25.9) Borneol (25.8) Borneol (15.4) Camphor (14.8) T. macrophyllum Rt AP Nonacosane (16.2) -Eudesmol (21.4) Spathulenol (6.8) cis-Chrysanthenol (12) T. alyssifolium AP Borneol (35.2) -Thujone (24.6) Note: Fl, flower oil; Lf, leaf oil; St, stem oil; Rt, root oil; AP, aerial parts oil. Terpinen-4-ol (6.7) 1,8-Cineole (11.5); borneol (7.5); p-cymene (6.1); santolinatriene (5); -selinene (5) Borneol (5.8) Borneol (6.4) p-Cymene (5.2) Terpinen-4-ol (7.2); -terpineol (6.5) Terpinen-4-ol (14.8); borneol (9.8) cis-Linalool oxide (6.8); trans-chrysanthenyl acetate (5.8) 1,8-Cineole (6.6); -eudesmol (6.2); -thujone (5.2) Spathulenol (5.8); T-muurolol (5.3) -Thujone (7.8) 1,8-Cineole (7.4); -thujone (5.5) Hexadecanoic acid (5.8) Camphor (5.8); copaborneol (5.6) Camphor (12.4); -eudesmol (6.1) Bas° er et al. (2001) Özen, Toker, and Ertekin (2003) Polatoğlu, Gören, Bas° er, and Demirci (2009a) Akpulat et al. (2005) Salamci et al. (2007) Özek et al. (2007) Polatoğlu et al. (2009b) Demirci and Bas° er (2007) Kandemir, Ozer, Kilic, Cakir, and Demir (2008) K. Polatoğlu et al. T. haradjani T. densum ssp. amani Natural Product Research 579 and Turkey. The comparison of the main essential oil components of T. tabrisianum mentioned in the previous report, together with the present data, are given in Table 2. Tanacetum zahlbruckneri, endemic to Turkey, finds its natural habitat on the stony slopes of mountains at 1300–3000 m altitude in the eastern provinces (Davis, 1975). To the best of our knowledge, there is no previous report on the chemistry of this species. As a part of our phytochemical and biological investigation of Tanacetum species, we report here on the essential oil composition of T. tabrisianum and T. zahlbruckneri from Turkey. Downloaded By: [POLATOLU, Kaan][TÜBTAK EKUAL] At: 18:53 14 March 2011 2. Results The essential oil compositions of T. tabrisianum flowers (A), stems (B) and T. zahlbruckneri flowers (C) are given in Supplementary Table S1 (online only). Ninety-seven compounds were identified representing 95.5% of the flower (A) oil. 1,8-Cineole (17.6%), hexadecanoic acid (10.3%), decanoic acid (5.8%) and translinalool oxide acetate (5.3%) were found to be the main components of the oil A. Eighty-four compounds were identified representing 91.6% of stem (B) oil. 1,8Cineole (22.5%) and hexadecanoic acid (8%) were found to be the main components of oil B. Fifty-eight compounds were identified representing 74.9% of flower (C) oil. Germacrene D (22.7%) and spathulenol (9.7%) were found to be the main components of oil C. A previous report on Iranian T. tabrisianum indicated an essential oil with caryophyllene oxide, spathulenol, cis-carveol, trans-isolongifolanone and camphor as the main components (Habibi et al., 2007), unlike the main components we encountered in the Turkish sample. The main components of the Iranian sample, caryophyllene oxide and spathulenol, occurred in small quantities in our sample, except for 1,8-cineole. The minor compounds accompanying the main components in the Iranian sample did not exist or existed in small quantities in the Turkish T. tabrisianum oil. The main components of the Turkish T. tabrisianum oil were 1,8-cineole and hexadecanoic acid, while only 1,8-cineole was present in Iranian Table 2. Comparison of the percentage of main essential oil components from the previous report of T. tabrisianum together with the present data. Compound Caryophyllene oxide Spathulenol 1,8-Cineole cis-Carveol trans-Isolongifolanone Carvone Camphor trans-Linalooloxide acetate Borneol Decanoic acid Hexadecanoic acid Habibi et al. (2007) (%) A (%) B (%) 12 10.3 9.1 6.7 6.1 5.3 5.2 – – – – 0.3 0.4 17.6 – – – 1.4 5.3 6.9 5.8 10.3 0.3 0.9 22.5 – – – 0.8 4 3.3 – 8 Note: A: T. tabrisianum flower oil; B: T. tabrisianum stem oil. 580 K. Polatoğlu et al. Downloaded By: [POLATOLU, Kaan][TÜBTAK EKUAL] At: 18:53 14 March 2011 oil, and as a minor constituent. Also, none of the minor compounds occurring 5% in the Turkish T. tabrisianum oil existed in the Iranian oil. Compounds 1,8-cineole and camphor, which are usually observed in Tanacetum oils, existed in both oils. The oil of T. zahlbruckneri was dominated by sesquiterpenes and oxygenated sesquiterpenes, where germacrene D was the main component. Tanacetum essential oils with high germacrene D have been previously reported: it is noted as a main component in Tanacetum vulgare chemotypes (Holopainen et al., 1987), and as a secondary component in the oils of Tanacetum parthenium (Mirjalili, Salehi, Sonboli, & Mohammadi Vala, 2007) and T. vulgare (De Pooter et al., 1989; Hendriks et al., 1990). 3. Discussion Chemovariation is a well-documented fact in the essential oils of Tanacetum species, especially for T. vulgare (Collin, Deslauriers, Pageau, & Gagnon, 1993; De Pooter et al., 1989; Hendriks et al., 1990; Judzentiene & Mockute, 2004; Keskitalo, Pehu, & Simon, 2001; Rohloff, Mordal, & Dragland, 2004). Also, in more recent years, chemovariation in other Tanacetum species has been reported, such as in the cases of Tanacetum chiliophyllum var. chiliophyllum, Tanacetum nubigenum and Tanacetum cadmeum ssp. orientale (Bagci, Kursat, Kocak, & Gur, 2008; Bas° er, Demirci, Tabanca, Özek, & Gören, 2001; Chanotiya & Mathela, 2007; Chanotiya, Sammal, & Mathela, 2005; Dev et al., 2001; Mathela, Padalia, & Joshi, 2008; Polatoğlu, Gören, Bas° er, & Demirci, 2009b; Salamci, Kordali, Kotan, Cakir, & Kaya, 2007). The only report on the essential oil of Iranian T. tabrisianum presented its main component as caryophyllene oxide and with the secondary component spathulenol (Habibi et al., 2007). However, to the best of our knowledge, there is no report on an oil of this species with a high content of 1,8-cineole and hexadecanoic acid. The precursor in the biosynthesis of sesquiterpenes is farnesyl diphosphate. Carbocationic cyclisation reactions, depending on the stereochemistry of the double bonds (also, in some cases, by the aid of enzymes to fold the carbon chain in farnesyl cation), results in a variety of sesquiterpene cations. Caryophyllyl cation is produced by a carbocationic cyclisation reaction from humulyl cation, which is produced from a farnesyl cation (Dewick, 2001). Similarly, spathulenol is produced from a guaiyl cation with further oxidation and reduction steps. Caryophyllene oxide and spathulenol were also present in the Turkish T. tabrisianum but in very small amounts (40.5%). Some of the minor compounds occurring in both the oils from Iranian and Turkish sources differed in their biosynthetic origins, except for the compounds borneol and camphor. Borneol is produced in plants by enzymatic folding, carbocationic rearrangement of an -terpinyl cation and oxidation of the resultant bornyl cation; further oxidation leads to the production of camphor (Dewick, 2001; Wise & Croteau, 1999). Camphor (5.2%) was present in the Iranian oil. However, interestingly, borneol was completely missing, while in the Turkish oil camphor was present in small amounts (1.4–0.8%), together with borneol in higher amounts (6.9–3.3%). Both oils contained high amounts of 1,8-cineole. However, in the Turkish sample it was present as the main component. Unlike most investigated Tanacetum species, T. zahlbruckneri oil was dominated by sesquiterpenes and oxygenated sesquiterpenes. The main components of T. zahlbruckneri, germacrene D Natural Product Research 581 and spathulenol, were encountered in Tanacetum species, but not frequently as the main component. The differences encountered in Turkish and Iranian T. tabrisianum suggested a possible chemovariation due to differences in the biosynthetic origin of the main components, together with the accompanying minor components. Downloaded By: [POLATOLU, Kaan][TÜBTAK EKUAL] At: 18:53 14 March 2011 4. Experimental 4.1. Plant materials Plant materials were collected during the flowering period of T. tabrisianum on 23 July 2006 from Van-Güzeldere at 2594 m altitude and T. zahlbruckneri on 20 July 2006 from Van-Bahçesaray at 2565 m altitude. Voucher specimens have been deposited at the Herbarium of the Faculty of Science, Istanbul University (voucher no. ISTE 83757 and ISTE 83747), Turkey. The plant materials were identified by Dr Kerim Alp|nar. 4.2. Methods 4.2.1. Isolation of the essential oils Flowers (A) and stems (B) (100 g each) of the plant sample T. tabrisianum from Van-Güzeldere and flowers (C) of T. zahlbruckneri from Van-Bahçesaray were separately subjected to hydrodistillation for 4 h using a Clevenger-type apparatus to produce the oils. Yellow-coloured oils were obtained in yields of 0.16% (A) and 0.10% (B) (v/w). A trace amount of oil was obtained from T. zahlbruckneri flowers (C). Oil (C) was trapped in n-hexane to recover. 4.2.2. Essential oil analysis The essential oil analyses were carried out simultaneously by GC and GC–MS systems. 4.2.2.1. GC–MS analysis. This analysis was performed with an Agilent 5975 GC-MSD system with an Innowax FSC column (60 m  0.25 mm, 0.25 mm film thickness) and with helium as a carrier gas (0.8 mL min 1). The oven temperature was programmed to 60 C for 10 min and raised to 220 C at the rate of 4 C min 1. The temperature was kept constant at 220 C for 10 min and then raised to 240 C at the rate of 1 C min 1. Mass spectra were recorded at 70 eV with the mass range m/z 35–450. 4.2.2.2. GC analysis. These analyses were carried out with an Agilent 6890N GC system. The flame ionisation detector (FID) temperature was set to 300 C and the same operational conditions were applied to a duplicate of the same column used in the GC–MS analyses. Simultaneous auto injection was done to obtain the same retention times. Relative percentage amounts of the separated compounds were calculated from the integration of the peaks in FID chromatograms. The result of the analysis is given in Supplementary Table S1 (online only). 582 K. Polatoğlu et al. 4.2.2.3. Identification of components. Identification of essential oil components was carried out by the comparison of their retention times with those of authentic samples or by the comparison of their relative retention indices (RRI) to a series of n-alkanes. The commercial data (Wiley GC/MS Library, Adams Library, MassFinder 2.1 Library; Joulain, König, & Hochmuth, 2001; McLafferty & Stauffer, 1989) were matched against the in-house Bas° er Library of Essential Oil Constituents, built up by genuine compounds and components of known oils, as well as MS data from the literature (ESO, 1999; Jennings & Shibamoto, 1980; Joulain & König, 1998) using a computer for identification. Downloaded By: [POLATOLU, Kaan][TÜBTAK EKUAL] At: 18:53 14 March 2011 5. Conclusions Essential oil compositions of T. tabrisianum flower and stem oils and T. zahlbruckneri flower oil from Van, Turkey, were investigated. 1,8-Cineole and hexadecanoic acid-rich oils were observed from T. tabrisianum, which was unlike a previous report. The differences encountered in our previous research and literature on this plant suggested possible chemovariation in this plant. However, the comparison of deoxyribonucleic acid (DNA) profiles of this plant from various locations could confirm the existence of chemotypes. The essential oil composition of T. zahlbruckneri flowers was investigated, and germacrene D and spathulenol were observed as the main components. Supplementary material Table S1 relating to this paper is available online. Acknowledgements This research was supported by the Scientific and Technological Research Council of Turkey (TUBITAK-TBAG 104T306). References Akpulat, H.A., Tepe, B., Sokmen, A., Daferera, D., & Polissiou, M. (2005). Composition of the essential oils of Tanacetum argyrophyllum (C. Koch) Tvzel. var. argyrophyllum and Tanacetum parthenium (L.) Schultz Bip. (Asteraceae) from Turkey. Biochemical Systematics and Ecology, 33, 511–516. Bagci, E., Kursat, M., Kocak, A., & Gur, S. (2008). Composition and antimicrobial activity of the essential oils of Tanacetum balsamita L. subsp. balsamita and T. chiliophyllum (Fisch. et Mey.) Schultz Bip. var. chiliophyllum (Asteraceae) from Turkey. Journal of Essential Oil Bearing Plants, 11, 479–484. Bas° er, 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 and Fragrance Journal, 16, 195–200. Downloaded By: [POLATOLU, Kaan][TÜBTAK EKUAL] At: 18:53 14 March 2011 Natural Product Research 583 Chanotiya, C.S., & Mathela, C.S. (2007). Two distinct essential oil bearing races of Tanacetum nubigenum Wallich ex DC from Kumaon Himalaya. Natural Product Communications, 2, 785–788. Chanotiya, C.S., Sammal, S.S., & Mathela, C.S. (2005). Composition of a new chemotype of Tanacetum nubigenum. Indian Journal of Chemistry Section B, 44, 1922–1926. Collin, G.J., Deslauriers, H., Pageau, N., & Gagnon, M. (1993). Essential oil of tansy (Tanacetum vulgare L.) of Canadian origin. Journal of Essential Oil Research, 5, 625–627. Davis, P.H. (1975). Flora of Turkey and the East Aegean lslands (Vol. 5). Edinburgh: Edinburgh University Press. De Pooter, H.L., Vermeesch, J., & Schamp, N.M. (1989). The essential oils of Tanacetum vulgare (L.) and Tanacetum parthenium (L.) Schultz-Bip. Journal of Essential Oil Research, 1, 9–13. Demirci, B., & Bas° er, K.H.C. (2007). The essential oil composition of Tanacetum macrophyllum (Waldst. et Kit.) Schultz. Bip. Journal of Essential Oil Research, 19, 255–257. Dev, V., Beuchamp, P., Kashyap, T., Melkani, A., Mathela, C., & Bottini, A.T. (2001). Composition of the essential oil of Tanacetum nubigenum Wallich ex De. Journal of Essential Oil Research, 13, 319–323. Dewick, P.M. (2001). Medicinal natural products: A biosynthetic approach (2nd ed.). Chichester: John Wiley & Sons Ltd. ESO 2000. (1999). The complete database of essential oils. The Netherlands: Boelens Aroma Chemical Information Service. Gören, N., Demirci, B., & Bas° er, K.H.C. (2001). Composition of the essential oils of Tanacetum ssp. from Turkey. Flavour and Fragrance Journal, 16, 191–194. Habibi, Z., Biniyaz, T., & Ghodrati, T. (2007). Volatile constituents of Tanacetum paradoxum Bornm. and Tanacetum tabrisianum (Boiss.) Sosn. et Takht., from Iran. Journal of Essential Oil Research, 19, 11–13. Hendriks, H., Van Der Elst, D.J.D., Van Putten, F.M.S., & Bos, R. (1990). The essential oil of Dutch tansy (Tanacetum vulgare L.). Journal of Essential Oil Research, 2, 155–160. Holopainen, M., Hiltunen, R., & Von Schantz, M. (1987). A study on tansy chemotypes. Planta Medica, 53, 284–287. Jennings, W.G., & Shibamoto, T. (1980). Quantitative analysis of flavor and fragrance volatiles by glass capillary GC. New York: Academic Press. Joulain, D., & König, W.A. (1998). The atlas of spectra data of sesquiterpene hydrocarbons. Hamburg: EB-Verlag. Joulain, D., König, W.A., & Hochmuth, D.H. (2001). Terpenoids and related constituents of essential oils. Hamburg: Library of MassFinder 2.1. Judzentiene, A., & Mockute, D. (2004). Composition of the essential oils of Tanacetum vulgare L. growing wild in Vilnius District (Lithuania). Journal of Essential Oil Research, 16, 550–553. Kandemir, A., Ozer, H., Kilic, H., Cakir, A., & Demir, Y. (2008). Essential oil composition of Tanacetum alyssifolium, an endemic species from Turkey. Chemistry of Natural Compounds, 44, 530–531. Keskitalo, M., Pehu, E., & Simon, J.E. (2001). Variation in volatile compounds from tansy (Tanacetum vulgare L.) related to genetic and morphological differences of genotypes. Biochemical Systematics and Ecology, 29, 267–285. Mathela, C.S., Padalia, R.C., & Joshi, R.K. (2008). Variability in fragrance constituents of Himalayan Tanacetum species: commercial potential. Journal of Essential Oil Bearing Plants, 11, 503–513. Downloaded By: [POLATOLU, Kaan][TÜBTAK EKUAL] At: 18:53 14 March 2011 584 K. Polatoğlu et al. McLafferty, F.W., & Stauffer, D.B. (1989). The Wiley/NBS registry of mass spectral data. New York: John Wiley & Sons Ltd. Mirjalili, M.H., Salehi, P., Sonboli, A., & Mohammadi Vala, M. (2007). Essential oil composition of feverfew (Tanacetum parthenium) in wild and cultivated populations from Iran. Chemistry of Natural Compounds, 43, 218–220. _ can, G., Bas° er, K.H.C., Hamzaoglu, E., & Duran, A. (2007). Özek, G., Özek, T., Is° Composition and antimicrobial activity of the essential oil of Tanacetum cadmeum (Boiss.) Heywood subsp. orientale Grierson. Journal of Essential Oil Research, 19, 392–395. Özen, H.Ç., Toker, Z., & Ertekin, S.A. (2003). Composition of the essential oil of Tanacetum densum (Lab.) Schultz Bip. Subsp. amani Heywood. Advances in Food Science, 25, 159–161. Polatoğlu, K., Gören, N., Bas° er, K.H.C., & Demirci, B. (2009a). The essential oil composition of Tanacetum densum (Labill.) Heywood ssp. sivasicum Hub.-Mor. and Grierson from Turkey. Journal of Essential Oil Research, 21, 1–3. Polatoğlu, K., Gören, N., Bas° er, K.H.C., & Demirci, B. (2009b). The variation in the essential oil composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey. Journal of Essential Oil Research, 21, 97–100. Rohloff, J., Mordal, R., & Dragland, S. (2004). Chemotypical variation of tansy (Tanacetum vulgare L.) from 40 different locations in Norway. Journal of Agricultural and Food Chemistry, 52, 1742–1748. Salamci, E., Kordali, S., Kotan, R., Cakir, A., & Kaya, Y. (2007). Chemical compositions, antimicrobial and herbicidal effects of essential oils isolated from Turkish Tanacetum aucheranum and Tanacetum chiliophyllum var. chiliophyllum. Biochemical Systematics and Ecology, 35, 569–581. Tabanca, N., Demirci, F., Demirci, B., Wedge, D.E., & Bas° er, K.H.C. (2007). Composition, enantiomeric distribution, and antimicrobial activity of Tanacetum argenteum subsp. flabellifolium essential oil. Journal of Pharmaceutical and Biomedical Analysis, 45, 714–719. Wise, M.L., & Croteau, R. (1999). Monoterpene biosynthesis. In S.D. Barton, K. Nakanishi, & O. Meth-Cohn (Eds.), Comprehensive natural products chemistry (pp. 107–109). Amsterdam: Elsevier Science Publishers.