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Essential Oil Composition of Centaurea Stenolepis Kerner. from Turkey

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Essential Oil Composition of Centaurea Stenolepis Kerner. from Turkey Journal of Essential Oil Bearing Plants ISSN: 0972-060X (Print) 0976-5026 (Online) Journal homepage: https://www.tandfonline.com/loi/teop20 Essential Oil Composition of Centaurea 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 Centaureastenolepis 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. Submit your article to this journal Article views: 98 View related articles View Crossmark data Citing articles: 3 View citing articles 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: Asteraceae, 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. cyanus 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.
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