Determination of the volatile compounds of Anthemis cretica subsp. anatolica (Boiss.) Grierson

Abstract

Chemical composition of the essential oils obtained by hydrodistillation from the aerial parts of Anthemis cretica subsp. anatolica was analyzed by gas chromatography (GC) and gas chromatography-mass spectroscopy (GC-MS) systems. The essential oil of A. cretica subsp. anatolica was characterized by the presence of a high percentage of oxygenated sesquiterpenes (57.9%). Twenty-seven compounds were identified representing 96.6 % of the essential oil of A. cretica subsp. anatolica. The main components of the oil were spathulenol (27.0%) and hexadecanoic acid (14.3%).

Keywords

• Anthemis cretica subsp. anatolica
• essential oil
• GC-FID and GC-MS

Kaynakça

1. Albay, C.G., Albay, M., Yayli, N. and Yildirim, N. (2009). Activities of Anthemis marschalliana ssp pectinata and Anthemis cretica ssp argaea from Turkey, Asian journal of chemistry, 21(2), 1425-1431.
2. Albayrak, S. and Aksoy, A. (2013). Evaluatıon of antioxidant and antimicrobial activities of two endemic Anthemis species in Turkey. Journal of Food Biochemistry 37(6); 639-645.
3. Alessandro, V., Claudio, F., Giacomo, R., Mirella, D.C., Giampiero, C., Mauro, S. and Armandodoriano, B. (2016). Secondary metabolites with ecologic and medicinal implications in Anthemis cretica subsp. petraea from Majella National Park. AIMS Molecular Science, 3(4), 648-660.
4. Babushok, V.I., Linstrom, P.J. and Zenkevich, I.G. (2011). Retention Indices for Frequently Reported Compounds of Plant Essential Oils. J. Phys. Chem. Ref. Data, 40 (4).
5. Baytop, T. (1999). Türkiye’de Bitkiler ile Tedavi, Geçmiste ve Bugün (Therapy with Medicinal Plants in Turkey, Past and Present), 2nd ed., Nobel Tıp Kitabevleri, Istanbul, Turkey.
6. Bruno, M., Bonoi, M.L., Vassallo, N., Gedris, T.E. and Herz, W. (1997). Guaianolides and other terpenoids from Anthemis aetnensis, Phytochemistry, 45, 375-377.
7. Curvers, J., Rijks, J., Cramers, C.A.M.G., Knauss, K. and Larson, P. (1985). Temperature programmed retention indices: Calculation from isothermal data. Part 1: Theory, Journal of Separation Science, 8 (9), 607-610.
8. Dolarslan, M. and Gurkok, T. (2018). Morphologic and Essential oil Profiles of Three Species from Asteraceae, Natural Product Communications, 13 (8), 1039-1042.

9. ESO 2000 (1999). The Complete Database of Essential Oils. Boelens Aroma Chemical Information Service: The Netherlands.
10. Gonenc, T., Argyropoulou, C., Erdogan, T., Gousiadou, C., Juergenliemk, G., Kıvcak, B. and Skaltsa, H. (2011). Chemical constituents from Anthemis wiedemanniana Fisch. & Mey., Biochem Syst Ecol., 39, 51-55.
11. Grierson, A.J.C. and Yavin, Z. (1975). Anthemis L. In: Davis PH (ed). Flora of Turkey and the East Aegean Islands, vol. 5. Edinburgh University Press, Edinburgh, 174–221.
12. Guragaç Dereli F. T., Ilhan, M. and Esra Küpeli Akkol, E.K. (2018). Discovery of new antidepressant agents: In vivo study on Anthemis wiedemanniana Fisch. & Mey, Journal of Ethnopharmacology, 226, 11–16.
13. Hochmuth, D.H. (2008). MassFinder-4, Hamburg-Germany, Hochmuth Scientific Consulting.
14. Hofer, O. and Greger, H. (1985). New Sesquiterpene-Coumarin Ethers from Anthemis cretica, Liebigs Annalen der Chemie, 6, 1136-1144.
15. Hulley, I.M., Sadgrove, N.J., Tilney, P.M., Ozek, G., Yur, S., Ozek, T., Baser, K.H.C. and van Wyk, B.E. (2018). Essential oil composition of Pentzia incana (Asteraceae), an important natural pasture plant in the Karoo region of South Africa, African Journal of Range & Forage Science, 35 (2), 137–145.
16. Javidnia, K., Miri, R., Kamalinejad, M., Sarkarzadeh, H. and Jamalian, A. (2004). Chemical composition of the essential oils of Anthemis altissima L. grown in Iran, Flavour Fragr J., 19, 213-216.
17. Joulain, D. and Koenig, W.A. (1998). The Atlas of Spectra Data of Sesquiterpene Hydrocarbons. E.B.-Verlag Hamburg .
18. Kaya, A., Dinc, M., Dogu, S. and Demirci, B. (2017). Compositions of essential oils of Salvia adenophylla, Salvia pilifera, and Salvia viscosa in Turkey, J. Essent. Oil Res., 29( 3), 233-239.
19. Kendir, G., Koroglu, A., Ozek, G., Ozek, T. and Baser, K.H.C. (2019). Glandular trichome structures and chemical composition of the volatiles of five Ribes species from Turkey, J. Essent. Oil Res., 31( 2), 111–119.
20. Kilic, O., Kocak, A. and E. Bagci, E. (2011). Composition of the Volatile Oils of Two Anthemis L. Taxa from Turkey, Z. Naturforsch , 66 c: 535-540.
21. Kivcak, B., Mert, T., Saglam, H., Ozturk, T., Kurkcuoglu, M. and Baser, K.H.C. (2007). Chemical composition and antimicrobial activity of the essential oil of Anthemis wiedemanniana from Turkey, Chem Nat Compd., 43, 47-51.
22. Korkmaz, M. and Karakus, S. (2015). Traditional uses of medicinal plants of uzumlu district, Erzincan, Turkey, Pakistan Journal of Botany, 47(1), 125-134.
23. Kultur, S. (2007). Medicinal plants used in Kırklareli Province (Turkey), J Ethnopharmacol, 111, 341-364.
24. Kurtulmus, A., Fafal, T., Mert, T., Saglam, H., Kivcak, B., Ozturk, T., B. Demirci, B. and Baser, K.H.C. (2009). Chemical Composition and Antimicrobial Activity of the Essential Oils of Three Anthemis Species from Turkey, Chemistry of Natural Compounds, 45 (6), 900-904.
25. McLafferty, F.W. and Stauffer, D.B.(1989). The Wiley/NBS Registry of Mass Spectral Data; J. Wiley and Sons: New York.
26. Orlando, G., Zengin, G., Ferrante, C., Ronci, M., Recinella, L., Senkardes, I., Gevrenova, R., Zheleva-Dimitrova, D., Chiavaroli, A., Leone, S., Di Simone, S., Brunetti, L., Picot-Allain, C.M.N., Mahomoodally, M.F., Sinan, K.I. and Menghini, L. (2019). Comprehensive Chemical Profiling and Multidirectional Biological Investigation of Two Wild Anthemis Species (Anthemis tinctoria var. pallida and A. cretica subsp. tenuiloba): Focus on Neuroprotective Effects, Molecules, 24: 2582.
27. Ozek, G., Suleimen, Y., Tabanca, N., Doudkin, R., Gorovoy, P.G., Goger, F., Wedge, D.E., Ali, A., Khan I.A. and K.H.C. Baser, K.H.C. (2014). Chemical Diversity and Biological Activity of the Volatiles of Five Artemisia Species from Far East Russia, Rec. Nat. Prod, 8 (3), 242-261.
28. Ozbek, M.U. (2012). Anthemis L. In: Güner, A., Aslan, S., Ekim, T., Vural, M., Babac¸ M. T. (eds.). List of Turkish Flora (Vascular Plants)-Türkiye Bitkileri Listesi (Damarlı Bitkiler). Nezahat Gökyigit Botanik Bahcesi ve Flora Arastırmaları Dernegi Yayını. Istanbul, 114-115.
29. Ozturk, B., Ozek, G., Ozek, T. and Baser, K.H.C. (2014). Chemical Diversity in Volatiles of Helichrysum plicatum DC. Subspecies in Turkey, Rec. Nat. Prod. 8(4), 373-384.
30. Pavlovic, M., Kovacevic, N., Couladis, M. and Tzakou, O. (2006). Phenolic constituents of Anthemis triumfetti (L.) DC., Biochem Syst Ecol., 34, 449-452.
31. Pavlovic, M., Lakusic, D., Kovacevic, N., Tzakou, O. and Couladis, M. (2010). Comparative Analysis of Essential Oils of Six Anthemis Taxa from Serbia and Montenegro, Chemistry & Biodiversity, 7, 1231-1244.
32. Riccobono, L., Maggio, A., Bruno, M., Spadaro, V. and F.M. Raimondo, F.M. (2017). Chemical composition and antimicrobial activity of the essential oils of some species of Anthemis sect. Anthemis (Asteraceae) from Sicily. Natural Product Research, 31(23), 2759-2767.
33. Stojkovic, N., Stojkovic, M., Marinkovic, M., Chopra, G., Kostic, D. and Zarubica, A. (2014). Polyphenol Content and Antıoxidant Activity of Anthemis cretica L. (Asteraceae). Oxidation Communıcatıons, 37 (1): 237-246.
34. Tawaha, K.A., Alali, F.Q. and Hudaib, M.M. (2015). Chemical Composition and General Cytotoxicity Evaluation of Essential Oil from the Flowers of Anthemis palestina Reut. ex Boiss., Growing in Jordan, Journal of Essential Oil Bearing Plants 18 (5), 1070-1077.
35. Ugurlu E. and Secmen, O. (2008). Medicinal plants popularly used in the villages of Yunt Mountain (Manisa-Turkey), Fitoterapia, 79, 126-131.
36. Uzel, A., Guvensen, A. and Cetin, E. (2004). Chemical composition and antimicrobial activity of the essential oils of Anthemis xylopoda O. Schwarz from Turkey, J Ethnopharm., 95, 151-154.
37. Vajs, V., Bulatovic, V., Fodulovic-Savikin, K., Menkovic, N., Macura, S., Juranic, N. and S. Milosavljevic, S. (1999). Highly oxygenated guaianolides from Anthemis cretica subsp. cretica. Phytochemistry, 50, 287-291.
38. Venditti, A., Frezza, C., Rossi, G., Di Cecco, M., Ciaschetti, G., Serafini, M. and Bianco, A. (2016). Secodary Metabolites with Ecologic and Medicinal Implications in Anthemis cretica subsp. petraea from Majella National Park, AIMS Molecular Science, 3 (4), 448-660.
39. Yusufoglu, H.S., Tabanca, N., Bernier, U.R., Li, A.Y., Salkini, M.A., Alqasoumi, S.I. and , Demirci, B. (2018). Mosquito and tick repellency of two Anthemis essential oils from Saudi Arabia, Saudi Pharmaceutical Journal 26, 860–864.