Composition and Acetylcholinesterase inhibition properties of Tripleurospermum inodorum (L.) Sch. Bip. Essential Oil from Istanbul

Year 2018, Volume: 1 Issue: 1, 23 - 38, 30.09.2018

Hüseyin Servi , Yasemin Yücel Yücel Kaan Polatoğlu

Abstract

Abstract: Essential oil composition and Acetylcholinesterase (AChE) inhibition properties of Tripleurospermum inodorum

(L.) Sch. Bip. were investigated. Essential oils of flowers, leaves and stems were obtained through hydro-distillation

using a Clevenger type apparatus with 0.03, 0.02 and 0.01% (v/w) yields, respectively. Essential oil composition of

the oils was determined by GC-MS analyses. Total of ninety compounds were identified in flower oil comprising of

80.7% of the essential oil. The main components of the flower oil were artemisia ketone 14.4%, terpinen-4-ol 5.5%,

1,8-cineole 5.1%, sabinene 4.7% and tricosane 4.6%. Leaf oil was characterized by 35 compounds representing 62.7%

of the oil. Leaf oil contained caryophyllene oxide 16.0%, phytol 12.1%, spathulenol 5.9%, hexahydrofarnesyl acetone

3.8% and salvia-4(14)-en-1-one 3.5% compounds with high relative percentages. Stem essential oil comprised of

twenty-eight compounds representing 87.2% of the oil. The main components of the stem essential oil were were

neryl acetate 12.8%, (E)-β-farnesene 12.5%, phytol 12.1%, guaia-6,10(14)-dien-4β-ol 10.8%, γ-cadinol 7.8%, nonacosane

7.3%, decanoic acid 6.3% and caryophyllene oxide 4.6%. In vitro AchE inhition of the oils were evaluated by the

Ellman spectrophotometric method. AChE inhibitory property was investigated for the flower oil with at four different

concentrations. Highest AChE inhibitory property was observed for 20 mg/mL oil concentration (53.35 ± 1.37 %; n

=3). This AChE inhibitory concentration was equivalent to the activity of 1.26 μg galanthamine hydrobromide in the

assay. Activity of the essential oil was concentration dependent.

Keywords

Tripleurospermum inodorum, Essential oils, AChE inhibition, Artemisia ketone, Caryophyllene oxide, Neryl acetate

References

• Akaydin, G., Şimşek, I., Arituluk, Z. C., & Yeşilada, E. (2013). An ethnobotanical survey in selected towns of the Mediterranean subregion (Turkey). Turkish Journal of Biology, 37(2), 230-247.
• Amiri, M. S., Jabbarzadeh, P., & Akhondi, M. (2012). An ethnobotanical survey of medicinal plants used by indigenous people in Zangelanlo district, Northeast Iran. Journal of Medicinal Plants Research, 6(5), 749-753.
• Bakhtiarian, A., Ejtemaimehr, S., Strobl, S., Pournaghash-Tehrani, S., Partoazar, A., Ghamami, G., & Yasa, N. (2007). Inhibition of carrageenan-induced edema by Tripleurospermum disciforme extract in rats. Pakistan Journal of Biological Sciences: PJBS, 10(13), 2237-2240.
• Bär, B., & Schultze, W. (1996). Composition of the essential oil of the flower heads of Matricaria perforata. Planta Medica, 62(04), 332-335.
• Başer, K. H. C., Özek, T., Demirci, B., & Duman, H. (2000a). Composition of the essential oil of Glaucosciadium cordifolium (Boiss.) Burtt et Davis from Turkey. Flavour and Fragrance Journal, 15(1), 45-46.
• Başer, K. H. C., Tabanca, N., Özek, T., Demirci, B., Duran, A., & Duman, H. (2000b). Composition of the essential oil of Chaerophyllum aksekiense A. Duran et Duman, a recently described endemic from Turkey. Flavour and Fragrance Journal, 15(1), 43-44.
• Başer, K., 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(3), 195-200.
• Başer, K. H. C., Demirci, B., Özek, T., Akalin, E., & Özhatay, N. (2002). Micro-distilled volatile compounds from Ferulago species growing in western Turkey. Pharmaceutical Biology, 40(6), 466-471.
• Başer, K. H. C., Demirci, B., Dekebo, A., & Dagne, E. (2003). Essential oils of some Boswellia spp., myrrh and opopanax. Flavour and Fragrance Journal, 18(2), 153-156.
• Başer, K., Özek, G., Özek, T., Duran, A., & Duman, H. (2006). Composition of the essential oils of Rhabdosciadium oligocarpum (Post ex Boiss.) Hedge et Lamond and Rhabdosciadium microcalycinum Hand.‐Mazz. Flavour and Fragrance Journal, 21(4), 650-655.
• Ćavar Zeljković, S., Ayaz, F. A., Inceer, H., Hayirlioglu-Ayaz, S., & Colak, N. (2015). Evaluation of chemical profile and antioxidant activity of Tripleurospermum insularum, a new species from Turkey. Natural Product Research, 29(3), 293-296.
• Chehregani, A., Mohsenzadeh, F., Mirazi, N., Hajisadeghian, S., & Baghali, Z. (2010). Chemical composition and antibacterial activity of essential oils of Tripleurospermum disciforme in three developmental stages. Pharmaceutical Biology, 48(11), 1280-1284.
• Davis, P. H. (1975). Flora of Turkey and the East Aegean Islands. Vol. 5. Edinburgh: University of Edinburgh Press, 295-311.
• Demirci, B., Başer, K.H.C., Yıldız, B., & Bahçecioğlu, Z. (2003). Composition of the essential oils of six endemic Salvia spp. from Turkey. Flavour and Fragrance Journal, 18(2), 116-121.
• Demirci, B., Başer, K. H. C., & Dadandi, M. Y. (2006). Composition of the Essential Oils of Phlomis rigida Labill. and P. samia L. Journal of Essential Oil Research, 18(3), 328-331.
• Ellman, G. L., Courtney, K. D., Andres Jr, V., & Featherstone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7(2), 88-95.
• Erdoğan, T. F., Gönenç, T. M., Oskay, M. (2013). Antimicrobial and cytotoxic activities of Tripleurospermum parviflorum (Willd.) Pobed. Marmara Pharmaceutical Journal 17,12-14.
• Erdoğan, T. F., Akkol, E. K., Süntar, I., Gönenç, T. M., & Kıvçak, B. (2015). Fatty Acid Compositions and Antiinflammatory Activities of Tripleurospermum parviflorum (Willd.) Pobed. and Tripleurospermum tenuifolium (Kit.). Records of Natural Products, 9(3), 394.
• Fraisse, D., Felgines, C., Texier, O., & Lamaison, J. L. (2011). Caffeoyl derivatives: major antioxidant compounds of some wild herbs of the Asteraceae family. Food and Nutrition Sciences, 2(3), 181.
• Gören, N., Demirci, B., & Başer, K. (2001). Composition of the essential oils of Tanacetum spp. from Turkey. Flavour and Fragrance Journal, 16(3), 191-194.
• Han, M. İ., & Bulut, G. (2015). The folk-medicinal plants of Kadişehri (Yozgat–Turkey). Acta Societatis Botanicorum Poloniae, 84(2), 237.
• Isil, S., Fulya, A., Erdem, Y., Şinasi, Y. (2004). An ethnobotanical survey of the Beypazari, Ayas, and Güdül district towns of Ankara Province (Turkey). Economic Botany, 58(4), 705-720.
• Jaimand, K., & Rezaee, M. B. (2003). Investigation extraction by two different apparatus and effects of essential oils on content and constituents of Tripleurospermum disciforme (CA Mey) Schultz-Bip. In Natural Sciences, 2-7.
• Javidnia, K., Miri, R., Soltani, M., & Khosravi, A. R. (2008). Essential oil composition of Tripleurospermum disciforme from Iran. Chemistry of Natural Compounds, 44(6), 800-801.
• Karamenderes, C., Demirci, B., & Başer, K. H. C. (2008). Composition of essential oils of ten Centaurea L. taxa from Turkey. Journal of Essential oil Research, 20(4), 342-349.
• Kırımer, N., Tabanca, N., Özek, T., Tümen, G., Başer, K.H.C. (2000). Essential oils of Annual Sideritis Species Growing in Turkey. Pharmaceutical Biology, 38(2), 106-111.
• Kıvçak, B., Akay, S., Demirci, B., & Başer, K. (2004). Chemical composition of essential oils from leaves and twigs of Pistacia lentiscus, Pistacia lentiscus var. chia, and Pistacia terebinthus from Turkey. Pharmaceutical Biology, 42(4-5), 360-366.
• Kıyan, H. T., Demirci, B., Başer, K. H. C., & Demirci, F. (2014). The in vivo evaluation of anti-angiogenic effects of Hypericum essential oils using the chorioallantoic membrane assay. Pharmaceutical Biology, 52(1), 44-50.
• Kürkçüoğlu, M., Başer, K., Işcan, G., Malyer, H., & Kaynak, G. (2006). Composition and anticandidal activity of the essential oil of Chaerophyllum byzantinum Boiss. Flavour and Fragrance Journal, 21(1), 115-117.
• Kürkçüoğlu, M., Tosun, F., Inceer, H., & Başer, K. H. C. (2016). Volatile compounds of Tripleurospermum decipiens from different sites in Turkey. Planta Medica, 82(S 01), P718.
• Maggio, A., Rosselli, S., Bruno, M., Spadaro, V., Raimondo, F. M., & Senatore, F. (2012). Chemical composition of essential oil from Italian populations of Artemisia alba Turra (Asteraceae). Molecules, 17(9), 10232-10241.
• Mandegary, A., Soodi, M., Sharififar, F., & Ahmadi, S. (2014). Anticholinesterase, antioxidant, and neuroprotective effects of Tripleurospermum disciforme and Dracocephalum multicaule. Journal of Ayurveda and Integrative Medicine, 5(3), 162.
• Mills, C., Cleary, B. V., Walsh, J. J., & Gilmer, J. F. (2004). Inhibition of acetylcholinesterase by tea tree oil. Journal of Pharmacy and Pharmacology, 56(3), 375-379.
• Minaiyan, M., Ghassemi-Dehkordi, N., & Mohammadzadeh, B. (2007). Anti-ulcer effect of Tripleurospermum disciforme (CA Mey) Shultz Bip on pylorus ligated (Shay) rats. Research in Pharmaceutical Sciences, 1(1), 15-21.
• Mohammadi, H. A., Sajjadi, S. E., Noroozi, M., & Mirhoseini, M. (2016). Collection and assessment of traditional medicinal plants used by the indigenous people of Dastena in Iran. Journal of Herbmed Pharmacology, 5(2), 54-60.
• Naghibi, F., Esmaeili, S., Malekmohammadi, M., Hassanpour, A., & Mosaddegh, M. (2014). Ethnobotanical survey of medicinal plants used traditionally in two villages of Hamedan, Iran. Research Journal of Pharmacognosy, 1(3), 7-14.
• Özüdoğru, B., Akaydın, G., Erik, S., & Yeşilada, E. (2011). Inferences from an ethnobotanical field expedition in the selected locations of Sivas and Yozgat provinces (Turkey). Journal of Ethnopharmacology, 137(1), 85-98.
• Öztürk, E., Özer, H., Çakir, A., Mete, E., Kandemir, A., & Polat, T. (2010). Chemical composition of the essential oil of Tripleurospermum corymbosum E. Hossain, an endemic species from Turkey. Journal of Essential Oil Bearing Plants, 13(2), 148-153.
• Parvini, S., Hosseini, M. J., & Bakhtiarian, A. (2007). The study of analgesic effects and acute toxicity of Tripleurospermum disciforme in rats by formalin test. Toxicology Mechanisms and Methods, 17(9), 575-580.
• Polatoğlu, K., Demirci, F., Demirci, B., Gören, N., & Başer, K. H. C. (2010). Antimicrobial activity and essential oil composition of a new T. argyrophyllum (C. Koch) Tvzel var. argyrophyllum chemotype. Journal of Oleo Science, 59(6), 307-313.
• Polatoğlu, K., Demirci, B., Gören, N., & Başer, K. H. C. (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.
• Polatoğlu, K., Karakoç, Ö. C., & Gören, N. (2013). Phytotoxic, DPPH scavenging, insecticidal activities and essential oil composition of Achillea vermicularis, A. teretifolia and proposed chemotypes of A. biebersteinii (Asteraceae). Industrial Crops and Products, 51, 35-45.
• Polatoğlu, K., Şen, A., Bulut, G., Bitiş, L., & Gören, N. (2014). Essential oil composition of Centaurea kilaea Boiss. and C. cuneifolia Sm. from Turkey. Natural Volatiles & Essential Oils, 1, 55-59.
• Polatoğlu, K., Karakoç, Ö. C., Yücel, Y. Y., Demirci, B., Gören, N., & Başer, K. H. C. (2015). Composition, insecticidal activity and other biological activities of Tanacetum abrotanifolium Druce. essential oil. Industrial Crops and Products, 71, 7-14.
• Polatoğlu, K., Servi, H., Özçınar, Ö., Nalbantsoy, A., & Gücel, S. (2017). Essential Oil Composition of Endemic Arabis purpurea Sm. & Arabis cypria Holmboe (Brassicaceae) from Cyprus. Journal of Oleo Science, 66(1), 65-70.
• Réthy, B., Csupor‐Löffler, B., Zupkó, I., Hajdú, Z., Máthé, I., Hohmann, J., Rédei, T. & Falkay, G. (2007). Antiproliferative activity of Hungarian Asteraceae species against human cancer cell lines. Part I. Phytotherapy Research, 21(12), 1200-1208.
• Sarper, F., Akaydin, G., Şimşek, I., & Yeşilada, E. (2009). An ethnobotanical field survey in the Haymana district of Ankara province in Turkey. Turkish Journal of Biology, 33(1), 79-88.
• Seo, S. M., Kim, J., Kang, J., Koh, S. H., Ahn, Y. J., Kang, K. S., & Park, I. K. (2014). Fumigant toxicity and acetylcholinesterase inhibitory activity of 4 Asteraceae plant essential oils and their constituents against Japanese termite (Reticulitermes speratus Kolbe). Pesticide Biochemistry and Physiology, 113, 55-61.
• Sørensen, N. (1963). Chemical Taxonomy of Acetylenic Compounds. 1st Ed., In Swain, T. (Eds.), Chemical Plant Taxonomy. Academic Press., Elsevier, London, Great Britain, pp. 219-252.
• Souri, E., Sarkhail, P., Kaymanesh, P., Amini, M., & Farsam, H. (2005). Antioxidant Activity of Extract and a New Isolated Dioxaspiran Derivative of Tripleurospermum disciforme. Pharmaceutical Biology, 43(7), 620-623.
• Suleimenov, Y. M., Atazhanova, G. A., Özek, T., Demirci, B., Kulyjasov, A. T., Adekenov, S. M., & Başer, K. H. C. (2001). Essential oil composition of three species of Achillea from Kazakhstan. Chemistry of Natural Compounds, 37(5), 447-450.
• Şimşek, I., Aytekin, F., Yeşilada, E., & Yıldırımlı, Ş. (2004). An ethnobotanical survey of the Beypazari, Ayas, and Güdül district towns of Ankara Province (Turkey). Economic Botany, 58(4), 705-720.
• Tabanca, N., Kırımer, N., Demirci, B., Demirci, F., & Başer, K. H. C. (2001). Composition and antimicrobial activity of the essential oils of Micromeria cristata subsp. phrygia and the enantiomeric distribution of borneol. Journal of Agricultural and Food Chemistry, 49(9), 4300-4303.
• Tabanca, N., Demirci, B., Ozek, T., Kırımer, N., Başer, K.H.C., Bedir, E., Khan, I.A., Wedge, D.E. (2006a). Gas chromatographic–mass spectrometric analysis of essential oils from Pimpinella species gathered from Central and Northern Turkey. Journal of Chromatography A, 1117(2), 194-205.
• Tabanca, N., Demirci, B., Başer, K. H. C., Aytaç, Z., Ekici, M., Khan, S. I., Jacob, M.R. & Wedge, D. E. (2006b). Chemical composition and antifungal activity of Salvia macrochlamys and Salvia recognita essential oils. Journal of Agricultural and Food Chemistry, 54(18), 6593-6597.
• Tabanca, N., Demirci, B., Crockett, S. L., Başer, K. H. C., & Wedge, D. E. (2007). Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils. Journal of Agricultural and Food Chemistry, 55(21), 8430-8435.
• Tetik, F., Civelek, S., & Cakilcioglu, U. (2013). Traditional uses of some medicinal plants in Malatya (Turkey). Journal of Ethnopharmacology, 146(1), 331-346.
• Tunalıer, Z., Kırımer, N., & Başer, K. H. C. (2002). The composition of essential oils from various parts of Juniperus foetidissima. Chemistry of Natural Compounds, 38(1), 43-47.
• Tofighi, Z., Molazem, M., Doostdar, B., Taban, P., Shahverdi, A. R., Samadi, N., & Yassa, N. (2015). Antimicrobial activities of three medicinal plants and investigation of flavonoids of Tripleurospermum disciforme. Iranian Journal of Pharmaceutical Research: IJPR, 14(1), 225.
• Tosun, F., Akyüz Kızılay, Ç., Şener, B., & Vural, M. (2005). The evaluation of plants from Turkey for in vitro. antimycobacterial activity. Pharmaceutical Biology, 43(1), 58-63.
• Tunalıer, Z., Kırımer, N., & Başer, K. H. C. (2003). Wood Essential Oils of Juniperus foeticissima Willd. Holzforschung, 57(2), 140-144.
• Viljoen, A. M., Van Vuuren, S. F., Gwebu, T., Demirci, B., & Başer, K. H. C. (2006). The Geographical Variation and Antimicrobial Activity of African Wormwood (Artemisia afra Jacq.) Essential Oil. Journal of Essential Oil Research, 18, 19-25.
• Williams, C. A., Greenham, J., & Harborne, J. B. (2001). The role of lipophilic and polar flavonoids in the classification of temperate members of the Anthemideae. Biochemical Systematics and Ecology, 29(9), 929-945.
• Yaşar, A., Üçüncü, O., Güleç, C., İnceer, H., Ayaz, S., & Yaylı, N. (2005). GC-MS Analysis of Chloroform Extracts in Flowers, Stems, and Roots of Tripleurospermum callosum. Pharmaceutical Biology, 43(2), 108-112.