Composition and Acetylcholinesterase inhibition properties of Tripleurospermum inodorum (L.) Sch. Bip. Essential Oil from Istanbul
Composition and Acetylcholinesterase inhibition properties of Tripleurospermum inodorum (L.) Sch. Bip. Essential Oil from Istanbul
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-distillationusing a Clevenger type apparatus with 0.03, 0.02 and 0.01% (v/w) yields, respectively. Essential oil composition ofthe oils was determined by GC-MS analyses. Total of ninety compounds were identified in flower oil comprising of80.7% 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 acetone3.8% and salvia-4(14)-en-1-one 3.5% compounds with high relative percentages. Stem essential oil comprised oftwenty-eight compounds representing 87.2% of the oil. The main components of the stem essential oil were wereneryl acetate 12.8%, (E)-β-farnesene 12.5%, phytol 12.1%, guaia-6,10(14)-dien-4β-ol 10.8%, γ-cadinol 7.8%, nonacosane7.3%, decanoic acid 6.3% and caryophyllene oxide 4.6%. In vitro AchE inhition of the oils were evaluated by theEllman spectrophotometric method. AChE inhibitory property was investigated for the flower oil with at four differentconcentrations. 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 theassay. Activity of the essential oil was concentration dependent.
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- 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.