Chemical Diversity and Biological Potential of Tanacetum praeteritum subsp. praeteritum Essential Oils

Yıl 2018, Cilt: 5 Sayı: 2, 493 - 510, 01.01.2018

Gülmira Özek

https://doi.org/10.18596/jotcsa.389075

Cited By: 8

Öz

Two samples of Tanacetum
praeteritum (Horwood) Heywood subsp. praeteritum
(Horwood) were collected in flowering period and subjected separately to
hydrodistillation to yield the essential oils (A and B). The oils were
investigated for chemical composition with GC-FID and GC/MS techniques and
evaluated against acetylcholinesterase and a-amylase enzymes and
free radicals (DPPH^• and ABTS^•+) using microtiter plate
assays. Both of the oils were characterized with high abundance of oxygenated
monoterpenes. The oils were distinguished by the main constituents, namely,
camphor (37.6 %), 1,8-cineole (19.5 %) and terpinen-4-ol (9.3 %) were found as
the major constituents in the oil A, while a-thujone (79.4 %) and
b-thujone
(8.5 %) were detected in the oil B. The oils demonstrated significant
inhibitory (80 % and 60.0 %) potentials on acetylcholinesterase (an IC₅₀
of 0.74 mg/mL and an IC₅₀ of 1.78 mg/mL, respectively) which
involved into Alzheimer’s disease. With respect to antidiabetic activity, the
oils demonstrated significant inhibiting potential on porcine pancreatic a-amylase
(an IC₅₀ of 1.02 mg/mL and an IC₅₀ of 0.89 mg/mL) in I₂/KI
assay. The oils demonstrated weak free radical scavenging activity against DPPH
radicals and moderate activity (0.23 mM and 0.15 mM) against ABTS^+•
in TEAC assay.

Anahtar Kelimeler

Tanacetum; oil; chemical composition; GC/MS; activity

Kaynakça

• Referrence 27. Brand-Williams W, Cuvelier ME, Berset CLWT. Use of a free radical method to evaluate antioxidant activity. LWT-Food science and Technology. 1995;28(1):25-30. DOI: 10.1016/S0023-6438(95)80008-5.
• Referrence 10. Ozbilgin S, Akkol EK, Ergene Oz B, Ilhan M, Saltan G, Bahadir Acikara O, et al. In vivo activity assessment of some Tanacetum species used as traditional wound healer along with identification of the phytochemical profile by a new validated HPLC method. Iranian Journal of Basic Medical Sciences. 2018;21(2):145-52. DOI: 10.22038/ijbms.2018.24258.6055.
• Referrence 28. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free radical biology and medicine. 1999;26(9):1231-7.
• Referrence 29. Orav A. Identification of terpenes by gas chromatography-mass spectrometry. In: Niessen WMA, editor. Current Practice of Gas-Chromatography Mass-Spectrometry Chromatographic Science Series. 86. Basel, Switzerland: Marcel Dekker AG; 2001. p. 483-94. ISBN: 0-8247-0473-8.
• Referrence 2. Bączek KB, Kosakowska O, Przybył JL, Pióro-Jabrucka E, Costa R, Mondello L, et al. Antibacterial and antioxidant activity of essential oils and extracts from costmary (Tanacetum balsamita L.) and tansy (Tanacetum vulgare L.). Industrial Crops and Products. 2017;102:154-63. DOI: 10.1016/j.indcrop.2017.03.009.
• Referrence 30. Maggio A, Rosselli S, Bruno M, Spadaro V, Raimondo FM, Senatore F. Chemical composition of essential oil from Italian populations of Artemisia alba Turra (Asteraceae). Molecules. 2012;17(9):10232-41. DOI: 10.3390/molecules170910232.
• Referrence 31. Cha J-D, Jeong M-R, Jeong S-I, Moon S-E, Kim J-Y, Kil B-S, et al. Chemical composition and antimicrobial activity of the essential oils of Artemisia scoparia and A. capillaris. Planta medica. 2005;71(02):186-90. DOI: 10.1055/s-2005-837790.
• Referrence 32. Noorizadeh H, Farmany A, Noorizadeh M. Application of GA-PLS and GA-KPLS calculations for the prediction of the retention indices of essential oils. Química Nova. 2011;34(8):1398-404. DOI: 10.1590/S0100-40422011000800019
• Referrence 33. Bignell C, Dunlop P, Brophy J. Volatile leaf oils of some south‐western and southern Australian species of the genus Eucalyptus (series 1). Part XIX. Flavour and Fragrance Journal. 1998;13(2):131-9. DOI: 10.1002/(SICI)1099-1026(199803/04)13:2<131::AID-FFJ710>3.0.CO;2-X.
• Referrence 34. López MD, Campoy FJ, Pascual-Villalobos MJ, Muñoz-Delgado E, Vidal CJ. Acetylcholinesterase activity of electric eel is increased or decreased by selected monoterpenoids and phenylpropanoids in a concentration-dependent manner. Chem Biol Interact. 2015;229:36-43. DOI: 10.1016/j.cbi.2015.01.006.
• Referrence 19. Gören N, Demirci B, Başer KHC. Composition of the essential oils of Tanacetum spp. from Turkey. Flavour and Fragrance Journal. 2001;16(3):191-4. DOI: 10.1002/ffj.976.
• Referrence 35. Bader A, Panizzi L, Cioni PL, Flamini G. Achillea ligustica: composition and antimicrobial activity of essential oils from the leaves, flowers and some pure constituents. Central European Journal of Biology. 2007;2(2):206-12. DOI: 10.2478/s11535-007-0020-3.
• Referrence 36. Chéraif I, Jannet HB, Hammami M, Khouja M, Mighri Z. Chemical composition and antimicrobial activity of essential oils of Cupressus arizonica Greene. Biochemical Systematics and Ecology. 2007;35(12):813-20. DOI: 10.1016/j.bse.2007.05.009.
• Referrence 11. Adekenov S. Sesquiterpene lactones with unusual structure. Their biogenesis and biological activity. Fitoterapia. 2017;121:16-30. DOI: 10.1016/j.fitote.2017.05.017.
• Referrence 37. Noorizadeh H, Farmany A. Exploration of linear and nonlinear modeling techniques to predict of retention index of essential oils. Journal of the Chinese Chemical Society. 2010;57(6):1268-77. DOI: 10.1002/jccs.201000188.
• Referrence 8. Tan N, Yazici-Tutunis S, Yesil Y, Demirci B, Tan E. Antibacterial activities and composition of the essential oils of Salvia sericeo-tomentosa varieties. Rec Nat Prod. 2017;11:456-61. https://www.researchgate.net/profile/Nur_Tan/publication/317586859_Antibacterial_Activities_and_Composition_of_the_Essential_Oils_of_Salvia_sericeo-tomentosa_Varieties/links/59953dd2a6fdccaded254477/Antibacterial-Activities-and-Composition-of-the-Essential-Oils-of-Salvia-sericeo-tomentosa-Varieties.pdf
• Referrence 39. Baser K, Demirci B, Ozek T, Viljoen A, Victor J. Composition of the essential oils of five Coleonema species from South Africa. Journal of Essential Oil Research. 2006;18:26-9. https://www.researchgate.net/profile/K_Husnu_Can_Baser/publication/221716735_Composition_of_the_essential_oils_of_five_Coleonema_species_from_South_Africa/links/0deec52f61e7aeae7e000000.pdf
• Referrence 3. Godinho LS, Aleixo de Carvalho LS, Barbosa de Castro CC, Dias MM, Pinto PdF, Crotti AEM, et al. Anthelmintic activity of crude extract and essential oil of Tanacetum vulgare (Asteraceae) against adult worms of Schistosoma mansoni. The Scientific World Journal. 2014;2014. DOI: 10.1155/2014/460342.
• Referrence 40. Demirci F, Demirci B, Gürbüz I, Yesilada E, Baser KHC. Characterization and biological activity of Achillea teretifolia Willd. and A. nobilis L. subsp. neilreichii (Kerner) Formanek essential oils. Turkish Journal of Biology. 2009;33(2):129-36. DOI: 10.3906/biy-0808-1.
• Referrence 41. Arze JBL, Collin G, Garneau F-X, Jean F-I, Gagnon H. Essential Oils from Bolivia. VI. Lamiaceae: Lepechinia graveolens (Reg.) Epling L. floribunda (Benth.) Epling, and L. meyeni (Walp.) Epling. Journal of Essential Oil Research. 2009;21(1):36-40. DOI: 10.1080/10412905.2009.9700102.
• Referrence 42. Nam AM, Tomi F, Gibernau M, Casanova J, Bighelli A. Composition and chemical variability of the needle oil from Pinus halepensis growing in Corsica. Chem Biodivers. 2016;13(4):380-6. DOI: 10.1002/cbdv.201500097.
• Referrence 1. Grierson AJC. Tanacetum L. (emend. Briq.). In: Davis PH, editor. Flora of Turkey and The East Aegean Islands. 5. Edinburg: Edinburgh University Press; 1975. p. 256-92 0852245599.
• Referrence 43. Lopes-Lutz D, Alviano DS, Alviano CS, Kolodziejczyk PP. Screening of chemical composition, antimicrobial and antioxidant activities of Artemisia essential oils. Phytochemistry. 2008;69(8):1732-8. DOI: 10.1016/j.phytochem.2008.02.014.
• Referrence 44. Collin G. Aromas from Quebec. IV. Chemical composition of the essential oil of Ledum groenlandicum: A review. American Journal of Essential Oils and Natural Products. 2015;2(3):06-11. http://www.essencejournal.com/pdf/2015/vol2issue3/PartA/2-3-1-642.pdf
• Referrence 45. Fang Y, Qian M. Aroma compounds in Oregon Pinot Noir wine determined by aroma extract dilution analysis (AEDA). Flavour and Fragrance Journal. 2005;20(1):22-9. DOI: 10.1002/ffj.1551.
• Referrence 12. Carocho M, Ferreira IC. A review on antioxidants, prooxidants and related controversy: natural and synthetic compounds, screening and analysis methodologies and future perspectives. Food and Chemical Toxicology. 2013;51:15-25. DOI: 10.1016/j.fct.2012.09.021.
• Referrence 46. Kurose K, Okamura D, Yatagai M. Composition of the essential oils from the leaves of nine Pinus species and the cones of three of Pinus species. Flavour and fragrance journal. 2007;22(1):10-20. DOI: 10.1002/ffj.1609.
• Referrence 47. Tabanca N, Avonto C, Wang M, Parcher JF, Ali A, Demirci B, et al. Comparative investigation of Umbellularia californica and Laurus nobilis leaf essential oils and identification of constituents active against Aedes aegypti. J Agric Food Chem. 2013;61(50):12283-91. DOI: 10.1021/jf4052682.
• Referrence 48. Perry PL, Wang Y, Lin J. Analysis of honeydew melon (Cucumis melo var. inodorus) flavour and GC–MS/MS identification of (E, Z)‐2, 6‐nonadienyl acetate. Flavour and fragrance journal. 2009;24(6):341-7. DOI: 10.1002/ffj.1947.
• Referrence 49. Baser KHC, Demirci B, Iscan G, Hashimoto T, Demirci F, Noma Y, et al. The essential oil constituents and antimicrobial activity of Anthemis aciphylla Boiss. var. discoidea Boiss. Chem Pharm Bull. 2006;54(2):222-5. DOI: 10.1248/cpb.54.222.
• Referrence 4. Haider SZ, Mohan M, Pandey AK, Singh P. Use of Tanacetum tomentosum and Ta. dolichophyllum essential oils as botanical repellents and insecticidal agents against storage pest Tribolium castaneum (Coleoptera: Tenebrionidae). Entomological Research. 2017;47(5):318-27. DOI: 10.1111/1748-5967.12228.
• Referrence 50. Öztürk B, Özek G, Özek T, Baser KHC. Chemical diversity in volatiles of Helichrysum plicatum DC. subspecies in Turkey. Records of Natural Products. 2014;8(4):373. https://search.proquest.com/docview/1803516486?pq-origsite=gscholar
• Referrence 20. EDQM. Determination of Essential Oils in Herbal Drugs 9th ed. Europe Co, editor. Strasbourg: European Directorate for the Quality of Medicines and Healthcare; 2017. 285-6 p. ISBN: 9789999135610.
• Referrence 51. Bousbia N, Vian MA, Ferhat MA, Petitcolas E, Meklati BY, Chemat F. Comparison of two isolation methods for essential oil from rosemary leaves: Hydrodistillation and microwave hydrodiffusion and gravity. Food Chemistry. 2009;114(1):355-62. DOI: 10.1016/j.foodchem.2008.09.106.
• Referrence 52. Polatoglu K, Demirci F, Demirci B, Gören N, Baser KHC. Antimicrobial activity and essential oil composition of a new T. argyrophyllum (C. Koch) Tvzel var. argyrophyllum chemotype. Journal of Oleo Science. 2010;59(6):307-13. DOI: 10.5650/jos.59.307.
• Referrence 53. Akpulat HA, Tepe B, Sokmen A, Daferera D, Polissiou M. Composition of the essential oils of Tanacetum argyrophyllum (C. Koch) Tvzel. var. argyrophyllum and Tanacetum parthenium (L.) Schultz Bip.(Asteraceae) from Turkey. Biochem Syst Ecol. 2005;33(5):511-6. DOI: 10.1016/j.bse.2004.10.006.
• Referrence 54. Yousefzadi M, Ebrahimi SN, Sonboli A, Miraghasi F, Ghiasi S, Arman M, et al. Cytotoxicity, antimicrobial activity and composition of essential oil from Tanacetum balsamita L. subsp. balsamita. Nat Prod Comm. 2009;4(1):119-22. http://europepmc.org/abstract/med/19370888
• Referrence 13. Pope C, Karanth S, Liu J. Pharmacology and toxicology of cholinesterase inhibitors: uses and misuses of a common mechanism of action. Environmental Toxicology and Pharmacology. 2005;19(3):433-46. DOI: 10.1016/j.etap.2004.12.048.
• Referrence 55. Salamci E, Kordali S, Kotan R, Cakir A, Kaya Y. Chemical compositions, antimicrobial and herbicidal effects of essential oils isolated from Turkish Tanacetum aucheranum and Tanacetum chiliophyllum var. chiliophyllum. Biochem Syst Ecol. 2007;35(9):569-81. DOI: 10.1016/j.bse.2007.03.012.
• Referrence 56. Başer K, Demirci B, Tabanca N, Özek T, Gören N. 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 Fragr J. 2001;16(3):195-200. DOI: 10.1002/ffj.977.
• Referrence 57. Polatoğlu K, Demirci B, Demirci F, Gören N, Başer KHC. Biological activity and essential oil composition of two new Tanacetum chiliophyllum (Fisch. & Mey.) Schultz Bip. var. chiliophyllum chemotypes from Turkey. Ind Crops Prod. 2012;39:97-105. DOI: 10.1016/j.indcrop.2012.02.005.
• Referrence 58. Polatoglu K, Demirci B, Demirci F, Gören N, Baser KHC. The essential oil composition of Tanacetum densum (Labill.) Heywood ssp. eginense Heywood from Turkey. Records of Natural Products. 2012;6(4):402. https://search.proquest.com/docview/1803498378?pq-origsite=gscholar
• Referrence 59. Polatoğlu K, Gören N, Başer KHC, Demirci B. The essential oil composition of Tanacetum densum (Labill.) Heywood ssp. sivasicum Hub.-Mor. & Grierson from Turkey. Journal of Essential Oil Research. 2009;21(3):200-2. DOI: 10.1080/10412905.2009.9700148.
• Referrence 21. Özek G, Ishmuratova M, Tabanca N, Radwan MM, Göger F, Özek T, et al. One‐step multiple component isolation from the oil of Crinitaria tatarica (Less.) Sojak by preparative capillary gas chromatography with characterization by spectroscopic and spectrometric techniques and evaluation of biological activity. Journal of Separation Science. 2012;35(5-6):650-60. DOI: 10.1002/jssc.201100950.
• Referrence 5. Polatoğlu K, Servi H, Yücel YY, Nalbantsoy A. Cytotoxicity and acetylcholinesterase inhibitory and PRAP activities of the essential oils of selected Tanacetum L. species. Natural Volatiles & Essential Oils. 2015;2(4):11-6. http://dergipark.ulakbim.gov.tr/nveo/article/view/5000183084
• Referrence 60. Polatoglu K, Sen A, Kandemir A, Gören N. Essential oil composition and DPPH scavenging activity of endemic Tanacetum mucroniferum Hub.–Mor. & Grierson from Turkey. Journal of Essential Oil Bearing Plants. 2012;15(1):66-74. DOI: 10.1080/0972060X.2012.10644021.
• Referrence 61. Hendriks H, Bos R, Woerdenbag H. The Essential Oil of Tanacetum parthenium (L.) Schultz‐Bip. Flavour and Fragrance Journal. 1996;11(6):367-71. DOI: 10.1002/(SICI)1099-1026(199611)11:6<367::AID-FFJ598>3.0.CO;2-R.
• Referrence 62. Polatoglu K, Demirci F, Demirci B, Gören N, Baser KHC. Antibacterial activity and the variation of Tanacetum parthenium (L.) Schultz Bip. essential oils from Turkey. Journal of oleo science. 2010;59(4):177-84. DOI: 10.5650/jos.59.177.
• Referrence 63. Polatoğlu K, Demirci B, Gören N, Başer KHC. Essential oil composition of endemic Tanacetum zahlbruckneri (Náb.) and Tanacetum tabrisianum (Boiss.) Sosn. and Takht. from Turkey. Natural product research. 2011;25(6):576-84. DOI: 10.1080/14786419.2010.483434.
• Referrence 14. Pan H-J, Lin Y, Chen YE, Vance DE, Leiter EH. Adverse hepatic and cardiac responses to rosiglitazone in a new mouse model of type 2 diabetes: Relation to dysregulated phosphatidylcholine metabolism. Vascular Pharmacology. 2006;45(1):65-71. https://doi.org/10.1016/j.vph.2005.11.011.
• Referrence 64. Dohi S, Terasaki M, Makino M. Acetylcholinesterase inhibitory activity and chemical composition of commercial essential oils. J Agric Food Chem. 2009;57(10):4313-8. DOI: 10.1021/jf804013j.
• Referrence 65. Kaufmann D, Dogra AK, Wink M. Myrtenal inhibits acetylcholinesterase, a known Alzheimer target. J Pharm Pharmacol. 2011;63(10):1368-71. DOI: 10.1111/j.2042-7158.2011.01344.x.
• Referrence 66. Awasthi M, Upadhyay AK, Singh S, Pandey VP, Dwivedi UN. Terpenoids as promising therapeutic molecules against Alzheimer’s disease: amyloid beta-and acetylcholinesterase-directed pharmacokinetic and molecular docking analyses. Molecular Simulation. 2017:1-11. DOI: 10.1080/08927022.2017.1334880.
• Referrence 67. Daradka HM, Abas MM, Mohammad MA, Jaffar MM. Antidiabetic effect of Artemisia absinthium extracts on alloxan-induced diabetic rats. Comparative Clinical Pathology. 2014;23(6):1733-42. DOI: 10.1007/s00580-014-1963-1.
• Referrence 22. Joulain D, König WA, Hochmuth DH. Library of MassFinder-4. In: Hochmuth DH, editor. Terpenoids and Related Constituents of Essential oils. Hamburgh, Germany: Hochmuth Scientific Consulting; 2001. http://massfinder.com/wiki/MassFinder_4.
• Referrence 68. Lachenmeier DW, Walch SG. The choice of thujone as drug for diabetes: Reply to: Al-Haj Baddar et al.(2011). Natural product research. 2011;25(20):1890-2. DOI: 10.1080/14786419.2011.622279.
• Referrence 69. Al-Omari SM. The effect of thujone and myrcene on diabetes mellitus in albino rats. Faculty of Graduate Studies University of Jordan. 2007;Master's Degree of Science in Biological Sciences. https://theses.ju.edu.jo/Original_Abstract/JUF0634949/JUF0634949.pdf.
• Referrence 6. Baddar NWA-H, Aburjai TA, Taha MO, Disi AM. Thujone corrects cholesterol and triglyceride profiles in diabetic rat model. Nat Prod Res. 2011;25(12):1180-4. DOI: 10.1080/14786419.2010.496116.
• Referrence 7. de Almeida LMS, Carvalho LSAd, Gazolla MC, Silva Pinto PL, Silva MPNd, de Moraes J, et al. Flavonoids and sesquiterpene lactones from Artemisia absinthium and Tanacetum parthenium against Schistosoma mansoni worms. Evidence-Based Complementary and Alternative Medicine. 2016;2016:1-9. DOI 10.1155/2016/9521349.
• Referrence 8. Pålsson K, Jaenson TG, Bæckström P, Borg-Karlson A-K. Tick repellent substances in the essential oil of Tanacetum vulgare. Journal of Medical Entomology. 2008;45(1):88-93. DOI: 10.1603/0022-2585(2008)45[88:TRSITE]2.0.CO;2.
• Referrence 9. Coté H, Boucher M-A, Pichette A, Legault J. Anti-inflammatory, antioxidant, antibiotic, and cytotoxic activities of Tanacetum vulgare L. essential oil and its constituents. Medicines. 2017;4(2):34. DOI: 10.3390/medicines4020034.
• Referrence 15. White JA, Hirsch IB. Nonhypoglycemic drug reactions of agents used to treat diabetes. Endocrinology and Metabolism Clinics of North America. 2000;29(4):803-11. DOI: 10.1016/S0889-8529(05)70165-1.
• Referrence 16. Gören N. Flavonoids of Tanacetum praeteritum subsp. praeteritum. Journal of Faculty Pharmacy of Istanbul University. 1994;30:25-30. http://dergipark.gov.tr/download/article-file/5239
• Referrence 17. Gören N. Sesquiterpene lactones from Tanacetum praeteritum. Phytochemistry. 1995;38(5):1261-4. http://dx.doi.org/10.1016/0031-9422(94)00746-G.
• Referrence 18. Gören N. Eudesmane-type sesquiterpenes from Tanacetum praeteritum subsp. praeteritum. Phytochemistry. 1996;42(3):747-9. DOI: 10.1016/0031-9422(95)00933-7.
• 2 Referrence 3. Adams RP. Identification of Essential Oil Components by Gas Chromatography / Mass Spectrometry. 4th ed. Adams RP, editor: Allured Pub Corp.; 2007. 804 p. ISBN: 1932633219.
• Referrence 24. Baser KHC, Demirci F. Flavours and Fragrances.Chemistry of Essential Oils. In: Berger RG, editor. Flavours and Fragrances: Chemistry, Bioprocessing and Sustainability: Springer-Verlag Berlin Heidelberg; 2007. p. 648. ISBN: 978-3-540-49338-9.
• Referrence 25. Ellman GL, Courtney KD, Andres V, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology. 1961;7(2):88IN191-9095. DOI: 10.1016/0006-2952(61)90145-9.
• Referrence 26. Yang XW, Huang MZ, Jin YS, Sun LN, Song Y, Chen HS. Phenolics from Bidens bipinnata and their amylase inhibitory properties. Fitoterapia. 2012;83(7):1169-75. DOI: 10.1016/j.fitote.2012.07.005.