Phytochemical composition and pharmacological activities of Teucrium polium L.
collected from eastern Turkey

ISCAN, GOKALP; KURKCUOGLU, MINE; Göger, Fatih; ecevit genç, gülay; taskin, turgut; Gulsoy Toplan, Gizem; Baser, Kemal Husnu Can; Mat, Afife; CIVAS, AYSE

doi:10.3906/kim-2107-13

Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey

Gizem GULSOY TOPLAN, (İstanbul Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, İstanbul, Türkiye)

Fatih GÖGER, (Anadolu Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, Eskişehir, Türkiye)

Turgut TAŞKIN, (Marmara Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, İstanbul, Türkiye)

Gülay ECEVİT GENÇ, (İstanbul Üniversitesi, Eczacılık Fakültesi, Farmasötik Botanik Anabilim Dalı, İstanbul, Türkiye)

Ayşe CİVAŞ, (Iğdır Üniversitesi, Tuzluca Meslek Yüksekokulu, Eczacılık Hizmetleri Anabilim Dalı, Iğdır, Türkiye.)

Gökalp İŞCAN, (Anadolu Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, Eskişehir, Türkiye)

Mine KURKCUOGLU, (Anadolu Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, Eskişehir, Türkiye)

Afife MAT, (İstanbul Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, İstanbul, Türkiye)

K. Husnu Can BASER (Yakın Doğu Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, Lefkoşa, K.K.T.C)

Turkish Journal of Chemistry

7 0

Yıl: 2022 Cilt: 46 Sayı: 1 Sayfa Aralığı: 269 - 282 Metin Dili: İngilizce DOI: 10.3906/kim-2107-13 İndeks Tarihi: 05-07-2022

Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey

Öz:

Teucrium species that belong to the family Lamiaceae have been traditionally used for their medicinal properties. T. polium is one the most widespread members of the genus for its use in the treatment of several diseases. In this study, the essential oil and phenolic composition of the aerial parts from T. polium were assessed by GC-FID, GC/MS, and LC-MS/MS as well as for its total phenolic content. Several extracts such as n-hexane, chloroform, methanol, and infusion were prepared and their antimicrobial, antioxidant, and also acetylcholinesterase activities were studied. According to GC/MS results, ß -caryophyllene (8.8%), t-cadinol (6.2%), (E)-nerolidol (5%), α -cadinol (5.4%), and a-pinene (4.7%) were identified as main constituents of the essential oil. LC MS/MS analysis of the infusion and the methanol extract showed the presence of 15 phenolic compounds. Moreover, the total phenolic content of each sample was also determined and the infusion had the highest percentage of phenolics. To evaluate the antioxidant properties, the samples were tested by using DPPH” free radical scavenging, FRAP, and CUPRAC activity methods. The infusion showed the strongest radical scavenging activity, whereas n-hexane and chloroform extracts exhibited considerable reducing power effects. The MIC values for all of the examined microorganisms ranged from 15 to 2000 µg/mL with respect to antimicrobial activities.

Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. Edris AE. Pharmaceutical and therapeutic potentials of essential oils and their individual volatile constituents: a review. Phytotherapy Research 2007; 21 (4): 308-323. doi: 10.1002/ptr.2072
2. Sharma K, Guleria S, Razdan VK, Babu V. Synergistic antioxidant and antimicrobial activities of essential oils of some selected medicinal plants in combination and with synthetic compounds. Industrial Crops and Products 2020; 154: 112569. doi: 10.1016/j.indcrop.2020.112569
3. Toplan GG, Kurkcuoglu M, Goger F, İşcan G, Ağalar HG et al. Composition and biological activities of Salvia veneris Hedge growing in Cyprus. Industrial Crops and Products 2017; 97: 41-48. doi: 10.1016/j.indcrop.2016.11.055
4. Zengin G, Llorent-Martínez EJ, Fernández-de Córdova ML, Bahadori MB, Mocan A et al. Chemical composition and biological activities of extracts from three Salvia species: S. blepharochlaena, S. euphratica var. leiocalycina, and S. verticillata subsp. amasiaca. Industrial Crops and Products 2018; 111: 11-21. doi: 10.1016/j.indcrop.2017.09.065
5. Ecevit-Genç G, Özcan T, Dirmenci T. Nutlet and leaf micromorphology in some Turkish species of Teucrium L. (Lamiaceae). Phytotaxa 2017; 312 (1): 71-82. doi: 10.11646/phytotaxa.312.1.5
6. Khazaei M, Nematollahi-Mahani SN, Mokhtari T, Sheikhbahaei F. Review on Teucrium polium biological activities and medical characteristics against different pathologic situations. Journal of Contemporary Medical Sciences 2018; 4 (1): 1-6.
7. Aksoy-Sagirli P, Ozsoy N, Ecevit-Genc G, Melikoglu G. In vitro antioxidant activity, cyclooxygenase-2, thioredoxin reductase inhibition and DNA protection properties of Teucrium sandrasicum L. Industrial Crops and Products 2015; 74: 545-550. doi: 10.1016/j. indcrop.2015.05.025
8. Djabou N, Lorenzi V, Guinoiseau E, Andreani S, Giuliani MC et al. Phytochemical composition of Corsican Teucrium essential oils and antibacterial activity against foodborne or toxi-infectious pathogens. Food Control 2013; 30 (1): 354-363. doi: 10.1016/j. foodcont.2012.06.025
9. Hasani-Ranjbar S, Nayebi N, Larijani B, Abdollahi M. A systematic review of the efficacy and safety of Teucrium species; from anti-oxidant to anti-diabetic effects. IJP-International Journal of Pharmacology 2010; 6 (4): 315-325. doi: 10.3923/ijp.2010.315.325
10. Ruiters AK, Tilney PM, Van Vuuren SF, Viljoen AM, Kamatou GP, et al. The anatomy, ethnobotany, antimicrobial activity and essential oil composition of southern African species of Teucrium (Lamiaceae). South African Journal of Botany 2016; 102: 175-185. doi: 10.1016/j. sajb.2015.06.008
11. Stankovic MS, Niciforovic N, Mihailovic V, Topuzovic M, Solujic S. Antioxidant activity, total phenolic content and flavonoid concentrations of different plant parts of Teucrium polium L. subsp. polium. Acta Societatis Botanicorum Poloniae 2012; 81 (2). doi: 10.5586/asbp.2012.010
12. Hammami S, Jmii H, Mokni RE, Khmiri A, Faidi K et al. Essential oil composition, antioxidant, cytotoxic and antiviral activities of Teucrium pseudochamaepitys growing spontaneously in Tunisia. Molecules 2015; 20 (11): 20426-20433. doi: 10.3390/molecules201119707
13. Jaradat NA. Review of the taxonomy, ethnobotany, phytochemistry, phytotherapy and phytotoxicity of germander plant (Teucrium polium L.). Medicine 2015; 3: 4. https://innovareacademics.in/journals/index.php/ajpcr/article/view/4058
14. Bahramikia S, Yazdanparast R. Phytochemistry and medicinal properties of Teucrium polium L. (Lamiaceae). Phytotherapy Research 2012; 26: 1581-1593. doi: 10.1002/ptr.4617
15. De Marino S, Festa C, Zollo F, Incollingo F, Raimo G et al. Antioxidant activity of phenolic and phenylethanoid glycosides from Teucrium polium L. Food Chemistry 2012; 133 (1): 21-28. doi: 10.1016/j.foodchem.2011.12.054
16. Kaska A, Çiçek M, Mammadov R. Biological activities, phenolic constituents and mineral element analysis of two endemic medicinal plants from Turkey: Nepeta italica subsp. cadmea and Teucrium sandrasicum. South African Journal of Botany 2019; 124: 63-70. doi: 10.1016/j.sajb.2019.04.037
17. Sharififar F, Dehghn-Nudeh G, Mirtajaldini M. Major flavonoids with antioxidant activity from Teucrium polium L. Food Chemistry 2009; 112 (4): 885-888. doi: 10.1016/j.foodchem.2008.06.064
18. Venditti A, Frezza C, Trancanella E, Zadeh SMM, Foddai S et al. A new natural neo-clerodane from Teucrium polium L. collected in Northern Iran. Industrial Crops and Products 2017; 97: 632-638. doi: 10.1016/j.indcrop.2017.01.010
19. Frezza C, Venditti A, Matrone G, Serafini I, Foddai S et al. Iridoid glycosides and polyphenolic compounds from Teucrium chamaedrys L. Natural Product Research 2018; 32 (13): 1583-1589. doi: 10.1080/14786419.2017.1392948
20. Baser KHC, Demircakmak B, Duman H. Composition of the essential oils of three Teucrium species from Turkey. Journal of Essential Oil Research 1997; 9 (5): 545-549. doi: 10.1080/10412905.1997.9700774
21. Baser KHC, Kirimer N. Essential oils of anatolian lamiaceae-An update. Natural Volatiles and Essential Oils 2018; 5 (4): 1-28.
22. Cozzani S, Muselli A, Desjobert JM, Bernardini AF, Tomi F et al. Chemical composition of essential oil of Teucrium polium subsp. capitatum from Corsica. Flavour and Fragrance Journal 2005; 20 (4): 436-441. doi: 10.1002/ffj.1463
23. Özek G, Özek T, Dinç M, Doğu S, Baser KHC. Chemical Diversity of Volatiles of Teucrium orientale L. var. orientale, var. puberulens, and var. glabrescens Determined by Simultaneous GC‐FID and GC/MS Techniques. Chemistry & Biodiversity 2012; 9 (6): 1144-1154. doi: 10.1002/cbdv.201100264
24. Acquaviva R, Genovese C, Amodeo A, Tomasello B, Malfa G et al. Biological activities of Teucrium flavum L., Teucrium fruticans L., and Teucrium siculum Rafin crude extracts. Plant Biosystems 2018; 152 (4): 720-727. doi: 10.1080/11263504.2017.1330773
25. Hajlaoui H, Mighri H, Aouni M, Gharsallah N, Kadri A. Chemical composition and in vitro evaluation of antioxidant, antimicrobial, cytotoxicity and anti-acetylcholinesterase properties of Tunisian Origanum majorana L. essential oil. Microbial Pathogenesis 2016; 95: 86-94. doi: 10.1016/j.micpath.2016.03.003
26. Orhan DD, Özçelik B, Özgen S, Ergun F. Antibacterial, antifungal, and antiviral activities of some flavonoids. Microbiological Research 2010; 165 (6): 496-504. doi: 10.1016/j.micres.2009.09.002
27. Baytop, T., 1999. Therapy with Medicinal Plants in Turkey, Past and Present, 2nd ed. Nobel Medical Publishing, Istanbul, pp. 142–144. 28. European Pharmacopoeia. 2007. (7th ed.,) Vol. 1, Strasbourg: Council of Europe.
29. Ozsoy N, Can A, Yanardağ R, Akev N. Antioxidant activity of Smilax excelsa L. leaf extracts. Food Chemistry 2008; 110 (3): 571-583. doi: 10.1016/j.foodchem.2008.02.037
30. Apak R, Güçlü K, Özyürek M, Karademir SE. Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method”. Journal of Agricultural and Food Chemistry 2004; 52 (26): 7970-7981. doi: 10.1021/jf048741x
31. Wei F, Jinglou C, Yaling C, Yongfang L, Liming C et al. Antioxidant, free radical scavenging, anti-inflammatoryand hepatoprotective potential of the extract from Parathelypteris nipponica (Franch.etSav.) Ching. Journal of Ethnopharmacology 2010; 130 (3): 521-28. doi: 10.1016/j. jep.2010.05.039
32. Benzie IFF, Strain JJ. The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Analytical Biochemistry 1996; 239: 70-76. doi: 10.1006/abio.1996.0292
33. Ellman GL, Courtney KD, Andress V, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology 1961; 7 (2): 88-95. doi: 10.1016/0006-2952(61)90145-9
34. CLSI (NCCLS) M27-A2, 2002. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved Standard— Second Edition.
35. CLSI (NCCLS) M7-A7, 2006. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard, Seventh Edition.
36. Işcan G. Antibacterial and Anticandidal Activities of common Essential Oil Constituents. Records of Natural Products 2017; 11 (4): 374-388.
37. Aburjai T, Hudaib M, Cavrini V. Composition of the essential oil from Jordanian germander (Teucrium polium L.). Journal of Essential Oil Research 2006; 18 (1): 97-99. doi: 10.1080/10412905.2006.9699398.
38. Bakari S, Ncir M, Felhi S, Hajlaoui H, Saoudi M et al. Chemical composition and in vitro evaluation of total phenolic, flavonoid, and antioxidant properties of essential oil and solvent extract from the aerial parts of Teucrium polium grown in Tunisia. Food Science and Biotechnology 2015; 24 (6): 1943-1949. doi: 10.1007/s10068-015-0256-z
39. Mahmoodi R, Kazeminia M, Kabodari A. Review on composition and antimicrobial effects of Teucrium (Teucrium polium L.) grown in Iran and comparison with the around the world. Journal of Babol University of Medical Sciences 2017; 19 (2): 54-64. doi: 10.22088/jbums.19.2.54
40. Cakir A, Duru ME, Harmandar M, Ciriminna R, Passannanti S. Volatile constituents of Teucrium polium L. from Turkey. Journal of Essential Oil Research 1998; 10 (1), 113-115. doi: 10.1080/10412905.1998.9700855
41. Sevindik E, Abacı ZT, Yamaner C, Ayvaz M. Determination of the chemical composition and antimicrobial activity of the essential oils of Teucrium polium and Achillea millefolium grown under North Anatolian ecological conditions. Biotechnology & Biotechnological Equipment 2016; 30 (2): 375-380. doi: 10.1080/13102818.2015.1131626
42. Kurtoğlu C, Tin B. Essential oil composition of Teucrium polium L. Grown in Aydın/Turkey. Turkish Journal of Life Sciences 2017; 2 (1): 142-144.
43. Farahbakhsh J, Najafian S, Hosseinifarahi M, Gholipour S. Essential Oil Composition and Phytochemical Properties from Leaves of Felty Germander (Teucrium polium L.) and Spearmint (Mentha spicata L. Journal of Essential Oil-Bearing Plants 2021, 24(1): 147-159. doi: 10.1080/0972060X.2021.1896976
44. Touaibia M, Abdelali D, Elmaizi FR, Saidi F. Phytochemical characterization and evaluation of some biological activities of felty germander essential oil: Teucrium polium L. (LAMIACEAE). Rhazes: Green and Applied Chemistry 2021, 11: 96-107.
45. Clifford MN, Johnston KL, Knight S, Kuhnert N. Hierarchical scheme for LC-MS Identification of chlorogenic acids. Journal of Agricultural and Food Chemistry 2003; 51 (10): 2900-2911. doi: 10.1021/jf026187q
46. Göğer F, Kaya A, Dinc M, Doğu S. Phenolic compounds determination and antioxidant activity of Teucrium cavernarum. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi-C Yaşam Bilimleri ve Biyoteknoloji 2019; 8 (2): 229-237. doi: 10.18036/estubtdc.599094
47. Mitreski I, Stanoeva JP, Stefova M, Stefkov G, Kulevanova S. Polyphenols in Representative Teucrium Species in the Flora of R. Macedonia: LC/DAD/ESI-MS n Profile and Content. Natural Product Communications 2014; 9 (2): 175-180. doi: 10.1177/1934578X1400900211
48. Özer Z, Kılıç T, Çarıkçı S, Yılmaz H. Investigation of phenolic compounds and antioxidant activity of Teucrium polium L. decoction and infusion. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 2018; 20 (1): 212-218. doi: 10.25092/baunfbed.370594
49. Djordjevic OM, Jakovljevic MR, Markovic A, Stankovic M, Ciric A et al. Polyphenolic contents of Teucrium polium L. and Teucrium scordium L. associated with their protective effects against MMC-induced chromosomal damage in cultured human peripheral blood lymphocytes. Turkish Journal of Biology 2018; 42 (2): 152-162. doi: 10.3906/biy-1707-36
50. Boumerfeg S, Baghiani A, Djarmouni M, Ameni D, Adjadj M et al. Inhibitory activity on xanthine oxidase and antioxidant properties of Teucrium polium L. extracts. Chinese Medicine 2012; 3: 30-41. doi: 10.4236/cm.2012.31006
51. Ljubuncic P, Dakwar S, Portnaya I, Cogan U, Azaizeh H et al. Aqueous extracts of Teucrium polium possess remarkable antioxidant activity in vitro. Evidence-Based Complementary and Alternative Medicine 2006; 3 (3): 329-338. doi: 10.1093/ecam/nel028
52. Panovska TK, Stefova M, Kulevanova S. In vitro antioxidant activity of some Teucrium species (Lamiaceae). Acta Pharmaceutica 2005; 55 (2): 207-214. doi: 10.1016/j.fct.2007.06.020
53. Vladimir-Knežević S, Blažeković B, Kindl M, Vladić J, Lower-Nedza AD et al. Acetylcholinesterase inhibitory, antioxidant and phytochemical properties of selected medicinal plants of the Lamiaceae family. Molecules 2014; 19 (1): 767-782. doi: 10.3390/molecules19010767
54. Orhan I, Aslan M. Appraisal of scopolamine-induced antiamnesic effect in mice and in vitro antiacetylcholinesterase and antioxidant activities of some traditionally used Lamiaceae plants. Journal of Ethnopharmacology 2009; 122 (2), 327-332. doi: 10.1016/j.jep.2008.12.026
55. Ahmad B, Mukarram Shah SM, Khan H, Hassan Shah SM. Enzyme inhibition activities of Teucrium royleanum. Journal of Enzyme Inhibition and Medicinal Chemistry 2007; 22 (6): 730-732. doi: 10.1080/14756360701306271
56. Darabpour E, Motamedi H, Nejad SMS. Antimicrobial properties of Teucrium polium against some clinical pathogens. Asian Pacific Journal of Tropical Medicine 2010; 3 (2): 124-127. doi: 10.1016/S1995-7645(10)60050-8
57. Lograda T, Ramdani M, Chalard P, Figueredo G, Deghar A. Chemical analysis and antimicrobial activity of Teucrium polium L. essential oil from eastern Algeria. American Journal of Advanced Drug Delivery 2014; 2 (6): 697-710.
58. El Atki Y, Aouam I, El Kamari F, Taroq A, Lyoussi B et al. Phytochemistry, antioxidant and antibacterial activities of two Moroccan Teucrium polium L. subspecies: preventive approach against nosocomial infections. Arabian Journal of Chemistry 2020; 13 (2): 3866-3874. doi: 10.1016/j.arabjc.2019.04.001
59. Othman MB, Salah-Fatnassi KBH, Ncibi S, Elaissi A, Zourgui L. Antimicrobial activity of essential oil and aqueous and ethanol extracts of Teucrium polium L. subsp. gabesianum (LH) from Tunisia. Physiology and Molecular Biology of Plants 2017; 23 (3): 723-729. doi: 10.1007/ s12298-017-0444-9
60. Purnavab S, Ketabchi S, Rowshan V. Chemical composition and antibacterial activity of methanolic extract and essential oil of Iranian Teucrium polium against some of phytobacteria. Natural Product Research 2015; 29 (14): 1376-1379. doi: 10.1080/14786419.2014.1000320
61. Shahba S, Bokaeian M, Mozafari SNA, Saeidpour PA, Bameri Z et al. Antibacterial Effect of Teucrium polium on the Bacteria Causing Urinary Tract Infections. Zahedan Journal of Research in Medical Sciences 2014; 16 (3): 44-49.
62. Tusi SK, Jafari A, Marashi SMA, Niknam SF, Farid M et al. Effect of antimicrobial activity of Teucrium polium on oral Streptococcus mutans: a randomized cross-over clinical trial study. BMC Oral Health. 2020; 20: 130. doi: 10.1186/s12903-020-01116-4
63. Babushok VI, Linstrom PJ, Zenkevich IG. Retention indices for frequently reported compounds of plant essential oils. Journal of Physical and Chemical Reference Data 2011; 40 (4): 043101. doi: 10.1063/1.3653552
64. Alan S, Kürkçüoğlu M, Ozek T, Başer KHC. Composition of the essential oils of Calamintha tauricola PH Davis. Journal of Essential Oil Research 2009; 21 (2): 143-145. doi: 10.1080/10412905.2009.9700134
65. Başer KHC, Özek T, Demirci B, Duman H. Composition of the essential oil of Glaucosciadium cordifolium (Boiss.) Burtt et Davis from Turkey. Flavour and Fragrance Journal 2000; 15: 45-46. doi: 10.1002/(SICI)1099-1026(200001/02)15:1<45::AID-FFJ867>3.0.CO;2-L
66. Miyazawa M, Teraniishi A, Ishikawa Y. Components of the Essential Oil from Petasites japonicus. Flavour and Fragrance Journal 2003; 18: 231-233. doi: 10.1002/ffj.1203
67. Padayachee K. 2011. The phytochemistry and biological activities of Athrixia phylicoides. Master Thesis, Univ. Witwatersrand, Johannesburg, South Africa. http://hdl.handle.net/10539/10667
68. Kürkçüoğlu M, İşcan G, Demirci F, Başer KHC, Malyer H et al. Composition and antibacterial activity of the essential oil of Ferulago confusa Velen. Journal of Essential Oil Research 2010; 22 (6): 490-492. doi: 10.1080/10412905.2010.9700380

APA	Gulsoy Toplan G, Göger F, taskin t, ecevit genç g, CIVAS A, ISCAN G, KURKCUOGLU M, Mat A, Baser K (2022). Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey. , 269 - 282. 10.3906/kim-2107-13
Chicago	Gulsoy Toplan Gizem,Göger Fatih,taskin turgut,ecevit genç gülay,CIVAS AYSE,ISCAN GOKALP,KURKCUOGLU MINE,Mat Afife,Baser Kemal Husnu Can Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey. (2022): 269 - 282. 10.3906/kim-2107-13
MLA	Gulsoy Toplan Gizem,Göger Fatih,taskin turgut,ecevit genç gülay,CIVAS AYSE,ISCAN GOKALP,KURKCUOGLU MINE,Mat Afife,Baser Kemal Husnu Can Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey. , 2022, ss.269 - 282. 10.3906/kim-2107-13
AMA	Gulsoy Toplan G,Göger F,taskin t,ecevit genç g,CIVAS A,ISCAN G,KURKCUOGLU M,Mat A,Baser K Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey. . 2022; 269 - 282. 10.3906/kim-2107-13
Vancouver	Gulsoy Toplan G,Göger F,taskin t,ecevit genç g,CIVAS A,ISCAN G,KURKCUOGLU M,Mat A,Baser K Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey. . 2022; 269 - 282. 10.3906/kim-2107-13
IEEE	Gulsoy Toplan G,Göger F,taskin t,ecevit genç g,CIVAS A,ISCAN G,KURKCUOGLU M,Mat A,Baser K "Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey." , ss.269 - 282, 2022. 10.3906/kim-2107-13
ISNAD	Gulsoy Toplan, Gizem vd. "Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey". (2022), 269-282. https://doi.org/10.3906/kim-2107-13

APA	Gulsoy Toplan G, Göger F, taskin t, ecevit genç g, CIVAS A, ISCAN G, KURKCUOGLU M, Mat A, Baser K (2022). Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey. Turkish Journal of Chemistry, 46(1), 269 - 282. 10.3906/kim-2107-13
Chicago	Gulsoy Toplan Gizem,Göger Fatih,taskin turgut,ecevit genç gülay,CIVAS AYSE,ISCAN GOKALP,KURKCUOGLU MINE,Mat Afife,Baser Kemal Husnu Can Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey. Turkish Journal of Chemistry 46, no.1 (2022): 269 - 282. 10.3906/kim-2107-13
MLA	Gulsoy Toplan Gizem,Göger Fatih,taskin turgut,ecevit genç gülay,CIVAS AYSE,ISCAN GOKALP,KURKCUOGLU MINE,Mat Afife,Baser Kemal Husnu Can Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey. Turkish Journal of Chemistry, vol.46, no.1, 2022, ss.269 - 282. 10.3906/kim-2107-13
AMA	Gulsoy Toplan G,Göger F,taskin t,ecevit genç g,CIVAS A,ISCAN G,KURKCUOGLU M,Mat A,Baser K Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey. Turkish Journal of Chemistry. 2022; 46(1): 269 - 282. 10.3906/kim-2107-13
Vancouver	Gulsoy Toplan G,Göger F,taskin t,ecevit genç g,CIVAS A,ISCAN G,KURKCUOGLU M,Mat A,Baser K Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey. Turkish Journal of Chemistry. 2022; 46(1): 269 - 282. 10.3906/kim-2107-13
IEEE	Gulsoy Toplan G,Göger F,taskin t,ecevit genç g,CIVAS A,ISCAN G,KURKCUOGLU M,Mat A,Baser K "Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey." Turkish Journal of Chemistry, 46, ss.269 - 282, 2022. 10.3906/kim-2107-13
ISNAD	Gulsoy Toplan, Gizem vd. "Phytochemical composition and pharmacological activities of Teucrium polium L. collected from eastern Turkey". Turkish Journal of Chemistry 46/1 (2022), 269-282. https://doi.org/10.3906/kim-2107-13