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Assessment of Inhibitory Ability Against Medicinally Important Enzymes with Invitro and In Silico Studies: Phenolic Content of Endemic Centaurea cadmea subsp. pontica

Yıl 2024, , 14 - 25, 28.02.2024

Dursun Kısa , Ahmet Çelik , Rizvan İmamoğlu

https://doi.org/10.18016/ksutarimdoga.vi.1294720

Öz

Centaurea species has great potential as a traditional medicinal herb and C. cadmea subsp. pontica collected from rocky slope crevices of Küre Mountain is endemic to the flora of Türkiye. In the present work, to reveal the plant's pharmacological importance, its potency to inhibit various medicinal enzymes was investigated, supported by molecular docking studies. The half-maximal inhibitory concentration (IC50) results for studied enzymes were quantified between 0.50-86.97 µg mLˉˡ, and the extract was efficient against HMG_CoA R, α-glucosidase, and α-amylase enzymes linked to diabetes and cholesterol. Nine phenolic compounds were identified in the C. cadmea subsp. pontica extract and the interactions of the most abundant phenolic compounds with the enzymes were examined with molecular docking studies. In conclusion, findings amassed from the present study inclined to support the opinion that C. cadmea subsp. pontica may be beneficial as an effective herb for formulating novel health-promoting ingredients.

Anahtar Kelimeler

Centaurea cadmea Enzyme inhibition Molecular docking Phenolic component

Destekleyen Kurum

Bartın University

Proje Numarası

2021-FEN-A-004

Kaynakça

  • Acet, T. (2021). Determining the phenolic components by using HPLC and biological activity of Centaurea triumfetti. Plant Biosyst, 155, 159-164. doi: 10.1080/11263504.2020.1722275.
  • Aktumsek, A., Zengin, G., Guler, G. O., Cakmak, Y. S. & Duran, A. (2013). Antioxidant potentials and anticholinesterase activities of methanolic and aqueous extracts of three endemic Centaurea L. species. Food Chem Toxicol, 55, 290-296. doi: 10.1016/j.fct.2013.01.018.
  • Albayrak, S., Atasagun, B. & Aksoy, A. (2017). Comparison of phenolic components and biological activities of two Centaurea sp. obtained by three extraction techniques. Asian Pac J Trop Med. 10(6), 599-606. doi: 10.1016/j.apjtm.2017.06.010.
  • Alper., M. & Güneş, H. (2019). The Anticancer and Anti-inflammatory Effects of Centaurea solstitialis Extract on Human Cancer Cell Lines. Turk J Pharm Sci, 16(3), 273-281. doi: 10.4274/ tjps.galenos.2018.27146.
  • Alper, M., Özay, C., Güneş, H. & Mammadov, R. (2021). Assessment of Antioxidant and Cytotoxic Activities and Identification of Phenolic Compounds of Centaurea solstitialis and Urospermum picroides from Turkey. Brazilian Arch Biol Technol, 64, 1-12. doi: 10.1590/1678-4324-2021190530.
  • Astari, K.. A., Erel, S. B., Bedir, E. & Karaalp, C. (2013). Secondary Metabolites of Centaurea cadmea Boiss. Rec. Nat. Prod. 7(3), 242-244.
  • Astari, K. A., Baykan, Erel, Ş., Aydin Köse F, Köksal Ç. & Karaalp C. (2014). Cytotoxic and Antibacterial Activities of Centaurea cadmea Boiss. Turkish J Pharm Sci, 11, 101-106.
  • Bancheva, S., Badalamenti, N. & Bruna, M. (2023). The essential oil composition of the endemic plant species Centaurea vandasii and chemotaxonomy of section Phalolepis (Asteraceae). Natural Product Research, 37(7), 1122-1129. https://doi.org/10.1080/ 14786419.2021.1992627.
  • Baskaran G, Salvamani S, Ahmad, S. A., Shaharuddin, N. A., Pattiram, P. D. & Shukor, M. Y. (2015). HMG-CoA reductase inhibitory activity and phytocomponent investigation of Basella alba leaf extract as a treatment for hypercholesterolemia. Drug Des Devel Ther, 9, 509-517. doi: 10.2147/DDDT.S75056.
  • Baydoun, S., Chalak, L., Dalleh, H. & Arnold, N. (2015). Ethnopharmacological survey of medicinal plants used in traditional medicine by the communities of Mount Hermon, Lebanon. J Ethnopharmacol, 173, 139-156. doi: 10.1016/ j.jep.2015.06.052.
  • Boğa, M., Alkan, H., Ertaş, A., Oral, E.V., Yılmaz, M.A., Yeşil, Y., Gören, A.C., Temel, H. & Kolak, U. (2016). Phytochemical profile and some biological activities of three centaurea species from Turkey. Trop J Pharm Res. 15, 1865-1875. doi: 10.4314/ tjpr.v15i9.8.
  • Ćurković-Perica, M., Likić, S. & Rusak, G. (2014). Phenolic compounds in centaurea rupestris tissues and their antiphytoviral activity. Croat Chem Acta, 87, 79-84. doi: 10.5562/cca2272.
  • Dalar, A., Uzun, Y., Mukemre, M., Turker, M. & Konczak, I. (2015). Centaurea karduchorum Boiss. from Eastern Anatolia: Phenolic composition, antioxidant and enzyme inhibitory activities. J Herb Med. 5, 211-216. doi: 10.1016/j.hermed. 2015.09.006.
  • Duman, H., Uzunhisarcıklı, M.E. & Bahadır, Y.N. (2021). A new species of Centaurea (Asteraceae) from northern Turkey. Nordic Journal of Botany, 39(10), 1-8. doi: 10.1111/njb.03244
  • Dutta, T., Anand, U., Saha, S. C., Mane, A.B., Prasanth, D. A., Kandimalla, R., Proćków, J. & Dey, A. (2021). Advancing urban ethnopharmacology: A modern concept of sustainability, conservation and cross-cultural adaptations of medicinal plant lore in the urban environment. Conserv Physiol, 9, 1–20. doi: 10.1093/conphys/coab073.
  • Eberhardt, J., Santos-Martins, D., Tillack, A. F. & Forli, S. (2021). AutoDock Vina 1.2.0: New Docking Methods, Expanded Force Field, and Python Bindings. Chem. Inf. Model. 61(8), 3891-3898.
  • Ellman, G. L., Courtney, K. D., Andres, V. & Featherstone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol, 7, 88-95. doi:10.1016/0006-2952(61)90145-9.
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Tıbbi Açıdan Önemli Enzimlere Karşı İnhibisyon Yeteneğinin Invitro ve Insilico Çalışmalarla Değerlendirilmesi: Endemik Centaurea cadmea subsp. pontica Bitkisinin Fenolik İçeriği

Yıl 2024, , 14 - 25, 28.02.2024

Dursun Kısa , Ahmet Çelik , Rizvan İmamoğlu

https://doi.org/10.18016/ksutarimdoga.vi.1294720

Öz

Centaurea türleri geleneksel şifalı bitki olarak büyük bir potansiyele sahiptir. Küre Dağı'nın kayalık yamaç yarıklarından toplanan C. cadmea subsp. pontica Türkiye florasına endemiktir. Bu çalışmada, bitkinin farmakolojik önemini ortaya koymak için çeşitli tıbbi enzimleri inhibe etme pontansiyeli, moleküler yerleştirme çalışmaları ile desteklenerek araştırılmıştır. Çalışılan enzimler için yarı maksimum inhibitör konsantrasyon (IC50) sonuçları 0.50-86.97 µg mLˉˡ arasında belirlendi. Bitki ekstraktı diyabet ve kolesterol ile bağlantılı olan HMG_CoA R, α-amilaz ve α -glukosidaz enzimlerine karşı etki gösterdi. C. cadmea subsp. pontica özütünde dokuz fenolik bileşik tanımlandı ve en fazla bulunan fenolik bileşiklerin enzimlerle etkileşimleri moleküler yerleştirme çalışmaları ile incelenmiştir. Sonuç olarak, mevcut çalışmadan elde edilen bulgular, bu endemik bitkinin sağlıklı yaşam kalitesinin geliştirilmesine yönelik yeni bileşenlerin formüle edilmesi için etkili bir bitki olarak yararlı olabileceğini göstermektedir.

Anahtar Kelimeler

Centaurea cadmea Enzim inhibisyonu Moleküler kenetlenme Fenolik içerik

Destekleyen Kurum

Scientific Research Projects Unit of Bartın University

Proje Numarası

2021-FEN-A-004

Teşekkür

The present study was financially supported with a research grant coded 2021-FEN-A-004 by the Scientific Research Projects Unit of Bartın University, Türkiye. We are very grateful to Prof. Dr. Zafer Kaya, who identified the plant and passed away from this world.

Kaynakça

  • Acet, T. (2021). Determining the phenolic components by using HPLC and biological activity of Centaurea triumfetti. Plant Biosyst, 155, 159-164. doi: 10.1080/11263504.2020.1722275.
  • Aktumsek, A., Zengin, G., Guler, G. O., Cakmak, Y. S. & Duran, A. (2013). Antioxidant potentials and anticholinesterase activities of methanolic and aqueous extracts of three endemic Centaurea L. species. Food Chem Toxicol, 55, 290-296. doi: 10.1016/j.fct.2013.01.018.
  • Albayrak, S., Atasagun, B. & Aksoy, A. (2017). Comparison of phenolic components and biological activities of two Centaurea sp. obtained by three extraction techniques. Asian Pac J Trop Med. 10(6), 599-606. doi: 10.1016/j.apjtm.2017.06.010.
  • Alper., M. & Güneş, H. (2019). The Anticancer and Anti-inflammatory Effects of Centaurea solstitialis Extract on Human Cancer Cell Lines. Turk J Pharm Sci, 16(3), 273-281. doi: 10.4274/ tjps.galenos.2018.27146.
  • Alper, M., Özay, C., Güneş, H. & Mammadov, R. (2021). Assessment of Antioxidant and Cytotoxic Activities and Identification of Phenolic Compounds of Centaurea solstitialis and Urospermum picroides from Turkey. Brazilian Arch Biol Technol, 64, 1-12. doi: 10.1590/1678-4324-2021190530.
  • Astari, K.. A., Erel, S. B., Bedir, E. & Karaalp, C. (2013). Secondary Metabolites of Centaurea cadmea Boiss. Rec. Nat. Prod. 7(3), 242-244.
  • Astari, K. A., Baykan, Erel, Ş., Aydin Köse F, Köksal Ç. & Karaalp C. (2014). Cytotoxic and Antibacterial Activities of Centaurea cadmea Boiss. Turkish J Pharm Sci, 11, 101-106.
  • Bancheva, S., Badalamenti, N. & Bruna, M. (2023). The essential oil composition of the endemic plant species Centaurea vandasii and chemotaxonomy of section Phalolepis (Asteraceae). Natural Product Research, 37(7), 1122-1129. https://doi.org/10.1080/ 14786419.2021.1992627.
  • Baskaran G, Salvamani S, Ahmad, S. A., Shaharuddin, N. A., Pattiram, P. D. & Shukor, M. Y. (2015). HMG-CoA reductase inhibitory activity and phytocomponent investigation of Basella alba leaf extract as a treatment for hypercholesterolemia. Drug Des Devel Ther, 9, 509-517. doi: 10.2147/DDDT.S75056.
  • Baydoun, S., Chalak, L., Dalleh, H. & Arnold, N. (2015). Ethnopharmacological survey of medicinal plants used in traditional medicine by the communities of Mount Hermon, Lebanon. J Ethnopharmacol, 173, 139-156. doi: 10.1016/ j.jep.2015.06.052.
  • Boğa, M., Alkan, H., Ertaş, A., Oral, E.V., Yılmaz, M.A., Yeşil, Y., Gören, A.C., Temel, H. & Kolak, U. (2016). Phytochemical profile and some biological activities of three centaurea species from Turkey. Trop J Pharm Res. 15, 1865-1875. doi: 10.4314/ tjpr.v15i9.8.
  • Ćurković-Perica, M., Likić, S. & Rusak, G. (2014). Phenolic compounds in centaurea rupestris tissues and their antiphytoviral activity. Croat Chem Acta, 87, 79-84. doi: 10.5562/cca2272.
  • Dalar, A., Uzun, Y., Mukemre, M., Turker, M. & Konczak, I. (2015). Centaurea karduchorum Boiss. from Eastern Anatolia: Phenolic composition, antioxidant and enzyme inhibitory activities. J Herb Med. 5, 211-216. doi: 10.1016/j.hermed. 2015.09.006.
  • Duman, H., Uzunhisarcıklı, M.E. & Bahadır, Y.N. (2021). A new species of Centaurea (Asteraceae) from northern Turkey. Nordic Journal of Botany, 39(10), 1-8. doi: 10.1111/njb.03244
  • Dutta, T., Anand, U., Saha, S. C., Mane, A.B., Prasanth, D. A., Kandimalla, R., Proćków, J. & Dey, A. (2021). Advancing urban ethnopharmacology: A modern concept of sustainability, conservation and cross-cultural adaptations of medicinal plant lore in the urban environment. Conserv Physiol, 9, 1–20. doi: 10.1093/conphys/coab073.
  • Eberhardt, J., Santos-Martins, D., Tillack, A. F. & Forli, S. (2021). AutoDock Vina 1.2.0: New Docking Methods, Expanded Force Field, and Python Bindings. Chem. Inf. Model. 61(8), 3891-3898.
  • Ellman, G. L., Courtney, K. D., Andres, V. & Featherstone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol, 7, 88-95. doi:10.1016/0006-2952(61)90145-9.
  • Elmastaş, M., Demir, A., Genç, N., Dölek, Ü. & Güneş, M. (2017). Changes in flavonoid and phenolic acid contents in some Rosa species during ripening. Food Chem, 235, 154-159. doi: 10.1016/j.foodchem. 2017.05.004.
  • Sönmez, P. & Çakıloğlu, U. (2020). Screening of Antimicrobial Effect against Microorganisms Threatening to Human Health of the Endemic Plant; Centaurea saligna (C. Koch) Wagenitz from Turkey. Türk Doğa ve Fen Derg, 9, 23-27 . doi: 10.46810/tdfd.732234.
  • Gonçalves, S. & Romano, A. (2017). Inhibitory Properties of Phenolic Compounds Against Enzymes Linked with Human Diseases. In: Soto-Hernández M (ed) Phenolic Compounds Biological Activity. IntechOpen, p 228.
  • Gonçalves, S. & Romano, A. (2018). Production of Plant Secondary Metabolites by Using Biotechnological Tools. In: Vijayakumar R (ed) Secondary Metabolites Sources and Applications. IntechOpen, p 138.
  • Grafakou, N. E., Djeddi, S., Tarek, H. & Skaltsa, H. (2018). Secondary metabolites from the aerial parts of Centaurea papposa (Coss.) Greuter. Biochemical Systematics and Ecology, 76, 15-22. https://doi.org/ 10.1016/j.bse.2017.11.005.
  • Guerrero, L., Castillo, J., Quiñones, M., Garcia-Vallvé, S., Arola, L., Pujadas, G. & Muguerza, B. (2012.) Inhibition of Angiotensin-Converting Enzyme Activity by Flavonoids: Structure-Activity Relationship Studies. PLoS One, 7, 1-11. doi: 10.1371/journal.pone.0049493.
  • Holdgate, G. A., Ward, W. H. J. & McTaggart, F. (2003). Molecular mechanism for inhibition of 3-hydroxy-3-methylglutaryl CoA (HMG-CoA) reductase by rosuvastatin. Biochem Soc Trans, 31, 528-531. doi: 10.1042/BST0310528.
  • Hou, W. C., Chen, H. J. & Lin, Y. H. (2003). Antioxidant peptides with angiotensin converting enzyme inhibitory activities and applications for angiotensin converting enzyme purification. J Agric Food Chem, 51, 1706-1709. doi: 10.1021/jf0260242.
  • Ikram, M., Rehman, S., Subhan, F., Akhtar, M. N, & Sinnokrot, M. O. (2017). Synthesis, characterization, thermal degradation and urease inhibitory studies of the new hydrazide based Schiff base ligand 2-(2-hydroxyphenyl)-3-{[(E)-(2-hydroxyphenyl)methylidene]amino}-2,3-dihydroquinazolin-4(1H)-one. Open Chem, 15, 308-319. doi: 10.1515/chem-2017-0035.
  • Karamenderes, C., Khan, S., Tekwani, B. L., Jacob, M. R. & Khan, I. A. (2006). Antiprotozoal and antimicrobial activities of Centaurea species growing in Turkey. Pharm Biol, 44(7), 534-539, doi: 10.1080/13880200600883080.
  • Karamenderes, C., Konyalioglu, S., Khan, S. & Khan, I. A. (2008). Inhibition of cholinesterase and amyloid aggregation by resveratrol oligomers from Vitis amurensis. Phyther Res, 22, 544-549. https://doi.org/10.1002/ptr.2406
  • Köse, Y. B., İşcan, G., Göger, F., Akalın, G., Demirci, B. & Başer, K. H. C. (2016). Chemical Composition and Biological Activity of Centaurea baseri: New Species from Turkey. Chem Biodivers, 13, 1369-1379. doi: 10.1002/CBDV.201600070.
  • Köse, Y. B., Ocak, A. & Erkara, I. P. (2010). Centaurea cadmea subsp. pontica subsp. nov. (Asteraceae) from northwest Anatolia, Turkey. Nord J Bot, 28, 475-478. doi: 10.1111/j.1756-1051.2009.00585.x.
  • Masuda, T., Yamashita, D., Takeda, Y. & Yonemori, S. (2005). Screening for tyrosinase inhibitors among extracts of seashore plants and identification of potent inhibitors from Garcinia subelliptica. Biosci Biotechnol Biochem, 69, 197-201. doi: 10.1271/bbb.69.197.
  • Meng X-Y, Zhang H-X, Mezei M, Cui M (2011) Molecular Docking: A Powerful Approach for Structure-Based Drug Discovery. Curr Comput Aided-Drug Des. 7(2), 146-157. doi: 10.2174/ 157340911795677602
  • Mohamed El-Korany S, Mohamed Helmy O, Mahmoud El-Halawany A, El-Mohammadi Ragab Y, Hafez Zedan H (2020) Kojic acid repurposing as a pancreatic lipase inhibitor and the optimization of its production from a local Aspergillus oryzae soil isolate. BMC Biotechnol, 20, 1-16. doi: 10.1186/ s12896-020-00644-9
  • Morris, G.M. & Dallakyan, S. (2013) AutoDock — AutoDock. 02-27.
  • Naeim, H., El-Hawiet, A., Abdel Rahman, R. A., Hussein, A., El Demellawy, M. A. & Embaby, A. M. (2020). Antibacterial activity of Centaurea pumilio L. Root and aerial part extracts against some multidrug resistant bacteria. BMC Complement Med Ther, 20, 79. doi: 10.1186/s12906-020-2876-y.
  • Özbek, M.U. (2021). Centaurea kirikkalensis (Asteraceae), a new species from Turkey. Nordic Journal of Botany, 39(7), 1-9. e03235, doi: 10.1111/njb.03235.
  • Pękal, A. & Pyrzynska, K. (2014). Evaluation of Aluminium Complexation Reaction for Flavonoid Content Assay. Food Anal Methods, 7, 1776–1782. doi: 10.1007/s12161-014-9814-x.
  • Pettersen, E. F., Goddard, T. D., Huang, C. C., Couch, G. S., Greenblatt, D. M., Meng, E. C. & Ferrin, T. E. (2004). UCSF Chimera - A visualization system for exploratory research and analysis. J Comput Chem, 25(13), 1605-1612 doi: 10.1002/jcc.20084
  • Reda, E. H., Abdel Shakour, Z. T., El-Halawany, A. M., El-Kashoury, E. S. A., Shams, K. A., Mohamed, T. A., Saleh, I., Elshamy, A. I., Atia, M. A. M., El-Beih, A. A., Abdel-Azim, N. S., El-Seedi, H. R. & Hegazy, M. E. F. (2021). Comparative study on the essential oils from five wild egyptian Centaurea species: Effective extraction techniques, antimicrobial activity and in-silico analyses. Antibiotics, 10(3), 1-18. doi: 10.3390/antibiotics10030252
  • Shoeb, M., Jaspars, M., MacManus, S. M., Celik, S., Nahar, L., Kong-Thoo-Lin, P. & Sarker, S. D. (2007). Anti-colon cancer potential of phenolic compounds from the aerial parts of Centaurea gigantea (Asteraceae). J Nat Med, 61, 164-169. doi: 10.1007/s11418-006-0117-4
  • Singleton, V. L. & Rosi, J. A. (1965). Colorimetry of Total Phenolics with Phosphomolybdic-Phosphotungstic Acid Reagents. Am J Oenol Vitic, 16, 144–158.
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  • Tiwana, G., Fua, J., Lu, L., Cheesman, M. J. & Cock, I. E. (2021). A review of the traditional uses, medicinal properties and phytochemistry of Centaurea benedicta l. Pharmacogn J, 13, 798-812. doi: 10.5530/pj.2021.13.102.
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  • Tugay, O., Paşayeva, L., Demirpolat, E. & Şah,n, M. (2021). Comparative Evaluation of Cytotoxicity and Phytochemical Composition of Centaurea iconiensis (Rhaponticoides iconiensis). Iran J Sci Technol Trans Sci, 45, 65-7. https://doi.org/10.1007/s40995-020-01030-y.
  • Yaman, B., Kaya, Z., Tunçkol, B. & Özel, H. (2020). The endemic plants in Bartin, Turkey and their conservation status. Biol Nyssana, 11, 23-29. doi: 10.5281/zenodo.4060285.
  • Yang, X. W., Huang, M. Z., Jin, Y. S., Sun, L. N., Song, Y. & Chen, H. S. (2012.) Phenolics from Bidens bipinnata and their amylase inhibitory properties. Fitoterapia, 83, 1169-1175. doi: 10.1016/ j.fitote.2012.07.005.
  • Yin, B., Fang, D. M., Zhou, X.L. & Gao, F. (2019). Natural products as important tyrosine kinase inhibitors. Eur J Med Chem, 182, 111664. doi: 10.1016/j.ejmech.2019.111664.
  • Zengin, G., Locatelli, M., Carradori, S., Mocan, A. M. & Aktumsek, A. (2016). Total phenolics, flavonoids, condensed tannins content of eight Centaurea species and their broad inhibitory activities against cholinesterase, tyrosinase, α-amylase and α-glucosidase. Not Bot Horti Agrobot Cluj-Napoca, 44, 195–200. doi: 10.15835/nbha44110259.
  • Zengin, G., Zheleva-Dimitrova, D., Gevrenova, R., Nedialkov, P., Mocan, A., Ćirić, A., Glamočlija, J., Soković, M., Aktumsek, A. & Mahomoodally, M. F. (2018). Identification of phenolic components via LC–MS analysis and biological activities of two Centaurea species: C. drabifolia subsp. drabifolia and C. lycopifolia. J Pharm Biomed Anal, 149, 436-441. doi: 10.1016/j.jpba.2017.11.045.
Toplam 51 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Yapısal Biyoloji
Bölüm ARAŞTIRMA MAKALESİ (Research Article)
Yazarlar

Dursun Kısa 0000-0002-7681-2385

Ahmet Çelik 0000-0001-9802-4868

Rizvan İmamoğlu 0000-0002-6306-4760

Proje Numarası 2021-FEN-A-004
Erken Görünüm Tarihi 13 Ekim 2023
Yayımlanma Tarihi 28 Şubat 2024
Gönderilme Tarihi 9 Mayıs 2023
Kabul Tarihi 28 Temmuz 2023
Yayımlandığı Sayı Yıl 2024

Kaynak Göster

APA Kısa, D., Çelik, A., & İmamoğlu, R. (2024). Assessment of Inhibitory Ability Against Medicinally Important Enzymes with Invitro and In Silico Studies: Phenolic Content of Endemic Centaurea cadmea subsp. pontica. Kahramanmaraş Sütçü İmam Üniversitesi Tarım Ve Doğa Dergisi, 27(1), 14-25. https://doi.org/10.18016/ksutarimdoga.vi.1294720

21082



2022-JIF = 0.500

2022-JCI = 0.170

Uluslararası Hakemli Dergi (International Peer Reviewed Journal)

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      Yılda 6 sayı yayınlanır. (Published 6 times a year)


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