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Helichrysum plicatum subsp. pseudopliacatum'un LC-MS/MS ile metabolik profilinin belirlenmesi, antioksidan aktivitelerinin ve enzim inhibisyon etkilerinin değerlendirilmesi

Yıl 2024, Cilt: 27 Sayı: 3, 501 - 514, 30.06.2024
https://doi.org/10.18016/ksutarimdoga.vi.1360450

Öz

Helichrysum türleri geleneksel olarak birçok hastalık tedavisinde kullanılmaktadır. Bu çalışmada, Helichrysum plicatum subsp. pseudopliacatum’den elde edilen metanol (MEHP) ve su (WEHP) ekstrelerinin antioksidan ve enzim inhibisyon etkilerinin belirlenmesi amaçlanmıştır. Ayrıca her iki ekstrede bulunan fenolik bileşiklerin belirlenmesi ve toplam fenolik ve flavonoit miktarlarının hesaplanması da amaçlanmıştır. Her iki ekstrenin antioksidan aktivitesini değerlendirmek için DPPH, ABTS ve DMPD radikal giderme, FRAP, Cu2+ ve Fe3+ indirgeme metotları kullanılmıştır. Ekstrelerin α-glikozidaz (α-Gly), asetilkolinesteraz (AChE) ve karbonik anhidraz II (CA II) enzimleri üzerinde inhibisyon etkileri spektrofotometrik olarak değerlendirildi ve standart inhibitörler ile mukayese edildi. Ekstrelerde bulunan fenolik maddelerin kalitatif ve kantitatif analizi ise sıvı kromatografisi tandem kütle spektrometresi (LC-MS/MS) ile belirlendi.
MEHP ve WEHP’ye ait %50 inhibisyona sebep olan inhibitör konsantrasyonu olan IC50 değeri, α-Gly için 2.39 ve 2.97 μg mL-1, AChE için 2.48 ve 3.59 μg mL-1 ve CA II için ise 11.95 ve 25.67 μg mL-1 olarak bulundu. MEHP ve WEHP'deki toplam fenolik miktarı sırasıyla 46.00 ve 33.50 μg GAE mg-1 ekstre; toplam flavonoit ise 62.13 ve 103.93 μg QE mg-1 ekstre olarak hesaplandı. MEHP ve WEHP’nin sırasıyla DPPH radikal gidermeye ait IC50 değerleri 40.77 ve 49.51 µg/mL, ABTS radikal gidermeye ait IC50 değerleri ise 10.50 ve 17.77 µg mL-1 ve DMPD radikal gidermeye ait IC50 değerleri IC50= 99.02 ve 77.01 µg mL-1 olarak belirlenmiştir. MEHP ve WEHP’in Fe3+ indirgeme kapasitesine ait absorbans değerleri sırasıyla indirgeme 0.555 ve 0.495, FRAP indirgeme kapasitesine ait absorbans değerleri 0.577 ve 0.286 ve Cu2+ indirgeme kapasitesine ait absorbans değerleri ise 0.402 ve 0.315 olarak bulundu. LC-MS/MS analizi sonucunda MEHP ve WEHP'de klorojenik asit, siyanidin-3-O-glikozit ve kinik asidin en fazla bulunduğu belirlendi. Bu çalışmada, MEHP ve WEHP'in etkili antioksidan etkiye sahip olduğunu ve α-Gly, AChE ve CA II enzimlerini etkili bir şekilde inhibe ettiği gözlendi. Elde edilen bulgular, geleneksel tıpta uzun süredir kullanılan Helichrysum türlerinin antioksidan ve enzim inhibisyon potansiyelini açık bir şekilde ortaya koymaktadır. Bu çalışmada kullanılan Helichrysum plicatum ekstreleri global ve yaygın birer hastalık olan diyabet, glokom ve Alzheimer hastalığına karşı oldukça etkili olduklarını gösterdi.

Kaynakça

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  • Aslan, M., Deliorman, O. D., Orhan, N., Sezik, E., & Yesilada, E. (2007). In vivo antidiabetic and antioxidant potential of Helichrysum plicatum ssp. plicatum capitulums in streptozotocin-induced-diabetic rats. Journal of Ethnopharmacology, 109 (1), 54-59.
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Determination of metabolic profiling by LC-MS/MS, evaluation of antioxidant activities, and enzyme inhibition effects of Helichrysum plicatum subsp. pseudopliacatum

Yıl 2024, Cilt: 27 Sayı: 3, 501 - 514, 30.06.2024
https://doi.org/10.18016/ksutarimdoga.vi.1360450

Öz

Helichrysum species are traditionally used to treat many diseases. In this study, the antioxidant and enzyme inhibition abilities of methanol (MEHP) and water extracts (WEHP) from Helichrysum plicatum subsp. Pseudopliacatum was evaluated. Also, the phenolic compounds will be assessed and the quantities of total phenols and flavonoids will be calculated. For evaluation of antioxidant activity of both extracts was assessed using DPPH, ABTS and DMPD radical scavenging, FRAP, CUPRAC, and Fe3+ reduction methods were used. The inhibition effects of extracts were spectrophotometrically evaluated on the α-glucosidase (α-Gly), acetylcholinesterase (AChE), and carbonic anhydrase II (CA II) enzymes. These inhibition effects were compared to the standard inhibitors The qualitative and quantitative phenolic components in extracts were analyzed by liquid chromatography-tandem mass spectrometry (LC-MS/MS), employing both methods. The IC50 value, which is the inhibitor concentration that causes 50% inhibition of MEHP and WEHP, is found as 2.39 and 2.97 μg mL-1 for α-gly, 2.48 and 3.59 μg mL-1 for AChE and 11.95 and 25.67 μg mL-1for CA II. The quantity of phenols in MEHP and WEHP were 46.00 and 33.50 μg GAE mg-1 extract, 62.13 and 103.93 μg QE mg-1 extract flavonoids, respectively. IC50 values of MEHP and WEHP were calculated as 40.77 and 49.51 μg mL-1 for DPPH radical scavenging, 10.50 and 17.77 μg mL-1 ABTS radical scavenging and 99.02 and 77.01 μg mL-1 DMPD radical scavenging. The absorbance values of reducing abilities of MEHP and WEHP were found as 0.555 and 0.495 Fe3+ reducing ability, 0.577 and 0.286 for FRAP reducing ability and 0.402 and 0.315 for Cu2+ reducing ability. As a result of the LC-MS/MS analysis, the levels of phenolic compounds such as chlorogenic acid, cyanidin-3-O-glucoside and quinic acid were found to be high in MEHP and WEHP. In this study, it was observed that MEHP and WEHP have strong antioxidant properties and effectively inhibited the enzymes activities. The findings clearly reveal the antioxidant and enzyme inhibition potential of Helichrysum species, which have been used in traditional medicine for a long time. Helichrysum plicatum extracts used in this study show that they are very effective against diabetes, glaucoma and Alzheimer's disease, which are global and common diseases.

Kaynakça

  • Ak, T., & Gülçin, İ. (2008). Antioxidant and radical scavenging properties of curcumin. Chemico-Biological Interactions, 174 (1), 27-37.
  • Al-Rehaily, A. J., Albishi, O. A., El-Olemy, M. M., & Mossa, J. S. (2008). Flavonoids and terpenoids from Helichrysum forskahlii. Phytochemistry, 69 (9), 1910-1914.
  • Albayrak, S., Aksoy, A., Sagdic, O., & Hamzaoglu, E. (2010a). Compositions, antioxidant and antimicrobial activities of Helichrysum (Asteraceae) species collected from Turkey. Food Chemistry, 119 (1), 114-122.
  • Albayrak, S., Aksoy, A., Sağdıç, O., & Budak, Ü. (2010b). Phenolic compounds and antioxidant and antimicrobial properties of Helichrysum species collected from eastern Anatolia, Turkey. Turkish Journal of Biology, 34 (4), 463-473.
  • Apak, R., Calokerinos, A., Gorinstein, S., Segundo, M.A., Hibbert, D.B., Gülçin, İ., Demirci Çekiç, S., Güçlü, K., Özyürek, M., Esin Çelik, S., Magalhaes, L.M., & Arancibia-Avila P. (2022). Methods to evaluate the scavenging activity of antioxidants toward reactive oxygen and nitrogen species. Pure and Applied Chemistry, 94(1), 87-144.
  • Aslan, M., Deliorman, O. D., Orhan, N., Sezik, E., & Yesilada, E. (2007). In vivo antidiabetic and antioxidant potential of Helichrysum plicatum ssp. plicatum capitulums in streptozotocin-induced-diabetic rats. Journal of Ethnopharmacology, 109 (1), 54-59.
  • Aydin, T. (2020). Secondary metabolites of Helichrysum plicatum DC. subsp. plicatum flowers as strong carbonic anhydrase, cholinesterase and alpha-glycosidase inhibitors. Zeitschrift Fur Naturforschung Section C- Journal of Biosciences, 75 (5-6), 153-159.
  • Bayir, Y., Halici, Z., Keles, M. S., Colak, S., Cakir, A., Kaya, Y., & Akcay, F. (2011). Helichrysum plicatum DC. subsp. plicatum extract as a preventive agent in experimentally induced urolithiasis model. Journal of Ethnopharmacology, 138 (2), 408-414.
  • Bayrak, C., Taslimi, P., Karaman, H. S., Gulcin, I., & Menzek, A. (2019). The first synthesis, carbonic anhydrase inhibition and anticholinergic activities of some bromophenol derivatives with S including natural products. Bioorganic Chemistry, 85, 128-139.
  • Benelli, G., Pavela, R., Rakotosaona, R., Randrianarivo, E., Nicoletti, M., & Maggi, F. (2018). Chemical composition and insecticidal activity of the essential oil from Helichrysum faradifani endemic to Madagascar. Natural Product Research, 32 (14), 1690-1698.
  • Blois, M. S. (1958). Antioxidant determinations by the use of a stable free radical. Nature, 181 (4617), 1199-1200.
  • Bursal, E., & Köksal, E. (2011). Evaluation of reducing power and radical scavenging activities of water and ethanol extracts from sumac (Rhus coriaria L.). Food Research International, 44 (7), 2217-2221.
  • Bursal, E., Köksal, E., Gülçin, İ., Bilsel, G., & Gören, A. C. (2013). Antioxidant activity and polyphenol content of cherry stem (Cerasus avium L.) determined by LC–MS/MS. Food Research International, 51(1), 66-74.
  • Carini, M., Aldini, G., Furlanetto, S., Stefani, R., & Facino, R. M. (2001). LC coupled to ion-trap MS for the rapid screening and detection of polyphenol antioxidants from Helichrysum stoechas. Journal of Pharmaceutical and Biomedical Analysis, 24 (3), 517-526.
  • Çetinkaya, Y., Göçer, H., Menzek, A., & Gülçin, İ. (2012). Synthesis and antioxidant properties of (3,4-dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone and its derivatives. Archiv der Pharmazie, 345 (4), 323-334.
  • Davis, P., & Kupicha, K. (1975). Helichrysum. In P. H. Davis (Ed.), Flora of Turkey and the East Aegean Islands (Vol. 5, pp. 80-96). the University Press.
  • Durmaz, L., Kiziltas, H., Guven, L., Karagecili, H., Alwasel, S., & Gulcin, İ. (2022). Antioxidant, antidiabetic, anticholinergic, and antiglaucoma effects of magnofluorine. Molecules, 27 (18), 5902.
  • Ellman, G. L., Courtney, K. D., Andres, V., & Featherstone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7 (2), 88-95.
  • Farris, E., Canopoli, L., Cucca, E., Landi, S., Maccioni, A., & Filigheddu, R. (2017). Foxes provide a direct dispersal service to Phoenician junipers in Mediterranean coastal environments: ecological and evolutionary implications. Plant Ecology and Evolution, 150 (2), 117-128.
  • Fogliano, V., Verde, V., Randazzo, G., & Ritieni, A. (1999). Method for measuring antioxidant activity and its application to monitoring the antioxidant capacity of wines. Journal of Agricultural and Food Chemistry, 47 (3), 1035-1040.
  • Göçer, H., & Gülçin, İ. (2011). Caffeic acid phenethyl ester (CAPE): correlation of structure and antioxidant properties. International Journal of Food Sciences and Nutrition, 62 (8), 821-825.
  • Gradinaru, A. C., Silion, M., Trifan, A., Miron, A., & Aprotosoaie, A. C. (2014). Helichrysum arenarium subsp. arenarium: phenolic composition and antibacterial activity against lower respiratory tract pathogens. Natural Product Research, 28 (22), 2076-2080.
  • Gulcin, İ. (2020). Antioxidants and antioxidant methods: an updated overview. Archives of Toxicology, 94 (3), 651-715.
  • Gulcin, İ., & Alwasel, S. H. (2022). Metal ions, metal chelators and metal chelating assay as antioxidant method. Processes, 10 (1), 132.
  • Gulcin, İ., & Alwasel, S. H. (2023). DPPH Radical Scavenging Assay. Processes, 11 (8), 2248.
  • Gulcin, I., Kaya, R., Goren, A. C., Akincioglu, H., Topal, M., Bingol, Z., Çetin Çakmak K., Öztürk Sarıkaya S. B., Durmaz L. & Alwasel, S. (2019). Anticholinergic, antidiabetic and antioxidant activities of cinnamon (Cinnamomum verum) bark extracts: polyphenol contents analysis by LC-MS/MS. International Journal of Food Properties, 22 (1), 1511-1526.
  • Gulcin, I., & Beydemir, S. (2013). Phenolic compounds as antioxidants: carbonic anhydrase isoenzymes inhibitors. Mini Reviews in Medicinal Chemistry, 13 (3), 408-430.
  • Guven, L., Ozgen, U., Sevindik, H., Agan, İ., Koca, M., Turan, İ., Demir S., Aliyazicioglu Y. (2022). Evaluation of LC-MS/MS analysis and in vitro biological activities of Rosa pimpinellifolia root, pseudo-fruit, and seed extracts. International Journal of Life Sciences and Biotechnology, 5 (3), 480-503.
  • Gülçin, I. (2008). Measurement of antioxidant ability of melatonin and serotonin by the DMPD and CUPRAC methods as trolox equivalent. Journal of Enzyme Inhibition and Medicinal Chemistry, 23 (6), 871-876.
  • Gülçin, İ., Bingöl, Z., Taslimi, P., Gören, A. C., Alwasel, S. H., & Tel, A. Z. (2022). Polyphenol contents, potential antioxidant, anticholinergic and antidiabetic properties of mountain mint (Cyclotrichium leucotrichum). Chemistry & Biodiversity, 19 (3), e202100775.
  • Gülçin, İ., Bursal, E., Şehitoğlu, M. H., Bilsel, M., & Gören, A. C. (2010). Polyphenol contents and antioxidant activity of lyophilized aqueous extract of propolis from Erzurum, Turkey. Food and Chemical Toxicology, 48 (8), 2227-2238.
  • Güven, L., Erturk, A., Miloğlu, F. D., Alwasel, S., & Gulcin, İ. (2023). Screening of antiglaucoma, antidiabetic, anti-alzheimer, and antioxidant activities of Astragalus alopecurus Pall-Analysis of phenolics profiles by LC-MS/MS. Pharmaceuticals , 16 (5), 659.
  • Huyut, Z., Beydemir, Ş., & Gülçin, İ. (2017). Inhibition properties of some flavonoids on carbonic anhydrase I and II isoenzymes purified from human erythrocytes. Journal of Biochemical and Molecular Toxicology, 31 (9), e21930.
  • Karagecili, H., Yılmaz, M. A., Ertürk, A., Kiziltas, H., Güven, L., Alwasel, S. H., & Gulcin, İ. (2023). Comprehensive metabolite profiling of berdav propolis using LC-MS/MS: determination of antioxidant, anticholinergic, antiglaucoma, and antidiabetic effects. Molecules, 28 (4), 1739.
  • Karageçili, H., İzol, E., Kireçci, E., & Gülçin, İ. (2023). Antioxidant, antidiabetic, antiglaucoma, and anticholinergic effects of Tayfi grape (Vitis vinifera): A phytochemical screening by LC-MS/MS analysis. Open Chemistry, 21(1), 20230120.
  • Kazancı, C., Oruç, S., & Mosulishvili, M. (2020). Medicinal ethnobotany of wild plants: a cross-cultural comparison around Georgia-Turkey border, the Western Lesser Caucasus. Journal of Ethnobiology and Ethnomedicine, 16 (1), 71.
  • Kherbache, A., Senator, A., Laouicha, S., Al-Zoubi, R. M., & Bouriche, H. (2020). Phytochemical analysis, antioxidant and anti-inflammatory activities of Helichrysum stoechas (L.) Moench extracts. Biocatalysis and Agricultural Biotechnology, 29, 101826.
  • Kiziltas, H., Bingol, Z., Goren, A. C., Pinar, S. M., Alwasel, S. H., & Gulcin, I. (2021). LC-HRMS profiling of phytochemicals, antidiabetic, anticholinergic and antioxidant activities of evaporated ethanol extract of Astragalus brachycalyx Fischer. Journal of Chemical Metrology, 15(2), 135-151.
  • Kızıltaş, H., Bingol, Z., Gören, A. C., Kose, L. P., Durmaz, L., Topal, F., Alwasel, S. H., Gulcin, İ. (2021). LC-HRMS profiling and antidiabetic, anticholinergic, and antioxidant activities of aerial parts of kınkor (Ferulago stellata). Molecules, 26 (9), 2469.
  • Koçyiğit, Ü.M., Eruygur, N., Ataş, M., Tekin, M., Taslimi, P., Gökalp, F., Gülçin, İ. (2022). Evaluation of anticholinergic, antidiabetic and antioxidant activity of Astragalus dumanii, an endemic plant. KSU Journl of Agriculture and Nature, 25(S1), 1-10.
  • Kolaylı, S., Sahin, H., Ulusoy, E., & Tarhan, Ö. (2010). Phenolic composition and antioxidant capacities of Helichrysum plicatum. Hacettepe Journal of Biological Chemistry 38, 269-276.
  • Köse, L. P., Gülçin, İ., Gören, A. C., Namiesnik, J., Martinez-Ayala, A. L., & Gorinstein, S. (2015). LC–MS/MS analysis, antioxidant and anticholinergic properties of galanga (Alpinia officinarum Hance) rhizomes. Industrial Crops and Products, 74, 712-721.
  • Miloglu, F. D., Akpınar, A., Güven, L., Demirkaya, A. K., Gundogdu, G., Nalcı, K. A., & Hacımuftuoglu, A. (2023). Evaluation the effects of Helichrysum plicatum subsp. pseudoplicatum on an in-vitro wound model using human dermal fibroblast cells. The International Journal of Lower Extremity Wounds, 22 (2), 401-408.
  • Orhan, N., Hocbac, S., Orhan, D. D., Asian, M., & Ergun, F. (2014). Enzyme inhibitory and radical scavenging effects of some antidiabetic plants of Turkey. Iranian Journal of Basic Medical Sciences, 17 (6), 426-432.
  • Oyaizu, M. (1986). Studies on products of browning Reaction Antioxidative Activities of Products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44 (6), 307-315.
  • Ozaslan, M. S., Saglamtas, R., Demir, Y., Genc, Y., Saracoglu, I., & Gulcin, I. (2022) Isolation of some phenolic compounds from Plantago subulata L. and determination of their antidiabetic, anticholinesterase, antiepileptic and antioxidant activity. Chemistry & Biodiversity, Article e202200280.
  • Pljevljakusic, D., Bigovic, D., Jankovic, T., Savikin, K., & Jelacic, S. (2018). Sandy everlasting (Helichrysum arenarium (L.) Moench): botanical, chemical and biological properties. Frontiers in Plant Science, 9, 1123.
  • Popoola, O. K., Marnewick, J. L., Rautenbach, F., Iwuoha, E. I., & Hussein, A. A. (2015). Acylphloroglucinol derivatives from the South African Heliehrysum niveum and their biological activities. Molecules, 20 (9), 17309-17324.
  • Raina, R., Parwez, S., Verma, P. K., & Pankaj, N. K. (2008). Medicinal plants and their role in wound healing. Online Veterinary Journal, 3 (1), 21.
  • Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., & Rice-Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26 (9), 1231-1237.
  • Sezer Senol, F., Orhan, I. E., Ozgen, U., Renda, G., Bulut, G., Guven, L., Sezen Karaoglan E., Sevindik H.G., Skalicka-Wozniak K., Koca Caliskan U., Sekeroglu, N. (2016). Memory-vitalizing effect of twenty-five medicinal and edible plants and their isolated compounds. South African Journal of Botany, 102, 102-109.
  • Silva, L., Rodrigues, A. M., Ciriani, M., Falé, P. L. V., Teixeira, V., Madeira, P Machuqueiro M., Pacheco R., Florencio M. H., Ascensão, L., Marques Serralheiro M. L. (2017). Antiacetylcholinesterase activity and docking studies with chlorogenic acid, cynarin and arzanol from Helichrysum stoechas (Lamiaceae). Medicinal Chemistry Research, 26 (11), 2942-2950.
  • Singleton, V. L., Orthofer, R., & Lamuela-Raventós, R. M. (1999). Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteu reagent. In Methods in Enzymology, 299, 152-178.
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  • Şenol, H., Çelik Turgut, G., Şen, A., Sağlamtaş, R., Tuncay, S., Gülçin, İ., & Topçu, G. (2023). Synthesis of nitrogen-containing oleanolic acid derivatives as carbonic anhydrase and acetylcholinesterase inhibitors. Medicinal Chemistry Research, 32 (4), 694-704.
  • Tao, Y., Zhang, Y., Cheng, Y., & Wang, Y. (2013). Rapid screening and identification of α-glucosidase inhibitors from mulberry leaves using enzyme-immobilized magnetic beads coupled with HPLC/MS and NMR. Biomedical Chromatography, 27 (2), 148-155.
  • Taslimi, P., & Gulçin, İ. (2018). Antioxidant and anticholinergic properties of olivetol. Journal of Food Biochemistry, 42 (3), e12516.
  • Taslimi, P., Köksal, E., Gören, A. C., Bursal, E., Aras, A., Kılıç, Ö., Alwasel S., & Gülçin, İ. (2020). Anti-Alzheimer, antidiabetic and antioxidant potential of Satureja cuneifolia and analysis of its phenolic contents by LC-MS/MS. Arabian Journal of Chemistry, 13 (3), 4528-4537.
  • Tepe, B., Sokmen, M., Askin Akpulat, H., & Sokmen, A. (2004). In vitro antioxidant activities of the methanol extracts of four Helichrysum species from Turkey. Food Chemistry, 90 (4), 685-689.
  • Topal, M., & Gulcin, I. (2014). Rosmarinic acid: A potent carbonic anhydrase isoenzymes inhibitor. Turkish Journal of Chemistry, 38 (5), 894-902.
  • Türkan, F., Atalar, M. N., Aras, A., Gülçin, İ., & Bursal, E. (2020). ICP-MS and HPLC analyses, enzyme inhibition and antioxidant potential of Achillea schischkinii Sosn. Bioorganic Chemistry, 94, 103333.
Toplam 61 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Farmasotik Botanik
Bölüm ARAŞTIRMA MAKALESİ (Research Article)
Yazarlar

Leyla Güven 0000-0002-3189-6415

İlhami Gülçin 0000-0001-5993-1668

Erken Görünüm Tarihi 11 Mart 2024
Yayımlanma Tarihi 30 Haziran 2024
Gönderilme Tarihi 15 Eylül 2023
Kabul Tarihi 2 Kasım 2023
Yayımlandığı Sayı Yıl 2024Cilt: 27 Sayı: 3

Kaynak Göster

APA Güven, L., & Gülçin, İ. (2024). Determination of metabolic profiling by LC-MS/MS, evaluation of antioxidant activities, and enzyme inhibition effects of Helichrysum plicatum subsp. pseudopliacatum. Kahramanmaraş Sütçü İmam Üniversitesi Tarım Ve Doğa Dergisi, 27(3), 501-514. https://doi.org/10.18016/ksutarimdoga.vi.1360450

21082



2022-JIF = 0.500

2022-JCI = 0.170

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