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Phytochemical Profiles and Antiproliferative Effect of Allium tuncelianum

Yıl 2020, Cilt: 23 Sayı: 1, 259 - 270, 28.02.2020

Kasım Takım , Türkan Kutlu

https://doi.org/10.18016/ksutarimdoga.vi.586805
Cited By: 6

Öz

In this study, Allium tuncelianum, one of the endemic garlic species growing in
Anatolia, was investigated for its phytochemical content. LC-MS/MS, HPLC,
GC-MS, GC-FID and ICP-OES techniques were used for this purpose. Major phenolic
components of Allium tuncelianum were
found to be malic acid (3322.6 µg/g), kainic acid (626.8 µg/g), cinnamic acid
(69.15 µg/g), fumaric acid (13.02 µg/g) and catechin (3933.3 µg/g). The main
components of volatile oil, on the other hand, were detected as diallyl
disulfide (28.30%), diallyl trisulfide (30.90%) and allyl methyl trisulfide
(9.44%). The fatty acid composition of the plant was revealed as oleic acid
(27.19%), linoleic acid (19.46%) and elaidic acid (3%) whereas high content of
potassium (4207± 67 mg/kg), calcium (518± 35 mg/kg) and magnesium (376 ± 20
mg/kg) was determined as the minerals. Moreover, cytotoxic effects of
ethanol/water and hexane/chloroform extracts of the plant were evaluated in
prostate, colon, cervical and breast cancer cell lines and cytotoxicity of both
extracts were detected for all the cell lines studied. Therefore, we conclude that Allium tuncelianum may be a new phytotherapy agent with its rich
phytochemical content and anticancer activity.

Anahtar Kelimeler

Garlic Fatty acids Volatile oil Phenolic LC-MS/MS

Destekleyen Kurum

Harran University Scientific Research Projects Coordination Unit.

Proje Numarası

16187

Teşekkür

Thanks to Harran University Scientific Research Projects Coordination Unit.

Kaynakça

  • Banerjee SK, Mukherjee PK, Maulik SK 2003. Garlic as an Antioxidant: The Good, the Bad and the Ugly. Phytotherapy Research, 17(2): 97-106.
  • Cai Y, Luo Q, Sun M, Corke H 2004. Antioxidant Activity and Phenolic Compounds of 112 Traditional Chinese Medicinal Plants Associated with Anticancer. Life Sciences, 74(17): 2157-84.
  • Çelik SE, Özyürek M, Güçlü K, Apak R 2010. Determination of Antioxidants by a Novel On-Line HPLC-Cupric Reducing Antioxidant Capacity (CUPRAC) Assay with Post- Column Detection. Analytica Chimica Acta, 674(1): 79-88.
  • Chekki RZ, Snoussi A, Hamrouni I, Bouzouita N 2014. Chemical Composition, Antibacterial and Antioxidant Activities of Tunisian Garlic (Allium Sativum) Essential Oil and Ethanol Extract. Mediterranean Journal of Chemistry, 3(4): 947-56.
  • Emen S, Çeken B, Kizil G, Kizil M 2009. DNA Damage Protecting Activity and in Vitro Antioxidant Potential of the Methanol Extract of Cyclotrichium Niveum. Pharmaceutical Biology, 47(3): 219-29.
  • Ertas, A, Boga M, Yilmaz MA, Yesil Y, Tel G, Temel H, Hasimi N, Gazioglu I, Ozturk M, Ugurlu P 2015. A Detailed Study on the Chemical and Biological Profiles of Essential Oil and Methanol Extract of Thymus Nummularius (Anzer Tea): Rosmarinic Acid. Industrial Crops and Products. 1(67): 336-45.
  • Farag MA, Ali SE, Hodaya RH, El-Seedi HR, Sultani HN, Laub A, FE Tarek, Abou-Zaid F, Wessjohann LA 2017. Phytochemical Profiles and Antimicrobial Activities of Allium Cepa Red Cv. and A. Sativum Subjected to Different Drying Methods: A Comparative MS-Based Metabolomics. Molecules, 8(22)5: 761
  • Fratianni F, Ombra MN, Cozzolino A, Riccardi R, Spigno P, Tremonte P, Coppola R, Nazzaro F 2016. Phenolic Constituents, Antioxidant, Antimicrobial and Anti-Proliferative Activities of Different Endemic Italian Varieties of Garlic (Allium Sativum L.). Journal of Functional Foods, 1(21): 240-48.
  • Gercek YC, Akman G, Morgil H,Calıkan M, Oz GC 2017. Organosulfur compounds of Allium Tuncelianum (Kollmann) Ozhatay, B. Mathew & Şiraneci extracts by SPME/GC-MS and determining their cytotoxic effect on HeLa cells. International Journal of Advances in Science Engineering and Technology. 5(2):53-58.
  • Hayaloglu AA, Demir N 2016. Phenolic compounds, volatiles, and sensory characteristics of twelve sweet cherry (Prunus avium L.) cultivars grown in Turkey. Journal of food science. 81(1): 7-18.
  • Huang WY, Cai YZ, Zhang Y 2009. Natural phenolic compounds from medicinal herbs and dietary plants: potential use for cancer prevention. Nutrition and cancer. 62(1): 1-20.
  • Islam MS, Kusumato Y, Abdulla Al-Mamun M 2011. Cytotoxicity and cancer (HeLa) cell killing efficiancy aqueous garlic (Allium sativum) extract. Journal of Scientific Research. 3(2):375-382.
  • Izol E 2016. Determination of Heavy Metals And Seconder Metabolites of Some Allium (Wild Garlic) Species By ICP-MS and LCMS/ MS Investigation of Their Biological Activities. DÜ Fen Bil. Ens., Kimya ABD, Yüksek Lisans Tezi, 129 s.
  • Jirovetz L, Jäger W, Koch HP, Remberg G 1992. Investigations of volatile constituents of the essential oil of Egyptian garlic (Allium sativum L.) by means of GC-MS and GC-FTIR. Zeitschrift für Lebensmittel-Untersuchung und Forschung. 194(4): 363-5.
  • Kilic A, Koyuncu I, Durgun M, Ozaslan I, Kaya IH, Gönel A 2018. Synthesis and Characterization of the Hemi‐Salen Ligands and Their Triboron Complexes: Spectroscopy and Examination of Anticancer Properties. Chemistry & biodiversity. 15(1): 17-42.
  • Kokten K, Bakoglu A, Kocak A, Bagci E, Akcura M, Kaplan M 2011. Chemical composition of the seeds of some Medicago species. Chemistry of Natural Compounds. 47(4): 619.
  • Lachowicz S, Kolniak‐Ostek J, Oszmiański J, Wiśniewski R 2017. Comparison of phenolic content and antioxidant capacity of bear garlic (Allium ursinum L.) in different maturity stages. Journal of food processing and preservation. 41(1): e12921.
  • Lee SN, Kim NS, Lee DS 2003. Comparative study of extraction techniques for determination of garlic flavor components by gas chromatography–mass spectrometry. Analytical and bioanalytical chemistry. 377(4): 749-56.
  • Li H, Wang SW, Zhang BL, Xie YH, Yang Q, Cao W, Wang JB 2011. Simultaneous quantitative determination of 9 active components in traditional Chinese medicinal preparation ShuangDan oral liquid by RP-HPLC coupled with photodiode array detection. Journal of pharmaceutical and biomedical analysis. 56(4): 820-4.
  • Lu HF, Sue CC, Yu CS, Chen SC, Chen GW, Chung JG 2004. Diallyl disulfide (DADS) induced apoptosis undergo caspase-3 activity in human bladder cancer T24 cells. Food and chemical toxicology. 42(10): 1543-52.
  • Menendez JA, Vellon L, Colomer R, Lupu R 2005. Oleic acid, the main monounsaturated fatty acid of olive oil, suppresses her-2/neu (erb b-2) expression and synergistically enhances the growth inhibitory effects of trastuzumab (herceptin™) in breast cancer cells with her-2/neu oncogene amplification. Annals of oncology. 16(3): 359-71.
  • Narendhirakannan RT, Rajeswari K 2010. In vitro antioxidant properties of three varieties of Allium sativum L. extracts. Journal of Chemistry. 7(1): 573-9.
  • Oommen S, Anto RJ, Srinivas G, Karunagaran D 2004. Allicin (from garlic) induces caspase-mediated apoptosis in cancer cells. European journal of pharmacology. 485(1-3): 97-103.
  • Özhatay N, Mathew B 1995. New taxa and notes on the genus Allium (Alliaceae) in Turkey and Arabia. Kew Bulletin. 1: 723-31.
  • Özhatay, N. 2002. Diversity of bulbous monocots in Turkey with special reference chromosome numbers. Pure Appl. Chem. 74(4):547-555
  • Ozkaya A, Ciftci H, Yilmaz O, Zafer Tel A, Cil E, Cevrimli BS 2012. Vitamin, trace element, and fatty acid levels of Vitex agnus-castus L., Juniperus oxycedrus L., and Papaver somniferum L. plant seeds. Journal of Chemistry. 2013(43): 4
  • Pandey M, Debnath M, Gupta S, Chikara SK 2011. Phytomedicine: An ancient approach turning into future potential source of therapeutics. Journal of Pharmacognosy and phytotherapy. 3(1):113-7.
  • Prakash E, Saxena AK, Gupta DK 2016. Cytotoxic activities of ethanolic extract of Allium sativum against colon cancer cell lines. International Journal of Innovative Research in Science, Engineering and Technology. 5(3):3041-3045.
  • Sarneckis CJ, Dambergs RG, Jones P, Mercurio M, Herderich MJ, Smith PA 2006. Quantification of condensed tannins by precipitation with methyl cellulose: development and validation of an optimised tool for grape and wine analysis. Australian Journal of Grape and Wine Research. 12(1): 39-49.
  • Singh A, Shukla Y 1998. Antitumour activity of diallyl sulfide on polycyclic aromatic hydrocarbon-induced mouse skin carcinogenesis. Cancer letters. 131(2): 209-14.
  • Soares ME, Carvalho F, de Lourdes Bastos M 2001. Determination of amphetamine and its metabolite p‐hydroxyamphetamine in rat urine by reversed‐phase high‐performance liquid chromatography after dabsyl derivatization. Biomedical Chromatography. 15(7): 452-6.
  • Mosmann T 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of immunological methods. 65(1-2):55-63.
  • Yildirim I, Kutlu T, Takim K 2015. Comparison of antioxidant activity of Rheum ribes fruits and seed methanolic extracts against protein oxidation and lipid peroxidation. Pakistan J. Biol. Sci. 18(5): 232-9.
  • Tsiaganis MC, Laskari K, Melissari E 2006. Fatty acid composition of Allium species lipids. Journal of Food Composition and Analysis. 19(6-7): 620-7.
  • Vlase L, Parvu M, Parvu E, Toiu A 2013. Chemical constituents of three Allium species from Romania. Molecules. 18(1): 114-27.
  • Waheed A, Jaffar M, Masud K 2003. Comparative study of selected essential and non-essential metals in various canned and raw foodstuffs consumed in Pakistan. Nutrition & Food Science. 33(6): 261-7.
  • Yanmaz R, Yazar E, Kantoglu KY, Alper A 2010. In vitro plant regeneration and bulblet formation of Tunceli garlic (Allium tuncelianum (Kollman) Özhatay, Matthew, Siraneci) by shoot and root culture. Journal of Food, Agriculture & Environment. 8(3&4): 572-6.
  • Yılmaz MA 2015. Determining the Metabolic Profile of Some Achillea. DÜ Fen Bil. Ens., Kimya ABD, Doktora Tezi, 314 s.
  • Yünlü S 2011. Determination of Phenolic Compounds in Onion (Allium Cepa) and Garlic (Allium Sativum) By HPLC Method. SDÜ. Fen Bil. Ens., Kimya ABD, Yüksek Lisans Tezi, 101 s.

Allium tuncelianum' un Fitokimyasal Profilinin Belirlenmesi ve Çeşitli İnsan Hücre Hatlarında Antiproliferatif Etkilerinin Değerlendirilmesi

Yıl 2020, Cilt: 23 Sayı: 1, 259 - 270, 28.02.2020

Kasım Takım , Türkan Kutlu

https://doi.org/10.18016/ksutarimdoga.vi.586805
Cited By: 6

Öz

Bu
çalışmada, Anadoluda yetişen endemik sarımsak türlerinden biri olan Tunceli Dağ
Sarımsağı (Allium tuncelianum) incelenmiştir. Fitokimyasal içeriği belirlemek
için LC-MS / MS, HPLC, GC-MS, GC-FID ve ICP-OES teknikleri kullanılmıştır. Allium tuncelianum'un başlıca fenolik
bileşenleri; malik asit (3322,6 µg / g), kainik asit (626.8 µg / g), sinamik
asit (69.15 µg / g), fumarik asit (13.02 µg / g) ve kateşin (3933.3 µg / g)
olduğu belirlendi. Uçucu yağın ana bileşenleri, dialil disülfit (% 28.30),
dialil trisülfit (% 30.90) ve allil metil trisülfit (% 9.44) idi. Yağ asidi
bileşimi; oleik asit (% 27.19), linoleik asit (% 19.46) ve elaidik asit (% 3)
iken, mineral içeriğindeki major elementler; potasyum (4207 ± 67 mg / kg), kalsiyum
(518 ± 35 mg / kg) ve magnezyum (376 ± 20) mg / kg) olarak belirlenmiştir.
Prostat, kolon, servikal ve meme kanseri hücre dizilerinde sitotoksik etki de
incelenmiştir. Kolon, Meme, Servikal ve Prostat kanseri hücre hatlarında
sitotoksik etki tespit edildi. Bu sonuçlar göstermektedir ki; Allium tuncelianum, zengin fitokimyasal
içeriği ve antikanser aktivitesi ile yeni bir fitoterapi ajanı olabilir.

Anahtar Kelimeler

Sarımsak Yağ asitleri Uçucu yağ Fenolik Sitotoksik aktivite

Proje Numarası

16187

Kaynakça

  • Banerjee SK, Mukherjee PK, Maulik SK 2003. Garlic as an Antioxidant: The Good, the Bad and the Ugly. Phytotherapy Research, 17(2): 97-106.
  • Cai Y, Luo Q, Sun M, Corke H 2004. Antioxidant Activity and Phenolic Compounds of 112 Traditional Chinese Medicinal Plants Associated with Anticancer. Life Sciences, 74(17): 2157-84.
  • Çelik SE, Özyürek M, Güçlü K, Apak R 2010. Determination of Antioxidants by a Novel On-Line HPLC-Cupric Reducing Antioxidant Capacity (CUPRAC) Assay with Post- Column Detection. Analytica Chimica Acta, 674(1): 79-88.
  • Chekki RZ, Snoussi A, Hamrouni I, Bouzouita N 2014. Chemical Composition, Antibacterial and Antioxidant Activities of Tunisian Garlic (Allium Sativum) Essential Oil and Ethanol Extract. Mediterranean Journal of Chemistry, 3(4): 947-56.
  • Emen S, Çeken B, Kizil G, Kizil M 2009. DNA Damage Protecting Activity and in Vitro Antioxidant Potential of the Methanol Extract of Cyclotrichium Niveum. Pharmaceutical Biology, 47(3): 219-29.
  • Ertas, A, Boga M, Yilmaz MA, Yesil Y, Tel G, Temel H, Hasimi N, Gazioglu I, Ozturk M, Ugurlu P 2015. A Detailed Study on the Chemical and Biological Profiles of Essential Oil and Methanol Extract of Thymus Nummularius (Anzer Tea): Rosmarinic Acid. Industrial Crops and Products. 1(67): 336-45.
  • Farag MA, Ali SE, Hodaya RH, El-Seedi HR, Sultani HN, Laub A, FE Tarek, Abou-Zaid F, Wessjohann LA 2017. Phytochemical Profiles and Antimicrobial Activities of Allium Cepa Red Cv. and A. Sativum Subjected to Different Drying Methods: A Comparative MS-Based Metabolomics. Molecules, 8(22)5: 761
  • Fratianni F, Ombra MN, Cozzolino A, Riccardi R, Spigno P, Tremonte P, Coppola R, Nazzaro F 2016. Phenolic Constituents, Antioxidant, Antimicrobial and Anti-Proliferative Activities of Different Endemic Italian Varieties of Garlic (Allium Sativum L.). Journal of Functional Foods, 1(21): 240-48.
  • Gercek YC, Akman G, Morgil H,Calıkan M, Oz GC 2017. Organosulfur compounds of Allium Tuncelianum (Kollmann) Ozhatay, B. Mathew & Şiraneci extracts by SPME/GC-MS and determining their cytotoxic effect on HeLa cells. International Journal of Advances in Science Engineering and Technology. 5(2):53-58.
  • Hayaloglu AA, Demir N 2016. Phenolic compounds, volatiles, and sensory characteristics of twelve sweet cherry (Prunus avium L.) cultivars grown in Turkey. Journal of food science. 81(1): 7-18.
  • Huang WY, Cai YZ, Zhang Y 2009. Natural phenolic compounds from medicinal herbs and dietary plants: potential use for cancer prevention. Nutrition and cancer. 62(1): 1-20.
  • Islam MS, Kusumato Y, Abdulla Al-Mamun M 2011. Cytotoxicity and cancer (HeLa) cell killing efficiancy aqueous garlic (Allium sativum) extract. Journal of Scientific Research. 3(2):375-382.
  • Izol E 2016. Determination of Heavy Metals And Seconder Metabolites of Some Allium (Wild Garlic) Species By ICP-MS and LCMS/ MS Investigation of Their Biological Activities. DÜ Fen Bil. Ens., Kimya ABD, Yüksek Lisans Tezi, 129 s.
  • Jirovetz L, Jäger W, Koch HP, Remberg G 1992. Investigations of volatile constituents of the essential oil of Egyptian garlic (Allium sativum L.) by means of GC-MS and GC-FTIR. Zeitschrift für Lebensmittel-Untersuchung und Forschung. 194(4): 363-5.
  • Kilic A, Koyuncu I, Durgun M, Ozaslan I, Kaya IH, Gönel A 2018. Synthesis and Characterization of the Hemi‐Salen Ligands and Their Triboron Complexes: Spectroscopy and Examination of Anticancer Properties. Chemistry & biodiversity. 15(1): 17-42.
  • Kokten K, Bakoglu A, Kocak A, Bagci E, Akcura M, Kaplan M 2011. Chemical composition of the seeds of some Medicago species. Chemistry of Natural Compounds. 47(4): 619.
  • Lachowicz S, Kolniak‐Ostek J, Oszmiański J, Wiśniewski R 2017. Comparison of phenolic content and antioxidant capacity of bear garlic (Allium ursinum L.) in different maturity stages. Journal of food processing and preservation. 41(1): e12921.
  • Lee SN, Kim NS, Lee DS 2003. Comparative study of extraction techniques for determination of garlic flavor components by gas chromatography–mass spectrometry. Analytical and bioanalytical chemistry. 377(4): 749-56.
  • Li H, Wang SW, Zhang BL, Xie YH, Yang Q, Cao W, Wang JB 2011. Simultaneous quantitative determination of 9 active components in traditional Chinese medicinal preparation ShuangDan oral liquid by RP-HPLC coupled with photodiode array detection. Journal of pharmaceutical and biomedical analysis. 56(4): 820-4.
  • Lu HF, Sue CC, Yu CS, Chen SC, Chen GW, Chung JG 2004. Diallyl disulfide (DADS) induced apoptosis undergo caspase-3 activity in human bladder cancer T24 cells. Food and chemical toxicology. 42(10): 1543-52.
  • Menendez JA, Vellon L, Colomer R, Lupu R 2005. Oleic acid, the main monounsaturated fatty acid of olive oil, suppresses her-2/neu (erb b-2) expression and synergistically enhances the growth inhibitory effects of trastuzumab (herceptin™) in breast cancer cells with her-2/neu oncogene amplification. Annals of oncology. 16(3): 359-71.
  • Narendhirakannan RT, Rajeswari K 2010. In vitro antioxidant properties of three varieties of Allium sativum L. extracts. Journal of Chemistry. 7(1): 573-9.
  • Oommen S, Anto RJ, Srinivas G, Karunagaran D 2004. Allicin (from garlic) induces caspase-mediated apoptosis in cancer cells. European journal of pharmacology. 485(1-3): 97-103.
  • Özhatay N, Mathew B 1995. New taxa and notes on the genus Allium (Alliaceae) in Turkey and Arabia. Kew Bulletin. 1: 723-31.
  • Özhatay, N. 2002. Diversity of bulbous monocots in Turkey with special reference chromosome numbers. Pure Appl. Chem. 74(4):547-555
  • Ozkaya A, Ciftci H, Yilmaz O, Zafer Tel A, Cil E, Cevrimli BS 2012. Vitamin, trace element, and fatty acid levels of Vitex agnus-castus L., Juniperus oxycedrus L., and Papaver somniferum L. plant seeds. Journal of Chemistry. 2013(43): 4
  • Pandey M, Debnath M, Gupta S, Chikara SK 2011. Phytomedicine: An ancient approach turning into future potential source of therapeutics. Journal of Pharmacognosy and phytotherapy. 3(1):113-7.
  • Prakash E, Saxena AK, Gupta DK 2016. Cytotoxic activities of ethanolic extract of Allium sativum against colon cancer cell lines. International Journal of Innovative Research in Science, Engineering and Technology. 5(3):3041-3045.
  • Sarneckis CJ, Dambergs RG, Jones P, Mercurio M, Herderich MJ, Smith PA 2006. Quantification of condensed tannins by precipitation with methyl cellulose: development and validation of an optimised tool for grape and wine analysis. Australian Journal of Grape and Wine Research. 12(1): 39-49.
  • Singh A, Shukla Y 1998. Antitumour activity of diallyl sulfide on polycyclic aromatic hydrocarbon-induced mouse skin carcinogenesis. Cancer letters. 131(2): 209-14.
  • Soares ME, Carvalho F, de Lourdes Bastos M 2001. Determination of amphetamine and its metabolite p‐hydroxyamphetamine in rat urine by reversed‐phase high‐performance liquid chromatography after dabsyl derivatization. Biomedical Chromatography. 15(7): 452-6.
  • Mosmann T 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of immunological methods. 65(1-2):55-63.
  • Yildirim I, Kutlu T, Takim K 2015. Comparison of antioxidant activity of Rheum ribes fruits and seed methanolic extracts against protein oxidation and lipid peroxidation. Pakistan J. Biol. Sci. 18(5): 232-9.
  • Tsiaganis MC, Laskari K, Melissari E 2006. Fatty acid composition of Allium species lipids. Journal of Food Composition and Analysis. 19(6-7): 620-7.
  • Vlase L, Parvu M, Parvu E, Toiu A 2013. Chemical constituents of three Allium species from Romania. Molecules. 18(1): 114-27.
  • Waheed A, Jaffar M, Masud K 2003. Comparative study of selected essential and non-essential metals in various canned and raw foodstuffs consumed in Pakistan. Nutrition & Food Science. 33(6): 261-7.
  • Yanmaz R, Yazar E, Kantoglu KY, Alper A 2010. In vitro plant regeneration and bulblet formation of Tunceli garlic (Allium tuncelianum (Kollman) Özhatay, Matthew, Siraneci) by shoot and root culture. Journal of Food, Agriculture & Environment. 8(3&4): 572-6.
  • Yılmaz MA 2015. Determining the Metabolic Profile of Some Achillea. DÜ Fen Bil. Ens., Kimya ABD, Doktora Tezi, 314 s.
  • Yünlü S 2011. Determination of Phenolic Compounds in Onion (Allium Cepa) and Garlic (Allium Sativum) By HPLC Method. SDÜ. Fen Bil. Ens., Kimya ABD, Yüksek Lisans Tezi, 101 s.
Toplam 39 adet kaynakça vardır.

Ayrıntılar

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

Kasım Takım 0000-0003-4631-1982

Türkan Kutlu 0000-0003-4631-1982

Proje Numarası 16187
Yayımlanma Tarihi 28 Şubat 2020
Gönderilme Tarihi 4 Temmuz 2019
Kabul Tarihi 11 Eylül 2019
Yayımlandığı Sayı Yıl 2020Cilt: 23 Sayı: 1

Kaynak Göster

APA Takım, K., & Kutlu, T. (2020). Phytochemical Profiles and Antiproliferative Effect of Allium tuncelianum. Kahramanmaraş Sütçü İmam Üniversitesi Tarım Ve Doğa Dergisi, 23(1), 259-270. https://doi.org/10.18016/ksutarimdoga.vi.586805

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