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The Characterization of Volatile Compounds Belonging to Some Lupin Genotypes By SPME GC-MS Method

Year 2023, Volume: 26 Issue: 4, 870 - 877, 31.08.2023

Ela Nur Şimşek Sezer , Mustafa Yorgancılar , Tuna Uysal

https://doi.org/10.18016/ksutarimdoga.vi.1205424

Abstract

In this paper, three Lupinus albus L. and two L. angustifolius L. genotypes were examined and compared in terms of volatiles or semi volatiles using GC-MS and SPME techniques. For this aim, the seeds of lupins were ground using a hand grinder, and this powder raw material was used to determine the content. Approximately 102 compounds obtained from lupin genotypes were identified for the first time, which mainly included benzene-methyl (1-methyl ethyl), 5-Allyl-4-(1-(p-amino phenyl) ethylidenehyl, 2-propen-1-ol, 3-phenyl-, m-Mentha-4,8,diene-(1S,3S)-(+), gamma terpinene. Thee compounds were determined to exist at different rates in different. As a result, it becomes evident that such studies aiming at revealing the active matters from plants or plant parts and their possible potentials, are of great importance in terms of more specific studies to be carried out in the future.

Keywords

Lupin Solid-phase micro-extraction Volatile compounds GC-MS

Thanks

We would like to thank Nihal İLHAN for her valuable support for the analysis.

References

  • Abraham, E. M., Ganopoulos, I., Madesis, P., Mavromatis, A., Mylona, P., Nianiou-Obeidat, I., Parissi, Z., Polidoros, A., Tani, E., & Vlachostergios, D. (2019). The use of lupin as a source of protein in animal feeding: Genomic tools and breeding approaches. International Journal of Molecular Sciences, 20(4), 851.
  • Arnoldi, A., Boschin, G., Zanoni, C., & Lammi, C. (2015). The health benefits of sweet lupin seed flours and isolated proteins. Journal of Functional Foods, 18, 550-563.
  • Arthur, C. L., & Pawliszyn, J. (1990). Solid-Phase Microextraction with Thermal-Desorption Using Fused-Silica Optical Fibers. Analytical Chemistry, 62(19), 2145-2148.
  • Bähr, M., Fechner, A., Kiehntopf, M., & Jahreis, G. (2015). Consuming a mixed diet enriched with lupin protein beneficially affects plasma lipids in hypercholesterolemic subjects: A randomized controlled trial. Clinical Nutrition, 34(1), 7-14.
  • Bhardwaj, H. L., & Hamama, A. A. (2012). Cultivar and growing location effects on white lupin immature green seeds. Journal of Agricultural Science, 4(2), 135.
  • Bicchi, C., Cordero, C., Liberto, E., Rubiolo, P., & Sgorbini, B. (2004). Automated headspace solid-phase dynamic extraction to analyse the volatile fraction of food matrices. Journal of Chromatography A, 1024(1-2), 217-226.
  • Bicchi, C., Drigo, S., & Rubiolo, P. (2000). Influence of fibre coating in headspace solid-phase microextraction–gas chromatographic analysis of aromatic and medicinal plants. Journal of Chromatography A, 892(1-2), 469-485.
  • Brummund, M., & Święcicki, W. (2011). The recent history of lupin in agriculture. Lupin crops: an apportunity for today a promise for the future. Proceedings of the 13th International Lupin Conference, Poznan, Poland, 6-12 June 2011.
  • Cardoso, D., Pennington, R. T., De Queiroz, L., Boatwright, J. S., Van Wyk, B.-E., Wojciechowski, M., & Lavin, M. (2013). Reconstructing the deep-branching relationships of the papilionoid legumes. South African Journal of Botany, 89, 58-75.
  • Cowling, W. A., Buirchell, B. J., & Tapia, M. E. (1998). Lupin. Lupinus L. International Plant Genetic Resources Institute (IPGRI).
  • Cowling, W. A., Huyghe, C., & Swiecicki, W. (1998). Lupin breeding. Lupins as crop plants: biology, production and utilization., 93-120.
  • Culvenor, C., & Petterson, D. (1986). Lupin toxins-alkaloids and phomopsins. 4. International Lupin Conference, p. 188-198, Geraldton, (WA) Australia, 17-22 Aug 1986.
  • Duranti, M., Consonni, A., Magni, C., Sessa, F., & Scarafoni, A. (2008). The major proteins of lupin seed: characterisation and molecular properties for use as functional and nutraceutical ingredients. Trends in Food Science & Technology, 19(12), 624-633.
  • Elma, F., Çetin, H., Yorgancılar, M., & Acar, R. (2021). Detection of Metabolite Content in Local Bitter White Lupin Seeds (Lupinus albus L.) and Acaricidal and Insecticidal Effect of its Seed Extract. Journal of Agricultural Sciences, 27(4), 407-413.
  • Erbaş, M., Certel, M., & Uslu, M. (2005). Some chemical properties of white lupin seeds (Lupinus albus L.). Food Chemistry, 89(3), 341-345.
  • Ercan, L., & Dogru, M. (2022). Determination of Antimicrobial Activity of Nasturtium officinale and Its Content of Volatile Organic Compounds and Fatty Acids. Ksu Tarim Ve Doga Dergisi-Ksu Journal of Agriculture and Nature, 25, 11-21. doi:10.18016/ksutarimdoga.vi.1001837
  • Gresta, F. W., M.; Prins, U.; Abberton, M.; Capraro, J.; Scarafoni, A.; Hill, G. (2017). Lupins in European Cropping Systems. In D. Murphy-Bokern, Stoddard, F., Watson, C., (Ed.), In Legumes in Cropping Systems (pp. 88-108). CABI: Wallingford, Oxfordshire.
  • Grundschober, F. (1979). Literature review of pulegone. Perfum. Flavorist, 4, 15–17.
  • Guo, X., Shang, W., Strappe, P., Zhou, Z., & Blanchard, C. (2018). Peptides derived from lupin proteins confer potent protection against oxidative stress. Journal of the Science of Food and Agriculture, 98 (14), 5225-5234.
  • Ishaq, A. R., El-Nashar, H. A., Younis, T., Mangat, M. A., Shahzadi, M., Ul Haq, A. S., & El-Shazly, M. (2022). Genus Lupinus (Fabaceae): a review of ethnobotanical, phytochemical and biological studies. Journal of Pharmacy and Pharmacology, 74(12), 1700-1717.
  • Kataoka, H., Lord, H. L., & Pawliszyn, J. (2000). Applications of solid-phase microextraction in food analysis. Journal of Chromatography A, 880(1-2), 35-62. Krutz, L., Senseman, S., & Sciumbato, A. (2003). Solid-phase microextraction for herbicide determination in environmental samples. Journal of Chromatography A, 999(1-2), 103-121.
  • Kumar, P., Mahato, D. K., Kamle, M., Borah, R., Sharma, B., Pandhi, S., Tripathi, V., Yadav, H. S., Devi, S., & Patil, U. (2021). Pharmacological properties, therapeutic potential, and legal status of Cannabis sativa L.: An overview. Phytotherapy Research, 35(11), 6010-6029.
  • Lucas, M. M., Stoddard, F. L., Annicchiarico, P., Frías, J., Martinez-Villaluenga, C., Sussmann, D., Duranti, M., Seger, A., Zander, P. M., & Pueyo, J. J. (2015). The future of lupin as a protein crop in Europe. Frontiers in Plant Science, 6, 705.
  • Mohamed, A., & Rayas-Duarte, P. (1995). Composition of Lupinus albus. Cereal Chemistry, 72(6), 643-647.
  • Muselli, A., Pau, M., Desjobert, J.-M., Foddai, M., Usai, M., & Costa, J. (2009). Volatile constituents of Achillea ligustica All. by HS-SPME/GC/GC-MS. Comparison with essential oils obtained by hydrodistillation from Corsica and Sardinia. Chromatographia, 69(5), 575-585.
  • Nasir, M., Sidhu, J. S., & Sogi, D. S. (2022). Processing and Nutritional Profile of Mung Bean, Black Gram, Pigeon Pea, Lupin, Moth Bean, and Indian Vetch. Dry Beans and Pulses: Production, Processing, and Nutrition, 431-452.
  • National Center for Biotechnology Information. (2022). PubChem Compound Summary for CID 7406, Cumene. Retrieved December 28 from https://pubchem.ncbi.nlm.nih.gov/compound/Cumene#section=Use-and-Manufacturing
  • Nissen, L., Zatta, A., Stefanini, I., Grandi, S., Sgorbati, B., Biavati, B., & Monti, A. (2010). Characterization and antimicrobial activity of essential oils of industrial hemp varieties (Cannabis sativa L.). Fitoterapia, 81(5), 413-419.
  • Pascual, H. (2004). Lupinus mariae-josephi (Fabaceae), nueva y sorprendente especie descubierta en España. Anales del Jardín Botánico de Madrid. Pereira, A., Ramos, F., & Sanches Silva, A. (2022). Lupin (Lupinus albus L.) Seeds: Balancing the Good and the Bad and Addressing Future Challenges. Molecules, 27(23), 8557.
  • Russo, E. B. (2011). Taming THC: potential cannabis synergy and phytocannabinoid‐terpenoid entourage effects. British journal of pharmacology, 163(7), 1344-1364.
  • Shaaban, A., Al-Elwany, O. A., Abdou, N. M., Hemida, K. A., El-Sherif, A., Abdel-Razek, M. A., Semida, W. M., Mohamed, G. F., El-Mageed, A., & Taia, A. (2022). Filter mud enhanced yield and soil properties of water-stressed Lupinus termis L. in saline calcareous soil. Journal of Soil Science and Plant Nutrition, 22(2), 1572-1588.
  • Sirtori, C. R., Triolo, M., Bosisio, R., Bondioli, A., Calabresi, L., De Vergori, V., Gomaraschi, M., Mombelli, G., Pazzucconi, F., & Zacherl, C. (2012). Hypocholesterolaemic effects of lupin protein and pea protein/fibre combinations in moderately hypercholesterolaemic individuals. British Journal of Nutrition, 107(8), 1176-1183.
  • Sullivan, J. B., Rumack, B. H., Thomas, H., Peterson, R. G., & Bryson, P. (1979). Pennyroyal oil poisoning and hepatotoxicity. Jama, 242(26), 2873-2874.
  • Świ\cecicki, W., Świ\cecicki, W. K., & Wolko, B. (1996). Lupinus anatolicus — a new lupin species of the old world. Genetic Resources and Crop Evolution, 43(2), 109-117. Święcicki, W., Kroc, M., & Kamel, K. A. (2015). Lupins. In Grain Legumes (pp. 179-218). Springer.
  • Święcicki, W., Wolko, B., & Naganowska, B. (2002). Lupinus anatolicus and L.× hispanicoluteus-morphological, biochemical and cytological characterization. Broad variation and precise characterization-limitation for the future. Proceedings of the XVIth EUCARPIA Genetic Resources Section workshop, Poznań, Poland, 16-20 May 2001.
  • Toluene Synopsis. (1990). Toluene Chemical Product Synopsis. Mannsville Chemical Products Corp. In Asbury Park, NJ. March 1990.
  • Ulrich, S. (2000). Solid-phase microextraction in biomedical analysis. Journal of Chromatography A, 902(1), 167-194.
  • Van de Noort, M. (2017). Lupin: An important protein and nutrient source. In Sustainable protein sources (pp. 165-183). Elsevier.
  • Yorgancılar, M., Babaoglu, M., Hakki, E. E., & Atalay, E. (2009). Determination of the relationship among Old World Lupin (Lupinus sp.) species using RAPD and ISSR markers. African Journal of Biotechnology, 8(15), 3524-3530.
  • Yorgancılar, M., & Bilgiçli, N. (2014). Chemical and nutritional changes in bitter and sweet lupin seeds (Lupinus albus L.) during bulgur production. Journal of food science and technology, 51(7), 1384-1389.

Bazı Acıbakla Genotiplerine Ait Ucucu Bileşiklerin SPME GC-MS Yöntemiyle Karakterizasyonu

Year 2023, Volume: 26 Issue: 4, 870 - 877, 31.08.2023

Ela Nur Şimşek Sezer , Mustafa Yorgancılar , Tuna Uysal

https://doi.org/10.18016/ksutarimdoga.vi.1205424

Abstract

Bu çalışmada, üç Lupinus albus L. ve iki L. angustifolius L. genotipi GC-MS ve SPME teknikleri kullanılarak uçucu veya yarı uçucu maddeler açısından araştırılmış ve karşılaştırılmıştır. Bu amaçla acı bakla tohumları el değirmeni yardımıyla öğütülmüş ve bu toz, ham madde içeriğinin belirlenmesinde kullanılmıştır. Bu acı bakla genotiplerinde yaklaşık olarak 102 bileşik ilk defa tanımlanmıştır. Bu bileşiklerden başlıcaları; benzene-methyl (1-methyl ethyl), 5-Allyl-4-(1-(p-aminophenyl) ethylidenehyl, 2-propen-1-ol, 3-phenyl-, m-Mentha-4,8, diene-(1S,3S)-(+), gamma terpinene dir. Bu bileşiklerin farklı genotiplerde ve farklı oranlarda bulunduğu tespit edilmiştir. Sonuç olarak, bitkilerden veya bitki parçalarından gelen aktif maddeleri ve olası potansiyellerini ortaya koymayı amaçlayan bu tür çalışmalar, gelecekte yapılacak daha spesifik çalışmalar açısından büyük önem taşımaktadır.

Keywords

Acı bakla GC-MS Katı fazlı mikro ekstraksiyon Ucucu bileşikler

References

  • Abraham, E. M., Ganopoulos, I., Madesis, P., Mavromatis, A., Mylona, P., Nianiou-Obeidat, I., Parissi, Z., Polidoros, A., Tani, E., & Vlachostergios, D. (2019). The use of lupin as a source of protein in animal feeding: Genomic tools and breeding approaches. International Journal of Molecular Sciences, 20(4), 851.
  • Arnoldi, A., Boschin, G., Zanoni, C., & Lammi, C. (2015). The health benefits of sweet lupin seed flours and isolated proteins. Journal of Functional Foods, 18, 550-563.
  • Arthur, C. L., & Pawliszyn, J. (1990). Solid-Phase Microextraction with Thermal-Desorption Using Fused-Silica Optical Fibers. Analytical Chemistry, 62(19), 2145-2148.
  • Bähr, M., Fechner, A., Kiehntopf, M., & Jahreis, G. (2015). Consuming a mixed diet enriched with lupin protein beneficially affects plasma lipids in hypercholesterolemic subjects: A randomized controlled trial. Clinical Nutrition, 34(1), 7-14.
  • Bhardwaj, H. L., & Hamama, A. A. (2012). Cultivar and growing location effects on white lupin immature green seeds. Journal of Agricultural Science, 4(2), 135.
  • Bicchi, C., Cordero, C., Liberto, E., Rubiolo, P., & Sgorbini, B. (2004). Automated headspace solid-phase dynamic extraction to analyse the volatile fraction of food matrices. Journal of Chromatography A, 1024(1-2), 217-226.
  • Bicchi, C., Drigo, S., & Rubiolo, P. (2000). Influence of fibre coating in headspace solid-phase microextraction–gas chromatographic analysis of aromatic and medicinal plants. Journal of Chromatography A, 892(1-2), 469-485.
  • Brummund, M., & Święcicki, W. (2011). The recent history of lupin in agriculture. Lupin crops: an apportunity for today a promise for the future. Proceedings of the 13th International Lupin Conference, Poznan, Poland, 6-12 June 2011.
  • Cardoso, D., Pennington, R. T., De Queiroz, L., Boatwright, J. S., Van Wyk, B.-E., Wojciechowski, M., & Lavin, M. (2013). Reconstructing the deep-branching relationships of the papilionoid legumes. South African Journal of Botany, 89, 58-75.
  • Cowling, W. A., Buirchell, B. J., & Tapia, M. E. (1998). Lupin. Lupinus L. International Plant Genetic Resources Institute (IPGRI).
  • Cowling, W. A., Huyghe, C., & Swiecicki, W. (1998). Lupin breeding. Lupins as crop plants: biology, production and utilization., 93-120.
  • Culvenor, C., & Petterson, D. (1986). Lupin toxins-alkaloids and phomopsins. 4. International Lupin Conference, p. 188-198, Geraldton, (WA) Australia, 17-22 Aug 1986.
  • Duranti, M., Consonni, A., Magni, C., Sessa, F., & Scarafoni, A. (2008). The major proteins of lupin seed: characterisation and molecular properties for use as functional and nutraceutical ingredients. Trends in Food Science & Technology, 19(12), 624-633.
  • Elma, F., Çetin, H., Yorgancılar, M., & Acar, R. (2021). Detection of Metabolite Content in Local Bitter White Lupin Seeds (Lupinus albus L.) and Acaricidal and Insecticidal Effect of its Seed Extract. Journal of Agricultural Sciences, 27(4), 407-413.
  • Erbaş, M., Certel, M., & Uslu, M. (2005). Some chemical properties of white lupin seeds (Lupinus albus L.). Food Chemistry, 89(3), 341-345.
  • Ercan, L., & Dogru, M. (2022). Determination of Antimicrobial Activity of Nasturtium officinale and Its Content of Volatile Organic Compounds and Fatty Acids. Ksu Tarim Ve Doga Dergisi-Ksu Journal of Agriculture and Nature, 25, 11-21. doi:10.18016/ksutarimdoga.vi.1001837
  • Gresta, F. W., M.; Prins, U.; Abberton, M.; Capraro, J.; Scarafoni, A.; Hill, G. (2017). Lupins in European Cropping Systems. In D. Murphy-Bokern, Stoddard, F., Watson, C., (Ed.), In Legumes in Cropping Systems (pp. 88-108). CABI: Wallingford, Oxfordshire.
  • Grundschober, F. (1979). Literature review of pulegone. Perfum. Flavorist, 4, 15–17.
  • Guo, X., Shang, W., Strappe, P., Zhou, Z., & Blanchard, C. (2018). Peptides derived from lupin proteins confer potent protection against oxidative stress. Journal of the Science of Food and Agriculture, 98 (14), 5225-5234.
  • Ishaq, A. R., El-Nashar, H. A., Younis, T., Mangat, M. A., Shahzadi, M., Ul Haq, A. S., & El-Shazly, M. (2022). Genus Lupinus (Fabaceae): a review of ethnobotanical, phytochemical and biological studies. Journal of Pharmacy and Pharmacology, 74(12), 1700-1717.
  • Kataoka, H., Lord, H. L., & Pawliszyn, J. (2000). Applications of solid-phase microextraction in food analysis. Journal of Chromatography A, 880(1-2), 35-62. Krutz, L., Senseman, S., & Sciumbato, A. (2003). Solid-phase microextraction for herbicide determination in environmental samples. Journal of Chromatography A, 999(1-2), 103-121.
  • Kumar, P., Mahato, D. K., Kamle, M., Borah, R., Sharma, B., Pandhi, S., Tripathi, V., Yadav, H. S., Devi, S., & Patil, U. (2021). Pharmacological properties, therapeutic potential, and legal status of Cannabis sativa L.: An overview. Phytotherapy Research, 35(11), 6010-6029.
  • Lucas, M. M., Stoddard, F. L., Annicchiarico, P., Frías, J., Martinez-Villaluenga, C., Sussmann, D., Duranti, M., Seger, A., Zander, P. M., & Pueyo, J. J. (2015). The future of lupin as a protein crop in Europe. Frontiers in Plant Science, 6, 705.
  • Mohamed, A., & Rayas-Duarte, P. (1995). Composition of Lupinus albus. Cereal Chemistry, 72(6), 643-647.
  • Muselli, A., Pau, M., Desjobert, J.-M., Foddai, M., Usai, M., & Costa, J. (2009). Volatile constituents of Achillea ligustica All. by HS-SPME/GC/GC-MS. Comparison with essential oils obtained by hydrodistillation from Corsica and Sardinia. Chromatographia, 69(5), 575-585.
  • Nasir, M., Sidhu, J. S., & Sogi, D. S. (2022). Processing and Nutritional Profile of Mung Bean, Black Gram, Pigeon Pea, Lupin, Moth Bean, and Indian Vetch. Dry Beans and Pulses: Production, Processing, and Nutrition, 431-452.
  • National Center for Biotechnology Information. (2022). PubChem Compound Summary for CID 7406, Cumene. Retrieved December 28 from https://pubchem.ncbi.nlm.nih.gov/compound/Cumene#section=Use-and-Manufacturing
  • Nissen, L., Zatta, A., Stefanini, I., Grandi, S., Sgorbati, B., Biavati, B., & Monti, A. (2010). Characterization and antimicrobial activity of essential oils of industrial hemp varieties (Cannabis sativa L.). Fitoterapia, 81(5), 413-419.
  • Pascual, H. (2004). Lupinus mariae-josephi (Fabaceae), nueva y sorprendente especie descubierta en España. Anales del Jardín Botánico de Madrid. Pereira, A., Ramos, F., & Sanches Silva, A. (2022). Lupin (Lupinus albus L.) Seeds: Balancing the Good and the Bad and Addressing Future Challenges. Molecules, 27(23), 8557.
  • Russo, E. B. (2011). Taming THC: potential cannabis synergy and phytocannabinoid‐terpenoid entourage effects. British journal of pharmacology, 163(7), 1344-1364.
  • Shaaban, A., Al-Elwany, O. A., Abdou, N. M., Hemida, K. A., El-Sherif, A., Abdel-Razek, M. A., Semida, W. M., Mohamed, G. F., El-Mageed, A., & Taia, A. (2022). Filter mud enhanced yield and soil properties of water-stressed Lupinus termis L. in saline calcareous soil. Journal of Soil Science and Plant Nutrition, 22(2), 1572-1588.
  • Sirtori, C. R., Triolo, M., Bosisio, R., Bondioli, A., Calabresi, L., De Vergori, V., Gomaraschi, M., Mombelli, G., Pazzucconi, F., & Zacherl, C. (2012). Hypocholesterolaemic effects of lupin protein and pea protein/fibre combinations in moderately hypercholesterolaemic individuals. British Journal of Nutrition, 107(8), 1176-1183.
  • Sullivan, J. B., Rumack, B. H., Thomas, H., Peterson, R. G., & Bryson, P. (1979). Pennyroyal oil poisoning and hepatotoxicity. Jama, 242(26), 2873-2874.
  • Świ\cecicki, W., Świ\cecicki, W. K., & Wolko, B. (1996). Lupinus anatolicus — a new lupin species of the old world. Genetic Resources and Crop Evolution, 43(2), 109-117. Święcicki, W., Kroc, M., & Kamel, K. A. (2015). Lupins. In Grain Legumes (pp. 179-218). Springer.
  • Święcicki, W., Wolko, B., & Naganowska, B. (2002). Lupinus anatolicus and L.× hispanicoluteus-morphological, biochemical and cytological characterization. Broad variation and precise characterization-limitation for the future. Proceedings of the XVIth EUCARPIA Genetic Resources Section workshop, Poznań, Poland, 16-20 May 2001.
  • Toluene Synopsis. (1990). Toluene Chemical Product Synopsis. Mannsville Chemical Products Corp. In Asbury Park, NJ. March 1990.
  • Ulrich, S. (2000). Solid-phase microextraction in biomedical analysis. Journal of Chromatography A, 902(1), 167-194.
  • Van de Noort, M. (2017). Lupin: An important protein and nutrient source. In Sustainable protein sources (pp. 165-183). Elsevier.
  • Yorgancılar, M., Babaoglu, M., Hakki, E. E., & Atalay, E. (2009). Determination of the relationship among Old World Lupin (Lupinus sp.) species using RAPD and ISSR markers. African Journal of Biotechnology, 8(15), 3524-3530.
  • Yorgancılar, M., & Bilgiçli, N. (2014). Chemical and nutritional changes in bitter and sweet lupin seeds (Lupinus albus L.) during bulgur production. Journal of food science and technology, 51(7), 1384-1389.
There are 40 citations in total.

Details

Primary Language Turkish
Subjects Agricultural, Veterinary and Food Sciences
Journal Section RESEARCH ARTICLE
Authors

Ela Nur Şimşek Sezer 0000-0003-2805-7204

Mustafa Yorgancılar 0000-0003-4938-8547

Tuna Uysal 0000-0001-9968-5633

Early Pub Date May 15, 2023
Publication Date August 31, 2023
Submission Date November 15, 2022
Acceptance Date January 4, 2023
Published in Issue Year 2023Volume: 26 Issue: 4

Cite

APA Şimşek Sezer, E. N., Yorgancılar, M., & Uysal, T. (2023). Bazı Acıbakla Genotiplerine Ait Ucucu Bileşiklerin SPME GC-MS Yöntemiyle Karakterizasyonu. Kahramanmaraş Sütçü İmam Üniversitesi Tarım Ve Doğa Dergisi, 26(4), 870-877. https://doi.org/10.18016/ksutarimdoga.vi.1205424
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