GC-MS/MS and 1H-NMR analysis of endemic Campanula baskilensis Behçet leaf fractions

Year 2024, Volume: 7 Issue: 1, 48 - 57, 06.07.2024

Sarmad Marah , Tevfik Ozen , İbrahim Demirtas , Yaşar İpek , Fatih Gül , Lütfi Behçet

https://doi.org/10.38093/cupmap.1477900

https://izlik.org/JA29WH55EP

Abstract

In this research, 1H-NMR and CG-MS/MS spectrophotometric techniques were used to elucidate the chemical profile of leaf fractions of Campanula baskilensis Behçet. A column chromatography system was used for the fractionation of the crude extract. Fifteen separate fractions were obtained throughout the fractionation procedure. Thirty-nine molecules were identified using both spectrometry techniques. Thirty-one compounds of these molecules were identified, and eight compounds were listed as unknown. For lupeyl acetate, it was determined as 77.80% in Fr6-2, 63.21% in Fr3-3, 43.81% in Fr4-3, and for 1-octadecene, it was determined as 36.23% in Fr3-2 and 32.14% in Fr4-1. Additionally, levels of 34.88% for hexadecanoic acid and 34.05% for borneol were recorded at Fr8. It is also noteworthy that, as an unknown molecule, Fr3-4 is formed at a rate of 97.28%. Molecular structures such as hexadecanoic acid (methyl palmitate), benzoic acid, eicosanoic acid, limonene, borneol, and hentriacontanol were supported by 1H-NMR analysis.
Understanding the chemical constituents of C. baskilensis plant will provide opportunities to suggest broader research in the future. The identified molecules can be the subject of isolation and further original models for various in-vitro and in-silico bioassays or effective drug development and application.

Keywords

C. baskilensis , GC-MS/MS , ¹H-NMR , Fractionation

Project Number

PYO.FEN.1904.20.003

Thanks

Ondokuz Mayıs Üniversitesi, BAPKOB

References

• 1. Yildirim, H.; Şentürk, O.; Özdöl, T.; Pirhan, A. F., 2019. A new bellflower, Campanula phitosiana sp. nov. (Campanulaceae) from Western Anatolia, Turkey. Phytotaxa. 399 (1), 25-36.
• 2. Anestis, I.; Pipinis, E.; Kostas, S.; Papaioannou, E.; Karapatzak, E.; Dariotis, E.; Tsoulpha, P.; Koundourakis, E.; Chatzileontari, E.; Tsoktouridis, G., 2023. GIS-Facilitated Germination of Stored Seeds from Five Wild-Growing Populations of Campanula pelviformis Lam. and Fertilization Effects on Growth, Nutrients, Phenol Content and Antioxidant Potential. Horticulturae. 9 (8), 877.
• 3. Mohammed, F. S.; Uysal, I.; Sabik, A. E.; Dogan, M.; Sevindik, M., 2023. Total Phenolic and Flavonoid Contents, Antimicrobial and Antioxidant Potentials Of Campanula Strigosa Banks & Sol. Journal of microbiology, biotechnology and food sciences. e10057-e10057.
• 4. Brandt, K.; Dötterl, S.; Francke, W.; Ayasse, M.; Milet-Pinheiro, P., 2017. Flower Visitors of Campanula: Are Oligoleges More Sensitive to Host-Specific Floral Scents Than Polyleges?. J. Chem. Ecol. 43 (1), 4-12.
• 5. Kim, H.-J.; Son, D. C.; Kim, H.-J.; Choi, K.; Oh, S.-H.; Kang, S.-H., 2017. The chemotaxonomic classification of Korean Campanulaceae based on triterpene, sterol, and polyacetylene contents. Biochemical systematics and ecology. 74, 11-18.
• 6. Newman, D. J.; Cragg, G. M., 2016. Newman, D. J.; Cragg, G. M., J. Nat. Prod. 2016, 79 (3), 629-661. J. Nat. Prod. 79 (3), 629-661.
• 7. Sarıkaya, A. G.; Kavaklı, S. A., 2020. Some morphological and phenological characteristics and volatile components of Campanula rapunculus L. var. rapunculus. International Journal of Biology and Chemistry. 13 (2), 38-45.
• 8. Wen, L.; Guo, X.; Liu, R. H.; You, L.; Abbasi, A. M.; Fu, X., 2015. Phenolic contents and cellular antioxidant activity of Chinese hawthorn "Crataegus pinnatifida". Food Chem. 186, 54-62. 9. Liu, R. H., 2013. Health-promoting components of fruits and vegetables in the diet. Adv. Nutr. 4 (3), 384S-392S.
• 10. Eberhardt, M. V.; Lee, C. Y.; Liu, R. H., 2000. Antioxidant activity of fresh apples. Nature. 405 (6789), 903-904. 11. Sun, J.; Chu, Y.-F.; Wu, X.; Liu, R. H., 2002. Antioxidant and antiproliferative activities of common fruits. Journal of agricultural and food chemistry. 50 (25), 7449-7454.
• 12. Politeo, O.; Skocibusic, M.; Burcul, F.; Maravic, A.; Carev, I.; Ruscic, M.; Milos, M., 2013. Campanula portenschlagiana Roem. et Schult.: Chemical and Antimicrobial Activities. Chem. Biodivers. 10 (6), 1072-1080. 13. Behçet, L.; İlçim, A., 2018. Campanula baskilensis sp. nov. (Campanulaceae), a new chasmophyte from Turkey with unusual capsule dehiscence. Nord. J. Bot. 36 (10), e01940.
• 14. Başar, Y.; Yenigün, S.; İpek, Y.; Behçet, L.; Gül, F.; Özen, T.; Demirtaş, İ., 2023. DNA protection, molecular docking, enzyme inhibition and enzyme kinetic studies of 1,5,9-epideoxyloganic acid isolated from Nepeta aristata with bio-guided fractionation. J Biomol Struct Dyn. 1-14.
• 15. Ipek, Y.; Ozen, T.; Demirtas, I., 2017. Extraction, purification, characterization and antioxidant activities of heat-resistance phenolic compounds from lemon pulp. Trends in Phytochemical Research. 1 (4), 199-206.
• 16. Yenigun, S.; Basar, Y.; Gul, F.; Marah, S.; Behcet, L.; Demirtas, I.; Ozen, T., 2024. Chemical Constituents and Bioactivities of Nepeta Taxa Essential Oils from Turkey: Principal Component Analysis, Molecular Docking Study, Molecular Dynamics, MM-PBSA and Drug-Likeness Estimation. ChemistrySelect. 9 (18), e202400583.
• 17. Ozen, T.; Telci, I.; Gul, F.; Demirtas, I., 2017. Chemical analyzes and antioxidant activities of essential oils of four wild Mentha species growing in the Tokat and its districts. Int. J. Chem. Technol. 1 (1), 46-57.
• 18. Yenigun, S.; Ipek, Y.; Marah, S.; Demirtas, I.; Ozen, T., 2023. DNA protection, molecular docking, antioxidant, antibacterial, enzyme inhibition, and enzyme kinetic studies for parietin, isolated from Xanthoria parietina (L.) Th. Fr. Journal of Biomolecular Structure and Dynamics. 1-15.
• 19. Sinek, K.; Iskender, N. Y.; YAYLI, N., 2012. Antimicrobial Activity and Chemical Composition of the Essential Oil from Campanula glomerata L. Subsp Hispida (Witasek) Hayek. Asian J. Chem. 24 (5).
• 20. Tosun, G.; Kahriman, N.; Genç, H.; Karaoglu, S. A.; Yayli, N., 2011. Chemical Composition and Biological Activity of the Essential Oil of Campanula olympica Boiss. Asian J. Chem. 23 (6), 2389.
• 21. Dong, Z.; Zhao, Y.; Chen, J.; Chang, M.; Wang, X.; Jin, Q.; Wang, X., 2021. Dong, Z., Zhao, Y., Chen, J., Chang, M., Wang, X., Jin, Q., & Wang, X. (2021). Enzymatic lipophilization of d-borneol extracted from Cinnamomum camphora chvar. Borneol seed. LWT, 148, 111801.
• 22. Wang, X.-M.; Zhang, J.; Wu, L.-H.; Zhao, Y.-L.; Li, T.; Li, J.-Q.; Wang, Y.-Z.; Liu, H.-G., 2014. A mini-review of chemical composition and nutritional value of edible wild-grown mushroom from China. Food Chem. 151, 279-285.
• 23. Mir, M. A.; Ashraf, M. W.; Singh, P., 2021. Phytochemical isolation and Anti-inflammatory properties of various extracts of Lilium polyphyllum. Research Journal of Pharmacy and Technology. 14 (6), 3195-3201. 24. Kamboj, A.; Saluja, A. K., 2011. Isolation of stigmasterol and β-sitosterol from petroleum ether extract of aerial parts of Ageratum conyzoides (Asteraceae). Int. J. Pharm. Pharm. Sci. 3 (1), 94-96.
• 25. Wansi, J. D.; Nwozo, S. O.; Mbaze, L. M. a.; Devkota, K. P.; Moladje, S. M. D.; Fomum, Z. T.; Sewald, N., 2009. Wansi JD, Nwozo SO, Mbaze LM, Devkota KP, Moladje SMD, Fomum ZT, Sewald N (2009) Amides from the stem bark of Fagara macrophylla. Planta Med. 75:517–521.