Antimicrobial activities of Scorzonera ketzkhowelii Sosn. ex Grossh. (Asteraceae) and determination of natural compounds by LC-HRMS analysis

Abstract

Background and Aims: Scorzonera ketzkhowelii Sosn. ex Grossh. (Asteraceae) was reported as a new species in the Flora of Turkey in 2010. However, there have been no prior biological or chemical investigations conducted. Methods: This study aims to investigate the antimicrobial activities of the petroleum ether, dichloromethane, ethyl acetate, and n-butanol fractions derived from S. ketzkhowelii, and determination of secondary metabolites by Liquid Chromatography with High Resolution Mass Spectrometry (LC-HRMS) analysis on the most active antimicrobial fractions. Results: Notably, all of the fractions demonstrated antimicrobial activity against selected microorganisms, with the dichloromethane fraction of the aerial part exhibiting a higher inhibition of microbial growth compared to the other extracts. The findings of our study revealed the presence of several phenolic compounds in the dichloromethane fractions from both the aerial and subaerial parts, including 3,4-dihydroxybenzaldehyde, salicylic acid, dihydrocaffeic acid, caffeic acid, caffeic acid phenethyl ester, chlorogenic acid, quercetin, hyperoside, naringenin, apigenin, hispidulin, hispidulin 7-glucoside, chrycin, emodin, and carnosic acid. Furthermore, dichloromethane fraction of the aerial parts contained additional phenolic compounds such as homogentisic acid, verbascoside, (+)-trans taxifolin, apigenin 7-glucoside, luteolin, orientin, and chrysoeriol. Conclusion: The plant’s demonstrated antimicrobial attributes and the diverse range of phenolic compounds it contains present it as a promising subject for continued research and potential applications within the realms of medicine and pharmaceuticals. Further exploration of its bioactivity and potential health benefits may reveal novel avenues for its practical utilization.

Keywords

• Scorzonera ketzkhowelii
• Asteraceae
• antimicrobial activity
• LC-HRMS
• phenolic compounds

References

1. Altundağ, E., & Öztürk, M. (2011). Ethnomedicinal studies on the plant resources of east Anatolia, Turkey. Procedia - Social and Behavioral Sciences, 19(June), 756-777. Retrieved from https://doi.org/10.1016/j.sbspro.2011.05.195 google scholar
2. Âvila, H. P., Smânia, E. de F. A., Monache, F. D., & Smânia, A. (2008). Structure-activity relationship of antibacterial chalcones. Bioor-ganic & Medicinal Chemistry, 16(22), 9790-9794. Retrieved from https://doi.org/10.1016/j.bmc.2008.09.064 google scholar
3. Bahadır Acıkara, Ö., Çitoğlu, G. S., Dall’Acqua, S., Smejkal, K., Cvacka, J., & Zemlicka, M. (2012). A new triter-pene from Scorzonera latifolia (Fisch. and Mey.) DC. Nat-ural Product Research, 26(20), 1892-1897. Retrieved from https://doi.org/10.1080/14786419.2011.625644 google scholar
4. Batovska, D., Parushev, S., Stamboliyska, B., Tsvetkova, I., Ni-nova, M., & Najdenski, H. (2009). Examination of growth inhibitory properties of synthetic chalcones for which an-tibacterial activity was predicted. European Journal of Medicinal Chemistry, 44(5), 2211-2218. Retrieved from https://doi.org/10.1016/j.ejmech.2008.05.010 google scholar
5. Ben Abdelkader, H., Salah, K. B. H., Liouane, K., Boussaada, O., Gafsi, K., Mahjoub, M. A., . . . Mighri, Z. (2010). Antimicrobial activity of Rhaponticum acaule and Scorzonera undulata growing wild in Tunisia. African Journal of Microbiology Research, 4(19), 1954-1958. google scholar
6. CLSI. (2000). Reference method for Broth dilution antifungal sus-ceptibility testing of yeasts: approved standard M27-A NCCLS. Wayne (PA): CLSI. google scholar
7. CLSI. (2006). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically: approved standard M7-A5. Wayne (PA): CLSI. google scholar
8. Coşkunçelebi, K., Makbul, S., Gültepe, M., Okur, S., & Güzel, M. E. (2015). A conspectus of Scorzonera s.l. in Turkey. Turkish Journal of Botany, 39(1), 76-87. Retrieved from https://doi.org/10.3906/bot-1401-10 google scholar

9. Erik, İ., Yalçın, C. Ö., Coşkunçelebi, K., Alpay Karaoğlu, Ş., & Yaylı, N. (2022). Phytochemical Analysis and Antimicrobial Activities of Scorzonera Aucheriana. SSRN. google scholar
10. Göç, F., & Mat, A. (2019). Türkiye’de Yanık Tedavisinde Geleneksel Olarak Kullanılan Bitkiler. Sağlık Bilimlerinde İleri Araştırmalar Dergisi, 2(1). google scholar
11. Granica, S., & Zidorn, C. (2015). Phenolic compounds from aerial parts as chemosystematic markers in the Scorzonerinae (Aster-aceae). Biochemical Systematics and Ecology, 58, 102-113. Re-trieved from https://doi.org/10.1016/j.bse.2014.11.005 google scholar
12. Hamzaoğlu, E., Aksoy, A., Martin, E., Pınar, N. M., & Çölgeçen, H. (2010). A new record for the flora of Turkey: Scorzonera ket-zkhovelii Grossh. (Asteraceae). Turkish Journal of Botany , 34(1), 57-61. google scholar
13. Makbul, S. (2012). Scorzonera L. In A. Güner, S. Aslan, T. Ekim, M. Vural, & M. T. Babaç (Eds.), Türkiye Bitkileri Listesi (Damarlı Bitkiler) (pp. 195-199). İstanbul: Nezahat Gökyiğit Botanik Bahçesi ve Flora Araştırmaları Derneği. google scholar
14. Miklasinska-Majdanik, M., Kçpa, M., Wojtyczka, R., Idzik, D., W^sik, T. (2018). Phenolic Compounds Diminish Antibiotic Resistance of Staphylococcus Aureus Clinical Strains. International Journal of Environmental Research and Public Health, 15(10), 2321. Re-trieved from https://doi.org/10.3390/yerph15102321 google scholar
15. Nadiroğlu, M., Behçet, L., & Çakılcıoğlu, U. (2019). An ethnobotani-cal survey of medicinal plants in karlıova (Bingöl-turkey). Indian Journal ofTraditional Knowledge, 18(1), 76-87. google scholar
16. Nielsen, S. F., Boesen, T., Larsen, M., Sch0nning, K., & Kro-mann, H. (2004). Antibacterial chalcones—bioisosteric replacement of the 4-hydroxy group. Bioorganic & Medicinal Chemistry, 12(11), 3047-3054. Retrieved from https://doi.org/10.1016/j.bmc.2004.03.071 google scholar
17. Şahin, H., Boğa, M., & Sarı, A. (2022). Terpenoid and Fatty Acid Profiling along with Anti-Tyrosinase and Anti-Urease Potentials of Scorzonera pygmaea Sibth. & Sm. an Endemic Plant of Turkey. Chemistry & Biodiversity, 19(2), e202100758. Retrieved from https://doi.org/https://doi.org/10.1002/cbdv.202100758 google scholar
18. Şahin, H., Sarı, A., Özsoy, N., Özbek Çelik, B., & Koyuncu, O. (2020a). Phenolic compounds and bioactivity of Scorzonera pygmaea Sibth. & Sm. aerial parts: In vitro antioxidant, anti-inflammatory and antimicrobial activities. Istanbul Journal of Pharmacy, 50(3), 294-299. google scholar
19. Şahin, H., Sarı, A., Özsoy, N., Özbek Çelik, B., & Koyuncu, O. (2020b). Two new phenolic compounds and some biolog ical activities of Scorzonera pygmaea Sibth. & Sm. subaerial parts. Natural Product Research, 34(5), 621-628. Retrieved from https://doi.org/10.1080/14786419.2018.1493585 google scholar
20. Sarı, A., Şahin, H., Özsoy, N., & Özbek Çelik, B. (2019). Phenolic compounds and in vitro antioxidant, anti-inflammatory, antimi-crobial activities of Scorzonera hieraciifolia Hayek roots. South African Journal of Botany, 125, 116-119. Retrieved 14 August 2022 from https://doi.org/10.1016/J.SAJB.2019.07.009 google scholar
21. Sarı, Aynur. (2012). Phenolic compounds from Scorzonera latifolia Phenolic compounds from Scorzonera latifolia (Fisch. & Mey.) DC. Natural Product Research, 26(1), 50-55. Retrieved from https://doi.org/10.1080/14786419.2010.533666 google scholar
22. Sarı, Aynur, Özbek, B., & Özgökçe, F. (2009). Antimicrobial Activities of Two Scorzonera Species Growing in Turkey. Asian Journal of Chemistry, 21(6), 4785-4788. google scholar
23. Suresh Babu, K., Hari Babu, T., Srinivas, P. V., Sastry, B. S., Hara Kishore, K., Murty, U. S. N., & Madhusudana Rao, J. (2005). Synthesis and in vitro study of novel 7-O-acyl deriva-tives of Oroxylin A as antibacterial agents. Bioorganic & Medic-inal Chemistry Letters, 15(17), 3953-3956. Retrieved from https://doi.org/10.1016/j.bmcl.2005.05.045 google scholar
24. Sweidan, A., El-Mestrah, M., Kanaan, H., Dandache, I., Merhi, F., & Chokr, A. (2020). Antibacterial and antibiofilm ac-tivities of Scorzonera mackmeliana. Pakistan Journal of Pharmaceutical Sciences, 33(1), 199-206. Retrieved from http://europepmc.org/abstract/MED/32122849 google scholar
25. Tako, M., Kerekes, E. B., Zambrano, C., Kotogan, A., Papp, T., Krisch, J., & Vagvölgyi, C. (2020). Plant Phenolics and Phenolic-Enriched Extracts as Antimicrobial Agents against Food-Contaminating Microorganisms. Antioxidants, 9(2), 165. Retrieved from https://doi.org/10.3390/antiox9020165 google scholar
26. Tuzlacı, E. (2016). Türkiye Bitkileri Geleneksel İlaç Rehberi. İstanbul: Istanbul Tıp Kitabevi. google scholar
27. Ugur, A., Sarac, N., Ceylan, O., Duru, M. E., & Beyatli, Y. (2010). Chemical Composition of Endemic Scorzonera sandrasica and Studies on the Antimicrobial Activity Against Multiresistant Bac-teria. Journal of Medicinal Food, 13(3), 635-639. Retrieved from https://doi.org/10.1089/jmf.2008.0312 google scholar
28. Zidorn, C., Ellmerer-Müller, E., & Stuppner, H. (2000). Sesquiter-penoids from Scorzonera hispanica L. . Pharmazie, 55(7), 550-551. google scholar