Chemical compositions of Sideritis albiflora Hub. – Mor.

Yıl 2021, Cilt: 51 Sayı: 3, 378 - 385, 29.12.2021

Damla Kırcı , Nagehan Saltan , Fatih Göğer , Yavuz Bülent Köse , Betül Demirci

Öz

Background and Aims: Sideritis species (Lamiaceae) which are quite widespread in the Mediterranean region and represented by 46 species and 53 taxa in Turkey, are often used as a antirheumatic, anti-inflammatory, antimicrobial and diuretic remedies. Methods: In this study, the infusion (INF), essential oil (EO) and methanolic extract (ME) of chemical compounds prepared from aerial parts of Sideritis albiflora Hub.-Mor. (endemic) were investigated. Results: The presence of chlorogenic acid, verbascoside, forsythoside, apigenin glucoside, and isoscutellarein derivatives in the infusion and methanol extract of the plant was determined by LC-MS / MS analysis. In addition, the main constituents of the essential oil were found as germacrene D (23.5%), ß-caryophyllene (13.6%) and caryophylene oxide (8.0%) by GC / MS and GC / FID simultaneously. Conclusion: In this study, the essential oil, the methanolic extract and the infusion of S. albiflora species were prepared and their chemical compositions elucidated. It was determined that the essential oil chemical compound composition is rich in terms of the sesquiterpene group. Infusions of aerial parts of some Sideritis species have traditionally been used in the treatment of many diseases. Accordingly, the fact that the phenolic compounds of S. albiflora infusion have not been studied before increases the importance of this study. In addition, the therapeutic effect was shown to be related to major S. albiflora compounds, and the correlation between in vitro activity and ethnobotanical use was evaluated. The effective phenolic compounds contained in S. albiflora are thought to support the traditional uses of the plant.

Anahtar Kelimeler

Sideritis albiflora, infusion, polyphenolic compounds, methanolic extract, essential oil

Destekleyen Kurum

This study was supported by Anadolu University Scientific Research Projects Units

Proje Numarası

BAP1905S077

Kaynakça

• • Ahmad, V. U., Arshad, S., Bader, S., Ahmed, A., Iqbal, S., & Tareen, R. B. (2006). New phenethyl alcohol glycosides from Stachys parviflora. Journal of Asian Natural Products Research, 8(1-2), 105-111.
• • Aneva, I., Zhelev, P., Kozuharova, E., Danova, K., Nabavi, S. F., & Behzad, S. (2019). Genus Sideritis, section Empedoclia in southeastern Europe and Turkey–studies in ethnopharmacology and recent progress of biological activities. DARU Journal of Pharmaceutical Sciences, 27(1), 407-421.
• • Askun, T., Tumen, G., Satil, F., & Ates, M. (2009). Characterization of the phenolic composition and antimicrobial activities of Turkish medicinal plants. Pharmaceutical Biology, 47(7), 563-571.
• • Asnaashari, S., Delazar, A., Alipour, S. S., Nahar, L., Williams, A. S., Pasdaran, A. … Sarker, S. D. (2010). Chemical composition, freeradical- scavenging and insecticidal activities of the aerial parts of Stachys Byzantina, Journal of Asian Natural Products Research, 62(3), 653-662.
• • Axiotis, E., Petrakis, E. A., Halabalaki, M., & Mitakou, S. (2020). Phytochemical Profile and Biological Activity of Endemic Sideritis sipylea Boiss. in North Aegean Greek Islands. Molecules, 25(9), 2022. • Başer, K. H. C., & Kirimer, N. (2018). Essential oils of anatolian lamiaceae-An update. Natural Volatiles and Essential Oils, 5(4), 1-28.
• • Clifford, M. N., Knight, S., & Kuhnert, N. (2005). Discriminating between the six isomers of dicaffeoylquinic acid by LC-MS n. Journal of Agricultural and Food Chemistry, 53(10), 3821-3832.
• • Demirci, B., Dilmaç, E., Kırcı, D., İlhan, G., Demirci, F., Kiliç, C. S., & Duman, H. (2019). Chemical and antimicrobial characterization of essential oils obtained from aerial part, root and fruit of Ferulago longistylis Boiss., an endemic species. Natural Volatiles & Essential Oils, 7(1), 18-25.
• • Deveci, E., Tel‐Çayan, G., Duru, M. E., & Öztürk, M. (2019b). Phytochemical contents, antioxidant effects, and inhibitory activities of key enzymes associated with Alzheimer’s disease, ulcer, and skin disorders of Sideritis albiflora and Sideritis leptoclada. Journal of Food Biochemistry, 43(12), 1-11.
• • Deveci, E., Tel-Çayan, G., Usluer, Ö., & Duru, M. E. (2019a). Chemical composition, antioxidant, anticholinesterase and anti-tyrosinase activities of essential oils of two Sideritis species from Turkey. Iranian Journal of Pharmaceutical Research, 18(2), 903-913.
• • Ezer, N., Vila, R., Cañigueral, S., & Adzet, T. (1996). Essential oil composition of four Turkish species of Sideritis. Phytochemistry, 41(1), 203-205.
• • González-Burgos, E., Carretero, M. E., & Gómez-Serranillos, M. P. (2011). Sideritis spp.: Uses, chemical composition and pharmacological activities—A review. Journal of Ethnopharmacology, 135(2), 209-225.
• • Gozari, M., Alborz, M., El-Seedi, H. R., & Jassbi, A. R. (2020). Chemistry, biosynthesis and biological activity of terpenoids and meroterpenoids in bacteria and fungi isolated from different marine habitats. European Journal of Medicinal Chemistry, 210, 112957.
• • Guner, A., Aslan, S., Ekim, T., Vural, M., & Babaç, M. T. (2012). List plants of Turkey (vascular plants). İstanbul, Türkiye: Nezahat Gökyiğit Botanik Bahçesi ve Flora Araştırmaları Derneği Yayını.
• • Gürbüz, P., Martinez, A., Pérez, C., Martínez-González, L., Göger, F., & Ayran, İ. (2019). Potential anti-Alzheimer effects of selected Lamiaceae plants through polypharmacology on glycogen synthase kinase-3β, β-secretase, and casein kinase 1δ. Industrial Crops and Products, 138, 111431.
• • Güvenç, A., Houghton, P. J., Duman, H., Coşkun, M., & Şahin, P. (2005). Antioxidant Activity Studies on Selected Sideritis. Species Native to Turkey. Pharmaceutical Biology, 43(2), 173-177.
• • Jaiswal, R., Kiprotich, J., & Kuhnert, N. (2011). Determination of the hydroxycinnamate profile of 12 members of the Asteraceae family. Phytochemistry, 72(8), 781-790.
• • Karahüseyin, S., & Sarı, A. (2019). Plants used in traditional treatment against diarrhea in Turkey. İstanbul Journal of Pharmacy, 49(1), 33-44.
• • Karioti, A., Bolognesi, L., Vincieri, F. F., & Bilia, A. R. (2010). Analysis of the constituents of aqueous preparations of Stachys recta by HPLC–DAD and HPLC–ESI-MS. Journal of Pharmaceutical and Biomedical Analysis, 53(1), 15-23.
• • Kim, J. K., & Park, S. U. (2019). Chlorogenic acid and its role in biological functions: an up to date. EXCLI journal, 18, 310-316.
• • Kirimer, N., Baser, K. H. C., Demirci, B., & Duman, H. (2004). Essential oils of Sideritis species of Turkey belonging to the section Empedoclia. Chemistry of Natural Compounds, 40(1), 19-23.
• • Kirimer, N., Tabanca, N., Özek, T., Tümen, G., & Baser, K. H. C. (2000). Essential oils of annual Sideritis species growing in Turkey. Pharmaceutical Biology, 38(2), 106-111.
• • Kırmızıbekmez, H., Montoro, P., Piacente, S., Pizza, C., Dönmez, A., & Çalış, İ. (2005). Identification by HPLC‐PAD‐MS and quantification by HPLC‐PAD of phenylethanoid glycosides of five Phlomis species. Phytochemical Analysis: An International Journal of Plant Chemical and Biochemical Techniques, 16(1), 1-6.
• • Kubica, P., Szopa, A., Kokotkiewicz, A., Miceli, N., Taviano, M. F., Maugeri, A., ... & Ekiert, H. (2020). Production of Verbascoside, Isoverbascoside and phenolic acids in callus, suspension, and bioreactor cultures of Verbena officinalis and biological properties of biomass extracts. Molecules, 25(23), 5609.
• • Mitreski, I., Stanoeva, J. P., Stefova, M., Stefkov, G., & Kulevanova, S. (2014). Polyphenols in representative Teucrium Species in the flora of r. Macedonia: LC/DAD/ESI-MS n profile and content. Natural Product Communications, 9(2), 175-180.
• • Pereira, O. R., Domingues, M. R., Silva, A. M., & Cardoso, S. M. (2012). Phenolic constituents of Lamium album: Focus on isoscutellarein derivatives. Food Research International, 48(1), 330-335.
• • Petreska, J., Stefkov, G., Kulevanova, S., Alipieva, K., Bankova, V., & Stefova, M. (2011). Phenolic compounds of mountain tea from the Balkans: LC/DAD/ESI/MSn profile and content. Natural Product Communications, 6(1), 21-30.
• • Petreska, J., Stefova, M., Ferreres, F., Moreno, D. A., Tomás-Barberán, F. A., Stefkov, … Gil-Izquierdo, A. (2011). Potential bioactive phenolics of Macedonian Sideritis species used for medicinal “Mountain Tea”. Food Chemistry, 125(1), 13-20.
• • Russo, E. B., & Marcu, J. (2017). Cannabis pharmacology: the usual suspects and a few promising leads. Advances in Pharmacology, 80, 67-134.
• • Sarac, N., & Ugur, A. (2007). Antimicrobial activities and usage in folkloric medicine of some Lamiaceae species growing in Mugla, Turkey. EurAsian Journal of BioSciences, 4, 28-37.
• • Smiljkovic, M., Stanisavljevic, D., Stojkovic, D., Petrovic, I., Vicentic, J. M., Popovic, J., ... & Sokovic, M. (2017). Apigenin-7-O-glucoside versus apigenin: Insight into the modes of anticandidal and cytotoxic actions. EXCLI Journal, 16, 795–807.
• • Stanoeva, J. P., Bagashovska, D., & Stefova, M. (2012). Characterization of urinary bioactive phenolic metabolites excreted after consumption of a cup of mountain tea (Sideritis scardica) using liquid chromatography–tandem mass spectrometry. Macedonian Journal of Chemistry and Chemical Engineering, 31(2), 229-243.
• • Stanoeva, J. P., Stefova, M., Stefkov, G., Kulevanova, S., Alipieva, K., Bankova, V., Avena, I., & Evstatieva, L. N. (2015). Chemotaxonomic contribution to the Sideritis species dilemma on the Balkans. Biochemical Systematics and Ecology, 61, 477-487.
• • Tabanca, N., Gao, Z., Demirci, B., Techen, N., Wedge, D. E., Ali, A., … Baser, K. H. C. (2014). Molecular and phytochemical investigation of Angelica dahurica and Angelica pubescentis essential oils and their biological activity against Aedes aegypti, Stephanitis pyrioides, and Colletotrichum species. Journal of Agricultural and Food Chemistry, 62(35), 8848-8857.
• • Topcu, G., Barla, A., Gören, A. C., Bilsel, G., Bilsel, M., & Tümen, G. (2005). Analysis of the essential oil composition of Sideritis albiflora using direct thermal desorption and headspace GC-MS techniques. Turkish Journal of Chemistry, 29(5), 525-529.
• • Türkmenoğlu, F. P., & Duman, H. (2015). Comparative Morphological Investigations on Three Related Sideritis L. Species Belonging Section Empedoclia Rafi n Bentham. Hacettepe University Journal of the Faculty of Pharmacy, (1), 87-101.
• • Ulubelen, A., Topcu, G., & Kolak, U. (2005). Labiatae flavonoids and their bioactivity. Studies in Natural Products Chemistry, 30, 233-302.
• • Usluer, Ö., Duru, M. E., & Öztürk, M. (2005).Chemical compositions of the plant Sideritis albiflora Hub.-Purple and antioxidant activities of some extracts.. XIX. National Chemistry Congress, Kuşadası, OKP156, 915.
• • Xing, S., Peng, Y., Wang, M., Chen, D., & Li, X. (2014). In vitro human fecal microbial metabolism of Forsythoside A and biological activities of its metabolites. Fitoterapia, 99, 159-165.
• • Yeşilada, E., & Ezer, N. (1989). The antiinflammatory activity of some Sideritis species growing in Turkey. International Journal of Crude Drug Research, 27(1), 38-40.
• • Żyżelewicz, D., Kulbat-Warycha, K., Oracz, J., & Żyżelewicz, K. (2020). Polyphenols and other bioactive compounds of Sideritis plants and their potential biological activity. Molecules, 25(16), 3763