Achillea biebersteinii ve A. millefolium Bitkilerinin Fitokimyasal İçeriği ve In Silico Moleküler Doking Çalışmaları

Yıl 2024, Cilt: 5 Sayı: 2, 10 - 24, 31.08.2024

Fatih Gül , Yunus Başar , İbrahim Demirtas

https://doi.org/10.53445/batd.1513403

Öz

Achillea L. cinsi, damarlı bitkilerin en büyük familyası olan Asteraceae familyasına aittir. Achillea türleri, dünya çapında yaygın olarak bulunan, içerdiği biyoaktif bileşikler nedeniyle geleneksel tıpta yaygın olarak kullanılan tıbbi bir bitkidir. Bu çalışmada Iğdır Üniversitesi kampüsü arazisinde yetişen iki Achillea türünün fitokimyasal içeriğini analiz ederek bitkilerin biyolojik aktivite potansiyelini incelemeyi amaçladık. Bu çalışmada, farklı dönemlerde hasat edilen A. biebersteinii ve A. millefolium'un çiçek, gövde-yaprak kısımlarının uçucu ve fenolik içerikleri kromatografik yöntemlerle (GC-MS/MS ve LC-MS/MS) belirlendi. GC-MS analizi sonucunda A. millefolium bitkisinde yüksek düzeyde eucalyptol (%43.22) varlığının olduğu ve hasat zamanının A. biebersteinii bitkisinde uçucu bileşenlerin oranlarını önemli ölçüde değiştiği görüldü. LC-MS/MS analizinde, tüm bitki materyallerindeki ana bileşenin klorojenik asit olduğunu gösterdi. Ayrıca ana bileşen, klorojenik asit ile ksantin oksidaz enzimi etkileşimleri, in silico moleküler yerleştirme yöntemi ile belirlendi. Ksantin oksidaz ile klorojenik asit etkileşiminin, bağlanma enerjisi (-8,0 kcal/mol) ve MolDock skoru (-130,96) hesaplandı.

Anahtar Kelimeler

A. biebersteinii, A. millefolium, Fitokimyasal analiz, Klorojenik asit, Ksantin oksidaz

Proje Numarası

YİP0723İ01

Phytochemical Content and In Silico Molecular Docking Studies of Achillea biebersteinii and A. millefolium Plants

Öz

The genus Achillea L. belongs to Asteraceae, the largest family of vascular plants. Achillea species is a medicinal plant widely used in traditional medicine due to the bioactive compounds it contains that are widely distributed worldwide. In this study, we aimed to examine the biological activity potential of the plants by analyzing the phytochemical content of two Achillea species growing on the land of Iğdır University campus. In this study, the volatile and phenolic contents of flower, and stem-leaf parts of A. biebersteinii and A. millefolium harvested in different periods were determined by chromatographic methods (GC-MS/MS and LC-MS/MS). As a result of the GC-MS analysis, it was observed that the presence of high levels of eucalyptol (43.22%) in the A. millefolium plant and that the harvest time dramatically changed the rates of volatile components in the A. biebersteinii plants. The LC-MS/MS analysis showed that the main constituent in all plant materials was chlorogenic acid. In addition, the main component, chlorogenic acid interactions with the xanthine oxidase enzyme were determined by in silico molecular docking. Chlorogenic acid interaction with xanthine oxidase was calculated of binding energies (-8.0 kcal/mol) and MolDock score (-130.96).

Anahtar Kelimeler

A. biebersteinii, A. millefolium, Phytochemical analysis, Chlorogenic acid, Xanthine oxidase

Destekleyen Kurum

Yüksek Öğretim Kurumu (YÖK)

Proje Numarası

YİP0723İ01

Teşekkür

The High-Value Added Agricultural Products Specialization Program, Production of Value-Added Raw Materials from Agricultural Products by Supercritical Carbon Dioxide Extraction Method (Project No: YİP0723İ01).

Kaynakça

• Abd-ElGawad, A., Essa, A., Taher, R., Souid, A., El-Newary, S., Sarker, T. C., El Gendy, A. E. N., Assaeed, A., Dar, B., & Elshamy, A. (2024). Chemical components and antioxidant potential of essential oil of Rhanterium epapposum growing in sandy habitat in Saudi Arabia: In silico study on cytochrome P450 1A1 and xanthine oxidase. Journal of Essential Oil Bearing Plants, 27. https://doi.org/10.1080/0972060X.2024.2358894
• Arabaci, T. (2012). Achillea hamzaoglui (Asteraceae), a New Species from Turkey. Annales Botanici Fennici, 46, 459-463. https://doi.org/10.5735/085.046.0516
• Bariş, Ö., Güllüce, M., Sahin, F., Ozer, H., Kilic, H., Özkan, H., Sökmen, M., & Özbek, T. (2006). Biological activities of the essential oil and methanol extract of Achillea biebersteinii Afan. (Asteraceae). Turkish Journal of Biology, 30, 65-73.
• 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. https://doi.org/10.1080/07391102.2023.2250461
• Başar, Y., Yenigün, S., Gül, F., Özen, T., Demirtas, I., Mehmet, A., & Temel, S. (2024). Phytochemical profiling, molecular docking and ADMET prediction of crude extract of Atriplex nitens Schkuhr for the screening of antioxidant and urease inhibitory. International Journal of Chemistry and Technology, 8. https://doi.org/10.32571/ijct.1389719
• Bremer, K. r. (1993). Generic monograph of the Asteraceae-Anthemideae. Bulletin of the Natural History Museum. Botany series, 23(2), 71-177. https://www.biodiversitylibrary.org/part/224587
• Candan, F., Unlu, M., Tepe, B., Daferera, D., Polissiou, M., Sökmen, A., & Akpulat, H. A. (2003). Antioxidant and antimicrobial activity of the essential oil and methanol extracts of Achillea millefolium subsp. millefolium Afan. (Asteraceae). J Ethnopharmacol, 87(2-3), 215-220. https://doi.org/10.1016/s0378-8741(03)00149-1
• Candan, F., Unlu, M., Tepe, B., Daferera, D., Polissiou, M., Sökmen, A., & Akpulat, H. A. (2003). Antioxidant and antimicrobial activity of the essential oil and methanol extracts of Achillea millefolium subsp. millefolium Afan. (Asteraceae). Journal of Ethnopharmacology, 87(2), 215-220. https://doi.org/https://doi.org/10.1016/S0378-8741(03)00149-1
• Demirci, M. A., Ipek, Y., Gul, F., Ozen, T., & Demirtas, I. (2018). Extraction, isolation of heat-resistance phenolic compounds, antioxidant properties, characterization and purification of 5-hydroxymaltol from Turkish apple pulps. Food Chem, 269, 111-117. https://doi.org/10.1016/j.foodchem.2018.06.147
• Granger, D. N., Höllwarth, M. E., & Parks, D. A. (1986). Ischemia-reperfusion injury: role of oxygen-derived free radicals. Acta Physiol Scand Suppl, 548, 47-63.
• Güneş, F., & Ozhatay, N. (2000). Flora of Turkey and the East Aegean Islands. In (Vol. 11, pp. 92-94).
• İpek, Y., Başar, Y., Yenigün, S., Behçet, L., Özen, T., & Demirtas, I. (2024). In vitro bioactivities and in silico enzyme interactions of abietatrien-3β-ol by bio-guided isolation from Nepeta italica subsp. italica. Journal of Biomolecular Structure and Dynamics. https://doi.org/10.1080/07391102.2024.2322626
• Karamenderes, C., Karabay, N. U., & Zeybek, U. (2002). Composition and antimicrobial activity of the essential oils of some Achillea L. Species in Turkey. Acta Pharmaceutica Turcica, 44, 221-225.
• Kostevski, I. R., Petrović, G. M., Stojanović, G. S., Stamenković, J. G., & Zlatković, B. K. (2016). Essential Oil Chemical Composition and Headspace Volatiles Profile of Achillea coarctata from Serbia. Natural Product Communications, 11(4), 1934578X1601100431. https://doi.org/10.1177/1934578x1601100431
• Martin, H. M., Hancock, J. T., Salisbury, V., & Harrison, R. (2004). Role of xanthine oxidoreductase as an antimicrobial agent. Infect Immun, 72(9), 4933-4939. https://doi.org/10.1128/iai.72.9.4933-4939.2004
• Page, S., Powell, D., Benboubetra, M., Stevens, C. R., Blake, D. R., Selase, F., Wolstenholme, A. J., & Harrison, R. (1998). Xanthine oxidoreductase in human mammary epithelial cells: activation in response to inflammatory cytokines. Biochim Biophys Acta, 1381(2), 191-202. https://doi.org/10.1016/s0304-4165(98)00028-2
• Popovic, M., Jakovljevic, V., Bursac, M., Mitic, R., Raskovic, A., & Kaurinovic, B. (2002). Biochemical investigation of yarrow extracts (Achillea millefolium L.). Oxidation Communications, 25, 469-475.
• Saeidnia, S., Gohari, A., Mokhber-Dezfuli, N., & Kiuchi, F. (2011). A review on phytochemistry and medicinal properties of the genus Achillea. Daru, 19(3), 173-186.
• Wallander, E., & Albert, V. (2001). Phylogeny and classification of Oleaceae based on RPS16 and TRNL-F sequence data. American journal of botany, 87, 1827-1841. https://doi.org/10.2307/2656836
• Wang, L., Pan, X., Jiang, L., Chu, Y., Gao, S., Jiang, X., Zhang, Y., Chen, Y., Luo, S., & Peng, C. (2022). The Biological Activity Mechanism of Chlorogenic Acid and Its Applications in Food Industry: A Review. Front Nutr, 9, 943911. https://doi.org/10.3389/fnut.2022.943911
• Yenigün, S., Başar, Y., Gül, F., Marah, S., Behcet, L., Demirtas, I., & Özen, T. (2024a). 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. https://doi.org/10.1002/slct.202400583
• Yenigun, S., Basar, Y., Ipek, Y., Gok, M., Behcet, L., Ozen, T., & Demirtas, I. (2024b). A potential DNA protector, enzyme inhibitor and in silico studies of daucosterol isolated from six Nepeta species. Process Biochemistry, 143, 234-247. https://doi.org/https://doi.org/10.1016/j.procbio.2024.04.039
• Zeynalov, Y., & Türkoğlu, M. (2016). The Flora of Agri mountain. Turkish Ministry of Forestry and Water Affairs.