Phytochemical analyses of Ebenus haussknechtii flowers: Quantification of phenolics, antioxidants effect, and molecular docking studies

Yıl 2024, Cilt: 5 Sayı: 2, 1 - 9, 31.08.2024

Ramazan Erenler , İlyas Yıldız , Esma Nur Geçer , Aslı Yıldırım Kocaman , Mehmet Hakkı Alma , İbrahim Demirtas , Yunus Başar , İbrahim Hosaflıoğlu , Lütfi Behçet

https://doi.org/10.53445/batd.1479874

Öz

Plants have been benefited as medicine and food since ancient times. After the discovery of spectroscopy, bioactive compounds in plants have been elucidated and have been utilized in drug development. Ebenus haussknechtii has been utilized for traditional medicine. In this study, Ebenus haussknechtii flowers were extracted in methanol and quantification of phenolics of this extract was conducted by LC-MS/MS. Antioxidant effect of E. haussknechtii flowers was carried out using DPPH free radical scavenging assay, ABTS radical cation scavenging assay, and hydroxyl radical scavenging assay. Quantitative analysis revealed that shikimic acid (0.77 mg/g extract), protocatechuic acid (0.61), catechin (0.34), hydroxybenzaldeyde (0.32) were determined as major products. Hence, the interaction of shikimic acid and DNA gyrase enzyme was calculated theoretically. Moreover, MolDock score, and binding affinity were determined as -73.64 and -5.5 kcal/mol respectively. Ebenus haussknechtii flowers displayed good antioxidant activity. In DPPH assay, the extract displayed good activity with the value of 7.27 ± 0.173 (IC50, µg/mL). Moreover, the flower extract exhibited the outstanding ABTS activity with a value of 6.62 ± 0.23 (IC50, µg/mL) in comparison to the extract BHA (7.58 ± 0.15, IC50, µg/mL).

Anahtar Kelimeler

Ebenus haussknechtii, LC-MS/MS, Molecular docking, Antioxidant activity

Ebenus haussknechtii çiçeklerinin fitokimyasal analizleri: Fenoliklerin miktarının belirlenmesi, antioksidan etkisi ve moleküler yerleştirme çalışmaları

Öz

Bitkilerden eski çağlardan beri ilaç ve gıda olarak yararlanılmaktadır. Spektroskopinin keşfinden sonra bitkilerde bulunan biyoaktif bileşikler aydınlatılmış ve ilaç geliştirmede kullanılmaya başlanmıştır. Ebenus haussknechtii geleneksel tıpta kullanılmaktadır. Bu çalışmada, Ebenus haussknechtii çiçekleri metanol içerisinde ekstrakte edilmiş ve bu ekstraktın fenoliklerinin miktar tayini LC-MS/MS ile yapılmıştır. E. haussknechtii çiçeklerinin antioksidan etkisi, DPPH serbest radikal giderme testi, ABTS radikal katyon giderme testi ve hidroksil radikal giderme testi kullanılarak gerçekleştirildi. Kantitatif analizde şikimik asit (0,77 mg/g ekstrakt), protokatekuik asit (0,61), kateşin (0,34), hidroksibenzaldeidin (0,32) ana ürünler olduğu belirlendi. Böylece şikimik asit ile DNA giraz enziminin etkileşimi teorik olarak hesaplandı. Ayrıca MolDock skoru ve bağlanma afinitesi sırasıyla -73,64 ve -5,5 kcal/mol olarak belirlendi. E. haussknechtii çiçekleri iyi antioksidan aktivite sergiledi. DPPH testinde ekstrakt 7.27 ± 0.173 (IC50, µg/mL) değeriyle iyi aktivite sergiledi. Ayrıca çiçek ekstraktı, BHA (7.58 ± 0.15, IC50, µg/mL) ile karşılaştırıldığında 6.62 ± 0.23 (IC50, µg/mL) değeriyle olağanüstü ABTS aktivitesi sergiledi.

Anahtar Kelimeler

Ebenus haussknechtii, LC-MS/MS, Moleküler doking, Antioksidan aktivite

Kaynakça

• References
• Aksit, H., Çelik, S. M., Sen, Ö., Erenler, R., Demirtas, I., Telci, I., & Elmastas, M. (2014). Complete isolation and characterization of polar portion of Mentha dumetorum water extract. Records of Natural Products, 8(3), 277-280.
• Atalar, M. N., Erenler, R., Turkan, F., Alma, M. H., Demirtas, I., Baran, A., Kandemir, S. I., Kekec, A. I., & Saltan, F. Z. (2023). Phytochemical analysis and biological activity of Corchorus olitorius L.: Quantitative analysis of bioactive compounds by LC–MS/MS, antibacterial, enzyme inhibition, and cytotoxic activities. European Journal of Integrative Medicine, 62, 102290. https://doi.org/10.1016/j.eujim.2023.102290.
• Aydin, A., Erenler, R., Yılmaz, B., & Tekin, Ş. (2016). Antiproliferative effect of Cherry laurel. Journal of the Turkish Chemical Society, Section A: Chemistry, 3(3), 217-228. https://doi.org/10.18596/jotcsa.21204.
• Başar, Y., Demirtaş, İ., Yenigün, S., İpek, Y., Özen, T., & Behçet, L. (2024). Molecular docking, molecular dynamics, MM/PBSA approaches and bioactivity studies of nepetanudoside B isolated from endemic Nepeta aristata. J Biomol Struct Dyn, 1-14. 10.1080/07391102.2024.2309641.
• Cakmak, O., Erenler, R., Tutar, A., & Celik, N. (2006). Synthesis of new anthracene derivatives. Journal of Organic Chemistry, 71(5), 1795-1801. https://doi.org/10.1021/jo051846u.
• Cragg, G. M., Newman, D. J., & Snader, K. M. (1997). Natural products in drug discovery and development. Journal of Natural Products, 60(1), 52-60. https://doi.org/10.1021/np9604893.
• Dag, B., Tenekecioğlu, Y., Aral, T., Kızılkaya, H., Erenler, R., & Genc, N. (2023). Synthesis, Characterization, and Antioxidant Activity of a Novel Schiff Base, an Amine and Amine–Metal Complexes. Russian Journal of Bioorganic Chemistry, 49(4), 861-866. https://doi.org/10.1134/S1068162023040106.
• Demirtas, I., Erenler, R., Elmastas, M., & Goktasoglu, A. (2013). Studies on the antioxidant potential of flavones of Allium vineale isolated from its water-soluble fraction. Food Chemistry, 136(1), 34-40. https://doi.org/10.1016/j.foodchem.2012.07.086.
• Elmastas, M., Erenler, R., Isnac, B., Aksit, H., Sen, O., Genc, N., & Demirtas, I. (2016). Isolation and identification of a new neo-clerodane diterpenoid from Teucrium chamaedrys L. Natural Product Research, 30(3), 299-304. https://doi.org/10.1080/14786419.2015.1057583.
• Elmastas, M., Ozturk, L., Gokce, I., Erenler, R., & Aboul‐Enein, H. Y. (2004). Determination of antioxidant activity of marshmallow flower (Althaea officinalis L.). Analytical Letters, 37(9), 1859-1869. https://doi.org/10.1081/AL-120039431.
• Elmastaş, M., Telci, İ., Akşit, H., & Erenler, R. (2015). Comparison of total phenolic contents and antioxidant capacities in mint genotypes used as spices/Baharat olarak kullanılan nane genotiplerinin toplam fenolik içerikleri ve antioksidan kapasitelerinin karşılaştırılması. Turkish Journal of Biochemistry, 40(6), 456-462. https://doi.org/10.1515/tjb-2015-0034.
• Erenler, R., Atalar, M. N., Yıldız, İ., Geçer, E. N., Yıldırım, A., Demirtas, İ., & Alma, M. H. (2023). Quantitative analysis of bioactive compounds by LC-MS/MS from Inula graveolens. Bütünleyici ve Anadolu Tıbbı Dergisi, 4(3), 3-10. https://doi.org/10.53445/batd.1278048.
• Erenler, R., & Biellmann, J. F. (2005). Facile conversion of pyridine propargylic alcohols to enones: Stereochemistry of protonation of allenol. Tetrahedron Letters, 46(34), 5683-5685. https://doi.org/10.1016/j.tetlet.2005.06.087.
• Erenler, R., & Biellmann, J. F. (2007). Synthesis of pentafluorophenyl- and pyridinyl-3 allenes. Journal of the Chinese Chemical Society, 54(1), 103-108. https://doi.org/10.1002/jccs.200700017.
• Erenler, R., & Cakmak, O. (2004). Synthesis of hexabromo, hydroxy, epoxy, methoxy and nitroxy derivatives of tetralins and naphthalenes. Journal of Chemical Research(8), 566-569. https://doi.org/10.3184/0308234042563947.
• Erenler, R., Chaoui, R., Yildiz, I., Genc, N., Gecer, E. N., Temiz, C., & Akkal, S. (2023). Biosynthesis, Characterisation, and Antioxidant Activity of Silver Nanoparticles using Schinus molle L. Trends in Sciences, 20(10), 6105-6105. https://doi.org/10.48048/tis.2023.6105.
• Erenler, R., Gecer, E. N., Hosaflioglu, I., & Behcet, L. (2023). Green synthesis of silver nanoparticles using Stachys spectabilis: Identification, catalytic degradation, and antioxidant activity. Biochemical and Biophysical Research Communications, 659, 91-95. https://doi.org/10.1016/j.bbrc.2023.04.015.
• Erenler, R., & Hosaflioglu, I. (2023). Green synthesis of silver nanoparticles using Onobrychis sativa L.: Characterization, catalytic degradation of methylene blue, antioxidant activity, and quantitative analysis of bioactive compounds. Materials Today Communications, 35, 105863. https://doi.org/10.1016/j.mtcomm.2023.105863.
• Erenler, R., Karan, T., & Bozer, B. M. (2023). Synthesis of silver nanoparticles from Camellia sinensis waste and evaluation of their cytotoxic effect. Environmental Engineering and Management Journal, 22(11), 1783-1790. http://doi.org/10.30638/eemj.2023.154
• Erenler, R., Karan, T., & Hosaflioglu, İ. (2023). Phytochemical analysis of Syringa vulgaris: Quantitative analysis of natural compounds by LC-ESI-MS/MS. Turkish Journal of Biodiversity, 6(2), 75-78. https://doi.org/10.38059/biodiversity.1312872.
• Erenler, R., Telci, I., Ulutas, M., Demirtas, I., Gul, F., Elmastas, M., & Kayir, O. (2015). Chemical Constituents, Quantitative Analysis and Antioxidant Activities of Echinacea purpurea (L.) Moench and Echinacea pallida (Nutt.) Nutt. Journal of Food Biochemistry, 39(5), 622-630. https://doi.org/10.1111/jfbc.12168.
• Erenler, R., Yaman, C., Demirtas, I., & Alma, M. H. (2023). Phytochemical Investigation of Hypericum heterophyllum Flowers: LC-ESI-MS/MS Analysis, Total Phenolic and Flavonoid Contents, Antioxidant Activity. The Natural Products Journal, 13(7), e120123212672. https://doi.org/10.2174/2210315513666230112165545.
• Erenler, R., Yilmaz, S., Aksit, H., Sen, O., Genc, N., Elmastas, M., & Demirtas, I. (2014). Antioxidant activities of chemical constituents isolated from Echinops orientalis Trauv. Records of Natural Products, 8(1), 32-36.
• Gecer, E. N., & Erenler, R. (2022). Biosynthesis of silver nanoparticles using Dittrichia graveolens (Asteraceae) leaves extract: characterisation and assessment of their antioxidant activity. Turkish Journal of Biodiversity, 5(1), 50-56. https://doi.org/10.38059/biodiversity.1090549.
• Gecer, E. N., & Erenler, R. (2023). Biogenic synthesis of silver nanoparticles using Echium vulgare: Characterisation, quantitative analysis of bioactive compounds, antioxidant activity and catalytic degradation. Journal of the Indian Chemical Society, 100(5), 101003. https://doi.org/10.1016/j.jics.2023.101003.
• Gecer, E. N., Erenler, R., Temiz, C., Genc, N., & Yildiz, I. (2022). Green synthesis of silver nanoparticles from Echinacea purpurea (L.) Moench with antioxidant profile. Particulate Science and Technology, 40(1), 50-57. https://doi.org/10.1080/02726351.2021.1904309.
• Ghosh, S., Chisti, Y., & Banerjee, U. C. (2012). Production of shikimic acid. Biotechnology advances, 30(6), 1425-1431. https://doi.org/10.1016/j.biotechadv.2012.03.001.
• Guemidi, C., Ait Saada, D., Ait Chabane, O., Elmastas, M., Erenler, R., Yilmaz, M. A., Tarhan, A., Akkal, S., & Khelifi, H. (2024). Enhancement of yogurt functionality by adding Mentha piprita phenolic extract and evaluation of its quality during cold storage. Food Science & Nutrition. https://doi.org/10.1002/fsn3.3981.
• Hayta, S., Tasar, N., Cakilcioglu, U., & Gedik, O. (2014). Morphological, karyological features and pollen morphology of endemic Ebenus haussknechtii Bornm. ex Hub.-Mor. from Turkey: A traditional medicinal herb. Journal of herbal medicine, 4(3), 141-146. https://doi.org/10.1016/j.hermed.2014.04.006.
• Houari, F. Z., Erenler, R., & Hariri, A. (2022). Biological activities and chemical composition of Rubia tinctorum (L.) root and aerial part extracts thereof. Acta Biológica Colombiana, 27(3). https://doi.org/10.15446/abc.v27n3.95476.
• Kakkar, S., & Bais, S. (2014). A review on protocatechuic acid and its pharmacological potential. International Scholarly Research Notices, 2014, Article ID 952943 https://doi.org/10.1155/2014/952943.
• Karan, T., Erenler, R., & Bozer Moran, B. (2022). Synthesis and characterization of silver nanoparticles using curcumin: cytotoxic, apoptotic, and necrotic effects on various cell lines. Zeitschrift für Naturforschung C, 77(7-8), 343-350. https://doi.org/10.1515/znc-2021-0298.
• Karan, T., Erenler, R., Gonulalan, Z., & Kolemen, U. (2024). Biogenic synthesis of silver nanoparticles using Sambucus nigra leaves: elucidation, antimicrobial, antioxidant activities and quantification of phenolics. Chemical Papers, 78(1), 473-481. https://doi.org/10.1007/s11696-023-03103-9.
• Karan, Y. B., & Erenler, R. (2024). Synthesis of Silver Nanoparticles Using Potato Cultivars with Their Antioxidant Activity. Communications in Soil Science and Plant Analysis, 1-9. https://doi.org/10.1080/00103624.2024.2303105.
• Khodja, E. A. T., Abd El Hamid Khabtane, R. A., Benouchenne, D., Bensaad, M. S., Bensouici, C., & Erenler, R. (2023). In vitro assessment of antioxidant, neuroprotective, anti-urease and anti-tyrosinase capacities of Tamarix africana leaves extracts. Journal of Traditional Chinese Medicine, 43(2), 252. https://doi.org/10.19852/j.cnki.jtcm.20230105.003.
• Lu, J., Maezawa, I., Weerasekara, S., Erenler, R., Nguyen, T. D. T., Nguyen, J., Swisher, L. Z., Li, J., Jin, L. W., Ranjan, A., Srivastava, S. K., & Hua, D. H. (2014). Syntheses, neural protective activities, and inhibition of glycogen synthase kinase-3β of substituted quinolines. Bioorganic and Medicinal Chemistry Letters, 24(15), 3392-3397. https://doi.org/10.1016/j.bmcl.2014.05.085.
• Ökten, S., Çakmak, O., Erenler, R., Yüce, Ö., & Tekin, S. (2013). Simple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activities. Turkish Journal of Chemistry, 37(6), 896-908. https://doi.org/10.3906/kim-1301-30.
• Sahin Yaglioglu, A., Akdulum, B., Erenler, R., Demirtas, I., Telci, I., & Tekin, S. (2013). Antiproliferative activity of pentadeca-(8E, 13Z) dien-11-yn-2-one and (E)-1,8-pentadecadiene from Echinacea pallida (Nutt.) Nutt. roots. Medicinal Chemistry Research, 22(6), 2946-2953. https://doi.org/10.1007/s00044-012-0297-2.
• Sahin Yaglioglu, A., Erenler, R., Gecer, E. N., & Genc, N. (2022). Biosynthesis of Silver Nanoparticles Using Astragalus flavesces Leaf: Identification, Antioxidant Activity, and Catalytic Degradation of Methylene Blue. Journal of Inorganic and Organometallic Polymers and Materials, 32(3700-3707), 1-8.
• Topçu, G., Erenler, R., Çakmak, O., Johansson, C. B., Çelik, C., Chai, H.-B., & Pezzuto, J. M. (1999). Diterpenes from the berries of Juniperus excelsa. Phytochemistry, 50(7), 1195-1199. https://doi.org/10.1016/S0031-9422(98)00675-X.
• Yaman, C., Erenler, R., Atalar, M. N., Adem, Ş., & Çalişkan, U. K. (2024). Phytochemical Properties, Antioxidant and in Vitro/in Silico Anti-Acetylcholinesterase Activities of Hypericum heterophyllum Leaf from Türkiye. Brazilian Archives of Biology and Technology, 67, e24230043. https://doi.org/10.1590/1678-4324-2024230043.
• Yaman, C., Önlü, Ş., Ahmed, H., & Erenler, R. (2022). Comparison of phytochemicals and antioxidant capacity of Hypericum perforatum; wild plant parts and in vitro samples. Journal of Animal & Plant Sciences, 32(2), 596-603. https://doi.org/10.36899/JAPS.2022.2.0459.