Journals / International Journal of Secondary Metabolite / 2026 / Volume: 13 Issue: 1

Phytochemical profile, antioxidant capacity, and enzyme inhibitory properties of Alkanna tubulosa extract obtained via ultrasound-assisted extraction

Zeyneb Karakuş(AFYON KOCATEPE ÜNİVERSİTESİ)0000-0002-7245-7363
Pages
—
Publication Date
2026-03-09
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Future work should isolate dominant constituents, evaluate their synergistic interactions and validate efficacy in relevant cellular and in vivo models.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Phytochemicals from under-explored Mediterranean taxa represent an untapped reservoir of multitarget agents for oxidative and metabolic stress management.
📊
Key Findings & Data:Total phenolics reached 97.34 mg GAEs (gallic acid equivalents)/g and flavonoids 45.03 mg REs (Rutin equivalents)/g.
💡
Conclusion & Impact:Future work should isolate dominant constituents, evaluate their synergistic interactions and validate efficacy in relevant cellular and in vivo models.
🔬Design:Modeling & Simulation
📍Scope:Comprehensive Sample
⚙️Variables:Alkanna tubulosa · Ultrasound-assisted extraction · Phenolic compounds

Abstract

Phytochemicals from under-explored Mediterranean taxa represent an untapped reservoir of multitarget agents for oxidative and metabolic stress management. Here, we characterised the antioxidant and enzyme-modulating potential of a methanolic ultrasound-assisted extract (UAE) prepared from the aerial parts of Alkanna tubulosa. Total phenolics reached 97.34 mg GAEs (gallic acid equivalents)/g and flavonoids 45.03 mg REs (Rutin equivalents)/g. LC-ESI-MS/MS (Liquid Chromatography-Electrospray Ionization-Tandem Mass Spectrometry) identified 17 metabolites, predominantly hesperidin (13626 µg/g) and rosmarinic acid (6637 µg/g). The extract exhibited potent radical-scavenging capacity-DPPH (2,2-Diphenyl-1-picrylhydrazyl): 181.43 mg TEs (Trolox equivalents)/g; ABTS [2,2'-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)]: 182.85 mg TEs/g-and high electron-donor power—phosphomolybdenum: 570.77 mg TEs/g; CUPRAC (Cupric Ion Reducing Antioxidant Capacity): 479.07 mg TE/g; FRAP (Ferric Reducing Antioxidant Power): 270.59 mg TE/g-but only moderate Fe²⁺ chelation (6.63 mg EDTAEs (Ethylenediaminetetraacetic Acid equivalents)/g). Enzymatic assays revealed selective inhibition of carbohydrate-hydrolysing enzymes, with α-glucosidase and α-amylase activities equivalent to 598.36 and 299.50 mg ACEs (Acarbose equivalents)/g, respectively; tyrosinase suppression reached 57.30 mg KAEs (Kojic acid equivalents)/g, whereas cholinesterase inhibition was low [AChE (acetylcholinesterase) 2.07 mg GALAEs (Galanthamine equivalents)/g; BChE (butyrylcholinesterase) 1.05 mg GALAEs/g]. These findings position A. tubulosa as a rich source of phenolic acid and flavanone-glycoside-centred antioxidants with promising anti-hyperglycaemic and ancillary dermatoprotective properties. Future work should isolate dominant constituents, evaluate their synergistic interactions and validate efficacy in relevant cellular and in vivo models.

Özet

Phytochemicals from under-explored Mediterranean taxa represent an untapped reservoir of multitarget agents for oxidative and metabolic stress management. Here, we characterised the antioxidant and enzyme-modulating potential of a methanolic ultrasound-assisted extract (UAE) prepared from the aerial parts of Alkanna tubulosa. Total phenolics reached 97.34 mg GAEs (gallic acid equivalents)/g and flavonoids 45.03 mg REs (Rutin equivalents)/g. LC-ESI-MS/MS (Liquid Chromatography-Electrospray Ionization-Tandem Mass Spectrometry) identified 17 metabolites, predominantly hesperidin (13626 µg/g) and rosmarinic acid (6637 µg/g). The extract exhibited potent radical-scavenging capacity-DPPH (2,2-Diphenyl-1-picrylhydrazyl): 181.43 mg TEs (Trolox equivalents)/g; ABTS [2,2'-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)]: 182.85 mg TEs/g-and high electron-donor power—phosphomolybdenum: 570.77 mg TEs/g; CUPRAC (Cupric Ion Reducing Antioxidant Capacity): 479.07 mg TE/g; FRAP (Ferric Reducing Antioxidant Power): 270.59 mg TE/g-but only moderate Fe²⁺ chelation (6.63 mg EDTAEs (Ethylenediaminetetraacetic Acid equivalents)/g). Enzymatic assays revealed selective inhibition of carbohydrate-hydrolysing enzymes, with α-glucosidase and α-amylase activities equivalent to 598.36 and 299.50 mg ACEs (Acarbose equivalents)/g, respectively; tyrosinase suppression reached 57.30 mg KAEs (Kojic acid equivalents)/g, whereas cholinesterase inhibition was low [AChE (acetylcholinesterase) 2.07 mg GALAEs (Galanthamine equivalents)/g; BChE (butyrylcholinesterase) 1.05 mg GALAEs/g]. These findings position A. tubulosa as a rich source of phenolic acid and flavanone-glycoside-centred antioxidants with promising anti-hyperglycaemic and ancillary dermatoprotective properties. Future work should isolate dominant constituents, evaluate their synergistic interactions and validate efficacy in relevant cellular and in vivo models.

🔖

Cite This Article

Karakuş, Z. (2026). Phytochemical profile, antioxidant capacity, and enzyme inhibitory properties of Alkanna tubulosa extract obtained via ultrasound-assisted extraction. International Journal of Secondary Metabolite, Volume: 13 Issue: 1. https://doi.org/10.21448/ijsm.1721228

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (36)

  1. ALNasser, M.N., Alboraiy, G.M., Alsowig, E.M., & Alqattan, F.M. (2025). Cholinesterase Inhibitors from Plants and Their Potential in Alzheimer’s Treatment: Systematic Review. Brain Sciences, 15(2), 215. https://doi.org/10.3390/brainsci15020215
  2. Apak, R., Güçlü, K., Özyürek, M., Esin Karademir, S., & Erçaǧ, E. (2006). The cupric ion reducing antioxidant capacity and polyphenolic content of some herbal teas. [Article]. International Journal of Food Sciences and Nutrition, 57(5-6), 292-304. https://doi.org/10.1080/09637480600798132
  3. Assimopoulou, A.N., Sturm, S., Stuppner, H., & Papageorgiou, V.P. (2009). Preparative isolation and purification of alkannin/shikonin derivatives from natural products by high‐speed counter‐current chromatography. Biomedical Chromatography, 23(2), 182-198. https://doi.org/10.1002/bmc.1101
  4. Atanasov, A.G., Zotchev, S.B., Dirsch, V.M., & Supuran, C.T. (2021). Natural products in drug discovery: advances and opportunities. Nature reviews Drug discovery, 20(3), 200-216. https://doi.org/10.1038/s41573-020-00114-z
  5. Aydi, A., Claumann, C.A., Wüst Zibetti, A., & Abderrabba, M. (2016). Differential scanning calorimetry data and solubility of rosmarinic acid in different pure solvents and in binary mixtures (methyl acetate+ water) and (ethyl acetate+ water) from 293.2 to 313.2 K. Journal of Chemical & Engineering Data, 61(11), 3718-3723. https://doi.org/10.1021/acs.jced.6b00008
  6. Chopra, B., & Dhingra, A.K. (2021). Natural products: A lead for drug discovery and development. Phytotherapy Research, 35(9), 4660-4702. https://doi.org/10.1002/ptr.7099
  7. Fadel, O., El Kirat, K., & Morandat, S. (2011). The natural antioxidant rosmarinic acid spontaneously penetrates membranes to inhibit lipid peroxidation in situ. Biochimica et Biophysica Acta (BBA)-Biomembranes, 1808(12), 2973-2980. https://doi.org/10.1016/j.bbamem.2011.08.011
  8. Farazi, M., Houghton, M.J., Murray, M., & Williamson, G. (2023). A systematic review of the inhibitory effect of extracts from edible parts of nuts on α-glucosidase activity. Food & Function, 14(13), 5962-5976. https://doi.org/10.1039/D3FO00328K
  9. Fujimoto, A., Shingai, Y., Nakamura, M., Maekawa, T., Sone, Y., & Masuda, T. (2010). A novel ring-expanded product with enhanced tyrosinase inhibitory activity from classical Fe-catalyzed oxidation of rosmarinic acid, a potent antioxidative Lamiaceae polyphenol. Bioorganic & Medicinal Chemistry Letters, 20(24), 7393-7396. https://doi.org/10.1016/j.bmcl.2010.10.040
  10. Ganos, C., Zengin, G., Chinou, I., Aligiannis, N., & Graikou, K. (2024). Phytochemical Profiling and Biological Assessment of the Aerial Parts from Three Mediterranean Alkanna Species (A. orientalis, A. tinctoria, A. kotschyana) in the Boraginaceae Family. Plants, 13(2), 278. https://doi.org/10.3390/plants13020278
  11. Gulcin, İ., & Alwasel, S.H. (2023). DPPH radical scavenging assay. Processes, 11(8), 2248. https://doi.org/10.3390/pr11082248
  12. Hartavi, A. (2025). Onosma obtusifolia extracts: Antioxidant potential and molecular docking insights into acetylcholinesterase, α-amylase, and tyrosinase inhibition. Industrial Crops and Products, 233, 121387. https://doi.org/10.1016/j.indcrop.2025.121387
  13. Hartavi, A., Sarikurkcu, C., Kirkan, B., Binzet, R., & Tepe, B. (2025). Chemical Composition, Antioxidant, and Enzyme Inhibitory Activities of Onosma bulbotrichum Extracts. ChemistrySelect, 10(6), e202404776. https://doi.org/10.1002/slct.202404776
  14. Hirata, A., Murakami, Y., Shoji, M., Kadoma, Y., & Fujisawa, S. (2005). Kinetics of radical-scavenging activity of hesperetin and hesperidin and their inhibitory activity on COX-2 expression. Anticancer Research, 25(5), 3367-3374.
  15. Kaliaperumal, K., Zhang, L., Gao, L., Xiong, Q., Liang, Y., Jiang, Y., & Zhang, J. (2023). Insight into the Inhibitory Mechanisms of Hesperidin on α-Glucosidase through Kinetics, Fluorescence Quenching, and Molecular Docking Studies. Foods, 12(22), 4142. https://doi.org/10.3390/foods12224142
  16. Kamli, M.R., Sharaf, A.A.M., Sabir, J.S., & Rather, I.A. (2022). Phytochemical screening of Rosmarinus officinalis L. as a potential anticholinesterase and antioxidant–medicinal plant for cognitive decline disorders. Plants, 11(4), 514. https://doi.org/10.3390/plants11040514
  17. Kargın Solmaz, F.Ö., & Sarıkürkcü, C. (2025). Chemical composition, antioxidant properties, and enzyme inhibitory activities of methanol extract from Sideritis montana subsp. montana using ultrasound-assisted extraction. International Journal of Secondary Metabolite, 12(2), 461-471. https://doi.org/10.21448/ijsm.1628337
  18. Kocak, M.S., Sarikurkcu, C., Cengiz, M., Kocak, S., Uren, M.C., & Tepe, B. (2016). Salvia cadmica: Phenolic composition and biological activity. Industrial Crops and Products, 85, 204 212. https://doi.org/10.1016/j.indcrop.2016.03.015
  19. Malik, S., Brudzyńska, P., Khan, M.R., Sytar, O., Makhzoum, A., & Sionkowska, A. (2023). Natural plant-derived compounds in food and cosmetics: A paradigm of shikonin and its derivatives. Materials, 16(12), 4377. https://doi.org/10.3390/ma16124377
  20. Mir, S.A., Nayak, B., Khan, A., Khan, M.I., Eldakhakhny, B.M., & Arif, D.O. (2024). An exploration of binding of hesperidin, rutin, and thymoquinone to acetylcholinesterase enzyme using multi-level computational approaches. Journal of Biomolecular Structure and Dynamics, 42(21), 11901 11915. https://doi.org/10.1080/07391102.2023.2265492
  21. Ozer, M.S., Kirkan, B., Sarikurkcu, C., Cengiz, M., Ceylan, O., Atilgan, N., & Tepe, B. (2018). Onosma heterophyllum: Phenolic composition, enzyme inhibitory and antioxidant activities. Industrial Crops and Products, 111, 179-184. https://doi.org/10.1016/j.indcrop.2017.10.026
  22. Papageorgiou, V.P., Assimopoulou, A.N., Couladouros, E.A., Hepworth, D., & Nicolaou, K. (1999). The chemistry and biology of alkannin, shikonin, and related naphthazarin natural products. Angewandte Chemie International Edition, 38(3), 270-301. https://doi.org/10.1002/(SICI)1521-3773(19990201)38:3 3.0.CO;2-0
  23. Pekin, G., Ganzera, M., Senol, S., Bedir, E., Korkmaz, K.S., & Stuppner, H. (2007). Determination of naphthazarin derivatives in endemic Turkish Alkanna species by reversed phase high performance liquid chromatography. Planta Medica, 73(03), 267-272. https://doi.org/10.1055/s-2007-967110
  24. Sabih Ozer, M., Sarikurkcu, C., Tepe, B., & Can, S. (2010). Essential oil composition and antioxidant activities of alkanet (Alkanna tinctoria subsp. tinctoria). Food Science and Biotechnology, 19, 1177 1183. https://doi.org/10.1007/s10068-010-0168-x
  25. Salimikia, I., Yazdinezhad, A.R., Golfakhrabadi, F., & Esfahani, H.R.M. (2015). In vitro antioxidant and free radical scavenging activity of four Alkanna species growing in Iran. Pharmacognosy Research, 7(1), 100. https://doi.org/10.4103/0974-8490.147218
  26. Sarikurkcu, C., Locatelli, M., Mocan, A., Zengin, G., & Kirkan, B. (2020). Phenolic Profile and Bioactivities of Sideritis perfoliata L.: The Plant, Its Most Active Extract, and Its Broad Biological Properties. Frontiers in Pharmacology, 10, 1642. https://doi.org/10.3389/fphar.2019.01642
  27. Sarikurkcu, C., Ozer, M.S., Cakir, A., Eskici, M., & Mete, E. (2013). GC/MS evaluation and in vitro antioxidant activity of essential oil and solvent extracts of an endemic plant used as folk remedy in Turkey: Phlomis bourgaei Boiss. [Article]. Evidence-Based Complementary and Alternative Medicine, 2013, Article ID 293080, 293087 pages. https://doi.org/10.1155/2013/293080
  28. Sevimli-Gür, C., Bedir, E., Bıçkıcı, S., Nalbantoğlu, S., Şenol, S., Karayıldırım, T., Alankuş-Çalışkan, Ö., Deliloğlu-Gürhan, İ., & Korkmaz, K. (2009). Biological activities of Turkish Alkanna species. Planta Medica, 75(09), PE44. https://doi.org/10.1055/s-0029-1234605
  29. Si, Y.-X., Wang, Z.-J., Park, D., Chung, H.Y., Wang, S.-F., Yan, L., Yang, J.-M., Qian, G.-Y., Yin, S.-J., & Park, Y.-D. (2012). Effect of hesperetin on tyrosinase: Inhibition kinetics integrated computational simulation study. International Journal of Biological Macromolecules, 50(1), 257 262. https://doi.org/10.1016/j.ijbiomac.2011.11.001
  30. Tatsumi, K., Yano, M., Kaminade, K., Sugiyama, A., Sato, M., Toyooka, K., Aoyama, T., Sato, F., & Yazaki, K. (2016). Characterization of shikonin derivative secretion in Lithospermum erythrorhizon hairy roots as a model of lipid soluble metabolite secretion from plants. Frontiers in Plant Science, 7, 1066. https://doi.org/10.3389/fpls.2016.01066
  31. Tepe, B., Sarikurkcu, C., Berk, S., Alim, A., & Akpulat, H.A. (2011). Chemical composition, radical scavenging and antimicrobial activity of the essential oils of Thymus boveii and Thymus hyemalis. Records of Natural Products, 5(3), 208-220.
  32. Topal, M., & Gulcin, İ. (2022). Evaluation of the in vitro antioxidant, antidiabetic and anticholinergic properties of rosmarinic acid from rosemary (Rosmarinus officinalis L.). Biocatalysis and Agricultural Biotechnology, 43, 102417. https://doi.org/10.1016/j.bcab.2022.102417
  33. Vo, Q.V., Hoa, N.T., Flavel, M., Thong, N.M., Boulebd, H., Nam, P.C., Quang, D.T., & Mechler, A. (2023). A comprehensive study of the radical scavenging activity of rosmarinic acid. The Journal of Organic Chemistry, 88(24), 17237-17248. https://doi.org/10.1021/acs.joc.3c02093
  34. Zengin, G., Terzić, M., Abul, N., Gulcin, I., Koyuncu, I., Basarali, M.K., Đorđević, T., Cziáky, Z., Jekő, J., & Cespedes-Acuna, C.L. (2024). A multidimensional study for design functional foods: Chemical profiling, antioxidant potential, enzyme inhibition, and cytotoxic effects of Alkanna tubulosa extracts. Food Bioscience, 60, 104280. https://doi.org/10.1016/j.fbio.2024.104280
  35. Zengin, G., Uren, M.C., Kocak, M.S., Gungor, H., Locatelli, M., Aktumsek, A., & Sarikurkcu, C. (2017). Antioxidant and Enzyme Inhibitory Activities of Extracts from Wild Mushroom Species from Turkey. International Journal of Medicinal Mushrooms, 19(4), 327 336. https://doi.org/10.1615/intjmedmushrooms.v19.i4.30
  36. Zhu, F., Asada, T., Sato, A., Koi, Y., Nishiwaki, H., & Tamura, H. (2014). Rosmarinic acid extract for antioxidant, antiallergic, and α-glucosidase inhibitory activities, isolated by supramolecular technique and solvent extraction from Perilla leaves. Journal of Agricultural and Food Chemistry, 62(4), 885-892. https://doi.org/10.1021/jf404318j