Startseite Lebenswissenschaften Exploring phytochemical constituents of Achillea arabica Kotschy. ethanolic flower extract by LC-MS/MS and its possible antioxidant and antidiabetic effects in diabetic rats
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

Exploring phytochemical constituents of Achillea arabica Kotschy. ethanolic flower extract by LC-MS/MS and its possible antioxidant and antidiabetic effects in diabetic rats

  • Hanife Ceren Hanalp ORCID logo , Abdulahad Dogan ORCID logo EMAIL logo , Tuba Kusman Saygi ORCID logo , Fatih Donmez ORCID logo und Abdulhamit Battal ORCID logo
Veröffentlicht/Copyright: 30. Juni 2022
Zeitschrift für Naturforschung C
Aus der Zeitschrift Zeitschrift für Naturforschung C Band 78 Heft 5-6

Abstract

The aim of this study was to reveal the antidiabetic and antioxidant effects of ethanolic lyophilized extract of Achillea arabica flower extract against streptozotosine (STZ)-induced in diabetic rats and to determine its phytochemical content by liquid chromatography with tandem mass spectrometry (LC-MS/MS). After toxicity test, 35 female rats were divided into five groups. Control, diabetes mellitus (DM), A.arabica (400 mg/kg) extract, DM + A. arabica (400 mg/kg) extract and DM + Glibenclamide (2 mg/kg). It was determined that while diabetic rats treated A.arabica plant extract significantly decreased blood glucose level, serum glucose, HbA1c, liver and kidney damage biomarker levels, and malondialdehyde (MDA) content compared to the DM group, it caused fluctuations in antioxidant enzyme levels. According to LC-MS/MS results of A. arabica flower extract, quinic acid (2439.9 μg/g), cyranoside (858.4 μg/g), chlorogenic acid (698.7 μg/g), and cosmosiin (347.8 μg/g) were determined as major compounds, respectively. In addition, two new compounds were determined in this extract according to nuclear magnetic resonance (NMR) and Mass analyses and these compounds were named edremitine and achillosine, respectively. Thus, A.arabica flower extract has possible therapeutic effects to prevent high blood glucose level and oxidative stress caused by DM in liver and kidney via its high phenolic content.

Keywords: A. arabica ; diabetes mellitus; LC-MS/MS; NMR; oxidative stress
Corresponding author: Abdulahad Dogan, Department of Biochemistry, Faculty of Pharmacy, Van Yuzuncu Yil University, Van 65080, Turkey, E-mail:

Funding source: Van Yuzuncu Yil University

Award Identifier / Grant number: TYL-2019-7865

Acknowledgments

Authors are thankful to Süleyman Mesut PINAR for botanical identification of the plant materials. Authors are also grateful to Dicle University Science and Technology Researchand Application Center (DUBTAM) for providing laboratory facilities.

  1. Author contributions: A. Dogan: Study design, writing-review & editing. H. C. Hanalp: Performing in vivo analyzes. T. Kusman Saygı: In vitro analyzes to be performed. F. Donmez: Contributed to manuscript review and biochemical analysis. A. Battal: Contributed in manuscript writing and review.

  2. Research funding: This study was supported by Van Yuzuncu Yil University Scientific Research Project Commission (Grant number TYL-2019-7865).

  3. Conflict of interest statement: The authors declare that they have no competing interest.

  4. Ethical approval: The procedures conducted herein were in line with those of the National and Institutional Regulations for the Protection of Animal Welfare. The animal used, and all of the experimental procedures during the study, were approved of by the Animal Experiments Ethics Committee of Van Yuzuncu Yil University for ethical concerns (YUHADYEK-2019/06).

References

1. Wichtl, M. Teedrogen und Phytopharmaka, 4th ed. Stuttgart: Wissenschaftliche Verlagsgesellschaft mbH; 2002.Suche in Google Scholar

2. Burk, DR, Cichacz, ZA, Daskalova, SM. Aqueous extract of Achillea millefolium L. (Asteraceae) inflorescences suppresses lipopolysaccharide-induced inflammatory responses in RAW 264.7 murine macrophages. J Med Plants Res 2010;4:225–34.10.1016/j.jep.2009.09.026Suche in Google Scholar PubMed

3. Salehi, B, Selamoglu, Z, Sevindik, M, Fahmy, NM, Al-Sayed, E, El-Shazly, M, et al.. Achillea spp.: a comprehensive review on its ethnobotany, phytochemistry, phytopharmacology and industrial applications. Cell Mol Biol 2020;66:78–103. https://doi.org/10.14715/cmb/2020.66.4.13.Suche in Google Scholar

4. Aburjai, T, Hudaib, M. Antiplatelet, antibacterial and antifungal activities of Achillea falcata extracts and evaluation of volatile oil composition. Pharmacogn Mag 2006;2:191–8.Suche in Google Scholar

5. Jaffal, SM, Abbas, MA. Antinociceptive action of Achillea biebersteinii methanolic flower extract is mediated by interaction with cholinergic receptor in mouse pain models. Inflammopharmacology 2019;27:961–8. https://doi.org/10.1007/s10787-018-0524-7.Suche in Google Scholar PubMed

6. Akkol, EK, Koca, U, Pesin, I, Yilmazer, D. Evaluation of the wound healing potential of Achillea biebersteinii Afan. (Asteraceae) by in vivo excision and incision models. Evid Based Complement Alternat Med 2011;2011:1–7. https://doi.org/10.1093/ecam/nep039.Suche in Google Scholar PubMed PubMed Central

7. Varasteh-Kojourian, M, Abrishamchi, P, Matin, MM, Asili, J, Ejtehadi, H, Khosravitabar, F. Antioxidant, cytotoxic and DNA protective properties of Achillea eriophora DC. and Achillea biebersteinii Afan. extracts: a comparative study. Avicenna J Phytomed 2017;7:157–68.Suche in Google Scholar

8. Abd-Alla, HI, Shalaby, NM, Hamed, MA, El-Rigal, NS, Al-Ghamdi, SN, Bouajila, J. Phytochemical composition, protective and therapeutic effect on gastric ulcer and α-amylase inhibitory activity of Achillea biebersteinii Afan. Arch Pharm Res (Seoul) 2016;39:10–20. https://doi.org/10.1007/s12272-014-0544-9.Suche in Google Scholar PubMed

9. Hammad, HM, Albu, C, Matar, SA, Litescu, SC, Al Jaber, HI, Abualraghib, AS, et al.. Biological activities of the hydro-alchoholic and aqueous extracts of Achillea biebersteinii Afan. (Asteraceae) grown in Jordan. Afr J Pharmacy Pharmacol 2013;7:1686–94. https://doi.org/10.5897/ajpp2012.1490.Suche in Google Scholar

10. Zengin, G, Sarikurkcu, C, Aktumsek, A, Ceylan, R, Ceylan, O. A comprehensive study on phytochemical characterization of Haplophyllum myrtifolium Boiss. endemic to Turkey and its inhibitory potential against key enzymes involved in Alzheimer, skin diseases and type II diabetes. Ind Crops Prod 2014;53:244–51. https://doi.org/10.1016/j.indcrop.2013.12.043.Suche in Google Scholar

11. Agirman, E, Celik, I, Dogan, A. Consumption of the Syrian mesquite plant (Prosopis farcta) fruit and seed lyophilized extracts may have both protective and toxic effects in STZ-induced diabetic rats. Arch Physiol Biochem 2020:1–10. https://doi.org/10.1080/13813455.2020.1734844.Suche in Google Scholar PubMed

12. Ogurtsova, K, da Rocha Fernandes, JD, Huang, Y, Linnenkamp, U, Guariguata, L, Cho, NH, et al.. IDF Diabetes Atlas: Global estimates for the prevalence of diabetes for 2015 and 2040. Diabetes Res Clin Pract 2017;128:40–50. https://doi.org/10.1016/j.diabres.2017.03.024.Suche in Google Scholar PubMed

13. Dewanjee, S, Chakraborty, P, Mukherjee, B, De Feo, V. Plant-based antidiabetic nanoformulations: the emerging paradigm for effective therapy. Int J Mol Sci 2020;21:2217. https://doi.org/10.3390/ijms21062217.Suche in Google Scholar PubMed PubMed Central

14. Yilmaz, MA, Ertas, A, Yener, I, Akdeniz, M, Cakir, O, Altun, M, et al.. A comprehensive LC–MS/MS method validation for the quantitative investigation of 37 fingerprint phytochemicals in Achillea species: a detailed examination of A. coarctata and A. monocephala. J Pharm Biomed 2018;154:413–24. https://doi.org/10.1016/j.jpba.2018.02.059.Suche in Google Scholar PubMed

15. Dogan, A, Dalar, A, Sadullahoglu, C, Battal, A, Uzun, Y, Celik, I, et al.. Investigation of the protective effects of horse mushroom (Agaricus arvensis Schaeff.) against carbon tetrachloride-induced oxidative stress in rats. Mol Biol Rep 2018;45:787–97. https://doi.org/10.1007/s11033-018-4218-4.Suche in Google Scholar PubMed

16. Dogan, A, Celik, I. Hepatoprotective and antioxidant activities of grapeseeds against ethanol-induced oxidative stress in rats. Br J Nutr 2012;107:45–51. https://doi.org/10.1017/s0007114511002650.Suche in Google Scholar PubMed

17. Bradford, MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248–54. https://doi.org/10.1016/0003-2697(76)90527-3.Suche in Google Scholar

18. Beutler, E. Improved method for the determination of blood glutathione. J Lab Clin Med 1963;61:882–8.Suche in Google Scholar

19. Buege, JA, Aust, SD. Microsomal lipid peroxidation. In: Abelson, J, Simon, MI, Verdine, GL, Pyle, AM, editors. Methods in enzymology, New York: Academic Press; 1978, vol 52:302–10 pp.10.1016/S0076-6879(78)52032-6Suche in Google Scholar

20. Paglia, DE, Valentine, WN. Studies on the quantitative and qualitative characterization of erythrocyte glutathione peroxidase. J Lab Clin Med 1976;70:158–69.Suche in Google Scholar

21. McCord, JM, Fridovich, I. Superoxide dismutase: an enzymic function for erythrocuprein (hemocuprein). J Biol Chem 1969;244:6049–55. https://doi.org/10.1016/s0021-9258(18)63504-5.Suche in Google Scholar

22. Mannervik, B, Guthenberg, C. Glutathione transferase (human placenta). In: Jakoby, WB, editor. Methods in enzymology, New York: Academic Press; 1981, vol 77:231–5 pp.10.1016/S0076-6879(81)77030-7Suche in Google Scholar PubMed

23. Aebi, H. Catalase. In: Bergemeyer, HU, editor. Methods of enzymatic analysis, New York: Academic Press; 1974, vol 2:673–84 pp.10.1016/B978-0-12-091302-2.50032-3Suche in Google Scholar

24. Yilmaz, MA. Simultaneous quantitative screening of 53 phytochemicals in 33 species of medicinal and aromatic plants: a detailed, robust and comprehensive LC–MS/MS method validation. Ind Crops Prod 2020;149:112347. https://doi.org/10.1016/j.indcrop.2020.112347.Suche in Google Scholar

25. Ahmadi, K, Wassim, A, Ream, N. Evaluation of hypoglycemic effect of Achillea biebersteinii Afan., growing in Syria, in induced diabetic rats. Int J Pharm Phytochem Res 2017;9:215–22. https://doi.org/10.25258/phyto.v9i2.8065.Suche in Google Scholar

26. Jaffal, SM, Abbas, MA. Antinociceptive action of Achillea biebersteinii methanolic flower extract is mediated by interaction with cholinergic receptor in mouse pain models. Inflammopharmacology 2019;27:961–8. https://doi.org/10.1007/s10787-018-0524-7.Suche in Google Scholar PubMed

27. Mottaghi, M, Salehi Shanjani, P, Jafari, AA, Mirza, M, Bihamta, MR. Essential oil composition of Achillea filipendulina, A. arabica and A. eriophora cultivated under temperate climate in Iran. J Med Plants 2016;5:153–8.Suche in Google Scholar

28. Kaffash, S, Sefidkon, F, Mafakheri, S. Comparing essential oil composition of cultivated and wild samples of Achillea biebersteinii afan in Kurdistan Province. J Med Plants 2020;9:149–58.Suche in Google Scholar

29. Dehghan, G, Elmi, F. Essential oil combination of three species of Achillea growing wild in East Azarbayjan-Iran. Future Nat Prod 2015;1:22–8.Suche in Google Scholar

30. Morteza-Semnani, K, Akbarzadeh, M, Moshiri, K. The essential oil composition of Achillea biebersteinii Afan. J Essent Oil-Bear Plants 2005;8:200–3. https://doi.org/10.1080/0972060x.2005.10643445.Suche in Google Scholar

31. Sökmen, A, Sökmen, M, Daferera, D, Polissiou, M, Candan, F, Ünlü, M, et al.. The in vitro antioxidant and antimicrobial activities of the essential oil and methanol extracts of Achillea biebersteini Afan. (Asteraceae). Phytother Res 2004;18:451–6.10.1002/ptr.1438Suche in Google Scholar PubMed

32. Dogan, A, Celik, I, Kaya, MS. Antidiabetic properties of lyophilized extract of acorn (Quercus brantii Lindl.) on experimentally STZ-induced diabetic rats. J Ethnopharmacol 2015;176:243–51. https://doi.org/10.1016/j.jep.2015.10.034.Suche in Google Scholar PubMed

33. Demirbolat, I, Ekinci, C, Nuhoğlu, F, Kartal, M, Yıldız, P, Geçer, MÖ. Effects of orally consumed Rosa damascena Mill. Hydrosol on hematology, clinical chemistry, lens enzymatic activity, and lens pathology in streptozotocin-induced diabetic rats. Molecules 2019;24:4069. https://doi.org/10.3390/molecules24224069.Suche in Google Scholar PubMed PubMed Central

34. Bhatti, JS, Bhatti, GK, Reddy, PH. Mitochondrial dysfunction and oxidative stress in metabolic disorders-A step towards mitochondria based therapeutic strategies. Biochim Biophys Acta, Mol Basis Dis 2017;1863:1066–77. https://doi.org/10.1016/j.bbadis.2016.11.010.Suche in Google Scholar PubMed PubMed Central

35. Rezaei, S, Ashkar, F, Koohpeyma, F, Mahmoodi, M, Gholamalizadeh, M, Mazloom, Z, et al.. Hydroalcoholic extract of Achillea millefolium improved blood glucose, liver enzymes and lipid profile compared to metformin in streptozotocin-induced diabetic rats. Lipids Health Dis 2020;19:1–7. https://doi.org/10.1186/s12944-020-01228-4.Suche in Google Scholar PubMed PubMed Central

36. Hanalp, HC, Kaptaner, B, Doğan, A. Protective effects of lyophilized ethanolic extract of Achillea arabica Kotschy. On the islet β cells of streptozotocin-induced diabetic rats. KSU J Agric Nat 2021;24:689–700.10.18016/ksutarimdoga.vi.811253Suche in Google Scholar

37. Daisy, P, Eliza, J, Ignacimuthu, S. Influence of Costus speciosus (Koen.) Sm. Rhizome extracts on biochemical parameters in streptozotocin induced diabetic rats. J Health Sci 2008;54:675–81. https://doi.org/10.1248/jhs.54.675.Suche in Google Scholar

38. Al-Said, MS, Mothana, RA, Al-Yahya, MM, Rafatullah, S, Al-Sohaibani, MO, Khaled, JM, et al.. GC-MS analysis: in vivo hepatoprotective and antioxidant activities of the essential oil of Achillea biebersteinii afan. Growing in Saudi Arabia. Evid Based Complement Alternat Med 2016;2016:1–8. https://doi.org/10.1155/2016/1867048.Suche in Google Scholar PubMed PubMed Central

39. West, IC. Radicals and oxidative stress in diabetes. Diabet Med 2000;17:171–80. https://doi.org/10.1046/j.1464-5491.2000.00259.x.Suche in Google Scholar PubMed

40. Dogan, A, Anuk, OO. Investigation of the phytochemical composition and antioxidant properties of chinar (Platanus orientalis L.) leaf infusion against ethanol-induced oxidative stress in rats. Mol Biol Rep 2019;46:3049–61. https://doi.org/10.1007/s11033-019-04741-7.Suche in Google Scholar PubMed

41. Mohamed, AEHH, Mohamed, NS, Hamed, AR, Hegazy, MEF. Anti-inflammatory activity of highly oxygenated terpenoids from Achillea biebersteinii Afan. Z Naturforsch C Bio Sci 2016;71:429–32. https://doi.org/10.1515/znc-2016-0098.Suche in Google Scholar PubMed

42. Pero, RW, Lund, H, Leanderson, T. Antioxidant metabolism induced by quinic acid. Increased urinary excretion of tryptophan and nicotinamide. Phytother Res 2009;23:335–46. https://doi.org/10.1002/ptr.2628.Suche in Google Scholar PubMed

43. McDougall, B, King, PJ, Wu, BW, Hostomsky, Z, Reinecke, MG, Robinson, WEJr. Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase. Antimicrob Agents Chemother 1998;42:140–6. https://doi.org/10.1128/aac.42.1.140.Suche in Google Scholar

44. Tamura, H, Akioka, T, Ueno, K, Chujyo, T, Okazaki, KI, King, PJ, et al.. Anti-human immunodeficiency virus activity of 3,4,5-tricaffeoylquinic acid in cultured cells of lettuce leaves. Mol Nutr Food Res 2006;50:396–400. https://doi.org/10.1002/mnfr.200500216.Suche in Google Scholar PubMed

45. Patocka, J, Navratilova, Z. Achillea fragrantissima: pharmacology review. Clin Oncol 2019;4:1601.Suche in Google Scholar

46. Ceylan, R, Zengin, G, Mahomoodally, MF, Sinan, KI, Ak, G, Jugreet, S, et al.. Enzyme inhibition and antioxidant functionality of eleven Inula species based on chemical components and chemometric insights. Biochem Syst Ecol 2021;95:104225. https://doi.org/10.1016/j.bse.2021.104225.Suche in Google Scholar

47. Lee, HJ, Sim, MO, Woo, KW, Jeong, DE, Jung, HK, An, B, et al.. Antioxidant and antimelanogenic activities of compounds isolated from the aerial parts of Achillea alpina L. Chem Biodivers 2019;16:e1900033. https://doi.org/10.1002/cbdv.201900033.Suche in Google Scholar PubMed

48. Hichri, F, Znati, M, Jannet, HB, Bouajila, J. A new sesquiterpene lactone and secoguaianolides from Achillea cretica L. growing in Tunisia. Ind Crops Prod 2015;77:735–40. https://doi.org/10.1016/j.indcrop.2015.09.033.Suche in Google Scholar

49. Fahed, L, El Beyrouthy, M, Ouaini, N, Eparvier, V, Stien, D. Isolation and characterization of santolinoidol, a bisabolene sesquiterpene from Achillea santolinoides subsp wilhelmsii (K. Koch) Greuter. Tetrahedron Lett 2016;57:1892–4. https://doi.org/10.1016/j.tetlet.2016.03.059.Suche in Google Scholar

50. Trifunović, S, Isaković, AM, Isaković, A, Vučković, I, Mandić, B, Novaković, M, et al.. Isolation, characterization and in vitro cytotoxicity of new sesquiterpenoids from Achillea clavennae. Planta Med 2014;80:275–305.10.1055/s-0033-1360312Suche in Google Scholar PubMed

51. Loggia, RD, Sosa, S, Tubaro, A, Kastner, U, Jurenitsch, J. Anti-inflammatory principles from Achillea asplenifolia and Achillea pratensis. Planta Med 1992;58:641–2. https://doi.org/10.1055/s-2006-961648.Suche in Google Scholar

Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2022-0082).

Received: 2022-04-11
Accepted: 2022-06-10
Published Online: 2022-06-30
Published in Print: 2023-05-25

© 2022 Walter de Gruyter GmbH, Berlin/Boston

Artikel in diesem Heft

  1. Frontmatter
  2. Research Articles
  3. A novel eudesmol derivative from the leaf essential oil of Guatteria friesiana (Annonaceae) and evaluation of the antinociceptive activity
  4. Chemical constituents of Desmodium triflorum and their antifungal activity against various phytopathogenic fungi
  5. Exploring phytochemical constituents of Achillea arabica Kotschy. ethanolic flower extract by LC-MS/MS and its possible antioxidant and antidiabetic effects in diabetic rats
  6. Chemical constituents from Ficus sur Forssk (Moraceae)
  7. In vitro acetylcholinesterase, tyrosinase inhibitory potentials of secondary metabolites from Euphorbia schimperiana and Euphorbia balsamifera
  8. Furoquinoline and bisindole alkaloids from the roots of Teclea nobilis and their in-silico molecular docking analysis
  9. Limonoids and insecticidal activity on Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae) of Trichilia catigua A. Juss. (Meliaceae)
  10. Tissue specific changes of phytochemicals, antioxidant, antidiabetic and anti-inflammatory activities of tea [Camellia sinensis (L.)] extracted with different solvents
  11. Anonazepine, a new alkaloid from the leaves of Annona muricata (Annonaceae)
  12. Two new natural products from Portulaca oleracea L. and their bioactivities
https://doi.org/10.1515/znc-2022-0082
Schlagwörter für diesen Artikel
A. arabica; diabetes mellitus; LC-MS/MS; NMR; oxidative stress

Artikel in diesem Heft

  1. Frontmatter
  2. Research Articles
  3. A novel eudesmol derivative from the leaf essential oil of Guatteria friesiana (Annonaceae) and evaluation of the antinociceptive activity
  4. Chemical constituents of Desmodium triflorum and their antifungal activity against various phytopathogenic fungi
  5. Exploring phytochemical constituents of Achillea arabica Kotschy. ethanolic flower extract by LC-MS/MS and its possible antioxidant and antidiabetic effects in diabetic rats
  6. Chemical constituents from Ficus sur Forssk (Moraceae)
  7. In vitro acetylcholinesterase, tyrosinase inhibitory potentials of secondary metabolites from Euphorbia schimperiana and Euphorbia balsamifera
  8. Furoquinoline and bisindole alkaloids from the roots of Teclea nobilis and their in-silico molecular docking analysis
  9. Limonoids and insecticidal activity on Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae) of Trichilia catigua A. Juss. (Meliaceae)
  10. Tissue specific changes of phytochemicals, antioxidant, antidiabetic and anti-inflammatory activities of tea [Camellia sinensis (L.)] extracted with different solvents
  11. Anonazepine, a new alkaloid from the leaves of Annona muricata (Annonaceae)
  12. Two new natural products from Portulaca oleracea L. and their bioactivities
Jetzt anmelden und 20% sparen
Institutioneller Zugang
Wie funktioniert Authentifizierung?
Haben Sie eine Idee, wie wir unsere Website verbessern können?
Bitte schreiben Sie uns.
© 2025 De Gruyter Brill
Heruntergeladen am 30.12.2025 von https://www.degruyterbrill.com/document/doi/10.1515/znc-2022-0082/html
Button zum nach oben scrollen