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Secondary metabolites from Scabiosa atropurpurea and their antioxidant and xanthine oxidase inhibitory activities

Yıl 2024, Cilt: 28 Sayı: 1, 79 - 88, 28.06.2025

Ceren Öztürk Nisa Beril Şen Etil Güzelmeriç , Hasan Kırmızıbekmez

Öz

Two secoiridoid glycosides, lonicejaposide I (1) and secologanin dimethyl acetal (2), six flavonoids, isoorientin (3) hesperidin (4), apigenin 7-O-neohesperidoside (5), luteolin 7-O-b-D-glucopyranoside (6), kaempferol 3- O-(3'',6''-di-(E)-p-coumaroyl)-b-D-glucopyranoside (7), and kaempferol 3-O-(3''-O-acetyl, 6''-O-(E)-p-coumaroyl)-b-Dglycopyranoside (8), two caffeoylquinic acid derivatives, chlorogenic acid (9) and 3,5-dicaffeoylquinic acid (10) were isolated from the EtOAc and H2O subextracts of the crude MeOH extract prepared from the aerial parts of Scabiosa atropurpurea. Their structures were identified by extensive 1D and 2D NMR experiments as well as ESI-MS analysis. Xanthine oxidase (XO) inhibitory and antioxidant activities of the isolated compounds were evaluated by in vitro tests. Compounds, 3, 5, 6, 9 and 10 showed mild-to-moderate inhibitory effects on XO enzyme. The highest antioxidant activity was found for compound 10 according to results of DPPH, FRAP and CUPRAC assays. This is the first study on the XO inhibitory activities for compounds 1, 2, 5, 7 and 8.

Anahtar Kelimeler

Scabiosa atropurpurea secoiridoids flavonoids caffeoylquinic acid derivatives xanthine oxidase inhibitory activity; antioxidant activity

Kaynakça

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Yıl 2024, Cilt: 28 Sayı: 1, 79 - 88, 28.06.2025

Ceren Öztürk Nisa Beril Şen Etil Güzelmeriç , Hasan Kırmızıbekmez

Öz

Kaynakça

  • [1] Pinto DCGA, Rahmouni N, Beghidja N, Silva AMS. Scabiosa Genus: A rich source of bioactive metabolites. Medicines. 2018; 5(4): 110. https://doi.org/10.3390/medicines5040110
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  • [3] Bendamene S, Boutaghane N, Bellik Y, Sayagh C, AlabdukMagid A, Harakat D, Kabouche Z, Voutquenne-Nazabadioko L. Semipapposides A-M, triterpenoid bidesmosides saponins from the roots of Scabiosa semipapposa. Phytochemistry. 2020; 180: 112526. https://doi.org/10.1016/j.phytochem.2020.112526
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  • [13] Polat E, Alankus-Caliskan Ö, Karayildirim T, Bedir E. Iridoids from Scabiosa atropurpurea L. subsp. maritima Arc. (L.). Biochem Syst Ecol 2010; 38(2): 253-255. https://doi.org/10.1016/j.bse.2010.01.004
  • [14] Umamaheswari M, AsokKumar K, Somasundaram A, Sivashanmugam T, Subhadradevi V, Ravi TK. Xanthine oxidase inhibitory activity of some Indian medical plants. J Ethnopharmacol. 2007; 109(3): 547-551. https://doi.org/10.1016/j.jep.2006.08.020
  • [15] Chen J, Li Q, Ye Y, Ran M, Ruan Z, Jin N. Inhibition of xanthine oxidase by theaflavin: Possible mechanism for anti-hyperuricaemia effect in mice. Process Biochem. 2020; 97: 11-18. https://doi.org/10.1016/j.procbio.2020.06.024
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  • [17] Song JU, Jang JW, Kim TH, Park H, Park WS, Jung SH, Kim GT. Structure-based design and biological evaluation of novel 2-(indol-2-yl) thiazole derivatives as xanthine oxidase inhibitors. Bioorg Med Chem Lett. 2016; 26(3): 950-954. https://doi.org/10.1016/j.bmcl.2015.12.055
  • [18] Mohamed Isa SSP, Ablat A, Mohamad J. The Antioxidant and xanthine oxidase inhibitory activity of Plumeria rubra flowers. Molecules. 2018; 23(2): 400. https://doi.org/10.3390/molecules23020400
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  • [20] Pacher P, Nivorozhkin A, Szabó C. Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006; 58(1): 87-114. https://doi.org/10.1124/pr.58.1.6
  • [21] Lin S, Zhang G, Liao Y, Pan J, Gong D. Dietary flavonoids as xanthine oxidase inhibitors: Structure–affinity and structure–activity relationships. J Agric Food Chem. 2015; 63(35): 7784-7794. https://doi.org/10.1021/acs.jafc.5b03386
  • [22] Cos P, Ying L, Calomme M, Hu JP, Cimanga K, Van Poel B, Pieters L, Vlietinck AJ, Berghe DV. Structure−activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. J Nat Prod. 1998; 61(1): 71-76. https://doi.org/10.1021/np970237h
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  • [27] Zhang H, Li X, Wu K, Wang M, Liu P, Wang X, Deng R. Antioxidant activities and chemical constituents of flavonoids from the flower of Paeonia ostii. Molecules. 2016; 22(1): 5. https://doi.org/10.3390/molecules22010005
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  • [29] Liu H, Orjala J, Sticher O, Rali T. Acylated flavonol glycosides from leaves of Stenochlaena palustris. J Nat Prod. 1999; 62(1): 70-75. https://doi.org/10.1021/np980179f
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  • [35] Olszowy M. What is responsible for antioxidant properties of polyphenolic compounds from plants?. Plant Physiol Biochem. 2019; 144: 135-143. https://doi.org/10.1016/j.plaphy.2019.09.039
  • [36] Jiang XW, Bai JP, Zhang Q, Hu XL, Tian X, Zhu J, Liu J, Meng WH, Zhao QC. Caffeoylquinic acid derivatives from the roots of Arctium lappa L.(burdock) and their structure–activity relationships (SARs) of free radical scavenging activities. Phytochem Lett. 2016; 15: 159-163. http://doi.org/10.1016/j.phytol.2015.12.008
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Toplam 54 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Farmakognozi
Bölüm Articles
Yazarlar

Ceren Öztürk 0009-0008-5642-1601

Nisa Beril Şen 0000-0001-8422-8835

Etil Güzelmeriç 0000-0001-9696-3271

Hasan Kırmızıbekmez 0000-0002-6118-8225

Yayımlanma Tarihi 28 Haziran 2025
Yayımlandığı Sayı Yıl 2024 Cilt: 28 Sayı: 1

Kaynak Göster

APA Öztürk, C., Şen, N. B., Güzelmeriç, E., Kırmızıbekmez, H. (2025). Secondary metabolites from Scabiosa atropurpurea and their antioxidant and xanthine oxidase inhibitory activities. Journal of Research in Pharmacy, 28(1), 79-88.
AMA Öztürk C, Şen NB, Güzelmeriç E, Kırmızıbekmez H. Secondary metabolites from Scabiosa atropurpurea and their antioxidant and xanthine oxidase inhibitory activities. J. Res. Pharm. Haziran 2025;28(1):79-88.
Chicago Öztürk, Ceren, Nisa Beril Şen, Etil Güzelmeriç, ve Hasan Kırmızıbekmez. “Secondary Metabolites from Scabiosa Atropurpurea and Their Antioxidant and Xanthine Oxidase Inhibitory Activities”. Journal of Research in Pharmacy 28, sy. 1 (Haziran 2025): 79-88.
EndNote Öztürk C, Şen NB, Güzelmeriç E, Kırmızıbekmez H (01 Haziran 2025) Secondary metabolites from Scabiosa atropurpurea and their antioxidant and xanthine oxidase inhibitory activities. Journal of Research in Pharmacy 28 1 79–88.
IEEE C. Öztürk, N. B. Şen, E. Güzelmeriç, ve H. Kırmızıbekmez, “Secondary metabolites from Scabiosa atropurpurea and their antioxidant and xanthine oxidase inhibitory activities”, J. Res. Pharm., c. 28, sy. 1, ss. 79–88, 2025.
ISNAD Öztürk, Ceren vd. “Secondary Metabolites from Scabiosa Atropurpurea and Their Antioxidant and Xanthine Oxidase Inhibitory Activities”. Journal of Research in Pharmacy 28/1 (Haziran 2025), 79-88.
JAMA Öztürk C, Şen NB, Güzelmeriç E, Kırmızıbekmez H. Secondary metabolites from Scabiosa atropurpurea and their antioxidant and xanthine oxidase inhibitory activities. J. Res. Pharm. 2025;28:79–88.
MLA Öztürk, Ceren vd. “Secondary Metabolites from Scabiosa Atropurpurea and Their Antioxidant and Xanthine Oxidase Inhibitory Activities”. Journal of Research in Pharmacy, c. 28, sy. 1, 2025, ss. 79-88.
Vancouver Öztürk C, Şen NB, Güzelmeriç E, Kırmızıbekmez H. Secondary metabolites from Scabiosa atropurpurea and their antioxidant and xanthine oxidase inhibitory activities. J. Res. Pharm. 2025;28(1):79-88.