Isolation of chemical constituents of centaurea virgata lam. and xanthine oxidase inhibitory activity of the plant extract and compounds

Burcu S. Tüzün, Zsuzsanna Hajdú, Orsolya Orbán-Gyapai, Zoltán P. Zomborszki, Nikoletta Jedlinszki, P. Forgó, Bijen Vçak, J. Hohmann

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Background: Centaurea virgata Lam. is a species widely used in the traditional medicine in Turkey for the treatment of diabetes, allergy and gastric ulcers. The rationale of its use in the therapy has not been studied previously, therefore the present work aimed at the chemical-pharmacological evaluation of the plant. Objective: The xanthine oxidase (XO) inhibitory activity of the MeOH extract and its subextracts (n-hexane, CHCl3 and remaining MeOH-H2O) prepared from C. virgata was investigated in vitro. Moderate activity was exerted in case of the CHCl3 extract (98.9 ± 15.8 g/mL), therefore constituents of this extract were analysed. Method: Different purification steps, such as VLC, CPC, PLC and crystallization were used for the isolation, and ESIMS, NMR, LC-MS and authentic standards were applied for identification of the compounds. XO inhibitory and DPPH assays were used for evaluation of the bioactivities. Results: Sesquiterpenes [8-hydroxysonchucarpolide, 8-(3,4-dihydroxy-2-methylene-butanoyloxy)-dehydromelitensine, and cnicin], flavones (apigenin, hispidulin, salvigenin, eupatorin, 3’-methyleupatorin), and the flavonol isokaempferide were isolated from the active extract. The XO-inhibitory activity of these compounds was analyzed using allopurinol as a positive control (IC50 7.49 ± 0.29 M). It was found that sesquiterpenes and flavonoids, containing 7-OMe group, are inactive. Conclusion: 7-Hydroxyflavones (apigenin and hispidulin) exerted significant XO inhibitory effect with IC50 values of 0.99 ± 0.33 M and 4.88 ± 1.21 M, respectively. Therefore, these compounds are responsible for the XO-inhibitory effect of the extract. The free radical scavenging activity of the isolated flavonoids was determined by DPPH assay, and it was stated that none of the compounds have substantial antioxidant activity, therefore the reduced generation of reactive oxygen species may be the consequence only of XO inhibition.

Original languageEnglish
Pages (from-to)498-502
Number of pages5
JournalMedicinal Chemistry
Volume13
Issue number5
DOIs
Publication statusPublished - Aug 1 2017

Fingerprint

Centaurea
Xanthine Oxidase
Plant Extracts
Apigenin
Sesquiterpenes
Flavonoids
Inhibitory Concentration 50
Flavones
Allopurinol
Traditional Medicine
Stomach Ulcer
Crystallization
Turkey
Free Radicals
Reactive Oxygen Species
Hypersensitivity
Antioxidants
Pharmacology
Therapeutics

Keywords

  • Asteraceae
  • Centaurea virgata
  • Flavonoids
  • Sesquiterpenes
  • Xanthine oxidase inhibitory activity

ASJC Scopus subject areas

  • Drug Discovery

Cite this

Isolation of chemical constituents of centaurea virgata lam. and xanthine oxidase inhibitory activity of the plant extract and compounds. / Tüzün, Burcu S.; Hajdú, Zsuzsanna; Orbán-Gyapai, Orsolya; Zomborszki, Zoltán P.; Jedlinszki, Nikoletta; Forgó, P.; Vçak, Bijen; Hohmann, J.

In: Medicinal Chemistry, Vol. 13, No. 5, 01.08.2017, p. 498-502.

Research output: Contribution to journalArticle

Tüzün, Burcu S. ; Hajdú, Zsuzsanna ; Orbán-Gyapai, Orsolya ; Zomborszki, Zoltán P. ; Jedlinszki, Nikoletta ; Forgó, P. ; Vçak, Bijen ; Hohmann, J. / Isolation of chemical constituents of centaurea virgata lam. and xanthine oxidase inhibitory activity of the plant extract and compounds. In: Medicinal Chemistry. 2017 ; Vol. 13, No. 5. pp. 498-502.
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abstract = "Background: Centaurea virgata Lam. is a species widely used in the traditional medicine in Turkey for the treatment of diabetes, allergy and gastric ulcers. The rationale of its use in the therapy has not been studied previously, therefore the present work aimed at the chemical-pharmacological evaluation of the plant. Objective: The xanthine oxidase (XO) inhibitory activity of the MeOH extract and its subextracts (n-hexane, CHCl3 and remaining MeOH-H2O) prepared from C. virgata was investigated in vitro. Moderate activity was exerted in case of the CHCl3 extract (98.9 ± 15.8 g/mL), therefore constituents of this extract were analysed. Method: Different purification steps, such as VLC, CPC, PLC and crystallization were used for the isolation, and ESIMS, NMR, LC-MS and authentic standards were applied for identification of the compounds. XO inhibitory and DPPH assays were used for evaluation of the bioactivities. Results: Sesquiterpenes [8-hydroxysonchucarpolide, 8-(3,4-dihydroxy-2-methylene-butanoyloxy)-dehydromelitensine, and cnicin], flavones (apigenin, hispidulin, salvigenin, eupatorin, 3’-methyleupatorin), and the flavonol isokaempferide were isolated from the active extract. The XO-inhibitory activity of these compounds was analyzed using allopurinol as a positive control (IC50 7.49 ± 0.29 M). It was found that sesquiterpenes and flavonoids, containing 7-OMe group, are inactive. Conclusion: 7-Hydroxyflavones (apigenin and hispidulin) exerted significant XO inhibitory effect with IC50 values of 0.99 ± 0.33 M and 4.88 ± 1.21 M, respectively. Therefore, these compounds are responsible for the XO-inhibitory effect of the extract. The free radical scavenging activity of the isolated flavonoids was determined by DPPH assay, and it was stated that none of the compounds have substantial antioxidant activity, therefore the reduced generation of reactive oxygen species may be the consequence only of XO inhibition.",
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AU - Orbán-Gyapai, Orsolya

AU - Zomborszki, Zoltán P.

AU - Jedlinszki, Nikoletta

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N2 - Background: Centaurea virgata Lam. is a species widely used in the traditional medicine in Turkey for the treatment of diabetes, allergy and gastric ulcers. The rationale of its use in the therapy has not been studied previously, therefore the present work aimed at the chemical-pharmacological evaluation of the plant. Objective: The xanthine oxidase (XO) inhibitory activity of the MeOH extract and its subextracts (n-hexane, CHCl3 and remaining MeOH-H2O) prepared from C. virgata was investigated in vitro. Moderate activity was exerted in case of the CHCl3 extract (98.9 ± 15.8 g/mL), therefore constituents of this extract were analysed. Method: Different purification steps, such as VLC, CPC, PLC and crystallization were used for the isolation, and ESIMS, NMR, LC-MS and authentic standards were applied for identification of the compounds. XO inhibitory and DPPH assays were used for evaluation of the bioactivities. Results: Sesquiterpenes [8-hydroxysonchucarpolide, 8-(3,4-dihydroxy-2-methylene-butanoyloxy)-dehydromelitensine, and cnicin], flavones (apigenin, hispidulin, salvigenin, eupatorin, 3’-methyleupatorin), and the flavonol isokaempferide were isolated from the active extract. The XO-inhibitory activity of these compounds was analyzed using allopurinol as a positive control (IC50 7.49 ± 0.29 M). It was found that sesquiterpenes and flavonoids, containing 7-OMe group, are inactive. Conclusion: 7-Hydroxyflavones (apigenin and hispidulin) exerted significant XO inhibitory effect with IC50 values of 0.99 ± 0.33 M and 4.88 ± 1.21 M, respectively. Therefore, these compounds are responsible for the XO-inhibitory effect of the extract. The free radical scavenging activity of the isolated flavonoids was determined by DPPH assay, and it was stated that none of the compounds have substantial antioxidant activity, therefore the reduced generation of reactive oxygen species may be the consequence only of XO inhibition.

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