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Characterization and antinociceptive activity (in vivo) of kempferol-3,4′-di-O-α-L-rhamnopyranoside isolated from Dryopteris cycadina

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Abstract

Compound 1, isolated from Dryopteris cycadina, was characterized as kempferol-3,4′-di-O-α-L-rhamnopyranoside on the basis of 1H and 13C NMR spectroscopic techniques. On the basis of preliminary screening data for this compound, its antinociceptive activity in different animal models was evaluated. Compound 1 displayed dose-dependent antinociceptive effects with maximum activity of 46.12 % at 10 mg/kg i.p. against acetic acid-induced writhing. In addition, it also showed dose-dependent blockade of noxious stimulation in both phases of formalin test with 40.78 and 43.44 % in the first and second phases at 10 mg/kg i.p., respectively. However, the injection of naloxone did not block the antinociceptive effect of compound 1 and thus ruled out the opioidergic involvement. It is, therefore, concluded with confidence that compound 1, isolated from D. cycadina, provoked strong antinociceptive activity and could be a lead analgesic drug candidate. Moreover, the mechanism of antinociceptive action by different flavonoids has also been investigated; results revealed that the bioactivity of compound 1 analogs should be discussed not only on the basis of flavonoids/biotarget interaction, but also on the basis of the catalytic activity of their bimetallic complexes.

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Acknowledgments

The authors are grateful for the financial support by the Higher Education Commission of Pakistan to complete this study. Professor T. Ben Hadda would like to thank ACTELION, the Biopharmaceutical Company of Swiss, for the molecular properties calculations.

Conflict of interest

The authors declared that we have no conflict of interest.

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Authors and Affiliations

  1. Department of Chemistry, University of Malakand, Malakand, 18800, Pakistan

    Mumtaz Ali, Sher Ali Khan & Manzoor Ahmad

  2. Institute of Chemical Sciences, University of Peshawar, Peshawar, 25120, Pakistan

    Abdur Rauf

  3. Department of Pharmacy, Abdul Wali Khan University Mardan, Mardan, 23200, Pakistan

    Haroon Khan

  4. HEJ Research Institute of Chemistry, University of Karachi, Karachi, 75270, Pakistan

    Mohammad Raza Shah

  5. Department of Chemistry, The University of Jordan, Amman, 11942, Jordan

    Mohammad S. Mubarak

  6. Laboratoire de Chimie Matériaux, FSO, Université Mohammed Ier, 60000, Oujda, Morocco

    Taibi Ben Hadda

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  1. Mumtaz Ali
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  2. Sher Ali Khan
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  3. Abdur Rauf
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  4. Haroon Khan
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Correspondence to Abdur Rauf, Mohammad S. Mubarak or Taibi Ben Hadda.

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Ali, M., Khan, S.A., Rauf, A. et al. Characterization and antinociceptive activity (in vivo) of kempferol-3,4′-di-O-α-L-rhamnopyranoside isolated from Dryopteris cycadina . Med Chem Res 24, 3218–3229 (2015). https://doi.org/10.1007/s00044-015-1373-1

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  • DOI: https://doi.org/10.1007/s00044-015-1373-1

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