Planta Med 2022; 88(15): 1514
DOI: 10.1055/s-0042-1759193
Poster Session II

6-Gingerol Derivatives as Promising Antiplatelet Leads

Authors

  • SHH Ahmed∗

    1   Institute of Pharmacognosy, University of Szeged, H-6720, Szeged, Hungary

  • T Gonda

    1   Institute of Pharmacognosy, University of Szeged, H-6720, Szeged, Hungary

  • O Agbadua

    1   Institute of Pharmacognosy, University of Szeged, H-6720, Szeged, Hungary

  • G Girst

    1   Institute of Pharmacognosy, University of Szeged, H-6720, Szeged, Hungary

  • R Berkecz

    2   Institute of Pharmaceutical Analysis, University of Szeged, 4, 6720, Szeged, Hungary

  • N Kúsz

    1   Institute of Pharmacognosy, University of Szeged, H-6720, Szeged, Hungary

  • M-C Tsai

    3   Graduate Institute of Natural Products, Kaohsiung Medical University, 807, Kaohsiung, Taiwan

  • C-C Wu

    3   Graduate Institute of Natural Products, Kaohsiung Medical University, 807, Kaohsiung, Taiwan

  • G T Balogh

    4   Institute of Pharmacodynamics and Biopharmacy, University of Szeged, H-6720, Szeged, Hungary
    5   Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, H-1111, Budapest, Hungary

  • A Hunyadi

    1   Institute of Pharmacognosy, University of Szeged, H-6720, Szeged, Hungary
    6   Interdisciplinary Centre of Natural Products, University of Szeged, H-6720, Szeged, Hungary
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Ginger (Zingiber officinale, Roscoe) is a widely used spice since ancient times, and there are many reports about its rootsʼ constituents, mainly gingerols and shogaols, for their beneficial bioactivities in health and disease [1], [2]. In this context, gingerols were reported to have promising antiplatelet activity [3].

In this work, 6-gingerolʼs structure was used as a core for the synthesis of derivatives ([Fig. 1]) that were tested for their inhibitory activity against AA-induced platelet aggregation and COX-1, and for their antioxidant activity. In silico ADME and docking studies were also performed. Ligand lipophilic efficiency (LLE) was used as a scoring function towards the best lead. The natural compound 3 showed the most promising antiplatelet activity with an IC50 of 2.1 µM, while a semisynthetic new compound 17 had an IC50 value of 3.1 µM. These results were supported by COX-1 IC50 values of 4.36 and 5.84 µM for compounds 3 and 17, respectively. Further, the lowest in silico binding affinity, i.e., − 9.5 kcal/mol was calculated for compound 17. The LLE results, however, pointed out compound 11 as our best lead for further development.

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Fig. 1 6-Gingerol and its synthesized derivatives.

The authors declare no conflict of interest.

Acknowledgements

NKFIH K-134704




Publication History

Article published online:
12 December 2022

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Zoom
Fig. 1 6-Gingerol and its synthesized derivatives.