Skip to main content
Log in

Newly Synthesized N-Glycosidic Halochalcones Reveal Inhibitory Activity on Pancreatic Triacylglycerol Lipase

  • Published:
Chemistry of Natural Compounds Aims and scope

In this study, the aim was to synthesize N-glycosidic halochalcone derivatives and to examine their lipase inhibitory activity. The synthesized chalcones (1–3) were well known and the data were compatible with previous findings. However, compounds 4a/b, 5a/b, 6a/b, and 7–9 were synthesized for the first time in the current study. Remarkable lipase inhibitory potentials of the synthesized compounds were further confirmed through molecular docking studies. The highest lipase inhibition activity was experimentally identified for compounds 2 and 5a with IC50 17.7133 ± 0.9648 μg/mL and IC50 22.6521 ± 1.2146 μg/mL, respectively.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.
Fig. 2.

Similar content being viewed by others

References

  1. A. Hruby and F. B. Hu, Pharmacoeconomics, 33, 673 (2015).

    Article  PubMed  PubMed Central  Google Scholar 

  2. M. A. McArdle, O. M. Finucane, R. M. Connaughton, A. M McMorrow, and H. M Roche, Front. Endocrinol., 4, 52 (2013).

    Article  Google Scholar 

  3. WHO. Obesity and Overweight [Internet]. Word Health Organization, 2021, [cited 2021, Oct. 11]. Available from https://www.who.int/news-room/fact-sheets/detail/obesity-and-overweight.

  4. J. G. Kang and C. Y. Park, Diabetes Metab. J., 36, 13 (2012).

    Article  PubMed  PubMed Central  Google Scholar 

  5. X. Qi, IOP Conf. Ser.: Mater. Sci. Eng., 301, 012063 (2018).

    Google Scholar 

  6. T. T. Liu, X. T. Liu, Q. X. Chen, and Y. Shi, Biomed. Pharmacother., 128, 110314 (2020).

    Article  CAS  PubMed  Google Scholar 

  7. P. Ercan and S. Nehir, Akademik Gida Derg., 12, 69 (2014).

    Google Scholar 

  8. M. J. Climent, A. Corma, S. Iborra, and A. Velty, J. Catal., 221, 474 (2004).

    Article  CAS  Google Scholar 

  9. J. T. Li, W. Z. Yang, S. X. Wang, S. H. Li, and T. S. Li, Ultrason Sonochem., 9, 237 (2002).

    Article  CAS  PubMed  Google Scholar 

  10. N. Erdemoglu and B. Sener, Ankara Ecz. Fak. Derg., 28, 99 (1999).

    Article  CAS  Google Scholar 

  11. S. N. Mokale, P. N. Dube, S. A. Bhavale, I. Sayed, A. Begum, M. C. Nevase, V. R. Shelke, and A. Mujaheed, Med. Chem. Res., 24, 1842 (2015).

    Article  CAS  Google Scholar 

  12. T. L. B. Ventura, S. D. Calixto, B. A. Abrahim-Vieira, A. M. T. Souza, M. V. P. Mello, C. R. Rodrigues, and M. L. S. Mariz, Molecules, 20, 8072 (2015).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. M. Satyanarayana, P. Tiwari, B. K. Tripathi, A. K. Srivastava, and R. Pratap, Bioorg. Med. Chem., 12, 883 (2004).

    Article  CAS  PubMed  Google Scholar 

  14. J. H. Wu, X. H. Wang, Y. H. Yi, and K. H. Lee, Bioorg. Med. Chem. Lett., 13, 1813 (2003).

    Article  CAS  PubMed  Google Scholar 

  15. K. L. Lahtchev, D. I. Batovska, S. P. Parushev, V. M. Ubiyvovk, and A. A. Sibirny, Eur. J. Med. Chem., 43, 2220 (2008).

    Article  CAS  PubMed  Google Scholar 

  16. Y. M. Lin, Y. Zhou, M. T. Flavin, L. M. Zhou, W. Nie, and F. C. Chen, Bioorg. Med. Chem., 10, 2795 (2002).

    Article  CAS  PubMed  Google Scholar 

  17. C. Zhuang, W. Zhang, C. Sheng, W. Zhang, C. Xing, and Z. Miao, Chem. Rev., 117, 7762 (2017).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. M. B. Santos, V. C. Pinhanelli, M. A. R. Garcia, G. Silva, S. J. Baek, S. C. Franca, A. L. Fachin, M. Marins, and L. O. Regasini, Eur. J. Med. Chem., 138, 884 (2017).

    Article  CAS  PubMed  Google Scholar 

  19. R. S. Varma and R. Saini, Synlett, 7, 857 (1997).

    Article  Google Scholar 

  20. M. Parker, P. Osidacz, G. Baldock, Y. Hayasaka, C. Black, K. Pardon, D. Jeffery, J. Geue, M. Herderich, and L. Francis, J. Agric. Food Chem., 60, 2629 (2012).

    Article  CAS  PubMed  Google Scholar 

  21. Y. Bustanji, I. M. Al-Masri, M. Mohammad, M. Hudaib, K. Tawaha, H. Tarazi, and H. S. Alkhatib, J. Enzyme Inhib. Med. Chem., 26, 453 (2011).

    Article  CAS  PubMed  Google Scholar 

  22. S. O. Sener, U. Ozgen, S. Kanbolat, N. Korkmaz, M. Badem, H. Hanci, T. Dirmenci, T. Arabaci, R. Aliyazicioglu, E. Yenilmez, and G. S. Iscan, S. Afr. J. Bot., 141, 243 (2021).

    CAS  Google Scholar 

  23. M. H. M. Olsson, C. R. Sondergaard, M. Rostkowski, and J. H. Jensen, J. Chem. Theory Comput., 7, 525 (2011).

    Article  CAS  PubMed  Google Scholar 

  24. C. R. Sondergaard, M. H. M. Olsson, M. Rostkowski, and J. H. Jensen, J. Chem. Theory Comput., 7, 2284 (2011).

    Article  CAS  PubMed  Google Scholar 

  25. N. M. O′Boyle, M. Banck, C. A. James, C. Morley, T. Vandermeersch, and G. R. Hutchison, J. Cheminform., 3, 33 (2011).

  26. O. Trott and A. J. Olson, J. Comput. Chem., 31, 455 (2010).

    CAS  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgment

For funding we acknowledge Karadeniz Technical University Scientific Research Projects Unit (Project No. TYL-2021-9443).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to R. Aliyazicioglu.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2023, pp. 530–536.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yikilmaz, M., Fandakli, S., Sener, S.O. et al. Newly Synthesized N-Glycosidic Halochalcones Reveal Inhibitory Activity on Pancreatic Triacylglycerol Lipase. Chem Nat Compd 59, 629–637 (2023). https://doi.org/10.1007/s10600-023-04075-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-023-04075-8

Keywords

Navigation