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.
Similar content being viewed by others
References
A. Hruby and F. B. Hu, Pharmacoeconomics, 33, 673 (2015).
M. A. McArdle, O. M. Finucane, R. M. Connaughton, A. M McMorrow, and H. M Roche, Front. Endocrinol., 4, 52 (2013).
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.
J. G. Kang and C. Y. Park, Diabetes Metab. J., 36, 13 (2012).
X. Qi, IOP Conf. Ser.: Mater. Sci. Eng., 301, 012063 (2018).
T. T. Liu, X. T. Liu, Q. X. Chen, and Y. Shi, Biomed. Pharmacother., 128, 110314 (2020).
P. Ercan and S. Nehir, Akademik Gida Derg., 12, 69 (2014).
M. J. Climent, A. Corma, S. Iborra, and A. Velty, J. Catal., 221, 474 (2004).
J. T. Li, W. Z. Yang, S. X. Wang, S. H. Li, and T. S. Li, Ultrason Sonochem., 9, 237 (2002).
N. Erdemoglu and B. Sener, Ankara Ecz. Fak. Derg., 28, 99 (1999).
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).
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).
M. Satyanarayana, P. Tiwari, B. K. Tripathi, A. K. Srivastava, and R. Pratap, Bioorg. Med. Chem., 12, 883 (2004).
J. H. Wu, X. H. Wang, Y. H. Yi, and K. H. Lee, Bioorg. Med. Chem. Lett., 13, 1813 (2003).
K. L. Lahtchev, D. I. Batovska, S. P. Parushev, V. M. Ubiyvovk, and A. A. Sibirny, Eur. J. Med. Chem., 43, 2220 (2008).
Y. M. Lin, Y. Zhou, M. T. Flavin, L. M. Zhou, W. Nie, and F. C. Chen, Bioorg. Med. Chem., 10, 2795 (2002).
C. Zhuang, W. Zhang, C. Sheng, W. Zhang, C. Xing, and Z. Miao, Chem. Rev., 117, 7762 (2017).
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).
R. S. Varma and R. Saini, Synlett, 7, 857 (1997).
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).
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).
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).
M. H. M. Olsson, C. R. Sondergaard, M. Rostkowski, and J. H. Jensen, J. Chem. Theory Comput., 7, 525 (2011).
C. R. Sondergaard, M. H. M. Olsson, M. Rostkowski, and J. H. Jensen, J. Chem. Theory Comput., 7, 2284 (2011).
N. M. O′Boyle, M. Banck, C. A. James, C. Morley, T. Vandermeersch, and G. R. Hutchison, J. Cheminform., 3, 33 (2011).
O. Trott and A. J. Olson, J. Comput. Chem., 31, 455 (2010).
Acknowledgment
For funding we acknowledge Karadeniz Technical University Scientific Research Projects Unit (Project No. TYL-2021-9443).
Author information
Authors and Affiliations
Corresponding author
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.
About this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-023-04075-8