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Synthesis of Polymethoxyflavonoids from Hesperidin and Naringin and their Antiproliferative Activity

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Chemistry of Heterocyclic Compounds Aims and scope

A series of polymethoxyflavonoids were synthesized via cleavage of the glycosidic bond, dehydrogenation, selective methylation, bromination, nucleophilic aromatic substitution, O-prenylation, Claisen–Schmidt aldol condensation, cyclization, and oxidation from very abundant and inexpensive natural flavonoids hesperidin and naringin. The in vitro antiproliferative activity of the synthesized compounds was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2, and SUN-5) by the CellTiter-Glo assay. The results showed that some of synthesized compounds exhibited moderate to high antiproliferative activity. Among them, (2E)-1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(7-methoxy-1,3-benzodioxol-5-yl)prop-2-en-1-one was revealed to be the most active with IC50 values ranging from 10.35 to 13.89 μM against all four cancer cell lines, the IC50 value (10.35 μM) being below positive control cisplatin (12.36 μM) against HepG-2 cells.

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References

  1. Asakawa, T.; Sagara, H.; Kanakogi, M.; Hiza, A.; Tsukaguchi, Y.; Ogawa, T.; Nakayama, M.; Ouchi, H.; Inai, M.; Kan, T. Org. Process Res. Dev. 2019, 23, 595.

    Article  CAS  Google Scholar 

  2. Raffa, D.; Maggio, B.; Raimondi, M. V.; Plescia, F.; Daidone, G. Eur. J. Med. Chem. 2017, 142, 213.

    Article  CAS  Google Scholar 

  3. Wang, M. Y.; Meng, D.; Zhang, P.; Wang, X.; Du, G.; Brennan, C.; Li, S. M.; Ho, C.-T.; Zhao, H. J. Agric. Food Chem. 2018, 66, 3155.

    Article  CAS  Google Scholar 

  4. Li, S.; Pan, M.-H.; Lai, C.-S.; Lo, C.-Y.; Dushenkov, S.; Ho, C.-T. Bioorg. Med. Chem. 2007, 15, 3381.

    Article  CAS  Google Scholar 

  5. Manthey, J. A.; Guthrie, N. J. Agric. Food Chem. 2002, 50, 5837.

    Article  CAS  Google Scholar 

  6. Yuan, J.; Wong, I. L. K.; Jiang, T.; Wang, S. W.; Liu, T.; Wen, B. J.; Chow, L. M. C.; Sheng, B. W. Eur. J. Med. Chem. 2012, 54, 413.

    Article  CAS  Google Scholar 

  7. Nguyen, V.-S.; Li, W.; Li, Y.; Wang, Q. A. Med. Chem. Res. 2017, 26, 1585.

    Article  CAS  Google Scholar 

  8. Vongdeth, K.; Han, P.; Li, W.; Wang, Q.-A. Chem. Nat. Compd. 2019, 55, 11.

    Article  CAS  Google Scholar 

  9. Li, S.; Lo, C.-Y.; Ho, C.-T. J. Agric. Food Chem. 2006, 54, 4176.

    Article  CAS  Google Scholar 

  10. Hirata, T.; Fujii, M.; Akita, K.; Yanaka, N.; Ogawa, K.; Kuroyanagi, M.; Hongo, D. Bioorg. Med. Chem. 2009, 17, 25.

    Article  CAS  Google Scholar 

  11. Chung, L. Y.; Yap, K. F.; Goh, S. H.; Mustafa, M. R.; Imiyabir, Z. Phytochemistry 2008, 69, 1548.

    Article  CAS  Google Scholar 

  12. Buisson, D.; Quintin, J.; Lewin, G. J. Nat. Prod. 2007, 70, 1035.

    Article  CAS  Google Scholar 

  13. Yan, L.; Liu, H.; Wang, Q.; Wang, G. Chem. Heterocycl. Compd. 2017, 53, 871.

    Article  CAS  Google Scholar 

  14. Li, M.; Xu, Y.; Zuo, M.; Liu, W.; Wang, L.; Zhu, W. J. Nat. Prod. 2019, 82, 2279.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Advanced Catalytic Engineering Research Center of the Ministry of Education, Hunan University, Changsha, 410082, P. R. China

    Liang Su, Zhizhong Jin, Kexiong Liu & Qiuan Wang

Authors
  1. Liang Su
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  2. Zhizhong Jin
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  3. Kexiong Liu
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  4. Qiuan Wang
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Corresponding author

Correspondence to Qiuan Wang.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(2/3), 100–105

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Su, L., Jin, Z., Liu, K. et al. Synthesis of Polymethoxyflavonoids from Hesperidin and Naringin and their Antiproliferative Activity. Chem Heterocycl Comp 58, 100–105 (2022). https://doi.org/10.1007/s10593-022-03062-1

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  • DOI: https://doi.org/10.1007/s10593-022-03062-1

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