Regioselective synthesis of quercetin and myricetin derivatives

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Abstract

A regioselective method for the synthesis of esters of quercetin and myricetin at the hydroxy group in the 3 position was developed. As acids participating in the esterification reaction, 2-hydroxybenzoic (salicylic), 4-hydroxybenzoic, 2,6-dihydroxybenzoic, 3,4-dihydroxybenzoic (procatechuic), 3,4,5-trihydroxybenzoic (gallic) acids were used. A new series of quercetin and myricetin esters were obtained.

About the authors

S. V Pechinskii

Medical Pharmaceutical Institute, Pyatigorsk Branch of Volgograd Medical State University

Email: hplc@yandex.ru

A. G Kuregyan

Medical Pharmaceutical Institute, Pyatigorsk Branch of Volgograd Medical State University

E. T Oganesyan

Medical Pharmaceutical Institute, Pyatigorsk Branch of Volgograd Medical State University

References

  1. https://pubmed.ncbi.nlm.nih.gov/?term=flavonoids&sort=pubdate&timeline=expanded.
  2. Tungmunnithum D., Thongboonyou A., Pholboon A., Yangsabai A. // Medicine. 2018. Vol. 5. N 3. P. 93. doi: 10.3390/medicines5030093
  3. Kumar S., Pandey A.K. // Sci. World J. 2013. Article ID 162750. doi: 10.1155/2013/162750
  4. Panche A., Diwan A., Chandra S. // J. Nutr. Sci. 2016. Vol. 5. P. e47. doi: 10.1017/jns.2016.41
  5. Ullah A., Munir S., Badshah S.L., Khan N., Ghani L., Poulson B.G., Emwas A.-H., Jaremko M. // Molecules. Vol. 25. N 22. P. 5243. doi: 10.3390/molecules25225243
  6. Hosseini A., Razavi B.M., Banach M., Hosseinzadeh H. // Phytother. Res. 2021. P. 5352. doi: 10.1002/ptr.7144
  7. Zhao J., Tian S., Lu D., Yang J., Zeng H., Zhang F., Tu D., Ge G., Zheng Y., Shi T., Xu X., Zhao S., Yang Y., Zhang W. // Phytomedicine. 2021. Vol. 85. P. 153315. doi: 10.1016/j.phymed.2020.153315
  8. Bimonte S., Albino V., Piccirillo M., Nasto A., Molino C., Palaia R. Cascella M. // Drug Design, Development and Therapy. 2019. Vol. 13 P. 611. doi: 10.2147/DDDT.S180079
  9. Bimonte S., Cascella М. // Drug Design, Development and Therapy. 2020. Vol. 14. Р. 4245. doi: 10.2147/dddt.s253092
  10. Zhang Y.Q., Li K., Guo Q., Li D. // Front Genet. 2022. Vol. 13. 890079. doi: 10.3389/fgene.2022.890079
  11. Wigner P, Bijak M, Saluk-Bijak J. // Int. J. Mol. Sci. 2021. Vol. 22. N 15. Р. 7787. doi: 10.3390/ijms22157787
  12. Javed Z., Khan K., Herrera-Bravo J., Naeem S., Iqbal M.J., Raza Q., Sadia H., Raza S., Bhinder M., Calina D., Sharifi-Rad J., Cho W.C. // Cancer Cell Int. 2022. Vol. 22. N 1. P. 239. doi: 10.1186/s12935-022-02663-2
  13. Park, R., Jang, M., Park, Y.-I., Park, Y., Jung,W., Park, J., Park, J. // Viruses. 2021. Vol. 13. Р. 2533. doi.org/10.3390/v13122533
  14. Henss L., Auste A., Schürmann C., Schmidt C., von Rhein C., Mühlebach M.D., Schnierle B.S. // J. Gen. Virology. 2021. Vol. 102. 001574. doi: 10.1099/jgv.0.001574
  15. Печинский С.В., Оганесян Э.Т. Курегян А.Г. // Фармацевтическое дело и технология лекарств. 2021. № 1. С. 22. doi: 10.33920/med-13-2101-02
  16. Sharifi-Rad M., Pezzani R., Redaelli M., Zorzan M., Imran M., Ahmed Khalil A., Salehi B., Sharopov F., Cho W.C., Sharifi-Rad J. // Molecules. 2020. Vol. 25. N 3. P. 467. doi: 10.3390/molecules25030467.
  17. Roy A., Khan A., Ahmad I., Alghamdi S., Rajab B.S., Babalghith A.O., Alshahrani M.Y., Islam S., Islam M.R. // Biomed. Res. Int. 2022. doi: 10.1155/2022/5445291
  18. Li G., Zeng X., Xie J., Zhenzhen C., Moore J.C., Yuan X., Cheng Z., Ji G. // Fitoterapia. 2012. Vol. 83. N 1. P. 182. doi: 10.1016/j.fitote.2011.10.012
  19. Tang D., Chen K., Huang L., Li J. // Expert Opinion on Drug Metabolism & Toxicology. 2017. Vol. 13. P. 323. doi: 10.1080/17425255.2017.1251903
  20. Huang T., Liu Y., Zhang C. // Eur. J. Drug Metabolism and Pharmacokinetics. 2019. Vol. 44. P.159. doi: 10.1007/s13318-018-0509-3
  21. Park K.-S., Kim H., Kim M.K., Kim K., Chong Y. // J. Korean Soc. Appl. Biol. Chem. 2015. Vol. 58. N 3. P. 317. doi: 10.1007/s13765-015-0049-3
  22. Zhang W.L., Chen J.-P., Lam K.Y.-C., Zhan J.Y.-X., Yao P., Dong T.T.-X., Tsim K.W.-K. // Evidence-Based Complementary and Alternative Medicine. 2014. Vol. 2014. Article ID 608721. doi: 10.1155/2014/608721
  23. Pietta P.-G. // J. Nat. Prod. 2000. Vol. 63. N 7. P. 1035. doi: 10.1021/np9904509
  24. Santos C.M.M., Silva A.M.S. // Molecules. 2020. Vol. 25. N 3. P. 696. doi: 10.3390/molecules25030696
  25. Li W., Wu H., Liu B., Hou X., Wan D., Lou W., Zhao J. // J. Biotechnol. 2015. Vol. 199. P. 31. doi: 10.1016/j.jbiotec.2015.02.012
  26. Liu B., Li W., Nguyen T.A., Zhao J. // Food Chem. 2012. Vol. 134. N 2. P. 926. doi: 10.1016/j.foodchem.2012.02.207
  27. Van Acker S.A.B.E., Van Den Berg D.-j., Tromp M.N.J.L., Griffioen D.H., Van Bennekom V.P., Van Der Vijgh W.J.F., Bast A. // Free Radical Biology and Medicine. 1996. Vol. 20. N 3. P. 331. doi: 10.1016/0891-5849(95)02047-0
  28. Sardone L., Pignataro B., Castelli F., Sarpietro M.G., Nicolosi G., Marletta G. // J. Colloid Interface Sci. 2004. Vol. 271. N 2. P. 329. doi: 10.1016/j.jcis.2003.11.037
  29. de Araújo M.E., Franco Y.E., Messias M.C., Longato G.B., Pamphile J.A., Carvalho P.O. // Planta Med. 2017. Vol. 83. P. 7. doi: 10.1055/s-0042-118883
  30. Park K.D., Cho S.J. // Eur. J. Med. Chem. 2010. Vol. 45. N 3. P.1028. doi: 10.1016/j.ejmech.2009.11.045
  31. Kim M.K., Park K.-S., Lee C., Park H.R., Choo H., Chong Y. // J. Med. Chem. 2010. Vol. 53. N 24. P. 8597. doi: 10.1021/jm101252m
  32. Cho S.Y., Kim M.K., Park K.S., Choo H., Chong Y. // Bioorg. Med. Chem. 2013. Vol. 21. N 7. P. 1671. doi: 10.1016/j.bmc.2013.01.057.
  33. PASS online. http://way2drug.com/passonline
  34. Pat. US 3661890 (1972).

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