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Huperzine A: A Mini-Review of Biological Characteristics, Natural Sources, Synthetic Origins, and Future Prospects

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Abstract

Huperzia serrate is a known medicinal plant that produces the Lycopodium alkaloid Huperzine A (HupA). It has been used to treat such diseases as contusions, swellings, and pain since the year of 739. Chemical structure analyses show that HupA exists as two stereoisomers, (−)-HupA and (+)-HupA. The review was aimed to summarize the recent literature data about the biological characteristics, natural sources, synthetic origins, and future prospects in order to provide enhanced understanding of the properties of Huperzine A, and to supply a fundamental framework for the future studies of H. serrata.

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References

  1. Zhu, D., Wang, J., Zeng, Q., Zhang, Z., and Yan, R., J. Appl. Microbiol., 2010, vol. 109, no. 4, p. 1469. https://doi.org/10.1111/j.1365-2672.2010.04777.x

    Article  CAS  Google Scholar 

  2. Ma, X., Tan, C., Zhu, D., Gang, D. R., and Xiao, P., J. Ethnopharmacol., 2007, vol. 113, no. 1, p. 15. https://doi.org/10.1016/j.jep.2007.05.030

    Article  CAS  Google Scholar 

  3. Wang, R. and Tang, X.C., Neurosignals, 2005, vol. 14, nos. 1–2, p. 71. https://doi.org/10.1159/000085387

    Article  CAS  Google Scholar 

  4. Koshiba, T., Yokoshima, S., and Fukuyama, T., Org. Lett., 2009, vol. 11, no. 22, p. 5354. https://doi.org/10.1021/ol9022408

    Article  CAS  Google Scholar 

  5. Bialer, M., Johannessen, S.I., Levy, R.H., Perucca, E., Tomson, T., and White, H.S., Epilepsia, 2017, vol. 58, no. 2, p. 181. https://doi.org/10.1111/epi.13634

    Article  Google Scholar 

  6. Ferreira, A., Rodrigues, M., Fortuna, A., Falcão, A., and Alves, G., Phytochem. Rev., 2016, vol. 15, no. 1, p. 51. https://doi.org/10.1007/s11101-014-9384-y

    Article  CAS  Google Scholar 

  7. Yang, M., You, W., Wu, S., Fan, Z., Xu, B., Zhu, M., Li, X., and Xiao, Y., BMC Genomics, 2017, vol. 18, no. 1, p. 245. https://doi.org/10.1186/s12864-017-3615-8

    Article  Google Scholar 

  8. Ha, G.T., Wong, R.K., and Zhang, Y., Chem. Biodiversity, 2011, vol. 8, no. 7, p. 1189. https://doi.org/10.1002/cbdv.201000269

    Article  CAS  Google Scholar 

  9. Ding, R., Sun, B.F., and Lin, G.Q., Org. Lett., 2012, vol. 14, no. 17, p. 4446. https://doi.org/10.1021/ol301951r

    Article  CAS  Google Scholar 

  10. Schachter, S.C., Neurotherapeutics, 2009, vol. 6, no. 2, p. 415. https://doi.org/10.1016/j.nurt.2008.12.004

    Article  Google Scholar 

  11. Zhao, Y., Yue, P., Tao, T., and Chen, Q.H., Acta Pharmacol. Sin., 2007, vol. 28, no. 2, p. 273. https://doi.org/10.1111/j.1745-7254.2007.00486.x

    Article  CAS  Google Scholar 

  12. Wu, Q. and Gu, Y., J. Pharm. Biomed. Anal., 2006, vol. 40, no. 4, p. 993. https://doi.org/10.1016/j.jpba.2005.07.047

    Article  CAS  Google Scholar 

  13. Isoherranen, N., Woodhead, J.H., White, H.S., and Bialer, M., Epilepsia, 2001, vol. 42, no. 7, p. 831. https://doi.org/10.1046/j.1528-1157.2001.042007831.x

    Article  CAS  Google Scholar 

  14. Lim, W.H., Goodger, J.Q., Field, A.R., Holtum, J.A., and Woodrow, I.E., Pharm. Biol., 2010, vol. 48, no. 48, p. 1073. https://doi.org/10.3109/13880209.2010.485619

    Article  CAS  Google Scholar 

  15. Huang, J. and He, C., Biochem. Syst. Ecol., 2010, vol. 38, no. 6, p. 1137. https://doi.org/10.1016/j.bse.2010.12.020

    Article  CAS  Google Scholar 

  16. Wang, Y., Wei, Y., Oguntayo, S., Jensen, N., Doctor, B.P., and Nambiar, M.P., Neurochem. Res., 2011, vol. 36, no. 12, p. 2381. https://doi.org/10.1007/s11064-011-0564-5

    Article  CAS  Google Scholar 

  17. Campiani, G., Kozikowski, A.P., Wang, S., Ming, L., Nacci, V., Saxena, A., and Doctor, B.P., Bioorg. Med. Chem. Lett., 1998, vol. 8, no. 11, p. 1413. https://doi.org/10.1016/s0960-894x(98)00229-7

    Article  CAS  Google Scholar 

  18. Hayashi, Y., Yamada, T., Sato, M., Watanabe, S., Kwon, E., Iwasaki, K., and Umemiya, S., Org. Lett., 2019, vol. 21, no. 13, p. 5183. https://doi.org/10.1021/acs.orglett.9b01774

    Article  CAS  Google Scholar 

  19. Cui, B.D., Li, S.W., Zuo, J., Wu, Z.J., Zhang, X.M., and Yuan, W.C., Tetrahedron, 2014, vol. 70, no. 10, p. 1895. https://doi.org/10.1016/j.tet.2014.01.036

    Article  CAS  Google Scholar 

  20. Liu, C., Zhu, Q., Huang, K.W., and Lu, Y., Org. Lett., 2011, vol. 13, no. 10, p. 2638. https://doi.org/10.1021/ol200747x

    Article  CAS  Google Scholar 

  21. Bai, F., Xu, Y., Chen, J., Liu, Q., Gu, J., Wang, X., Ma, J., Li, H., Onuchic, J.N., and Jiang, H., Proc. Natl. Acad. Sci. U. S. A., 2013, vol. 110, no. 11, p. 4273. https://doi.org/10.1073/pnas.1301814110

    Article  CAS  Google Scholar 

  22. Tang, X.C., Kindel, G.H., Kozikowski, A.P., and Hanin, I., J. Ethnopharmacol., 1994, vol. 44, no. 3, p. 147. https://doi.org/10.1016/0378-8741(94)01182-6

    Article  CAS  Google Scholar 

  23. Oluwafemi, A.J., Okanla, E.O., Camps, P., Munoz-Torrerob, D., Mackey, Z. B., Chiang, P. K., Seville, S., and Wright, C. W., Nat. Prod. Commun., 2009, vol. 4, no. 2, p. 193. http://europepmc.org/abstract/MED/19370921

    CAS  PubMed  Google Scholar 

  24. Abu Sohel, S.M. and Opatz, T., ChemInform, 2015, vol. 46, no. 8. https://doi.org/10.1002/chin.201508330

  25. Tun, M.K.M., Wüstmann, D.J., and Herzon, S.B., Chem. Sci., 2011, vol. 2, no. 11, p. 2251. https://doi.org/10.1039/C1SC00455G

    Article  CAS  Google Scholar 

  26. Ward, J. and Caprio, V., Tetrahedron Lett., 2006, vol. 47, no. 4, p. 553. https://doi.org/10.1016/j.tetlet.2005.11.037

    Article  CAS  Google Scholar 

  27. Reddy, P.G., Varghese, B., and Baskaran, S., Org. Lett., 2003, vol. 5, no. 4, p. 583. https://doi.org/10.1021/o1027563v

    Article  CAS  Google Scholar 

  28. Fustero, S., Jiménez, D., Moscardó, J., Catalán, S., and del Pozo, C., Org. Lett., 2007, vol. 9, no. 25, p. 5283. https://doi.org/10.1021/ol702447y

    Article  CAS  Google Scholar 

  29. Shu, S., Zhao, X., Wang, W., Zhang, G., Cosoveanu, A., Ahn, Y., and Wang, M., World J. Microbiol. Biotechnol., 2014, vol. 30, no. 12, p. 3101. https://doi.org/10.1007/s11274-014-1737-6

    Article  CAS  Google Scholar 

  30. Zhou, Y., Liu, X., Li, K.G., Wang, Z.G., Geng, X., and Hu, S.P., J. Jishou Univ., 2009, vol. 30, no. 2, p. 90. http://en.cnki.com.cn/Article_en/CJFDTOTAL-JSDN200902026.htm

    CAS  Google Scholar 

  31. Xu, M., Heidmarsson, S., de Boer, H.J., Kool, A., and Olafsdottir, E.S., J. Ethnopharmacol., 2019, vol. 245, article no. 112130. https://doi.org/10.1016/j.jep.2019.112130

  32. Han, W.X., Song, T., Li, W.Z., Zhang, H., Shao, M.M., and Wu, Y.H., Hainan Med. J., 2015, vol. 26, no. 15, p. 2275. http://en.cnki.com.cn/Article_en/CJFDTotal-HAIN201515029.htm

    CAS  Google Scholar 

  33. Zhang, X., Wang, Z., Jan, S., Yang, Q., and Wang, M., Sci. Rep., 2017, vol. 7, no. 1, p. 2766. https://doi.org/10.1038/s41598-017-02834-6

    Article  Google Scholar 

  34. Ying, Y.M., Shan, W.G., and Zhan, Z.J., J. Nat. Prod., 2014, vol. 77, no. 9, p. 2054. https://doi.org/10.1021/np500412f

    Article  CAS  Google Scholar 

  35. Zhu, D., Wang, J., Zeng, Q., Zhang, Z., and Yan, R., J. Appl. Microbiol., 2010, vol. 109, no. 4, p. 1469. https://doi.org/10.1111/j.1365-2672.2010.04777.x

    Article  CAS  Google Scholar 

  36. Zafonte, R.D., Fregni, F., Bergin, M.J.G., Goldstein, R., Boudreau, N., Monge, I., Luz, M., Frazier, J., and Giacino, J.T., Brain Inj., 2019, p. 1. https://doi.org/10.1080/02699052.2019.1677941

  37. Xing, S.H., Zhu, C.X., Zhang, R., and An, L., J. Evidence-Based Complementary Altern. Med., 2014, vol. 2014, article ID 363985. https://doi.org/10.1155/2014/363985

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Funding

This work was financially supported by the grant from the National Natural Science Foundation of China (no. 31460021).

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Authors and Affiliations

  1. Key Laboratory of Protection and Utilization of Subtropic Plant Resources of Jiangxi Province, College of Life Science, Jiangxi Normal University, Nanchang, 330022, China

    H. L. Yang, Y. S. Ma, X. L. Wang & D. Zhu

  2. Jiangxi Key Laboratory of Functional Organic Molecules, Jiangxi Science and Technology Normal University, Nanchang, 330013, China

    D. Zhu

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  1. H. L. Yang
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  2. Y. S. Ma
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  4. D. Zhu
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Correspondence to D. Zhu.

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Yang, H.L., Ma, Y.S., Wang, X.L. et al. Huperzine A: A Mini-Review of Biological Characteristics, Natural Sources, Synthetic Origins, and Future Prospects. Russ J Org Chem 56, 148–157 (2020). https://doi.org/10.1134/S1070428020010236

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