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Reaction of Paeoniflorin with Lower Alcohols in the Presence of Cation Exchanger

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Chemistry of Natural Compounds Aims and scope

The reaction of paeoniflorin (PF) with refluxing MeOH in the presence of cation exchanger KU-2-8 (H+) formed a mixture of the 4-O-methyl- and 4-oxo-9-O-methyl ethers (1:1, overall yield 90%) that were separated by chromatography over silica gel. The reaction of PF with EtOH and BuOH under analogous conditions also formed mixtures of the ethyl and butyl ethers from which 4-oxo-9-O-ethyl(butyl) ethers were isolated as the tetra-O-acetates. The structures of the obtained compounds were confirmed using PMR and 13C NMR spectra.

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References

  1. H.-C. Lin, H.-Y. Ding, T.-S. Wu, and P.-L. Wu, Phytochemistry, 41, 237 (1996).

    Article  CAS  Google Scholar 

  2. J. W. Duan, J. Y. Yang, L. X. Chen, L. J. Zhang, Z. H. Jiang, X. D. Cai, X. Zhang, and F. Qiu, J. Nat. Prod., 72, 1579 (2009).

    Article  CAS  PubMed  Google Scholar 

  3. P. Li, Z.-M. Zhang, T. Li, Y.-B. Zhang, S. C. Wing, G.-C. Wang, Y.-L. Li, and W.-C. Ye, Fitoterapia, 98, 124 (2014).

    Article  CAS  PubMed  Google Scholar 

  4. Y.-H. Shi, S. Zhu, Y.-W. Ge, Y.-M. He, K. Kazuma, Z. Wang, K. Yoshimatsu, and K. Komatsu, Fitoterapia, 108, 55 (2016).

    Article  CAS  PubMed  Google Scholar 

  5. H. L. Ko, E. H. Jung, D. H. Jung, J. K. Kim, S. K. Ku, Y. W. Kim, S. C. Kim, R. Zhao, C. W. Lee, and I. J. Cho, J. Funct. Foods, 20, 303 (2016).

    Article  CAS  Google Scholar 

  6. S. A. Osadchii, E. I. Chernyak, M. M. Shakirov, E. E. Shul’ts, and G. A. Tolstikov, Khim. Interesakh Ustoich. Razvit., 8, 399 (2000).

    Google Scholar 

  7. H. O. Yang, W. K. Ko, J. Y. Kim, and H. S. Ro, Fitoterapia, 75, 45 (2004).

    Article  CAS  PubMed  Google Scholar 

  8. J. Sun, J. Wu, Ch. Xu, Q. Luo, B. Li, and J. Dong, Int. Immunopharmacol., 24, 88 (2015).

  9. M. Chen, L. Cao, Y. Luo, X. Feng, L. Sun, M. Wen, and S. Peng, Int. Immunopharmacol., 24, 42 (2015).

    Article  CAS  PubMed  Google Scholar 

  10. Q. Zhang, Y. Yuan, J. Cui, T. Xiao, and D. Jiang, Biomed. Pharmacother., 78, 197 (2016).

    Article  CAS  PubMed  Google Scholar 

  11. H. Liu, J. Wang, J. Wang, P. Wang, and Y. Xue, Brain Res., 1618, 149 (2015).

    Article  CAS  PubMed  Google Scholar 

  12. S.-Z. Zhong, Q.-H. Ge, Q. Li, R. Qu, and S.-P. Ma, J. Neurol. Sci., 280, 71 (2009).

    Article  CAS  PubMed  Google Scholar 

  13. N. Aimi, M. Inaba, M. Watanabe, and S. Shibata, Tetrahedron, 25, 1825 (1969).

    Article  CAS  PubMed  Google Scholar 

  14. L. A. Baltina, Jr., R. M. Kondratenko, L. V. Spirikhin, and L. A. Baltina, Chem. Nat. Compd., 52, 347 (2016).

    Article  CAS  Google Scholar 

  15. A. J. Gordon and R. A. Ford, The Chemists Companion, Wiley-Interscience, New York, 1972.

    Google Scholar 

Download references

Acknowledgment

The work was supported financially by the RFBR (Grant 15-03-03101a).

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Correspondence to L. A. Baltina.

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Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2017, pp. 754–757.

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Baltina, L.A., Shabieva, E.R., Kondratenko, R.M. et al. Reaction of Paeoniflorin with Lower Alcohols in the Presence of Cation Exchanger. Chem Nat Compd 53, 887–890 (2017). https://doi.org/10.1007/s10600-017-2148-3

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  • DOI: https://doi.org/10.1007/s10600-017-2148-3

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