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New Triterpenoid Saponin C-20 Epimers from the Alkaline-Degradation Products of Ginsenoside Re and Their Cytotoxic Activities

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Nine compounds, including two new triterpenoid saponin C-20 epimers (4 and 5) and seven known ginsenosides (1–3, 6–9), have been isolated and purified from the alkaline-degradation products of ginsenoside Re. Their structures were elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR and HR-ESI-MS. Among them, (20S,22E)-6-O-β-D-glucopyranosyl-dammar-22(23),24-diene-3β,6α,12β-triol (4) and (20R,22E)-6-O-β-D-glucopyranosyl-dammar-22(23),24-diene-3β,6α,12β-triol (5) were identified as new triterpenoid saponins and they were assayed for cytotoxic activities against five human tumor cell lines.

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References

  1. A. Mallol, R. M. Cusido, J. Palazon, M. Bonfill, C. Morales, and M. T. Pinol, Phytochemistry, 57, 365 (2001).

    Article  PubMed  CAS  Google Scholar 

  2. Z. Wang, M. Li, W. K. Wu, H. M. Tan, and D. F. Geng, Cardiovasc. Drugs Ther., 22, 443 (2008).

    Article  PubMed  CAS  Google Scholar 

  3. A. S. Attele, J. A. Wu, and C. S. Yuan, Biochem. Pharmacol., 58, 1685 (1999).

    Article  PubMed  CAS  Google Scholar 

  4. W. S. Sung and D. G. Lee, Biol. Pharm. Bull., 31, 1614 (2008).

    Article  PubMed  CAS  Google Scholar 

  5. D. H. Kim, J. S. Jung, Y. S. Moon, J. H. Sung, H. W. Suh, Y. H. Kim, and D. K. Song, Biol. Pharm. Bull., 26, 1035 (2003).

    Article  PubMed  CAS  Google Scholar 

  6. J. F. Cui, M. Garle, E. Lund, I. Bjorkhem, and P. Eneroth, Anal. Biochem., 210, 411 (1993).

    Article  PubMed  CAS  Google Scholar 

  7. S. R. Ko, K. J. Choi, K. Uchida, and Y. Suzuki, Planta Med., 69, 285 (2003).

    Article  PubMed  CAS  Google Scholar 

  8. Y. J. Chen, M. Nose, and Y. Ogihara, Chem. Pharm. Bull., 35, 1653 (1987).

    Article  PubMed  CAS  Google Scholar 

  9. W. C. S. Cho, W. S. Chung, S. K. W. Lee, A. W. N. Leung, C. H. K. Cheng, and K. K. M. Yue, Eur. J. Pharm., 550, 173 (2006).

    Article  CAS  Google Scholar 

  10. J. T. Xie, Z. H. Shao, T. L. V. Hoek, W. T. Chang, J. L. S. Mehendale, C. Z. Wang, C. W. Hsu, L. B. Becker, and J. J. Y, C. S. Yuan, Eur. J. Pharm., 532, 201 (2006).

  11. R. Teng, H. Li, J. Chen, D. Wang, D. Wang, Y. He, and C. Yang, Magn. Reson. Chem., 40, 483 (2002).

    Article  CAS  Google Scholar 

  12. I. P. Holland, A. McCluskey, J. A. Sakoff, J. Gilbert, N. Chau, P. J. Robinson, C. A. Motti, A. D. Wright, and I. A. Altena, J. Nat. Prod., 72, 102 (2009).

    Article  PubMed  CAS  Google Scholar 

  13. S. X. Xu, N. L. Wang, and Y. H. Li, Acta Pharm. Sin., 21, 356 (1986).

    CAS  Google Scholar 

  14. I. I. H. Park, N. Y. Kim, S. B. Han, J. M. Kim, S. W. Kwon, H. J. Kim, M. K. Park, and J. H. Park, Arch. Pharm. Res., 25, 428 (2002).

    Article  PubMed  CAS  Google Scholar 

  15. J. H. Ryu, J. H. Park, T. H. Kim, D. H. Sohn, J. M. Kim, and J. H. Park, Arch. Pharm. Res., 19, 335 (1996).

    Article  CAS  Google Scholar 

  16. J. H. Ryu, J. H. Park, J. H. Eun, J. H. Jung, and D. H. Sohn, Phytochemistry, 44, 931 (1997).

    Article  CAS  Google Scholar 

  17. J. Liao, J. Sun, Y. Niu, and B. Yu, Tetrahedron Lett., 52, 3075 (2011).

    Article  CAS  Google Scholar 

  18. T. Mosmann, J. Immunol. Methods, 65, 55 (1983).

    Article  PubMed  CAS  Google Scholar 

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Acknowledgment

The authors are grateful to the State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, University of Jilin at Changchun for access to the Bruker AVANCE-500 NMR instrument for this study. The other chemical analysis was provided by the Alan. G. MacDiarmid Laboratory of Jilin University.

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Correspondence to Yanping Chen.

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Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2018, pp. 416–419.

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Ding, H., Wang, Z., Chen, X. et al. New Triterpenoid Saponin C-20 Epimers from the Alkaline-Degradation Products of Ginsenoside Re and Their Cytotoxic Activities. Chem Nat Compd 54, 490–495 (2018). https://doi.org/10.1007/s10600-018-2386-z

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  • DOI: https://doi.org/10.1007/s10600-018-2386-z

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