Advertisement

Chemistry of Natural Compounds

, Volume 51, Issue 2, pp 311–315 | Cite as

A New Megastigmane Alkaloid from Pachysandra terminalis with Antitumor Metastasis Effect

  • Mei-Na Jin
  • Sheng-Nan Ma
  • Hui-Yuan Zhai
  • Nan-Qin
  • Hong-Quan Duan
  • De-Xin Kong
Article

9-(N,N-Dimethyl)-4,7-megastigmedien-3-one (1) was isolated from Pachysandra terminalis and identified by 1D and 2D NMR spectroscopic and mass spectrometric methods. Compound 1 revealed significant anti-metastasis effect on cancer cell migration and invasion through suppressing the expressions of p-PKCζ and p-integrin β1 in human breast cancer cells, and also showed anti-angiogenic activity on human umbilical vein endothelial cells.

Keywords

megastigmane alkaloid antitumor metastasis p-PKCζ p-integrin βanti-angiogenic activity 

Notes

Acknowledgment

This work was supported by grants from the National Natural Science Foundation of China (NSFC) (81072540) and the Tianjin Research Program of Applied Basic and Cutting-edge Technologies (11JCZDJC20900, 12JCZDJC25800).

References

  1. 1.
    D. R. Wan, W. J. Chen, Z. Qian, and Y. S. Lei, China. J. Chin. Mater. Med., 18, 581 (1993).Google Scholar
  2. 2.
    V. V. Kul’kova, R. Shakirov, and A. L. D’yakonov, Chem. Nat. Compd., 35, 107 (1999).CrossRefGoogle Scholar
  3. 3.
    Y. Sun, Y. X. Yan, J. C. Chen, L. Lu, X. M. Zhang, Y. Li, and M. H. Qiu, Steroids, 75, 818 (2010).CrossRefPubMedGoogle Scholar
  4. 4.
    M. I. Choudhary, K. P. Devkota, S. A. Nawaz, R. Ranjit, and Atta-ur-Rahman, Steroids, 70, 295 (2005).CrossRefPubMedGoogle Scholar
  5. 5.
    L. C. Chang, K. P. L. Bhat, E. J. Kennelly, H. H. S. Fong, J. M. Pezzuto, and A. D. Kinghorn, J. Nat. Prod., 61, 1257 (1998).CrossRefPubMedGoogle Scholar
  6. 6.
    H. Y. Zhai, C. Zhao, N. Zhang, M. N. Jin, S. A. Tang, N. Qin, and H. Q. Duan, J. Nat. Prod., 75, 1305 (2012).CrossRefPubMedGoogle Scholar
  7. 7.
    H. Q. Duan, H. Y. Zhai, S. A. Tang, M. N. Jin, and C. Y. Li, Zhong Guo Fa Ming Zhuan Li (Chinese patent), CN01822657A (2010).Google Scholar
  8. 8.
    C. Wittekind and M. Neid, Oncology, 69, 14 (2005).CrossRefPubMedGoogle Scholar
  9. 9.
    I. J. Fidler, Nat. Rev. Cancer, 3, 453 (2003).CrossRefPubMedGoogle Scholar
  10. 10.
    L. Paolucci and E. Rozengurt, Cancer Res., 59, 572 (1999).PubMedGoogle Scholar
  11. 11.
    J. L. Zugaza, J. Sinnett-Smith, J. Van Lint, and E. Rozengurt, EMBO J., 15, 6220 (1996).PubMedCentralPubMedGoogle Scholar
  12. 12.
    D. Lin, A. S. Edwards, J. P. Fawcett, G. Mbamalu, J. D. Scott, and T. Pawson, Nat. Cell. Biol., 2, 540 (2000).CrossRefPubMedGoogle Scholar
  13. 13.
    S. Etienne-Manneville and A. Hall, Cell, 106, 489 (2001).CrossRefPubMedGoogle Scholar
  14. 14.
    R. H. Sun, P. Gao, L. Chen, D. L. Ma, J. M. Wang, J. J. Oppenheim, and N. Zhang, Cancer Res., 65, 1433 (2005).CrossRefPubMedGoogle Scholar
  15. 15.
    J. S. Desgrosellier and D. A. Cheresh, Nat. Rev. Cancer, 10, 9 (2010).CrossRefPubMedCentralPubMedGoogle Scholar
  16. 16.
    N. Cordes and C. Park, Int. J. Radiat. Biol., 83, 753 (2007).CrossRefPubMedGoogle Scholar
  17. 17.
    A. K. Mitra, K. Sawada, P. Tiwari, K. Mui, K. Gwin, and E. Lengyel, Oncogene, 30, 1566 (2011).CrossRefPubMedCentralPubMedGoogle Scholar
  18. 18.
    A. J. Aasen, B. Kimland, and C. R. Enzell, Acta Chem. Scand., 27, 2107 (1973).CrossRefGoogle Scholar
  19. 19.
    D. Behr, I. Wahlberg, T. Nishida, and C. R. Enzell, Acta Chem. Scand. B, 32, 391 (1978).CrossRefGoogle Scholar
  20. 20.
    H. C. Huang, C. Y. Huang, S. Lin-Shiau, and J. K. Lin, Mol. Carcinogen, 48, 517 (2009).CrossRefGoogle Scholar
  21. 21.
    J. Wu, B. Zhang, M. Wu, H. Li, R. Niu, G. Ying, and N. Zhang, Invest. New Drugs, 28, 268 (2010).CrossRefPubMedGoogle Scholar
  22. 22.
    Y. J. Chen, Y. M. Tsai, C. D. Kou, K. L. Ku, H. S. Shie, and H. F. Liao, Life Sci., 85, 642 (2009).CrossRefPubMedGoogle Scholar
  23. 23.
    T. Y. Park, M. H. Park, W. C. Shin, M. H. Rhee, D. W. Seo, J. Y. Cho, and H. M. Kim, Biol. Pharm. Bull., 31, 1802 (2008).CrossRefPubMedGoogle Scholar
  24. 24.
    D. Kong, O. Mutsumi, Y. Hisashi, and Y. Takao, Eur. J. Cancer, 45, 857 (2009).CrossRefPubMedGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  1. 1.Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of PharmacyTianjin Medical UniversityTianjinP. R. China
  2. 2.Tianjin 4th Center HospitalTianjinP. R. China
  3. 3.Nanjing Integrated Traditional Chinese and Western Medicine HospitalNanjingP. R. China
  4. 4.Research Center of Basic Medical SciencesTianjin Medical UniversityTianjinP. R. China

Personalised recommendations