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Chemistry of Natural Compounds

, Volume 48, Issue 6, pp 958–962 | Cite as

Cytotoxic flavonoids from the flowers of Achillea millefolium

  • Chang-Hong Huo
  • Yong Li
  • Man-Li Zhang
  • Yu-Fang Wang
  • Qing Zhang
  • Fang Qin
  • Qing-Wen Shi
  • Hiromasa Kiyota
Article

A new natural product, 8,8'-bi-3-O-methylquercetin (9), and eight known flavonoids were isolated from the flowers of Achillea millefolium. Their structures were established on the basis of spectral evidence. All the spectral data of these compounds were reassigned after interpretation of their 2D NMR spectroscopic data. Compounds 2, 5, and 7 exhibited antiproliferative activity against human breast cancer cell line MCF7WT. In addition, 2 and 5 showed antiproliferative activity against human prostatic cancer cell line PC-3, while the other compounds did not show inhibitory effects in two human tumor cell lines tested.

Keywords

Achillea millefolium Compositae flavonoids antiproliferative activity 

Notes

Acknowledgment

Financial support by the National Natural Science Foundation of China (81072551), the Scientific Research Foundation for Returning Overseas Chinese Scholars of Hebei Province (2006-02), the Scientific Research Foundation of Hebei Province (08B032 and C2010000489), JSPS KAKENHI (22580112), and Syngenta Ltd. (2008-Hebei Medical University-Syngenta02) is gratefully acknowledged.

References

  1. 1.
    R. F. Chandler, S. N. Hooper, and M. J. Harvey, Econ. Bot., 36, 203 (1982).CrossRefGoogle Scholar
  2. 2.
    X.-T. Si, M.-L. Zhang, Q.-W. Shi, and H. Kiyota, Chem. Biodivers., 3, 1163 (2006).PubMedCrossRefGoogle Scholar
  3. 3.
    A. S. Goldberg, E. E. E. C. Mueller, and S. J. Desalva, J. Pharm. Sci., 58, 938 (1969).PubMedCrossRefGoogle Scholar
  4. 4.
    A. J. Falk, S. J. Smolenski, L. Bauer, and C. L. Bell, J. Pharm. Sci., 64, 1838 (1975).PubMedCrossRefGoogle Scholar
  5. 5.
    B. Csupor-Loffler, Z. Hajdu, I. Zupko, B. Rethy, G. Falkay, P. Forgo, and J. Hohmann, Phytother. Res., 23, 672 (2009).PubMedCrossRefGoogle Scholar
  6. 6.
    A. Trendafilova, M. Todorova, B. Mikhova, and H. Duddeck, Chem. Nat. Comp., 43, 212 (2007).CrossRefGoogle Scholar
  7. 7.
    S. J. Smolenski, C. L. Bell, and L. Bauer, Lloydia, 30, 144 (1967).Google Scholar
  8. 8.
    S. Glasl, P. Mucaji, I. Werner, A. Presser, and J. Jurenitsch, Z. Naturforsch., 57C, 976 (2002).Google Scholar
  9. 9.
    S. Z. Kasymov and G. P. Sidyakin, Khim. Prir. Soedin., 246 (1972).Google Scholar
  10. 10.
    G. Verzar-Petri, C. Bhanh-Nhu, J. Tamas, L. Radics, and K. Ujszaszi, Herba Hung., 19, 105 (1980).Google Scholar
  11. 11.
    G. J. Hochmannova, V. Herout, and F. Sorm, Collect. Czech. Chem. Commun., 26, 1826 (1961).Google Scholar
  12. 12.
    Verzar-Petri, Phytochemistry, 18, 331 (1979).Google Scholar
  13. 13.
    B. M. Hausen, J. Breuer, J. Weglewski, and G. Ruecker, Cont. Dermat., 24, 274 (1991).CrossRefGoogle Scholar
  14. 14.
    G. Ruecker, D. Manns, and J. Breuer, Arch. Pharm., 324, 979 (1991).CrossRefGoogle Scholar
  15. 15.
    G. Ruecker, D. Manns, and J. Breuer, Arch. Pharm., 326, 901 (1993).CrossRefGoogle Scholar
  16. 16.
    T. Tozyo, Y. Yoshimura, K. Sakurai, N. Uchida, Y. Takeda, H. Nakai, and H. Ishii, Chem. Pharm. Bull., 42, 1096 (1994).PubMedCrossRefGoogle Scholar
  17. 17.
    H. Greger and O. Hofer, Phytochemistry, 28, 2363 (1989).CrossRefGoogle Scholar
  18. 18.
    F. Bohlmann, C. Zdero, and A. Suwita, Chem. Ber., 107, 1038 (1974).CrossRefGoogle Scholar
  19. 19.
    Haidara, L. O. Zamir, Q. W. Shi, and G. Batist, Cancer Lett., 242, 180 (2006).Google Scholar
  20. 20.
    V. U. Ahmad, F. T. B. M. A. Khan, and R. B. Tareen, Phytochemstry, 38, 1305 (1995).Google Scholar
  21. 21.
    Y. M. Liu and D. Q. Yu, Acta Pharm. Sin., 20, 514 (1985).Google Scholar
  22. 22.
    F. Masao, N. Masahiro, and I. Takao, Chem. Pharm. Bull., 30, 1151 (1982).CrossRefGoogle Scholar
  23. 23.
    C. Long, P. Sauleau, B. David, C. Lavaud, V. Cassabois, F. Ausseil, and G. Massiot, Phytochemistry, 64, 567 (2003).PubMedCrossRefGoogle Scholar
  24. 24.
    L. Yang, M. Y. Wang, Y. Y. Zhao, and Y. Y. Tu, Zhongguo Zhong Yao Za Zhi, 29, 647 (2004).PubMedGoogle Scholar
  25. 25.
    E. Rodriguez, N. J. Carman, P. Chavez, and T. J. Mabry, Phytochemistry, 11, 1507 (1972).CrossRefGoogle Scholar
  26. 26.
    Y. Liu, X. F. Li, A. L. Liu, Z. H. Li, G. H. Du, and H. L. Qin, Zhongcaoyao, 40, 1356 (2009).Google Scholar
  27. 27.
    M. Z. Zhurinov, A. M. Esimova, A. A. Taldybaeva, and Z. K. Narymbaeva, Kazakstan Respublikasy Ulttyk Gylym Akademiyasynyn, 17 (2002).Google Scholar
  28. 28.
    L. Zhai, K. Kita, C. Wano, Y. Wu, S. Sugaya, and N. Suzuki, Exp. Cell Res., 305, 244 (2005).PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Chang-Hong Huo
    • 1
  • Yong Li
    • 2
  • Man-Li Zhang
    • 1
  • Yu-Fang Wang
    • 1
  • Qing Zhang
    • 1
  • Fang Qin
    • 1
  • Qing-Wen Shi
    • 1
  • Hiromasa Kiyota
    • 3
  1. 1.School of Pharmaceutical SciencesHebei Medical UniversityHebeiP. R. China
  2. 2.Hebei Key Laboratory of Forensic MedicineHebei Medical UniversityHebeiP. R. China
  3. 3.Graduate School of Agricultural ScienceTohoku UniversitySendaiJapan

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