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A New Steroid Ester from the Leaves of Melia azedarach

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Chemistry of Natural Compounds Aims and scope

A new pregnane-type steroid, 2α,3β,16β-trihydroxy-5α-pregnane-20R-methacrylate (1), was isolated from the leaves of Melia azedarach, together with 17 known compounds. Their structures were elucidated by spectroscopic and mass-spectrometric analysis, including 1D, 2D NMR, ESI-MS, and HR-MS. Compound 1 was found to possess cytotoxicities against HepG2, K562, and SGC7901 cell lines, with IC50 values 18.6, 19.1, and 62.9 μM, respectively.

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References

  1. H. B. Liu, C. R. Zhang, S. H. Dong, L. Dong, Y. Wu, and J. M. Yue, J. Am. Chem. Soc., 59, 1003 (2011).

    CAS  Google Scholar 

  2. T. Namba, The Encyclopedia of Wakan-Yaku (Traditional Sino-Japanese Medicines) with Color Pictures, Hoikusya, Osaka, 1994, 247 pp.

  3. M. Okada, Newly Revised Illustrated Medicinal Plants of World, Hokuryukan Publishing Co., Ltd., Tokyo, 2002, 262 pp.

  4. M. D. Ambrosio and A. Guerriero, Phytochemistry, 60, 419 (2002).

    Article  Google Scholar 

  5. W. M. Zhang, J. Q. Liu, X. R. Peng, L. S. Wan, and Z. R. Zhang, Nat. Prod. Biopros., 4, 157 (2014).

    Article  CAS  Google Scholar 

  6. Z. X. Zhang, J. Zhou, K. Hayashi, and K. Kaneko, Phytochemistry, 27, 2935 (1988).

    Article  CAS  Google Scholar 

  7. L. Garrido, E. Zubia, M. J. Ortega, and J. Salva, Steroids, 65, 85 (2000).

    Article  CAS  Google Scholar 

  8. X. D. Luo, S. H. Wu, Y. B. Ma, and D. G. Wu, Chin. Chem. Lett., 11, 535 (2000).

    CAS  Google Scholar 

  9. R. Benvegnu, G. Cimino, S. D. Rosa, and S. D. Stefano, Experientia, 38, 1443 (1982).

    Article  CAS  Google Scholar 

  10. W. R. Nes, T. E. Varkey, D. R. Crump, and M. Gut, J. Org. Chem., 41, 3429 (1976).

    Article  CAS  Google Scholar 

  11. W. R. Nes and T. E. Varkey, J. Org. Chem., 41, 1652 (1976).

    Article  CAS  Google Scholar 

  12. A. Aiello, E. Fattorusso, and M. Menna, Steroids, 56, 513 (1991).

    Article  CAS  Google Scholar 

  13. M. Nakatani, H. Takao, I. Miura, and T. Hase, Phytochemistry, 24, 1945 (1985).

    Article  CAS  Google Scholar 

  14. S. B. Wu, Y. P. Ji, J. J. Zhu, Y. Zhao, G. Xia, Y. H. Hu, and J. F. Hu, Steroids, 74, 761 (2009).

    Article  CAS  Google Scholar 

  15. P. He, S. Li, S. J. Wang, Y. C. Yang, and J. G. Shi, Chin. J. Chin. Mater. Med., 30, 671 (2005).

    CAS  Google Scholar 

  16. X. L. Liu, M. S. Dong, X. H. Chen, M. Jiang, X. Lv, and G. Yan, Food Chem., 105, 548 (2007).

    Article  CAS  Google Scholar 

  17. F. Conforti, C. Statti, M. R. Loizzo, G. Sacchetti, F. Poli, and F. Menichini, Bio. Pharm. Bull., 28, 1098 (2005).

    Article  CAS  Google Scholar 

  18. L. Tang, Y. C. Chen, Z. B. Jiang, S. P. Zhong, W. Z. Chen, W. D. Chen, Y. J. Zhuang, and G. G. Shi, Chem. Nat. Compd., 53, 770 (2017).

    Article  CAS  Google Scholar 

  19. C. Gobel and I. Feussner, Phytochemistry, 70, 1485 (2009).

    Article  Google Scholar 

  20. M. Saleem, Cancer Lett., 285, 109 (2009).

    Article  CAS  Google Scholar 

  21. Y. J. You, N. H. Nam, Y. Kim, K. H. Bae, and B. Z. Ahn, Phytother. Res., 17, 341 (2003).

    Article  CAS  Google Scholar 

  22. X. H. Gan, X. Zhou, H. G. Chen, X. J. Gong, J. X. Zhang, and D. P. Wang, J. Trop. Subtrop. Bot., 17, 160 (2009).

    CAS  Google Scholar 

  23. S. Matsunaga, R. Tanaka, and M. Akagi, Phytochemistry, 27, 535 (1988).

    Article  CAS  Google Scholar 

  24. M. F. Otuki, J. Ferrerira, F. V. Lima, C. M. Silva, A. Malhriros, L. A. Muller, C. S. Cani, A. R. S. Santos, R. A. Yunes, and J. B. Calixto, J. Pharmacol. Exp. Ther., 313, 310 (2005).

    Article  CAS  Google Scholar 

  25. J. Y. Kim, H. J. Lim, and J. H. Ryu, Bioorg. Med. Chem. Lett., 18, 1511 (2008).

    Article  CAS  Google Scholar 

  26. J. Budzianowski and L. Skrzypczak, Phytochemistry, 38, 997 (1995).

    Article  CAS  Google Scholar 

  27. L. J. Mcgaw, A. K. Jager, and J. Staden, Fitoterapia, 73, 431 (2002).

    Article  CAS  Google Scholar 

  28. B. J. B. Wood, B. W. Nichols, and A. T. James, BBA-Lipids and Lipids Metabolism, 106, 261 (1965).

    Article  CAS  Google Scholar 

  29. A. C. Chibnall, E. F. Willians, A. L. Latner, and S. H. Piper, Biochem. J., 27, 1885 (1933).

    Article  CAS  Google Scholar 

  30. A. Pollard, A. C. Chibnall, and S. H. Piper, Biochem. J., 27, 1889 (1933).

    Article  CAS  Google Scholar 

  31. M. R. Habib, F. Nikkon, M. Rahman, M. E. Haque, and M. R. Karim, J. Biol. Sci., 10, 4174 (2007).

    CAS  Google Scholar 

  32. Z. J. Ma, X. Li, N. Li, and J. H. Wang, Fitoterapia, 73, 313 (2002).

    Article  CAS  Google Scholar 

  33. K. Tabata, K. Motani, N. Takayanagi, R. Nishimura, S. Asami, Y. Kimura, M. Ukiya, D. Hasegawa, T. Akihisa, and T. Suzuki, Biol. Pharm. Bull., 28, 1404 (2005).

    Article  CAS  Google Scholar 

  34. T. Kikuchi, E. Uchiyama, M. Ukiya, K. Tabata, Y. Kimura, T. Suzuki, and T. Akihisa, J. Nat. Prod., 74, 137 (2011).

    Article  CAS  Google Scholar 

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Acknowledgment

This work was supported by grants from the Natural Science Foundation of Fujian Province (No. 2016J01369), the Open Project of National Marine Bureau Key Laboratory of Marine Biogenetic Resources (HY201506, HY201604), and the Startup Fund for scientific research, Fujian Medical University (2016QH015). The authors are grateful to State Key Laboratory of Applied Organic Chemistry at Lanzhou University for measuring of NMR and mass spectra.

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Correspondence to Xiangbin Yu.

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Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2018, pp. 781–784.

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Ma, X., Zhou, F., Deng, Y. et al. A New Steroid Ester from the Leaves of Melia azedarach. Chem Nat Compd 54, 921–925 (2018). https://doi.org/10.1007/s10600-018-2513-x

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  • DOI: https://doi.org/10.1007/s10600-018-2513-x

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