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Euglobal-IIIa, a novel acylphloroglucinol-sesquiterpene derivative from Eucalyptus robusta: absolute structure and cytotoxicity

Abstract

Euglobal-IIIa (1), a novel acylphloroglucinol-sesquiterpene derivative, and a known analogue, have been isolated from leaves of Eucalyptus robusta. The structures was elucidated by extensive spectroscopic data and by comparison with data reported in literature, while the absolute configuration of 1 was determined by the X-ray diffraction analysis. Compound 1 exhibited comparable cytotoxicity with that of cisplatin against five human cancer cell lines HL-60, SMMC-7721, A-549, MCF-7, and SW480 with IC50 values of 15.7, 15.5, 17.6, 14.3, and 21.8 µM, respectively.

References

  1. [1] (a)

    Sawada, T.; Kozuka, M.; Komiya, T.; Amano, T.; Goto, M. Chem. Pharm. Bull.1980, 28, 2546–2548.

    CAS  Article  Google Scholar 

  2. [1] (b)

    Amano, T.; Komiya, T.; Hori, M.; Goto, M.; Kozuka, M.; Sawada, T. J. Chromatogr.1981, 208, 347–355.

    CAS  Article  Google Scholar 

  3. [1] (c)

    Kokumai, M.; Konoshima, T.; Kozuka, M.; Haruna, M.; Ito, K. J. Nat. Prod.1991, 54, 1082–1086.

    CAS  Article  Google Scholar 

  4. [1] (d)

    Takasaki, M.; Konoshima, T.; Kozuka, M.; Haruna, M.; Ito, K.; Crow, W. D.; Paton, D. M. Chem. Pharm. Bull.1994, 42, 2113–2116.

    PubMed  CAS  Article  Google Scholar 

  5. [1] (e)

    Cheng, Q.; Snyder, J. K. J. Org. Chem.1988, 53, 4562–4567.

    CAS  Article  Google Scholar 

  6. [1] (f)

    Takasaki, M.; Konoshima, T.; Kozuka, M.; Haruna, M.; Ito, K. Nat. Med. (Tokyo)1997, 51, 486–490.

    CAS  Google Scholar 

  7. [1] (g)

    Takasaki, M.; Konoshima, T.; Kozuka, M.; Haruna, M.; Ito, K.; Yoshida, S. Chem. Pharm. Bull.1994, 42, 2177–2179.

    CAS  Article  Google Scholar 

  8. [2] (a)

    Takasaki, M.; Konoshima, T.; Fujitani, K.; Yoshida, S.; Nishimura, H.; Tokuda, H.; Nishino, H.; Iwashima, A.; Kozuka, M. Chem. Pharm. Bull.1990, 38, 2737–2739.

    PubMed  CAS  Article  Google Scholar 

  9. [2] (b)

    Takasaki, M.; Konoshima, T.; Kozuka, M.; Tokuda, H. Biol. Pharm. Bull.1995, 18, 435–438.

    PubMed  CAS  Article  Google Scholar 

  10. [2] (c)

    Takasaki, M.; Konoshima, T.; Etoh, H.; Pal Singh, I.; Tokuda, H.; Nishino, H. Cancer Lett.2000, 155, 61–65.

    PubMed  CAS  Article  Google Scholar 

  11. [2] (d)

    Bharate, S. B.; Bhutani, K. K.; Khan, S. I.; Tekwani, B. L.; Jacob, M. R.; Khan, I. A.; Singh, I. P. Bioorg. Med. Chem.2006, 14, 1750–1760.

    PubMed  CAS  Article  Google Scholar 

  12. [2] (e)

    Kozuka, M.; Sawada, T.; Mizuta, E.; Kasahara, F.; Amano, T.; Komiya, T.; Goto, M. Chem. Pharm. Bull.1982, 30, 1964–1973.

    CAS  Article  Google Scholar 

  13. [3]

    Satoh, H.; Etoh, H.; Watanabe, N.; Kawagishi, H.; Arai, K.; Ina, K. Chem. Lett.1992, 21, 1917–1920.

    Article  Google Scholar 

  14. [4]

    Fu, H. Z.; Luo, Y. M.; Li, C. J.; Yang, J. Z.; Zhang, D. M. Org. Lett.2010, 12, 656–659.

    PubMed  CAS  Article  Google Scholar 

  15. [5]

    Mosmann, T. J. Immunol. Methods1983, 65, 55–63.

    PubMed  CAS  Article  Google Scholar 

  16. [6]

    Reed, L. J.; Muench, H. Am. J. Hyg.1938, 27, 493–497.

    Google Scholar 

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Correspondence to Qin-Shi Zhao.

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Peng, LY., He, J., Xu, G. et al. Euglobal-IIIa, a novel acylphloroglucinol-sesquiterpene derivative from Eucalyptus robusta: absolute structure and cytotoxicity. Nat. Prod. Bioprospect. 1, 101–103 (2011). https://doi.org/10.1007/s13659-011-0021-9

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  • DOI: https://doi.org/10.1007/s13659-011-0021-9

Keywords

  • Eucalyptus robusta
  • acylphloroglucinol-sesquiterpene
  • absolute structure
  • cytotoxicity