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Anthraquinone and Naphthoquinone Derivatives from the Pericarps of Juglans sigillata

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Chemistry of Natural Compounds Aims and scope

Four new anthraquinones (1–4), along with four known ones (5–8) and five known naphthoquinones (9–13), were isolated from the green pericarps of Juglans sigillata. The structures of the new compounds were elucidated as 1,3-diethoxycarbonyl-8-hydroxy-9,10-anthraquinone (1), 1,3-diethoxycarbonyl-5-hydroxy-9,10-anthraquinone (2), 1-ethoxycarbonyl-8-hydroxy-9,10-anthraquinone (3), and 1-ethoxycarbonyl-5-hydroxy-9,10-anthraquinone (4), based on extensive spectroscopic methods including HR-ESI-MS and 1D and 2D NMR spectra. Compounds 1–12 were evaluated for their in vitro cytotoxicities against MCF-7 and HT-29 cancer cell lines by MTT assay. Compounds 3 and 7 showed weak cytotoxicities against HT-29 with IC50 of 91.7 and 60.6 μM, respectively. Compounds 9–12 exhibited moderate cytotoxicities against MCF-7 and HT-29 with IC50 ranging from 7.2 to 23.9 μM.

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References

  1. Q. Liu, P. Zhao, X. C. Li, M. R. Jacob, C. R. Yang, and Y. J. Zhang, Helv. Chim. Acta, 93, 265 (2010).

    Article  CAS  Google Scholar 

  2. J. X. Liu, D. L. Di, X. Y. Huang, and C. Li, Chin. Chem. Lett., 18, 943 (2007).

    Article  CAS  Google Scholar 

  3. H. Y. Yu, X. Li, F. Y. Meng, H. F. Pi, P. Zhang, and H. L. Ruan, J. Asian Nat. Prod. Res., 13, 581 (2011).

    Article  CAS  Google Scholar 

  4. Y. Y. Zhou, B. Y. Yang, Y. Q. Jiang, Z. X. Liu, Y. X. Liu, X. L. Wang, and H. X. Kuang, Molecules, 20, 15572 (2015).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. L. Liu, W. Li, T. Sasaki, Y. Asada, and K. Koike, J. Nat. Med., 64, 496 (2010).

    Article  CAS  PubMed  Google Scholar 

  6. X. N. Gao, X. F. Sun, and G. X. Huang, J. Trad. Chin. Med., 35, 1487 (2013).

    CAS  Google Scholar 

  7. Y. W. Zhang, H. Lin, Y. L. Bao, Y. Wu, C. L. Yu, Y. X. Huang, and Y. X. Li, Biochem. Syst. Ecol., 44, 136 (2012).

    Article  CAS  Google Scholar 

  8. D. L. Yao, M. Jin, C. H. Zhang, J. Luo, Z. Jiang, M. S. Zheng, J. M. Cui, and G. Li, Chem. Nat. Compd., 52, 93 (2016).

    Article  CAS  Google Scholar 

  9. M. Jin, S. Diao, C. Zhang, S. Cao, J. Sun, R. Li, Z. Jiang, M. Zheng, J. K. Son, and G. Li, Nat. Prod. Res., 29, 1839 (2015).

    Article  CAS  PubMed  Google Scholar 

  10. G. Li, C. S. Seo, S. H. Lee, Y. Jahng, H. W. Chang, C. S. Lee, M. H. Woo, and J. K. Son, Bull. Korean Chem. Soc., 25, 397 (2004).

    Article  CAS  Google Scholar 

  11. G. Li, M. L. Xu, H. G. Choi, S. H. Lee, Y. D. Jahng, C. S. Lee, D. C. Moon, M. H. Woo, and J. K. Son, Chem. Pharm. Bull., 51, 262 (2003).

    Article  CAS  PubMed  Google Scholar 

  12. J. Li, J. X. Sun, H. Y. Yu, Z. Y. Chen, X. Y. Zhao, and H. L. Ruan, Chin. Chem. Lett., 24, 521 (2013).

    Article  CAS  Google Scholar 

  13. C. L. Si, S. Fan, and L. L. An, Chem. Nat. Compd., 52, 1008 (2016).

    Article  CAS  Google Scholar 

  14. C. L. Si, P. P. Qin, H. Y. Hu, J. Z. Jiang, and Y. H. Ni, J. Biobased Mater. Bio., 5, 287 (2011).

    Article  CAS  Google Scholar 

  15. C. L. Si, Y. Zhang, Z. Y. Zhu, and S. C. Liu, Chem. Nat. Compd., 47, 442 (2011).

    Article  CAS  Google Scholar 

  16. Z. B. Li, J. Y. Wang, B. Jiang, X. L. Zhang, L. J. An, and Y. M. Bao, Phytomedicine, 14, 846 (2007).

    Article  CAS  PubMed  Google Scholar 

  17. Z. B. Li, J. Y. Wang, J. Yang, X. L. Zhang, L. J. An, and Y. M. Bao, Phytother. Res., 23, 551 (2009).

    Article  CAS  PubMed  Google Scholar 

  18. N. Xin, M. Hasan, W. Li, and Y. Li, Mol. Med. Rep., 9, 1313 (2014).

    Article  CAS  PubMed  Google Scholar 

  19. H. Xu, X. Yu, S. Qu, and D. Sui, Bioorg. Med. Chem. Lett., 23, 3631 (2013).

    Article  CAS  PubMed  Google Scholar 

  20. H. L. Xu, X. F. Yu, S. C. Qu, R. Zhang, X. R. Qu, Y. P. Chen, X. Y. Ma, and D. Y. Sui, Eur. J. Pharmacol., 645, 14 (2010).

    Article  CAS  PubMed  Google Scholar 

  21. Y. Yao, Y. W. Zhang, L. G. Sun, B. Liu, Y. L. Bao, H. Lin, Y. Zhang, L. H. Zheng, Y. Sun, C. L. Yu, Y. Wu, G. N. Wang, and Y. X. Li, Apoptosis, 17, 832 (2012).

    Article  CAS  PubMed  Google Scholar 

  22. H. Lin, Y. W. Zhang, L. H. Zheng, X. Y. Meng, Y. L. Bao, Y. Wu, C. L. Yu, Y. X. Huang, and Y. X. Li, Helv. Chim. Acta, 94, 1488 (2011).

    Article  CAS  Google Scholar 

  23. S. M. Ju, H. Y. Song, S. J. Lee, W. Y. Seo, D. H. Sin, A. R. Goh, Y. H. Kang, I. J. Kang, M. H. Won, J. S. Yi, D. J. Kwon, Y. S. Bae, S. Y. Choi, and J. Park, Biochem. Biophys. Res. Commun., 387, 115 (2009).

    Article  CAS  PubMed  Google Scholar 

  24. B. S. Min, N. Nakamura, H. Miyashiro, Y. H. Kim, and M. Hattori, Chem. Pharm. Bull., 48, 194 (2000).

    Article  CAS  PubMed  Google Scholar 

  25. B. S. Min, H. K. Lee, S. M. Lee, Y. H. Kim, K. H. Bae, T. Otake, N. Nakamura, and M. Hattori, Arch. Pharmacol. Res., 25, 441 (2002).

    Article  CAS  Google Scholar 

  26. G. Li, S. Y. Lee, K. S. Lee, S. W. Lee, S. H. Kim, S. H. Lee, C. S. Lee, M. H. Woo, and J. K. Son, Arch. Pharmacol. Res., 26, 466 (2003).

    Article  Google Scholar 

  27. H. Yang, S. H. Sung, J. Kim, and Y. C. Kim, Planta Med., 77, 841 (2011).

    Article  CAS  PubMed  Google Scholar 

  28. P. H. Nguyen, H. S. Choi, T. K. Q. Ha, J. Y. Seo, J. L. Yang, D. W. Jung, D. R. Williams, and W. K. Oh, Bioorg. Med. Chem. Lett., 27, 40 (2017).

    Article  CAS  PubMed  Google Scholar 

  29. W. Nam, S. P. Kim, S. H. Nam, and M. Friedman, Molecules, 22, 265 (2017).

    Article  CAS  PubMed Central  Google Scholar 

  30. K. Danielsen and D. W. Aksnes, Magn. Reson. Chem., 30, 359 (1992).

    Article  CAS  Google Scholar 

  31. M. R. Dhananjeyan, Y. P. Milev, M. A. Kron, and M. G. Nair, J. Med. Chem., 48, 2822 (2005).

    Article  CAS  PubMed  Google Scholar 

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Acknowledgment

We thank the staff at the analytical and testing center of Huazhong University of Science and Technology for collecting the spectroscopic data. This work was supported by the Natural Science Foundation of China (21572073, 31770380, and 31270394) and the Fundamental Research Funds for the Central Universities (2016YXMS150).

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Authors and Affiliations

  1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College of Huazhong University of Science and Technology, 430030, Wuhan, P. R. China

    Jing-Jing Liang, Jia Zhou, Jian Song & Han-Li Ruan

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  1. Jing-Jing Liang
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  2. Jia Zhou
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  3. Jian Song
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  4. Han-Li Ruan
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Correspondence to Han-Li Ruan.

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Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2019, pp. 373–377.

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Liang, JJ., Zhou, J., Song, J. et al. Anthraquinone and Naphthoquinone Derivatives from the Pericarps of Juglans sigillata. Chem Nat Compd 55, 435–439 (2019). https://doi.org/10.1007/s10600-019-02708-5

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  • DOI: https://doi.org/10.1007/s10600-019-02708-5

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