Skip to main content
Log in

Two New Isobenzofurans from Yunnan Local Sun-Cured Tobacco and Their Cytotoxicity

  • Published:
Chemistry of Natural Compounds Aims and scope

Two new isobenzofurans, 1-(3-hydroxypropanoyl)-2-methoxy-isobenzofuran-1(3H)-one (1) and 2-methoxy-1-prenyl-isobenzofuran-1(3H)-one (2), were isolated from the leaves of Yunnan local sun-cured tobacco. Their structures were determined by means of HR-ESI-MS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1 and 2 were tested for their cytotoxicity. The results revealed that compound 1 exhibited cytotoxicity for NB4, A549, SHSY5Y, PC3, and MCF7 cells with IC50 values of 2.8, 5.4, 6.9, 3.8, and 4.9 μM, and compound 2 exhibited cytotoxicity for NB4, A549, SHSY5Y, PC3, and MCF7 cells with IC50 values of 6.6, 7.8, 9.4, 7.0, and 9.2 μM, respectively.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1

Similar content being viewed by others

References

  1. The Editorial Committee of the Administration Bureau of Flora of China, Flora of China, Vol. 67, Beijing Science and Technology Press, Beijing, 2005.

  2. A. Rodgman and T. A. Perfetti, The Chemical Components of Tobacco and Tobacco Smoke, CRC Press, Taylor and Francis Group, Boca Raton, Florida, 2008.

  3. S. Z. Shang, W. Zhao, J. G. Tang, X. M. Xu, H. D. Sun, J. X. Pu, Z. H. Liu, M. M. Miao, Y. K. Chen, and G. Y. Yang, Fitoterapia, 108, 1 (2016).

    Article  CAS  PubMed  Google Scholar 

  4. G. H. Kong, Y. P. Wu, W. Li, Z. Y. Xia, Q. Liu, K. M. Wang, P. He, R. Z. Zhu, X. X. Si, and G. Y. Yang, Heterocycles, 92, 331 (2016).

    Article  CAS  Google Scholar 

  5. R. Shakirov, M. V. Telezhenetskaya, and I. A. Bessonova, Chem. Nat. Compd., 32, 216 (1996).

    Article  Google Scholar 

  6. Y. K. Chen, X. S. Li, G. Y. Yang, Z. Y. Chen, Q. F. Hu, and M. M. Miao, J. Asian Nat. Prod. Res., 14, 450 (2012).

    Article  CAS  PubMed  Google Scholar 

  7. X. M. Gao, X. S. Li, X. Z. Yang, H. X. Mu, Y. K. Chen, G. Y. Yang, and Q. F. Hu, Heterocycles, 85, 147 (2012).

    Article  CAS  Google Scholar 

  8. J. X. Chen, H. Q. Leng, Y. X. Duan, W. Zhao, G. Y. Yang, Y. D. Guo, Y. K. Chen, and Q. F. Hu, Phytochem. Lett., 6, 144 (2013).

    Article  CAS  Google Scholar 

  9. W. Zhao, L. Li, P. Lei, L. Yang, S. Z. Shang, J. G. Tang, G. Y. Yang, Y. K. Chen, and M. M. Miao, Phytochem. Lett., 12, 125 (2015).

    Article  CAS  Google Scholar 

  10. H. Q. Leng, J. X. Chen, Y. Hang, Y. X. Duan, G. Y. Yang, Y. K. Chen, Y. D. Guo, Q. F. Hu, and M. M. Miao, Chem. Nat. Compd., 49, 1028 (2014).

    Article  CAS  Google Scholar 

  11. G. Y. Yang, W. Zhao, T. Zhang, Y. X. Duan, Z. H. Liu, M. M. Miao, and Y. K. Chen, Heterocycles, 89, 183 (2014).

    Article  CAS  Google Scholar 

  12. S. Z. Shang, W. X. Xu, P. Lei, W. Zhao, J. G. Tang, M. M. Miao, H. D. Sun, J. X. Pu, Y. K. Chen, and G. Y. Yang, Fitoterapia, 99, 35 (2014).

    Article  CAS  PubMed  Google Scholar 

  13. S. Z. Shang, Y. X. Duan, X. Zhang, J. X. Pu, H. D. Sun, Z. Y. Chen, Mi. M. Miao, G. Y. Yang, and Y. K. Chen, Phytochem. Lett., 7, 413 (2014).

  14. S. Z. Shang, W. X. Xu, L. Li, J. G. Tang, W. Zhao, P. Lei, M. M. Miao, H. D. Sun, J. X. Pu, Y. K. Chen, and G. Y. Yang, Phytochem. Lett., 11, 53 (2015).

    Article  CAS  Google Scholar 

  15. C. Lei, W. X. Xu, J. Wu, S. J. Wang, J. Q. Sun, Z. Y. Chen, and G. Y. Yang, Chem. Nat. Compd., 51, 43 (2015).

    Article  CAS  Google Scholar 

  16. S. A. Shvets, P. K. Kintya, O. N. Gutsu, and V. I. Grishkovets, Chem. Nat. Compd, 31, 332 (1995).

    Article  Google Scholar 

  17. Q. F. Hu, B. Zhou, X. M. Gao, L. Y. Yang, L. D. Shu, Y. Q. Shen, G. P. Li, C. T. Che, and G. Y. Yang, J. Nat. Prod., 75, 1909 (2012).

    Article  CAS  PubMed  Google Scholar 

  18. J. Wu, T. Tokunaga, M. Kondo, K. Ishigami, S. Tokuyama, T. Suzuki, J. H. Choi, H. Hirai, and H. Kawagishi, J. Nat. Prod., 78, 155 (2015).

    Article  CAS  PubMed  Google Scholar 

  19. M. Zhou, K. Zhou, X. M. Gao, Z. Y. Jiang, J. J. Lv, Z. H. Liu, G. Y. Yang, M. M. Miao, C. T. Che, and Q. F. Hu, Org. Lett., 17, 2638 (2015).

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgment

This research was supported by the National Natural Science Foundation of China (Nos. 31360081, 21562049, 31400303), the Basic Research Foundation of Yunnan Province (Nos. 2013FB097, 2014FB163, 2015FB162), and the Basic Research Foundation of Yunnan Tobacco Industry Co. Ltd (2012JC01).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zhi-Hua Liu.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2017, pp. 50–52.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shen, QP., Xu, XM., Zhang, FM. et al. Two New Isobenzofurans from Yunnan Local Sun-Cured Tobacco and Their Cytotoxicity. Chem Nat Compd 53, 59–62 (2017). https://doi.org/10.1007/s10600-017-1911-9

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-017-1911-9

Keywords

Navigation