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Chemistry of Natural Compounds

, Volume 54, Issue 2, pp 238–241 | Cite as

Two New Benzolactones from the Leaves of Yunnan Local Sun Cured Tobacco and Their Bioactivities

  • Jianlian Shi
  • Xingmeng Xu
  • Chunbo Liu
  • Ling Ye
  • Peisong Yang
  • Fengmei Zhang
  • Pei He
  • Zhihua Liu
  • Mingming Miao
  • Shiyun Tang
  • Yadong Guo
  • Qinpeng Shen
Article
  • 34 Downloads

Two new benzolactones, 4-methoxy-6-(2-oxopropyl)isobenzofuran-1(3H)-one (1) and 4-methyl-6-(2-oxopropyl)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 anti-tobacoo mosaic virus (TMV) activities and cytotoxicity activities. The results revealed that compounds 1 and 2 showed high anti-TMV activity with inhibition rates of 32.6 and 30.2%. These rates are close to that of positive control. Compounds 1 and 2 also showed weak inhibitory activities against some tested human tumor cell lines.

Keywords

benzolactones Yunnan local sun cured tobacco anti-tobacco mosaic virus cytotoxicity activities 

Notes

Acknowledgment

This research was supported by the National Natural Science Foundation of China (No. 31360081), the Applied Fundamental Foundation of Yunnan Province (No. 2013FB097), and the Basic Research Foundation of Yunnan Tobacco Industry Co. Ltd. (2013FL05 and 2012JC01).

References

  1. 1.
    The Editorial Committee of the Administration Bureau of Flora of China, Flora of China, Vol. 67, Beijing Science and Technology Press, Beijing, 2005.Google Scholar
  2. 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.Google Scholar
  3. 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).CrossRefPubMedGoogle Scholar
  4. 4.
    X. Feng, Xin, J. S. Wang, J. Luo, and L. Y. Kong, J. Asian Nat. Prod. Res., 12, 252 (2010).Google Scholar
  5. 5.
    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).CrossRefGoogle Scholar
  6. 6.
    X. C. Wei, S. C. Sumithran, A. G. Deaciuc, H. R. Burton, L. P. Bush, L. P. Dwoskin, and P. A. Crooks, Life Sci., 78, 495 (2005).CrossRefPubMedGoogle Scholar
  7. 7.
    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).CrossRefPubMedGoogle Scholar
  8. 8.
    M. M. Miao, L. Li, Q. P. Shen, C. B. Liu, Y. K. Li, T. Zhang, F. M. Zhang, P. He, K. M. Wang, R. Z. Zhu, Y. K. Chen, and G. Y. Yang, Fitoterapia, 103, 260 (2015).CrossRefPubMedGoogle Scholar
  9. 9.
    Y. K. Li, Y. L. Zhao, N. J. Xiang, L. Yang, F. Wang, G. Y. Yang, and Z. Y. Wang, Heterocycles, 89, 2771 (2014).CrossRefGoogle Scholar
  10. 10.
    Y. Wang, C. B. Liu, Q. P. Shen, F. M. Zhang, P. He, Z. H. Liu, H. B. Zhang, X. D. Yang, M. M. Miao, and G. Y. Yang, Heterocycles, 91, 1198 (2015).CrossRefGoogle Scholar
  11. 11.
    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).CrossRefGoogle Scholar
  12. 12.
    G. Y. Yang, W. Zhao, T. Zhang, Y. X. Duan, Z. H. Liu, M. M. Miao, and Y. K. Chen, Heterocycles, 89, 183 (2014).CrossRefGoogle Scholar
  13. 13.
    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).CrossRefPubMedGoogle Scholar
  14. 14.
    S. Z. Shang, Y. X. Duan, X. Zhang, J. X. Pu, H. D. Sun, Z. Y. Chen, M. M. Miao, G. Y. Yang, and Y. K. Chen, Phytochem. Lett., 7, 413 (2014).Google Scholar
  15. 15.
    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).CrossRefGoogle Scholar
  16. 16.
    Q. P. Shen, L. Li, X. M. Xu, C. B. Liu, N. J. Xiang, F. M. Zhang, P. He, Z. H. Liu, S. Z. Shang, M. M. Miao, and G. Y. Yang, Heterocycles, 91, 1775 (2015).CrossRefGoogle Scholar
  17. 17.
    G. H. Kong, Y. P. Wu, J. L. Shi, N. J. Xiang, L. X. Liu, G. R. Yang, Y. K. Li, X. P. Lu, Q. Liu, and Q. F. Hu, Phytochem. Lett., 14, 230 (2015).CrossRefGoogle Scholar
  18. 18.
    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).CrossRefPubMedGoogle Scholar
  19. 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).CrossRefPubMedGoogle Scholar
  20. 20.
    Q. F. Hu, B. Zhou, J. M. Huang, Z. Y. Jiang, X. Z. Huang, L. Y. Yang, X. M. Gao, G. Y. Yang, and C. T. Che, J. Nat. Prod., 76, 1866 (2013).CrossRefPubMedGoogle Scholar
  21. 21.
    Q. F. Hu, B. Zhou, Y. Q. Ye, Z. Y. Jiang, X. Z. Huang, Y. K. Li, G. Du, G. Y. Yang, and X. M. Gao, J. Nat. Prod., 76, 1854 (2013).CrossRefPubMedGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Jianlian Shi
    • 1
    • 2
  • Xingmeng Xu
    • 1
    • 2
  • Chunbo Liu
    • 2
  • Ling Ye
    • 2
  • Peisong Yang
    • 3
  • Fengmei Zhang
    • 2
  • Pei He
    • 2
  • Zhihua Liu
    • 2
  • Mingming Miao
    • 2
  • Shiyun Tang
    • 2
  • Yadong Guo
    • 1
  • Qinpeng Shen
    • 2
  1. 1.School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Nature ProductsKunming Medical UniversityKunmingP. R. China
  2. 2.Key Laboratory of Tobacco Chemistry of Yunnan ProvinceChina Tobacco Yunnan Industrial Co., Ltd.KunmingP. R. China
  3. 3.School of Chemical Science and TechnologyYunnan UniversityKunmingP. R. China

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