Chemistry of Natural Compounds

, Volume 54, Issue 2, pp 249–252 | Cite as

Anti-Tobacco Mosaic Virus Isocoumarins from the Fermentation Products of the Endophytic Fungus Aspergillus versicolor

  • Yan-Qing Duan
  • Li-Zhi Dang
  • Ju-Xing Jiang
  • Yi-Peng Zhang
  • Neng-Jun Xiang
  • Hong-Mei Yang
  • Gang Du
  • Hai-Ying Yang
  • Qing-Qing Li
Article
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Two new isocoumarins, (3R)-methyl-8-hydroxy-6-(hydroxymethyl)-7-methoxydihydroisocoumarin (1) and (3R)-methyl-7,8-dimethoxy-6-(hydroxymethyl)dihydroisocoumarin (2), together with three known isocoumarins (3–5), were isolated from the fermentation products of an endophytic fungus Aspergillus versicolor. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. The anti-tobacco mosaic virus (anti-TMV) activities of compounds 1 and 2 were evaluated. Compounds 1 and 2 showed anti-TMV activities with inhibition rates of 21.8 and 18.6% at the concentration of 20 μM, respectively.

Keywords

isocoumarins fermentation products Aspergillus versicolor anti-tobacco mosaic virus activities 
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Notes

Acknowledgment

This research was financially supported by the National Natural Science Foundation of China (Nos. 21462051 and 31560099), the Foundation of Yunnan Province (No. 2015BA006 and Category of Industry Guide No. 2014-01), the Foundation of China Tobacco Yunnan Industrial Co., Ltd. (2015539200340277), and the Foundation of China National Tobacco Corporation (110201402040).

References

  1. 1.
    D. O. Inglis, J. Binkley, M. S. Skrzypek, M. B. Arnaud, G. C. Cerqueira, P. Shah, W. Farrell, R. W. Jennifer, and S. Gavin, BMC Microbiol., 13, 91 (2013).CrossRefPubMedPubMedCentralGoogle Scholar
  2. 2.
    R. A. Samson, C. M. Visagie, J. Houbraken, S. B. Hong, V. Hubka, C. H. W. Klaassen, G. Perrone, K. A. Seifert, A. Susca, J. B. Tanney, J. Varga, S. Koscube, G. Szigeti, T. Yanguchi, and J. C. Frisvad, Stud. Mycol., 78, 141 (2014).CrossRefPubMedPubMedCentralGoogle Scholar
  3. 3.
    M. Zhou, M. M. Miao, G. Du, S. Z. Shang, W. Zhao, Z. H. Liu, G. Y. Yang, C. T. Che, Q. F. Hu, and X. M. Gao, Org. Lett., 16, 5016 (2014).CrossRefPubMedGoogle Scholar
  4. 4.
    M. Zhou, J. Lou, Y. K. Li, Y. D. Wang, K. Zhou, B. K. Ji, W. Dong, X. M. Gao, G. Du, and Q. F. Hu, J. Brazil. Chem. Soc., 26, 545 (2015).Google Scholar
  5. 5.
    M. Zhou, G. Du, H. Y. Yang, C. F. Xia, J. X. Yang, Y. Q. Ye, X. M. Gao, X. N. Li, and Q. F. Hu, Planta Med., 81, 235 (2015).CrossRefPubMedGoogle Scholar
  6. 6.
    Y. Q. Ye, C. F. Xia, J. X. Yang, Y. Qin, M. Zhou, X. M. Gao, G. Du, H. Y. Yang, X. M. Li, and Q. F. Hu, Phytochem. Lett., 10, 215 (2014).CrossRefGoogle Scholar
  7. 7.
    Y. Q. Ye, C. F. Xia, J. X. Yang, Y. C. Yang, Y. Qin, X. M. Gao, G. Du, X. M. Li, and Q. F. Hu, B. Kor. Chem. Soc., 35, 3059 (2014).Google Scholar
  8. 8.
    U. W. Hawas, A. A. El-Beih, and A. M. El-Halawany, Arch. Pharm. Res., 35, 1749 (2012).CrossRefPubMedGoogle Scholar
  9. 9.
    N. Y. Ji, X. H. Liu, F. P. Miao, and M. F. Qiao, Org. Lett., 15, 2327 (2013).CrossRefPubMedGoogle Scholar
  10. 10.
    R. X. Li, S. X. Chen, S. B. Niu, L. D. Guo, J. Yin, and Y. S. Che, Fitoterapia, 96, 88 (2014).CrossRefPubMedGoogle Scholar
  11. 11.
    J. Qi, C. L. Shao, Z. Y. Li, L. S. Gan, X. M. Fu, W. T. Bian, H. Y. Zhao, and C. Y. Wang, J. Nat. Prod., 76, 571 (2013).CrossRefPubMedGoogle Scholar
  12. 12.
    M. Zhou, J. Lou, Y. K. Li, Y. D. Wang, K. Zhou, B. K. Ji, W. Dong, X. M. Gao, G. Du, and Q. F. Hu, Arch. Pharm. Res., 38, 786 (2015).Google Scholar
  13. 13.
    S. L. Luo, X. J. Huang, Y. Wang, R. W. Jiang, L. Wang, L. L. Bai, Q. L. Peng, C. L. Song, D. M. Zhang, and W. C. Ye, Fitoterapia, 95, 115 (2014).CrossRefPubMedGoogle Scholar
  14. 14.
    Y. Q. Ye, C. F. Xia, J. X. Yang, Y. C. Yang, X. M. Gao, G. Du, H. Y. Yang, Y. K. Li, and Q. F. Hu, Heterocycles, 89, 2369 (2014).CrossRefGoogle 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.
    K. Tianpanich, S. Prachya, S. Wiyakrutta, C. Mahidol, R. Somsak, and P. Kittakoop, J. Nat. Prod., 74, 79 (2011).CrossRefPubMedGoogle Scholar
  17. 17.
    L. C. Di Stasi, D. Camuesco, A. Nieto, W. Vilegas, A. Zarzuelo, and J. Galvez, Planta Med., 70, 315 (2004).CrossRefPubMedGoogle Scholar
  18. 18.
    M. S. Islam, K. Ishigami, and H. Watanabe, Tetrahedron, 63, 1074 (2007).CrossRefGoogle Scholar
  19. 19.
    W. A. L. van Otterlo, J. P. Michael, and C. B. de Koning, Synth. Commun., 37, 3611 (2007).CrossRefGoogle Scholar
  20. 20.
    H. L. Jiang, X. H. Luo, X. Z. Wang, J. L. Yang, X. J. Yao, P. Crews, F. A. Valeriote, and Q. X. Wu, Fitoterapia, 95, 115 (2012).Google Scholar
  21. 21.
    Q. F. Hu, B. Zhou, J. M. Huang, X. M. Gao, L. D. Shu, G. Y. Yang, and C. T. Che, J. Nat. Prod., 76, 292 (2013).CrossRefPubMedGoogle Scholar
  22. 22.
    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

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

Authors and Affiliations

  • Yan-Qing Duan
    • 1
  • Li-Zhi Dang
    • 1
  • Ju-Xing Jiang
    • 1
  • Yi-Peng Zhang
    • 1
  • Neng-Jun Xiang
    • 1
  • Hong-Mei Yang
    • 4
  • Gang Du
    • 4
  • Hai-Ying Yang
    • 4
  • Qing-Qing Li
    • 2
    • 3
  1. 1.China Tobacco Yunnan Industrial Co., LtdKunmingP. R. China
  2. 2.Life Science CollegeSouthwest Forestry UniversityKunmingP. R. China
  3. 3.Kunming Xianghao Technology Co. Ltd.KunmingP. R. China
  4. 4.Key Laboratory of Chemistry in Ethnic Medicinal ResourcesYunnan Minzu UniversityKunmingP. R. China

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