Chemical Constituents of the Endophytic Fungus Ophiocordyceps sobolifera

  • Kuan-Ju Feng
  • Ming-Jen ChengEmail author
  • Shuen-Shin Yang
  • Ming-Der Wu
  • Sung-Yuan Hsieh
  • Hing-Yuen Chan
  • Yung-Shun Su
  • Yu-Ta Chou
  • Hsun-Shuo ChangEmail author

Fractionation of the BuOH-soluble fraction of the liquid fermentation of an endophytic fungus Ophiocordyceps sobolifer BCRC 38180 associated with the root of Taiwanese Ilex formosana (Aquifoliaceae) resulted in the isolation of one new diketopiperazine, soboliferamide (1), and one metabolite isolated for the first time from a natural source, cyclo-(Ile-Ser) (2), along with 18 previously identified compounds, 320. Their structures were elucidated by means of spectroscopic and mass-spectrometric analyses, especially 1D and 2D NMR spectroscopy, as well as HR-ESI-MS.


Ophiocordyceps sobolifera Clavicipitaceae secondary metabolites diketopiperazine 


  1. 1.
    G. H. Sung, J. M. Sung, N. L. Hywel-Jones, and J. W. Spatafora, Mol. Phylogenet. Evol., 44, 1204 (2007).CrossRefGoogle Scholar
  2. 2.
    J. Xu, Y. Huang, X. X. Chen, S. C. Zheng, P. Chen, and M. H. Mo, Phytother. Res., 30, 1572 (2016).CrossRefGoogle Scholar
  3. 3.
    P. X. Chen, S. Wang, S. Nie, and M. Marcone, J. Funct. Foods, 5, 550 (2013).CrossRefGoogle Scholar
  4. 4.
    S. Yang and H. Zhang, J. Biol. Engi., 10, 8 (2016).Google Scholar
  5. 5.
    K. Yonezawa, K. Yamada, and I. Kouno, Chem. Pharm. Bull., 59, 106 (2011).CrossRefGoogle Scholar
  6. 6.
    M. Falorni, M. Satta, S. Conti, and G. Giacomelli, Tetrahedron: Asymmetry, 4, 2389 (1993).CrossRefGoogle Scholar
  7. 7.
    J. Wei, X.-Y. Zhang, S. Deng, L. Cao, Q.-H. Xue, and J.-M. Gao, Nat. Prod. Res., 31, 2062 (2017).CrossRefGoogle Scholar
  8. 8.
    R. Huang, T. Yan, Y. Peng, X. Zhou, X. Yang, and Y. Liu, Chem. Nat. Compd., 50, 191 (2014).CrossRefGoogle Scholar
  9. 9.
    S. D. Bull, S. G. Davies, and W. O. Moss, Tetrahedron: Asymmetry, 9, 321 (1998).CrossRefGoogle Scholar
  10. 10.
    M. R. Park, Y. Kim, S. Lee, and I. Seon Kim, Pest. Manag. Sci., 65, 1114 (2009).CrossRefGoogle Scholar
  11. 11.
    H. Li, J. Xiao, Y. Q. Gao, J. J. Tang, A. L. Zhang, and J. M. Gao, J. Agric. Food Chem., 62, 3734 (2014).CrossRefGoogle Scholar
  12. 12.
    I. A. M. Asiri, J. M. Badr, and D. T. A. Youssef, Phytochem. Lett., 13, 53 (2015).CrossRefGoogle Scholar
  13. 13.
    R. Villano, M. R. Acocella, and A. Scettri, Tetrahedron Lett., 55, 2442 (2014).CrossRefGoogle Scholar
  14. 14.
    Q. Yan, E. Gin, M. G. Banwell, A. C. Willis, and P. D. Carr, J. Org. Chem., 82, 4328 (2017).CrossRefGoogle Scholar
  15. 15.
    Y. Liu, H. B. Jiang, Z.-P. Xu, Y.-G. Cheng, S.-W. Lv, B.-Y. Yang, H.-W. Guo, and H.-X. Kuang, Molecules, 22, 828 (2017).CrossRefGoogle Scholar
  16. 16.
    D. Scarpi, L. Bartali, A. Casini, and E. G. Occhiato, Eur. J. Org. Chem., 2013, 1306 (2013).CrossRefGoogle Scholar
  17. 17.
    M. L. Yang, P. C. Kuo, T. L. Hwang, and T. S. Wu, J. Nat. Prod., 74, 1996 (2011).CrossRefGoogle Scholar
  18. 18.
    Z. Wang, X. Wu, Y. N. Liang, L. Wang, Z. X. Song, J. L. Liu, and Z. S. Tang, Molecules, 21, pii: E1267 (2016).Google Scholar
  19. 19.
    H. X. Wei, X. W. Fang, X. S. Xie, S. P. Zhang, Y. Jiang, and S. H. Wu, Chem. Nat. Compd., 53, 794 (2017).CrossRefGoogle Scholar
  20. 20.
    Y. M. Ying, W. G. Shan, W. H. Liu, and Z. J. Zhan, Chem. Nat. Compd., 49, 184 (2013).CrossRefGoogle Scholar
  21. 21.
    V. G. Nebieridze, A. V. Skhirtladze, E. P. Kemertelidze, and M. Ganzera, Chem. Nat. Compd., 53, 1 (2017).Google Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Kuan-Ju Feng
    • 1
  • Ming-Jen Cheng
    • 2
    Email author
  • Shuen-Shin Yang
    • 3
  • Ming-Der Wu
    • 2
  • Sung-Yuan Hsieh
    • 2
  • Hing-Yuen Chan
    • 2
  • Yung-Shun Su
    • 4
  • Yu-Ta Chou
    • 5
  • Hsun-Shuo Chang
    • 1
    • 3
    Email author
  1. 1.Graduate Institute of Natural ProductsCollege of Pharmacy, Kaohsiung Medical UniversityKaohsiungTaiwan
  2. 2.Bioresource Collection and Research Center (BCRC)Food Industry Research and Development Institute (FIRDI)HsinchuTaiwan
  3. 3.School of Pharmacy, College of PharmacyKaohsiung Medical UniversityKaohsiungTaiwan
  4. 4.Graduate Institute of Medicine, College of MedicineKaohsiung Medical UniversityKaohsiungTaiwan
  5. 5.Department of Obstetrics & Gynecology, E-Da HospitalI-Shou UniversityKaohsiungTaiwan

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