Pestaloamides A and B, two spiro-heterocyclic alkaloid epimers from the plant endophytic fungus Pestalotiopsis sp. HS30


Pestaloamides A and B (1 and 2), two novel alkaloids featuring an unprecedented spiro[imidazothiazoledione-alkylidenecyclopentenone] scaffold, were obtained from the cultures of an endophytic fungus Pestalotiopsis sp. HS30 which inhabited the stems of Isodon xerophilus. Their planar structures and absolute configurations were fully determined by extensive spectroscopic analysis and X-ray crystallography. In addition, both compounds 1 and 2 showed the latent tumor immunotherapy activity through markedly promoting the cell surface engagement of NKG2D ligands involving MICA/B and ULBP1 in HCT116 cells.

This is a preview of subscription content, access via your institution.


  1. 1(a)

    Guo W, Liu L, Xiang C, Chen J, Liang XJ. Sci China Chem, 2019, 62: 1557–1560

    CAS  Article  Google Scholar 

  2. 1(b)

    Ribas A, Wolchok JD. Science, 2018, 359: 1350–1355

    CAS  Article  Google Scholar 

  3. 2

    Orange JS, Fassett MS, Koopman LA, Boyson JE, Strominger JL. Nat Immunol, 2002, 3: 1006–1012

    CAS  Article  Google Scholar 

  4. 3

    Cifaldi L Locatelli F, Marasco E, Moretta L, Pistoia V. Trends Mol Med, 2017, 23: 1156–1175

    CAS  Article  Google Scholar 

  5. 4

    Rönsberg D, Debbab A, Mándi A, Vasylyeva V, Böhler P, Stork B, Engelke L, Hamacher A, Sawadogo R, Diederich M, Wray V, Lin WH, Kassack MU, Janiak C, Scheu S, Wesselborg S, Kurtán T, Aly AH, Proksch P. J Org Chem, 2013, 78: 12409–12425

    Article  Google Scholar 

  6. 5

    Zhu H, Wang B, Kong L, An T, Li G, Zhou H, Gong L, Zhao Z, Gong Y, Sun H, Puno P, Li Y. Cell Chem Biol, 2019, 26: 1122–1132.e6

    CAS  Article  Google Scholar 

  7. 6

    Tang JW, Kong LM, Zu WY, Hu K, Li XN, Yan BC, Wang WG, Sun HD, Li Y, Puno PT. Org Lett, 2019, 21: 771–775

    CAS  Article  Google Scholar 

  8. 7

    Wu L Wang S, Song Y, Wang X, Yan X. Sci China Chem, 2016, 59: 30–39

    CAS  Article  Google Scholar 

  9. 8

    Fu P Kong F, Li X, Wang Y, Zhu W. Org Lett, 2014, 16: 3708–3711

    CAS  Article  Google Scholar 

  10. 9

    Yin WB, Grundmann A, Cheng J, Li SM. J Biol Chem, 2009, 284: 100–109

    CAS  Article  Google Scholar 

  11. 10

    Fontecave M, Ollagnier-de-Choudens S, Mulliez E. Chem Rev, 2003, 103: 2149–2166

    CAS  Article  Google Scholar 

  12. 11

    Li C, Ge B, Nicotra M, Stern JNH, Kopcow HD, Chen X, Strominger JL. Proc Natl Acad Sci USA, 2008, 105: 3017–3022

    CAS  Article  Google Scholar 

  13. 12(a)

    Bae DS, Hwang YK, Lee JK. Cell Immunol, 2012, 276: 122–127

    CAS  Article  Google Scholar 

  14. 12(b)

    Smyth MJ, Swann J, Cretney E, Zerafa N, Yokoyama WM, Hayakawa Y. J Exp Med, 2005, 202: 583–588

    CAS  Article  Google Scholar 

  15. 13

    Nausch N, Cerwenka A. Oncogene, 2008, 27: 5944–5958

    CAS  Article  Google Scholar 

Download references


This work was supported by the Second Tibetan Plateau Scientific Expedition and Research (STEP) Program (2019QZKK0502), the National Natural Science Foundation of China (81874298), the CAS “Light of West China” Program (Pema-Tenzin Puno) and the Yunnan Science Fund for Distinguished Young Scholars (2019FJ002).

Author information



Corresponding authors

Correspondence to Yan Li or Pema-Tenzin Puno.

Ethics declarations

Conflict of interest The authors declare that they have no conflict of interest.

Supporting Information for

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Su, XZ., Zhu, YY., Tang, JW. et al. Pestaloamides A and B, two spiro-heterocyclic alkaloid epimers from the plant endophytic fungus Pestalotiopsis sp. HS30. Sci. China Chem. 63, 1208–1213 (2020).

Download citation


  • alkaloids
  • endophytic fungus
  • structure elucidation
  • tumor immunotherapy