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

Abstract

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.

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Acknowledgements

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).

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Correspondence to Yan Li or Pema-Tenzin Puno.

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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). https://doi.org/10.1007/s11426-020-9762-0

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Keywords

  • alkaloids
  • endophytic fungus
  • structure elucidation
  • tumor immunotherapy