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(±) Pestalactone D and pestapyrone F, two new isocoumarins from an endolichenic Pestalotiopsis rhododendri

The Journal of Antibiotics volume 76, pages 678–681 (2023)Cite this article

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Abstract

Three isocoumarins, including two new compounds, (±) pestalactone D (1) and pestapyrone F (2), as well as one known compound, pestapyrone D (3), were isolated from the culture of the endolichenic Pestalotiopsis rhododendri LF-19-12. The planar structures of all compounds were elucidated by NMR and MS spectra. And the absolute configurations of 1 were confirmed by single crystal X-ray diffraction analysis, indicative of it as a racemate of 4S/12S and 4R/12R enantiomers. Compound 1 exhibited weak anti-coronaviral activity against human coronavirus HCoV-229E with an EC50 of 77.61 μM. Based on the bioinformatics analysis, the biosynthetic pathway of 1 has been proposed.

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References

  1. Singh BN, Upreti DK, Gupta VK, Dai XF, Jiang Y. Endolichenic fungi: a hidden reservoir of next generation biopharmaceuticals. Trends Biotechnol. 2017;35:808–13.

    Article  CAS  PubMed  Google Scholar 

  2. Tripathi M, Joshi Y. Endolichenic fungi: a promising source for novel bioactive compounds. In: Tripathi M, Joshi Y, editors. Endolichenic fungi: present and future trends. Singapore: Springer Singapore; 2019. p. 69–118.

  3. Kellogg JJ, Raja HA. Endolichenic fungi: a new source of rich bioactive secondary metabolites on the horizon. Phytochem Rev. 2016;16:271–93.

    Article  Google Scholar 

  4. Zheng QC, Kong MZ, Zhao Q, Chen GD, Tian HY, et al. Chaetoglobosin Y, a new cytochalasan from Chaetomium globosum. Fitoterapia. 2014;93:126–31.

    Article  CAS  PubMed  Google Scholar 

  5. Dou Y, Wang X, Jiang D, Wang H, Jiao Y, et al. Metabolites from Aspergillus versicolor, an endolichenic fungus from the lichen Lobaria retigera. Drug Discov Ther. 2014;8:84–8.

    Article  CAS  PubMed  Google Scholar 

  6. Wipf P, Halter RJ. Chemistry and biology of wortmannin. Org Biomol Chem. 2005;3:2053–61.

    Article  CAS  PubMed  Google Scholar 

  7. Wu W, Dai H, Bao L, Ren B, Lu J, et al. Isolation and structural elucidation of proline-containing cyclopentapeptides from an endolichenic Xylaria sp. J Nat Prod. 2011;74:1303–8.

    Article  CAS  PubMed  Google Scholar 

  8. Wethalawe AN, Alwis YV, Udukala DN, Paranagama PA. Antimicrobial compounds isolated from endolichenic fungi: a review. Molecules. 2021;26:3901.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Luo M, Chang S, Li Y, Xi X, Chen M, et al. Molecular networking-based screening led to the discovery of a cyclic heptadepsipeptide from an endolichenic Xylaria sp. J Nat Prod. 2022;85:972–79.

    Article  CAS  PubMed  Google Scholar 

  10. Luo M, Wang M, Chang S, He N, Shan G, et al. Halogenase-targeted genome mining leads to the discovery of (+/−) pestalachlorides A1a, A2a, and their atropisomers. Antibiotics (Basel). 2022;11:1304.

    Article  CAS  PubMed  Google Scholar 

  11. Song RY, Wang XB, Yin GP, Liu RH, Kong LY, et al. Isocoumarin derivatives from the endophytic fungus, Pestalotiopsis sp. Fitoterapia. 2017;122:115–18.

    Article  CAS  PubMed  Google Scholar 

  12. Cai Y, Rao L, Zou Y. Genome mining discovery of a C(4)-alkylated dihydroisocoumarin pathway in fungi. Org Lett. 2021;23:2337–41.

    Article  CAS  PubMed  Google Scholar 

  13. Capon RJ. Extracting value: mechanistic insights into the formation of natural product artifacts – case studies in marine natural products. Nat Prod Rep. 2020;37:55–79.

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This research was co-funded by The National Natural Science Foundation of China (81973219 and 82104047), and CAMS Innovation Fund for Medical Sciences (CIFMS, 2021-I2M-1-028).

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  1. These authors contributed equally: Mengyuan Wang, Mengna Luo

Authors and Affiliations

  1. CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan xili No.1, Beijing, 100050, China

    Mengyuan Wang, Mengna Luo, Xiaotian Ding, Shanshan Chang, Ning He, Bin Hong & Yunying Xie

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  1. Mengyuan Wang
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Correspondence to Yunying Xie.

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Wang, M., Luo, M., Ding, X. et al. (±) Pestalactone D and pestapyrone F, two new isocoumarins from an endolichenic Pestalotiopsis rhododendri. J Antibiot 76, 678–681 (2023). https://doi.org/10.1038/s41429-023-00646-7

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  • DOI: https://doi.org/10.1038/s41429-023-00646-7

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