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Daldispones A and B, two new cyclopentenones from Daldinia sp. CPCC 400770

The Journal of Antibiotics volume 74, pages 215–218 (2021)Cite this article

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Abstract

Two new cyclopentenone derivatives, daldispones A (1) and B (2) were isolated from the fungus Daldinia sp. CPCC 400770. Their structures and absolute configurations were elucidated by extensive spectroscopic analyses and calculated electronic circular dichroism (ECD). Compounds 1 and 2 exhibited significant anti-influenza A virus activities with IC50 values of 16.0 and 7.4 μM, respectively. Compound 2 showed moderate antibacterial activities against Staphylococcus aureus, Enterococcus faecalis and Bacillus cereus.

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References

  1. Zhang YL, Ge HM, Zhao W, Dong H, Xu Q, Li SH, Li J, Zhang J, Song YC, Tan RX. Unprecedented immunosuppressive polyketides from Daldinia eschscholzii, a mantis-associated fungus. Angew Chem Int Ed. 2008;47:5823–6.

    Article  CAS  Google Scholar 

  2. Zhang YL, Zhang J, Jiang N, Lu YH, Wang L, Xu SH, Wang W, Zhang GF, Xu Q, Ge HM, Ma J, Song YC, Tan RX. Immunosuppressive polyketides from mantis-associated Daldinia eschscholzii. J Am Chem Soc. 2011;133:5931–40.

    Article  CAS  Google Scholar 

  3. Zhang AH, Liu W, Jiang N, Xu Q, Tan RX. Spirodalesol, an NLRP3 inflammasome activation inhibitor. Org Lett. 2016;18:6496–9.

    Article  CAS  Google Scholar 

  4. Lin L, Jiang N, Hu H, Mei Y, Yang J, Tan R. Cytotoxic and antibacterial polyketide-indole hybrids synthesized from indole-3-carbinol by Daldinia eschscholzii. Acta Pharm Sin B. 2019;9:369–80.

    Article  Google Scholar 

  5. Liao HX, Shao TM, Mei RQ, Huang GL, Zhou XM, Zheng CJ, Wang CY. Bioactive secondary metabolites from the culture of the mangrove-derived fungus Daldinia eschscholtzii HJ004. Mar Drugs. 2019;17:710.

    Article  CAS  Google Scholar 

  6. Barnes EC, Jumpathong J, Lumyong S, Voigt K, Hertweck C. Daldionin, an unprecedented binaphthyl derivative, and diverse polyketide congeners from a fungal orchild endophyte. Chem Eur J. 2016;22:4551–5.

    Article  CAS  Google Scholar 

  7. Nagasawa H, Nagura F, Mohamad SB, Uto Y, Zhu JW, Tsukuda T, Hashimoto T, Asakawa Y, Hori H. Apoptosis induction in HCT116 cells by cytochalasins isolated from the fungus Daldinia vernicosa. Phytomedicine. 2000;6:403–9.

    Article  CAS  Google Scholar 

  8. Zhao ZZ, Chen HP, Huang Y, Zhang SB, Li ZH, Feng T, Liu JK. Bioactive polyketides and 8,14-seco-ergosterol from fruiting bodies of the ascomycete Daldinia childiae. Phytochemistry. 2017;142:68–75.

    Article  CAS  Google Scholar 

  9. Qin XD, Dong ZJ, Liu JK. Concentricolide, an anti-HIV agent from the ascomycete Daldinia concentrica. Helv Chim Acta. 2006;89:127–33.

    Article  CAS  Google Scholar 

  10. Stadler M, Læssøe T, Fournier J, Decock C, Schmieschek B, Tichy HV, Peršoh D. A polyphasic taxonomy of Daldinia (Xylariaceae). Stud Mycol. 2014;77:1–143.

    Article  Google Scholar 

  11. Lee IK, Kim SE, Yeom JH, Ki DW, Lee MS, Song JG, Kim YS, Seok SJ, Yun BS. Daldinan A, a novel isoindolinone antioxidant from the ascomycete Daldinia concentrica. J Antibiot. 2012;65:95–7.

    Article  CAS  Google Scholar 

  12. Stadler M, Baumgartner M, Grothe T, Mühlbauer A, Seip S, Wollweber H. Concentricol, a taxonomically significant triterpenoid from Daldinia concentrica. Phytochemistry. 2001;56:787–93.

    Article  CAS  Google Scholar 

  13. Quang DN, Hashimoto T, Tanaka M, Baumgartner M, Stadler M, Asakawa Y. Concentriols B, C and D, three squalene-type triterpenoids from the ascomycete Daldinia concentrica. Phytochemistry. 2002;61:345–53.

    Article  CAS  Google Scholar 

  14. Wu Z, Xie Z, Wu M, Li X, Li W, Ding W, She Z, Li C. New antimicrobial cyclopentenones from Nigrospora sphaerica ZMT05, a fungus derived from Oxya chinensis Thunber. J Agric Food Chem. 2018;66:5368–72.

    Article  CAS  Google Scholar 

  15. Mansoor TA, Hong J, Lee CO, Sim CJ, Im KS, Lee DS, Jung JH. New cytotoxic metabolites from a marine sponge Homaxinella sp. J Nat Prod. 2004;67:721–4.

    Article  CAS  Google Scholar 

  16. You J, Dai H, Chen Z, Liu G, He Z, Song F, Yang X, Fu H, Zhang L. Chen X. Trichoderone, a novel cytotoxic cyclopentenone and cholesta-7,22-diene-3β,5α,6β-triol, with new activities from the marine-derived fungus Trichoderma sp. J Ind Microbiol Biotechnol. 2010;37:245–52.

    Article  CAS  Google Scholar 

  17. Fang F, Zhao J, Ding L, Huang C, Naman B, He S, Wu B, Zhu P, Luo Q, Gerwick WH, Yan X, Wang Q, Zhang Z, Cui W. 5-Hydroxycyclopenicillone, a new β-amyloid fibrillization inhibitor form a sponge-derived fungus Trichoderma sp. HPQJ-34. Mar Drugs. 2017;15:260.

    Article  Google Scholar 

  18. Cai J, Zhou XM, Yang X, Tang MM, Liao QY, Meng BZ, Liao S, Chen GY. Three new bioactive natural products from the fungus Talaromyces assiutensis JTY2. Bioorg Chem. 2020;94:103362.

    Article  CAS  Google Scholar 

  19. Zhou ZZ, Zhu HJ, Yang CL, Liu YJ, Jiang N, Xiao YS, Shi LY, Jiao RH, Ge HM, Tan RX. Dalestones A and B, two anti-inflammatory cyclopentenones from Daldinia eschscholzii with an edited strong promoter for the global regulator LaeA-like gene. Chin J Nat Med. 2019;17:387–93.

    PubMed  Google Scholar 

  20. Gao Q, Wang Z, Liu Z, Li X, Zhang Y, Zhang Z, Cen S. A cell-based high-throughput approach to identify inhibitors of influenza A virus. Acta Pharm Sin B. 2014;4:301–6.

    Article  Google Scholar 

  21. Clinical and Laboratory Standards Institute (CLSI). Performance standards for antimicrobial susceptibility testing; nineteenth informational supplement. CLSI document M100-S19. Wayne, PA, 2009.

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Acknowledgements

The work was financially supported by the Drug Innovation Major Project (2018ZX09711001-007-001), the National Natural Science Foundation of China (No. 81402835), CAMS Innovation Fund for Medical Sciences (No. 2016-12M-3-14) and the National Microbial Resource Center (No. NMRC-2020-3).

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Authors and Affiliations

  1. Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China

    Guowei Gu, Guowei Cai, Yujia Wang, Jinglin Bai, Tao Zhang, Shan Cen, Dewu Zhang & Liyan Yu

  2. Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China

    Li Li

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  1. Guowei Gu
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Correspondence to Dewu Zhang or Liyan Yu.

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Gu, G., Cai, G., Wang, Y. et al. Daldispones A and B, two new cyclopentenones from Daldinia sp. CPCC 400770. J Antibiot 74, 215–218 (2021). https://doi.org/10.1038/s41429-020-00384-0

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