Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Brief Communication
  • Published:

Two new diketopiperazines from the Cordyceps fungus Samsoniella sp. XY4

The Journal of Antibiotics volume 76, pages 735–740 (2023)Cite this article

Subjects

Abstract

Two new diketopiperazines, namely samsoniellain A (1) and samsoniellain B (2), together with two known compounds (3, 4) were isolated from Cordyceps fungus Samsoniella sp. XY4. The planar structures of 1 and 2 were determined by HRESIMS, 1D and 2D NMR spectroscopy. The absolute configurations of 1 and 2 were determined by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Results of antimicrobial activity indicated that compound 2 showed weak bacteriostatic activities against S. typhimurium χ 8956, H. influenza ATCC 10211, MRSA 2024 with the MIC values of 128, 256, and 256 μg ml−1, respectively. This is the first report about secondary metabolites of Samsoniella sp.

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

Access options

Buy this article

  • Purchase on Springer Link
  • Instant access to full article PDF
Buy now

Prices may be subject to local taxes which are calculated during checkout

Fig. 1
Fig. 2
Fig. 3

References

  1. Zhou XW, Gong ZH, Su Y, Lin J, Tang KX. Cordyceps fungi: natural products, pharmacological functions and developmental products. J Pharm Pharmacol. 2009;61:279–91.

    Article  CAS  PubMed  Google Scholar 

  2. Dworecka-Kaszak B. Cordyceps fungi as natural killers, new hopes for medicine and biological control factors. Ann Parasitol. 2014;60:151–8.

    PubMed  Google Scholar 

  3. Zheng P, Xia YL, Xiao GH, Xiong CH, Hu X, Zhang SW, Zheng HJ, Huang Y, Zhou Y, Wang SY, Zhao GP, Liu XZ, Leger RJS, Wang CS. Genome sequence of the insect pathogenic fungus Cordyceps militaris, a valued traditional Chinese medicine. Genome Biol. 2011;12:R116.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Lo HC, Hsieh C, Lin FY, Hsu TH. A systematic review of the mysterious caterpillar fungus Ophiocordyceps sinensis in Dong-ChongXiaCao (Dōng Chóng Xià Cǎo) and related bioactive ingredients. J Tradit Complement Med. 2013;3:16–32.

    Article  PubMed  PubMed Central  Google Scholar 

  5. Lu YZ, Luo FF, Cen K, Xiao GH, Yin Y, Li CR, Li ZZ, Zhan S, Zhang HZ, Wang CS. Omics data reveal the unusual asexual-fruiting nature and secondary metabolic potentials of the medicinal fungus Cordyceps cicadae. BMC Genomics. 2017;18:668.

    Article  PubMed  PubMed Central  Google Scholar 

  6. Chen XA, He X, Zhang M, Mao XM, Li YQ. An efficient genetic transformation system for Chinese medicine fungus Tolypocladium ophioglossoides. J Microbiol Methods. 2020;176:106032.

    Article  CAS  PubMed  Google Scholar 

  7. Kim HG, Song H, Yoon DH, Song BW, Park SM, Sung GH, Cho JY, Park HIL, Choi S, Song WO, Hwang KC, Kim TW. Cordyceps pruinosa extracts induce apoptosis of HeLa cells by a caspase dependent pathway. J Ethnopharmacol. 2010;128:342–51.

    Article  PubMed  Google Scholar 

  8. Xiao JH, Zhong JJ. Secondary metabolites from Cordyceps species and their antitumor activity studies. Recent Pat Biotechnol. 2007;1:123–37.

    Article  CAS  PubMed  Google Scholar 

  9. Yue GGL, Lau CBS, Fung KP, Leung PC, Ko WH. Effects of Cordyceps sinensis, Cordyceps militaris and their isolated compounds on ion transport in Calu-3 human airway epithelial cells. J Ethnopharmacol. 2008;117:92–101.

    Article  CAS  PubMed  Google Scholar 

  10. Yu HM, Wang BS, Huang SC, Duh PD. Comparison of protective effects between cultured Cordyceps militaris and natural Cordyceps sinensis against oxidative damage. J Agric Food Chem. 2006;54:3132–8.

    Article  CAS  PubMed  Google Scholar 

  11. Won SY, Park EH. Anti-inflammatory and related pharmacological activities of cultured mycelia and fruiting bodies of Cordyceps militaris. J Ethnopharmacol. 2005;96:555–61.

    Article  PubMed  Google Scholar 

  12. Li LQ, Song AX, Yin JY, Siu KC, Wong WT, Wu JY. Anti-inflammation activity of exopolysaccharides produced by a medicinal fungus Cordyceps sinensis Cs-HK1 in cell and animal models. Int J Biol Macromol. 2020;149:1042–50.

    Article  CAS  PubMed  Google Scholar 

  13. Ueda Y, Mori K, Satoh S, Dansako H, Ikeda M, Kato N. Anti-HCV activity of the Chinese medicinal fungus Cordyceps militaris. Biochem Biophys Res Commun. 2014;447:341–5.

    Article  CAS  PubMed  Google Scholar 

  14. Zhao X, Yu XH, Zhang GY, Zhang HY, Liu WW, Zhang CK, et al. Aqueous extracts of Cordyceps kyushuensis Kob induce apoptosis to exert anticancer activity. Biomed Res Int. 2018;2:1–8.

  15. Grudniewska A, Hayashi S, Shimizu M, Kato M, Suenaga M, Imagawa H, Ito T, Asakawa Y, Ban S, Kumada T, Hashimoto T, Umeyama A. Opaliferin, a new polyketide from cultures of entomopathogenic fungus Cordyceps sp. NBRC 106954. Org Lett. 2014;16:4695–7.

    Article  CAS  PubMed  Google Scholar 

  16. Wang M, Kornsakulkarn J, Srichomthong K, Feng T, Liu JK, Isaka M, Thongpanchang C. Antimicrobial anthraquinones from cultures of the ant pathogenic fungus Cordyceps morakotii BCC 56811. J Antibiot. 2019;72:141–7.

    Article  CAS  Google Scholar 

  17. Sun JF, Jin M, Zhou W, Diao SB, Zhou Y, Li SS, Wang X, Pan S, Jin XJ, Li G. A new ribonucleotide from Cordyceps militaris. Nat Prod Res. 2017;31:2537–43.

    Article  CAS  PubMed  Google Scholar 

  18. Xue YF, Wu LL, Ding YL, Cui XM, Han ZZ, Xu H. A new nucleoside and two new pyrrole alkaloid derivatives from Cordyceps militaris. Nat Prod Res. 2020;34:341–50.

    Article  CAS  PubMed  Google Scholar 

  19. Chu ZB, Chang J, Zhu Y, Sun X. Chemical constituents of Cordyceps cicadae. Nat Prod Commun. 2015;10:2145–6.

    PubMed  Google Scholar 

  20. Mongkolsamrit S, Noisripoom W, Thanakitpipattana D, Wutikhun T, Spatafora JW, Luangsa-Ard J. Disentangling cryptic species with isaria-like morphs in Cordycipitaceae. Mycologia. 2018;110:230–57.

    Article  PubMed  Google Scholar 

  21. Chen WH, Han YF, Liang JD, Tian WY, Liang ZQ. Morphological and phylogenetic characterisations reveal three new species of Samsoniella (Cordycipitaceae, Hypocreales) from Guizhou, China. MycoKeys. 2020;74:1–15.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Liang YJ, Ariyawansa HA, Becker JO, Yang JI. The evaluation of egg-parasitic fungi Paraboeremia taiwanensis and Samsoniella sp. for the biological control of Meloidogyne enterolobii on Chinese cabbage. Microorganisms. 2020;8:828.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Pandian AT, Arivudainambi USE, Bagyalakshmi, Rajendran A. Antimicrobial potential of endophytic fungus Colletotrichum gloeosporioides associated with madhuca longifolia L. Adv Appl Res. 2011;3:1–7.

    Google Scholar 

  24. Pierens GK. 1H and 13C NMR scaling factors for the calculation of chemical shifts in commonly used solvents using density functional theory. J Comput Chem. 2014;35:1388–94.

    Article  CAS  PubMed  Google Scholar 

  25. Qu CL, Yang X, Zhang SM, et al. Study of diketopiperazines from the marine-derived Streptomyces sp. 223. Chinese J Mar Drugs. 2015;34:23–28.

    Google Scholar 

  26. He JB, Kang DW, Chen X, et al. Secondary metabolites of Streptomyces sp. KC17012 and their antibacterial activity. Nat Prod Res Dev. 2022;34:1523–9.

    Google Scholar 

  27. Wattana-Amorn P, Charoenwongsa W, Williams C, Crump MP, Apichaisataienchote B. Antibacterial activity of cyclo(L-Pro-L-Tyr) and cyclo(D-Pro-L-Tyr) from Streptomyces sp. strain 22-4 against phytopathogenic bacteria. Nat Prod Res. 2016;30:1980–3.

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work was financially supported by grants from the Natural Science Foundation of China (Nos. 31960001 and 82260687), Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Chinese Medicine (No. 202101AZ070001-204), Yunnan Province Ten Thousand People Program “Young Top Talents” Special Project (YNWR-QNBJ-2019-161).

Author information

Authors and Affiliations

  1. School of Basic Medical Science, School of Chinese Medicine, Yunnan University of Chinese Medicine, Kun Ming, 650500, Yunnan, China

    Ke-Tao Zhang, Zhi-Pu Huang, Xiao-Rong Xu, Si-Heng Li, Yu-Xiao Xu, Qing Zhao & Xiao-Mei Zhang

Authors
  1. Ke-Tao Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhi-Pu Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xiao-Rong Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Si-Heng Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yu-Xiao Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Qing Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Xiao-Mei Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Qing Zhao or Xiao-Mei Zhang.

Ethics declarations

Conflict of interest

The authors declare no competing interests.

Additional information

Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, KT., Huang, ZP., Xu, XR. et al. Two new diketopiperazines from the Cordyceps fungus Samsoniella sp. XY4. J Antibiot 76, 735–740 (2023). https://doi.org/10.1038/s41429-023-00662-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41429-023-00662-7

Search

Advanced search

Quick links