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:

Formanilides from the culture broth of Perenniporia fraxinea

The Journal of Antibiotics volume 76, pages 731–734 (2023)Cite this article

Subjects

Abstract

A new formanilide dimer, fraxinin (1), and three known formanilides (2‒4) were isolated from the culture broth of Perenniporia fraxinea using silica gel and Sephadex LH-20 column chromatographies, medium-pressure liquid chromatography (MPLC), and preparative HPLC. The structures of these compounds were determined by spectroscopic methods, such as NMR and mass analysis, and by comparison of the spectra with previously reported data. The free radical scavenging activities of the isolated compounds were assessed using 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Compounds 1‒3 exhibited ABTS radical scavenging activity with IC50 values in the range of 57.2–250.2 μM. Compounds 2 and 4 marginally reduced disease incidence of powdery mildew with a control value of 42% at 1.0 mg ml−1 in cucumber leaf disk assay.

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

References

  1. Szczepkowski A. Perenniporia fraxinea (fungi, polyporales). Pol Bot J. 2004;49:73–7.

    Google Scholar 

  2. Wen CN, Hu DB, Bai X, Wang F, Li ZH, Feng T, et al. Chemical constituents from fruiting bodies of Basidiomycete Perenniporia subacida. Fitoterapia. 2016;109:179–84.

    Article  CAS  PubMed  Google Scholar 

  3. Hirotani M, Ino C, Furuya T, Shirot M. Perenniporiol derivatives six triterpenoids from the cultured mycelia of Perenniporia ochroleuca. Phytochemistry. 1984;23:1129–34.

    Article  CAS  Google Scholar 

  4. Wu LS, Hu CL, Han T, Zheng CJ, Ma XQ, Rahman K, et al. Cytotoxic metabolites from Perenniporia tephropora, an endophytic fungus from Taxus chinensis var. mairei. Appl Microbiol Biotechnol. 2013;97:305–15.

    Article  CAS  PubMed  Google Scholar 

  5. Kim JY, Woo EE, Ha LS, Ki DW, Lee IK, Yun BS. Three new meroterpenoids from culture broth of Perenniporia medulla-panis and their antioxidant activities. J Antibiot. 2019;72:625–8.

    Article  CAS  Google Scholar 

  6. Feng Y, Wang L, Niu S, Li L, Si Y, Liu X, et al. Naphthalenones from a Perenniporia sp. inhabiting the larva of a phytophagous weevil, Euops chinesis. J Nat Prod. 2012;75:1339–45.

    Article  CAS  PubMed  Google Scholar 

  7. Kim DH, Kim MJ, Kim DW, Kim GY, Kim JK, Gebru YA, et al. Changes of phytochemical components (urushiols, polyphenols, gallotannins) and antioxidant capacity during Fomitella fraxinea–mediated fermentation of Toxicodendron vernicifluum bark. Molecules. 2019;24:683.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Tanaka N, Kitamura A, Mizushina Y, Sugawara F, Sakaguchi K. Fomitellic acids, triterpenoid inhibitors of eukaryotic DNA polymerases from a basidiomycete, Fomitella fraxinea. J Nat Prod. 1998;61:193–7.

    Article  CAS  PubMed  Google Scholar 

  9. Cho SM, Yun BS, Yoo ID, Koshino H. Structure of fomitellan A, a mannofucogalactan from the fruiting bodies of Fomitella fraxinea. Bioorg Med Chem Lett. 2011;21:204–6.

    Article  CAS  PubMed  Google Scholar 

  10. Yoshikawa K, Koso K, Shimomura M, Tanaka M, Yamamoto H, Imagawa H, et al. Yellow pigments, fomitellanols A and B, and drimane sesquiterpenoids, cryptoporic acids p and q, from Fomitella fraxinea and their inhibitory activity against COX and 5-LO. Molecules. 2013;18:4181–91.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Park SS, Lee JS, Bae KG, Yu KH, Han HC, Min TJ. Antioxidative activity and structural analysis of the steroid compound from Fomitella fraxinea. Kor J Mycol. 2001;29:67–71.

    Google Scholar 

  12. Yin J, Zhang J, Cai C, Deng G-J, Gong H. Catalyst-free transamidation of aromatic amines with formamide derivatives and tertiary amides with aliphatic amines. Org Lett. 2019;21:387–92.

    Article  CAS  PubMed  Google Scholar 

  13. Corbett MD, Corbett BR. Reaction of nitroso aromatics with glyoxylic acid. A new path to hydroxamic acids. J Org Chem. 1980;45:2834–9.

    Article  CAS  Google Scholar 

  14. Ashalatha K, Raja Shantha Reddy A, Raveesha H. Evaluation of phytochemical compounds and antimicrobial activities of Hemidesmus indicus. Asian J Pharm Clin Res. 2019;12:102–6.

    CAS  Google Scholar 

  15. Kim JY, Ki DW, Lee YJ, Ha LS, Woo EE, Lee IK et al. Consoramides A–C, New Zwitterionic Alkaloids from the Fungus Irpex consors. Mycobiology 2021;49:434–7.

  16. Lee IK, Kim SE, Yeom JH, Ki DW, Lee MS, Song JG, et al. Daldinan A, a novel isoindolinone antioxidant from the ascomycete Daldinia concentrica. J Antibiot. 2012;65:95–7.

    Article  CAS  Google Scholar 

  17. Ki DW, Kim DW, Hwang BS, Lee SW, Seok SJ, Lee IK, et al. New antioxidant sesquiterpenes from a culture broth of Coprinus echinosporus. J Antibiot. 2015;68:351–3.

    Article  CAS  Google Scholar 

  18. Li YH, Windham MT, Trigiano RN, Fare DC, Spiers JM, Copes WE. Evaluation for resistance to powdery mildew in Cornus species and hybrids using a leaf disk assay. J Environ Hort. 2007;25:131–3.

    Google Scholar 

Download references

Acknowledgements

This work was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture and Forestry (IPET) through Crop Viruses and Pests Response Industry Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA) (grant number 321103-3) and also supported by BK21 FOUR Program by Jeonbuk National University Research Grant. Authors thank Ms. Ji-Young Oh, Center for University-wide Research Facilities (CURF) at Jeonbuk National University, for performing the NMR measurements.

Author information

Authors and Affiliations

  1. Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Jeonbuk National University, Gobong-ro 79, Iksan, 54596, Korea

    Dae-Cheol Choi, Dae-Won Ki, Young-Hee Kim, In-Kyoung Lee & Bong-Sik Yun

Authors
  1. Dae-Cheol Choi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dae-Won Ki
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Young-Hee Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. In-Kyoung Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Bong-Sik Yun
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bong-Sik Yun.

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

Choi, DC., Ki, DW., Kim, YH. et al. Formanilides from the culture broth of Perenniporia fraxinea. J Antibiot 76, 731–734 (2023). https://doi.org/10.1038/s41429-023-00665-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41429-023-00665-4

Search

Advanced search

Quick links