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:

Phaeolschidin F, a new symmetrical bis(styrylpyrone) derivative with redox-catalyzing activity from the mushroom Gymnopilus aeruginosus (order Agaricales)

The Journal of Antibiotics volume 76, pages 236–238 (2023)Cite this article

Subjects

Abstract

Phaeolschidin F (1) was isolated from fruiting bodies of the bitter and toxic mushroom Gymnopilus aeruginosus. Structure analysis by NMR and MS revealed that 1 is a new symmetrical bis(styrylpyrone). A series of anti-oxidant and pro-oxidant tests characterized that 1 is a redox catalyst having more anti-oxidant and less pro-oxidant activities than quercetin.

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. Sandargo B, Chepkirui C, Cheng T, Chaverra-Muñoz L, Thongbai B, Stadler M, Hüttel S. Biological and chemical diversity go hand in hand: Basidomycota as source of new pharmaceuticals and agrochemicals. Biotechnol Adv. 2019;37:107344.

    Article  CAS  PubMed  Google Scholar 

  2. Hatfield GM, Valdes LJ. The occurrence of psilocybin in Gymnopilus species. Lloydia. 1978;41:140–4.

    CAS  PubMed  Google Scholar 

  3. Ohta T, Aizawa K, Kamo S, Tabei N, Oshima Y, Nozoe S. Stereochemistry of Polyisoprenepolyols Isolated from Fungi Genus Gymnopilus. Symp Chem Nat Prod. 1996;38:307–12.

    Google Scholar 

  4. Soares RB, Dinis-Oliveira RJ, Oliveira NG. An updated review on the psychoactive, toxic and anticancer properties of kava. J Clin Med. 2022;11:4039.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Purtov KV, Petushkov VN, Baranov MS, Mineev KS, Rodionova NS, Kaskova ZM, et al. The chemical basis of fungal bioluminescence. Angew Chem Int Ed. 2015;54:8124–8.

    Article  CAS  Google Scholar 

  6. Zhang N, Wu L, Liu X, Shen X. Plant-derived kavalactones and their bioactivities. Med Res. 2018;2:170019.

    Article  Google Scholar 

  7. Wangun JVK, Hertweck C. Squarrosidine and Pinillidine: 3,3´-fused bis(styrylpyrones) from Pholiota squarrosa and Phellinus pini. Eur J Org Chem. 2007;2007:3292–5.

  8. Jung J-Y, Lee I-K, Seok S-J, Lee H-J, Kim Y-H, Yun B-S. Antioxidant polyphenols from the mycelial culture of the medicinal fungi Inonotus xeranticus and Phellinus linteus. J Appl Microbiol. 2008;104:1824–32.

    Article  CAS  PubMed  Google Scholar 

  9. Lee I-K, Seo G-S, Jeon NB, Kang HW, Yun BS. Phellinins A1 and A2, new styrylpyrones from the culture broth of Phellinus sp. KACC93057P: I. Fermentation, taxonomy, isolation and biological properties. J Antibiot. 2009;62:631–4.

    Article  CAS  Google Scholar 

  10. Han J-J, Bao L, He L-W, Zhang X-Q, Yang X-L, Li S-J, et al. Phaeolschidins A–E, five hispidin derivatives with antioxidant activity from the fruiting body of Phaeolus schweinitzii collected in the Tibetan Plateau. J Nat Prod. 2013;76:1448–53.

    Article  CAS  PubMed  Google Scholar 

  11. Olennikov DN, Gornostai TG, Penzina TA. Rheadinin, a new bis(styrylpyrone) from mycelium of Inonotus rheades. Chem Nat Compd. 2017;53:629–31.

    Article  CAS  Google Scholar 

  12. Parejo I, Petrakis C, Kefalas P. A transition metal enhanced luminol chemiluminescence in the presence of a chelator. J Pharm Toxicol Methods. 2000;43:183–90.

    Article  CAS  Google Scholar 

  13. Aruoma OI, Halliwell B, Gajewski E, Dizdaroglu M. Copper-ion-dependent damage to the bases in DNA in the presence of hydrogen peroxide. Biochem J. 1991;273:601–4.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Bouayed J, Bohn T. Exogenous antioxidants—double-edged swords in cellular redox state: health beneficial effects at physiologic doses versus deleterious effects at high doses. Oxid Med Cell Longev. 2010;3:228–37.

    Article  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgements

This work was supported in part by President’s Fund Initiative 2020 (Science for Local Community) at Toyama Prefectural University.

Author information

Authors and Affiliations

  1. Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan

    Naoya Oku, Rie Netsu & Yasuhiro Igarashi

  2. Department of Bioscience and Biotechnology, Fukui Prefectural University, Eiheiji-cho, Fukui, 910-1195, Japan

    Yoichi Kurokawa

Authors
  1. Naoya Oku
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rie Netsu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yoichi Kurokawa
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yasuhiro Igarashi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Naoya Oku.

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

41429_2023_599_MOESM1_ESM.docx

Supporting Information for: Phaeolschidin F, a new symmetrical bis(styrylpyrone) derivative with redox-catalyzing activity from the mushroom <i>Gymnopilus aeruginosus</i> (order <i>Agaricales</i>)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Oku, N., Netsu, R., Kurokawa, Y. et al. Phaeolschidin F, a new symmetrical bis(styrylpyrone) derivative with redox-catalyzing activity from the mushroom Gymnopilus aeruginosus (order Agaricales). J Antibiot 76, 236–238 (2023). https://doi.org/10.1038/s41429-023-00599-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41429-023-00599-x

Search

Advanced search

Quick links