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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

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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.

Mushrooms are a prolific source of bioactive metabolites [1]. Gymnopilus aeruginosus, called magic blue gym in English and “midori-sugitake”, meaning green cedar mushroom in Japanese, belongs to the family Cortinariaceae and is widespread in northwest pacific coast including Japan, often found on decaying conifers. Although a bitter taste is known for this mushroom, only four metabolites, psilocybin [2], two gymnopilins A11 and A12, and gymnoprenol A11 [3] are known from this species.

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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 

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Acknowledgements

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

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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

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Correspondence to Naoya Oku.

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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>)

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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

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