Skip to main content

Thank you for visiting 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.

New antimalarial fusarochromanone analogs produced by the fungal strain Fusarium sp. FKI-9521


Two new antimalarial compounds, named deacetyl fusarochromene (1) and 4′-O-acetyl fusarochromanone (2), were discovered from the static fungal cultured material of Fusarium sp. FKI-9521 isolated from feces of a stick insect (Ramulus mikado) together with three known compounds fusarochromanone (3), 3′-N-acetyl fusarochromanone (4), and 5 (fusarochromene or banchromene). The structures of 1 and 2 were elucidated as new analogs of 3 by MS and NMR analyses. The absolute configurations of 1, 2, and 4 were determined by chemical derivatization. All five compounds showed moderate in vitro antimalarial activity against chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains, with IC50 values ranging from 0.08 to 6.35 µM.

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

Access options

Rent or buy this article

Prices vary by article type



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

Fig. 1
Scheme 1
Fig. 2


  1. World Health Organization, World Malaria Report 2021.

  2. Hayashi Y, Fukasawa W, Hirose T, Iwatsuki M, Hokari R, Ishiyama A, et al. Kozupeptins, antimalarial agents produced by Paracamarosporium species: Isolation, structural elucidation, total synthesis, and bioactivity. Org Lett. 2019;21:2180–4.

    Article  CAS  PubMed  Google Scholar 

  3. Ishiyama A, Hokari R, Nonaka K, Chiba T, Miura H, Otoguro K, et al. Diatretol, an α, α’-dioxo-diketopiperazine, is a potent in vitro and in vivo antimalarial. J. Antibiot. 2021;74:266–8.

    Article  CAS  Google Scholar 

  4. Ouchi T, Watanabe Y, Nonaka K, Muramatsu R, Noguchi C, Tozawa M, et al. Clonocoprogens A, B and C, new antimalarial coprogens from the Okinawan fungus Clonostachys compactiuscula FKR-0021. J Antibiot. 2020;73:365–71.

    Article  CAS  Google Scholar 

  5. Watanabe Y, Hachiya K, Ikeda A, Nonaka K, Higo M, Muramatsu R, et al. Koshidacins A and B, antiplasmodial cyclic tetrapeptides from the Okinawan fungus Pochonia boninensis FKR-0564. J Nat Prod. 2022;85:2641–9.

    Article  CAS  PubMed  Google Scholar 

  6. Pathre SV, Gleason BW, Lee WY, Mirocha JC. The structure of fusarochromanone: new mycotoxin from Fusarium roseum, “Graminearum”. Can J Chem. 1986;64:1308–11.

    Article  CAS  Google Scholar 

  7. Takahama Y, Shibata Y, Tanaka K. Concise synthesis of fungal metabolite (+)-Fusarochromanone via Rhodium (III)-catalyzed oxidative sp2 C-H bond olefination. Chem Lett. 2016;45:1177–9.

    Article  CAS  Google Scholar 

  8. Marshall JW, Mattos-Shipley KMJ, Ghannam IAY, Munawar A, Killen JC, Lazarus CM, et al. Fusarochromene, a novel tryptophan-derived metabolite from Fusarium sacchari. Org Biomol Chem. 2021;19:182–7.

    Article  CAS  PubMed  Google Scholar 

  9. Michel DK, Ferdinand MT, Hamdi MD, Tofazzal I, Rainer BO, Hartmut L. Banchromene and other secondary metabolites from the endophytic fungus Fusarium sp. obtained from Piper guineense inhibit the motility of phytopathogenic Plasmopara viticola zoospores. Tet Lett. 2014;55:4057–61.

    Article  Google Scholar 

  10. Kondo N, Sakai K, Kimishima A, Hokari R, Honsho M, Sato M, et al. Confluenine G, a new compound from a basidiomycetous yeast Moesziomyces sp. FKI-9540 derived from the gut of a moth Acherontia lachesis (Lepidoptera, Sphingidae). Biosci Biotechnol Biochem. 2022;86:949–54.

    PubMed  Google Scholar 

  11. Nonaka K, Ōmura S, Masuma M, Kaifuchi S, Masuma R. Three new Pochonia taxa (Clavicipitaceae) from soils in Japan. Mycologia. 2013;105:1202–18.

    Article  PubMed  Google Scholar 

  12. Otoguro K, Ui H, Ishiyama A, Arai N, Kobayashi M, Takahashi Y, et al. In vitro antimalarial activities of the microbial metabolites. J Antibiot. 2003;56:322–4.

    Article  Google Scholar 

  13. Otoguro K, Kohana A, Manabe C, Ishiyama A, Ui H, Shiomi K, et al. Potent antimalarial activities of polyether antibiotic, X-206. J Antibiot. 2001;54:658–63.

    Article  CAS  Google Scholar 

  14. Altschul SF, Madden TL, Schaffer AA, Zhang J, Zhang Z, Miller W, et al. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res. 1997;25:3389–402.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Summerell BA, Rugg CA, Burgess LW. Characterization of Fusarium babinda sp. nov. Nycol Res. 1995;99:1345–8.

    Google Scholar 

  16. Fitch RW, Snuder BB, Zhou Q, Foxman BM, Pandya AA, Yakel JL, et al. Absolute configuration and pharmacology of the poison frog alkaloid phantasmidine. J. Nat. Prod. 2018;81:1029–35.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Fraselle JV. Experimental evidence of the pathogenicity of Fusarium oxysporum Schl. F. to the oil palm (Elaeis guineensis J.). Nature. 1951;167:447.

    Article  CAS  PubMed  Google Scholar 

  18. Ying G, Xin C, Chaowei S, Karnika S, Mansoureh B, Elahe M, et al. Fusarochromanone induces G1 cell cycle arrest and apoptosis in COS7 and HEK293 cells. PloS One. 2014;11:e112641.

    Google Scholar 

  19. Matthews H, Duffy CW, Merrick CJ. Checks and balances? DNA replication and the cell cycle in Plasmodium. Parasites Vectors. 2018;11:216.

    Article  PubMed  PubMed Central  Google Scholar 

Download references


We are grateful to Distinguished Emeritus Professor Satoshi Ōmura (Kitasato University) for his helpful support and valuable guidance and suggestions. We thank Dr. Kenichiro Nagai, Ms. Reiko Seki, and Ms. Noriko Sato (School of Pharmacy, Kitasato University) for various instrumental analyses. This research was partially supported by Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant Number JP21am0101096 (Phase I) and JP22ama121035 (Phase II). This work was supported by JSPS KAKENHI Grant Number JP20K07106. We would also like to thank FORTE ( for English language editing.

Author information

Authors and Affiliations


Corresponding authors

Correspondence to Aki Ishiyama or Masato Iwatsuki.

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

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and Permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Watanabe, Y., Arakawa, E., Kondo, N. et al. New antimalarial fusarochromanone analogs produced by the fungal strain Fusarium sp. FKI-9521. J Antibiot 76, 384–391 (2023).

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI:


Quick links