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

The Journal of Antibiotics volume 76, pages 384–391 (2023)Cite this article

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Abstract

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.

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Acknowledgements

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 (www.forte-science.co.jp) for English language editing.

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Author notes

  1. These authors contributed equally: Yoshihiro Watanabe, Emi Arakawa.

Authors and Affiliations

  1. Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan

    Yoshihiro Watanabe, Kenichi Nonaka, Akari Ikeda, Tomoyasu Hirose, Toshiaki Sunazuka, Rei Hokari, Aki Ishiyama & Masato Iwatsuki

  2. Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan

    Yoshihiro Watanabe, Emi Arakawa, Naozumi Kondo, Kenichi Nonaka, Akari Ikeda, Tomoyasu Hirose, Toshiaki Sunazuka, Rei Hokari, Aki Ishiyama & Masato Iwatsuki

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  1. Yoshihiro Watanabe
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  2. Emi Arakawa
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  3. Naozumi Kondo
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Correspondence to Aki Ishiyama or Masato Iwatsuki.

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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). https://doi.org/10.1038/s41429-023-00617-y

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  • DOI: https://doi.org/10.1038/s41429-023-00617-y

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