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Wakodecaline C, new tetrahydrofuran-fused decalin metabolite isolated from fungus Pyrenochaetopsis sp. RK10-F058

The Journal of Antibiotics volume 76, pages 346–350 (2023)Cite this article

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Abstract

A new decalin-containing secondary metabolite, wakodecaline C, was isolated from a fungus Pyrenochaetopsis sp. RK10-F058 by screening structurally interesting metabolites based on LC/MS profiling. The structure including the absolute configuration was determined by a combination of spectroscopic methods including NMR and mass spectrometry, chemical reaction, and calculation of ECD spectra. Wakodecaline C has unique structural features containing a tetrahydrofuran-fused decalin skeleton and tetramic acid moiety, which are connected through a double bond. The compound showed moderate cytotoxicity against HL-60 cells and antimalarial activity against the Plasmodium falciparum 3D7 strain.

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Acknowledgements

We would like to thank Dr T. Nakamura at RIKEN for the measurement of HRESITOFMS and H. Aono at RIKEN for performing the activity tests. Computer calculations using Gaussian 16 were performed using HOKUSAI at RIKEN. This work was supported in part by JSPS KAKENHI (grant numbers 17K07784, 20K05858, 20K05872, and 21H04720).

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Author notes

  1. Yushi Futamura

    Present address: Waseda Research Institute for Science and Engineering, Waseda University, Tokyo, 169-8555, Japan

  2. Hiroyuki Osada

    Present address: Department of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, 422-8526, Japan

  3. These authors contributed equally: Toshihiko Nogawa, Naoki Kato

Authors and Affiliations

  1. Molecular Structure Characterization Unit, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan

    Toshihiko Nogawa & Hiroyuki Koshino

  2. Chemica Biology Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan

    Toshihiko Nogawa, Takeshi Shimizu, Akiko Okano, Yushi Futamura & Hiroyuki Osada

  3. Faculty of Agriculture, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka, 573-0101, Japan

    Naoki Kato

  4. Natural Product Biosynthesis Research Unit, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan

    Naoki Kato & Shunji Takahashi

Authors
  1. Toshihiko Nogawa
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  8. Hiroyuki Osada
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Correspondence to Naoki Kato.

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Nogawa, T., Kato, N., Shimizu, T. et al. Wakodecaline C, new tetrahydrofuran-fused decalin metabolite isolated from fungus Pyrenochaetopsis sp. RK10-F058. J Antibiot 76, 346–350 (2023). https://doi.org/10.1038/s41429-023-00613-2

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  • DOI: https://doi.org/10.1038/s41429-023-00613-2

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