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Structure revision of tricholomenyn B, an antimitotic geranylcyclohexenone rediscovered as a bitter and antibacterial substance, from a basidiomycete Tricholoma japonicum (Shiro-shimeji)

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Abstract

Tricholomenyn B, an antimitotic geranylcyclohexenone originally discovered from a basidiomycete Tricholoma acerbum, was isolated as a bitter and antibacterial constituent from fruiting bodies of T. japonicum. Careful comparison of NMR, MS, and other physicochemical properties of the isolated substance with the literature values revised a previously proposed macrolide structure 1 to a macrodiolide 2. Compound 2 was perceived bitter at a minimum dose of 37.5 μg, showed weak antimicrobial activity against Kocuria rhizophila and Staphylococcus aureus, and was marginally cytotoxic (IC50 2.6 µM) against P388 murine leukemia cells.

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Acknowledgements

This work was supported in part by the President’s Fund Initiative 2022 (Industry-Academia-Government Collaboration) at Toyama Prefectural University. MJN is a recipient of the Ministry of Culture, Sports, Science, and Technology (MEXT) Scholarship for Foreign Students. P388 cells were obtained from JCRB Cell Bank under accession code JCRB0017 (Lot. 06252002).

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

    Md. Julkar Nime, Yuna Oguri, Naoya Oku & Yasuhiro Igarashi

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  1. Md. Julkar Nime
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  2. Yuna Oguri
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Correspondence to Naoya Oku.

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Nime, M.J., Oguri, Y., Oku, N. et al. Structure revision of tricholomenyn B, an antimitotic geranylcyclohexenone rediscovered as a bitter and antibacterial substance, from a basidiomycete Tricholoma japonicum (Shiro-shimeji). J Antibiot (2024). https://doi.org/10.1038/s41429-024-00746-y

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