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Bitter compounds in two Tricholoma species, T. aestuans and T. virgatum


Lascivol was identified as the bitter compound in two Tricholoma species, T. aestuans and T. virgatum, and was previously isolated from the European mushroom T. lascivum. The structure of lascivol was previously solved by X-ray crystallographical analysis but its stereochemistry at C3 remained ambiguous. We thus re-examined the absolute configuration of C3 bearing a hydroxy group using the modified Mosher’s method.

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  1. Katsumoto K. List of fungi recorded in Japan. Tokyo: The Kanto Branch of The Mycological Society of Japan; 2010.

    Google Scholar 

  2. Eizenhoefer T, Fugmann B, Sheldrick WS, Steffan B, Steglich W. Lascivol, der Bitterstoff des Unterschaemten Ritterlings, Tricholoma lascivum (Agaricales). Liebigs, Ann Chem. 1990;1115–18.

  3. Ohtani I, Kusumi T, Kashman Y, Kakisawa H. High-field FT NMR application of Mosher’s method. The absolute configurations of marine terpenoids. J Am Chem Soc. 1991;113:4092–96.

    Article  CAS  Google Scholar 

  4. Qiu W, Kobori H, Wu J, Choi J-H, Hirai H, Kawagishi H. Plant growth regulators from the fruiting bodies of Tricholoma flavovirens. Biosci Biotechnol Biochem. 2017;81:441–44.

    Article  CAS  Google Scholar 

  5. Garlaschelli L, Pang Z, Sterner O, Vidari G. New indole derivatives from the fruit bodies of Tricholoma sciodes and T. virgatum. Tetrahedron. 1994;50:3571–4.

    Article  CAS  Google Scholar 

  6. Clericuzio M, Mella M, Vita-Finzi P, Zema M, Vidari G. Cucurbitane Triterpenoids from Leucopaxillus gentianeus. J Nat Prod. 2004;67:1823–28.

    Article  CAS  Google Scholar 

  7. Hellwig V, Dasenbrock J, Graef C, Kahner L, Schumann S, Steglich W. Calopins and cyclocalopins—bitter principles from Boletus calopus and related mushrooms. Eur J Org Chem. 2002;2895–904.

  8. Marner F-J, Kasel T. Biomimetic synthesis of the iridal skeleton. J Nat Prod. 1995;58:319–23.

    Article  CAS  Google Scholar 

  9. Steglich W, Kopanski L, Wolf M, Moser M, Tegtmeyer G. Indole alkaloids from the gilled agaric Cortinarius infractus (Agaricals). Tetrahedron Lett. 1984;25:2342–44.

    Article  Google Scholar 

  10. Nishitoba T. Kumiseibun. In: Mizuno T, Kawai M, editors. Kinoko-no-Kagaku, Seikagaku. Tokyo: Gakkai Shuppan Center; 1992. p. 157–60.

    Google Scholar 

  11. Kibby G. The genus Tricholoma in Britain. Field Mycol.2010;11:113–40.

    Article  Google Scholar 

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The authors thank to Mr. Makoto Hashiya, Dr. Katsuhiro Konno, Mr. Shigeo Morimoto, Mr. Yasukazu Ohkubo, Mr. Shigekazu Habu, Mr. Juichi Ooyama for their help in collecting the mushroom samples and identification of the species. This work was partly supported by KAKENHI (Grants-in-Aid for Challenging Exploratory Research; Grant Number JP25560409) from Japan Society for the Promotion of Science (JSPS) to KH and a Grant-in Aid for Scientific Research on Innovative Areas ‘.Frontier Research on Chemical Communications’ (No 117H06402) to HK.

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Correspondence to Kimiko Hashimoto.

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Oba, Y., Urai, M., Wu, J. et al. Bitter compounds in two Tricholoma species, T. aestuans and T. virgatum. J Antibiot 73, 697–701 (2020).

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