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.
This is a preview of subscription content, access via your institution
Subscribe to this journal
Receive 12 print issues and online access
$259.00 per year
only $21.58 per issue
Rent or buy this article
Get just this article for as long as you need it
Prices may be subject to local taxes which are calculated during checkout
Katsumoto K. List of fungi recorded in Japan. Tokyo: The Kanto Branch of The Mycological Society of Japan; 2010.
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.
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.
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.
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.
Clericuzio M, Mella M, Vita-Finzi P, Zema M, Vidari G. Cucurbitane Triterpenoids from Leucopaxillus gentianeus. J Nat Prod. 2004;67:1823–28.
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.
Marner F-J, Kasel T. Biomimetic synthesis of the iridal skeleton. J Nat Prod. 1995;58:319–23.
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.
Nishitoba T. Kumiseibun. In: Mizuno T, Kawai M, editors. Kinoko-no-Kagaku, Seikagaku. Tokyo: Gakkai Shuppan Center; 1992. p. 157–60.
Kibby G. The genus Tricholoma in Britain. Field Mycol.2010;11:113–40.
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.
Conflict of interest
The authors declare that they have no conflict of interest.
Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
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). https://doi.org/10.1038/s41429-020-0338-x