Identification of gymnopilin A10 as an antibacterial agent in Gymnopilus mushrooms and discovery of gymnoprenol B13 from the fruiting bodies of G. orientispectabilis

Swiezewska E, Danikiewicz W. Polyisoprenoids: structure, biosynthesis and function. Prog Lipid Res. 2005;44:235–58.

Article  CAS  PubMed  Google Scholar 

Thorn RG, Malloch DW, Saar I, Lamoureux Y, Nagasawa E, Redhead SA, et al. New species in the Gymnopilus junonius group (Basidiomycota: Agaricales). Botany. 2020;98:293–315.

Article  Google Scholar 

Nozoe S, Koike Y, Tsuji E, Kusano G, Seto H. Isolation and structure of gymnoprenols, a novel type of polyisoprenepolyols from Gymnopilus spectabilis. Tetrahedron Lett. 1983;24:1731–4.

Article  CAS  Google Scholar 

Nozoe S, Koike Y, Kusano G, Seto H. Structure of gymnopilin, a bitter principle of a hallucinogenic mushroom, Gymnopilus spectabilis. Tetrahedron Lett. 1983;24:1735–6.

Article  CAS  Google Scholar 

Aoyagi F, Maeno S, Okuno T, Matsumoto H, Ikura M, Hikichi K, et al. Gymnopilins, bitter principles of the big-laughter mushroom Gymnopilus spectabilis. Tetrahedron Lett. 1983;24:1991–4.

Article  CAS  Google Scholar 

Nozoe S, Koike Y, Kusano G. Absolute stereochemistry of the triol moiety of gymnoprenols. Tetrahedron Lett. 1984;25:1371–2.

Article  CAS  Google Scholar 

Hanson RM. Absolute stereochemistry of the triol moiety of gymnoprenols: a reinvestigation. Tetrahedron Lett. 1984;25:3783–6.

Article  CAS  Google Scholar 

Nozoe S, Koike Y, Tsuji E, Kusano G. Revision of the absolute configuration of triol moiety of gymnoprenol. Tetrahedron Lett. 1984;25:4023–4.

Article  CAS  Google Scholar 

Nozoe S, Koike Y, Ito N, Kusano G. Isolation and structure of gymnoprenol-D, a homologus series of fully hydrated polyisoprenepolyol from Gymnopilus spectabilis. Chem Lett. 1984;13:1001–2.

Article  Google Scholar 

Findlay JA, He Z-Q. Minor constituents of Gymnopilus spectabilis. J Nat Prod. 1991;54:184–9.

Article  CAS  Google Scholar 

Tanaka M, Hashimoto K, Okuno T, Shirahama H. Neurotoxic oligoisoprenoids of the hallucinogenic mushroom, Gymnopilus spectabilis. Phytochemistry. 1993;34:661–4.

Article  CAS  Google Scholar 

Kim KH, Choi SU, Lee KR. Gymnopilin K: a new cytotoxic gymnopilin from Gymnopilus spectabilis. J Antibiot. 2011;65:135–7.

Article  Google Scholar 

Ohta T, Aizawa K, Kamo S, Tabei N, Oshima Y, Nozoe S. Stereochemistry of polyisoprenepolyols isolated from fungi genus Gymnopilus. Symp Chem Nat Prod. 1996;38:307–2.

Google Scholar 

Tomoda H, Huang XH, Nishida H, Masuma R, Kim YK, Omura S. Glisoprenins, new inhibitors of acyl-CoA: cholesterol acyltransferase produced by Gliocladium sp. FO-1513. 1. Production, isolation and physico-chemical and biological properties. J Antibiot. 1992;45:1202–6.

Article  CAS  Google Scholar 

Nishida H, Huang X-H, Tomoda H. Ōmura S. Glisoprenins, new inhibitors of acyl-CoA: cholesterol acyltransferase produced by Gliocladium sp. FO-1513. II. Structure elucidation of glisoprenins A and B. J Antibiot. 1992;45:1669–76.

Article  CAS  Google Scholar 

Thines E, Eilbet F, Anke H, Sterner O. Glisoprenins C, D and E, new inhibitors of appressorium formation in Magnaporthe grisea, from cultures of Gliocladium roseum. 1. Production and biological activities. J Antibiot. 1998;51:117–22.

Article  CAS  Google Scholar 

Sterner O, Thines E, Eilbet F, Anke H. Glisoprenins C, D and E, new inhibitors of appressorium formation in Magnaporthe grisea, from cultures of Gliocladium roseum. 2. Structure determination. J Antibiot. 1998;51:228–31.

Article  CAS  Google Scholar 

Joshi BK, Gloer JB, Wicklow DT. New verticillin and glisoprenin A analogues from Gliocladium catenulatum, a Mycoparasite of Aspergillus flavus Sclerotia. J Nat Prod. 1999;62:730–3.

Article  CAS  PubMed  Google Scholar 

Hegde VR, Dai P, Chu M, Patel M, Bryant R, Terracciano J, et al. Neurokinin receptor inhibitors: fermentation, isolation, physico-chemical properties, structure and biological activity. J Antibiot. 1997;50:983–91.

Article  CAS  Google Scholar 

Sawabe A, Morita M, Kiso T, Kishine H, Ohtsubo Y, Ouchi S, et al. Structural analysis of a precursory substance of bitterness: new polyisoprenepolyols isolated from an edible mushroom (Hypsizigus marmoreus) by fast atom bombardment mass spectrometry. J Agric Food Chem. 1999;47:588–93.

Article  CAS  PubMed  Google Scholar 

Sawabe A, Morita M, Ouchi S, Okamoto T. Structural characterization of a precursory substance of bitterness, new polyisoprenepolyols isolated from an edible mushroom by FAB/MS. Bull Inst Compr Agr Sci Kinki Univ. 2001;9:97–105.

CAS  Google Scholar 

Aoki S, Aboshi T, Onodera T, Kimura KI, Arai D, Iizuka Y, et al. Omphaloprenol A: a new bioactive polyisoprenepolyol isolated from the mycelium of poisonous mushroom Omphalotus japnonicus. Biosci Biotechnol Biochem. 2021;85:1364–70.

Article  PubMed  Google Scholar 

Sivasankarreddy K, Joseph J, PP T, K p, Thayyil P, Mathew D, et al. An insight into bacterial wilt of eggplant—a review. Trop Plant Pathol. 2024;49:746–64.

Article  Google Scholar 

Smith AH. Mushrooms in their natural habitats. Sawyer's Inc. Portland, Oregon, USA.1949; p. 626.

Orton PD. New check list of British agarics and boleti. Trans Brit Mycol Soc. 1960;43:159–439.

Article  Google Scholar 

Kurono G, Sakai T, Tochiori K. Studies on the Culture of Pholiota spectabilis Fr. (Japanese big laughing toadstool). Kanazawa-Daigaku-Yakugakubu-Kenkyu-Nempo (Ann Rep Fac Pharm Kanazawa Univ). 1956;6:1–23 (in Japanese). https://kanazawa-u.repo.nii.ac.jp/records/25780.

Kusano G, Koike Y, Inoue H, Nozoe T. The constituents of Gymnopilus spectabilis. Chem Pharm Bull. 1986;34:3465–70.

Article  CAS  Google Scholar 

Lee IK, Cho SM, Seok SJ, Yun BS. Chemical constituents of Gymnopilus spectabilis and their antioxidant activity. Mycobiology. 2008;36:55–9.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Jung B, Heo EJ, Nguyen DL, Youn UJ, Kim KH, Son B, et al. Antimicrobial steroids from poisonous mushroom Gymnopilus orientispectabilis and their molecular docking studies. Separations. 2025;12:23.

Article  CAS  Google Scholar 

Núñez-Alarcón J, Paredes JC, Carmona MT, Quiñones M. Ostopanic acid, a cytotoxic fatty acid from Gymnopilus spectabilis. Bol Soc Chil Quim. 2000;46:227–9.

Google Scholar 

Lee S, Ryoo R, Choi JH, Kim JH, Kim SH, Kim KH. Trichothecene and tremulane sesquiterpenes from a hallucinogenic mushroom Gymnopilus junonius and their cytotoxicity. Arch Pharm Res. 2020;43:214–23.

Article  CAS  PubMed  Google Scholar 

Lee S, Kim CS, Yu JS, Kang H, Yoo MJ, Youn UJ, et al. Ergopyrone, a styrylpyrone-fused steroid with a hexacyclic 6/5/6/6/6/5 skeleton from a mushroom Gymnopilus orientispectabilis. Org Lett. 2021;23:3315–9.

Article  CAS  PubMed  Google Scholar 

Lee S, Jang M, Ryoo R, Roh J, Ko SK, Kim KH. New autophagy-modulating lanostane-type triterpenoids from a hallucinogenic poisonous mushroom Gymnopilus orientispectabilis. Arch Pharm Res. 2024;47:272–87.

Article  CAS  PubMed  Google Scholar 

Didloff J, Boukes GJ, Nyambe MN, Beukes DR, Lerata MS, Vilane V, et al. Exploring antimycobacterial potential: safety evaluation and active compound isolation from Gymnopilus junonius. Antibiotics. 2025;14:79.

Article  Google Scholar 

Oku N, Netsu R, Kurokawa Y, Igarashi Y, Phaeolschidin F, a new symmetrical bis(styrylpyrone) derivative with redox-catalyzing activity from the mushroom Gymnopilus aeruginosus (order Agaricales). J Antibiot. 2023;76:236–8.

Article  CAS  Google Scholar 

Harigaya H. Studies on the stereochemistry of gymnopilins, the poisonous principles of Gymnopilus spectabilis. Ph.D. Dissertation, Hokkaido University, 1994. https://eprints.lib.hokudai.ac.jp/dspace/handle/2115/51267.

Hossain TJ. Methods for screening and evaluation of antibacterial activity: a review of protocols, advantages, and limitation. Eur J Microbiol Immunol. 2024;14:97–115.

Article  CAS  Google Scholar 

Oku N, Matsumoto M, Yonejima K, Tansei K, Igarashi Y. Sacrolide A, a new antimicrobial and cytotoxic oxylipin macrolide from the edible cyanobacterium Aphanothece sacrum. Beilstein J Org Chem. 2014;10:1808–16.

Article  PubMed  PubMed Central  Google Scholar 

Comments (0)

No login
gif