Citation

Lee S, Jang M, Ryoo R, Roh J, Ko SK, Kim KH. Arch. Pharm. Res. 2024; ePub(ePub): ePub.

Copyright

(Copyright © 2024, Pharmaceutical Society of Korea, Publisher Holtzbrinck Springer Nature Publishing Group)

DOI

10.1007/s12272-024-01486-1

PMID

38416389

Abstract

Gymnopilus orientispectabilis, also known as "big laughter mushroom," is a hallucinogenic poisonous mushroom that causes excessive laughter upon ingestion. From the fruiting bodies of G. orientispectabilis, eight lanostane-type triterpenoids (1-8), including seven novel compounds: gymnojunols A-G (2-8), were isolated. The chemical structures of these new compounds (2-8) were determined by analyzing their 1D and 2D NMR spectra and HR-EISMS, and their absolute configurations were unambiguously assigned by quantum chemical ECD calculations and a computational method coupled with a statistical procedure (DP4+). Upon evaluating autophagic activity, compounds 2, 6, and 7 increased LC3B-II levels in HeLa cells to a similar extent as bafilomycin, an autophagy inhibitor. In contrast, compound 8 decreased the levels of both LC3B-I and LC3B-II, and a similar effect was observed following treatment with rapamycin, an autophagy inducer. Our findings provide experimental evidence for new potential autophagy modulators in the hallucinogenic poisonous mushroom G. orientispectabilis.

Language: en

Keywords

Autophagic activity; ECD calculation; Gymnopilus orientispectabilis; Lanostane-type triterpenoids; Structural elucidation