(+)-Epogymnolactam, a novel autophagy inducer from mycelial culture of Gymnopus sp

Abstract

Mushrooms, including Ganoderma lucidum, have been used as a potential source of therapeutic compounds, and an autophagy inducer would be useful for treatment of diverse diseases in human. Reported here is a full account of screening, isolation, structural determination, and biological activity of an autophagy inducer, (+)-epogymnolactam (1) from a mycelial culture of a Gymnopus sp. strain. Its structure was elucidated by HR-ESI-MS, NMR, and its plus sign by specific rotation. It exists as a tautomeric mixture of 1a and 1b in MeOH. The major tautomer of 1 is (1R,5S)-4-butyl-4-hydroxy-3-aza-6-oxa-bicyclo[3.1.0]hexan-2-one (1a), and the minor tautomeric form is (2R,3S)-3-pentanoyloxirane-2-carboxamide (1b).

Keywords: (+)-Epogymnolactam; (1R,5S)-4-Butyl-4-hydroxy-3-aza-6-oxa-bicyclo[3.1.0]hexan-2-one; (2R,3S)-3-Pentanoyloxirane-2-carboxamide; Autophagy; Biologically active substance; Gymnopus sp.; Isolation; Mushroom.