title: (+)-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).
authors.affiliation: Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University, Kita-9, Nishi-9, Kita-ku, Sapporo 060-8589, Japan.
authors.forename: Shinya
authors.initials: S
authors.lastname: Mitsuhashi
authors.affiliation: Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University, Kita-9, Nishi-9, Kita-ku, Sapporo 060-8589, Japan.
authors.forename: Chihaya
authors.initials: C
authors.lastname: Shindo
authors.affiliation: Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University, Kita-9, Nishi-9, Kita-ku, Sapporo 060-8589, Japan.
authors.forename: Kengo
authors.initials: K
authors.lastname: Shigetomi
authors.affiliation: Division of Environmental Resources, Research Faculty of Agriculture, Hokkaido University, Kita-9, Nishi-9, Kita-ku, Sapporo 060-8589, Japan.
authors.forename: Toshizumi
authors.initials: T
authors.lastname: Miyamoto
authors.affiliation: Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University, Kita-9, Nishi-9, Kita-ku, Sapporo 060-8589, Japan. Electronic address: m-ub@for.agr.hokudai.ac.jp.
authors.forename: Makoto
authors.initials: M
authors.lastname: Ubukata
mesh_terms: D000363:Agaricales / Q000737:chemistry*; D001343:Autophagy / Q000187:drug effects*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry / Q000302:isolation & purification*; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; C000604134:epogymnolactam
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