title: beta-Hydroxyergothioneine, a new ergothioneine derivative from the mushroom Lyophyllum connatum, and its protective activity against carbon tetrachloride-induced injury in primary culture hepatocytes.
abstract: A new ergothioneine derivative named beta-hydroxyergothioneine was isolated from the mushroom Lyophyllum connatum. Ergothioneine,N-hydroxy-N',N'-dimethylurea, and connatin (N-hydroxy-N',N'-dimethylcitrulline) were also isolated. All the compounds displayed the ability to scavenge free radicals, based on a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. Structural determination, including the absolute stereochemistry of beta-hydroxyergothioneine, was achieved by spectroscopic analysis and X-ray crystallography. The radical scavenging activity of beta-hydroxyergothioneine was almost the same as that of ergothioneine. beta-Hydroxyergothioneine showed the greatest protective activity against carbon tetrachloride-induced injury in primary culture hepatocytes.
authors.affiliation: Course of the Science of Bioresources, The United Graduate School of Agricultural Sciences, Iwate University (Yamagata University), Tsuruoka, Yamagata, Japan.
authors.forename: Chieko
authors.initials: C
authors.lastname: Kimura
authors.forename: Manabu
authors.initials: M
authors.lastname: Nukina
authors.forename: Kiharu
authors.initials: K
authors.lastname: Igarashi
authors.forename: Yoko
authors.initials: Y
authors.lastname: Sugawara
mesh_terms: D000363:Agaricales / Q000737:chemistry*; D000818:Animals; D001713:Biphenyl Compounds; D002251:Carbon Tetrachloride / Q000037:antagonists & inhibitors; D002478:Cells, Cultured; D004880:Ergothioneine / Q000031:analogs & derivatives* / Q000302:isolation & purification* / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000302:isolation & purification* / Q000494:pharmacology; D022781:Hepatocytes / Q000187:drug effects*; D006834:Hydrazines; D015394:Molecular Structure; D010851:Picrates; D051381:Rats; D017208:Rats, Wistar
chemical_list: D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D006834:Hydrazines; D010851:Picrates; C502048:beta-hydroxyergothioneine; D004880:Ergothioneine; D002251:Carbon Tetrachloride; C004931:1,1-diphenyl-2-picrylhydrazyl