title: (8S)-(glutathion-S-yl)dihydromorphinone, a novel metabolite of morphine from guinea pig bile.
abstract: A novel glutathione-conjugated metabolite of morphine has been isolated from the bile of guinea pigs given morphine. The metabolite was separated by preparative HPLC on a reverse phase column (YMC-GEL C18) using methanol/water (1:4, v/v) as eluate and purified by HPLC on another reverse phase column (mu-Bondapak phenyl) using water/acetonitrile/trimethylamine/acetic acid (150:3:2:1, v/v) as a mobile phase. The unambiguous structure assignment of the metabolite was performed by fast atom bombardment mass spectrometry and 400 MHz fourier transform NMR spectrometric analysis, and it was identified as (8S)-glutathion-S-yl)dihydromorphinone, in comparison with the synthetic morphinone-glutathione adduct.
authors: Faculty of Pharmaceutical Sciences, Fukuoka University, Japan.
authors: T
authors: T
authors: Ishida
authors: Y
authors: Y
authors: Kumagai
authors: Y
authors: Y
authors: Ikeda
authors: K
authors: K
authors: Ito
authors: M
authors: M
authors: Yano
authors: S
authors: S
authors: Toki
authors: K
authors: K
authors: Mihashi
authors: T
authors: T
authors: Fujioka
authors: Y
authors: Y
authors: Iwase
authors: S
authors: S
authors: Hachiyama
mesh_terms: D000818:Animals; D001646:Bile / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D005978:Glutathione / Q000031:analogs & derivatives* / Q000302:isolation & purification; D006168:Guinea Pigs; D004091:Hydromorphone / Q000031:analogs & derivatives* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry / Q000379:methods; D009020:Morphine / Q000378:metabolism*
chemical_list: C059852:(glutathion-S-yl)dihydromorphinone; D009020:Morphine; D005978:Glutathione; D004091:Hydromorphone