Protopine alkaloids in horse urine.
Protopine was extracted from Fumaria officinalis and purified by column chromatography. Urine samples were collected from horses and a human volunteer that had been administered either F. officinalis or protopine free base. Plant and urine samples were acetylated and analysed by GCMS after solid-phase extraction (SPE). The urinary metabolites of protopine were identified as 4,6,7,13-tetrahydro-9,10-dihydroxy-5-methyl-benzo[e]-l,3-benzodioxolo [4,5-1][2] benzazecin-12(5H)-one, 4,6,7,13-tetrahydro-10-hydroxy-9-methoxy-5-methyl-benzo[e]-1,3-benzodioxolo[4,5-1][2] benzazecin-12(5H)-one and 4,6,7,13-tetrahydro-9-hydroxy-10-methoxy-5-methyl-benzo[e]-1,3-benzodioxolo[4,5-l][2] benzazecin-12(5H)-one, chelianthifoline, isochelianthifoline and 2-O-desmethylchelianthifoline. The metabolic formation of the tetrahydroprotoberberines by closure of the bridge across N5 and C13 is rate limited and protopine-like metabolites accumulate only when the route is overloaded. Metabolism was qualitatively similar in the horse and human.
Wynne
Paul M
PM
Racing Analytical Services Limited, 400 Epsom Road, Flemington, Vic. 3031, Australia. pwynne@sge.com
Vine
John H
JH
Amiet
R Gary
RG
D000818:Animals; D053119:Benzophenanthridines; D001600:Berberine Alkaloids / Q000652:urine*; D008401:Gas Chromatography-Mass Spectrometry; D006736:Horses
D053119:Benzophenanthridines; D001600:Berberine Alkaloids; C009093:protopine