Metabolism of alkenebenzene derivatives in the rat. III. Elemicin and isoelemicin.
1. The metabolites of elemicin (3,4,5-trimethoxyallylbenzene) and isoelemicin (3,4,5-trimethoxypropenylbenzene) in the rat were identified by g.l.c.-mass spectrometry. 2. The major metabolic reactions of elemicin follow the cinnamoyl pathway or the epoxide-diol pathway. The former route gives 3-(3,4,5-trimethoxyphenyl)propionic acid and its glycine conjugate as major urinary metabolites, whereas 3-(3,4,5-trimethoxyphenyl)propane-1,2-diol is the most prominent metabolite of the latter route. Small amounts of the epoxide of the 3-O-demethylated derivative of elemicin were identified in the urine. 3. Isoelemicin was metabolized by both aforementioned pathways; the cinnamoyl pathway predominated and 3-(3,4,5-trimethoxyphenyl)propionic acid was the major urinary metabolite. 4. All of the acidic metabolites detected were C6--C3 derivatives and further oxidation to benzoic acid derivatives did not occur. 5. Most of the urinary metabolites were also found in the bile, but in different relative amounts.
D000818:Animals; D001646:Bile / Q000378:metabolism; D005978:Glutathione / Q000378:metabolism; D008099:Liver / Q000378:metabolism; D008297:Male; D011748:Pyrogallol / Q000031:analogs & derivatives* / Q000378:metabolism; D051381:Rats
D011748:Pyrogallol; C002135:elemicin; C026730:isoelemicin; D005978:Glutathione