Identification of cis-2-butene-1,4-dial as a microsomal metabolite of furan.
The hepatocarcinogen furan is believed to be activated to the reactive aldehyde, cis-2-butene-1,4-dial, by microsomal enzymes. The rat liver microsomal metabolism of furan was examined in the presence of NADPH and semicarbazide. HPLC analysis of incubation mixtures revealed the formation of a metabolite that coeluted with standards for the bis-semicarbazone adduct of cis-2-butene-1,4-dial. The formation of this compound required the presence of NADPH, semicarbazide, and microsomes. Preparative isolation and chemical characterization of this metabolite confirmed the structural assignment. These data provide evidence that the reactive aldehyde, cis-2-butene-1,4-dial, is a major metabolic product of furan.
Chen
L J
LJ
Division of Chemical Carcinogenesis, American Health Foundation, Valhalla, New York 10595, USA.
Hecht
S S
SS
Peterson
L A
LA
D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism*; D000818:Animals; D002273:Carcinogens / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D005663:Furans / Q000378:metabolism*; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D009249:NADP / Q000378:metabolism; D051381:Rats; D011916:Rats, Inbred F344; D013056:Spectrophotometry, Ultraviolet
D000447:Aldehydes; D002273:Carcinogens; D005663:Furans; C015977:malealdehyde; D009249:NADP; D003577:Cytochrome P-450 Enzyme System