Isolation and characterization of a new thio-glucuronide, a biliary metabolite of malotilate in rats.
1. The metabolism of malotilate, possessing a 1,3-dithiole ring, was studied in rats. A major biliary metabolite of malotilate was isolated and determined to be a thio-glucuronide of the dithiol formed by ring-opening, namely, 1-mercapto-2,2-di(isopropoxycarbonyl)-ethenyl 1-thio-beta-D-glucosiduronic acid. The structure was elucidated by proton-n.m.r., 13C-n.m.r. and high-resolution mass spectrometry. 2. The thio-glucuronide was completely hydrolysed by beta-glucuronidase. This enzymic reaction was inhibited by saccharo-1,4-lactone.
Nakaoka
M
M
Research Institute, Daiichi Seiyaku Co., Ltd., Tokyo, Japan.
Hakusui
H
H
Takegoshi
T
T
D000818:Animals; D001652:Bile Ducts / Q000378:metabolism; D002250:Carbon Radioisotopes; D002404:Catheterization; D002850:Chromatography, Gel; D005965:Glucuronates / Q000302:isolation & purification*; D005966:Glucuronidase; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008314:Malonates / Q000378:metabolism*; D013058:Mass Spectrometry; D051381:Rats; D011919:Rats, Inbred Strains
D002250:Carbon Radioisotopes; D005965:Glucuronates; D008314:Malonates; C059669:1-mercapto-2,2-di-(isopropoxycarbonyl)ethenyl-1-thioglucosiduronic acid; D005966:Glucuronidase; C024808:diisopropyl 1,3-dithiol-2-ylidenemalonate