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The Isolation of Crystalline i-Urobilinogen (Mesobilirubinogen) from Feces

COMPARISON WITH CRYSTALLINE d-UROBILINOGEN (H₄₄) AND SEPARATION OF NATURAL i-UROBILIN INTO OPTICALLY ACTIVE COMPONENTS

From the ¹ From the Departments of Medicine and Chemistry, University of Minnesota, Minneapolis, Minnesota 55455

Crystalline i-urobilinogen has been isolated from the feces of two individuals at appropriate intervals after discontinuance of tetracycline. The crystals from the first case were completely separated from dihydromesobilirubin and were highly similar to synthetic mesobilirubinogen in respect to a number of physical properties. Both are optically inactive from 600 to 200 mµ. A dextrorotatory component of the i-urobilin, formed by simple dehydrogenation of the recrystallized i-urobilinogen, separated by crystallization, leaving an l component in the mother liquor.

The i-urobilinogen crystallized from the feces of the second case, although having the same crystal habit as synthetic mesobilirubinogen, could not be separated entirely from dihydromesobilirubin. Nevertheless the crystalline i-urobilin prepared after oxidative elimination of dihydromesobilirubin separated into optically active components, although this separation was less complete, even on recrystallization, than with the urobilin from the first case. Possible reasons for this difference and for the greater difficulty in resolving synthetic i-urobilin are discussed.

Crystalline d-urobilinogen (H₄₄) was prepared by catalytic hydrogenation of d-urobilinogen from feces. This is readily distinguished, on the basis of several physical properties, from i-urobilin or synthetic mesobilirubinogen. The d-urobilin (H₄₂) prepared from it was identical in respect to a number of physical properties with d-urobilin obtained from i-urobilin.

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