Disturbance of bilirubin metabolism in the intestine in liver diseases was investigated from the oxidation products of mesobilirubinogen. Feces were obtained from five normal subjects, five cases with chronic hepatitis, five cases with liver cirrhosis and three cases with hemolytic jaundice. The oxidation products of mesobilirubinogen were prepared by Stoll's thin layer chromatography after extraction procedure from feces by Watson. The oxidation products were divided into two groups, verdins (glaucobilins) and violins (mesobiliviolins). The verdins were identified by nuclear magnetic resonance (NMR) spectra and mass spectrometry as glaucobilin isomers. The results were as follows; 1) Glaucobilin Ⅲα, Ⅸα and ⅩⅢα dimethylester were separated by thin layer chromatography and identified with NMR spectra and mass spectrometry. 2) Significant correlation between the appearance of glaucobilin isomers and the amount of urobilinogen extracted from feces in liver diseases. 3) Using ten grams of feces, glaucobilin Ⅸα was found in two out of five normal subjects, in two cases with chronic viral hepatitis, in four cases with liver cirrhosis and in all cases with hemolytic jaundice. Glaucobilin Ⅲα was detected only in all cases with hemolytic jaundice, and glaucobilin ⅩⅢα was positive in a case with liver cirrhosis, and in all cases with hemolytic jaundice. 4) According to these results, it became clear that not only Ⅸα type but Ⅲα, ⅩⅢα type of bilirubinoid were contained in the human feces. 5) Absorption maxima of glaucobilin Ⅲα, Ⅸα and ⅩⅢα were found at 630nm, 630.5nm and 637nm, and the dimethylester of them were at 630.5nm, 633.5nm and 636nm respectively in methanolic solution at pH 6.0. After acidification with hydrochloric acid into pH 1.0, absorption maxima of them were moved to longer wave length. These maxima were 681.5nm, 682nm and 682.5nm
in free type in the order of glaucobilin Ⅲα, Ⅸα and ⅩⅢα. 6) Significant correlations between the amount of glaucobilin Ⅸα dimethylester and ZTT or γ-globulin were found. And it was reaffirmed that the appearance of fecal glaucobnin Ⅸα and mesobiliviolin Ⅸα in various liver diseases were important items to determine the degree of the liver parenchymal damage.