Isolation and Identification of the Urinary Pigment Uroerythrin

Abstract

The red pigment uroerythrin, a chromophore known to be adsorbed by the amorphous urate sediments (sedimentum lateritium), has been isolated from human urine and further purified as its trimethyl derivative.Urine was applied to a column of Amberlite XAD-2 resin on which uroerythrin and other pigments were adsorbed. The pigments were eluted with methanol and uroerythrin was further purified by extraction with ether at pH 4.0, repeated chromatography on lipophilic Sephadex LH-20 and thin-layer chromatography on silica gel. For optimal purification uroerythrin was converted into the trimethyl derivative and chromatographed on silica gel thin-layer plates.The structure of the pigment has been studied by chromate degradation followed by identification of the imide products by thin-layer chromatography. From these results and from infrared, mass spectral and nuclear magnetic resonance data a tripyrrole structure for uroerythrin is concluded. The proposed structure for the chromophore is related to that of the bile pigment biliverdin consisting, however, only of the rings A, B and C.

Intermolecularly hydrogen-bonded dimeric helices: tripyrrindiones

“…The bathochromic shift, blue coloration and absence of fluorescence upon addition of Zn(OAc) 2 are qualitatively similar to those found from 1 in DBU. The shift to yellow and strong fluorescence upon addition of NH 4 OH to the solution is again similar. However, attempts to isolate the Zn salt or its product following addition of NH 4 OH have been unsuccessful.…”

“…1D. 4 Apparently only the endo-vinyl isomer was isolated, and the E-stereochemistry was indicated throughout. Whether the predictably less stable exo-vinyl isomer was present is unclear.…”

Bilirubin Oxidation Provoked by Endotoxins Treatment is Suppressed by Feeding Ascorbic Acid in a Rat Mutant Unable to Synthesize Ascorbic Acid

“…We infer that the oxidative stress caused by LPS treatment did not induce further heme oxygenase-1 production in the spleen, because heme oxygenase-I is steadily produced in the spleen and heme oxygenase-1 is a predominant isozyme of heme oxygenase in the spleen (i.e. heme oxygenase-2 production is very small in the spleen) (Figs 4 b and 5 b) (Braggins et al, 1986).…”

“…These bilirubin oxidative metabolites (BOM) in urine were found to increase in a patient who had undergone laparotomy that had taken a long time (Yamaguchi et al, 1994b). This result suggests that bilirubin is oxidized more by reactive oxygen species produced during laparotomy and has a protective effect against oxidative stress in viva Heme oxygenase, a rate-limiting enzyme of bilirubin biosynthesis, comprises two isozymes (Braggins et al, 1986;Trakshel and Maines, 1989;Trakshel et al, 1991;Cruse and Maines, 1988), heme oxygenase-1 (inducible) and heme oxygenase-2 (constitutive). Heme oxygenase-1 activity is significantly increased by heme, endotoxin (lipopolysaccharide, LPS), heavy metals, heat shock, interleukin-I , and hydrogen peroxide (Taketani et al, 1989;Keyse and Tyrrell, 1989;Vile and Tyrrell, 1993;Tomaro et al, 1991).…”

Basic Anatomy, Physiology, and Husbandry

“…Whereas the fractional excretion of calcium in most mammals is less than 2%, the range for rabbits is 45% to 60%. 73 Uroerythrin is a breakdown product or a precursor of heme 7 and is related to the bile pigment biliverdin. 12-5).…”