Derivatives of Bile Pigments

Lightner, David A.

doi:10.1016/b978-0-12-220106-6.50015-2

Cited by 10 publications

(19 citation statements)

References 89 publications

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“…The Zn2+ complex revealed a strong green fluorescence with a maximum at 512 nm, which could be suppressed by adding HCI. All these characteristics are similar to those of standard urobilin (Royer et al, 1964;Lester & Schmid, 1965;Lester & Klein, 1966;Lightner, 1979;Stoll, 1982).…”

Section: Radioactivitysupporting

confidence: 61%

“…Extraction with chloroform led to a maximum at 495 nm. These absorption properties are characteristic for urobilin-i XIa (Lightner, 1979;Billing, 1986). Re-subjection of the isolated fraction to h.p.l.c.…”

Section: Radioactivitymentioning

confidence: 99%

“…Two systems of paper chromatography also showed that the isolated pigment had the same RF as urobilin-i (Table 2). Urobilin-i is a racemic mixture and can even contain four stereoisomeric forms (Lightner, 1979). …”

Section: Radioactivitymentioning

confidence: 99%

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Urobilinogen-i is a major derivative of bilirubin in bile of homozygous Gunn rats

Kotal

Fevery

1990

Biochemical Journal

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Gunn rats lack bilirubin UDP-glycosyltransferases, but diazo-negative derivatives of bilirubin have been described in their bile. In order to investigate this alternative disposal of bilirubin, crude bile samples from Gunn and Wistar rats were directly analysed by h.p.l.c. Besides bilirubin (in Gunn rats) or its glycosides (in Wistar rats), two major compounds were detected. A yellow one corresponded to the previously documented vitamin B-2 and was equally prominent in Gunn rats or Wistar-rat bile. The other compound was colourless, but on standing in contact with air it was spontaneously oxidized to a pinkish-yellow pigment. It was far more prominent in Gunn-rat bile. Analysis of bile obtained after intravenous injection of [14C]bilirubin to Gunn rats demonstrated that this compound was highly labelled. Freezing and thawing of the bile resulted in the formation of a series of diazo-negative derivatives, demonstrating that the original compound was quite labile. Spectral (adsorption and fluorescent) and chromatographic (h.p.l.c., t.l.c. and paper chromatography) analysis of the oxidized form of the labelled compound allowed its identification as urobilin-i. The colourless compound secreted in bile was urobilinogen-i. Administration of neomycin and bacitracin to Gunn rats or gut resection suppressed the biliary excretion of urobilinogen and thus confirmed its intestinal origin. Urobilinogen seems thus to represent the major bilirubin derivative present in Gunn-rat bile. Its breakdown products might represent the so-far-unidentified diazo-negative polar bilirubin derivatives. Since only a small amount of bilirubin is present in Gunn-rat bile, the urobilinogen formed in the intestinal lumen seems to be derived from bilirubin reaching the gut via routes other than the biliary one.

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Section: Radioactivitysupporting

confidence: 61%

Section: Radioactivitymentioning

confidence: 99%

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Urobilinogen-i is a major derivative of bilirubin in bile of homozygous Gunn rats

Kotal

Fevery

1990

Biochemical Journal

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“…This system is distinct from the heme-oxygenase catabolism of heme, and bile pigments are not intermediates in this pathway. Propentdyopents have been found in gallstones and urine, and this mode of heme catabolism has been suggested (29) to be operative at low levels in normal metabolic states. Therefore, these products as well as the bile pigments must be considered as candidates for HDA.…”

Section: Discussionmentioning

confidence: 99%

Hematin-derived anticoagulant. Generation in vitro and in vivo.

Jones¹

1986

The Journal of Experimental Medicine

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Metalloporphyrins not only participate in a wide range of essential biochemical reactions, but have also recently received attention as therapeutic agents. Hematoporphyrins, which produce photodynamic destructive effects on cells are under investigation as antineoplastic agents (1, 2). Tin-protoporphyrin IX, a metal substitution of heme, potently inhibits heme-oxygenase and has been suggested in the treatment of hyperbilirubinemia (3-5). And, because heine (ferriprotoporphrin IX) suppresses b-aminolevulinic acid synthetase, hematin (ferriprotoporphyrin IX hydroxide) is being used to prevent or abate the painful crises of patients wth acute intermittent porphyria (ALP) 1 (6-8).Although the overall toxicity of hematin infusions appears to be minimal, profound effects on the routine tests of blood coagulation have recently been reported (9-1 1). Decreased platelet count and fibrinogen concentration, and prolonged thrombin (TT), prothrombin (PT), and activated partial thromboplastin (APTT) times are reported in a picture that mimicks diffuse intravascular coagulation. This study focuses on the mechanism of the fluid phase coagulation defect produced by hematin. The results indicate that, in vitro and in vivo, hematin is oxidatively degraded or metabolized to an anticoagulant, and that hematin itself is not responsible for the prolongation of clotting times. The results also suggest that this anticoagulant is a single derivative of hematin that binds to clotting proteins to reversibly inhibit their function, and which involves iron in its mechanism of action. Materials and MethodsHematin. Hematin was prepared by two methods. (a) Heroin, assayed 101% purity by pyridine hemochromogen, (Porphyrin Products, Logan, UT) was dissolved in 1 N NaOH (0.2 ml for each milliliter of hematin solution), then 0.8 ml of potassium phosphate buffer (pH 7.5) was added. The final pH, 7.5, was adjusted with 1 N HCI. (b) Hemin was dissolved in 1 N sodium carbonate (pH 12). The final pH of 7.5 was obtained by adding 1 N HC1. Tin-protoporphyrin IX, and protoporphyrin IX (Porphyrin Products) were prepared as per preparation (a) for hematin. The final concentration for all porphyrin solutions was 10 mg/ml. Hematin concentrations were confirmed by the pyridine hemo-

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“…1-9). As side chains or 1&carbon ring substituents, all bile pigments described thus far have four methyl groups, two propionic acid groups, and two vinyl groups, one or both of which can be isomerized to ethylidene (4, 10, 11) or reduced to ethyl (6,10,11). These substituents are arranged in the sequence found in protoporphyrin IX; in fact, all these bile pigments are formed from protoheme (8,(12)(13)(14), whose oxidative breakdown to biliverdin is catalyzed by the enzyme heme oxygenase (15-17).…”

mentioning

confidence: 99%

Bactobilin: blue bile pigment isolated from Clostridium tetanomorphum.

Brumm¹,

Fried²,

Friedmann³

1983

Proc. Natl. Acad. Sci. U.S.A.

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A blue bile pigment, possessing four acetic and four propionic acid side chains has been isolated from extracts of the anaerobic microorganism Clostridium tetanomorphum and in smaller amounts from Propionibacterium shermanii. The compound could be prepared in larger amounts by incubation of C. tetanomorphum enzyme extracts with added 8-aminolevulinic acid. The ultraviolet-visible, infrared, and proton magnetic resonance spectra of the pigment indicate a chromophore of the biliverdin type. Field-desorption mass spectrometry of the purified methyl ester showed a strong molecular ion at m/e = 962. This corresponds to the molecular weight expected for the octamethyl ester of a bilatriene type of bile pigment structurally derived from uroporphyrin 1m or I. Of the five possible structures, two could be eliminated by proton magnetic resonance spectroscopy. The name bactobilin is proposed for this previously unreported bile pigment.The open-chain tetrapyrrole compounds known as bile pigments are widely distributed. They are found free or bound to protein in mammals, birds, amphibians, reptiles, fish, molluscs, and insects and in algae and higher plants (for reviews, see refs. 1-9). As side chains or 1&carbon ring substituents, all bile pigments described thus far have four methyl groups, two propionic acid groups, and two vinyl groups, one or both of which can be isomerized to ethylidene (4, 10, 11) or reduced to ethyl (6,10,11). These substituents are arranged in the sequence found in protoporphyrin IX; in fact, all these bile pigments are formed from protoheme (8,(12)(13)(14), whose oxidative breakdown to biliverdin is catalyzed by the enzyme heme oxygenase (15-17). Bile pigments thus far have not been detected in prokaryotes. The present paper reports the isolation and in vitro formation of a bile pigment from the bacterium Clostridium tetanomorphum. This anaerobic organism makes uroporphyrinogen, the precursor of vitamin B-12, but not heme, protoporphyrinogen, or coproporphyrinogen. The isolated bile pigment is of interest not only because of its detection in a prokaryote, but also because its 13-carbon ring substituents, four acetic acid and four propionic acid groups, correspond to those of a uroporphyrin and not of protoporphyrin. MATERIALS AND METHODSSupplies. -Aminolevulinic acid was obtained from Sigma;biliverdin IXa dimethyl ester and the fully esterified methyl esters of uroporphyrin III, coproporphyrin III, protoporphyrin IX, and heptacarboxylporphyrin I, were from Porphyrin Products (Logan, UT). The n-hexane used for flash chromatography was "95 + %" (Aldrich), whereas the n-hexane for thin-layer chromatography was 99 mol % pure (Fisher). Other chemicals used were reagent grade or better. Silica gel for flash chromatography and a flash chromatography column, 3.4-cm diameter, were obtained from J. T. Baker. Whatman high-performance silica thin-layer chromatography plates with a preadsorbent spotting area (type LHP-K, 10 x 20 cm) and E. Merck precoated cellulose thin-layer chromatography plates were...

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Derivatives of Bile Pigments

Cited by 10 publications

References 89 publications

Urobilinogen-i is a major derivative of bilirubin in bile of homozygous Gunn rats

Urobilinogen-i is a major derivative of bilirubin in bile of homozygous Gunn rats

Hematin-derived anticoagulant. Generation in vitro and in vivo.

Bactobilin: blue bile pigment isolated from Clostridium tetanomorphum.

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