Some observations concerning mammlian indoxyl metabolism and its relationship to the formation of urinary indigo pigments

Sapira, Joseph D.; Somani, Satu M.; Shapiro, Alvin P.; Scheib, Eileen T.; Reihl, William

doi:10.1016/0026-0495(71)90123-5

Cited by 21 publications

(16 citation statements)

References 22 publications

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“…This structure would suggest either a steroidal or bile acid conjugate. It is interesting to note that Sapira et al 6 also investigated a 2-year-olct girl with congenital adrenal hyperplasia who, after exposure to sunlight, produced blue diapers. It was postulated that the sunlight breaks the B-ring of 7-dehydrocholesterol to form vitamin 03 and by analogy could convert 0-5-pregnanetriol into a substance with a structure similar to vitamin 03.…”

Section: Discussionmentioning

confidence: 99%

Purple Urine Bag Syndrome

Stott

Roberts

et al. 1987

Ann Clin Biochem

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Purple pigment extracted from the urinary catheters and collecting bags of two elderly female patients was analysed by a variety of chemical techniques, including mass spectroscopy and nuclear magnetic resonance. Although previous studies identified the pigment as indigo, we failed to confirm this. Our analysis also demonstrated that indicanuria is not a requirement for the production of the pigment and furthermore indicates that the molecular structure of the pigment is either a steroidal or bile acid conjugate.

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Section: Discussionmentioning

confidence: 99%

Purple Urine Bag Syndrome

Stott

Roberts

et al. 1987

Ann Clin Biochem

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“…We measured the concentrations of indirubin and indigo in urine that was processed within 15 min after excretion to minimize the potential effects of bacterial action (21). Table I shows that indirubin and indigo are both normally present in human urine at average concentrations of ϳ0.2 nM.…”

Section: Indirubin As An Endogenous Ahr Ligand 31476mentioning

confidence: 99%

Indirubin and Indigo Are Potent Aryl Hydrocarbon Receptor Ligands Present in Human Urine

Adachi¹,

Mori²,

Matsui³

et al. 2001

Journal of Biological Chemistry

359

257

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Aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that regulates genes involved in xenobiotic metabolism, cellular proliferation, and differentiation. Numerous xenobiotic and biological compounds are known to interact with AhR, but it remains an orphan receptor, because its physiological ligand is unknown. We identified AhR ligands in human urine using a yeast AhR signaling assay and then characterized their properties. Two ligands, indirubin and indigo, were both present at average concentrations of ϳ0.2 nM in the urine of normal donors. Indirubin was also detected in fetal bovine serum and contributed half of the total AhR ligand activity. The activities of indirubin and indigo were comparable with or more potent than that of the archetypal ligand, 2,3,7,8-tetrachlorodibenzo-p-dioxin, in yeast AhR activation assays. We suggest that the endogenous levels and potencies of indirubin and indigo are such that they activate AhR-mediated signaling mechanisms in vivo. AhR,1 also called the dioxin receptor, is a ligand-activated transcription factor that is present in most cell and tissue types of the body (1). AhR-mediated signaling is required for potent xenobiotic ligands such as TCDD and polychlorinated biphenyls to produce toxic responses (2, 3). Toxic effects that are linked to xenobiotic AhR ligand exposures in animals include cancers, reproductive impairment, endometriosis, birth defects, and immunological impairment (4 -6). The toxic potential of xenobiotic AhR ligands is currently a major concern for regulatory agencies that are responsible for protecting public and environmental health. Although numerous xenobiotic ligands for AhR have been identified, the AhR is considered to be an orphan receptor, because its physiological ligand(s) and its function are not known. Tryptophan and other indole-containing compounds (7-9), bilirubin (10), 7-ketocholesterol (11), lipoxin A4 (12), flavones, and related compounds (13) interact with AhR to produce activation or inhibition of signal transduction. In general, the low levels, lack of potency, and restricted distribution of these compounds make them unlikely candidates as major regulators of AhR signaling in most tissue types. We reasoned that human urine might be a good place to search for endogenous AhR ligands, and we developed a methodology to detect and isolate such compounds. EXPERIMENTAL PROCEDURESMaterials-Blue rayon was kindly provided by Dr. Hayatsu (Okayama University, Okayama City, Japan). General chemicals, essentially analytical grade, were purchased from Wako (Kyoto, Japan). TCDD was purchased from CIL (Andover, MA, USA). Indigo and ␤-glucuronidase were purchased from Sigma. Indirubin was synthesized as described in Hoessel et al. (14). Indigo and indirubin were further purified by HPLC before use.Yeast Assay for AhR Ligand Activity-The assay procedure was essentially as described by Miller (15). The yeast strain YCM3 was grown overnight at 30°C in synthetic glucose medium lacking tryptophan. Test chemicals (dissolved in Me 2 SO...

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“…Insbesondcre scheiden alle Formeln aus, die fur zwei 4-Spin-Systeme magnetische Aquivalenz erwarten lassen. Von den verbleibenden Moglichkeiten kommen nur solche in Betracht, die durch die Molekulgeometrie eine partielle Uberlappung der Molekiilteile wie in 2 a/2 b und damit die Tieffeldverschiebung wenigstens eines Aromat-Protons erwarten lassen; somit entfallen alle 1 a-Derivate.Da ,,Indigo X" um 31 nm langerwellig als Indirubin (2a) absorbiert, kommen fur seine Struktur nach HMO-Rechnungen2') und den aus Untersuchungen an substituierten Indigos abgeleitcten Regeln2') weiterhin nur Derivate in Frage, in denen die Position(en)[2][3][4] Elektronenacceptor besetzt sind oder in denen der indigoide Chromophor selbst verandert wurde.Unter den verbleibenden Moglichkeiten lieD sich die endgultige Struktur durch die vorgestellten Messungen nicht festlegen; jedoch erwies sich jetzt im direkten Vergleich 22), daD das von uns erstmals in Korperflussigkeiten gefundene indigoide Pigment ,,Indigo X" mit dem vor einiger Zeit ails Candida l i p o l y t i c~~~) isolierten und jetzt als C a~~d i d i n~~) (5) identifizierten Pigment identisch ist. Insbesondere lie13 sich so auch die isomere Struktur 6 sichcr ausschliel3en.…”

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Isolierung des indigoiden Pigmentes Candidin aus Urin und Hämofiltrat von Urämikern

Laatsch

Ludwig-Köhn

1986

Liebigs Ann. Chem.

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Blutplasma, Urin und Hamofiltrat nierenkranker Patienten ergaben nach enzymatischer Spaltung neben Indigo (la) und Indirubin (2a) in sehr geringer Menge rotviolettes Candidin (5). Das indigoide 5 konnte sich bei der Aufarbeitung aus Indikan (3a) und Tryptanthrin (7), einem moglicherweise uber den Darm resorbierten Metaboliten von Candida lipolytica, gebildet haben.After enzymic cleavage the blood plasma, urine, and haemofiltrate of uraemic patients yield, besides indigotin (la) and indirubin (2a), very small amounts of candidin (5). The indigoid 5 might have been formed from indican (3a) and tryptanthrin (7), a metabolite of Candida lipolytica possibly resorbed through the intestine.

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Some observations concerning mammlian indoxyl metabolism and its relationship to the formation of urinary indigo pigments

Cited by 21 publications

References 22 publications

Purple Urine Bag Syndrome

Purple Urine Bag Syndrome

Indirubin and Indigo Are Potent Aryl Hydrocarbon Receptor Ligands Present in Human Urine

Isolierung des indigoiden Pigmentes Candidin aus Urin und Hämofiltrat von Urämikern

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