Literature DB >> 3663114

Chemical synthesis and growth-promoting activity of all-trans-retinyl beta-D-glucuronide.

A B Barua1, J A Olson.   

Abstract

All-trans-retinol reacts with methyl (2,3,4-tri-O-acetyl-1-bromo-1-deoxy-beta-D-glucopyran)uronate in the presence of Ag2CO3 to give the triacetate methyl ester of retinyl beta-glucuronide. Hydrolysis of this ester with sodium methylate in methanol gives retinyl beta-D-glucuronide in about 15% yield. The water-soluble retinyl beta-D-glucuronide was characterized by u.v.-visible, n.m.r. and mass spectra, by elemental analysis and by its susceptibility to hydrolysis by bacterial beta-glucuronidase. Retinyl beta-glucuronide, when administered intraperitoneally in saline (0.9% NaCl), supports well the growth of vitamin A-deficient rats.

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Year:  1987        PMID： 3663114      PMCID： PMC1147976          DOI： 10.1042/bj2440231

Source DB:  PubMed          Journal:  Biochem J        ISSN： 0264-6021            Impact factor:   3.857


  14 in total

1.  Natural occurrence and biological activity of vitamin A derivatives in rat bile.

Authors:  K Nath; J A Olson
Journal:  J Nutr       Date:  1967-12       Impact factor: 4.798

2.  13-cis-retinoic acid metabolism in vivo. The major tissue metabolites in the rat have the all-trans configuration.

Authors:  A M McCormick; K D Kroll; J L Napoli
Journal:  Biochemistry       Date:  1983-08-02       Impact factor: 3.162

3.  Retinoic acid: an endogenous compound of human blood. Unequivocal demonstration of endogenous retinoic acid in normal physiological conditions.

Authors:  M G De Ruyter; W E Lambert; A P De Leenheer
Journal:  Anal Biochem       Date:  1979-10-01       Impact factor: 3.365

4.  Formation and enterohepatic circulation of metabolites of retinol and retinoic acid in bile duct-cannulated rats.

Authors:  R D Zachman; P E Dunagin; J A Olson
Journal:  J Lipid Res       Date:  1966-01       Impact factor: 5.922

5.  A new vaginal smear assay for vitamin A in rats.

Authors:  W K Sietsema; H F DeLuca
Journal:  J Nutr       Date:  1982-08       Impact factor: 4.798

6.  Vitamin A metabolism in chick liver: some properties of the cytosolic lipid-protein aggregate.

Authors:  D Sklan; O Halevy
Journal:  Br J Nutr       Date:  1984-07       Impact factor: 3.718

7.  Biosynthesis of beta-glucuronides of retinol and of retinoic acid in vivo and in vitro.

Authors:  K Lippel; J A Olson
Journal:  J Lipid Res       Date:  1968-03       Impact factor: 5.922

8.  Metabolism in vivo of all-trans-retinoic acid. Biosynthesis of 13-cis-retinoic acid and all-trans- and 13-cis-retinoyl glucuronides in the intestinal mucosa of the rat.

Authors:  M H Zile; R C Inhorn; H F DeLuca
Journal:  J Biol Chem       Date:  1982-04-10       Impact factor: 5.157

9.  Metabolism of all-trans-retinoic acid and all-trans-retinyl acetate. Demonstration of common physiological metabolites in rat small intestinal mucosa and circulation.

Authors:  M E Cullum; M H Zile
Journal:  J Biol Chem       Date:  1985-09-05       Impact factor: 5.157

10.  Metabolism of isotretinoin. Biliary excretion of isotretinoin glucuronide in the rat.

Authors:  S Meloche; J G Besner
Journal:  Drug Metab Dispos       Date:  1986 Mar-Apr       Impact factor: 3.922
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  7 in total

1.  Application of photoaffinity labeling with [(3)H] all trans- and 9-cis-retinoic acids for characterization of cellular retinoic acid--binding proteins I and II.

Authors:  A Radominska-Pandya; G Chen; V M Samokyszyn; J M Little; W E Gall; G Zawada; N Terrier; J Magdalou; P Czernik
Journal:  Protein Sci       Date:  2001-01       Impact factor: 6.725

2.  Chemical synthesis of all-trans-[11-3H]retinoyl beta-glucuronide and its metabolism in rats in vivo.

Authors:  A B Barua; J A Olson
Journal:  Biochem J       Date:  1989-10-15       Impact factor: 3.857

3.  All-trans-retinoyl beta-glucuronide: new procedure for chemical synthesis and its metabolism in vitamin A-deficient rats.

Authors:  B Becker; A B Barua; J A Olson
Journal:  Biochem J       Date:  1996-02-15       Impact factor: 3.857

4.  Temporal distribution, localization and metabolism of all-trans-retinol, didehydroretinol and all-trans-retinal during Xenopus development.

Authors:  J Creech Kraft; T Schuh; M R Juchau; D Kimelman
Journal:  Biochem J       Date:  1994-07-01       Impact factor: 3.857

5.  Synthesis and metabolism of all-trans-[11-3H]retinyl beta-glucuronide in rats in vivo.

Authors:  A B Barua; R O Batres; J A Olson
Journal:  Biochem J       Date:  1988-06-01       Impact factor: 3.857

Review 6.  Glucuronidation of drugs. A re-evaluation of the pharmacological significance of the conjugates and modulating factors.

Authors:  H K Kroemer; U Klotz
Journal:  Clin Pharmacokinet       Date:  1992-10       Impact factor: 6.447

7.  Characterization of human hepatic and extrahepatic UDP-glucuronosyltransferase enzymes involved in the metabolism of classic cannabinoids.

Authors:  Anna Mazur; Cheryl F Lichti; Paul L Prather; Agnieszka K Zielinska; Stacie M Bratton; Anna Gallus-Zawada; Moshe Finel; Grover P Miller; Anna Radomińska-Pandya; Jeffery H Moran
Journal:  Drug Metab Dispos       Date:  2009-04-01       Impact factor: 3.922
  7 in total

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