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Chemical Compound Review:

EINECS 229-896-3 sodium(2S,3S,4S,5R,6S)-3,4,5- trihydroxy-6...

Synonyms:

Norling, A. et al., Tugnait, M. et al., Sakaguchi, Y. et al., Brunelle, F.M. et al., Young, R.A. et al., et al.

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Disease relevance of PHENOLPHTHALEIN-BETA-GLUCURONIDE

beta-Glucuronidase activity determined in 100 diluted bile samples from 12 rats with bile duct fistula by using phenolphthalein glucuronide as substrate incubated at 56 degrees C and pH 6 was 636 +/- 650 (mean +/- S.D.) modified Sigma units/ml [1].

High impact information on PHENOLPHTHALEIN-BETA-GLUCURONIDE

Since phenolphthalein glucuronide does not undergo enterohepatic circulation it should theoretically have a more rapid onset of action and a lower threshold dose for laxation [2].
Biliary excretion of intravenously administered phenolphthalein glucuronide (PG) was assessed in bile duct cannulated anesthetized rats [3].
Parallel EPR and oxygen consumption studies with phenolphthalein glucuronide give analogous results, but with lesser enhancement of free radical production [4].
2. beta-Glucuronidase activity towards phenolphthalein glucuronide was much lower in microsomes prepared from human liver (45.2 +/- 3.1 Fishman Units/mg protein), human kidney (22.0 +/- 3.3 FU/mg), and rat kidney (25.1 +/- 2.5 FU/mg) as compared with rat liver (118.7 +/- 8.8 FU/mg) [5].
NMR-monitored solid-phase extraction of phenolphthalein glucuronide on phenylboronic acid and C18 bonded phases [6].

Anatomical context of PHENOLPHTHALEIN-BETA-GLUCURONIDE

Comparison of phenolphthalein and phenolphthalein glucuronide on net water transport in rat ileum and colon [7].
Phenolphthalein glucuronide had an effect on theconjugation of harmol in the isolated hepatocytes when glucuronidation was found to be markedly inhibited and sulphation slightly stimulated [8].

Associations of PHENOLPHTHALEIN-BETA-GLUCURONIDE with other chemical compounds

Levels of serum glutamic-oxalacetic transaminase (SGOT), glutamic-pyruvic transaminase (SGPT), isocitrate dehydrogenase and ornithine-carbamyl transferase, bile flow and biliary excretion of an anionic model compound, phenolphthalein glucuronide (PG), were measured on day 16 [9].
However, in hepatocytes from phenobarbital treated rats, where the rate of harmine metabolism is increased about five times and the main metabolite is harmol glucuronide, phenolphthalein glucuronide inhibited the formation of the conjugate with a concomitant increase in free harmol [8].
The glucuronidation of 4-nitrophenol, 4-methylumbelliferone and harmol in native microsomes was inhibited by phenolphthalein glucuronide [8].

Gene context of PHENOLPHTHALEIN-BETA-GLUCURONIDE

The overall recoveries of the phenolphthalein glucuronide for this procedure were high (99%), which compared well with similar studies carried out concomitantly on C18 bonded columns (93%) [6].
The Michaelis constants of beta-glucuronidase I and beta-glucuronidase II for p-nitrophenyl glucuronide were 1.25 X 10(-3) M and 4.17 X 10(-4) M, for naphthol AS-BI glucuronide 1.35 X 10(-4) M and 1.14 X 10(-4) M, and for phenolphthalein glucuronide 7.46 X 10(-5) M and 2.50 X 10(-4) M [10].

Analytical, diagnostic and therapeutic context of PHENOLPHTHALEIN-BETA-GLUCURONIDE

In contrast there was no evidence of absorption of phenolphthalein glucuronide, as 98.9 +/- 1.2% was recovered from ileal and colon perfusions [7].

References

Characterization and determination of the activity of biliary beta-glucuronidase in rats. Ho, K.J., Ho, L.H., Kruger, O.R. J. Lab. Clin. Med. (1979) [Pubmed]
Comparative assessment of phenolphthalein and phenolphthalein glucuronide: is phenolphthalein glucuronide a better laxative? Anand, B.S., Torres, E., Operkun, A., Graham, D.Y. Aliment. Pharmacol. Ther. (1994) [Pubmed]
Effect of colchicine on hepatobiliary function in CCl4 treated rats. Rao, C.V., Mehendale, H.M. Biochem. Pharmacol. (1991) [Pubmed]
In vitro free radical metabolism of phenolphthalein by peroxidases. Sipe, H.J., Corbett, J.T., Mason, R.P. Drug Metab. Dispos. (1997) [Pubmed]
Glucuronidation of diflunisal in liver and kidney microsomes of rat and man. Brunelle, F.M., Verbeeck, R.K. Xenobiotica (1996) [Pubmed]
NMR-monitored solid-phase extraction of phenolphthalein glucuronide on phenylboronic acid and C18 bonded phases. Tugnait, M., Ghauri, F.Y., Wilson, I.D., Nicholson, J.K. Journal of pharmaceutical and biomedical analysis. (1991) [Pubmed]
Comparison of phenolphthalein and phenolphthalein glucuronide on net water transport in rat ileum and colon. Sharaiha, Z.K., Sackman, J.W., Graham, D.Y. Dig. Dis. Sci. (1983) [Pubmed]
Uptake of glucuronides into isolated hepatocytes and their effects on glucuronide and sulphate conjugation. Norling, A., Andersson, B., Berggren, M., Moldéus, P. Acta pharmacologica et toxicologica. (1978) [Pubmed]
Effect of endrin and endrin derivatives on hepatobiliary function and carbon tetrachloride-induced hepatotoxicity in male and female rats. Young, R.A., Mehendale, H.M. Food Chem. Toxicol. (1986) [Pubmed]
Beta-glucuronidases of clostridium perfringens. Sakaguchi, Y., Murata, K. Zentralblatt für Bakteriologie, Mikrobiologie, und Hygiene. Series A, Medical microbiology, infectious diseases, virology, parasitology. (1984) [Pubmed]

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