Glucuronide identification

MOR were comparable (10 ng mL4), whereas those for DHC and EMOR were about fourfold lower. Furthermore, glucuronides were shown to react like the corresponding free opioids. Validation with real urine samples was performed with identification of the peaks by capillary electrophoresis-ion-trap mass spectrometry (CE-MS) after solid-phase extraction. 

Nishiyama T, Kobori T, Arai K, et al. Identification of human UDP-glucuronosyltransferase isoform(s) responsible for the C-glucuronidation of phenylbutazone. Arch Biochem Biophys 2006 454(l) 72-79. 

Table 12.1 Examples of different classes of compounds together with the identification of the site of glucuronidation.

J. Qu, Y. Wang, G. Luo and Z. Wu, Identification and determination of glucuronides and their aglycones in Erigeron breviscapus by liquid chromatography-tandem mass spectrometry. J. Chromatogr.A 928 (2001) 155-161. 

Collier et al. (10) demonstrated that HPLC was an effective technique for the separation of aromatic hydrocarbon metabolites in exposed marine organisms. Radioactive bioconversion products were studied in liver and gall bladder of coho salmon dosed with H-naphthalene. Quantitative identifications of glucuronide, sulphate, dihydrodiol, glycoside, and 1-naphthol derivatives were obtained. Three additional polar compounds of unknown structure were found. A typical HPLC profile is shown in Figure 2. 

Lech, J. J. Isolation and identification of 3"trifluoro-methyl-4-nitrophenyl glucuronide from bile of rainbow trout exposed to 3-trifluoromethyl-4-nitrophenol. Toxicol. Appl. Pharmacol. (1973), 24 114-124. 

D. J. Smith, M. L. Appleton, J. R. Carlson, G. S. Yost, Identification of /3-Glucuronidase-Resistant Diastereomeric Glucuronides of 3-Hydroxy-3-methyloxindole Formed During 3-Methylindole Metabolism in Goats , Drug Metab. Dispos. 1996, 24, 119 - 125. 

Shipkova, M., Armstrong, V.M., Wieland, E., Niedmann, P.D., Schiitz, E., Brenner-WeiC, G., Voihsel, M., Braun, E. and Oellerich, M., Identification of glucoside and carboxyl-linked glucuronide conjugates of mycophenolic acid in plasma of transplant recipients treated with mycophenolate mofetil. Brit. J. Pharmacol., 1999,126, 1075. 

Korfmacher WA, Holder CL, Betowski LD, et al. 1987. Identification of two glucuronide metabolites of doxylamine via thermospray/mass spectrometry and thermospray/mass spectrometry/mass spectrometry. 

Aprile S, Grosso ED, Grosa G. (2010) Identification of the human UDP-glucuronosyltransferases involved in the glucuronidation of combretastatin A-4. Drug Metab Dispos 38 1141-1146. 

Methylation of some form of 6-mercaptopurine in man has been established by the identification of 6-(methylsulphinyl)-8-hydroxypurine (LXV), 6-(methylthio)uric acid (LX), and 6-(methylthio)-8-hydroxy-A -glucuronide (LXVll). The oxidation of 6-(methylthio)purine to 6-(methylthio)-8-hydroxy-purine (LXVl) is mediated much more rapidly by rabbit liver aldehyde oxidase than by xanthine oxidase, and the oxidation is not inhibited by 4-hydroxy-pyrazolo [3, 4-d] pyrimidine [269], which is known to be an effective inhibitor of xanthine oxidase, and consequently, of the oxidation of 6-mercaptopurine [12,268]. 

Schmid, R., The identification of direct-reacting bilirubin as bilirubin glucuronide. J. Biol. Chem. 229, 881-888 (1957). 

Wittig, J., Herderich, M., Graefe, E.U., and Veit, M., Identification of quercetin glucuronides in human plasma by high-performance liquid chromatography-tandem mass spectrometry, J. Chromatogr. B Biomed. Sci. AppL, 753, 237, 2001. 

Nadelmann, L., Tjornelund, J., Hansen, S.H., Cornett, C., Sidelmann, U.G., Braumann, Christensen, E., and Christensen, S.B., Synthesis, isolation and identification of glucuronides and mercapturic acids of a novel antiparasitic agent, licochalcone A, Xenobiotica, 27, 667, 1997. 

Moon J-H, Tsushida T, Nakahara K, Terao J. 2001. Identification of quercetin 3-0-(l-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin. Free Radic Biol Med 30 1274-1285. 

Sundstrom, I., Hedeland, M., Bondesson, U., and Andren, P. E. (2002). Identification of glucuronide conjugates of ketobemidone and its phase I metabolites in human urine utilizing accurate mass and tandem time-of-flight mass spectrometry. J. Mass Spectrom. 37 414-420. 

Yoshitsugu, H., Fukuhara, T., Ishibashi, M., Nanbo, T., and Kagi, N. (1999). Key fragments for identification of positional isomer pair in glucuronides from the hydroxylated metabolites of RT-3003 (Vintoperol) by liquid chromatography/electrospray ionization mass spectrometry. J. Mass Spectrom. 34 1063-1068. 

J. Hansen-Moeller, C. Cornett, L. Dalgaard, and S. H. Hansen, Isolation and identification of the rearrangement products of diflunisal 1-O-acyl glucuronide, J. Pharm. Biomed. Anal., 6 (1988) 229-240. 

Identification of azo pigment B as a glucuronide of azo pigment A was demonstrated independently by Billing et al. (B12) and Schmid... 

Court MH, Duan SX, von Moltke LL, et al. Interindividual variability in acetaminophen glucuronidation by human liver microsomes identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther 2001 299(3) 998-1006. 

Strassburg CP, Barut A, Obermayer-Straub P, et al. Identification of cyclosporine A and tacrolimus glucuronidation in human liver and the gastrointestinal tract by a differentially expressed UDP-glucuronosyltransferase UGT2B7. J Hepatol 2001 34(6) 865-872. 

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