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A good picture of the whole system:

Glutathione-S-transferase detoxifies many water-soluble environmental toxins, including many solvents, herbicides, fungicides, lipid peroxides, and heavy metals (e.g., mercury, cadmium, and lead). The various forms of GST work together to eliminate toxins. Decreased glutathione conjugation capacity may incrase toxic burden and increase oxidative stress.

T2 - Journal of Pharmacology and Experimental Therapeutics

N-Glucuronidation of 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) and N-hydroxy-PhIP by specific human UDP-glucuronosyltransferases

Glucuronidation has been well established as a major conjugation reaction in the biotransformation of many xenobiotics. These conjugation reactions are catalyzed by numerous isoforms of UDP-glucuronosyltransferase (UGT) (1). These enzymes are primarily found in the endoplasmic reticulum of many tissues, with the liver being, quantitatively, the most significant site of glucuronidation. In addition to a wide tissue distribution of UGTs, different isozymes can be preferentially expressed in specific tissues. Furthermore, polymorphic expression of certain UGTs has also been observed (2). Three UGT families have been identified in humans; designated UGT1, UGT2 and UGT8 based on their evolutionary divergence (1). Of these three families UGT1 and UGT2 have been shown to catalyze the glucuronidation of a wide variety of xenobiotic substrates, with UGT1 being more active in the glucuronidation of amines (3,4). Aryl- and alkylamines, sulfonamides, heterocyclic amines and hydroxylated compounds have all been reported to undergo glucuronidation in many animal species and humans. The primary function of UGTs is to eliminate substrates from the body via urine and feces by catalyzing the formation of hydrophilic glucuronide conjugates (5).

JF - Journal of Pharmacology and Experimental Therapeutics

Glucuronide donors and intermediates for the synthesis of drug metabolites in your laboratory.

Glucuronides are formed when a glucuronic acid is bound in vivo to a drug or xenobiotic. In nature, glucuronidation is one of the main phase 2 metabolic pathways by which an organism transforms a small molecule drug or xenobiotic into a more water soluble substance which may be responsible for a drug’s therapeutic affect but certainly enable its detoxification and further excretion. Glucuronides are formed enzymatically by the UDP-Glucuronosyltransferases which have been reported active in the liver, kidneys, epithelial cells of the lower gastrointestinal tract and the brain.

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Congratulations to the winners of the 2016 Nobel Prize in Chemistry

The synthesis of curcumin monoglucuronide was performed in three stages, as described in ,  and .

Although the principal products were 4-O-glucuronides (i.e., linkage through a phenolic hydroxyl), significant quantities of the 6′-O-glucuronides (i.e., linkage through the aliphatic hydroxyl) of alcohols 2, 4, and 5 were also isolated.

Minimizing Risks: Avoid excessive alcohol consumption; seek help if alcohol consumption is a health issue. Minimize sustained mental and environmental stress (stress hormones require COMT for their degradation, thus can decrease the methylation of estrogen compounds). Ensure adequate intake of B vitamins, magnesium, and protein.

The authors declare no conflict of interest.
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Glucuronide Synthesis | Synthose

AB - N-Glucuronides of norgallopamil and norverapamil were found as biliary metabolites after administering the corresponding tertiary amines, gallopamil and verapamil, to rats. The structures of these unusual metabolites were established by comparison with spectral data of synthesized authentic standards and by enzymic hydrolysis of the conjugates. The N-glucuronide standards were synthesized by coupling the secondary amines to either glucuronic acid or to methyl tetra-O-acetyl-β-D-glucopyranuronate. On i.p. dosing of rats with gallopamil or verapamil, 13 and 2% of the dose, respectively, appeared in the bile as the N-glucuronide of the secondary amine metabolite over an 8-hr period. Administration of norgallopamil resulted in approximately 25% of the dose being excreted as N-glucuronide conjugate in the bile. Substantially more of the S- than R-enantiomer of both gallopamil and verapamil was converted to the corresponding secondary amine N-glucuronide. The observed high S/R ratios suggest enantio-selectivity in this pathway could contribute to the observed stereoselectivity in other routes of metabolism of the parent tertiary amines.

The synthesis of O-glucuronides - Natural Product …

The access of alternative synthetic approaches in the literature on the synthesis of the same molecule could open up a number of choices in the scientific community in case they wish to elaborate the study in the same scientific field. The chemical synthesis of curcumin monoglucuronide was reported recently by Bornmann . [], however we have developed an alternative synthetic approach to synthesize curcumin monoglucuronide in gram quantity. Our practical synthesis of curcumin monoglucuronide () in gram quantity has not yet been reported.

The synthesis of O-glucuronides.

Meanwhile, analytical data for curcumin diglucuronide () and its acetylated intermediate were reported [] but so far there are no experimental details accessible from the literature for synthesizing these two molecules. We are the first to report herein the experimental details on synthesizing curcumin diglucuronide and its intermediate acetylated curcumin diglucuronide.

The synthesis of O-glucuronides

Curcumin is well recognized as an anti-oxidant and reported to have free radicals scavenging activity [] that recommends its application as an anti-cancer agent []. However, it is not clear whether curcumin retains its anti-oxidant activity after it is orally administered or after bioconversion into its metabolites, curcumin glucuronides, that may still retain the anti-oxidant activity inside the body system. To find a plausible explanation, we focused on synthesizing and studying the anti-oxidant activity of curcumin glucuronides in focused manner with respect to curcumin and the results are elaborated in this report. This study clearly demonstrates that curcumin monoglucuronide shows 10 fold less anti-oxidant activity and curcumin diglucuronide is not at all noticeably effective as an anti-oxidant in comparison to anti-oxidant activity of curcumin (by DPPH). It is concluded that glucuronide metabolites of curcumin, namely, curcumin monoglucuronide and curcumin di-glucuronide are not active components exhibiting anti-oxidant activity of curcumin after its oral administration.

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