- Glucuronic acid
Glucuronic acid Identifiers CAS number PubChem ChemSpider UNII DrugBank KEGG MeSH ChEBI Jmol-3D images Image 1 Properties Molecular formula C6H10O7 Molar mass 194.14 g mol−1 Melting point
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Glucuronic acid (from Ancient Greek γλυκός "sweet" + οὖρον "urine") is a carboxylic acid. Its structure is similar to that of glucose. However, glucuronic acid's sixth carbon is oxidized to a carboxylic acid. Its formula is C6H10O7.
Glucuronic acid should not be confused with gluconic acid, a linear carboxylic acid resulting from the oxidation of a different carbon of glucose. Both glucuronic acid and gluconic acid are reported to be found in the fermented drink known as kombucha.
Glucuronidation of toxic substances
In the animal body, glucuronic acid is often linked to the xenobiotic metabolism of substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids. These linkages involve glycosidic bonds, and this linkage process is known as glucuronidation. Glucuronidation occurs mainly in the liver, although the enzyme responsible for its catalysis, UDP-glucuronyltransferase, has been found in all major body organs, e.g., intestine, kidneys, brain, adrenal gland, spleen, and thymus.
The substances resulting from glucuronidation are known as glucuronides (or glucuronosides) and are typically much more water-soluble than the non-glucuronic acid-containing substance from which they were originally synthesised. The human body uses glucuronidation to make a large variety of substances more water-soluble, and, in this way, allow for their subsequent elimination from the body through urine or faeces (via bile from the liver). Hormones may also be glucuronidated to allow for easier transport around the body. Pharmacologists have linked drugs to glucuronic acid to allow for more effective delivery of a broad range of substances. Sometimes toxic substances are also less toxic after glucuronidation.
The conjugation of xenobiotic molecules with hydrophilic molecular species such as glucuronic acid is known as phase II metabolism.
Determination of urinary steroids and of steroid conjugates in blood.
Contained in some commercially available brands of Kombucha as an antioxidant & organic acid
- ^ D-Glucuronic acid at Sigma-Aldrich
- ^ King C, Rios G, Green M, Tephly T (2000). "UDP-glucuronosyltransferases". Curr. Drug Metab. 1 (2): 143–61. doi:10.2174/1389200003339171. PMID 11465080.
- ^ Ohno, Shuji; Nakajin, Shizuo (2008-10-06). "Determination of mRNA Expression of Human UDP-Glucuronosyltransferases and Application for Localization in Various Human Tissues by Real-Time Reverse Transcriptase-Polymerase Chain Reaction". Drug Metabolism and Disposition (American Society for Pharmacology and Experimental Therapeutics) 37 (1): 32–40. doi:10.1124/dmd.108.023598. http://dmd.aspetjournals.org/content/37/1/32.abstract. Retrieved 2010-11-07.
- ^ Bock K, Köhle C (2005). "UDP-glucuronosyltransferase 1A6: structural, functional, and regulatory aspects". Methods enzymol. 400: 57–75. doi:10.1016/S0076-6879(05)00004-2. PMID 16399343.
- ^ Dave, G.T.. "Ingredients". Ingredients. http://www.synergydrinks.com/enlightened/kombucha_enlightened_multigreen.aspx#. Retrieved 26 August 2011.
- ^ Harvey, Richard (2011). Biochemistry (5th Edition). Philadelphia: Wolters Kluwer: Lippincott Williams and Wilkins. pp. 161. ISBN 978-1-60831-412-6.
- ^ Ferro, D. R. Provasoli, A. (1990). "Conformer populations of L-iduronic acid residues in glycosaminoglycan sequences". Carbohydr. Res. 195 (2): 157–167. doi:10.1016/0008-6215(90)84164-P. PMID 2331699.
- Chiu SH, Huskey SW (1998). "Species differences in N-glucuronidation" (abstract). Drug Metab. Dispos. 26 (9): 838–47. PMID 9733661. http://dmd.aspetjournals.org/cgi/content/abstract/26/9/838.
- Kuehl GE, Murphy SE (2003). "N-glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP-glucuronosyltransferases". Drug Metab. Dispos. 31 (11): 1361–8. doi:10.1124/dmd.31.11.1361. PMID 14570768.
- Kuehl GE, Murphy SE (2003). "N-glucuronidation of trans-3'-hydroxycotinine by human liver microsomes". Chem. Res. Toxicol. 16 (12): 1502–6. doi:10.1021/tx034173o. PMID 14680362.
- Benowitz NL, Perez-Stable EJ, Fong I, Modin G, Herrera B, Jacob P (1999). "Ethnic differences in N-glucuronidation of nicotine and cotinine". J. Pharmacol. Exp. Ther. 291 (3): 1196–203. PMID 10565842. http://www.ucsf.edu/smoking/cgi-bin/cexec/ccompletedprograms/article.pl?issn=973735131.
- Mannfred A Hollinger, Introduction to Pharmacology, ISBN 0-415-28033-8
- Chang, K. M.; McManus, K.; Greene, J.; Byrd, G. D.; DeBethizy, J. D. Glucuronidation as a metabolic pathway for nicotine metabolism. 1991
- Coffman B.L., King C.D., Rios G.R. and Tephly T.R. The glucuronidation of opioids, other xenobiotics, and androgens by human
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