Glycyrrhizin

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Glycyrrhizic acid
Glycyrrhizic Acid.svg
Glycyrrhizin3Dan.gif
Systematic (IUPAC) name
(3β,18α)-30-hydroxy-11,30-dioxoolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acid
Clinical data
Trade names Epigen, Glycyron
AHFS/Drugs.com International Drug Names
Legal status Generally regarded as safe
Routes Oral, intravenous
Pharmacokinetic data
Metabolism Hepatic and by intestinal bacteria
Half-life 6.2-10.2 hours[1]
Excretion Faeces, urine (0.31-0.67%)[2]
Identifiers
ATC code A05BA08
PubChem CID 14982
ChemSpider 14263 YesY
UNII 6FO62043WK
ChEBI CHEBI:15939 YesY
ChEMBL CHEMBL441687 YesY
Chemical data
Formula C42H62O16 
Mol. mass 822.93 g/mol
Physical data
Solubility in water 1-10 mg/mL (20 °C)

Glycyrrhizin (or glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of Glycyrrhiza glabra (liquorice) root. It has also been given intravenously in Japan as a treatment for hepatitis C and as an emusifier and gel-forming agent in foodstuff and cosmetics.

Medical uses[edit]

Glycyrrhizin inhibits liver cell injury and is given intravenously for the treatment of chronic viral hepatitis and cirrhosis in Japan.[3][4] It has also proven itself effective in the treatment of autoimmune hepatitis in one clinical trial.[5]

Adverse effects[edit]

The most widely reported side-effects of glycyrrhizin use are oedema (water retention). These effects are related to the inhibition of cortisol metabolism within the kidney, and the subsequent stimulation of the mineralocorticoid receptors.[6] Other side effects include:[7]

Mechanism of action[edit]

It inhibits the enzyme 11beta-hydroxysteroid dehydrogenase, which likely contribute to its anti-inflammatory and mineralocorticoid activity.[7] It has broad-spectrum antiviral activity in vitro against:[7][8]

Pharmacokinetics[edit]

After oral ingestion, glycyrrhizin is first hydrolysed to 18β-glycyrrhetinic acid by intestinal bacteria. After complete absorption from the gut, β-glycyrrhetinic acid is metabolised to 3β-monoglucuronyl-18β-glycyrrhetinic acid in the liver. This metabolite then circulates in the bloodstream. Consequently its oral bioavailability is poor. The main part is eliminated by bile and only a minor part (0.31–0.67%) by urine.[13] After oral ingestion of 600 mg of glycyrrhizin the metabolite appeared in urine after 1.5 to 14 hours. Maximal concentrations (0.49 to 2.69 mg/l) were achieved after 1.5 to 39 hours and metabolite can be detected in the urine after 2 to 4 days.[13]

Organoleptic properties[edit]

It is 30-50 times as sweet as sucrose (table sugar).[7][14]

See also[edit]

References[edit]

  1. ^ van Rossum, TG; Vulto, AG; Hop, WC; Schalm, SW (December 1999). "Pharmacokinetics of intravenous glycyrrhizin after single and multiple doses in patients with chronic hepatitis C infection.". Clinical Therapeutics 21 (12): 2080–90. doi:10.1016/S0149-2918(00)87239-2. PMID 10645755. 
  2. ^ Ploeger, B; Mensinga, T; Sips, A; Seinen, W; Meulenbelt, J; DeJongh, J (May 2001). "The pharmacokinetics of glycyrrhizic acid evaluated by physiologically based pharmacokinetic modeling.". Drug Metabolism Reviews 33 (2): 125–47. doi:10.1081/DMR-100104400. PMID 11495500. 
  3. ^ Sato, H; Goto, W; Yamamura, J; Kurokawa, M; Kageyama, S; Takahara, T; Watanabe, A; Shiraki, K (May 1996). "Therapeutic basis of glycyrrhizin on chronic hepatitis B.". Antiviral Research 30 (2-3): 171–7. doi:10.1016/0166-3542(96)00942-4. PMID 8783808. 
  4. ^ van Rossum, TG; Vulto, AG; de Man, RA; Brouwer, JT; Schalm, SW (March 1998). "Review article: glycyrrhizin as a potential treatment for chronic hepatitis C." (PDF). Alimentary Pharmacology & Therapeutics 12 (3): 199–205. doi:10.1046/j.1365-2036.1998.00309.x. PMID 9570253. 
  5. ^ Yasui, S; Fujiwara, K; Tawada, A; Fukuda, Y; Nakano, M; Yokosuka, O (December 2011). "Efficacy of intravenous glycyrrhizin in the early stage of acute onset autoimmune hepatitis.". Digestive Diseases and Sciences 56 (12): 3638–47. doi:10.1007/s10620-011-1789-5. PMID 21681505. 
  6. ^ Ferrari, P.; Sansonnens, A.; Dick, B.; Frey, F. J. (2001). "In Vivo 11 -HSD-2 Activity: Variability, Salt-Sensitivity, and Effect of Licorice". Hypertension 38 (6): 1330–6. doi:10.1161/hy1101.096112. PMID 11751713. 
  7. ^ a b c d Asl, MN; Hosseinzadeh, H (June 2008). "Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds." (PDF). Phytotherapy research 22 (6): 709–24. doi:10.1002/ptr.2362. PMID 18446848. 
  8. ^ Shamsa, F; Ohtsuki, K; Hasanzadeh, E; Rezazadeh, S (2010). "The Anti-inflammatory and Anti-viral Effects of an Ethnic Medicine: Glycyrrhizin" (PDF). Journal of Medicinal Plants 9 (Suppl. 2): 1389. 
  9. ^ Pompei, Raffaello; Flore, Ornella; Marccialis, Maria Antonietta; Pani, Alessandra; Loddo, Bernardo (1979). "Glycyrrhizic acid inhibits virus growth and inactivates virus particles". Nature 281 (5733): 689–90. doi:10.1038/281689a0. PMID 233133. 
  10. ^ Sekizawa, T; Yanagi, K; Itoyama, Y (February 2001). "Glycyrrhizin increases survival of mice with herpes simplex encephalitis.". Acta Virologica 45 (1): 51–4. PMID 11394578. 
  11. ^ Michaelis, Martin; Geiler, Janina; Naczk, Patrizia; Sithisarn, Patchima; Leutz, Anke; Doerr, Hans Wilhelm; Cinatl, Jindrich (2011). "Glycyrrhizin Exerts Antioxidative Effects in H5N1 Influenza a Virus-Infected Cells and Inhibits Virus Replication and Pro-Inflammatory Gene Expression". In Pekosz, Andrew. PLoS ONE 6 (5): e19705. doi:10.1371/journal.pone.0019705. PMC 3096629. PMID 21611183. 
  12. ^ Baba, M; Shigeta, S (February 1987). "Antiviral activity of glycyrrhizin against varicella-zoster virus in vitro.". Antiviral Research 7 (2): 99–107. doi:10.1016/0166-3542(87)90025-8. PMID 3034150. 
  13. ^ a b Kočevar Glavač, Nina; Kreft, Samo (2012). "Excretion profile of glycyrrhizin metabolite in human urine". Food Chemistry 131: 305. doi:10.1016/j.foodchem.2011.08.081. 
  14. ^ "Glycyrrhizic Acid". PubChem. National Institutes of Health. Retrieved 24 February 2014.