Glycyrrhizin

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Glycyrrhizic acid
Glycyrrhizic Acid.svg
Glycyrrhizin zwitterion ball-and-stick xtal 2009.png
Clinical data
Trade namesEpigen, Glycyron
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral, intravenous
ATC code
Pharmacokinetic data
MetabolismHepatic and by intestinal bacteria
Elimination half-life6.2-10.2 hours[1]
ExcretionFaeces, urine (0.31-0.67%)[2]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
E numberE958 (glazing agents, ...) Edit this at Wikidata
ECHA InfoCard100.014.350 Edit this at Wikidata
Chemical and physical data
FormulaC42H62O16
Molar mass822.93 g/mol
3D model (JSmol)
Solubility in water1-10 mg/mL (20 °C)

Glycyrrhizin (or glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of Glycyrrhiza glabra (liquorice) root. Structurally, it is a saponin used as an emulsifier and gel-forming agent in foodstuffs and cosmetics. Its aglycone is enoxolone assessed as a prodrug used in Japan to reduce the risk of liver cancer in people with chronic hepatitis C.[3][4]

Adverse effects[edit]

The most widely reported side effect of glycyrrhizin use via consumption of black licorice is reduction of blood potassium levels, which can affect body fluid balance and function of nerves.[5][6] Chronic consumption of black licorice, even in moderate amounts, is associated with an increase in blood pressure,[6] may cause irregular heart rhythm, and adverse interactions with prescription medicines.[5]

The effects on body fluids are related to the inhibition of cortisol metabolism within the kidney, subsequent stimulation of the mineralocorticoid receptors,[7] and decrease in blood levels of renin, potassium, and aldosterone, which collectively lead to increases in blood pressure.[6]

Depending on amount and frequency of ingesting black licorice, other side effects may include:[5][8]

Research[edit]

Glycyrrhizin is under laboratory and preliminary clinical research for its possible activity against common viruses, such as hepatitis C.[4] In vitro, glycyrrhizin inhibits the enzyme 11β-hydroxysteroid dehydrogenase.[8]

Pharmacokinetics[edit]

After oral ingestion, glycyrrhizin is first hydrolysed to 18β-glycyrrhetinic acid (enoxolone) by intestinal bacteria. After complete absorption from the gut, 18β-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.[quantify] The main part is eliminated by bile and only a minor part (0.31–0.67%) by urine.[9] 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.[9]

Flavouring properties[edit]

Glycyrrhizin is obtained as an extract from licorice root after maceration and boiling in water.[10] Licorice extract (glycyrrhizin) is sold in the United States as a liquid, paste, or spray-dried powder.[10] When in specified amounts, it is approved for use as a flavor and aroma in manufactured foods, beverages, candies, dietary supplements, and seasonings.[10] It is 30 to 50 times as sweet as sucrose (table sugar).[8][11]

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. ^ Arase, Yasuji; Ikeda, Kenji; Murashima, Naoya; Chayama, Kazuaki; Tsubota, Akihito; Koida, Isao; Suzuki, Yoshiyuki; Saitoh, Satoshi; Kobayashi, Masahiro; Kumada, Hiromitsu (15 April 1997). "The long term efficacy of glycyrrhizin in chronic hepatitis C patients". Cancer. 79 (8): 1494–1500. doi:10.1002/(SICI)1097-0142(19970415)79:8<1494::AID-CNCR8>3.0.CO;2-B.
  4. ^ a b Fiore, C; Eisenhut, M; Krausse, R; Ragazzi, E; Pellati, D; Armanini, D; Bielenberg, J (2008). "Antiviral effects of Glycyrrhiza species". Phytotherapy Research. 22 (2): 141–8. doi:10.1002/ptr.2295. PMID 17886224.
  5. ^ a b c "Black Licorice: Trick or Treat?". US Food and Drug Administration. 30 October 2017. Retrieved 15 December 2017.
  6. ^ a b c Penninkilampi, R; Eslick, E. M; Eslick, G. D (2017). "The association between consistent licorice ingestion, hypertension and hypokalaemia: A systematic review and meta-analysis". Journal of Human Hypertension. 31 (11): 699–707. doi:10.1038/jhh.2017.45. PMID 28660884.
  7. ^ 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.
  8. ^ a b c Asl, MN; Hosseinzadeh, H (1 June 2008). "Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds". Phytotherapy Research. 22 (6): 709–24. doi:10.1002/ptr.2362. PMID 18446848.
  9. ^ a b Kočevar Glavač, Nina; Kreft, Samo (2012). "Excretion profile of glycyrrhizin metabolite in human urine". Food Chemistry. 131: 305–308. doi:10.1016/j.foodchem.2011.08.081.
  10. ^ a b c "Sec. 184.1408 Licorice and licorice derivatives". US Food and Drug Administration, Code of Federal Regulations Title 21, 21CFR184.1408. 1 April 2017. Retrieved 15 December 2017.
  11. ^ "Glycyrrhizic Acid". PubChem. National Institutes of Health. Retrieved 24 February 2014.

External links[edit]