Glycyrrhizin

Last updated

Glycyrrhizic acid
Glycyrrhizic Acid.svg
Glycyrrhizin zwitterion ball-and-stick xtal 2009.png
Clinical data
Trade names Epigen, Glycyron
AHFS/Drugs.com International Drug Names
Routes of
administration 		Oral, intravenous
ATC code
Pharmacokinetic data
Metabolism Hepatic and by intestinal bacteria
Elimination half-life 6.2–10.2 hours [1]
Excretion Faeces, urine (0.31–0.67%) [2]
Identifiers
  • (3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number E958 (glazing agents, ...) OOjs UI icon edit-ltr-progressive.svg
CompTox Dashboard (EPA)
ECHA InfoCard 100.014.350 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C42H62O16
Molar mass 822.942 g·mol−1
3D model (JSmol)
Solubility in water 1–10 mg/mL (20 °C)
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  • InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1 Yes check.svgY
  • Key:LPLVUJXQOOQHMX-QWBHMCJMSA-N Yes check.svgY

Glycyrrhizin (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.

Contents

Pharmacokinetics

After oral ingestion, glycyrrhizin is hydrolysed to 18β-glycyrrhetinic acid (enoxolone) by intestinal bacteria. After absorption from the gut, 18β-glycyrrhetinic acid is metabolised to 3β-monoglucuronyl-18β-glycyrrhetinic acid in the liver. This metabolite circulates in the bloodstream. Consequently, its oral bioavailability is poor.[ quantify ] Most of it is eliminated by bile and only a minor part (0.31–0.67%) by urine. [3] 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. [3]

Pharmacological action

The polypharmacological effect of glycyrrhizinic acid, which has at least 12 types of activity [4] (antitumor [5] , hepatoprotective [6] , immunomodulatory, antidiabetic, nephroprotective, cardioprotective, neuroprotective, atheroprotective, anti-inflammatory, antithrombotic, etc.), is closely related to its interaction with various cellular targets. Approximately 88 cellular proteins [4] have been experimentally identified as potential targets of glycyrrhizic acid, including cytochromes P450, UDP-glucouronosyltransferases, oxidoreductases, and proteins involved in amino acid metabolism and steroid hormone biosynthesis.

Flavouring properties

Glycyrrhizin is obtained as an extract from licorice root after maceration and boiling in water. [7] Licorice extract (glycyrrhizin) is sold in the United States as a liquid, paste, or spray-dried powder. [7] When in specified amounts, it is approved for use as a flavor and aroma in manufactured foods, beverages, candies, dietary supplements, and seasonings. [7] It is 30 to 50 times as sweet as sucrose (table sugar). [8]

Adverse effects

The most widely reported side effect of glycyrrhizin use via consumption of black liquorice is reduction of blood potassium levels, which can affect body fluid balance and function of nerves. [9] [10] Chronic consumption of black licorice, even in moderate amounts, is associated with an increase in blood pressure, [10] may cause irregular heart rhythm, and may have adverse interactions with prescription drugs. [9] In extreme cases, death can occur as a result of excess consumption. [11] [12]

See also

References

  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): 2080–2090. doi:10.1016/S0149-2918(00)87239-2. hdl: 1765/73160 . 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): 125–147. doi:10.1081/DMR-100104400. PMID   11495500. S2CID   24778157.
  3. 1 2 Glavač NK, Kreft S (2012). "Excretion profile of glycyrrhizin metabolite in human urine". Food Chemistry. 131: 305–308. doi:10.1016/j.foodchem.2011.08.081.
  4. 1 2 Ershov PV, Yablokov EO, Kaluzhskiy LA, Mezentsev YV, Gnedenko OV, Konstantinov MA, et al. (September 2025). "Glycyrrhizic acid: novel potential protein targets". Biomeditsinskaia Khimiia (in Russian). 71 (4): 270–282. doi:10.18097/PBMCR1595. PMID   40904179.
  5. ↑ Su X, Wu L, Hu M, Dong W, Xu M, Zhang P (November 2017). "Glycyrrhizic acid: A promising carrier material for anticancer therapy". Biomedicine & Pharmacotherapy. 95: 670–678. doi:10.1016/j.biopha.2017.08.123. PMID   28886526.
  6. ↑ Cao R, Gong H, Xia S, Hu Z, Fan X, Zhai B, et al. (June 2025). "Glycyrrhizic acid promotes liver regeneration through activating β-catenin in acetaminophen-induced liver injury". Journal of Ethnopharmacology. 349 119895. doi:10.1016/j.jep.2025.119895. PMID   40306499.
  7. 1 2 3 "Sec. 184.1408 Licorice and licorice derivatives". US Food and Drug Administration, Code of Federal Regulations Title 21, 21CFR184.1408. 1 April 2017. Archived from the original on May 10, 2003. Retrieved 15 December 2017.
  8. ↑ "Glycyrrhizic Acid". PubChem. National Institutes of Health. Retrieved 24 February 2014.
  9. 1 2 "Black Licorice: Trick or Treat?". US Food and Drug Administration. 30 October 2017. Archived from the original on October 27, 2011. Retrieved 15 December 2017.
  10. 1 2 Penninkilampi R, Eslick EM, Eslick GD (November 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. S2CID   205168217.
  11. ↑ Marchione M. "Too much candy: Man dies from eating bags of black licorice". AP News. Retrieved 24 September 2020.
  12. ↑ Edelman ER, Butala NM, Avery LL, Lundquist AL, Dighe AS (September 2020). "Case 30-2020: A 54-Year-Old Man with Sudden Cardiac Arrest". The New England Journal of Medicine. 383 (13): 1263–1275. doi:10.1056/NEJMcpc2002420. PMC   8568064 . PMID   32966726.

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