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Glycyrrhizin

(Redirected from Glycyrrhizinic acid)

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.

Glycyrrhizic acid
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
  • (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 numberE958 (glazing agents, ...) Edit this at Wikidata
CompTox Dashboard (EPA)
ECHA InfoCard100.014.350 Edit this at Wikidata
Chemical and physical data
FormulaC42H62O16
Molar mass822.942 g·mol−1
3D model (JSmol)
Solubility in water1–10 mg/mL (20 °C)
  • O=C(O)[C@H]7O[C@@H](O[C@@H]6[C@@H](O)[C@H](O)[C@H](O[C@@H]6O[C@@H]2C(C)(C)[C@@H]3CC[C@@]1(C)[C@]5(C(=C/C(=O)[C@@H]1[C@@]3(C)CC2)\[C@@H]4C[C@](C(=O)O)(C)CC[C@]4(C)CC5)C)C(=O)O)[C@H](O)[C@@H](O)[C@@H]7O
  • 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 checkY
  • Key:LPLVUJXQOOQHMX-QWBHMCJMSA-N checkY

Pharmacokinetics

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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]

Flavouring properties

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Glycyrrhizin is obtained as an extract from licorice root after maceration and boiling in water.[4] Licorice extract (glycyrrhizin) is sold in the United States as a liquid, paste, or spray-dried powder.[4] When in specified amounts, it is approved for use as a flavor and aroma in manufactured foods, beverages, candies, dietary supplements, and seasonings.[4] It is 30 to 50 times as sweet as sucrose (table sugar).[5]

Adverse effects

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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.[6][7] Chronic consumption of black licorice, even in moderate amounts, is associated with an increase in blood pressure,[7] may cause irregular heart rhythm, and may have adverse interactions with prescription drugs.[6] In extreme cases, death can occur as a result of excess consumption.[8][9]

See also

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References

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  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. ^ a b Kočevar Glavač N, 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. ^ 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.
  5. ^ "Glycyrrhizic Acid". PubChem. National Institutes of Health. Retrieved 24 February 2014.
  6. ^ a b "Black Licorice: Trick or Treat?". US Food and Drug Administration. 30 October 2017. Retrieved 15 December 2017.
  7. ^ a b 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.
  8. ^ Marchione M. "Too much candy: Man dies from eating bags of black licorice". AP News. Retrieved 24 September 2020.
  9. ^ 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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