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'''Glycyrrhizin''' (or '''glycyrrhizic acid''' or '''glycyrrhizinic acid''') is the chief [[Sweetness|sweet-tasting]] constituent of ''Glycyrrhiza glabra'' ([[liquorice]]) root. Structurally, it is a [[saponin]] used as an [[emulsion|emulsifier]] and [[gel]]-forming agent in foodstuffs and [[cosmetics]]. A preparation containing glycyrrhizin, Stronger neo-minophagen C (SNMC), is used in Japan to treat chronic [[hepatitis C]].<ref>{{Cite book|last=Information|first=National Center for Biotechnology|url=https://www.ncbi.nlm.nih.gov/books/NBK293057/|title=Efficacy and safety of stronger neo-minophagen C for treatment of chronic hepatitis B: a meta-analysis of randomized controlled trials|last2=Pike|first2=U. S. National Library of Medicine 8600 Rockville|last3=MD|first3=Bethesda|last4=Usa|first4=20894|date=2014|publisher=Centre for Reviews and Dissemination (UK)|language=en|pmid=25176104}}</ref><ref>{{Cite journal|last=Iino|first=Shiro|last2=Tango|first2=Toshiro|last3=Matsushima|first3=Takashi|last4=Toda|first4=Gotaro|last5=Miyake|first5=Kazuhiko|last6=Hino|first6=Kunihiko|last7=Kumada|first7=Hiromitsu|last8=Yasuda|first8=Kiyomi|last9=Kuroki|first9=Tetsuo|last10=Hirayama|first10=Chisato|last11=Suzuki|first11=Hiroshi|date=2001-01-01|title=Therapeutic effects of stronger neo-minophagen C at different doses on chronic hepatitis and liver cirrhosis|url=http://www.sciencedirect.com/science/article/pii/S1386634600000796|journal=Hepatology Research|language=en|volume=19|issue=1|pages=31–40|doi=10.1016/S1386-6346(00)00079-6|issn=1386-6346}}</ref> Its [[aglycone]] is [[enoxolone]].
'''Glycyrrhizin''' (or '''glycyrrhizic acid''' or '''glycyrrhizinic acid''') is the chief [[Sweetness|sweet-tasting]] constituent of ''Glycyrrhiza glabra'' ([[liquorice]]) root. Structurally, it is a [[saponin]] used as an [[emulsion|emulsifier]] and [[gel]]-forming agent in foodstuffs and [[cosmetics]].


==Adverse effects==
==Adverse effects==
The most widely reported side effect of glycyrrhizin use via consumption of [[Liquorice (confectionery)|black licorice]] is reduction of blood [[Potassium in biology|potassium]] levels, which can affect body [[fluid balance]] and function of [[nerve]]s.<ref name="fda-cons">{{cite web|title=Black Licorice: Trick or Treat?|url=https://www.fda.gov/ForConsumers/ConsumerUpdates/ucm277152.htm|publisher=US Food and Drug Administration|access-date=15 December 2017|date=30 October 2017}}</ref><ref name="jhh">{{cite journal | vauthors = Penninkilampi R, Eslick EM, Eslick GD | title = The association between consistent licorice ingestion, hypertension and hypokalaemia: a systematic review and meta-analysis | journal = Journal of Human Hypertension | volume = 31 | issue = 11 | pages = 699–707 | date = November 2017 | pmid = 28660884 | doi = 10.1038/jhh.2017.45 }}</ref> Chronic consumption of black licorice, even in moderate amounts, is associated with an increase in [[blood pressure]],<ref name=jhh/> may cause [[Heart arrhythmia|irregular heart rhythm]], and adverse interactions with [[prescription medicine]]s.<ref name=fda-cons/>
The most widely reported side effect of glycyrrhizin use via consumption of [[Liquorice (confectionery)|black licorice]] is reduction of blood [[Potassium in biology|potassium]] levels, which can affect body [[fluid balance]] and function of [[nerve]]s.<ref name="fda-cons">{{cite web|title=Black Licorice: Trick or Treat?|url=https://www.fda.gov/ForConsumers/ConsumerUpdates/ucm277152.htm|publisher=US Food and Drug Administration|access-date=15 December 2017|date=30 October 2017}}</ref><ref name="jhh">{{cite journal | vauthors = Penninkilampi R, Eslick EM, Eslick GD | title = The association between consistent licorice ingestion, hypertension and hypokalaemia: a systematic review and meta-analysis | journal = Journal of Human Hypertension | volume = 31 | issue = 11 | pages = 699–707 | date = November 2017 | pmid = 28660884 | doi = 10.1038/jhh.2017.45 }}</ref> Chronic consumption of black licorice, even in moderate amounts, is associated with an increase in [[blood pressure]],<ref name=jhh/> may cause [[Heart arrhythmia|irregular heart rhythm]], and adverse interactions with [[prescription medicine]]s.<ref name=fda-cons/>

The effects on body fluids are related to the inhibition of [[cortisol]] metabolism within the kidney, subsequent stimulation of the [[mineralocorticoid]] receptors,<ref>{{cite journal | vauthors = Ferrari P, Sansonnens A, Dick B, Frey FJ | title = In vivo 11beta-HSD-2 activity: variability, salt-sensitivity, and effect of licorice | journal = Hypertension | volume = 38 | issue = 6 | pages = 1330–6 | date = December 2001 | pmid = 11751713 | doi = 10.1161/hy1101.096112 | citeseerx = 10.1.1.620.857 }}</ref> and decrease in blood levels of [[renin]], potassium, and [[aldosterone]], which collectively lead to increases in blood pressure.<ref name=jhh/>

Depending on amount and frequency of ingesting black licorice, other side effects may include:<ref name=fda-cons/>
{{div col|colwidth=18em}}
* [[Edema]]
* [[Lethargy]]
* Headache
* Paralysis
* Transient visual loss
* [[Torsades de pointes]]
* Tachycardia
* Cardiac arrest
* Reduced testosterone
* Premature birth
* Acute [[kidney failure]]
* Muscle weakness
* [[Myopathy]]
* [[Myoglobinuria]]
* [[Rhabdomyolysis]]
* Increased body weight
{{div col end}}


==Pharmacokinetics==
==Pharmacokinetics==

Revision as of 08:54, 25 April 2020

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べーた,20βべーた)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-βべーた-D-glucopyranuronosyl-αあるふぁ-D-glucopyranosiduronic acid
CAS Number
  • 1405-86-3 (αあるふぁ-D-Glucopyranosiduronic acid), 103000-77-7 (βべーた-D-Glucopyranosiduronic acid)
PubChem CID
ChemSpider
UNII
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 mass822.93 g/mol 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

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. A preparation containing glycyrrhizin, Stronger neo-minophagen C (SNMC), is used in Japan to treat chronic hepatitis C.[3][4] Its aglycone is enoxolone.

Adverse effects

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]

Pharmacokinetics

After oral ingestion, glycyrrhizin is first hydrolysed to 18βべーた-glycyrrhetinic acid (enoxolone) by intestinal bacteria. After complete absorption from the gut, 18βべーた-glycyrrhetinic acid is metabolised to 3βべーた-monoglucuronyl-18βべーた-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.[8] 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.[8]

Flavouring properties

Glycyrrhizin is obtained as an extract from licorice root after maceration and boiling in water.[9] Licorice extract (glycyrrhizin) is sold in the United States as a liquid, paste, or spray-dried powder.[9] When in specified amounts, it is approved for use as a flavor and aroma in manufactured foods, beverages, candies, dietary supplements, and seasonings.[9] It is 30 to 50 times as sweet as sucrose (table sugar).[10]

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): 2080–90. 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): 125–47. doi:10.1081/DMR-100104400. PMID 11495500.
  3. ^ Information, National Center for Biotechnology; Pike, U. S. National Library of Medicine 8600 Rockville; MD, Bethesda; Usa, 20894 (2014). Efficacy and safety of stronger neo-minophagen C for treatment of chronic hepatitis B: a meta-analysis of randomized controlled trials. Centre for Reviews and Dissemination (UK). PMID 25176104. {{cite book}}: |first4= has numeric name (help)CS1 maint: numeric names: authors list (link)
  4. ^ Iino, Shiro; Tango, Toshiro; Matsushima, Takashi; Toda, Gotaro; Miyake, Kazuhiko; Hino, Kunihiko; Kumada, Hiromitsu; Yasuda, Kiyomi; Kuroki, Tetsuo; Hirayama, Chisato; Suzuki, Hiroshi (2001-01-01). "Therapeutic effects of stronger neo-minophagen C at different doses on chronic hepatitis and liver cirrhosis". Hepatology Research. 19 (1): 31–40. doi:10.1016/S1386-6346(00)00079-6. ISSN 1386-6346.
  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 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.
  7. ^ Ferrari P, Sansonnens A, Dick B, Frey FJ (December 2001). "In vivo 11beta-HSD-2 activity: variability, salt-sensitivity, and effect of licorice". Hypertension. 38 (6): 1330–6. CiteSeerX 10.1.1.620.857. doi:10.1161/hy1101.096112. PMID 11751713.
  8. ^ 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.
  9. ^ 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.
  10. ^ "Glycyrrhizic Acid". PubChem. National Institutes of Health. Retrieved 24 February 2014.

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Glycyrrhizin&oldid=953024013"