Glycyrrhizin

Chembox new
Name = Glycyrrhizin
ImageFile = glycyrrhizin.png ImageSize = 300px
ImageName = Glycyrrhizin
IUPACName =(3-β,20-β)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl
2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid
OtherNames = Glycyrrhizin
Glycyrrhizinic acid
Glycyrrhizic acid
Section1 = Chembox Identifiers
CASNo = 1405-86-3
EINECS = 215-785-7
SMILES = OC1C(O)C(O)C (OC2C(O)C(O)C (C(O)=O)OC2OC3 [C@]
(C)(C) [C@@] (CC [C@] ( [C@@] (CC [C@] 7(C) [C@@]
( [H] )6C [C@@] (C)(C(O)=O)CC7) (C)C6=C5)(C) [C@@] ( [H] )4
C5=O) ( [H] ) [C@] 4(C) CC3)OC1C(O)=O
ATCCode_prefix=A05
ATCCode_suffix=BA08
ATC_Supplemental = [cite web |url=http://www.whocc.no/atcddd/new_atc_ddd.html#ATCDDD_FINAL |title=ATC/DDD Classification (FINAL): New ATC 5th level codes |date=August 27, 2008 |author=WHO International Working Group for Drug Statistics Methodology |publisher=WHO Collaborating Centre for Drug Statistics Methodology |accessdate=2008-09-05]
Section2 = Chembox Properties
Formula = C₄₂H₆₂O₁₆
MolarMass = 822.94 g/mol
Density =
MeltingPt =

Glycyrrhizin is the active principle of liquorice root. It is a powerful sweetener, 30–50 times as potent as sucrose (table sugar).

Chemically, glycyrrhizin is a triterpenoid saponin glycoside being either the Ca2+ or K+ salt of glycyrrhizic (or glycyrrhi"zinic") acid. [ [http://www.friedli.com/herbs/phytochem/glycosides.html#saponin Saponin Glycosides] , by Georges-Louis Friedli, URL accessed Dec 2007.] Upon hydrolysis, the glycoside loses its sweet taste and is converted to the aglycone glycyrrhetinic acid plus two molecules of glucuronic acid. The acid form is not particularly water soluble, but its ammonium salt is soluble in water at pH greater than 4.5.

Although sweet, the taste of glycyrrhizin is different from that of sugar. The sweetness of glycyrrhizin has a slower onset than sugar, and lingers in the mouth for some time. Additionally, its characteristic licorice flavor makes it unsuitable as a direct flavor substitute for sugar. Unlike the artificial sweetener aspartame, glycyrrhizin maintains its sweetness under heating.

In the United States, glycyrrhizin is classified as "generally recognized as safe" as a flavoring agent, although not as a sweetener. Glycyrrhizin is used as a flavoring in some candies, pharmaceuticals, and tobacco products.

The European Union suggests that people should not consume any more than 100mg of glycyrrhizic acid a day, [ [http://ec.europa.eu/food/fs/sc/scf/out186_en.pdf Opinion of the Scientific Committee on Food on Glycyrrhizinci Acid and its Ammonium Salt (opinion expressed on 4 April 2003)] , European Commission, 4 April 2003, accessed online 7 June 2008] , equivalent to approximately 50g of liquorice sweets. [cite journal |title = Glycyrrhizic acid in liquorice - evaluation of health hazard
last = Størmer|first = FC |coauthors = Reistad R, Alexander J. | url=http://www.ncbi.nlm.nih.gov/pubmed/8386690 |journal = Food Chem Toxicol | year = 1993 | volume = 31 | issue = 4 | pages = 303–12 | accessdate = 2008-06-07 |doi = 10.1016/0278-6915(93)90080-I]

In Japan, where concern over the safety of artificial sweeteners during the 1970s led to a shift towards plant-derived sugar substitutes, glycyrrhizin is a commonly used sweetener, often used in combination with another plant-based sweetener, stevia. However, glycyrrhizin appears to have some pharmacological side effects, and the Japanese government has asked its citizens to limit their consumption to 200 milligrams per day.

Health effects

The most widely reported side effects of glycyrrhizin use are hypertension and edema (water retention). These effects are related to the inhibition of cortisol metabolism within the kidney, and the subsequent stimulation of the mineralocorticoid receptors. [cite journal |title = In vivo 11beta-HSD-2 activity: variability, salt-sensitivity, and effect of licorice |last = Ferrari|first = P |coauthors = at al | pmid = 11751713 |journal = Hypertension | year = 2001 | volume = 38 | issue = 6 | pages = 1330–6 |doi = 10.1161/hy1101.096112] Thus, consumption of black licorice can mimic disorders of excess aldosterone.

Glycyrrhizin and other licorice root products have been used for numerous medical purposes, particularly treatment of peptic ulcers and as an expectorant. The triterpene derivative of hydrolyzed glycyrrhizin, glycyrrhetinic acid, is itself effective in treatment of peptic ulcer.Fact|date=March 2008

Although licorice may produce anti-inflammatory effects, it is uncertain whether that is due to glycyrrhizin, glycyrrhetinic acid, or some other licorice derivative.

Recently researchers have demonstrated that doses of licorice root extract, delivering the constituent glycyrrhizin in amounts similar to that contained in standard medical doses of the root, rapidly and significantly lowered levels of circulating testosterone in males. [ [http://medherb.com/Materia_Medica/Glycyrrhiza_-_Licorice_root_and_testosterone.htm Glycyrrhiza: Licorice root and testosterone] ]

Glycyrrhizin inhibits liver cell injury caused by many chemicals and is used in the treatment of chronic hepatitis and cirrhosis in Japan. It also inhibits the growth of several DNA and RNA viruses, inactivating herpes simplex virus particles irreversibly. [Nature. 1979 Oct 25;281(5733):689-690.]

ee also

* Glycyrrhetinic acid

References