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Glycyrrhizinic Acid

We offer about 100 synthetical derivatives of Glycyrrhizin that are new and might be biologically active. You can download SD file containing the structures.

Glycyrrhizin is a triterpenoid saponin found in Glychyrrhiza glabra (licorice). Chemically, glycyrrhizin is a sulphated polysaccharide named (3-beta,20-beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid. It is considered to the active constituent of the drug and the standardization of licorice is based on glycyrrhizin content. The standardized extracts of licorice sold in the market contain 20% of glychrrhizin. Glycyrrhizin is converted into glychyrrhetic acid by an enzyme, glycaronidase.

It's not water-soluble, but its ammonium salt is very soluble in water. It is a powerful sweetener, 30-50 times as potent as sucrose (table sugar). Although sweet, the taste of glycyrrhizin is different from that of sugar. Glycyrrhizin's sweetness has a slower onset than sugar's, 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 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. 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.

Pharmacological activities

Licorice root has been used since ancient Egyptian, Greek, and Roman times in the West and in ancient China in the East. Glycyrrhiza uralensis Fisher is a common medicinal herb and crude drug in the traditional Chinese medicine used for over 1000 years [1-3]. The main bioactive components of licorice root is triterpenoid glycoside Glycyrrhizic acid (GA) to be 3-O-[β-D-gluronopyranosyl-(1->2)-β-D-glucuronopyranoside of 18β-Glycyrrhetinic acid, and its aglycone and the major metabolite, Glycyrrhetinic acid (GLA). Both compounds possesses a great variety of pharmacological and biological properties such as anti-inflammatory, anti-ulcerogenic, anti-allergic, anti-oxidant, anti-hepatotoxic, anti-tumor, and antiviral activities [3-5]. GL is one of the first lead natural glycosides used for the treatment of HIV infection and chronic hepatitis B and C [6-8]. GLA derivative to be 3-O-hemisuccinate of GLA disodium salt (carbenoxolone) has been used for the treatment of gastric ulcers[3,5]. GLA was shown high anticancer activity on skin tumors and possesses antileukaemic activity [5,7]. Novel 2-cyano substituted analogues of GLA, namely, methyl 2-cyano-3,11-dioxo-18β-olean-1,12-dien-30-oate (β-CDODA-Me) and methyl 2-cyano-3,11-dioxo-18α-olean-1,12-dien-30-oate (α-CDODA-Me) were potent peroximase proliferators-activated receptor γ agonists in colon cancer cells [8].

1. Shibata S.. A drug over the millennia: pharmacognosy, chemistry, and pharmacology of licorice. // J. Pharm. Soc. Japan, 2000, 120, 849-862.
2. Kitagawa I. Licorice root. A natural sweetener and an important ingredient in Chinese medicine. // Pure Appl. Chem., 2002, 74, 1189-1198.
3. Tolstikov G.A., Baltina L.A., Grankina V.P., Kondratenko R.M., Tolstikova T.G. Licorice: biodiversity, chemistry, and application in medicine. Novosibirsk: Academic Publishing House "Geo", 2007. 311 p.
4. Tolstikov G.A., Baltina L.A., Shults E.E., Pokrovskyi A.G. Glycyrrhizic Acid. // Russian J. Bioorg. Chem., 1997, 23, 625-642.
5. Tolstikov G.A., Baltina L.A., Serdyuk N.G.. Glycyrrhetic acid. // Pharm. Chem. J., 1998, 32, 5-14.
6. Iino S., Tango T., Matsushima T., Toda G., Miyake K., Huno K., Kumada H., Yasuda K., Kuroki T., Hirayama C., Suzuki H. Therapeutic effects of Stronger neo-minophagen C at different doses on chronic hepatitis and liver cirrosis. // Hepatology Res., 2001, 19, 31-40.
7. Logemann W., Lauria F. Antileukaemic activity of Glycyrrhetic acid. // Nature, 1990, 187, 607-608.
8. Chintharlapalli S., Papineni S., Jutooru I., McAlees A., Safe S. Structure-dependent activity of Glycyrrhetinic acid derivatives as peroxisome proliferators-activated receptor γ agonists in colon cancer cells. // Mol. Cancer Ther., 2007, 6, 1588-1598.