Ганкаонин М

Description

Gankaonin M is a prenylated isoflavone isolated from the roots of Ural licorice (Glycyrrhiza uralensis Fisch.). Belongs to the group of preoxylated licorice flavonoids, along with homologues Gankaonin G, I and N. The name is derived from the Chinese name for licorice - “gancao”.

Identification

• English name: Gancaonin M
• CAS No: 129145-51-3
• Chemical formula: C21H20O5
• Systematic name: 5,7-dihydroxy-3-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
• Synonyms according to IUPAC nomenclature: 4H-1-Benzopyran-4-one,5,7-dihydroxy-3-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-

Physico-chemical characteristics

• Molecular Weight: 352.3805
• Exact weight: 352.38
• Density: 1.277 g/cm3
• Melting point: 139–141 °C (in solvent: diethyl ether, hexane)
• Boiling point: 560.679 °C at 760 mm Hg. Art.
• Flash point: 199.473 °C
• Refractive index: 1.629
• Solubility in water: 0.2753 mg/l at 25 °C (calculated)
• Vapor pressure: close to 0 mmHg. Art. at 25 °C
• PSA Specifications: 76
• XLogP3: 4.9

Substance class and biological activity

Gankaonin M is a representative of prenylated isoflavones, the active substances of licorice root. The side prenyl (3-methylbut-2-enyl) group increases the lipophilicity of the molecule (XLogP3 4.9) and enhances membranotropy, due to which the compounds of this series exhibit antibacterial and anti-inflammatory activity. Homologues of this group—Gankaonin G, I, N—were studied in models of acute inflammation and bacterial infections, where they showed a decrease in the production of proinflammatory mediators through suppression of the NF-κB/MAPK signaling pathway.

Scope of application

It is used as a reference substance and object of pharmacological studies of the biologically active substances of licorice. Supplied as a powder with an HPLC purity of at least 98% for laboratories studying the antibacterial and anti-inflammatory properties of prenylated flavonoids, as well as for the standardization of Glycyrrhiza uralensis extracts.

Storage and transportation

White powder, poorly soluble in water (0.2753 mg/l), with extremely low vapor pressure - no losses are expected under normal storage conditions. Store in an airtight container in a cool, dry place, protected from direct light, away from sources of moisture. When transporting, special temperature conditions are not required; it is important to avoid contact with moisture and overheating above 139 °C.

Related compounds of licorice

Gankaonin M is a member of the family of prenylated isoflavones of Glycyrrhiza uralensis along with Gankaonin G (CAS 126716-34-5), Gankaonin I (CAS 126716-36-7) and Gankaonin N (CAS 129145-52-4), as well as the structurally related Gankaonin L (CAS 129145-50-2). Homologues differ in the position of the prenyl group and the degree of hydroxylation of the aromatic rings, which determines the range of their biological activity - from antibacterial to anti-inflammatory. In phytochemical profiling of licorice root, Gankaonin M is usually quantitatively recorded together with these compounds by HPLC-MS to assess the identity and origin of the raw material.