Изоангустон А

Description

Isoangustone A is a prenylated isoflavone from licorice root (Glycyrrhiza uralensis and related species). Structure: 4H-chromen-4-one with hydroxyls at positions 5 and 7, a prenyl group at position 6 and an aryl substituent at position 3, which itself carries two hydroxyl groups and a second prenyl moiety. Two isoprene chains explain the high lipophilicity of the compound.

Basic Attributes

• CAS No: 129280-34-8
• Chemical formula: C25H26O6
• Molecular Weight: 422.47034
• Exact weight: 422.47
• PSA Specifications: 107
• XLogP3: 6.2
• Melting point: 191–193 °C
• Systematic name: 3-[3,4-dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl]-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one

Activity studied

• suppression of human melanoma cell proliferation through targets PI3K, MKK4 and MKK7
• induction of autophagic death of colorectal cancer cells with activation of the AMPK signaling pathway
• suppression of fibrosis and inflammation in human kidney mesangial cells
• anti-inflammatory and antioxidant effects

Receipt

Isolated from a hexane-ethanol extract of the root of Glycyrrhiza uralensis. This extract contains virtually no glycyrrhizin, the main component of dry licorice root, long-term use of which is associated with hypertension and hypokalemia. Isoangustone A allows one to study the activity of licorice separately from the glycyrrhizin fraction.

Scope of application

Oncological cell models, work on the PI3K and MAPK signaling cascades, nephrological studies of fibrosis, standard sample for the analysis of the flavonoid fraction of licorice.

Storage and handling

There is no GHS classification. Crystalline powder, melting 191–193 °C. An XLogP3 value of 6.2 means practical insolubility in water—stock solutions are prepared in DMSO. Store in a closed container, away from light and moisture; work with gloves and glasses.