Глабранин

Description

Glabranin is a prenylated flavonoid of a number of flavanones of plant origin. According to the chemical nomenclature - (S)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-phenylchroman-4-one, that is, a flavanone with two hydroxyls at C5 and C7 of the chromane ring and a prenyl (3-methylbut-2-enyl) substituent at C8. Isolated from plants of the genus Dalea (in particular Dalea elegans), Tephrosia and from the roots of licorice Glycyrrhiza uralensis, where it is found along with other prenylated flavonoids.

Basic Attributes

• CAS No.: 41983-91-9
• Chemical formula: C20H20O4
• English name: Glabranin (Glabranine)
• Section: flavonoids
• Molecular Weight: 324.3704
• Exact weight: 324.37
• DSSTox ID: DTXSID00194796
• PSA specifications: 66.8
• XLogP3: 6.02

Physico-chemical characteristics

• Density: 1.2±0.1 g/cm3
• Boiling point: 545.9±50.0 °C at 760 mm Hg. Art.
• Flash point: 197.1±23.6°C

Synonyms

• 4H-1-Benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-buten-1-yl)-2-phenyl-,(2S)-
• Glabranine
• (2S)-2,3-Dihydro-5,7-dihydroxy-8-(3-methyl-2-buten-1-yl)-2-phenyl-4H-1-benzopyran-4-one
• Glabranin (flavonoid)

Biological activity and applications

Glabranin has been studied in a number of areas of biological activity of natural prenylated flavonoids. Pronounced activity against dengue virus (DENV) has been shown - the compound interacts with the soluble ectodomain of the envelope protein E of DENV type 2 and is considered as a promising scaffold for the development of antiviral drugs of the flavivirus group. Antimicrobial effects, antioxidant activity according to the DPPH test (IC50 240.2 μg/ml), a neuroprotective effect due to inhibition of the GSK-3β enzyme and protection of cerebellar neurons from oxidative stress in vitro, as well as a stimulating effect on hair growth are also described. The presence of a prenyl substituent at C8 is considered key for the biological activity of the flavone scaffold.

Storage and transportation

Data on GHS hazard classification and transport codes have not been published by manufacturers. Store as an analytical and research reagent in a cool, dry place, in the original sealed container, protected from light; a flash point of 197.1 ± 23.6 °C indicates a moderate fire hazard with significant heating.

Related prenylated flavonoids

In the roots of licorice Glycyrrhiza uralensis, glabranin is accompanied by other prenylated flavonoids involved in the differentiation of B16-F10 melanoma cells in in vitro studies. In the species Erythrina and Tephrosia, a series of prenylated flavones and flavanones, similar in structure, has been described, where the position and number of prenyl substituents determine the spectrum of biological activity - from antiviral to antimicrobial. This diversity makes prenylated flavonoids a promising source of new biologically active molecules for pharmaceutical development.