Ангефлорин

Substance identification

Angeflorin is a flavonoid glycoside, 7,4'-di-O-methylscutellarin 6-beta-D-glucopyranoside. CAS number 57498-69-8, formula C23H24O11.

Physico-chemical characteristics

• Molecular weight: 476.43
• Exact weight: 476.13186158
• PSA Specifications: 168.28
• XLogP3: 0.3615

Plant source and substance class

Angeflorin is a natural product found in plants of the genus Heracleum (hogweed, Apiaceae family). Structurally, it belongs to the class of flavone glycosides - a derivative of scutellarein (5,6,7,4'-tetrahydroxyflavone), dimethylated at positions 7 and 4' and glycosylated with glucose at position 6.

Class of scutellarein glycosides

Scutellarein (5,6,7,4'-tetrahydroxyflavone) is a flavone found in plants of the genera Scutellaria (scutellaria), Heracleum and a number of other taxa; the combination of methylation and glycosylation characteristic of angeflorin is a typical strategy for natural flavonoids to simultaneously increase metabolic stability (methoxy groups are less susceptible to rapid oxidative metabolism than free hydroxyls) and water solubility (glycosidic residue). Such di-O-methylated scutellarein monoglucosides have been described in several Apiaceae species as minor components of the flavonoid profile.

Genus Heracleum

The genus Heracleum (hogweed) of the Umbrella family includes several dozen species, among which the most famous for their phototoxicity are Sosnowsky's hogweed (Heracleum sosnowskyi) and Mantegazzi's hogweed (Heracleum mantegazzianum) - their juice contains furanocoumarins, which cause severe photochemical burns of the skin upon contact with UV light. Along with furanocoumarins, the tissues of plants of the genus contain flavonoid glycosides, including angeflorin, which contribute to the antioxidant properties of plant materials.

Scope of application

Used as an analytical standard in phytochemical studies of plants of the genus Heracleum and in studies of flavonoid glycosides of plant origin. It is not produced on an industrial scale; it is supplied as a reagent for scientific laboratories with confirmation of purity.

Biosynthesis and biological significance of the class

The flavone skeleton of scutellarein, like other flavones, is biosynthesized in plants from naringenin (a condensation product of the phenylpropanoid and polyketide pathways) by sequential reactions of hydroxylation and desaturation of the C ring; further O-methylation and glycosylation of hydroxyl groups, leading to the structure of angeflorin, are typical biochemical modification pathways for flavonoids, determining the solubility, stability and bioavailability of the final compound. Flavones of the scutellarein series have generally been studied as compounds with antioxidant and anti-inflammatory activity.

Storage

As a solid flavonoid glycoside, sensitive to oxidation and light, it is stored in a sealed container protected from light at a low temperature, under conditions that exclude moisture.