Дегидроглиасперин С

Identification

Dehydroglyasperin C (CAS 199331-35-6) is a natural prenylflavonoid. Chemical formula C21H22O5. Systematic name by synonym: 4-[7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-3-yl]-1,3-benzenediol. UNII: 80H8MSZ44I.

Physico-chemical characteristics

• Molecular Weight: 354.39638
• Exact weight: 354.147
• UNII: 80H8MSZ44I
• PSA characteristic: 79.2 Ų
• XLogP3: 4.3

There are no other parameters - density, melting points, boiling points, refractive index - in the original dump for this product, and they were not found in open sources during an additional search.

Natural spring

Isolated from Ural licorice (Glycyrrhiza uralensis). Along with dehydroglasperin D, it is one of the most studied prenylflavonoids of the genus Glycyrrhiza, recognized as a powerful inducer of phase II detoxification enzymes and antioxidant enzymes.

Anti-smooth muscle cell proliferation activity

Attenuates proliferation and migration of human arterial smooth muscle cells induced by platelet-derived growth factor (PDGF), a process underlying atherosclerosis and vascular restenosis after angioplasty.

Neuroprotective activity

In HT22 mouse hippocampal cells, dehydrogliasperin C dose-dependently reduces glutamate-induced cytotoxicity and reactive oxygen species production by inducing the expression of heme oxygenase-1 (HO-1), one of the main components of cellular antioxidant defense. The compound also attenuates the phosphorylation of signaling proteins and reduces the DNA binding activity of the NF-κB factor in microglia stimulated by lipopolysaccharide, reducing the production of the pro-inflammatory cytokine TNF-α.

Induction of detoxification enzymes

Through the Nrf2 pathway, it induces a number of phase II detoxification and antioxidant defense enzymes: glutathione S-transferase, gamma-glutamylcysteine ​​synthetase, glutathione reductase, and heme oxygenase-1—a complex cellular response to oxidative and electrophilic stress.

Place among licorice prenylflavonoids

Dehydrogliasperin C is one of the most studied prenylflavonoids of the genus Glycyrrhiza, along with dehydrogliasperin D, licochalcone A and glabridin. The uniqueness of the compound lies in the combination of three directions of biological activity at once: vascular, neuroprotective and general cellular detoxifying, which is rarely found in one natural phenolic compound of the same class.

Structural features

The systematic name refers to the prenyl (3-methyl-2-butenyl) substituent at position 6 of the chromane ring and the methoxy group at position 5—an architecture typical of licorice prenylflavonoids, combining a polyphenolic core with a lipophilic side chain that facilitates the penetration of the molecule through cell membranes.

Storage

Licorice prenylflavonoids are sensitive to oxidation and light. Store in a container protected from light, in a cool, dry place.