Биапигенин

Description

Biapigenin (3,8'-biapigenin) is a dimeric biflavonoid formed by the bond of two apigenin molecules, a key component of St. John's wort (Hypericum perforatum). The compound has been studied as an inhibitor of protein tyrosine phosphatase 1B (PTP1B, IC50 4.5 μM), stimulating glucose uptake by adipocytes, as well as an inhibitor of cytochrome P450 isoforms CYP3A4, CYP2C9 and CYP1A2, which is important for assessing drug interactions of St. John's wort preparations.

Basic Attributes

• CAS No: 101140-06-1
• Chemical formula: C30H18O10
• Molecular Weight: 538.462
• Exact weight: 538.46
• PSA Specs: 174
• XLogP3: 5

Physico-chemical characteristics

• Density: 1.672±0.06 g/cm3 (predicted value)
• Melting point: 258–260 °C
• Boiling point: 911.7±65.0°C (predicted value)
• Storage conditions: 2–8 °C

Scope of application

Analytical standard for monitoring the content of biapigenin in extracts of St. John's wort and herbal preparations based on it. Reagent for pharmacological research - studying the neuroprotective effect (reducing the death of hippocampal neurons caused by kainate and NMDA), the effect on mitochondrial bioenergetics, as well as anti-inflammatory and gastroprotective activity along with quercetin, the second main component of St. John's wort oil extracts.

Mechanism of action

Inhibits protein tyrosine phosphatase 1B, which stimulates glucose uptake into adipose tissue cells, an area of ​​interest for research into metabolic disorders. Suppresses cytochrome P450 isoforms CYP3A4 (Ki 0.038 µM), CYP2C9 (Ki 0.32 µM) and CYP1A2 (Ki 0.95 µM), which is clinically significant when St. John's wort is taken together with drugs metabolized by these enzymes. Reduces the ability of mitochondria to absorb calcium, affecting the energy metabolism of the cell.

Safety Information

• WGK Germany: 3

Storage and transportation conditions

Store at 2–8 °C, in the original sealed container, protected from light and moisture, since polyphenolic biflavonoids are sensitive to oxidation. Data on UN transport codes and GHS phrases is not provided in the source. When working, use standard laboratory protective equipment.

Synonyms of substance

• [3,8'-Bi-4H-1-benzopyran]-4,4'-dione,5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-
• 5,5',7,7'-Tetrahydroxy-2,2'-bis(4-hydroxyphenyl)[3,8'-bi-4H-1-benzopyran]-4,4'-dione
• I3,II8-Biapigenin
• 3.8"-Biapigenin, 8.3"-Biapigenin

Role in plant and herbal medicine

Biapigenin is formed as a result of oxidative dimerization of apigenin and accumulates in the aerial part of St. John's wort along with hypericin, hyperforin and other phenolic compounds. The content of biapigenin in standardized extracts of St. John's wort is standardized as one of the markers of the quality of raw materials, along with hypericin, since fluctuations in the concentration of active components significantly affect the pharmacological activity of the finished drug.