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Anticonvulsant
Wogonin
Другие языки:

Wogonin

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Wogonin
Skeletal formula
Ball-and-stick model
Names
IUPAC name
5,7-Dihydroxy-8-methoxyflavone
Systematic IUPAC name
5,7-Dihydroxy-8-methoxy-2-phenyl-4H-1-benzopyran-4-one
Other names
Vogonin
Norwogonin 8-methyl ether
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3 ☒N
    Key: XLTFNNCXVBYBSX-UHFFFAOYSA-N ☒N
  • InChI=1/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3
    Key: XLTFNNCXVBYBSX-UHFFFAOYAQ
  • COC1=C(C=C(C2=C1OC(=CC2=O)C3=CC=CC=C3)O)O
Properties
C16H12O5
Molar mass 284.267 g·mol−1
Melting point 203 to 206 °C (397 to 403 °F; 476 to 479 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Wogonin is an O-methylated flavone, a flavonoid-like chemical compound which is found in Scutellaria baicalensis.

The glycosides of wogonin are known as wogonosides. For example, oroxindin is a wogonin glucuronide isolated from Oroxylum indicum. It is one of the active ingredients of Sho-Saiko-To, a Japanese herbal supplement.

Pharmacology

Wogonin has been found in one study to have anxiolytic properties in mice at doses of 7.5 to 30 mg/kg, without exhibiting the sedative and muscle-relaxing properties of benzodiazepines. Preliminary in vitro studies have shown pharmacological effects that indicate wogonin may have anti-tumor properties. Wogonin has also been found to possess anticonvulsant effects. It acts as a positive allosteric modulator of the benzodiazepine site of the GABAA receptor with an binding affinity of Ki 0.92μM and an IC50 value of 1.26μM which is about 100x less potent than Diazepam (IC50 value of 0.012μM). The LD50 of pure Wogonin in mice is 3.9g (grams) per kilogram of body weight suggesting low toxicity



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