Wogonin
Chemical compound
From Wikipedia, the free encyclopedia
Wogonin is an O-methylated flavone, a flavonoid-like chemical compound which is found in Scutellaria baicalensis.[2]
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| Names | |
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| 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) |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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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The glycosides of wogonin are known as wogonosides. For example, oroxindin is a wogonin glucuronide isolated from Oroxylum indicum.[3] 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.[2] Preliminary in vitro studies have shown pharmacological effects that indicate wogonin may have anti-tumor properties.[4][5] Wogonin has also been found to possess anticonvulsant effects.[6] It acts as a positive allosteric modulator of the benzodiazepine site of the GABAA receptor with a binding affinity of Ki 0.92 μM and an IC50 value of 1.26 μM which is about 100 times less potent than diazepam (IC50 value of 0.012 μM).[2][6] The LD50 of pure Wogonin in mice is 3.9 g/kg of body weight suggesting low toxicity.[7]
CNS review:[8]