Wogonin

Wogonin is an O-methylated flavone, a flavonoid-like chemical compound which is found in Scutellaria baicalensis.^[2]

Wogonin^[1]

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
CAS Number	632-85-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:10043 N
ChEMBL	ChEMBL16171 N
ChemSpider	4445020 N
KEGG	C10197 N
PubChem CID	5281703
UNII	POK93PO28W Y
CompTox Dashboard (EPA)	DTXSID70212557
InChI 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
SMILES COC1=C(C=C(C2=C1OC(=CC2=O)C3=CC=CC=C3)O)O
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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 GABA_A receptor with a binding affinity of K_i 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]

See also

• Dihydrowogonin