WOGONIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12O5
Molecular Weight	284.2635
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C2OC(=CC(=O)C2=C(O)C=C1O)C3=CC=CC=C3

InChI

InChIKey=XLTFNNCXVBYBSX-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H12O5
Molecular Weight	284.2635
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21573491 | https://www.ncbi.nlm.nih.gov/pubmed/12392823 | https://www.ncbi.nlm.nih.gov/pubmed/28646664 | https://www.ncbi.nlm.nih.gov/pubmed/28486193 | https://www.ncbi.nlm.nih.gov/pubmed/26336584

Wogonin is an O-methylated flavone compound isolated from Scutellaria baicalensis. Wogonin is an a positive allosteric modulator of benzodiazepine site of the GABAA ion channel, and displays anxiolytic properties in animal models. It possesses anti-tumor effect in models of osteosarcoma and lung cancer. Hepatoprotective action of wogonin was demonstrated in the mouse model of alcoholic liver disease and in a model of nonalcoholic fatty liver disease, where it was shown that wogonin upregulates PPAR-gamma and PPARalpha respectively. Wogonin possess chondroprotective action which was demonstrated in models of osteoarthritis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12392823	Positive Allosteric Modulator 186
Nitric oxide synthase, inducible 55 Target ID: CHEMBL3464 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22366656	Inhibitor 8504	7.8 µM [IC50]
Cyclooxygenase-2 201 Target ID: CHEMBL4321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19233646	Inhibitor 8504	1.07 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21573491	Primary	Basic research	Unknown Approved Use Unknown
Anxiety 275 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12392823	Primary	Preclinical	Unknown Approved Use Unknown
Alcoholic liver disease 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28646664	Primary	Preclinical	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28486193	Primary	Preclinical	Unknown Approved Use Unknown
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28237856	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25596147	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Difference of growth-inhibitory effect of Scutellaria baicalensis-producing flavonoid wogonin among human cancer cells and normal diploid cell.	2007-01-08	16497434
Simultaneous determination of eight active components in Chinese medicine 'YIQING' capsule using high-performance liquid chromatography.	2007-01-04	16846714
Liquid chromatography with tandem mass spectrometry for the simultaneous determination of baicalein, baicalin, oroxylin A and wogonin in rat plasma.	2006-12-05	16893689
Wogonin sensitizes resistant malignant cells to TNFalpha- and TRAIL-induced apoptosis.	2006-12-01	16931628
Effects of wogonin on the levels of cytokines and functions of leukocytes associated with NF-kappa B expression in Sprague-Dawley rats.	2006-08-12	16900784
Involvement of bax/bcl-2 in wogonin-induced apoptosis of human hepatoma cell line SMMC-7721.	2006-08	16926629
Retention behavior of silica-bonded and novel polymeric reversed-phase sorbents in studies on flavones as chemotaxonomic markers of Scutellaria L. genus.	2006-07-07	16364344
Lipopolysaccharide plus 12-o-tetradecanoylphorbol 13-acetate induction of migration and invasion of glioma cells in vitro and in vivo: Differential inhibitory effects of flavonoids.	2006-06-30	16580779
The anticancer activities of wogonin in murine sarcoma S180 both in vitro and in vivo.	2006-06	16755005
Effects of flavonoids extracted from Scutellaria baicalensis Georgi on hemin-nitrite-H2O2 induced liver injury.	2006-04-24	16574098
[Qualitative and quantitative determination of the main components of huanglianjiedu decoction by HPLC-UV/MS].	2006-04	16856488
[Simultaneous determination of three kinds of components in sanhuang tablets by high-performance liquid chromatography].	2006-03	16759005
Analysis of the interactions of botanical extract combinations against the viability of prostate cancer cell lines.	2006-03	16550232
Micellar electrokinetic chromatography for separation of a mixture of coptis alkaloids, scute flavonoids, and rhubarb anthraquinones and bianthrones.	2006-01-23	16297588
[Determination of contents of the effective ingredients in root of Scutellaria baicalensis by HPLC-ECD].	2006-01	16548169
Application of LC/MS and ICP/MS for establishing the fingerprint spectrum of the traditional Chinese medicinal preparation Gan-Lu-Yin.	2006-01	16485723
Cardioprotective effects of grape seed proanthocyanidins, baicalin and wogonin: comparison between acute and chronic treatments.	2006	16700106
Scutellaria baicalensis decreases ritonavir-induced nausea.	2005-12-20	16368007
[Studies on chemical constituents in bark of dictamnus dasycarpus].	2005-11	16400943
Molecular targets of dietary polyphenols with anti-inflammatory properties.	2005-10-31	16259055
Binding of wogonin to human gammaglobulin.	2005-10-30	16242767
Inhibitory effects of a chemically standardized extract from Scutellaria barbata in human colon cancer cell lines, LoVo.	2005-10-19	16218664
Melatonin, a potent agent in antioxidative defense: actions as a natural food constituent, gastrointestinal factor, drug and prodrug.	2005-09-10	16153306
Skullcapflavone I from Scutellaria baicalensis induces apoptosis in activated rat hepatic stellate cells.	2005-09	16206047
Synthesis and inhibition of PGE2 production of 6,8-disubstituted chrysin derivatives.	2005-09	15963606
Structure and antiinflammatory activity relationships of wogonin derivatives.	2005-08	16178410
Inhibition of prostaglandin production by a structurally-optimized flavonoid derivative, 2',4',7-trimethoxyflavone and cellular action mechanism.	2005-08	16079475
Interaction of wogonin with bovine serum albumin.	2005-06-02	15911327
Synthesis and iNOS inhibitory activities of thioflavones.	2005-06	16042072
Non-aqueous capillary electrophoresis for simultaneous separation and determination of three major active components in traditional medicinal preparations.	2005-06	15627280
Characterization of chemical constituents in Scutellaria baicalensis with antiandrogenic and growth-inhibitory activities toward prostate carcinoma.	2005-05-15	15897592
Isolation and purification of baicalein, wogonin and oroxylin A from the medicinal plant Scutellaria baicalensis by high-speed counter-current chromatography.	2005-05-13	15941045
Enhancing effects of Scutellaria baicalensis and some of its constituents on TGF-beta1 gene expression in RAW 264.7 murine macrophage cell line.	2005-05	15931583
Baicalein, a component of Scutellaria radix from Huang-Lian-Jie-Du-Tang (HLJDT), leads to suppression of proliferation and induction of apoptosis in human myeloma cells.	2005-04-15	15626742
Wogonin inhibits N-acetyltransferase activity and gene expression in human leukemia HL-60 cells.	2005-04-09	15816529
Synthetic wogonin derivatives suppress lipopolysaccharide-induced nitric oxide production and hydrogen peroxide-induced cytotoxicity.	2005-02	15789754
The herbal medicine Sho-saiko-to selectively inhibits CD8+ T-cell proliferation.	2005-01-10	15659321
Suppression of cyclooxygenase-2 expression of skin fibroblasts by wogonin, a plant flavone from Scutellaria radix.	2005-01	15589400
Therapeutic potential of wogonin: a naturally occurring flavonoid.	2005	16007236
Separation methods used for Scutellaria baicalensis active components.	2004-12-05	15556504
Efficacy of wogonin in the production of immunoglobulins and cytokines by mesenteric lymph node lymphocytes in mouse colitis induced with dextran sulfate sodium.	2004-12	15618621
A metabolomic analysis of medicinal diversity in Huang-qin (Scutellaria baicalensis Georgi) genotypes: discovery of novel compounds.	2004-11	15449017
Wogonin inhibits ischemic brain injury in a rat model of permanent middle cerebral artery occlusion.	2004-10	15467195
[Isolation and elucidation of antioxidant constituents from acetone extract in root of Scutellaria rehderiana].	2004-09	15575204
Neuroprotective effect of wogonin: potential roles of inflammatory cytokines.	2004-09	15473663
Neuroprotective effect of wogonin in hippocampal slice culture exposed to oxygen and glucose deprivation.	2004-06-16	15189769
Suppression of nitric oxide production in mouse macrophages by soybean flavonoids accumulated in response to nitroprusside and fungal elicitation.	2004-04-21	15102332
Inhibition of contact dermatitis in animal models and suppression of proinflammatory gene expression by topically applied flavonoid, wogonin.	2004-04	15180311
Preventive effect of the flavonoid, wogonin, against ethanol-induced gastric mucosal damage in rats.	2004-03	15139485
Proteomic analysis of mouse liver for the evaluation of effects of Scutellariae radix by liquid chromatography with tandem mass spectrometry.	2004	15468106

Patents

Sample Use Guides

In Vivo Use Guide

In tests of anxiolytic action, wogonin was administered to mice orally and displayed an effect at 7.5-30 mg/kg. In the study of anticonvulsant effect, wogonin was administered to rats intraperitoneally.

Route of Administration: Other

In Vitro Use Guide

In vitro electrophysiological studies were performed on freshly isolated DRG neurons from adult rats. Whole-cell patch-clamp recordings were performed at room temperature. The membrane potential was held at -60 mV. GABA was dissolved in the extracellular solution. Wogonin was dissolved in DMSO and further diluted by the extracellular solution. The GABA-activated current was enhanced by the co-application with GABA and wogonin (10 uM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:16:21 GMT 2025` Edited by `admin` on `Mon Mar 31 19:16:21 GMT 2025`
Record UNII	POK93PO28W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-8-METHOXY-2-PHENYL-

Preferred Name

English

WOGONIN

Official Name

English

5,7-DIHYDROXY-8-METHOXYFLAVONE

Systematic Name

English

FLAVONE, 5,7-DIHYDROXY-8-METHOXY-

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

WOGONIN