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W0769

Sigma-Aldrich

Wogonin hydrate

≥98% (HPLC), solid

Synonym(s):

5,7-Dihydroxy-8-methoxyflavone

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About This Item

Empirical Formula (Hill Notation):
C16H12O5 · xH2O
CAS Number:
632-85-9
Molecular Weight:
284.26 (anhydrous basis)
MDL number:
MFCD12828871
UNSPSC Code:
12352200
PubChem Substance ID:
329830424
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

O.COc1c(O)cc(O)c2C(=O)C=C(Oc12)c3ccccc3

InChI

1S/C16H12O5.H2O/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;1H2

InChI key

XLCSETHCROERAU-UHFFFAOYSA-N

General description

Wogonin is a flavonoid component of Scutellaria baicalensis Georgi roots.

Application

Wogonin hydrate has been used to enhance the cytotoxicity of oxaliplatin in gastric cancer cells and zebrafish xenograft model and to test its effect on the expression and secretion of adiponectin in mature 3T3-L1 adipocytes.

Biochem/physiol Actions

Wogonin co-treatment enhances apoptosis and antitumor potential of chemotherapeutic drug, oxaliplatin in gastric cancer cells. It also improves the efficacy of fluorouracil and paclitaxel. Wogonin anti-oxidative functionality may be useful in treating neurodegenerative and inflammatory diseases.
Wogonin is an anti-inflammatory agent and COX-2 inhibitor, which inhibits the induction of both iNOS and COX-2. Wogonin inhibits COX-2 (IC50 = 46 μM) without affecting COX-1. Wogonin inhibits iNOS induction and thus inhibts activation-induced C6 glial cell death. Specifically, Wogonin inhibits NF-kappaB-mediated iNOS induction.

Features and Benefits

This compound is featured on the Nitric Oxide Synthases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chiu-Mei Lin et al.
The American journal of Chinese medicine, 40(2), 415-427 (2012-03-16)
Constitutive activation of the Janus kinase (JAK)/signal transducer and activator of transcription (STAT) pathway occurs commonly in cancer cells and endothelial cells, and contributes to angiogenesis. Wogonin is a compound with many biologically relevant properties. We previously reported that wogonin
Matthew F Cusick et al.
Journal of virology, 87(3), 1849-1860 (2012-12-14)
Viral infections of the central nervous system (CNS) can trigger an antiviral immune response, which initiates an inflammatory cascade to control viral replication and dissemination. The extent of the proinflammatory response in the CNS and the timing of the release
Tingqin Yan et al.
Diagnostic pathology, 9, 154-154 (2014-11-30)
Oxidative stress causes the defects of retinal pigment epithelial (RPE) cells that contribute to age-related macular degeneration (AMD). This study was conducted to determine whether wogonin could prevent H2O2-induced oxidative stress in RPE cells. A RPE cell line, ARPE-19, was
Dae-Hee Lee et al.
Cellular signalling, 24(11), 2216-2225 (2012-08-01)
We investigated the molecular basis of the ability of wogonin to control the intracellular signaling cascades of AMP-activated protein kinase (AMPK). This activity induces antitumor activities in glioblastoma multiforme (GBM) cells. Recently, the evolutionarily conserved serine/threonine kinase AMPK has emerged
Xiuming Song et al.
Toxicology and applied pharmacology, 271(2), 144-155 (2013-05-28)
Wogonin, a plant-derived flavone, has been shown recently to have antitumor effects. However, the mechanisms that wogonin inhibits tumor angiogenesis are not well known. In this study, we investigated the effects of wogonin on expression of hypoxia-inducible factor-1α (HIF-1α) and
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