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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:
Molecular Weight:
284.26 (anhydrous basis)
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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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Fei Wang et al.
Toxicology, 305, 10-19 (2012-12-19)
Wogonin, a naturally occurring monoflavonoid extracted from the root of Scutellaria baicalensis Georgi, has been reported for its anti-oxidant activity. However, it is still unclear whether wogonin can inhibit oxidant-induced vascular permeability. In this study, we evaluated the effects of
Yan Zhong et al.
Molecular carcinogenesis, 52(10), 824-834 (2012-05-18)
Acquired resistance to doxorubicin (DOX) is a serious therapeutic problem in breast cancer patients. In this study, we investigated whether nuclear factor erythroid 2-related factor 2 (Nrf2) was associated with drug resistant in DOX resistant MCF-7 (MCF-7/DOX) cells, and if
Meng Zhang et al.
Life sciences, 92(1), 55-62 (2012-11-13)
Wogonin is one of the major constituents derived from Scutellaria Baicalensis, which has been reported to inhibit cell growth and/or induce apoptosis in various cancer cell lines. We aim to investigate the anticancer effects and associated mechanisms of wogonin on
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
Yoshiyuki Kimura et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 20(3-4), 328-336 (2012-12-12)
Tumor growth and metastasis are associated with angiogenesis and lymphangiogenesis through the production of vascular endothelial growth factor (VEGF) or VEGF-C in tumors, and the phosphorylation of VEGF receptor (VEGFR)-2 or VEGFR-3 in vascular endothelial cells or lymphatic endothelial cells

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