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W0769

Sigma-Aldrich

Wogonin hydrate

≥98% (HPLC), solid

Synonyme(s) :

5,7-Dihydroxy-8-methoxyflavone

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About This Item

Formule empirique (notation de Hill):
C16H12O5 · xH2O
Numéro CAS:
632-85-9
Poids moléculaire :
284.26 (anhydrous basis)
Numéro MDL:
MFCD12828871
Code UNSPSC :
12352200
ID de substance PubChem :
329830424
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

solid

Solubilité

DMSO: ≥20 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

XLCSETHCROERAU-UHFFFAOYSA-N

Description générale

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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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
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
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
Roman G Szafran et al.
Molecules (Basel, Switzerland), 26(11) (2021-06-03)
To study the simultaneous effect of the molecular gradient of polyphenols (curcumin, trans-resveratrol, and wogonin) and biological factors released from tumor cells on apoptosis of adjacent cells, a novel microfluidic system was designed and manufactured. The small height/volume of microfluidic
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
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