A flavonoid with anti-inflammatory and anticancer activities
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Parent Compound(s)
14248Wogonin
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Wogonoside

Item No. 29332

Technical Information
Formal Name
5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl β-D-glucopyranosiduronic acid
CAS Number
51059-44-0
Synonyms
  • Wogonin 7-β-D-Glucuronide
  • Wogonin 7-O-β-D-Glucuronide
Molecular Formula
C22H20O11
Formula Weight
Purity
≥98%
A solid
DMF: 5mg/mLDMSO: 15mg/mLPBS (pH 7.2): 2mg/mL
λmax
275 nm
SMILES
O=C(C1=C(O)C=C(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O2)C(OC)=C1O3)C=C3C4=CC=CC=C4
InChi Code
InChI=1S/C22H20O11/c1-30-18-13(32-22-17(27)15(25)16(26)20(33-22)21(28)29)8-11(24)14-10(23)7-12(31-19(14)18)9-5-3-2-4-6-9/h2-8,15-17,20,22,24-27H,1H3,(H,28,29)/t15-,16-,17+,20-,22+/m0/s1
InChi Key
LNOHXHDWGCMVCO-NTKSAMNMSA-N
Origin
Plant/Scutellaria baicalensis Georgi
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    Product Description

    Wogonoside is an active metabolite of wogonin (Item No. 14248) and a flavonoid that has been found in S. baicalensis and has anti-inflammatory and anticancer activities.1,2,3 It decreases the levels of IL-1β, TNF-α, and IL-6 and inhibits the activation of NF-κB and the NOD-, LRR-, and pyrin domain-containing protein 3 (NLRP3) inflammasome in THP-1 cells differentiated with phorbol 12-myristate 13-acetate (PMA; Item No. 10008014).1 Wogonoside (25 and 50 mg/kg) decreases colonic pathological damage and the activity of myeloperoxidase and inducible nitric oxide synthase (iNOS), as well as inhibits NF-κB and NLRP3 inflammasome activation in the colon in a mouse model of colitis induced by dextran sulfate sodium (Item No. 23250). It inhibits phosphorylation of the mammalian target of rapamycin (mTOR), as well as inhibits the growth of (IC50 = 133.9 µM), and induces autophagy in, MDA-MB-231 breast cancer cells.2 Wogonoside (50-100 µM) inhibits tube formation by human umbilical vein endothelial cells (HUVECs) and increases Wnt3a levels and β-catenin phosphorylation in MCF-7 cells and reduces tumor growth and angiogenesis in an MCF-7 mouse xenograft model when administered at a dose of 80 mg/kg.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sun, Y., Zhao, Y., Yao, J., et alWogonoside protects against dextran sulfate sodium-induced experimental colitis in mice by inhibiting NF-κB and NLRP3 inflammasome activation. Biochem. Pharmacol. 94(2), 142-154 (2015).

    2. Sun, Y., Zou, H., Hu, C., et alWogonoside induces autophagy in MDA-MB-231 cells by regulating MAPK-mTOR pathway. Food. Chem. Toxicol. 51, 53-60 (2013).

    3. Huang, Y., Zhao, K., Hu, Y., et alWogonoside inhibits angiogenesis in breast cancer via suppressing Wnt/β-catenin pathway. Mol. Carcinog. 55(11), 1598-1612 (2016).