A flavonoid with diverse biological activities
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Isomer(s)
19843Baicalin
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Apigenin 7-O-Glucuronide (hydrate)

Item No. 33754

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
β-D-glucopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl, hydrate
Molecular Formula
C21H18O11 • XH2O
Formula Weight
446.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
270, 335 nm
SMILES
O=C1C2=C(O)C=C(O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)C(O)=O)C=C2OC(C4=CC=C(C=C4)O)=C1.O
InChi Code
InChI=1S/C21H18O11.H2O/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29;/h1-7,16-19,21-23,25-27H,(H,28,29);1H2/t16-,17-,18+,19-,21+;/m0./s1
InChi Key
XODLIZARORJIDL-ZSESPEEFSA-N
Origin
Plant/Ixeris sonchifolia
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Apigenin 7-O-glucuronide is a flavonoid that has been found in J. sigillata and has diverse biological activities.1,2,3,4 It inhibits matrix metalloproteinase-3 (MMP-3), MMP-8, MMP-9, and MMP-13 (IC50s = 12.87, 22.39, 17.52, and 0.27 μM, respectively).1,2,3,4 Apigenin 7-O-glucuronide also inhibits protein tyrosine phosphatase 1B (PTP1B), acetylcholinesterase (AChE), and aldose reductase with IC50 values of 7.14, 62.96, and 107.1 µM, respectively.2,3 It inhibits LPS-induced production of nitric oxide, prostaglandin E2 (PGE2; Item No. 14010), and TNF-α in RAW 264.7 cells when used at a concentration of 100 µM.4 Apigenin 7-O-glucuronide (5 or 10 mg/kg) improves survival in a mouse model of septic shock induced by LPS.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Crasci, L., Basile, L., Panico, A., et al. Correlating in vitro target-oriented screening and docking: Inhibition of matrix metalloproteinases activities by flavonoids. Planta Med. 83(11), 901-911 (2017).

    2. Nguyen, D.H., Seo, U.M., Zhao, B.T., et al. Ellagitannin and flavonoid constituents from Agrimonia pilosa ledeb. with their protein tyrosine phosphatase and acetylcholinesterase inhibitory activities. Bioorg. Chem. 72, 293-300 (2017).

    3. Yoo, N.H., Jang, D.S., Yoo, J.L., et al. Erigeroflavanone, a flavanone derivative from the flowers of Erigeron annuus with protein glycation and aldose reductase inhibitory activity. J. Nat. Prod. 71(4), 713-715 (2008).

    4. Hu, W., Wang, X., Wu, L., et al. Apigenin-7-O-β-D-glucuronide inhibits LPS-induced inflammation through the inactivation of AP-1 and MAPK signaling pathways in RAW 264.7 macrophages and protects mice against endotoxin shock. Food Funct. 7(2), 1002-1013 (2016).