A flavonoid with diverse biological activities
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Eupatilin

Item No. 19601

Technical Information
Formal Name
2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one
CAS Number
22368-21-4
Synonyms
  • NSC 122413
Molecular Formula
C18H16O7
Formula Weight
Purity
≥98%
A solid
DMF: 50 mg/mlDMSO: 33 mg/ml
λmax
214, 242, 274, 337 nm
SMILES
O=C1C2=C(O)C(OC)=C(O)C=C2OC(C3=CC=C(OC)C(OC)=C3)=C1
InChi Code
InChI=1S/C18H16O7/c1-22-12-5-4-9(6-14(12)23-2)13-7-10(19)16-15(25-13)8-11(20)18(24-3)17(16)21/h4-8,20-21H,1-3H3
InChi Key
DRRWBCNQOKKKOL-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Eupatilin is a flavonoid that has been found in Artemisia and has diverse biological activities.1,2,3,4,5 It inhibits cell growth in A375 melanoma cells when used at concentrations ranging from 25 to 800 µM.1 Eupatilin binds to peroxisome proliferator-activated receptor α (PPARα; IC50 = 1.18 µM) and induces reporter gene expression in CV-1 cells expressing human PPARα, but not PPARγ, when used at concentrations ranging from 10 to 300 µM.2 It prevents hydrogen peroxide-induced disruption of the F-actin cytoskeleton and inhibition of cell migration in AGS gastric epithelial cells.6 Eupatilin also inhibits 5-lipoxygenase (5-LO) activity in cultured mastocytoma cells (IC50 = 14 µM).3 In vivo, eupatilin (5, 10, and 15 mg/kg) reduces pulmonary edema and levels of the lung injury markers surfactant protein A (SPA) and SPD in a rat model of LPS-induced acute lung injury.4 It reduces serum levels of histamine and increases survival in a mouse model of allergic anaphylactic shock induced by compound 48/80 (Item No. 22173).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shawi, A.A., Rasul, A., Khan, M., et alEupatilin: A flavonoid compound isolated from the artemisia plant, induces apoptosis and G2/M phase cell cycle arrest in human melanoma A375 cells. Afr. J. Pharm. Pharmacol. 5(5), 582-588 (2011).

    2. Choi, Y., Jung, Y., and Kim, S.N. Identification of eupatilin from Artemisia argyi as a selective PPARα agonist using affinity selection ultrafiltration LC-MS. Molecules 20(8), 13753-13763 (2015).

    3. Koshihara, Y., Neichi, T., Murota, S.i., et alSelective inhibition of 5-lipoxygenase by natural compounds isolated from Chinese plants, Artemisia rubripes Nakai. FEBS Lett. 158(1), 41-44 (1983).

    4. Liu, H., Hao, J., Wu, C., et alEupatilin alleviates lipopolysaccharide-induced acute lung injury by inhibiting inflammation and oxidative stress. Med. Sci Monit. 25, 8289-8296 (2019).

    5. Song, E.-H., Chung, K.-S., Kang, Y.-M., et alEupatilin suppresses the allergic inflammatory response in vitro and in vivo. Phytomedicine 42, 1-8 (2018).

    6. Choi, E.J., Oh, H.M., Na, B.R., et alEupatilin protects gastric epithelial cells from oxidative damage and down-regulates genes responsible for the cellular oxidative stress. Pharmacol. Res. 25(6), 1355-1364 (2008).