A flavonoid with diverse biological activities
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Eupatorin

Item No. 29599

Technical Information
Formal Name
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-1-benzopyran-4-one
CAS Number
855-96-9
Synonyms
  • NSC 106402
Molecular Formula
C18H16O7
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:9): 0.1 mg/ml
λmax
216, 242, 276, 343 nm
SMILES
O=C1C2=C(O)C(OC)=C(OC)C=C2OC(C3=CC(O)=C(OC)C=C3)=C1
InChi Code
InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3
InChi Key
KLAOKWJLUQKWIF-UHFFFAOYSA-N
Origin
Plant/Orthosiphon aristatus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Eupatorin is a flavonoid that has been found in L. camara and has diverse biological activities.1,2,3,4 It inhibits the growth of HeLa, MK-1, and B16/F10 tumor cells (GI50s = 15, 58, and 44 µM, respectively).1 Eupatorin is active against T. cruzi epimastigotes and trypomastigotes (IC50s = 0.2 and 61.8 µg/ml, respectively) without inducing cytotoxicity in Vero cells (IC50 = >500 µg/ml).2 It induces vasorelaxation in isolated rat thoracic aortic rings precontracted with phenylephrine (pD2 = 6.66).3 Eupatorin (10 and 100 µM) reduces nuclear translocation of NF-κB and STAT1α in J774 murine macrophages and reduces paw edema in a mouse model of carrageenan-induced paw inflammation when administered at a dose of 50 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nagao, T., Abe, F., Kinjo, J., et alAntiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship. Biol. Pharm. Bull. 25(7), 875-879 (2002).

    2. Beer, M.F., Frank, F.M., Germán Elso, O., et alTrypanocidal and leishmanicidal activities of flavonoids isolated from Stevia satureiifolia var. satureiifolia. Pharm. Biol. 54(10), 2188-2195 (2016).

    3. Yam, M.F., Tan, C.S., Ahmad, M., et alMechanism of vasorelaxation induced by eupatorin in the rats aortic ring. Eur. J. Pharmacol. 789, 27-36 (2016).

    4. Laavola, M., Nieminen, R., Yam, M.F., et alFlavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation. Planta Med. 78(8), 779-786 (2012).