855-96-9
Chemical Structure
Eupatorin
- CAS No.: 855-96-9
- Formula:C18H16O7
- Molecular Weight:344.32
IUPAC Name: 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one
InChIKey: KLAOKWJLUQKWIF-UHFFFAOYSA-N
SMILES: O=C1C=C(C2=CC=C(OC)C(O)=C2)OC3=CC(OC)=C(OC)C(O)=C13
Biological Activity: Eupatorin is an orally active flavonoid with antiproliferative and vasodilatory properties. Eupatorin downregulates the expression levels of NF-κB, MMP9, IL-1β and TNF-α. Eupatorin induces apoptosis, G2/M phase cell cycle arrest, and reactive oxygen species (ROS) production. Eupatorin modulates the activities of muscarinic receptors and β-adrenergic receptors; inhibits sarcoplasmic reticulum calcium release and calcium channels; and activates the NO/sGC/cGMP pathway, indomethacin-sensitive pathway, and potassium channel pathway. Eupatorin exerts cytotoxic effects on cancer cell lines, and is metabolized by CYP1A1 and CYP1 family enzymes to form metabolites with antiproliferative activity. Eupatorin can be used in research related to breast cancer, hypertension, and leukemia[1][2][3][4].
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Eupatorin | 99.53% | Eupatorin is an orally active flavonoid with antiproliferative and vasodilatory properties. Eupatorin downregulates the expression levels of NF-κB, MMP9, IL-1β and TNF-α. Eupatorin induces apoptosis, G2/M phase cell cycle arrest, and reactive oxygen species (ROS) production. Eupatorin modulates the activities of muscarinic receptors and β-adrenergic receptors; inhibits sarcoplasmic reticulum calcium release and calcium channels; and activates the NO/sGC/cGMP pathway, indomethacin-sensitive pathway, and potassium channel pathway. Eupatorin exerts cytotoxic effects on cancer cell lines, and is metabolized by CYP1A1 and CYP1 family enzymes to form metabolites with antiproliferative activity. Eupatorin can be used in research related to breast cancer, hypertension, and leukemia. | ||||||||||||||||||||
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Eupatorin (Standard) | ≥98% | Eupatorin (Standard) is the analytical standard of Eupatorin. This product is intended for research and analytical applications. Eupatorin, a naturally occurring flavone, arrests cells at the G2-M phase of the cell cycle and induces apoptotic cell death involving activation of multiple caspases, mitochondrial release of cytochrome c and poly(ADP-ribose) polymerase cleavage. | ||||||||||||||||||||
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- [1]. Abd Razak N, et al. Eupatorin Suppressed Tumor Progression and Enhanced Immunity in a 4T1 Murine Breast Cancer Model. Integr Cancer Ther. 2020 Jan-Dec;19:1534735420935625. [Content Brief]
- [2]. Mun Fei Yam, et al. Mechanism of vasorelaxation induced by eupatorin in the rats aortic ring. European Journal of Pharmacology. Volume 789, 15 October 2016, Pages 27-36.
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[3]. Androutsopoulos V, et al. Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism. Breast Cancer Res. 2008;10(3):R39.
- [4]. Estévez S, et al. Eupatorin-induced cell death in human leukemia cells is dependent on caspases and activates the mitogen-activated protein kinase pathway. PLoS One. 2014;9(11):e112536. Published 2014 Nov 12. [Content Brief]
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