A coumarin with diverse biological activities and an active metabolite of scoparone
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Isoscopoletin

Item No. 34117

Technical Information
Formal Name
6-hydroxy-7-methoxy-2H-1-benzopyran-2-one
CAS Number
776-86-3
Synonyms
  • Esculetin 7-methyl ether
  • 7-methoxy-6-Hydroxycoumarin
  • 7-Methoxyesculetin
Molecular Formula
C10H8O4
Formula Weight
Purity
≥98%
A solid
Chloroform: 1 mg/ml
λmax
231 nm
SMILES
O=C1OC2=C(C=C1)C=C(O)C(OC)=C2
InChi Code
InChI=1S/C10H8O4/c1-13-9-5-8-6(4-7(9)11)2-3-10(12)14-8/h2-5,11H,1H3
InChi Key
SYTYLPHCLSSCOJ-UHFFFAOYSA-N
Origin
Plant/Erigeron breviscapus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Isoscopoletin is a coumarin that has been found in D. fragrans and has diverse biological activities and is an active metabolite of scoparone (Item No. 20046).1,2,3,4,5 It is formed from scoparone by the cytochrome P450 (CYP) isoform Cyp2c29 in mouse liver microsomes.5 Isoscopoletin is cytotoxic to A549 lung, MCF-7 breast, and HepG2 liver cancer cells (IC50s = 5.25, 8.58, and 4.76 µM, respectively).1 It is active against Gram-positive and Gram-negative bacteria, including S. aureus and E. coli, respectively, in agar diffusion assays.2 Isoscopoletin inhibits 15-lipoxygenase (15-LO; IC50 = 15.1 µM) and reduces paw thickness in a rat model of carrageenan-induced paw edema when administered at a dose of 0.1 mg/kg.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhao, D.-D., Zhao, Q.-S., Liu, L., et alCompounds from Dryopteris fragrans (L.) Schott with cytotoxic activity. Molecules 19(3), 3345-3355 (2014).

    2. Nazir, S., Li, B., Tahir, K., et alAntimicrobial activity of five constituents isolated from Ranunculus muricatus. J. Med. Plants Res. 7(47), 3438-3443 (2013).

    3. Deng, S., Palu, A.K., West, B.J., et alLipoxygenase inhibitory constituents of the fruits of noni (Morinda citrifolia) collected in Tahiti. J. Nat. Prod. 70(5), 859-862 (2007).

    4. Selim, Y.A., and Ouf, N.H. Anti-inflammatory new coumarin from the Ammi majus L. Org. Med. Chem. Lett. 2(1), 1 (2012).

    5. Meyer, R.P., Hagemeyer, C.E., Knoth, R., et alOxidative hydrolysis of scoparone by cytochrome P450 CYP2C29 reveals a novel metabolite. Biochem. Biophys. Res. Commun. 285(1), 32-39 (2001).