A coumarin with diverse biological activities
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Columbianadin

Item No. 27661

Technical Information
Formal Name
(2Z)-2-methyl-2-butenoic acid, 1-[(8S)-8,9-dihydro-2-oxo-2H-furo[2,3-h]-1-benzopyran-8-yl]-1-methylethyl ester
CAS Number
5058-13-9
Synonyms
  • Columbianetin
Molecular Formula
C19H20O5
Formula Weight
Purity
≥98%
A solid
DMF: 25mg/mLDMF:PBS (pH 7.2) (1:4): 0.2mg/mLDMSO: 20mg/mLEthanol: 2mg/mL
λmax
325 nm
SMILES
O=C1C=CC2=C(C(C[C@@H](C(OC(/C(C)=C\C)=O)(C)C)O3)=C3C=C2)O1
InChi Code
InChI=1S/C19H20O5/c1-5-11(2)18(21)24-19(3,4)15-10-13-14(22-15)8-6-12-7-9-16(20)23-17(12)13/h5-9,15H,10H2,1-4H3/b11-5-/t15-/m0/s1
InChi Key
JRIBPWOXWIRQOQ-GHAIFCDISA-N
Origin
Plant/Angelicae pubescentis radix
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Columbianadin is a coumarin that has been found in A. pubescens and has diverse biological activities.1,2,3,4 It inhibits depolarization-induced calcium uptake in GH3 rat pituitary cells.1 Columbianadin inhibits HIV-1 replication in H9 cells (EC50 = 4.6 µM).2 It inhibits IL-1β-induced production of IL-6 in A549 cells and reduces inducible nitric oxide synthase (iNOS) levels and LPS-induced NO production in MH-S cells.3 Columbianadin (20-60 mg/kg) decreases the number of alveolar and interstitial macrophages and alveolar wall thickness in a mouse model of LPS-induced lung inflammation. It also reduces formalin-induced paw licking in mice when administered at a dose of 10 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Törnquist, K., and Vuorela, H. The furanocoumarin columbianadin inhibits depolarization induced Ca2+ uptake in rat pituitary GH3 cells. Planta Med. 56(1), 127-129 (1990).

    2. Lee, T.T.-Y., Kashiwada, Y., Huang, L., et al. Suksdorfin: An anti-HIV principle from Lomatium suksdorfii, its structure-activity correlation with related coumarins, and synergistic effects with anti-AIDS nucleosides. Bioorg. Med. Chem. 2(10), 1051-1056 (1994).

    3. Lim, H.J., Lee, J.H., Choi, J.S., et al. Inhibition of airway inflammation by the roots of Angelica decursiva and its constituent, columbianadin. J. Ethnopharmacol. 155(2), 1353-1361 (2014).

    4. Chen, Y.-F., Tsai, H.-Y., and Wu, T.-S. Anti-inflammatory and analgesic activities from roots of Angelica pubescens. Planta Med. 61(1), 2-8 (1995).