A coumarin glucoside with diverse biological activity
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Nodakenin

Item No. 25213

Technical Information
Formal Name
(2R)-2-[1-(β-D-glucopyranosyloxy)-1-methylethyl]-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one
CAS Number
495-31-8
Molecular Formula
C20H24O9
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 5 mg/mlDMSO: 50 mg/ml
λmax
224, 336 nm
SMILES
O=C1C=CC2=C(C=C(O[C@@H](C(C)(C)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C4)C4=C2)O1
InChi Code
InChI=1S/C20H24O9/c1-20(2,29-19-18(25)17(24)16(23)13(8-21)28-19)14-6-10-5-9-3-4-15(22)27-11(9)7-12(10)26-14/h3-5,7,13-14,16-19,21,23-25H,6,8H2,1-2H3/t13-,14-,16-,17+,18-,19+/m1/s1
InChi Key
HXCGUCZXPFBNRD-DNLMCPORSA-N
Origin
Plant/Notopterygium incisum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Nodakenin is a coumarin glucoside originally isolated from P. decursivum that has anti-inflammatory, neuroprotective, and neurogenic activities.1,2,3,4,5 It dose-dependently reduces LPS-induced increases in TNF-α, IL-6, and IL-1β mRNA expression and protein levels and NK-κB activity and translocation in RAW 264.7 macrophages when used at concentrations ranging from 25 to 100 µM.2 Nodakenin (5, 10, and 20 mg/kg) prevents airway inflammation, hyper-responsiveness, and remodeling in a mouse model of chronic asthma induced by ovalbumin.3 It also decreases the levels of IL-4, IL-5, IL-13, as well as matrix metalloproteinase-2 (MMP-2) and MMP-9 in bronchoalveolar lavage fluid (BALF). Nodakenin increases proliferation of neural progenitor cells in the adult mouse hippocampal dentate gyrus, increases hippocampal protein levels of AKT and glycogen synthase kinase-3β (GSK-3β), and improves learning and memory in the passive avoidance test.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Junzo, A. The constitution of nodakenin, a new glucoside from Peucedanum decursivum Maxim. Bull. Chem. Soc. Jpn. 4(1), 16-20 (1929).

    2. Rim, H.K., Cho, W., Sung, S.H., et alNodakenin suppresses lipopolysaccharide-induced inflammatory responses in macrophage cells by inhibiting tumor necrosis factor receptor-associated factor 6 and nuclear factor-κB pathways and protects mice from lethal endotoxin shock. J. Pharmacol. Exp. Ther. 342(3), 654-664 (2012).

    3. Xiong, Y., Wang, J., Yu, H., et alThe effects of nodakenin on airway inflammation, hyper-responsiveness and remodeling in a murine model of allergic asthma. Immunopharmacol. Immunotoxicol. 36(5), 341-348 (2014).

    4. Kang, S.Y., and Kim, Y.C. Neuroprotective coumarins from the root of Angelica gigas: Structure-activity relationships. Arch. Pharm. Res. 30(11), 1368-1373 (2007).

    5. Gao, Q., Jeon, S.J., Jung, H.A., et alNodakenin enhances cognitive function and adult hippocampal neurogenesis in mice. Neurochem. Res. 40(7), 1438-1447 (2015).