An inhibitor of NF-κB signaling
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Andrographolide

Item No. 11679

Technical Information
Formal Name
3E-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4S-hydroxy-2(3H)-furanone
CAS Number
5508-58-7
Molecular Formula
C20H30O5
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 10 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 2 mg/mlEthanol: 0.2 mg/ml
λmax
225 nm
SMILES
C=C1CC[C@]2([H])[C@@](CO)(C)[C@H](O)CC[C@@]2(C)[C@@H]1/C=C/C3C(OC[C@H]3O)=O
InChi Code
InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1
InChi Key
BOJKULTULYSRAS-OTESTREVSA-N
Origin
Plant/Andrographis paniculata
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Andrographolide is a labdane diterpenoid that is the main bioactive component of A. paniculata, a well-recognized medicinal plant in Asia. It exerts a wide range of therapeutic actions, including immunosuppressant, antithrombotic, anti-inflammatory, antineoplastic, antiviral, antibacterial, antidiabetic, antioxidative stress, antipyretic, antioedematogenic, and antinociceptive activities.1 Andrographolide treatment inhibits nuclear factor kappa B (NF-κB) binding to DNA promoters of target genes (IC50 = ~15 μM), by forming a covalent adduct with reduced cysteine (62) of the NF-κB p50 subunit, and can also induce expression of the CYP1A subfamily of the cytochrome P450 family of enzymes.2,3 At 5 μg/g body weight it can suppress the activation of NF-κB in stimulated endothelial cells, reducing the expression of the cell adhesion molecule E-selectin, abrogating the cytokine- and endotoxin-induced peritoneal infiltration of neutrophils, attenuating septic shock, and preventing allergic lung inflammation in a mouse model of asthma.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jarukamjorn, K., and Nemoto, N. Pharmacological aspects of Andrographis paniculata on health and its major diterpenoid constituent andrographolide. J. Health Sci. 54(4), 370-381 (2008).

    2. Varma, A., Padh, H., and Shrivastava, N. Andrographolide: A new plant-derived antineoplastic entity on horizon. Evid. Based Complement. Alternat. Med. 2011, 1-9 (2011).

    3. Xia, Y.F., Ye, B.Q., Li, Y.D., et alAndrographolide attenuates inflammation by inhibition of NF-κB activation through covalent modification of reduced cysteine 62 of p50. J. Immunol. 173(6), 4207-4217 (2004).