Andrographolide

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. Andrographolide treatment inhibits nuclear factor kappa B (NF-kappaB) binding to DNA promoters of target genes (IC50 = ~15 µM), by forming a covalent adduct with reduced cysteine (62) of the NF-kappaB p50 subunit, and can also induce expression of the CYP1A subfamily of the cytochrome P450 family of enzymes. At 5 µg/g body weight it can suppress the activation of NF-kappaB 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.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: 350.5. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 10 mg/ml, DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml, DMSO: 2 mg/ml, Ethanol: 0.2 mg/ml. lambdamax: 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.