Andrographolide

CAS: 5508-58-7

Ref. TR-A637475

Product Information

• Name: Andrographolide
• Synonyms: 2(3H)-Furanone, 3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, (3E,4S)-, 2(3H)-Furanone, 3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, [1R-[1a[E(S*)],4aß,5a,6a,8aa]]-, 5ß,9ßH,10a-Labda-8(20),12-dien-16-oic acid, 3a,14,15,18-tetrahydroxy-, ?-lactone (7CI), Andrographis (6CI), (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone, Andrographiside aglycon, Andrographolid, (2R,5S,10R,12E,14S)-2,14,17-trihydroxy-20-oxo-9,19-didehydro-5,6,7,8,9,10,11,14,15-decahydro-20:5,10-dicycloretinal, (2R,5S,6S,10R,12E,14S)-2,14,17-trihydroxy-20-oxo-9,19-didehydro-5,6,7,8,9,10,11,14,15-decahydro-20:5,10-dicycloretinal, (5S,10R,12E)-2,14,16-trihydroxy-20-oxo-9,19-didehydro-5,6,7,8,9,10,11,14,15-decahydro-20:5,10-dicycloretinal, 2(3H)-Furanone, 3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-, (1R-(1-alpha(E(S*)),4a-beta,5-alpha,6-alpha,8a-alpha))-, 2(3H)-Furanone, 3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, (3E,4S)-, 2(3H)-Furanone, 3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, [1R-[1α[E(S*)],4aβ,5α,6α,8aα]]-, 3-(2-(Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl)ethylidene)dihydro-4-hydroxyfuran-2(3H)-one, 3-Dehydroandrographolide Or 19-Dehydroandrographolide? P. 1388, 3-[2-[Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylennaphthyl]ethyliden]dihydro-4-hydroxyfuran-2(3H)-on, 3-[2-[decahidro-6-hidroxi-5-(hidroximetil)-5,8a-dimetil-2-metilennaftil]etiliden]dihidro-4-hidroxifuran-2(3H)-ona, 3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphtyl]ethylidene]dihydro-4-hydroxyfuranne-2(3H)-one, 4-hydroxy-3-{2-[6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethylidene}dihydrofuran-2(3H)-one, 5β,9β<span class="text-smallcaps">H</span>,10α-Labda-8(20),12-dien-16-oic acid, 3α,14,15,18-tetrahydroxy-, γ-lactone, 5β,9βH,10α-Labda-8(20),12-dien-16-oic acid, 3α,14,15,18-tetrahydroxy-, γ-lactone, Andrographis, Andrographolide,14-Deoxy 11,12-Didehydro, Nsc 383468, Unii-410105Jhgr
• CAS: 5508-58-7

Description

Applications Andrographolide is a labdane diterpenoid (2). Andrographolide is the main bioactive component isolated from the medicinal plant Andrographis paniculata (2). Andrographolide showed significant antihepatotoxic action in P. berghei K173-induced hepatic damage in M. natalensis(1). Andrographolide inhibits tumor necrosis factor-α (TNF-α)-induced intercellular adhesion mol.-1 (ICAM-1) expression and adhesion of HL-60 cells onto human umbilical vein endothelial cells (HUVEC), which are associated with inflammatory diseases (2). These findings suggest that Andrographolide may have potential as a cardiovascular-protective agent.
References (1) Chander, R. et al.: Int. J. Pharmacog. (1995) 33, 135-8 (2) Chen, H.-W. et al.: J. Nat. Prod. (2011) 74, 2408-13

• Brand: TRC

Chemical properties

• Molecular weight: 350.45
• Formula: C₂₀H₃₀O₅
• Color/Form: Neat
• InChI: 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: InChIKey=BOJKULTULYSRAS-ACAGNQJTSA-N
• SMILES: C=C1CCC2C(C)(CO)C(O)CCC2(C)C1CC=C1C(=O)OCC1O