| Identification | More | [Name]
Isoalantolactone | [CAS]
470-17-7 | [Synonyms]
(3ar,4as,8ar,9ar)-8a-methyl-3,5-dimethylene-decahydro-naphtho[2,3-b]furan-2-one
ISOALANTOACTONE
ISOALANTOLACTONE
ISOHELENIN
11(13)-dien-12-oicacid,8-beta-hydroxy-eudesma-4(14gamma-lactone
methyl-3,5-bis(methylene)-,(3aR,4aS,8aR,9aR)-
Naphtho[2,3-b]furan-2(3H)-one,decahydro-8a-
(3aR)-3aα,4,4aα,5,6,7,8,8a,9,9aα-Decahydro-3,5-bismethylene-8aβ-methylnaphtho[2,3-b]furan-2(3H)-one
(3aR,4aα,9aα)-3a,4,4a,5,6,7,8,8a,9,9a-Decahydro-8aβ-methyl-3,5-bis(methylene)naphtho[2,3-b]furan-2(3H)-one | [Molecular Formula]
C15H20O2 | [MDL Number]
MFCD00056777 | [Molecular Weight]
232.32 | [MOL File]
470-17-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
115℃ | [Boiling point ]
364.9±42.0 °C(Predicted) | [density ]
1.07±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Soluble in DMSO (up to 50 mg/ml) or ethanol (30 mg/ml) | [form ]
solid | [color ]
White | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. | [InChI]
InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15-/m1/s1 | [InChIKey]
CVUANYCQTOGILD-QVHKTLOISA-N | [SMILES]
O1C(=O)C(=C)[C@@]2([H])C[C@]3([H])[C@@](C)(C[C@@]12[H])CCCC3=C | [LogP]
3.420 | [CAS DataBase Reference]
470-17-7(CAS DataBase Reference) | [NIST Chemistry Reference]
Naphtho(2,3-b)furan-2(3h)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3ar-(3a«alpha»,4a«alpha»,8a«beta»,9a«alpha»))-(470-17-7) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S22:Do not breathe dust .
S36:Wear suitable protective clothing . | [HS Code ]
29322090 |
| Hazard Information | Back Directory | [Description]
Isohelenin (470-17-7) is a sesquiterpene lactone isolated from Mexican Indian medicinal plants known to have anti-inflammatory properties. A potent inhibitor of NFkB (complete inhibition at 5 μM)1 acting via inhibition of IKK?6. Isohelenin-mediated NFkB inhibition suppresses IL-8 expression2, iNOS expression3 and RANTES biosynthesis4. Displays protective effects in endotoxic shock in rodent models.5 Induces apoptosis in glioma cells.6 | [Uses]
Isoalantolactone is a sesquiterpene lactone used in the treatment of cancer. It can inhibit tumor cell growth and induce apoptosis. | [Definition]
ChEBI: A sesquiterpene lactone of the eudesmanolide group. It has been isolated from Inula helenium. | [References]
Bork et al. (1997), Sesquiterpene lactone containing Mexican Indian medicinal plants and pure sesquiterpene lactones as potent inhibitors of transcription factor NK-kappaB; FEBS Lett., 402 85
Mazor et al. (2000), Sesquiterpene lactones are potent inhibitors of interleukin 8 gene expression in cultured human respiratory epithelium; Cytokine, 12 239
Wong and Menendez (1999), Sesquiterpene lactones inhibit inducible nitric oxide synthase gene expression in cultured rat aortic smooth muscle cells; Biochem. Biophys. Res. Commun., 262 375
Li et al. (2001), Induction of RANTES chemokine expression in human astrocytic cells is dependent upon activation of NK-kappaB transcription factor; Int. J. Mol. Med., 7 527
Sheehan et al. (2002), Protective effects of isohelenin, an inhibitor of nuclear factor KappaB in endotoxic shock in rats; Endotoxin Res, 8 99
Xing et al. (2019), Isoalantolactone inhibits IKK? kinase activity to interrupt the NF-kB/COX-2-mediated signaling cascade and induces apoptosis regulated by the mitochondrial translocation of cofilin in glioblastoma; Cancer Med., 8 1655 |
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