| 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. | [in vivo]
The acute and chronic toxic effects of Isoalantolactone in CD1 mice are assessed by measuring the changes in body weight, blood biochemistry and histopathology of liver and kidneys in comparison with control groups. Isoalantolactone is well tolerated by mice and no mortality or any sign of pharmacotoxicity are found at a dose of 100 mg/kg during both experimental periods (7 & 30 days). Body weight gains and food consumption are comparable for control and treated mice during both experimental periods and there were no drug-related changes in histopathological and blood biochemistry parameters. The histopathological changes in liver and kidneys are assessed using hematoxylin and eosin staining and correlated with liver and renal function biomarkers. No obvious morphological changes are observed in liver and kidney structures of control and treatment groups. There is a slight increase in serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) level of treatment group at dose day 7 but this increase is not significantly different (P<0.05) from control group. A significant increase in total bilirubin (TBIL) concentration is found in treatment group (1.43±0.26 vs 0.76±0.12 in control, P<0.05) at dose day 7. Similarly the changes in renal function biomarkers are not significantly different (P<0.05) in the serum of control and treatment groups at dose day 7. The concentration of creatinine (Cr) slightly increases whereas concentration of blood urea nitrogen (BUN) slightly decreases in treatment group. The serum level of AST, ALT, TBIL and BUN slightly decreases when mice are injected with Isoalantolactone at a dose of 100 mg/kg for 30 days[2]. | [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 |
|
|