470-17-7 Usage
Description
Isoalantolactone, a sesquiterpene lactone belonging to the eudesmanolide group, is a compound isolated from Inula helenium, which is a plant known for its medicinal properties. It possesses potent anti-inflammatory properties and has been found to be a complete inhibitor of NFkB at concentrations as low as 5 μM, acting through the inhibition of IKK. Isoalantolactone has demonstrated protective effects in endotoxic shock in rodent models and has the ability to induce apoptosis in glioma cells.
Uses
Used in Cancer Treatment:
Isoalantolactone is used as an anticancer agent for its ability to inhibit tumor cell growth and induce apoptosis. It is particularly effective in the treatment of various types of cancer due to its potent anti-inflammatory and cell growth inhibition properties.
Used in Anti-Inflammatory Applications:
Isoalantolactone is used as an anti-inflammatory agent for its ability to suppress the expression of IL-8, iNOS, and RANTES biosynthesis. Its complete inhibition of NFkB at 5 μM makes it a promising candidate for treating inflammation-related conditions.
Used in Pharmaceutical Research:
Isoalantolactone is used as a research compound in the development of new drugs and therapies, particularly in the fields of cancer treatment and anti-inflammatory medications. Its unique properties and mechanisms of action provide valuable insights for pharmaceutical researchers working on novel drug delivery systems and treatment strategies.
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
Check Digit Verification of cas no
The CAS Registry Mumber 470-17-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 0 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 470-17:
(5*4)+(4*7)+(3*0)+(2*1)+(1*7)=57
57 % 10 = 7
So 470-17-7 is a valid CAS Registry Number.
InChI:InChI=1/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
470-17-7Relevant articles and documents
Synthesis of (+)-Isoalantolactone and (+)-Isoalloalantolactone from (-)-Santonin
Blay, Gonzalo,Cardona, Luz,Garcia, Begona,Pedro, Jose R.,Serrano, Angel
, p. 5265 - 5272 (2007/10/02)
This paper reports on the chemical conversion of (-)-santonin into (+)-isoalantolactone and (+)-isoalloalantolactone involving functionality transfer from C6 to C8, refunctionalization of the ring A and the formation of the α-methylene-8β,12-olide moiety.
An Annelation Approach to the Synthesis of Eudesmane and Elemane Sesquiterpene Lactones. Total Synthesis of dl-Dihydrocallitrisin, dl-7,8-Epialantolactone, dl-7,8-Epiisoalantolactone, and dl-Atractylon
Schultz, Arthur G.,Godfrey, Jollie D.
, p. 2414 - 2428 (2007/10/02)
An annelation approach to the synthesis of eudesmane sesquiterpenes is described.The 1,6-annelation reagent α-carbomethoxy-β-methyl-γ-methylidene-Δα,β-butenolide (1) is used to construct the linear tricyclic lactone 2,5,6,7,8,8a,9,9aβ-octahydro-8aβ-methyl-2-oxonaphthofuran-3-carboxylic acid methyl ester (2).The conversion of 2 to dl-dihydrocallitrisin (3), dl-7,8-epialantolactone (4), dl-7,8-epiisoalantolactone (5), and dl-atractylon (6) is detailed.Studies directed toward synthesis of the elemane sesquiterpene lactones vernomenin and vernolepin also are presented.
