470-17-7 Usage
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
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.
