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MedKoo Cat#: 584459 | Name: Alantolactone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Alantolactone selectively suppresses STAT3 activation and exhibits potent anticancer activity in MDA-MB-231 cells. Alantolactone suppresses inflammation, apoptosis and oxidative stress in cigarette smoke-induced human bronchial epithelial cells through activation of Nrf2/HO-1 and inhibition of the NF-κB pathways. Results suggest that this compound exerts its anticancer effects by providing free radicals and inhibiting some of the signaling pathways that are effective in progression of cancer cells.

Chemical Structure

Alantolactone
CAS#546-43-0

Theoretical Analysis

MedKoo Cat#: 584459

Name: Alantolactone

CAS#: 546-43-0

Chemical Formula: C15H20O2

Exact Mass: 232.1463

Molecular Weight: 232.32

Elemental Analysis: C, 77.55; H, 8.68; O, 13.77

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 weeks
250mg USD 650.00 2 Weeks
500mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Alantolactone; AI3-31147; AI331147; AI3 31147
IUPAC/Chemical Name
(3AR-(3aalpha,5beta,8abeta,9aalpha))-3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylenenaphtho(2,3-b)furan-2(3H)-one
InChi Key
PXOYOCNNSUAQNS-AGNJHWRGSA-N
InChi Code
InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1
SMILES Code
O=C(O[C@@]1([H])[C@]2([H])C=C3[C@@H](C)CCC[C@]3(C)C1)C2=C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 232.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Alzoubi K, Calabrò S, Egler J, Faggio C, Lang F. Triggering of programmed erythrocyte death by alantolactone. Toxins (Basel). 2014 Dec 22;6(12):3596-612. doi: 10.3390/toxins6123596. PubMed PMID: 25533522; PubMed Central PMCID: PMC4280550. 2: Yang C, Yang J, Sun M, Yan J, Meng X, Ma T. Alantolactone inhibits growth of K562/adriamycin cells by downregulating Bcr/Abl and P-glycoprotein expression. IUBMB Life. 2013 May;65(5):435-44. doi: 10.1002/iub.1141. Epub 2013 Feb 26. PubMed PMID: 23441067. 3: Yao Y, Xia D, Bian Y, Sun Y, Zhu F, Pan B, Niu M, Zhao K, Wu Q, Qiao J, Fu C, Li Z, Xu K. Alantolactone induces G1 phase arrest and apoptosis of multiple myeloma cells and overcomes bortezomib resistance. Apoptosis. 2015 Aug;20(8):1122-33. doi: 10.1007/s10495-015-1140-2. PubMed PMID: 26033479. 4: Yao Y, Sun YY, Xia DD, Niu MS, Zhao K, Li ZY, Zeng LY, Xu KL. [Effect of Alantolactone on Proliferation of RPMI-8226 Cells and Its Possible Mechnism]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2015 Oct;23(5):1336-40. doi: 10.7534/j.issn.1009-2137.2015.05.021. Chinese. PubMed PMID: 26524033. 5: Yang C, Cai H, Yan J, Yang J, Sun M, Meng X, Ma T. [Inhibitory effect of alantolactone on the proliferation of K562/ADR cells and its mechanism]. Zhonghua Xue Ye Xue Za Zhi. 2014 Jun;35(6):515-8. doi: 10.3760/cma.j.issn.0253-2727.2014.06.009. Chinese. PubMed PMID: 24985175. 6: Wang J, Zhao YM, Zhang ML, Shi QW. Simultaneous determination of chlorogenic acid, caffeic acid, alantolactone and isoalantolactone in Inula helenium by HPLC. J Chromatogr Sci. 2015 Apr;53(4):526-30. doi: 10.1093/chromsci/bmu079. Epub 2014 Jul 4. PubMed PMID: 24996657. 7: Chun J, Li RJ, Cheng MS, Kim YS. Alantolactone selectively suppresses STAT3 activation and exhibits potent anticancer activity in MDA-MB-231 cells. Cancer Lett. 2015 Feb 1;357(1):393-403. doi: 10.1016/j.canlet.2014.11.049. Epub 2014 Nov 27. PubMed PMID: 25434800. 8: Khan M, Li T, Ahmad Khan MK, Rasul A, Nawaz F, Sun M, Zheng Y, Ma T. Alantolactone induces apoptosis in HepG2 cells through GSH depletion, inhibition of STAT3 activation, and mitochondrial dysfunction. Biomed Res Int. 2013;2013:719858. doi: 10.1155/2013/719858. Epub 2012 Dec 27. PubMed PMID: 23533997; PubMed Central PMCID: PMC3591150. 9: Khan M, Yi F, Rasul A, Li T, Wang N, Gao H, Gao R, Ma T. Alantolactone induces apoptosis in glioblastoma cells via GSH depletion, ROS generation, and mitochondrial dysfunction. IUBMB Life. 2012 Sep;64(9):783-94. doi: 10.1002/iub.1068. Epub 2012 Jul 27. PubMed PMID: 22837216. 10: Rasul A, Khan M, Ali M, Li J, Li X. Targeting apoptosis pathways in cancer with alantolactone and isoalantolactone. ScientificWorldJournal. 2013 Oct 27;2013:248532. doi: 10.1155/2013/248532. eCollection 2013. Review. PubMed PMID: 24288468; PubMed Central PMCID: PMC3826378. 11: Lei JC, Yu JQ, Yin Y, Liu YW, Zou GL. Alantolactone induces activation of apoptosis in human hepatoma cells. Food Chem Toxicol. 2012 Sep;50(9):3313-9. doi: 10.1016/j.fct.2012.06.014. Epub 2012 Jun 18. PubMed PMID: 22721982. 12: Zhang Y, Bao YL, Wu Y, Yu CL, Huang YX, Sun Y, Zheng LH, Li YX. Alantolactone induces apoptosis in RKO cells through the generation of reactive oxygen species and the mitochondrial pathway. Mol Med Rep. 2013 Oct;8(4):967-72. doi: 10.3892/mmr.2013.1640. Epub 2013 Aug 16. PubMed PMID: 23970102. 13: Zhao P, Pan Z, Luo Y, Zhang L, Li X, Zhang G, Zhang Y, Cui R, Sun M, Zhang X. Alantolactone Induces Apoptosis and Cell Cycle Arrest on Lung Squamous Cancer SK-MES-1 Cells. J Biochem Mol Toxicol. 2015 May;29(5):199-206. doi: 10.1002/jbt.21685. Epub 2015 Jan 19. PubMed PMID: 25597476. 14: Rezeng C, Yuan D, Long J, Suonan D, Yang F, Li W, Tong L, Jiumei P. Alantolactone exhibited anti-herpes simplex virus 1 (HSV-1) action in vitro. Biosci Trends. 2015 Dec;9(6):420-2. doi: 10.5582/bst.2015.01171. PubMed PMID: 26781801. 15: Xu R, Zhou G, Peng Y, Wang M, Li X. Pharmacokinetics, tissue distribution and excretion of isoalantolactone and alantolactone in rats after oral administration of Radix Inulae extract. Molecules. 2015 Apr 28;20(5):7719-36. doi: 10.3390/molecules20057719. PubMed PMID: 25927901. 16: Chun J, Choi RJ, Khan S, Lee DS, Kim YC, Nam YJ, Lee DU, Kim YS. Alantolactone suppresses inducible nitric oxide synthase and cyclooxygenase-2 expression by down-regulating NF-κB, MAPK and AP-1 via the MyD88 signaling pathway in LPS-activated RAW 264.7 cells. Int Immunopharmacol. 2012 Dec;14(4):375-83. doi: 10.1016/j.intimp.2012.08.011. Epub 2012 Aug 28. PubMed PMID: 22940184. 17: Wei W, Huang H, Zhao S, Liu W, Liu CX, Chen L, Li JM, Wu YL, Yan H. Alantolactone induces apoptosis in chronic myelogenous leukemia sensitive or resistant to imatinib through NF-κB inhibition and Bcr/Abl protein deletion. Apoptosis. 2013 Sep;18(9):1060-70. doi: 10.1007/s10495-013-0854-2. PubMed PMID: 23613107. 18: Mi XG, Song ZB, Wu P, Zhang YW, Sun LG, Bao YL, Zhang Y, Zheng LH, Sun Y, Yu CL, Wu Y, Wang GN, Li YX. Alantolactone induces cell apoptosis partially through down-regulation of testes-specific protease 50 expression. Toxicol Lett. 2014 Jan 30;224(3):349-55. doi: 10.1016/j.toxlet.2013.11.002. Epub 2013 Nov 16. PubMed PMID: 24252419. 19: Lim HS, Jin SE, Kim OS, Shin HK, Jeong SJ. Alantolactone from Saussurea lappa Exerts Antiinflammatory Effects by Inhibiting Chemokine Production and STAT1 Phosphorylation in TNF-α and IFN-γ-induced in HaCaT cells. Phytother Res. 2015 Jul;29(7):1088-96. doi: 10.1002/ptr.5354. Epub 2015 Apr 17. PubMed PMID: 25881570. 20: Ding Y, Gao H, Zhang Y, Li Y, Vasdev N, Gao Y, Chen Y, Zhang Q. Alantolactone selectively ablates acute myeloid leukemia stem and progenitor cells. J Hematol Oncol. 2016 Sep 22;9(1):93. PubMed PMID: 27658462; PubMed Central PMCID: PMC5034521.