Tanacetum huronense (Lake Huron tansy), which is native to the upper Midwest region of USA and Canada, was examined for the presence of anticancer compounds using an in vitro human tumor cell proliferation inhibition assay, with glioblastoma derived cell line U-87 MG. Bioassay-directed purification of the ethyl acetate extract of the aerial portion of this plant identified six active sesquiterpenoid lactones (1–6). Among these, compounds 5 and 6 are new structural analogs. One of the most abundant isolates, tanacin (4), exhibited the greatest inhibition with an IC50 value of 4.5 μg/mL.
TrianaJ., EiroaJ.L., MoralesM., PérezF.J., BrouardI., MarreroM.T., EstévezS., QuintanaJ., EstévezF., CastilloQ.A., LeónF. (2013) A chemotaxonomic study of endemic species of genus Tanacetum from the Canary Islands. Phytochemistry, 92, 87–104.
2.
DraglandS., RohloffJ., MordalR., IversenT.H. (2005) Harvest regimen optimization and essential oil production in five tansy (Tanacetum vulgare L.) genotypes under a northern climate. Journal of Agricultural and Food Chemistry, 53, 4946–4953.
3.
HoletzF.B., PessiniG.L., SanchesN.R., CortezD.A., NakamuraC.V., FilhoB.P.D. (2002) Screening of some plants used in the Brazilian folk medicine for the treatment of infectious diseases. Memórias do Instituto Oswaldo Cruz, 97, 1027–1031.
XieG., SchepetkinI.A., QuinnM.T. (2007) Immunomodulatory activity of acidic polysaccharides isolated from Tanacetum vulgare L. International Immunopharmacology, 7, 1639–1650.
6.
Juan-BadaturugeM., HabtemariamS., JacksonC., ThomasM.J. (2009) Antioxidant principles of Tanacetum vulgare L. aerial parts. Natural Product Communications, 4, 1561–1564.
7.
OnozatoT., NakamuraC.V., CortezD.A., Dias-FilhoB.P., Ueda-NakamuraT. (2009) Tanacetum vulgare: antiherpes virus activity of crude extract and the purified compound parthenolide. Phytotherapy Research, 23, 791–796.
8.
GhantousA., SinjabA., HercegZ., DarwicheN. (2013) Parthenolide: from plant shoots to cancer roots. Drug Discovery Today., 18, 894–905.
IbrahimS.R.M., BadrJ.M., El SayedK.A., YoussefD.T.A. (2007) A new cytotoxic sesquiterpene and three anti-inflammatory flavonoids from Egyptian Tanacetum santolinoides.Natural Product Communications, 2, 1071–1074.
11.
ZhangS., OngC.N., ShenH.M., (2004) Critical roles of intracellular thiols and calcium in parthenolide-induced apoptosis in human colorectal cancer cells. Cancer Letters, 208, 143–153.
12.
ParkJ.H., LiuL., KimI.H., KimJ.H., YouK.R., KimD.G. (2005) Identification of the genes involved in enhanced fenretinide-induced apoptosis by parthenolide in human hepatoma cells. Cancer Research, 65, 2804–2814.
13.
SohmaI., FujiwaraY., SugitaY., YoshiokaA., ShirakawaM., MoonJ.H., TakiguchiS., MiyataH., YamasakiM., MoriM., DokiY. (2011) Parthenolide, an NF-κB inhibitor, suppresses tumor growth and enhances response to chemotherapy in gastric cancer. Cancer Genomics Proteomics, 8, 39–47.
14.
KimJ.H., LiuL., LeeS.O., KimY.T., YouK.R., KimD.G. (2005) Susceptibility of cholangiocarcinoma cells to parthenolide-induced apoptosis. Cancer Research, 65, 6312–6320.
15.
LiuJ.W., CaiM.X., XinY., WuQ.S., MaJ., YangP., XieH.Y., HuangD.S. (2010) Parthenolide induces proliferation inhibition and apoptosis of pancreatic cancer cells in vitro.Journal of Experimental & Clinical Cancer Research, 29, 108–115.
16.
ChengG., XieL. (2011) Parthenolide induces apoptosis and cell cycle arrest of human 5637 bladder cancer cells in vitro.Molecules, 16, 6758–6768.
17.
KarimianH., FadaeinasabM., MoghadamtousS.Z., HajrezaeM., ZahedifardM., RazaviM., SafiS.Z., MohanS., KhalifaS.A.M., El-SeedR.H., AbdullaA.M., AliH.M., NoordinM.I. (2015) The chemopreventive effect of Tanacetum polycephalum against LA7-induced breast cancer in rats and the apoptotic effect of a cytotoxic sesquiterpene lactone in MCF7 cells: a bioassay-guided approach. Cellular Physiology and Biochemistry, 36, 988–1003.
18.
AndersonK.N., BejcekB.E. (2008) Parthenolide induces apoptosis in glioblastomas without affecting NF-kappaB. Journal of Pharmaceutical Sciences, 106, 318–320.
19.
SanzJ.F., MarcoJ.A. (1991) NMR Studies of tatridin A and some related sesquiterpene lactones from Tanacetum vulgare.Journal of Natural Products, 54, 591–596.
20.
KonstantinopoulouM., KariotiA., SkaltsasS., SkaltsaH. (2003) Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity. Journal of Natural Products, 66, 699–702.
21.
HajduZ., ZupkoI., RethyB., ForgoP., HohmannJ. (2010) Bioactivity-guided isolation of cytotoxic sesquiterpenes and flavonoids from Anthemis ruthenica.Planta Medica, 76, 94–96.
22.
LiuY., NairM.G. (2011) Labdane diterpenes in Curcuma mangga rhizomes inhibit lipid peroxidation, cyclooxygenase enzymes and human tumour cell proliferation. Food Chemistry, 124, 527–532.
23.
AliS.I., ZhangC-R, MohamedA.A., El-BazF.K., HegazyA.K., KordM.A., NairM.G. (2013) Major constituents of Boswellia carteri resin exhibit cyclooxygenase enzymes inhibition and antiproliferative activity. Natural Product Communications, 8, 1365–1366.
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