Semisynthesis and in vitro cytotoxic evaluation of new analogues of 1-O-acetylbritannilactone, a sesquiterpene from Inula britannica

European Journal of Medicinal Chemistry

Volumn 80, Issue , 2014, Pages 71-82

  Dong, Shuai ^a   Tang, Jiang Jiang ^a   Zhang, Cheng Chen ^a   Tian, Jun Mian ^a   Guo, Jun Tao ^a   Zhang, Qiang ^a   Li, He ^a   Gao, Jin Ming ^a  

^a NORTHWEST A F UNIVERSITY   (China)

Author keywords

1 O Acetylbritannilactone sesquiterpene; Cytotoxic activity; Structure activity relationship

Indexed keywords

1 O ACETYL 6 O (P BROMOCINNAMOYL)BRITANNILACTONE; 1 O ACETYL 6 O (P TRIFLUOROMETHYLCINNAMOYL)BRITANNILACTONE; 1 O ACETYL 6 O BUTYRYLBRITANNILACTONE; 1 O ACETYL 6 O CARBOXYPROPIONYLBRITANNILACTONE; 1 O ACETYL 6 O CHLORACETYLBRITANNILACTONE; 1 O ACETYL 6 O DECANOYLBRITANNILACTONE; 1 O ACETYL 6 O DECOYLBRITANNILACTONE; 1 O ACETYL 6 O HEPTANOYLBRITANNILACTONE; 1 O ACETYL 6 O HEXANOYLBRITANNILACTONE; 1 O ACETYL 6 O ISOBUTYRYLBRITANNILACTONE; 1 O ACETYL 6 O LAUROYLBRITANNILACTONE; 1 O ACETYL 6 O MYRISTOYLBRITANNILACTONE; 1 O ACETYL 6 O NONANOYLBRITANNILACTONE; 1 O ACETYL 6 O PIVALOYLBRITANNILACTONE; 1 O ACETYL 6 O PROPIONYLBRITANNILACTONE; 1 O ACETYL 6 O STEAROYLBRITANNILACTONE; 1 O ACETYL 6 O VALERYLBRITANNILACTONE; 1 O ACETYL 6 OXOBRITANNILACTONE; 1 O ACETYLBRITANNILACTONE; 1,6 O,O DIACETYL 13 (3,4,5 TRIMETHOXYPHENYL)BRITANNILACTONE; 1,6 O,O DIACETYL 13 (4 BROMOPHENYL)BRITANNILACTONE; 1,6 O,O DIACETYL 13 (4 FLUOROPHENYL)BRITANNILACTONE; 1,6 O,O DIACETYL 13 (4 METHOXYPHENYL)BRITANNILACTONE; 1,6 O,O DIACETYL 13 PHENYLBRITANNILACTONE; 1,6 O,O DIACETYLBRITANNILACTONE; ANTINEOPLASTIC AGENT; ETOPOSIDE; HERBACEOUS AGENT; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG; ACETYLBRITANNILATONE; LACTONE;

ACETYLATION; ANIMAL CELL; APOPTOSIS; ARTICLE; BIOASSAY; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL CYCLE M PHASE; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; INULA; INULA BRITANNICA; LIPOPHILICITY; NONHUMAN; OPTICAL ROTATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION; ANIMAL; CELL CYCLE; CHEMISTRY; CHO CELL LINE; CRICETULUS; DRUG EFFECTS; HAMSTER; IC50; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; CELL LINE, TUMOR; CHEMISTRY TECHNIQUES, SYNTHETIC; CHO CELLS; CRICETINAE; CRICETULUS; HUMANS; INHIBITORY CONCENTRATION 50; INULA; LACTONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84899062747     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.04.028     Document Type: Article

References (42)

1. F. Bohlmann, P.K. Mahanta, J. Jakupovic, R.C. Rastogi, and A.A. Natu New sesquiterpene lactones from Inula species Phytochemistry 17 1978 1165 1172
2. F. Jeske, S. Huneck, and J. Jakupovic Secoeudesmanolides from Inula japonica Phytochemistry 34 1993 1647 1649 (Pubitemid 2027695)
3. B.-N. Zhou, N.-S. Bai, L.-Z. Lin, and G. Cordell Sesquiterpene lactones from Inula britannica Phytochemistry 34 1993 249 252
4. X.M. Fang, B. Liu, Y.B. Liu, J.J. Wang, J.K. Wen, B.H. Li, and M. Han Acetylbritannilactone suppresses growth via upregulation of kruppel-like transcription factor 4 expression in HT-29 colorectal cancer cells Oncology Reports 26 2011 1181 1187
5. C.-T. Ho, M. Rafi, R.S. Dipaola, G. Ghai, R.T. Rosen, N. Bai, Inducing Cell Apoptosis and Treating Cancer Using 1-O-Acetylbritannilactone or 1, 6-O, O-Diacetylbritannilactone, US 6627623, 2003.
6. J.-L. Qi, Y. Fu, X.-W. Shi, Y.-B. Wu, Y.-Z. Wang, D.-Q. Zhang, and Q.-W. Shi Sesquiterpene lactones and their anti-tumor activity from the flowers of Inula britannica Letters in Drug Design & Discovery 5 2008 433 436
7. K.-H. Je, A.-R. Han, H.-T. Lee, W. Mar, and E.-K. Seo The inhibitory principle of lipopolysaccharide-induced nitric oxide production from Inula britannica var. chinensis Archives of Pharmacal Research 27 2004 83 85 (Pubitemid 43154546)
8. B. Liu, M. Han, and J.K. Wen Acetylbritannilactone inhibits neointimal hyperplasia after balloon injury of rat artery by suppressing nuclear factor-kappa B activation The Journal of Pharmacology and Experimental Therapeutics 324 2008 292 298 (Pubitemid 350294152)
9. M.M. Rafi, N.-S. Bai, C.-T. Ho, R.T. Rosen, E. White, D. Perez, and R.S. DiPaola A sesquiterpenelactone from Inula britannica induces anti-tumor effects dependent on Bcl-2 phosphorylation Anticancer Research 25 2005 313 318 (Pubitemid 40470125)
10. M. Han, J.K. Wen, B. Zheng, and D.Q. Zhang Acetylbritannilatone suppresses NO and PGE2 synthesis in RAW 264.7 macrophages through the inhibition of iNOS and COX-2 gene expression Life Sciences 75 2004 675 684 (Pubitemid 38686699)
11. M.H. Pan, Y.S. Chiou, A.C. Cheng, N. Bai, C.Y. Lo, D. Tan, and C.T. Ho Involvement of MAPK, Bcl-2 family, cytochrome c, and caspases in induction of apoptosis by 1,6-O,O-diacetylbritannilactone in human leukemia cells Molecular Nutrition & Food Research 51 2007 229 238 (Pubitemid 47083254)
12. Y.P. Liu, J.K. Wen, Y.B. Wu, J. Zhang, B. Zheng, D.Q. Zhang, and M. Han 1,6-O,O-diacetylbritannilactones inhibits IkappaB kinase beta-dependent NF-kappaB activation Phytomedicine 16 2009 156 160
13. B. Liu, J.K. Wen, B.H. Li, X.M. Fang, J.J. Wang, Y.P. Zhang, C.J. Shi, D.Q. Zhang, and M. Han Celecoxib and acetylbritannilactone interact synergistically to suppress breast cancer cell growth via COX-2-dependent and -independent mechanisms Cell Death & Disease 2 2011 e185 e193
14. S. Liu, H. Liu, W. Yan, L. Zhang, N. Bai, and C.T. Ho Studies on 1-O-acetylbritannilactone and its derivative, (2-O-butyloxime-3-phenyl)- propionyl-1-O-acetylbritannilactone ester Bioorganic & Medicinal Chemistry Letters 14 2004 1101 1104 (Pubitemid 38229835)
15. S. Liu, H. Liu, W. Yan, L. Zhang, N. Bai, and C.T. Ho Design, synthesis, and anti-tumor activity of (2-O-alkyloxime-3-phenyl)-propionyl-1-O- acetylbritannilactone esters Bioorganic & Medicinal Chemistry 13 2005 2783 2789 (Pubitemid 40387488)
16. S. Amslinger The tunable functionality of α,β-unsaturated carbonyl compounds enables their differential application in biological systems ChemMedChem 5 2010 351 356
17. S.M. Kupchan, D.C. Fessler, M.A. Eakin, and T.J. Giacobbe Reactions of alpha methylene lactone tumor inhibitors with model biological nucleophiles Science 168 1970 376 378
18. A. Janecka, A. Wyrebska, K. Gach, J. Fichna, and T. Janecki Natural and synthetic alpha-methylenelactones and alpha-methylenelactams with anticancer potential Drug Discovery Today 17 2012 561 572
19. M.L. Guzman, R.M. Rossi, L. Karnischky, X. Li, D.R. Peterson, D.S. Howard, and C.T. Jordan The sesquiterpene lactone parthenolide induces apoptosis of human acute myelogenous leukemia stem and progenitor cells Blood 105 2005 4163 4169 (Pubitemid 40720758)
20. A. Wyrebska, J. Szymanski, K. Gach, J. Piekielna, J. Koszuk, T. Janecki, and A. Janecka Apoptosis-mediated cytotoxic effects of parthenolide and the new synthetic analog MZ-6 on two breast cancer cell lines Molecular Biology Reports 40 2013 1655 1663
21. T.J. Schmidt Helenanolide-type sesquiterpene lactones-III. Rates and stereochemistry in the reaction of helenalin and related helenanolides with sulfhydryl containing biomolecules Bioorganic & Medicinal Chemistry 5 1997 645 653 (Pubitemid 27199388)
22. W.-N. Wang, Y.-Z. Wang, and D.-Q. Zhang Study on RP-HPLC determination of 1-O-acetylbritannilactone in Inula britannica L Chinese Journal of Pharmaceutical Analysis 2 2005 205 207
23. D. Zhang, J. Wen, Y. Wu, Y. Fu, W. Yunzhi, X. Shi, J. Qi, 1-O-Acetylbritannilactone Derivative, its Preparation Method and Application as Antitumor Agent, CN101186598, 2008.
24. 2-terminal kinase activation Breast Cancer Research: BCR 12 2010 R9
25. J.M. Gao, J.W. Shen, J.Y. Wang, Z. Yang, and A.L. Zhang Microbial transformation of 3beta-acetoxypregna-5,16-diene-20-one by Penicillium citrinum Steroids 76 2011 43 47
26. N.J. Fan, J.J. Tang, H. Li, X.J. Li, B. Luo, and J.M. Gao Synthesis and cytotoxic activity of some novel steroidal C-17 pyrazolinyl derivatives European Journal of Medicinal Chemistry 69 2013 182 190
27. J.J. Tang, F.Y. Zhang, D.M. Wang, J.M. Tian, S. Dong, and J.M. Gao Semisynthesis and antifeedant activity of new derivatives of a dihydro-beta-agarofuran from Parnassia wightiana International Journal of Molecular Sciences 14 2013 19484 19493
28. C. Han, F.J. Barrios, M.V. Riofski, and D.A. Colby Semisynthetic derivatives of sesquiterpene lactones by palladium-catalyzed arylation of the alpha-methylene-gamma-lactone substructure The Journal of Organic Chemistry 74 2009 7176 7179
29. A. Arcadi, M. Chiarini, F. Marinelli, Z. Berente, and L. Kollar Palladium-catalyzed arylation of alpha-methylene-gamma-butyrolactone: 3-benzylfuran-2(5H)-ones vs (Z)-benzylidene-gamma-butyrolactones and their reduction to 3-benzyl-gamma butyrolactones Organic Letters 2 2000 69 72
30. A.R. Han, W. Mar, and E.K. Seo X-ray crystallography of a new sesquiterpene lactone isolated from Inula britannica var. chinensis Natural Product Sciences 9 2003 28 30 (Pubitemid 36427888)
31. H.Q. Gong, Q.X. Wu, L.L. Liu, J.L. Yang, R. Wang, and Y.P. Shi Sesquiterpenoids from the aerial parts of Inula japonica Helvetica Chimica Acta 94 2011 1269 1276
32. CCDC-940163 (natural ABL) and CCDC-987147 (compound 23) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
33. J. Merten, Y. Wang, T. Krause, O. Kataeva, and P. Metz Total synthesis of the cytotoxic 1,10-seco-eudesmanolides britannilactone and 1,6-O,O- diacetylbritannilactone Chemistry - A European Journal 17 2011 3332 3334
34. I.P. Beletskaya, and A.V. Cheprakov The Heck reaction as a sharpening stone of palladium catalysis Chemical Reviews 100 2000 3009 3066
35. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, and M.R. Boyd New colorimetric cytotoxicity assay for anticancer-drug screening The Journal of the National Cancer Institute 82 1990 1107 1112 (Pubitemid 20213250)
36. N. Bai, C.-S. Lai, K. He, Z. Zhou, L. Zhang, Z. Quan, N. Zhu, Q.Y. Zheng, M.-H. Pan, and C.-T. Ho Sesquiterpene lactones from Inula britannica and their cytotoxic and apoptotic effects on human cancer cell lines Journal of Natural Products 69 2006 531 535 (Pubitemid 43798096)
37. L. Raj, T. Ide, A.U. Gurkar, M. Foley, M. Schenone, X. Li, N.J. Tolliday, T.R. Golub, S.A. Carr, A.F. Shamji, A.M. Stern, A. Mandinova, S.L. Schreiber, and S.W. Lee Selective killing of cancer cells by a small molecule targeting the stress response to ROS Nature 475 2011 231 234
38. F.A. Oberhammer, M. Pavelka, S. Sharma, R. Tiefenbacher, A.F. Purchio, W. Bursch, and R. Schultehermann Induction of apoptosis in cultured hepatocytes and in regressing liver by transforming growth factor beta 1 Proceedings of the National Academy of Sciences of the United States of America 89 1992 5408 5412
39. J.J. Tang, G.J. Fan, F. Dai, D.J. Ding, Q. Wang, D.L. Lu, R.R. Li, X.Z. Li, L.M. Hu, X.L. Jin, and B. Zhou Finding more active antioxidants and cancer chemoprevention agents by elongating the conjugated links of resveratrol Free Radical Biology & Medicine 50 2011 1447 1457
40. O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A. Howard, and H. Puschmann OLEX2: a complete structure solution, refinement and analysis program Journal of Applied Crystallography 42 2009 339 341
41. L. Palatinus, and G. Chapuis SUPERFLIP-a computer program for the solution of crystal structures by charge flipping in arbitrary dimensions Journal of Applied Crystallography 40 2007 786 790 (Pubitemid 47080274)
42. G.M. Sheldrick A short history of SHELX Acta Crystallographica Section A 64 2007 112 122