A comparative study of proapoptotic potential of cyano analogues of boswellic acid and 11-keto-boswellic acid

European Journal of Medicinal Chemistry

Volumn 46, Issue 4, 2011, Pages 1356-1366

  Kaur, Rajbir ^a   Khan, Sheema ^a   Chib, Renu ^a   Kaur, Tandeep ^a   Sharma, Parduman Raj ^a   Singh, Jaswant ^a   Shah, Bhahwal Ali ^a   Taneja, Subhash Chandra ^a  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

Author keywords

Anti cancer; Apoptosis; Boswellic acids; Cytotoxicity; Triterpenoids

Indexed keywords

11 KETO BOSWELLIC ACID; 2 CARBAMOYL 3 HYDROXY 11 OXOURS 12 EN 24 OIC ACID; 2 CARBAMOYL 3 HYDROXY URS 12 EN 24 OIC ACID; 3 HYDROXY 4 ISOCYANATO 11 OXOURS 12 EN 2 CARBOXAMIDE; 3 HYDROXY 4 ISOCYANATO URS 12 EN 2 CARBOXAMIDE; 4 AMINO 3 HYDROXY 11 OXOURS 12 EN 2 CARBOXAMIDE; 4 AMINO 3 HYDROXY URS 12 EN 2 CARBOXAMIDE; ANTINEOPLASTIC AGENT; BOSWELLIC ACID; BUTYL 11 OXOISOXAZOLE[4,5 B]URS 12 EN 24 OATE; BUTYL 2 CYANO 3 HYDROXY 11 OXO URS 1,12 DIEN 24 OATE; BUTYL 2 CYANO 3 OXO URS 1,12 DIEN 24 OATE; BUTYL 2 CYANO 3 OXO URS 12 EN 24 OATE; BUTYL 2 CYANO 3,11 DIOXO URS 1,12 DIEN 24 OATE; BUTYL 2 CYANO 3,11 DIOXO URS 12 EN 24 OATE; BUTYL 2 CYNO 3 HYDROXY 11 OXO URS 12 EN 24 OATE; BUTYL 2 HYDROXYMETHYLEN 3 OXO URS 12 EN 24 OATE; BUTYL 2 HYDROXYMETHYLEN 3,11 DIOXO URS 12 EN 24 OATE; BUTYL 3 ALPHA ACETOXY 11 OXO URS 12 EN 24 OATE; BUTYL 3 ALPHA ACETOXY URS 12 EN 24 OATE; BUTYL 3 ALPHA HYDROXY 11 OXO URS 12 EN 24 OATE; BUTYL 3 ALPHA HYDROXY URS 12 EN 24 OATE; BUTYL 3 OXO URS 12 EN 24 OATE; BUTYL 3,11 DIOXO URS 12 EN 24 OATE; BUTYL ISOXAZOLE[4,5 B]URS 12 EN 24 OATE; DNA; LIPOCORTIN 5; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BIOLOGICAL ACTIVITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA FRAGMENTATION; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA CELL; MYELOID LEUKEMIA; UTERINE CERVIX CARCINOMA;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; HELA CELLS; HL-60 CELLS; HUMANS; NITRILES; OXYGEN; TRITERPENES;

EID: 79952280699     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.01.061     Document Type: Article

References (42)

1. K.M. Debatin Activation of apoptosis pathways by anticancer treatment Toxicol. Lett. 112 2000 41 48
2. B.A. Shah, G.N. Qazi, and S.C. Taneja Boswellic acids: a group of medicinally important compounds Nat. Prod. Rep. 26 2009 72 89 (references cited therein)
3. S. Singh, A. Khajuria, S.C. Taneja, R.K. Khajuria, J. Singh, and G.N. Qazi Boswellic acids and glucosamine show synergistic effect in preclinical anti-inflammatory study in rats Bioorg. Med. Chem. Lett. 17 2007 3706 3711 (Pubitemid 46898805)
4. S. Singh, A. Khajuria, S.C. Taneja, R.K. Johri, J. Singh, and G.N. Qazi Boswellic acids: a leukotriene inhibitor also effective through topical application in inflammatory disorders Phytomedicine 15 2008 400 407
5. H.P. Ammon Boswellic acids in chronic inflammatory diseases Planta Med. 72 2006 1100 1116 (Pubitemid 44638909)
6. D. Khanna, G. Sethi, K.S. Ahn, M.K. Pandey, A.B. Kunnumakkara, B. Sung, A. Aggarwal, and B.B. Aggarwal Natural products as a gold mine for arthritis treatment Curr. Opin. Pharmacol. 7 2007 344 351 (Pubitemid 46731200)
7. I. Gupta, A. Parihar, P. Malhotra, G.B. Singh, R. Ludtke, H. Safayhi, and H.P. Ammon Effects of Boswellia serrata gum resin in patients with ulcerative colitis Eur. J. Med. Res. 2 1997 37 43
8. S. Singh, A. Khajuria, S.C. Taneja, R.K. Khajuria, J. Singh, R.K. Johri, and G.N. Qazi The gastric ulcer protective effect of boswellic acids, a leukotriene inhibitor from Boswellia serrata, in rats Phytomedicine 15 2008 408 415
9. I. Gupta, A. Parihar, P. Malhotra, S. Gupta, R. Ludtke, H. Safayhi, and H.P. Ammon Effects of gum resin of Boswellia serrata in patients with chronic colitis Planta Med. 67 2001 391 395 (Pubitemid 32652571)
10. A. Gupta, V. Gupta, A. Parihar, S. Gupta, R. Ludtke, H. Safayhi, and H.P. Ammon Effects of Boswellia serrata gum resin in patients with bronchial asthma: results of a double-blind, placebo-controlled, 6-week clinical study Eur. J. Med. Res. 3 1998 511 514
11. H. Safayhi, T. Mack, and H.P. Ammon Protection by boswellic acids against galactosamine/ endotoxin-induced hepatitis in mice Biochem. Pharmacol. 41 1991 1536 1537
12. R. Han Highlight on the studies of anticancer drugs derived from plants in China Stem Cells 12 1994 53 63 (Pubitemid 24045786)
13. S. Bhushan, A. Kumar, F. Malik, S.S. Andotra, V.K. Sethi, I.P. Kour, S.C. Taneja, G.N. Qazi, and J. Singh A triterpenediol from Boswellia serrata induces apoptosis through both the intrinsic and extrinsic apoptotic pathways in human leukemia HL-60 cells Apoptosis 12 2007 1911 1926 (Pubitemid 47498241)
14. G. Jannsen, U. Bode, H. Breu, B. Dohm, V. Engelbrecht, and U. Gobel Boswellic acids in the palliative therapy of children with progressive or relapsed brain tumors Klin. Padiatr. 212 2000 189 195 (Pubitemid 30650553)
15. M. Winkling, S. Sarikaya, A. Rahmanian, A. Jodicke, and D.K. Boker Boswellic acids inhibit glioma growth: a new treatment option? J. Neurooncol. 46 2000 97 103 (Pubitemid 30352616)
16. T. Glaser, S. Winter, P. Groscurth, H. Safayhi, E.R. Sailer, and H.P. Ammon Boswellic acids and malignant glioma: induction of apoptosis but no modulation of drug sensitivity Br. J. Cancer 80 1999 756 765 (Pubitemid 29209838)
17. J.J. Liu, A. Nilsson, S. Oredsson, V. Badmaev, W.Z. Zhao, and R.D. Duan Boswellic acids trigger apoptosis via a pathway dependent on caspase-8 activation but independent on Fas/Fas ligand interaction in colon cancer HT-29 cells Carcinogenesis 23 2002 2087 2093 (Pubitemid 36104960)
18. R.F. Hoernlein, T. Orlikowsky, C. Zehrer, D. Niethammer, E.R. Sailer, T. Simmet, G.E. Dannecker, and H.P. Ammon Acetyl-11-keto-beta-boswellic acid induces apoptosis in HL-60 and CCRF-CEM cells and inhibits topoisomerase I J. Pharmacol. Exp. Ther. 288 1999 613 619 (Pubitemid 29119672)
19. Y. Jing, S. Nakajo, L. Xia, K. Nakaya, Q. Fang, S. Waxman, and R. Han Boswellic acid acetate induces differentiation and apoptosis in leukemia cell lines Leuk. Res. 23 1999 43 50 (Pubitemid 28484867)
20. T. Syrovets, B. Buchele, E. Gedig, J.R. Slupsky, and T. Simmet Acetyl-boswellic acids are novel catalytic inhibitors of human topoisomerases I and IIα Mol. Pharmacol. 58 2000 71 81 (Pubitemid 30452529)
21. T. Honda, B.V. Rounds, G.W. Gribble, N. Suh, Y. Wang, and M.B. Sporn Design and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages Bioorg. Med. Chem. Lett. 8 1998 2711 2714 (Pubitemid 28496657)
22. T. Honda, G.W. Gribble, N. Suh, H.J. Finlay, B.V. Rounds, L. Bore, F.G. Favarolo Jr., Y. Wang, and M.B. Sporn Novel synthetic oleanane and ursane triterpenoids with various enone functionalities in ring A as inhibitors of nitric oxide production in mouse macrophages J. Med. Chem. 43 2000 1866 1877 (Pubitemid 30305019)
23. G. Chadalapaka, I. Jutooru, A. McAlees, T. Stefanac, and S. Safe Structure-dependent inhibition of bladder and pancreatic cancer cell growth by 2-substituted glycyrrhetinic and ursolic acid derivatives Bioorg. Med. Chem. Lett. 18 2008 2633 2639 (Pubitemid 351503883)
24. S. Chintharlapalli, S. Papineni, I. Jutooru, A. McAlees, and S. Safe Structure-dependent activity of glycyrrhetinic acid derivatives as peroxisome proliferator-activated receptor {gamma} agonists in colon cancer cells Mol. Cancer Ther. 6 2007 1588 1598 (Pubitemid 46954026)
25. Y.-J. You, Y. Kim, N.-H. Nam, and B.-Z. Ahn Synthesis and cytotoxic activity of A-ring modified betulinic acid derivatives Bioorg. Med. Chem. Lett. 13 2003 3137 3140 (Pubitemid 37093815)
26. T. Honda, K.T. Liby, X. Su, C. Sundararajan, Y. Honda, N. Suh, R. Risingsong, C.R. Williams, D.B. Royce, M.B. Sporn, and G.W. Gribble Design, synthesis, and antiinflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A Bioorg. Med. Chem. Lett. 16 2006 6306 6309 (Pubitemid 44709900)
27. K. Liby, T. Honda, C.R. Williams, R. Risingsong, D.B. Royce, N. Suh, A.T. Dinkova-Kostova, K.K. Stephenson, P. Talalay, C. Sundararajan, G.W. Gribble, and M.B. Sporn Novel semisynthetic analogues of betulinic acid with diverse cytoprotective, antiproliferative, and proapoptotic activities Mol. Cancer Ther. 6 2007 2113 2119 (Pubitemid 47052502)
28. S. Chintharlapalli, S. Papineni, S. Liu, I. Jutooru, G. Chadalapaka, S.-D. Cho, R.S. Murthy, Y. You, and S. Safe 2-cyano-lup-1-en-3-oxo-20-oic acid, a cyano derivative of betulinic acid, activates peroxisome proliferator- activated receptor gamma in colon and pancreatic cancer cells Carcinogenesis 28 2007 2337 2346 (Pubitemid 350111592)
29. A. Koohang, N.D. Majewski, E.L. Szotek, A.A. Mar, D.A. Eiznhamer, M.T. Flavin, and Z.Q. Xu Synthesis and cytotoxicity of 2-cyano-28-hydroxy-lup-1- en-3-ones Bioorg. Med. Chem. Lett. 19 2009 2168 2171
30. K.T. Liby, M.M. Yore, and M.B. Sporn Triterpenoids and rexinoids as multifunctional agents for the prevention and treatment of cancer Nat. Rev. Cancer 7 2007 357 369 (Pubitemid 46652485)
31. B.A. Shah, R. Kaur, P. Gupta, A. Kumar, V.K. Sethi, S.S. Andotra, J. Singh, A.K. Saxena, and S.C. Taneja Structure-activity relationship (SAR) of parthenin analogues with pro-apoptotic activity: development of novel anti-cancer leads Bioorg. Med. Chem. Lett. 19 2009 4394 4398
32. A. Kumar, F. Malik, S. Bhushan, V.K. Sethi, A.K. Shahi, J. Kour, S.C. Taneja, G.N. Qazi, and J. Singh An essential oil and its major constituent isointermedeol induce apoptosis by increased expression of mitochondrial cytochrome c and apical death receptors in human leukaemia HL-60 cells Chem. Biol. Interact. 171 2008 332 347
33. B.A. Shah, R. Chib, P. Gupta, V.K. Sethi, S. Koul, S.S. Andotra, A. Nargota, S. Sharma, A. Panday, S. Bani, B. Purnima, and S.C. Taneja Saponins as novel TNF-α inhibitors: isolation of saponins and a nor-pseudoguaianolide from Parthenium hysterophorus Org. Biomol. Chem. 7 2009 3230 3235
34. B.A. Shah, S.C. Taneja, V.K. Sethi, P. Gupta, S.S. Andotra, S.S. Chimni, and G.N. Qazi The formation of novel 1,3-dioxolanes: a typical Baylis-Hillman reaction of a sesquiterpene lactone parthenin Tetrahedron Lett. 48 2007 955 960 (Pubitemid 46091677)
35. B.A. Shah, A. Kumar, P. Gupta, M. Sharma, V.K. Sethi, A.K. Saxena, J. Singh, G.N. Qazi, and S.C. Taneja Cytotoxic and apoptotic activities of novel amino analogues of boswellic acids Bioorg. Med. Chem. Lett. 17 2007 6411 6416 (Pubitemid 350026349)
36. G.S.R.S. Rao, P. Kondaiah, S.K. Singh, P. Ravanan, and M.B. Sporn Chemical modifications of natural triterpenes - glycyrrhetinic and boswellic acids: evaluation of their biological activity Tetrahedron 64 2008 11541 11548 (Pubitemid 50318657)
37. D.E. Fisher Apoptosis in cancer therapy: crossing the threshold Cell 78 1994 539 542 (Pubitemid 24268576)
38. A.H. Wyllie, J.F. Kerr, and A.R. Currie Cell death: the significance of apoptosis Int. Rev. Cytol. 68 1980 251 306 (Pubitemid 11219226)
39. S. Rello, J.C. Stockert, V. Moreno, A. Gamez, M. Pacheco, A. Juarranz, M. Canete, and A. Villanueva Morphological criteria to distinguish cell death induced by apoptotic and necrotic treatments Apoptosis 10 2005 201 208 (Pubitemid 40558128)
40. P.R. Sharma, D.M. Mondhe, M. Shanmugavel, H.C. Pal, A.K. Shahi, A.K. Saxena, and G.N. Qazi Anticancer activity of an essential oil from Cymbopogon flexuosus Chem. Biol. Interact. 179 2008 160 168
41. S. Bhushan, J. Singh, M.J. Rao, A.K. Saxena, and G.N. Qazi A novel lignan composition from Cedrus deodara induces apoptosis and early nitric oxide generation in human leukemia Molt-4 and HL-60 cells Nitric Oxide 14 2006 72 88
42. Z. Yu, and W. Li Induction of apoptosis by puerarin in colon cancer HT-29 cells Cancer Lett. 238 2006 53 60 (Pubitemid 43851146)