Autoxidative and cyclooxygenase-2 catalyzed transformation of the dietary chemopreventive agent curcumin

Journal of Biological Chemistry

Volumn 286, Issue 2, 2011, Pages 1114-1124

  Griesser, Markus ^a,c   Pistis, Valentina ^a   Suzuki, Takashi ^a   Tejera, Noemi ^a   Pratt, Derek A ^b   Schneider, Claus ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b QUEEN S UNIVERSITY   (Canada)

^c BASF SE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

5-EXO CYCLIZATION; ANTICANCER DRUG; CHEMOPREVENTIVE ACTIVITY; CHEMOPREVENTIVE AGENTS; CLEAVAGE PRODUCTS; CURCUMIN; CYCLOOXYGENASE 2; DIPHENOLS; FERULIC ACIDS; HYDROGEN ABSTRACTION; IN-CELL; INDOMETHACIN; NON-ENZYMATIC; OXIDATIVE TRANSFORMATIONS; PEROXIDASE ACTIVITIES; PH-DEPENDENT; PHENOLIC HYDROXYL; PHENOLIC RINGS; QUINONE METHIDE;

CATALYSIS; CYCLIZATION; DEGRADATION; OXIDATION; OXYGENATION; PHENOLS;

BIOLOGICAL WATER TREATMENT;

ALIPHATIC KETONE; BICYCLOPENTADIONE; CURCUMIN; CYCLOOXYGENASE 2; INDOMETACIN; LIPOPOLYSACCHARIDE; OXYGEN; PARACETAMOL; PEROXIDASE; PHENOL; QUINONE DERIVATIVE; QUINONE METHIDE; UNCLASSIFIED DRUG; VANILLIN;

ANIMAL CELL; ARTICLE; CATALYSIS; CELLULAR DISTRIBUTION; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYCLIZATION; DEGRADATION KINETICS; DRUG ACTIVITY; DRUG DETERMINATION; DRUG STRUCTURE; DRUG TRANSFORMATION; ENZYME ACTIVITY; HYDRATION; MOUSE; NONHUMAN; OXIDATION; OXYGEN CONSUMPTION; OXYGENATION; PH; PRIORITY JOURNAL; PROTEIN FOLDING; REACTION ANALYSIS; STOICHIOMETRY;

ANIMALS; ANTINEOPLASTIC AGENTS; BUFFERS; CELL TRANSFORMATION, NEOPLASTIC; CELLS, CULTURED; CURCUMIN; CYCLOOXYGENASE 2; HUMANS; MACROPHAGES; MICE; NEOPLASMS; OXIDATION-REDUCTION; OXYGEN; PLACENTAL LACTOGEN; SIGNAL TRANSDUCTION; SPODOPTERA;

EID: 78651401023     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M110.178806     Document Type: Article

References (56)

1. Aggarwal, B. B., and Sung, B. (2009) Trends Pharmacol. Sci. 30, 85-94
2. Aggarwal, B. B., and Shishodia, S. (2006) Biochem. Pharmacol. 71, 1397-1421
3. Hatcher, H., Planalp, R., Cho, J., Torti, F. M., and Torti, S. V. (2008) Cell. Mol. Life Sci. 65, 1631-1652
4. Tønnesen, H. H., Karlsen, J., and van Henegouwen, G. B. (1986) Z. Lebensm. Unters. Forsch. 183, 116-122
5. Khurana, A., and Ho, C. T. (1988) J. Liquid Chromatogr. 11, 2295-2304
6. Tonnesen, H. H., and Karlsen, J. (1985) Z. Lebensm. Unters. Forsch. 180, 132-134
7. Wang, Y. J., Pan, M. H., Cheng, A. L., Lin, L. I., Ho, Y. S., Hsieh, C. Y., and Lin, J. K. (1997) J. Pharm. Biomed. Anal. 15, 1867-1876
8. Pfeiffer, E., Hoehle, S. I., Solyom, A. M., and Metzler, M. (2003) J. Food Eng. 56, 257-259
9. Dempe, J. S., Pfeiffer, E., Grimm, A. S., and Metzler, M. (2008) Mol. Nutr. Food Res. 52, 1074-1081
10. Appiah-Opong, R., Commandeur, J. N., van Vugt-Lussenburg, B., and Vermeulen, N. P. (2007) Toxicology 235, 83-91
11. Shen, L., and Ji, H. F. (2009) Clin. Cancer Res. 15, 7108-7109
12. Dhillon, N., Sung, B., Kurzrock, R., and Aggarwal, B. B. (2009) Clin. Cancer Res. 15, 7108-7109
13. Reddy, B. S., and Rao, C. V. (2002) J. Environ. Pathol. Toxicol. Oncol. 21, 155-164
14. Murakami, A., and Ohigashi, H. (2007) Int. J. Cancer 121, 2357-2363
15. Marnett, L. J., and DuBois, R. N. (2002) Annu. Rev. Pharmacol. Toxicol. 42, 55-80
16. Sharma, R. A., McLelland, H. R., Hill, K. A., Ireson, C. R., Euden, S. A., Manson, M. M., Pirmohamed, M., Marnett, L. J., Gescher, A. J., and Steward, W. P. (2001) Clin. Cancer Res. 7, 1894-1900
17. Garcea, G., Berry, D. P., Jones, D. J., Singh, R., Dennison, A. R., Farmer, P. B., Sharma, R. A., Steward, W. P., and Gescher, A. J. (2005) Cancer Epidemiol. Biomarkers Prev. 14, 120-125
18. Plummer, S. M., Holloway, K. A., Manson, M. M., Munks, R. J., Kaptein, A., Farrow, S., and Howells, L. (1999) Oncogene 18, 6013-6020
19. Goel, A., Boland, C. R., and Chauhan, D. P. (2001) Cancer Lett. 172, 111-118
20. Ramsewak, R. S., DeWitt, D. L., and Nair, M. G. (2000) Phytomedicine 7, 303-308
21. Koeberle, A., Northoff, H., and Werz, O. (2009) Mol. Cancer Ther. 8, 2348-2355
22. Huang, M. T., Lysz, T., Ferraro, T., Abidi, T. F., Laskin, J. D., and Conney, A. H. (1991) Cancer Res. 51, 813-819
23. Prasad, N. S., Raghavendra, R., Lokesh, B. R., and Naidu, K. A. (2004) Prostaglandins Leukot. Essent. Fatty Acids 70, 521-528
24. Rao, C. V. (2007) Adv. Exp. Med. Biol. 595, 213-226
25. Schneider, C., Amberg, A., Feurle, J., Ross, A., Roth, M., Tóth, G., and Schreier, P. (1998) J. Mol. Catalysis B: Enzymatic 4, 219-227
26. Pabon, H. J. (1964) Recl. Trav. Chim. Pays Bas. 83, 379-386
27. Schneider, C., Boeglin, W. E., and Brash, A. R. (2004) J. Biol. Chem. 279, 4404-4414
28. Klegeris, A., Korkina, L. G., and Greenfield, S. A. (1995) Free Radic. Biol. Med. 18, 215-222
29. Toth, G., Roth, M., Weckerle, B., and Schreier, P. (2000) Magn. Res. Chem. 38, 51-54
30. Porter, N. A., Caldwell, S. E., and Mills, K. A. (1995) Lipids 30, 277-290
31. Schneider, C., Pratt, D. A., Porter, N. A., and Brash, A. R. (2007) Chem. Biol. 14, 473-488
32. Aronoff, D. M., Oates, J. A., and Boutaud, O. (2006) Clin. Pharmacol. Ther. 79, 9-19
33. Litwinienko, G., and Ingold, K. U. (2004) J. Org. Chem. 69, 5888-5896
34. Markey, C. M., Alward, A., Weller, P. E., and Marnett, L. J. (1987) J. Biol. Chem. 262, 6266-6279
35. Bolton, J. L., Comeau, E., and Vukomanovic, V. (1995) Chem. Biol. Interact. 95, 279-290
36. Barclay, L. R., Vinqvist, M. R., Mukai, K., Goto, H., Hashimoto, Y., Tokunaga, A., and Uno, H. (2000) Org. Lett. 2, 2841-2843
37. Jovanovic, S. V., Steenken, S., Boone, C. W., and Simic, M. G. (1999) J. Am. Chem. Soc. 121, 9677-9681
38. Galano, A., Alvarez-Diduk, R., Ramirez-Silva, M. T., Alarcon-Angeles, G., and Rojas-Hernandez, A. (2009) Chem. Phys. 363, 13-23
39. Thompson, D., Constantin-Teodosiu, D., Norbeck, K., Svensson, B., and Moldéus, P. (1989) Chem Res Toxicol 2, 186-192
40. Szewczuk, L. M., Lee, S. H., Blair, I. A., and Penning, T. M. (2005) J. Nat. Prod. 68, 36-42
41. Werz, O. (2007) Planta Med. 73, 1331-1357
42. Skrzypczak-Jankun, E., Zhou, K., McCabe, N. P., Selman, S. H., and Jankun, J. (2003) Int. J. Mol. Med. 12, 17-24
43. Ireson, C., Orr, S., Jones, D. J., Verschoyle, R., Lim, C. K., Luo, J. L., Howells, L., Plummer, S., Jukes, R., Williams, M., Steward, W. P., and Gescher, A. (2001) Cancer Res. 61, 1058-1064
44. Pan, M. H., Lin-Shiau, S. Y., and Lin, J. K. (2000) Biochem. Pharmacol. 60, 1665-1676
45. Liu, Z., Xie, Z., Jones, W., Pavlovicz, R. E., Liu, S., Yu, J., Li, P. K., Lin, J., Fuchs, J. R., Marcucci, G., Li, C., and Chan, K. K. (2009) Bioorg. Med. Chem. Lett. 19, 706-709
46. Klasing, S. A., Mora, M. I., Wilson, W. C., Fahey, G. C., Jr., and Garst, J. E. (1985) Proc. Soc. Exp. Biol. Med. 179, 529-538
47. Deters, M., Knochenwefel, H., Lindhorst, D., Koal, T., Meyer, H. H., Hänsel, W., Resch, K., and Kaever, V. (2008) Pharm. Res. 25, 1822-1827
48. Bodell, W. J., Ye, Q., Pathak, D. N., and Pongracz, K. (1998) Carcinogenesis 19, 437-443
49. Thompson, D. C., Thompson, J. A., Sugumaran, M., and Moldéus, P. (1993) Chem. Biol. Interact. 86, 129-162
50. Thompson, D. C., Perera, K., Krol, E. S., and Bolton, J. L. (1995) Chem. Res. Toxicol. 8, 323-327
51. van der Woude, H., Alink, G. M., van Rossum, B. E., Walle, K., van Steeg, H., Walle, T., and Rietjens, I. M. (2005) Chem. Res. Toxicol. 18, 1907-1916
52. Haim, N., Nemec, J., Roman, J., and Sinha, B. K. (1987) Cancer Res. 47, 5835-5840
53. Peterson, D. M., and Fisher, J. (1986) Biochemistry 25, 4077-4084
54. Moore, H. W., Czerniak, R., and Hamdan, A. (1986) Drugs Exp Clin Res 12, 475-494
55. Fang, J., Lu, J., and Holmgren, A. (2005) J. Biol. Chem. 280, 25284-25290
56. Bernard, K., Wang, W., Narlawar, R., Schmidt, B., and Kirk, K. L. (2009) J. Biol. Chem. 284, 30754-30765