Effects of Stable Degradation Products of Curcumin on Cancer Cell Proliferation and Inflammation

Journal of Agricultural and Food Chemistry

Volumn 64, Issue 48, 2016, Pages 9189-9195

  Sanidad, Katherine Z ^a   Zhu, Julia ^a   Wang, Weicang ^a   Du, Zheyuan ^a   Zhang, Guodong ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

bicyclopentadione; cancer; curcumin; degradation; inflammation

Indexed keywords

CELL DEATH; CELL PROLIFERATION; CELLS; CYTOLOGY; DEGRADATION; DISEASES; PATHOLOGY; PH; PH EFFECTS;

ANTI-INFLAMMATORY EFFECTS; BICYCLOPENTADIONE; CANCER; CHEMICAL DEGRADATION; CURCUMIN; INFLAMMATION; INFLAMMATORY RESPONSE; RAW 264.7 MACROPHAGES;

CELL SIGNALING;

ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; CURCUMIN; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LIPOPOLYSACCHARIDE;

ANIMAL; APOPTOSIS; CELL CYCLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; DRUG EFFECTS; INFLAMMATION; MACROPHAGE; METABOLISM; MOUSE; RAW 264.7 CELL LINE; SIGNAL TRANSDUCTION; TUMOR CELL LINE;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; CURCUMIN; INFLAMMATION; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; MOLECULAR STRUCTURE; NF-KAPPA B; RAW 264.7 CELLS; SIGNAL TRANSDUCTION;

EID: 85002781285     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.6b04343     Document Type: Article

References (27)

1. Aggarwal, B. B.; Sundaram, C.; Malani, N.; Ichikawa, H. Curcumin: the Indian solid gold. In The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease; Aggarwal, B. B., Surh, Y.-J., Shishodia, S., Eds.; Springer: Boston, MA, USA, 2007; pp 1-75.
2. Bimonte, S.; Barbieri, A.; Palma, G.; Luciano, A.; Rea, D.; Arra, C. Curcumin inhibits tumor growth and angiogenesis in an orthotopic mouse model of human pancreatic cancer BioMed Res. Int. 2013, 2013, 810423 10.1155/2013/810423
3. Bimonte, S.; Barbieri, A.; Palma, G.; Rea, D.; Luciano, A.; D'Aiuto, M.; Arra, C.; Izzo, F. Dissecting the role of curcumin in tumour growth and angiogenesis in mouse model of human breast cancer BioMed Res. Int. 2015, 2015, 878134 10.1155/2015/878134
4. Yoysungnoen-Chintana, P.; Bhattarakosol, P.; Patumraj, S. Antitumor and antiangiogenic activities of curcumin in cervical cancer xenografts in nude mice BioMed Res. Int. 2014, 2014, 817972 10.1155/2014/817972
5. Rocks, N.; Bekaert, S.; Coia, I.; Paulissen, G.; Gueders, M.; Evrard, B.; Van Heugen, J. C.; Chiap, P.; Foidart, J. M.; Noel, A.; Cataldo, D. Curcumin-cyclodextrin complexes potentiate gemcitabine effects in an orthotopic mouse model of lung cancer Br. J. Cancer 2012, 107, 1083-1092 10.1038/bjc.2012.379
6. Perkins, S.; Verschoyle, R. D.; Hill, K.; Parveen, I.; Threadgill, M. D.; Sharma, R. A.; Williams, M. L.; Steward, W. P.; Gescher, A. J. Chemopreventive efficacy and pharmacokinetics of curcumin in the Min/+ mouse, a model of familial adenomatous polyposis Cancer Epidemiol. Biomarkers Prevention 2002, 11, 535-540
7. Carroll, R. E.; Benya, R. V.; Turgeon, D. K.; Vareed, S.; Neuman, M.; Rodriguez, L.; Kakarala, M.; Carpenter, P. M.; McLaren, C.; Meyskens, F. L., Jr.; Brenner, D. E. Phase IIa clinical trial of curcumin for the prevention of colorectal neoplasia Cancer Prev. Res. 2011, 4, 354-364 10.1158/1940-6207.CAPR-10-0098
8. Dhillon, N.; Aggarwal, B. B.; Newman, R. A.; Wolff, R. A.; Kunnumakkara, A. B.; Abbruzzese, J. L.; Ng, C. S.; Badmaev, V.; Kurzrock, R. Phase II trial of curcumin in patients with advanced pancreatic cancer Clin. Cancer Res. 2008, 14, 4491-4499 10.1158/1078-0432.CCR-08-0024
9. Gordon, O. N.; Luis, P. B.; Sintim, H. O.; Schneider, C. Unraveling curcumin degradation: autoxidation proceeds through spiroepoxide and vinylether intermediates enroute to the main bicyclopentadione J. Biol. Chem. 2015, 290, 4817-4828 10.1074/jbc.M114.618785
10. Griesser, M.; Pistis, V.; Suzuki, T.; Tejera, N.; Pratt, D. A.; Schneider, C. Autoxidative and cyclooxygenase-2 catalyzed transformation of the dietary chemopreventive agent curcumin J. Biol. Chem. 2011, 286, 1114-1124 10.1074/jbc.M110.178806
11. Wang, Y. J.; Pan, M. H.; Cheng, A. L.; Lin, L. I.; Ho, Y. S.; Hsieh, C. Y.; Lin, J. K. Stability of curcumin in buffer solutions and characterization of its degradation products J. Pharm. Biomed. Anal. 1997, 15, 1867-1876 10.1016/S0731-7085(96)02024-9
12. Schneider, C.; Gordon, O. N.; Edwards, R. L.; Luis, P. B. Degradation of curcumin: from mechanism to biological implications J. Agric. Food Chem. 2015, 63, 7606-7614 10.1021/acs.jafc.5b00244
13. Griesser, M.; Pistis, V.; Suzuki, T.; Tejera, N.; Pratt, D. A.; Schneider, C. Autoxidative and cyclooxygenase-2 catalyzed transformation of the dietary chemopreventive agent curcumin J. Biol. Chem. 2011, 286, 1114-1124 10.1074/jbc.M110.178806
14. Wang, Y. J.; Pan, M. H.; Cheng, A. L.; Lin, L. I.; Ho, Y. S.; Hsieh, C. Y.; Lin, J. K. Stability of curcumin in buffer solutions and characterization of its degradation products J. Pharm. Biomed. Anal. 1997, 15, 1867-1876 10.1016/S0731-7085(96)02024-9
15. Nimiya, Y.; Wang, W.; Du, Z.; Sukamtoh, E.; Zhu, J.; Decker, E.; Zhang, G. Redox modulation of curcumin stability: Redox active antioxidants increase chemical stability of curcumin Mol. Nutr. Food Res. 2016, 60, 487-494 10.1002/mnfr.201500681
16. Wichitnithad, W.; Nimmannit, U.; Wacharasindhu, S.; Rojsitthisak, P. Synthesis, characterization and biological evaluation of succinate prodrugs of curcuminoids for colon cancer treatment Molecules 2011, 16, 1888-1900 10.3390/molecules16021888
17. Gordon, O. N.; Luis, P. B.; Sintim, H. O.; Schneider, C. Unraveling curcumin degradation: autoxidation proceeds through spiroepoxide and vinylether intermediates en route to the main bicyclopentadione J. Biol. Chem. 2015, 290, 4817-4828 10.1074/jbc.M114.618785
18. Borsig, L.; Wong, R.; Hynes, R. O.; Varki, N. M.; Varki, A. Synergistic effects of L- and P-selectin in facilitating tumor metastasis can involve non-mucin ligands and implicate leukocytes as enhancers of metastasis Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 2193-2198 10.1073/pnas.261704098
19. Zhang, G.; Nitteranon, V.; Chan, L. Y.; Parkin, K. L. Glutathione conjugation attenuates biological activities of 6-dehydroshogaol from ginger Food Chem. 2013, 140, 1-8 10.1016/j.foodchem.2013.02.073
20. Shen, L.; Ji, H. F. The pharmacology of curcumin: is it the degradation products? Trends Mol. Med. 2012, 18, 138-144 10.1016/j.molmed.2012.01.004
21. Schneider, C.; Gordon, O. N.; Edwards, R. L.; Luis, P. B. Degradation of curcumin: from mechanism to biological implications J. Agric. Food Chem. 2015, 63, 7606-7614 10.1021/acs.jafc.5b00244
22. Deters, M.; Knochenwefel, H.; Lindhorst, D.; Koal, T.; Meyer, H. H.; Hansel, W.; Resch, K.; Kaever, V. Different curcuminoids inhibit T-lymphocyte proliferation independently of their radical scavenging activities Pharm. Res. 2008, 25, 1822-1827 10.1007/s11095-008-9579-2
23. Aggarwal, B. B.; Kumar, A.; Bharti, A. C. Anticancer potential of curcumin: preclinical and clinical studies Anticancer Res. 2003, 23, 363-398
24. Ketron, A. C.; Gordon, O. N.; Schneider, C.; Osheroff, N. Oxidative metabolites of curcumin poison human type II topoisomerases Biochemistry 2013, 52, 221-227 10.1021/bi3014455
25. Das, L.; Vinayak, M. Long-term effect of curcumin down-regulates expression of tumor necrosis factor-alpha and interleukin-6 via modulation of E26 transformation-specific protein and nuclear factor-kappaB transcription factors in livers of lymphoma bearing mice Leuk. Lymphoma 2014, 55, 2627-2636 10.3109/10428194.2014.889824
26. Das, L.; Vinayak, M. Long term effect of curcumin in regulation of glycolytic pathway and angiogenesis via modulation of stress activated genes in prevention of cancer PLoS One 2014, 9, e99583 10.1371/journal.pone.0099583
27. Das, L.; Vinayak, M. Long term effect of curcumin in restoration of tumour suppressor p53 and phase-II antioxidant enzymes via activation of Nrf2 signalling and modulation of inflammation in prevention of cancer PLoS One 2015, 10, e0124000 10.1371/journal.pone.0124000