Inhibitory Effects of Metabolites of 5-Demethylnobiletin on Human Nonsmall Cell Lung Cancer Cells

Journal of Agricultural and Food Chemistry

Volumn 64, Issue 24, 2016, Pages 4943-4949

  Song, Mingyue ^a   Charoensinphon, Noppawat ^a   Wu, Xian ^a   Zheng, Jinkai ^a,c   Gao, Zili ^a   Xu, Fei ^a   Wang, Minqi ^a   Xiao, Hang ^a,b  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b HUNAN AGRICULTURAL UNIVERSITY   (China)

^c INSTITUTE OF PLANT PROTECTION   (China)

Author keywords

5 demethylnobiletin; chemoprevention; lung cancer cells; metabolites; nobiletin

Indexed keywords

BIOLOGICAL ORGANS; BIOMOLECULES; CELL DEATH; CELL PROLIFERATION; CELLS; CITRUS FRUITS; CYTOLOGY; DISEASES; METABOLITES;

5-DEMETHYLNOBILETIN; CHEMOPREVENTION; CHEMOPREVENTIVE EFFECTS; FLOW CYTOMETRY ANALYSIS; LUNG CANCER CELLS; NOBILETIN; NON SMALL CELL LUNG CANCER; PROLIFERATION AND APOPTOSIS;

CELL SIGNALING;

5-DEMETHYLNOBILETIN; FLAVONE DERIVATIVE; PLANT EXTRACT;

ANIMAL; APOPTOSIS; CELL CYCLE CHECKPOINT; CELL PROLIFERATION; CHEMISTRY; CITRUS; DRUG EFFECT; HUMAN; LUNG TUMOR; METABOLISM; MOUSE; NON SMALL CELL LUNG CANCER; PATHOPHYSIOLOGY; TUMOR CELL LINE;

ANIMALS; APOPTOSIS; CARCINOMA, NON-SMALL-CELL LUNG; CELL CYCLE CHECKPOINTS; CELL LINE, TUMOR; CELL PROLIFERATION; CITRUS; FLAVONES; HUMANS; LUNG NEOPLASMS; MICE; PLANT EXTRACTS;

EID: 84976320914     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.6b01367     Document Type: Article

References (36)

1. Amin, a. R. M. R.; Kucuk, O.; Khuri, F. R.; Shin, D. M. Perspectives for cancer prevention with natural compounds J. Clin. Oncol. 2009, 27, 2712-2725 10.1200/JCO.2008.20.6235
2. Li, S.; Pan, M.-H.; Lo, C.-Y.; Tan, D.; Wang, Y.; Shahidi, F.; Ho, C.-T. Chemistry and health effects of polymethoxyflavones and hydroxylated polymethoxyflavones J. Funct. Foods 2009, 1, 2-12 10.1016/j.jff.2008.09.003
3. Xiao, H.; Yang, C. S.; Li, S.; Jin, H.; Ho, C.-T.; Patel, T. Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel inhibit growth of human lung cancer cells by apoptosis Mol. Nutr. Food Res. 2009, 53, 398-406 10.1002/mnfr.200800057
4. Qiu, P.; Dong, P.; Guan, H.; Li, S.; Ho, C.-T.; Pan, M.-H.; McClements, D. J.; Xiao, H. Inhibitory effects of 5-hydroxy polymethoxyflavones on colon cancer cells Mol. Nutr. Food Res. 2010, 54 (S2) S244-S252 10.1002/mnfr.200900605
5. Chen, Y. K.; Wang, H. C.; Ho, C. T.; Chen, H. Y.; Li, S.; Chan, H. L.; Chung, T. W.; Tan, K. T.; Li, Y. R.; Lin, C. C. 5-Demethylnobiletin promotes the formation of polymerized tubulin, leads to G2/M phase arrest and induces autophagy via JNK activation in human lung cancer cells J. Nutr. Biochem. 2015, 26, 484-504 10.1016/j.jnutbio.2014.12.003
6. Yang, M.; Cheng, C.; Yang, J.; Guo, D. Metabolite profiling and characterization for medicinal herbal remedies Curr. Drug Metab. 2012, 13, 535-557 10.2174/1389200211209050535
7. Murakami, A.; Koshimizu, K.; Ohigashi, H.; Kuwahara, S.; Kuki, W.; Takahashi, Y.; Hosotani, K.; Kawahara, S.; Matsuoka, Y. Characteristic rat tissue accumulation of nobiletin, a chemopreventive polymethoxyflavonoid, in comparison with luteolin BioFactors 2002, 16, 73-82 10.1002/biof.5520160303
8. Yasuda, T.; Yoshimura, Y.; Yabuki, H.; Nakazawa, T.; Ohsawa, K.; Mimaki, Y.; Sashida, Y. Urinary metabolites of nobiletin orally administered to rats Chem. Pharm. Bull. 2003, 51, 1426-1428 10.1248/cpb.51.1426
9. Li, S.; Wang, Z.; Sang, S.; Huang, M. T.; Ho, C. T. Identification of nobiletin metabolites in mouse urine Mol. Nutr. Food Res. 2006, 50, 291-299 10.1002/mnfr.200500214
10. Cheng, Z.; Surichan, S.; Ruparelia, K.; Arroo, R.; Boarder, M. R. Tangeretin and its metabolite 4′-hydroxytetramethoxyflavone attenuate EGF-stimulated cell cycle progression in hepatocytes; Role of inhibition at the level of mTOR/p70S6K Br. J. Pharmacol. 2011, 162, 1781-1791 10.1111/j.1476-5381.2010.01185.x
11. Lai, C. S.; Li, S.; Chai, C. Y.; Lo, C. Y.; Dushenkov, S.; Ho, C. T.; Pan, M. H.; Wang, Y. J. Anti-inflammatory and antitumor promotional effects of a novel urinary metabolite, 3′,4′-didemethylnobiletin, derived from nobiletin Carcinogenesis 2008, 29, 2415-2424 10.1093/carcin/bgn222
12. Li, S.; Sang, S.; Pan, M. H.; Lai, C. S.; Lo, C. Y.; Yang, C. S.; Ho, C. T. Anti-inflammatory property of the urinary metabolites of nobiletin in mouse Bioorg. Med. Chem. Lett. 2007, 17, 5177-5181 10.1016/j.bmcl.2007.06.096
13. Lo, Y. H.; Pan, M. H.; Li, S.; Yen, J. H.; Kou, M. C.; Ho, C. T.; Wu, M. J. Nobiletin metabolite, 3′,4′-dihydroxy-5,6,7,8-tetramethoxyflavone, inhibits LDL oxidation and down-regulates scavenger receptor expression and activity in THP-1 cells Biochim. Biophys. Acta, Mol. Cell Biol. Lipids 2010, 1801, 114-126 10.1016/j.bbalip.2009.10.002
14. Zheng, J.; Song, M.; Dong, P.; Qiu, P.; Guo, S.; Zhong, Z.; Li, S.; Ho, C.-T.; Xiao, H. Identification of novel bioactive metabolites of 5-demethylnobiletin in mice Mol. Nutr. Food Res. 2013, 57, 1999-2007 10.1002/mnfr.201300211
15. Siegel, R.; Naishadham, D.; Jemal, A. Cancer statistics, 2013 Ca-Cancer J. Clin. 2013, 63, 11-30 10.3322/caac.21166
16. Charoensinphon, N.; Qiu, P. 5-Demethyltangeretin inhibits human nonsmall cell lung cancer cell growth by inducing G2/M cell cycle arrest and apoptosis Mol. Nutr. Food Res. 2013, 57, 2103-2111 10.1002/mnfr.201300136
17. Wu, X.; Song, M.; Wang, M.; Zheng, J.; Gao, Z.; Xu, F.; Zhang, G.; Xiao, H. Chemopreventive effects of nobiletin and its colonic metabolites on colon carcinogenesis Mol. Nutr. Food Res. 2015, 59, 2383-2394 10.1002/mnfr.201500378
18. Eramo, A.; Lotti, F.; Sette, G.; Pilozzi, E.; Biffoni, M.; Di Virgilio, A.; Conticello, C.; Ruco, L.; Peschle, C.; De Maria, R. Identification and expansion of the tumorigenic lung cancer stem cell population Cell Death Differ. 2008, 15, 504-514 10.1038/sj.cdd.4402283
19. Kim, J.; Jung, J.; Lee, S.-J.; Lee, J.-S.; Park, M.-J. Cancer stem-like cells persist in established cell lines through autocrine activation of EGFR signaling Oncol. Lett. 2011, 3, 607-612 10.3892/ol.2011.531
20. Visvader, J. E.; Lindeman, G. J. Cancer stem cells in solid tumours: accumulating evidence and unresolved questions Nat. Rev. Cancer 2008, 8, 755-768 10.1038/nrc2499
21. Clarke, M. F.; Fuller, M. Stem Cells and Cancer: Two Faces of Eve Cell 2006, 124, 1111-1115 10.1016/j.cell.2006.03.011
22. Ye, X.-Q.; Li, Q.; Wang, G.-H.; Sun, F.-F.; Huang, G.-J.; Bian, X.-W.; Yu, S.-C.; Qian, G.-S. Mitochondrial and energy metabolism-related properties as novel indicators of lung cancer stem cells Int. J. Cancer 2011, 129, 820-831 10.1002/ijc.25944
23. Eramo, A.; Lotti, F.; Sette, G.; Pilozzi, E.; Biffoni, M.; Di Virgilio, A.; Conticello, C.; Ruco, L.; Peschle, C.; De Maria, R. Identification and expansion of the tumorigenic lung cancer stem cell population Cell Death Differ. 2008, 15, 504-514 10.1038/sj.cdd.4402283
24. Qiu, P.; Guan, H.; Dong, P.; Guo, S.; Zheng, J.; Li, S.; Chen, Y.; Ho, C.-T.; Pan, M.-H.; McClements, D. J. et al. The inhibitory effects of 5-hydroxy-3,6,7,8,3′,4′-hexamethoxyflavone on human colon cancer cells Mol. Nutr. Food Res. 2011, 55, 1523-1532 10.1002/mnfr.201100070
25. Sergeev, I. N.; Ho, C.-T.; Li, S.; Colby, J.; Dushenkov, S. Apoptosis-inducing activity of hydroxylated polymethoxyflavones and polymethoxyflavones from orange peel in human breast cancer cells Mol. Nutr. Food Res. 2007, 51, 1478-1484 10.1002/mnfr.200700136
26. Eymin, B.; Gazzeri, S. Role of cell cycle regulators in lung carcinogenesis Cell Adh. Migr. 2010, 4, 114-123 10.4161/cam.4.1.10977
27. Malumbres, M.; Barbacid, M. Cell cycle, CDKs and cancer: a changing paradigm Nat. Rev. Cancer 2009, 9, 153-166 10.1038/nrc2602
28. Molinari, M. Cell cycle checkpoints and their inactivation in human cancer Cell Proliferation 2000, 33, 261-274 10.1046/j.1365-2184.2000.00191.x
29. Taylor, W. R.; Stark, G. R. Regulation of the G2/M transition by p53 Oncogene 2001, 20, 1803-1815 10.1038/sj.onc.1204252
30. Charrier-Savournin, F. B.; Château, M.-T.; Gire, V.; Sedivy, J.; Piette, J.; Dulic, V. p21-Mediated nuclear retention of cyclin B1-Cdk1 in response to genotoxic stress Mol. Biol. Cell 2004, 15, 3965-3976 10.1091/mbc.E03-12-0871
31. Taylor, W. R.; Schönthal, A. H.; Galante, J.; Stark, G. R. p130/E2F4 binds to and represses the cdc2 promoter in response to p53 J. Biol. Chem. 2001, 276, 1998-2006 10.1074/jbc.M005101200
32. Vousden, K. H. Functions of p53 in metabolism and invasion Biochem. Soc. Trans. 2009, 37, 511-517 10.1042/BST0370511
33. Taylor, W. R.; DePrimo, S. E.; Agarwal, A.; Agarwal, M. L.; Schönthal, A. H.; Katula, K. S.; Stark, G. R. Mechanisms of G2 arrest in response to overexpression of p53 Mol. Biol. Cell 1999, 10, 3607-3622 10.1091/mbc.10.11.3607
34. Azzam, E. I.; de Toledo, S. M.; Pykett, M. J.; Nagasawa, H.; Little, J. B. CDC2 is down-regulated by ionizing radiation in a p53-dependent manner Cell Growth Differ. 1997, 8, 1161-1169
35. Abbas, T.; Dutta, A. p21 in cancer: intricate networks and multiple activities Nat. Rev. Cancer 2009, 9, 400-414 10.1038/nrc2657
36. Qiu, P.; Guan, H.; Dong, P.; Li, S.; Ho, C. T.; Pan, M. H.; Mcclements, D. J.; Xiao, H. The p53-, Bax- and p21-dependent inhibition of colon cancer cell growth by 5-hydroxy polymethoxyflavones Mol. Nutr. Food Res. 2011, 55, 613-622 10.1002/mnfr.201000269