Differential inhibition of human colon cancer cells by structurally similar flavonoids of citrus

Food Chemistry

Volumn 132, Issue 1, 2012, Pages 27-34

  Chidambara Murthy, K N ^a   Kim, Jinhee ^a   Vikram, Amit ^a   Patil, Bhimanagouda S ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

Apoptosis; Citrus; Flavonoids; Structure activity relation; SW480

Indexed keywords

CELL DEATH; CELL PROLIFERATION; DISEASES; GENES; TRANSCRIPTION;

ADENOCARCINOMA CELLS; ANTI-PROLIFERATIVE; ANTICANCER ACTIVITIES; APOPTOSIS INDUCTION; CASPASE-3; CITRUS; COLON CANCER; DOUBLE BONDS; HUMAN COLON CANCER CELLS; HYDROXYL GROUPS; PROLIFERATION INHIBITION; STRUCTURE ACTIVITY RELATION; STRUCTURE-ACTIVITY; STRUCTURE-FUNCTION RELATIONSHIP; SW480; UP-REGULATION;

FLAVONOIDS;

APIGENIN; AURANTIIN; CASPASE 3; CENTAUREIDIN; HESPERIDIN; KAEMPFEROL; NARINGENIN; PROTEIN BAX; PROTEIN BCL 2; QUERCETIN; RUTOSIDE; FLAVONOID; PLANT EXTRACT;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL; CANCER INHIBITION; CELL DEATH; CELL GROWTH; CELL PROLIFERATION; CHEMICAL STRUCTURE; CITRUS FRUIT; COLON ADENOCARCINOMA; ENZYME ACTIVATION; GENE EXPRESSION; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IMMUNOBLOTTING; MUTATION; POLYMERASE CHAIN REACTION; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION; UPREGULATION; CHEMISTRY; CITRUS; COLON TUMOR; DRUG EFFECTS; GENETICS; METABOLISM;

CITRUS;

APOPTOSIS; CELL PROLIFERATION; CITRUS; COLONIC NEOPLASMS; FLAVONOIDS; HUMANS; MOLECULAR STRUCTURE; PLANT EXTRACTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84355166552     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2011.10.014     Document Type: Article

References (48)

1. A. Arora, M.G. Nair, and G.M. Strasburg Structure-activity relationships for antioxidant activities of a series of flavonoids in a liposomal system Free Radical Biology & Medicine 24 9 1998 1355 1363 (Pubitemid 28270336)
2. D. Birt, S. Hendrich, and W. Wang Dietary agents in cancer prevention: flavonoids and isoflavonoids Pharmacology & Therapeutics 90 2-3 2001 157 177 (Pubitemid 32913477)
3. G. Cao, E. Sofic, and R.L. Prior Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships Free Radical Biology & Medicine 22 5 1997 749 760 (Pubitemid 27058337)
4. O.K. Chun, S.J. Chung, and W.O. Song Estimated dietary flavonoid intake and major food sources of US adults Journal of Nutrition 137 5 2007 1244 1252 (Pubitemid 46701918)
5. B. D'Autreaux, and M.B. Toledano ROS as signalling molecules: mechanisms that generate specificity in ROS homeostasis Nature Reviews Molecular Cell Biology 8 10 2007 813 824 (Pubitemid 47462134)
6. N.N. Danial, and S.J. Korsmeyer Cell death: Critical control points Cell 116 2 2004 205 219 (Pubitemid 38167313)
7. N.S. Elsisi, S. Darling-Reed, E.Y. Lee, E.T. Oriaku, and K.F. Soliman Ibuprofen and apigenin induce apoptosis and cell cycle arrest in activated microglia Neuroscience Letters 375 2 2005 91 96
8. J. Ferte, J.-M. Kuhnel, G. Chapuis, Y. Rolland, G. Lewin, and M.A. Schwaller Flavonoid-related modulators of multidrug resistance. Synthesis, pharmacological activity, and structure-activity relationships Journal of Medicinal Chemistry 42 3 1999 478 489 (Pubitemid 29085108)
9. T. Fotsis, M.S. Pepper, E. Aktas, S. Breit, S. Rasku, and H. Adlercreutz Flavonoids, dietary-derived inhibitors of cell proliferation and in vitro angiogenesis Cancer Research 57 14 1997 2916 2921 (Pubitemid 27315039)
10. H.R. Frydoonfar, D.R. McGrath, and A.D. Spigelman The variable effect on proliferation of a colon cancer cell line by the citrus fruit flavonoid Naringenin Colorectal Disease 5 2003 149 152 (Pubitemid 36442837)
11. K. Gao, S.M. Henning, Y. Niu, A.A. Youssefian, N.P. Seeram, and A. Xu The citrus flavonoid naringenin stimulates DNA repair in prostate cancer cells The Journal of Nutritional Biochemistry 17 2 2006 89 95 (Pubitemid 43082142)
12. G. Häcker The morphology of apoptosis Cell and Tissue Research 301 1 2000 5 17 (Pubitemid 30459851)
13. M.G. Hertog, D. Kromhout, C. Aravanis, H. Blackburn, R. Buzina, and F. Fidanza Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study Archives of Internal Medicine 155 4 1995 381 386
14. M.G.L. Hertog, E.J.M. Feskens, D. Kromhout, P.C.H. Hollman, and M.B. Katan Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study The Lancet 342 8878 1993 1007 1011 (Pubitemid 23314801)
15. R. Horowitz, and B. Gentili Flavonoid constituents of citrus Citrus Science and Technology 1 1977 397 426
16. D. Ichimatsu, M. Nomura, S. Nakamura, S. Moritani, K. Yokogawa, and S. Kobayashi Structure-activity relationship of flavonoids for inhibition of epidermal growth factor-induced transformation of JB6 CI 41 cells Molecular Carcinogenesis 46 2007 436 445 (Pubitemid 46897048)
17. N.J. Kang, S.H. Shin, H.J. Lee, and K.W. Lee Polyphenols as small molecular inhibitors of signaling cascades in carcinogenesis Pharmacology & Therapeutics 2011
18. S.-I. Kanno, A. Tomizawa, T. Hiura, Y. Osanai, A. Shouji, and M. Ujibe Inhibitory effects of naringenin on tumor growth in human cancer cell lines and sarcoma S-180-implanted mice Biological & Pharmaceutical Bulletin 28 3 2005 527 530 (Pubitemid 40879982)
19. P. Kaur, S. Shukla, and S. Gupta Plant flavonoid apigenin inactivates Akt to trigger apoptosis in human prostate cancer: an in vitro and in vivo study Carcinogenesis 29 11 2008 2210 2217
20. S. Kawaii, Y. Tomono, E. Katase, K. Ogawa, and M. Yano Antiproliferative activity of flavonoids on several cancer cell lines Bioscience, Biotechnology and Biochemistry 63 5 1999 896 899 (Pubitemid 129562768)
21. P. Knekt, J. Kumpulainen, R. Jarvinen, H. Rissanen, M. Heliovaara, and A. Reunanen Flavonoid intake and risk of chronic diseases American Journal of Clinical Nutrition 76 3 2002 560 568 (Pubitemid 34920833)
22. S. Kuntz, U. Wenzel, and H. Daniel Comparative analysis of the effects of flavonoids on proliferation, cytotoxicity, and apoptosis in human colon cancer cell lines European Journal of Nutrition 38 3 1999 133 142 (Pubitemid 29352529)
23. S.-M. Kuo Antiproliferative potency of structurally distinct dietary flavonoids on human colon cancer cells Cancer Letters 110 1-2 1996 41 48 (Pubitemid 27042919)
24. K.R. Landis Piwowar, V. Milacic, and Q.P. Dou Relationship between the methylation status of dietary flavonoids and their growth inhibitory and apoptosis inducing activities in human cancer cells Journal of Cellular Biochemistry 105 2 2008 514 523
25. L. Le Marchand Cancer preventive effects of flavonoids-a review Biomedecine & Pharmacotherapy 56 6 2002 296 301 (Pubitemid 35245313)
26. T. Leonardi, J. Vanamala, S. Taddeo, L. Davidson, M. Murphy, and B. Patil Apigenin and naringenin suppress colon carcinogenesis through the aberrant crypt stage in azoxymethane-treated rats Experimental Biology and Medicine 235 6 2010 710 717
27. T.J. Mackeya, A. Borkowskib, P. Aminc, S.C. Jacobsa, and N. Kyprianoua Bcl2/Bax ratio as a predictive marker for therapeutic response to radiotherapy in patients with prostate cancer Urology 52 6 1998 1085 1090
28. D.D. Majo, M. Giammanco, M.L. Guardia, E. Tripoli, S. Giammanco, and E. Finotti Flavanones in citrus fruit: Structure-antioxidant activity relationships Food Research International 38 10 2005 1161 1166 (Pubitemid 41097556)
29. C. Manach, F. Regerat, O. Texier, G. Agullo, C. Demigne, and C. Remesy Bioavailability, metabolism and physiological impact of 4-oxo-flavonoids Nutrition Research 16 3 1996 517 544 (Pubitemid 26084096)
30. J.A. Manthey, N. Guthrie, and K. Grohmann Biological properties of citrus flavonoids pertaining to cancer and inflammation Current Medicinal Chemistry 8 2001 135 153 (Pubitemid 32421562)
31. T.T.T. Nguyen, E. Tran, T.H. Nguyen, P.T. Do, T.H. Huynh, and H. Huynh The role of activated MEK-ERK pathway in quercetin-induced growth inhibition and apoptosis in A549 lung cancer cells Carcinogenesis 25 5 2004 647 659 (Pubitemid 38618516)
32. H. Park, M.J. Kim, E. Ha, and J.H. Chung Apoptotic effect of hesperidin through caspase3 activation in human colon cancer cells, SNU-C4 Phytomedicine 15 1-2 2008 147 151 (Pubitemid 350297903)
33. J. Peterson, and J. Dwyer Flavonoids: Dietary occurrence and biochemical activity Nutrition Research 18 12 1998 1995 2018 (Pubitemid 28543827)
34. C. Pouget, F. Lauthier, A. Simon, C. Fagnere, J.-P. Basly, and C. Delage Flavonoids: structural requirements for antiproliferative activity on breast cancer cells Bioorganic & Medicinal Chemistry Letters 11 24 2001 3095 3097 (Pubitemid 33092000)
35. C. Pouget, F. Lauthier, A. Simon, C. Fagnere, J.-P. Basly, and C. Delage Flavonoids: structural requirements for antiproliferative activity on breast cancer cells Bioorganic & Medicinal Chemistry Letters 11 24 2001 3095 3097 (Pubitemid 33092000)
36. F.O. Ranelletti, R. Ricci, L.M. Larocca, N. Maggiano, A. Capelli, and G. Scambia Growth inhibitory effect of quercetin and presence of type II estrogen binding sites in human colon cancer cell lines and primary colorectal tumors International Journal of Cancer 50 3 1992 486 492
37. C.A. Rice-Evans, N.J. Miller, and G. Paganga Structure-antioxidant activity relationships of flavonoids and phenolic acids Free Radical Biology & Medicine 20 7 1996 933 956 (Pubitemid 26157509)
38. S. Rozen, and H.J. Skaletsky Primer3 on the WWW for general users and for biologist programmers S. Krawetz, S. Misener, Bioinformatics methods and protocols: Methods in molecular biology 2000 Humana Press Totowa, NJ 365 386
39. O. Sabek, M. Tevfik Dorak, Malak Kotb, A. Osama Gaber, and Lillian Gaber Quantitative detection of T-cell activation markers by real-time PCR in renal transplant rejection and correlation with histopathologic evaluation Transplantation 74 5 2002 701 707
40. M. Sebbagh, C. Renvoizé, J. Hamelin, N. Riché, J. Bertoglio, and J. Bréard Caspase-3-mediated cleavage of ROCK I induces MLC phosphorylation and apoptotic membrane blebbing Nature Cell Biology 3 2001 346 352 (Pubitemid 32288441)
41. A. Seyoum, K. Asres, and F.K. El-Fiky Structure-radical scavenging activity relationships of flavonoids Phytochemistry 67 18 2006 2058 2070 (Pubitemid 44301284)
42. T. Takahashi, M. Kobori, H. Shinmoto, and T. Tsushida Structure-activity relationships of flavonoids and the induction of granulocytic-or monocytic-differentiation in HL60 human myeloid leukemia cells Bioscience, Biotechnology, and Biochemistry 62 11 1998 2199 2204 (Pubitemid 128473795)
43. T. Tanaka, H. Makita, K. Kawabata, H. Mori, M. Kakumoto, and K. Satoh Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally occurring flavonoids, diosmin and hesperidin Carcinogenesis 18 5 1997 957 965 (Pubitemid 28132340)
44. C. Tsimplouli, C. Demetzos, M. Hadzopoulou-Cladaras, P. Pantazis, and K. Dimas In vitro activity of dietary flavonol congeners against human cancer cell lines European Journal of Nutrition 1 2011 1 10
45. J. Vanamala, T. Leonardi, B.S. Patil, S.S. Taddeo, M.E. Murphy, and L.M. Pike Suppression of colon carcinogenesis by bioactive compounds in grapefruit Carcinogenesis 27 6 2006 1257 1265 (Pubitemid 43994864)
46. F. Virgili, F. Acconcia, R. Ambra, A. Rinna, P. Totta, and M. Marino Nutritional flavonoids modulate estrogen receptor α signaling IUBMB Life 56 3 2004 145 151 (Pubitemid 38678570)
47. N. Xing, Y. Chen, S.H. Mitchell, and C.Y.F. Young Quercetin inhibits the expression and function of the androgen receptor in LNCaP prostate cancer cells Carcinogenesis 22 3 2001 409 414 (Pubitemid 32203819)
48. T. Yoshida, M. Konishi, M. Horinaka, T. Yasuda, A.E. Goda, and H. Taniguchi Kaempferol sensitizes colon cancer cells to TRAIL-induced apoptosis Biochemical and Biophysical Research Communications 375 1 2008 129 133