Regulation of apoptosis by modified naringenin derivatives in human colorectal carcinoma RKO cells

Journal of Cellular Biochemistry

Volumn 104, Issue 1, 2008, Pages 259-273

  Lee, Eung Ryoung ^a   Kang, Yong Jin ^a   Kim, Hyun Jeong ^a   Choi, Hye Yeon ^a   Kang, Geun Ho ^a   Kim, Jung Hyun ^a   Kim, Bong Woo ^a   Jeong, Hyo Soon ^a   Park, Yong Sun ^a   Cho, Ssang Goo ^a  

^a Konkuk University   (South Korea)

Author keywords

Apoptosis; ERK; Flavonoid; Modified naringenin derivatives; Naringenin; ROS

Indexed keywords

3 HYDROXYFLAVONE; 3,2' DIHYDROXYFLAVONE; 3,3' DIHYDROXYFLAVONE; 3,4' DIHYDROXYFLAVONE; 4' HYDROXY 5 METHOXYFLAVONE; 4' HYDROXY 6 METHOXYFLAVONE; 4' HYDROXY 7 METHOXYFLAVONE; 4' HYDROXYFLAVONE; 4',6 DIHYDROXYFLAVONE; 5,2,3',4',5' PENTAHYDROXYFLAVONE; 5,7 DIHYDROXY 3',4',5' TRIMETHOXYFLAVONE; 5,7,3' TRIHYDROXY 4' METHOXYFLAVONE; 5,7,4' TRIHYDROXYFLAVANON; 7 O (2 NAPHTYLMETHYL)NARINGENIN; 7 O (3 IODOBENZYL)NARINGENIN; 7 O (3 METHOXYBENZYL)NARINGENIN; 7 O (4 FLUOROBENZYL)NARINGENIN; 7 O (METHOXYGLYCYL DEXTRO PROLINE CARBONYLMETHYL)NARINGENIN; 7 O (METHOXYLEUCYL DEXTRO PROLINE CARBONYLMETHYL)NARINGENIN; 7 O BENZOXYCARBONYLMETHYLNARINGENIN; 7 O BENZYLNARINGENIN; 7,8,4' TRIHYDROXYFLAVONE; ANTINEOPLASTIC AGENT; BENZYLOXYCARBONYLISOLEUCYLMETHOXYGLUTAMYLTHREONYLMETHOXYASPARTIC ACID; ETOPOSIDE; N ACETYLASPARTYLGLUTAMYLVALYLASPARTYLCHOLINE; NARINGENIN; NARINGENIN DERIVATIVE; PEPTIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; FLAVANONE DERIVATIVE; FLAVONOID; MITOGEN ACTIVATED PROTEIN KINASE; REACTIVE OXYGEN METABOLITE;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER CELL DESTRUCTION; CARCINOMA CELL; CELL PROLIFERATION; CELL VIABILITY; COLORECTAL CARCINOMA; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; ENZYME ACTIVATION; HUMAN; HUMAN CELL; HYDROXYLATION; IN VITRO STUDY; MITOCHONDRIAL MEMBRANE POTENTIAL; PRIORITY JOURNAL; REGULATORY MECHANISM; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; CHEMISTRY; COLORECTAL TUMOR; PATHOLOGY; TUMOR CELL LINE;

APOPTOSIS; CELL LINE, TUMOR; COLORECTAL NEOPLASMS; EXTRACELLULAR SIGNAL-REGULATED MAP KINASES; FLAVANONES; FLAVONOIDS; HUMANS; HYDROXYLATION; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 46449087996     PISSN: 07302312     EISSN: 10974644     Source Type: Journal    
DOI: 10.1002/jcb.21622     Document Type: Article

References (44)

1. Beard SE, Capaldi SR, Gee P. 1996. Stress responses to DNA damaging agents in the human colon carcinoma cell line, RKO. Mutat Res 371:1-13.
2. Birt DF, Hendrich S, Wang W. 2001. Dietary agents in cancer prevention: Flavonoids and isoflavonoids. Pharmacol Ther 90:157-177.
3. Bors W, Michel C, Stettmaier K. 1997. Antioxidant effects of flavonoids. Biofactors 6:399-402.
4. Bugianesi R, Salucci M, Leonardi C, Ferracane R, Catasta G, Azzini E, Maiani G. 2004. Effect of domestic cooking on human bioavailability of naringenin, chlorogenic acid, lycopene and beta-carotene in cherry tomatoes. Eur J Nutr 43:360-366.
5. Chen Y, Yang L, Lee TJ. 2000. Oroxylin A inhibition of lipopolysaccharide-induced iNOS and COX-2 gene expression via suppression of nuclear factor-kappaB activation. Biochem Pharmacol 59:1445-1457.
6. Chen YC, Shen SC, Lee WR, Hou WC, Yang LL, Lee TJ. 2001. Inhibition of nitric oxide synthase inhibitors and lipopolysaccharide induced inducible NOS and cyclooxygenase-2 gene expressions by rutin, quercetin, and quercetin pentaacetate in RAW 264.7 macrophages. J Cell Biochem 82:537-548.
7. Chen YC, Shen SC, Lee WR, Hsu FL, Lin HY, Ko CH, Tseng SW. 2002. Emodin induces apoptosis in human promyeloleukemic HL-60 cells accompanied by activation of caspase 3 cascade but independent of reactive oxygen species production. Biochem Pharmacol 64:1713-1724.
8. Chen YC, Shen SC, Lin HY. 2003. Rutinoside at C7 attenuates the apoptosis-inducing activity of flavonoids. Biochem Pharmacol 66:1139-1150.
9. Cho SG, Kim JW, Lee YH, Hwang HS, Kim MS, Ryoo K, Kim MJ, Noh KT, Kim EK, Cho JH, Yoon KW, Cho EG, Park HS, Chi SW, Lee MJ, Kang SS, Ichijo H, Choi EJ. 2003. Identification of a novel antiapoptotic protein that antagonizes ASK1 and CAD activities. J Cell Biol 163:71-81.
10. Constantinou AI, Kamath N, Murley JS. 1998. Genistein inactivates bcl-2, delays the G2/M phase of the cell cycle, and induces apoptosis of human breast adenocarcinoma MCF-7 cells. Eur J Cancer 34:1927-1934.
11. Depeint F, Gee JM, Williamson G, Johnson IT. 2002. Evidence for consistent patterns between flavonoid structures and cellular activities. Proc Nutr Soc 61:97-103.
12. Frydoonfar HR, McGrath DR, Spigelman AD. 2003. The variable effect on proliferation of a colon cancer cell line by the citrus fruit flavonoid Naringenin. Colorectal Dis 5:149-152.
13. Goel A, Fuerst F, Hotchkiss E, Boland CR. 2006. Selenomethionine induces p53 mediated cell cycle arrest and apoptosis in human colon cancer cells. Cancer Biol Ther 5:529-535.
14. Hanahan D, Weinberg RA. 2000. The hallmarks of cancer. Cell 100:57-70.
15. Heijnen CG, Haenen GR, Oostveen RM, Stalpers EM, Bast A. 2002. Protection of flavonoids against lipid peroxidation: The structure activity relationship revisited. Free Radic Res 36:575-581.
16. Howe HL,Wu X, Ries LA, Cokkinides V, Ahmed F, Jemal A, Miller B, Williams M, Ward E, Wingo PA, Ramirez A, Edwards BK. 2006. Annual report to the nation on the status of cancer, 1975-2003, featuring cancer among U.S. Hispanic/Latino populations. Cancer 107:1711-1742.
17. Jemal A, Thomas A, Murray T, Thun M. 2002. Cancer statistics, 2002. CA Cancer J Clin 52:23-47.
18. Jemal A, Murray T, Samuels A, Ghafoor A, Ward E, Thun MJ. 2003. Cancer statistics, 2003. CA Cancer J Clin 53:5-26.
19. Kanadaswami C, Lee LT, Lee PP, Hwang JJ, Ke FC, Huang YT, Lee MT. 2005. The antitumor activities of flavonoids. In Vivo 19:895-909.
20. Kawaii S, Tomono Y, Katase E, Ogawa K, Yano M. 1999a. Antiproliferative activity of flavonoids on several cancer cell lines. Biosci Biotechnol Biochem 63:896-899.
21. Kawaii S, Tomono Y, Katase E, Ogawa K, Yano M. 1999b. Quantitation of flavonoid constituents in citrus fruits. J Agric Food Chem 47:3565-3571.
22. Keinan-Boker L, van Der Schouw YT, Grobbee DE, Peeters PH. 2004. Dietary phytoestrogens and breast cancer risk. Am J Clin Nutr 79:282-288.
23. Ko CH, Shen SC, Lin HY, Hou WC, Lee WR, Yang LL, Chen YC. 2002. Flavanones structure-related inhibition on TPA-induced tumor promotion through suppression of extracellular signal-regulated protein kinases: Involvement of prostaglandin E2 in anti-promotive process. J Cell Physiol 193:93-102.
24. Kris-Etherton PM, Hecker KD, Bonanome A, Coval SM, Binkoski AE, Hilpert KF, Griel AE, Etherton TD. 2002. Bioactive compounds in foods: Their role in the prevention of cardiovascular disease and cancer. Am J Med 113 (Suppl 9B):71S-88S.
25. Kuo HM, Chang LS, Lin YL, Lu HF, Yang JS, Lee JH, Chung JG. 2007. Morin inhibits the growth of human leukemia HL-60 cells via cell cycle arrest and induction of apoptosis through mitochondria dependent pathway. Anticancer Res 27:395-405.
26. Le SB, Holmuhamedov EL, Narayanan VL, Sausville EA, Kaufmann SH. 2006. Adaphostin and other anticancer drugs quench the fluorescence of mitochondrial potential probes. Cell Death Differ 13:151-159.
27. Lee ER, Kang YJ, Kim JH, Lee HT, Cho SG. 2005. Modulation of apoptosis in HaCaT keratinocytes via differential regulation of ERK signaling pathway by flavonoids. J Biol Chem 280:31498-31507.
28. Lee ER, Kim JY, Kang YJ, Ahn JY, Kim JH, Kim BW, Choi HY, Jeong MY, Cho SG. 2006. Interplay between PI3K/Akt and MAPK signaling pathways in DNA-damaging drug-induced apoptosis. Biochim Biophys Acta 1763: 958-968.
29. Lee ER, Kim JH, Kang YJ, Cho SG. 2007. The antiapoptotic and anti-oxidant effect of eriodictyol on UV-induced apoptosis in keratinocytes. Biol Pharm Bull 30:32-37.
30. Li LY, Luo X, Wang X. 2001. Endonuclease G is an apoptotic DNase when released from mitochondria. Nature 412:95-99.
31. Lin JK, Chen YC, Huang YT, Lin-Shiau SY. 1997. Suppression of protein kinase C and nuclear oncogene expression as possible molecular mechanisms of cancer chemoprevention by apigenin and curcumin. J Cell Biochem Suppl 28-29:39-48.
32. Planey SL, Abrams MT, Robertson NM, Litwack G. 2003. Role of apical caspases and glucocorticoid-regulated genes in glucocorticoid-induced apoptosis of pre-B leukemic cells. Cancer Res 63:172-178.
33. Rice-Evans CA, Miller NJ, Paganga G. 1996. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20:933-956.
34. 2 in cultured endothelial cells. Arch Biochem Biophys 302:348-355.
35. Ryoo K, Huh SH, Lee YH, Yoon KW, Cho SG, Choi EJ. 2004. Negative regulation of MEKK1-induced signaling by glutathione S-transferase Mu. J Biol Chem 279:43589-43594.
36. Schroeter H, Spencer JP, Rice-Evans C, Williams RJ. 2001. Flavonoids protect neurons from oxidized low-density-lipoprotein-induced apoptosis involving c-Jun N-terminal kinase (JNK), c-Jun and caspase-3. Biochem J 358:547-557.
37. Sergeev IN, Li S, Colby J, Ho CT, Dushenkov S. 2006. Polymethoxylated flavones induce Ca(2+)-mediated apoptosis in breast cancer cells. Life Sci 80:245-253.
38. Spencer JP, Schroeter H, Crossthwaithe AJ, Kuhnle G, Williams RJ, Rice-Evans C. 2001. Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts. Free Radic Biol Med 31:1139-1146.
39. Spencer JP, Rice-Evans C, Williams RJ. 2003. Modulation of pro-survival Akt/protein kinase B and ERK1/2 signaling cascades by quercetin and its in vivo metabolites underlie their action on neuronal viability. J Biol Chem 278:34783-34793.
40. Studzinski GP, Harrison LE. 1999. Differentiation-related changes in the cell cycle traverse. Int Rev Cytol 189:1-58.
41. Verhoeyen ME, Bovy A, Collins G, Muir S, Robinson S, de Vos CH, Colliver S. 2002. Increasing antioxidant levels in tomatoes through modification of the flavonoid biosynthetic pathway. J Exp Bot 53:2099-2106.
42. Virgili F, Acconcia F, Ambra R, Rinna A, Totta P, Marino M. 2004. Nutritional flavonoids modulate estrogen receptor alpha signaling. IUBMB Life 56:145-151.
43. Williams RJ, Spencer JP, Rice-Evans C. 2004. Flavonoids: Antioxidants or signalling molecules? Free Radic Biol Med 36:838-849.
44. Zhang W, He Q, Chan LL, Zhou F, El Naghy M, Thompson EB, Ansari NH. 2001. Involvement of caspases in 4-hydroxy-alkenal-induced apoptosis in human leukemic cells. Free Radic Biol Med 30:699-706.