Hydroxylation at C4′ or C6 is essential for apoptosis-inducing activity of flavanone through activation of the caspase-3 cascade and production of reactive oxygen species

Free Radical Biology and Medicine

Volumn 36, Issue 7, 2004, Pages 897-910

  Ko, Ching Huai ^a   Shen, Shing Chuan ^b,c   Chen, Yen Chou ^a  

^a TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^b TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^c TAIPEI MEDICAL UNIVERSITY   (Taiwan)

Author keywords

4 OH flavanone; 6 OH flavanone; Ac DEVD FMK; Ac IETD FMK; Ac LEHD FMK; Acetyl Asp Glu Val Asp fluoromethylketone; Acetyl Ile Glu Thr Asp fluoromethylketone; Apoptosis; Caspase 3; Free radicals; Reactive oxygen species

Indexed keywords

4' HYDROXYFLAVANONE; 4' METHOXYFLAVANONE; 6 HYDROXYFLAVANONE; 6 METHOXYFLAVANONE; 7 HYDROXYFLAVANONE; 7 METHOXYFLAVANONE; ACETYLASPARTYLGLUTAMYLVALYLASPARTYL FLUOROMETHYL KETONE; ACETYLCYSTEINE; ACETYLISOLEUCYLGLUTAMYLTHREONYLASPARTYL FLUOROMETHYL KETONE; ACETYLLEUCYLGLUTAMYLHISTIDYLASPARTYL FLUOROMETHYL KETONE; ACETYLTYROSYLVALYLALANYLASPARTYL FLUOROMETHYL KETONE; ALLOPURINOL; ANTIOXIDANT; CASPASE 1 INHIBITOR; CASPASE 3; CASPASE 3 INHIBITOR; CASPASE 8; CASPASE 8 INHIBITOR; CASPASE 9; CASPASE INHIBITOR; CATALASE; CYTOCHROME C; FLAVANONE; FLAVANONE DERIVATIVE; HYDROXYL GROUP; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; PYRROLIDINE DITHIOCARBAMATE; REACTIVE OXYGEN METABOLITE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG; UNINDEXED DRUG; BAD PROTEIN, HUMAN; BAX PROTEIN, HUMAN; BCL2L1 PROTEIN, HUMAN; CARRIER PROTEIN; CASP3 PROTEIN, HUMAN; CASPASE; DNA FRAGMENT; GUANINE NUCLEOTIDE DISSOCIATION INHIBITOR; MCL1 PROTEIN; PROTEIN BAD; PROTEIN BAX; PROTEIN BCL 2; PROTEIN BCL X; RHO GUANINE NUCLEOTIDE DISSOCIATION INHIBITORS; TUMOR PROTEIN;

APOPTOSIS; ARTICLE; ASSAY; CELL DEATH; CONTROLLED STUDY; CYTOPATHOGENIC EFFECT; CYTOSOL; DIPLOIDY; DRUG CYTOTOXICITY; DRUG HYDROXYLATION; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INDUCTION; ENZYME INHIBITION; ENZYME RELEASE; HUMAN; HUMAN CELL; LEUKEMIA CELL; LEUKEMIA CELL LINE; MONOCYTE; NEUTROPHIL; PRIORITY JOURNAL; PROTEIN DEGRADATION; STRUCTURE ACTIVITY RELATION; CELL STRAIN HL 60; CHEMISTRY; FLOW CYTOMETRY; HYDROXYLATION; MALE; METABOLISM; PHYSIOLOGY; PROTO ONCOGENE;

FELIS CATUS;

ACETYLCYSTEINE; ALLOPURINOL; ANTIOXIDANTS; APOPTOSIS; BCL-2-ASSOCIATED X PROTEIN; BCL-ASSOCIATED DEATH PROTEIN; BCL-X PROTEIN; CARRIER PROTEINS; CASPASE 3; CASPASES; CATALASE; CYTOCHROMES C; DNA FRAGMENTATION; FLAVANONES; FLOW CYTOMETRY; GENES, BCL-2; GUANINE NUCLEOTIDE DISSOCIATION INHIBITORS; HL-60 CELLS; HUMANS; HYDROXYLATION; MALE; NEOPLASM PROTEINS; POLY(ADP-RIBOSE) POLYMERASES; PROTO-ONCOGENE PROTEINS C-BCL-2; REACTIVE OXYGEN SPECIES; SUPEROXIDE DISMUTASE;

EID: 1542395634     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2003.12.020     Document Type: Article

References (45)

1. Middleton E. Jr., Kandaswami C., Theoharides T.C. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 52:2000;673-751.
2. Pietta P.G. Flavonoids as antioxidants. J. Nat. Prod. 63:2000;1035-1042.
3. Chen Y.C., Shen S.C., Chen L.G., Lee T.J.-F., Yang L.L. Wogonin, baicalin and baicalein inhibition of inducible nitric oxide synthase and cyclooxygenase gene expression induced by NOS inhibitors and lipopolysaccharide. Biochem. Pharmacol. 61:2001;1417-1427.
4. Kim H.K., Cheon B.S., Kim Y.H., Kim S.Y., Kim H.P. Effects of naturally occurring flavonoids on nitric oxide production in the macrophage cell line RAW 264.7 and their structure-activity relationships. Biochem. Pharmacol. 58:1999;759-765.
5. Wang H., Joseph J.A. Structure-activity relationships of quercetin in antagonizing hydrogen peroxide-induced calcium dysregulation in PC12 cells. Free Radic. Biol. Med. 27:1999;683-694.
6. Schroeter H., Williams R.J., Matin R., Iversen L., Rice-Evans C.A. Phenolic antioxidants attenuate neuronal cell death following uptake of oxidized low-density lipoprotein. Free Radic. Biol. Med. 29:2000;1222-1233.
7. Sekher Pannala A., Chan T.S., O'Brien P.J., Rice-Evans C.A. Flavonoid B-ring chemistry and antioxidant activity: fast reaction kinetics. Biochem. Biophys. Res. Commun. 282:2001;1161-1168.
8. Nicholson D.W. From bench to clinic with apoptosis-based therapeutic agents. Nature. 407:2000;810-816.
9. Jacks T., Weinberg R.A. Taking the study of cancer cell survival to a new dimension. Cell. 111:2002;923-925.
10. Hanahan D., Weinberg R.A. The hallmarks of cancer. Cell. 100:2000;57-70.
11. Li L.Y., Luo X., Wang X. Endonuclease G is an apoptotic DNase when released from mitochondria. Nature. 412:2001;95-99.
12. Chen Y.C., Shen S.C., Lee W.R., Lin H.Y., Ko C.H., Shih C.M., Yang L.L. Wogonin and fisetin induction of apoptosis through activation of caspase 3 cascade and alternative expression of p21 protein in hepatocellular carcinoma cells SK-HEP-1. Arch. Toxicol. 76:2002;351-359.
13. Wenzel U., Kuntz S., Brendel M.D., Daniel H. Dietary flavone is a potent apoptosis inducer in human colon carcinoma cells. Cancer Res. 60:2000;3823-3831.
14. 2+-induced oxidative stress in cultured retinal cells. Biochem. Pharmacol. 62:2001;111-118.
15. 2+-dependent endonuclease. Biochem. Pharmacol. 63:2002;225-236.
16. Pias E.K., Aw T.Y. Early redox imbalance mediates hydroperoxide-induced apoptosis in mitotic competent undifferentiated PC-12 cells. Cell Death Diff. 9:2002;1007-1016.
17. Planey S.L., Abrams M.T., Robertson N.M., Litwack G. Role of apical caspases and glucocorticoid-regulated genes in glucocorticoid-induced apoptosis of pre-B leukemic cells. Cancer Res. 63:2003;172-178.
18. Zhang W., He Q., Chan L.L., Zhou F., El Naghy M., Thompson E.B., Ansari N.H. Involvement of caspases in 4-hydroxy-alkenal-induced apoptosis in human leukemic cells. Free Radic. Biol. Med. 30:2001;699-706.
19. Chen Y.C., Shen S.C., Lee W.R., Hsu F.L., Lin H.Y., Ko C.H., Tseng S.W. 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. 64:2002;1713-1724.
20. Chen Y.C., Lin-Shiau S.Y., Lin J.K. Involvement of reactive oxygen species and caspase 3 activation in arsenite induced apoptosis. J. Cell. Physiol. 177:1998;324-533.
21. Krieser R.J., Eastman A. Cleavage and nuclear translocation of the caspase 3 substrate Rho GDP-dissociation inhibitor, D4-GDI, during apoptosis. Cell Death Diff. 6:1999;412-419.
22. Muscarella D.E., Bloom S.E. Cross-linking of surface IgM in the Burkitt's lymphoma cell line ST486 provides protection against arsenite- and stress-induced apoptosis that is mediated by ERK and phosphoinositide 3-kinase signaling pathways. J. Biol. Chem. 278:2003;4358-4367.
23. 2+ influx regulates growth plate chondrocyte maturation and apoptosis. J. Biol. Chem. 278:2003;3762-3769.
24. Wittmann S., Bali P., Donapaty S., Nimmanapalli R., Guo F., Yamaguchi H., Huang M., Jove R., Wang H.G., Bhalla K. Flavopiridol down-regulates antiapoptotic proteins and sensitizes human breast cancer cells to epothilone B-induced apoptosis. Cancer Res. 63:2003;93-99.
25. Ko C.H., Shen S.C., Lin H.Y., Hou W.C., Lee W.R., Yang L.L., Chen Y.C. 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. 193:2002;93-102.
26. Chen Y.C., Liang Y.C., Lin-Shiau S.Y., Ho C.T., Lin J.K. Inhibition of TPA induced protein kinase C and transcription activator protein-1 binding activities by theaflavin-3, 3′-diagallate from black tea in NIH3T3 cells. J. Agr. Food Chem. 47:1999;1416-1421.
27. Lin J.K., Chen Y.C., Huang Y.T., Lin-Shiau S.Y. Suppression of protein kinase C and nuclear oncogene expression as possible molecular mechanism of cancer chemoprevention by apigenin and curcumin. J. Cell Biochem. 28/29:1997;39-48.
28. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods. 65:1983;55-63.
29. Chen Y.C., Tsai S.H., Shen S.C., Lin J.K., Lee W.R. Alternative activation of extracellular signal-regulated protein kinases in curcumin and arsenite induced HSP70 gene expression in human colorectal carcinoma cells. Eur. J. Cell Biol. 80:2001;213-221.
30. Chen Y.C., Lin-Shiau S.Y., Lin J.K. Involvement of p53 and HSP70 proteins in attenuation of UVC-induced apoptosis by thermal stress in hepatocellular carcinoma cells. Photochem. Photobiol. 70:1999;78-86.
31. Kurosawa M., Tani Y., Nishimura S., Numazawa S., Yoshida T. Distinct PKC isozymes regulate bufalin-induced differentiation and apoptosis in human monocytic cells. Am. J. Physiol. Cell Physiol. 280:2001;C459-C464.
32. Canat X., Guillaumont A., Bouaboula M., Poinot-Chazel C., Derocq J.M., Carayon P., LeFur G., Casellas P. Peripheral benzodiazepine receptor modulation with phagocyte differentiation. Biochem. Pharmacol. 46:1993;551-554.
33. Kim B.Y., Han M.J., Chung A.S. Effects of reactive oxygen species on proliferation of Chinese hamster lung fibroblast (V79) cells. Free Radic. Biol. Med. 30:2001;686-698.
34. Potoka D.A., Takao S., Owaki T., Bulkley G.B., Klein A.S. Endothelial cells potentiate oxidant-mediated Kupffer cell phagocytic killing. Free Radic. Biol. Med. 24:1998;1217-1227.
35. Seshiah P.N., Weber D.S., Rocic P., Valppu L., Taniyama Y., Griendling K.K. Angiotensin II stimulation of NADPH oxidase activity: upstream mediators. Circ. Res. 91:2002;406-413.
36. Yellaturu C.R., Bhanoori M., Neeli I., Rao G.N. N-Ethylmaleimide inhibits platelet-derived growth factor BB-stimulated Akt phosphorylation via activation of protein phosphatase 2A. J. Biol. Chem. 277:2002;40148-40155.
37. 2 induce caspase-3-independent degradation of Akt/protein kinase B. J. Biol. Chem. 277:2002;42943-42952.
38. Aikawa M., Sugiyama S., Hill C.C., Voglic S.J., Rabkin E., Fukumoto Y., Schoen F.J., Witztum J.L., Libby P. Lipid lowering reduces oxidative stress and endothelial cell activation in rabbit atheroma. Circulation. 106:2002;1390-1396.
39. Sugihara N., Arakawa T., Ohnishi M., Furuno K. Anti- and pro-oxidative effects of flavonoids on metal-induced lipid hydroperoxide-dependent lipid peroxidation in cultured hepatocytes loaded with alpha-linolenic acid. Free Radic. Biol. Med. 27:1999;1313-1323.
40. Lebeau J., Furman C., Bernier J.L., Duriez P., Teissier E., Cotelle N. Antioxidant properties of di-tert-butylhydroxylated flavonoids. Free Radic. Biol. Med. 29:2000;900-912.
41. Burda S., Oleszek W. Antioxidant and antiradical activities of flavonoids. J Agr. Food Chem. 49:2001;2774-2779.
42. Sadik C.D., Sies H., Schewe T. Inhibition of 15-lipoxygenases by flavonoids: structure-activity relations and mode of action. Biochem. Pharmacol. 65:2003;773-781.
43. Santos A.C., Uyemura S.A., Lopes J.L., Bazon J.N., Mingatto F.E., Curti C. Effect of naturally occurring flavonoids on lipid peroxidation and membrane permeability transition in mitochondria. Free Radic. Biol. Med. 24:1998;1455-1461.
44. Cao G., Sofic E., Prior R.L. Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Free Radic. Biol. Med. 22:1997;749-760.
45. Oliveira N.G., Rodrigues A.S., Chaveca T., Rueff J. Induction of an adaptive response to quercetin, mitomycin C and hydrogen peroxide by low doses of quercetin in V79 Chinese hamster cells. Mutagenesis. 12:1997;457-462.