Selective apoptotic effects of piceatannol and myricetin in human cancer cells

Journal of Applied Toxicology

Volumn 32, Issue 12, 2012, Pages 986-993

  Morales, Paloma ^a   Haza, Ana I ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Apoptosis; Myricetine; Piceatannol; Reactive oxygen species

Indexed keywords

MYRICETIN; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; PICEATANNOL; POLYPHENOL DERIVATIVE; REACTIVE OXYGEN METABOLITE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BIOSYNTHESIS; CANCER CELL; CANCER CELL CULTURE; CELL ASSAY; CELL DEATH; CELL STRAIN HEPG2; CELL STRAIN HL 60; CHROMATIN CONDENSATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG MECHANISM; DRUG POTENTIATION; DRUG SELECTIVITY; ENZYME MODIFICATION; FLOW CYTOMETRY; HUMAN; HUMAN CELL; NICK END LABELING; PRIORITY JOURNAL; RED WINE;

ANTICARCINOGENIC AGENTS; APOPTOSIS; BLOTTING, WESTERN; CELL CULTURE TECHNIQUES; CELL SURVIVAL; FLAVONOIDS; FLOW CYTOMETRY; HEP G2 CELLS; HL-60 CELLS; HUMANS; IN SITU NICK-END LABELING; POLYPHENOLS; REACTIVE OXYGEN SPECIES; STILBENES;

EID: 84868147312     PISSN: 0260437X     EISSN: 10991263     Source Type: Journal    
DOI: 10.1002/jat.1725     Document Type: Article

References (47)

1. Cantos E, Espin JC, Fernandez MJ, Oliva J, Tomas-Barberan FA. 2003. Postharvest UV-C-irradiated grapes as a potential source for producing stilbene-enriched red wines. J. Agric. Food Chem. 51: 1208-1214.
2. Chung LY, Cheung TC, Kong SK, Fung KP, Choy YM, Chan ZY, Kwok TT. 2001. Induction of apoptosis by green tea catechins in human prostate cancer DU145 cells. Life Sci. 68: 1207-1214.
3. Das DK, Maulik N. 2006. Resveratrol in cardioprotection: a therapeutic promise of alternative medicine. Mol. Interv. 6: 36-47.
4. Davis CD. 2007. Nutritional Interactions: credentialing of molecular targets for cancer prevention. Exp. Biol. Med. 232: 176-183.
5. DiBartolomeis SM, Moné JP. 2003. Apoptosis: a four-week laboratory investigation for advanced molecular and cellular biology students. Cell Biol. Educ. 2: 275-952.
6. Elattar T, Virji A. 2000. The inhibitory effect of curcumin, genistein, quercetin and cisplatin on the growth of oral cancer cells in vitro. Anticancer Res. 20: 1733-1738.
7. Fresco P, Borges F, Marques MPM, Diniz C. 2010. The anticancer properties of dietary polyphenols and its relation with apoptosis. Curr. Pharm. Des. 16: 114-134.
8. Fritzer-Szekeres M, Savinc I, Horvath Z, Saiko P, Pemberger M, Graser G, Bernhaus A, Ozsvar-kozma M, Grusch M, Jaeger W, Szekeres T. 2008. Biochemical effects of piceatannol in human HL-60 promyelocytic leukemia cells - synergism with Ara-C. Int. J. Oncol. 33: 887-892.
9. García A, Morales P, Arranz N, Delgado E, Rafter J, Haza AI. 2009. Antiapoptotic effects of dietary antioxidants towards N-nitrosdopiperidine and N-nitrosodibutylamine-induced apoptosis in HL60 and HepG2 cells. J. Appl. Toxicol. 29: 403-413.
10. Granado-Serrano AB, Martín MA, Izquierdo-Pulido M, Goya L, Bravo L, Ramos S. 2007. Molecular mechanisms of (-)-epicatechin and chlorogenic acid on the regulation of the apoptotic and survival/proliferation pathways in a human hepatoma cell line. J. Agric. Food Chem. 55: 2020-2027.
11. Hwang JT, Ha J, Park O. 2005. Combination of 5-fluorouracil and genistein induces apoptosis synergistically in chemo-resistant cancer cells through the modulation of AMPK and COX-2 signaling pathways. Biochem. Biophys. Res. Comm. 332: 433-440.
12. Iriti M, Faoro F. 2010. Bioactive chemicals and health benefits of grapevine products. In Bioactive Foods in Promoting Health: Fruits and Vegetables, Watson R, Preedy VR (eds). Elsevier Science & Technology: Oxford; 581-620.
13. Khan N, Adhami VM, Mukhtar H. 2008. Apoptosis by dietary agents for prevention and treatment of cancer. Biochem. Pharmacol. 76: 1333-1339.
14. Kim W, Yang HJ, Youn H, Yun YJ, Seong KM, Youn B. 2010. Myricetin inhibits Akt survival signaling and induces Bad-mediated apoptosis in a low dose ultraviolet (UV)-B-irradiatedHaCaT human immortalized keratinocytes. J. Radiat. Res. 51: 285-296.
15. Kim YH, Park C, Lee JO, Kim GY, Lee WH, Choi YH, Ryu CH. 2008. Induction of apoptosis by piceatannol in human leukemic U937 cells through down-regulation of Bcl-2 and activation of caspases. Oncol. Rep. 19: 961-967.
16. Ko CH, Shen S-C, Hsu CS, Chen YC. 2005. Mitochondrial-dependent, reactive oxygen species-independent apoptosis by myricetin: roles of protein kinase C, cytochrome c, and caspase cascade. Biochem. Pharmacol. 69: 913-927.
17. Kumamoto T, Fujii M, Hou D-X. 2009. Myricetin directly targets JAK1 to inhibit cell transformation. Cancer Lett. 275: 17-26.
18. Lambert JD, Elias RJ. 2010. The antioxidant and pro-oxidant activities of green tea polyphenols: A role in cancer prevention. Arch. Biochem. Biophys. 50: 65-72.
19. Larrosa M, Tomás-Barberán FA, Espín JC. 2004. The grape and wine polyphenol piceatannol is a potent inducer of apoptosis in human SK-Mel-28 melanoma cells. Eur. J. Nutr. 43: 275-284.
20. - MAPK-mediated activation of c-Jun and ATF-2 pathways. Int. J. Biochem. Cell Biol. 42: 1498-1506.
21. Manach C, Scalbert A, Morand C, Rémésy C, Jiménez L. 2004. Polyphenols: food sources and bioavailability. Am. J. Clin. Nutr. 79: 727-747.
22. Martin KR. 2006. Targeting apoptosis with dietary bioactive agents. Exp. Biol. Med. 231: 117-129.
23. McDonald MS, Hughes M, Burns J, Lean ME, Matthews D, Crozier A. 1998. Survey of the free and conjugated myricetin and quercetin content of red wines of different geographical origins. J. Agric. Food Chem. 46: 368-375.
24. Mertens-Talcott S, Percival S. 2005. Ellagic acid and quercetin interact synergistically with resveratrol in the induction of apoptosis and cause transient cell cycle arrest in human leukemia cells. Cancer Lett. 218: 141-151.
25. Mouria M, Gukovskaya A, Jung Y, Buechler P, Hines O, Reber H. 2002. Food-derived polyphenols inhibit pancreatic cancer growth through mitochondrial cytochrome c release and apoptosis. Int. J. Cancer 98: 761-769.
26. Nair H, Rao K, Aalinkeel R, Mahajan S, Chawda R, Schwartz S. 2004. Inhibition of prostate cancer cell colony formation by the flavonoid quercetin correlates with modulation of specific regulatory genes. Clin. Diagnostic. Lab. Immunol. 11: 63-69.
27. Nichenametla SN, Taruscio TG, Barney DL, Exon JH. 2006. A review of the effects and mechanisms of polyphenolics in cancer. Crit. Rev. Food Sci. Nutr. 46: 161-183.
28. Okada H, Mak TW. 2004. Pathways of apoptotic and non-apoptotic death in tumour cells. Nat. Rev. Cancer 4: 592-602.
29. Ong KC, Khoo HE.1997. Biological effects of myricetin. Gen. Pharmacol. 29: 121-126.
30. Pandey KB, Rizvi SI. 2009. Protective effect of resveratrol on formation of membrane protein carbonyls and lipid peroxidation in erythrocytes subjected to oxidative stress. Appl. Physiol. Nutr. Metab. 34: 1093-1097.
31. Piver B, Fer M, Vitrac X, Merillon JM, Dreano Y, Berthou F, Lucas D. 2004. Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes. Biochem. Pharmacol. 68: 773-782.
32. Ramos S, Aliaa M, Bravo L, Goya L. 2005. Comparative effects of food-derived polyphenols on the viability and apoptosis of a human hepatoma cell line (HepG2). J. Agric. Food Chem. 53: 1271-1280.
33. Ramos S. 2007. Effects of dietary flavonoids on apoptotic pathways related to cancer chemoprevention. J. Nutr. Biochem. 18: 427-442.
34. Ramos S. 2008. Cancer chemoprevention and chemotherapy: dietary polyphenols and signalling pathways. Mol. Nutr. Food Res. 52: 507-526.
35. Renaud S, De Lorgeril M. 1992. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet 339:1523-1526.
36. Rodrigo R, Miranda A, Vergara L. 2010. Modulation of endogenous antioxidant system by wine polyphenols in human disease. Clin. Chim. Acta 412: 410-424.
37. Sakamoto K. 2000. Synergistic effects of thearubigin and genistein on human prostate tumor cell (PC-3) growth via cell cycle arrest. Cancer Lett. 151: 103-109.
38. Scalbert A, Johnson IT, Saltmarsh M. 2005. Polyphenols: antioxidants and beyond. Am. J. Clin. Nutr. 81: 215-217.
39. Teugo PW, Fauconneau B, Deffieux G, Huguet F, Vercauteren J, Merillon JM. 1998. Isolation, identification, and antioxidant activity of three stilbene glucosides newly extracted from Vitis vinifera cell cultures. J. Nat. Prod. 61: 655-657.
40. Vittal R, Selvanayagam ZE, Hong J, Chin KV, Yang CS. 2004. Gene expression changes induced by green tea polyphenol (-)-epigallocatechin-3-gallate in human bronchial epithelial 21BES cells by DNA microarray. Mol. Cancer Ther. 3: 1091-1099.
41. Vuorinen H, Maatta K, Torronen R. 2000. Content of the flavonols myricetin, quercetin, and kaempferol in finnish berry wines. J. Agric. Food Chem. 48: 2675-2680.
42. Wätjen W, Michels G, Steffan B, Niering P, Chovolou Y, Kampkftter A, Tran-Thi QH, Peter Proksch P, Kahl R. 2005. Low concentrations of flavonoids are protective in rat H4IIE cells whereas high concentrations cause DNA damage and apoptosis. J. Nutr. 135: 525-531.
43. Watson W, Cai J, Jones DP. 2000. Diet and apoptosis. Annu. Rev. Nutr. 20: 485-505.
44. Weinreb O, Mandel S, Youdim M. 2003. cDNA gene expression profile homology of antioxidants and their antiapoptotic and proapoptotic activities in human neuroblastoma cells. FASEB J. 17: 935-937.
45. Wolter F, Clausnitzer A, Akoglu B, Stein J. 2002. Piceatannol, a natural analog of resveratrol, inhibits progression through the s phase of the cell cycle in colorectal cancer cell lines. J. Nutr. 132: 298-302.
46. Xu J, Loo G. 2001. Different effects of genistein on molecular marker related to apoptosis in two phenotypically dissimilar breast cancer cell lines. J. Cell. Biochem. 82: 78-88.
47. Zheng Q, Hirose Y, Yoshimi N, Murakami A, Koshimizu M, Ohigashi H, Sakata K, Matsumoto Y, Sayama Y, Mori H. 2002. Further investigation of the modifying effect of various chemopreventive agents on apoptosis and cell proliferation in human colon cancer cells. J. Cancer Res. Clin. Oncol. 128: 539-546.