Phytoestrogens as natural prodrugs in cancer prevention: Dietary flavonoids

Phytochemistry Reviews

Volumn 8, Issue 2, 2009, Pages 375-386

  Arroo, Randolph R J ^a   Androutsopoulos, Vasilis ^a   Beresford, Kenneth ^a   Ruparelia, Ketan ^a   Surichan, Somchaiya ^a   Wilsher, Nicola ^a   Potter, Gerry A ^a  

^a DE MONTFORT UNIVERSITY   (United Kingdom)

Author keywords

Cancer prevention; CYP1; Flavonoids; Metabolism

Indexed keywords

ACACETIN; APIGENIN; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 1B1; CYTOCHROME P450 2A6; CYTOCHROME P450 2B6; CYTOCHROME P450 2C19; CYTOCHROME P450 2C8; CYTOCHROME P450 3A4; DIOSMETIN; EUPATORIN; FISETIN; FLAVONE DERIVATIVE; FLAVONOID; GLUCURONOSYLTRANSFERASE; HYDROXYL GROUP; KAEMPFEROL; LUTEOLIN; MINERAL; MYRICETIN; PHYTOESTROGEN; POLYPHENOL DERIVATIVE; PRODRUG; QUERCETAGETIN; QUERCETIN; RESVERATROL; SULFOTRANSFERASE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VITAMIN;

ARTICLE; CANCER GROWTH; CANCER PREVENTION; CITRUS FRUIT; CONJUGATION; DEMETHYLATION; DIETARY INTAKE; DRUG BIOAVAILABILITY; DRUG MECHANISM; DRUG METABOLISM; ENZYME MECHANISM; FRUIT; FRUIT JUICE; GLUCURONIDATION; HUMAN; LIVER; METHYLATION; NONHUMAN; PRIORITY JOURNAL; SMALL INTESTINE; STRUCTURE ACTIVITY RELATION; SULFATION; VEGETABLE;

CITRUS;

EID: 67651174317     PISSN: 15687767     EISSN: 1572980X     Source Type: Journal    
DOI: 10.1007/s11101-009-9128-6     Document Type: Article

References (64)

1. G Agullo L Gamet-Payrastre S Manenti C Viala C Rémésy H Chap B Pyrastre 1997 Relationship between flavonoid structure and inhibition of phosphatidylinositol 3-kinase: a comparison with tyrosine kinase and protein kinase C inhibition Biochem Pharmacol 53 1649 1657 10.1016/S0006-2952(97)82453-7
2. BN Ames 1983 Dietary carcinogens and anticarcinogens: oxygen radicals and degenerative diseases Science 221 1256 1264 10.1126/science.6351251
3. V Androutsopoulos RRJ Arroo JF Hall S Surichan GA Potter 2008 Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1 mediated metabolism Breast Cancer Res 10 R39 10.1186/bcr2090
4. V Androutsopoulos N Wilsher RRJ Arroo GA Potter 2009 Bioactivation of the phytoestrogen diosmetin by CYP1 Cytochromes P450 Cancer Lett 274 54 60 10.1016/j.canlet.2008.08.032
5. RRJ Arroo V Androutsopoulos A Patel S Surichan N Wilsher GA Potter 2008 Phytoestrogens as natural prodrugs in cancer: a novel concept Phytochem Rev 7 431 443 10.1007/s11101-008-9093-5
6. J Bektic R Guggenberger B Spengler V Christoffel A Pelzer AP Berger R Ramoner G Bartsch H Klocker 2006 The flavonoid apigenin inhibits the proliferation of prostatic stromal cells via the MAPK-pathway and cell-cycle arrest in G1/S Maturitas 55 Supplement S37 S46 10.1016/j.maturitas.2006.06.015
7. V Benetou A Trichopoulou P Orfanos A Naska P Lagiou P Boffetta D Trichopoulos 2008 Conformity to traditional Mediterranean diet and cancer incidence: the Greek EPIC cohort Br J Cancer 99 191 195 10.1038/sj.bjc.6604418
8. CS Bestwick Milne l 2006 Influence of galangin on HL-60 cell proliferation and survival Cancer Lett 243 80 89 10.1016/j.canlet.2005.11.025
9. G Bjelakovics D Nikolova L Gluud RG Simonetti C Gluud 2007 Mortality in randomized trials of antioxidant supplements for primary and secondary prevention systematic review and meta-analysis JAMA 297 842 857 10.1001/jama.297.8.842
10. JF Borzelleca 2000 Paracelsus: herald of modern toxicology Toxicol Sci 53 2 4 10.1093/toxsci/53.1.2
11. VM Breinholt EA Offord C Brouwer SE Nielsen K Brøsen TH Friedberg 2002 In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids Food Chem Toxicol 40 609 616 10.1016/S0278-6915(01)00125-9
12. VM Breinholt SE Rasmussen K Brøsen TH Friedberg 2003 In vitro metabolism of genistein and tangeretin by human and murine cytochrome P450s Pharmacol Toxicol 93 14 22 10.1034/j.1600-0773.2003.930102.x
13. DDG Bugano N Conforti-Froes NH Yamaguchi EC Baracat 2008 Genetic polymorphisms, the metabolism of estrogens and breast cancer: a review Eur J Gynaecol Oncol 29 313 320
14. R Cailleau M Olive QVJ Crueiger 1978 Long term human breast carcinoma cell lines of metastatic origin: preliminary characterization In Vitro 14 911 915 10.1007/BF02616120 (Pubitemid 9089089)
15. HY Chan ZY Chen DSC Tsang LK Leung 2002 Baicalein inhibits DMBA-DNA adduct formation by modulating CYP1A1 and CYP1B1 activities Biomed Pharmacother 56 269 275 10.1016/S0753-3322(02)00192-0
16. TKH Chang J Chen EYH Yeung 2006 Effect of Ginkgo biloba extract on procarcinogen-bioactivating human CYP1 enzymes: identification of isorhamnetin, kaempferol, and quercetin as potent inhibitors of CYP1B1 Toxicol Appl Pharmacol 213 18 26 10.1016/j.taap.2005.09.007
17. A Chaudhary KL Willett 2006 Inhibition of human cytochrome CYP1 enzymes by flavonoids of St. John's wort Toxicol 217 194 205 10.1016/j.tox.2005.09.010
18. HP Ciolino GC Yeh 1999 The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor Br J Cancer 79 1340 1346 10.1038/sj.bjc.6690216 (Pubitemid 29116788)
19. HP Ciolino TTY Wang GC Yeh 1998 Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity Cancer Res 58 2754 2760 (Pubitemid 28311904)
20. HP Ciolino PJ Daschner GC Yeh 1999 Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially Biochem J 340 715 722 10.1042/0264-6021:3400715
21. ID Coulter ML Hardy SC Morton LG Hilton W Tu D Valentine PG Shekelle 2006 Antioxidants vitamin C and vitamin E for the prevention and treatment of cancer J Gen Intern Med 21 735 744 10.1111/j.1525-1497.2006.00483.x
22. V Dilis E Vasilopoulou A Trichopoulou 2007 The flavone, flavonol and flavan-3-ol content of the Greek traditional diet Food Chem 105 812 821 10.1016/j.foodchem.2007.01.069
23. H Doostdar MD Burke RT Mayer 2000 Bioflavonoids: selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1 Toxicol 144 31 38 10.1016/S0300-483X(99)00215-2
24. JC Espin MT Garcia-Conesa FA Tomas-Barberan 2007 Nutraceuticals: facts and fiction Phytochemistry 68 2986 3008 10.1016/j.phytochem.2007.09.014
25. Y Fujii-Kuriyama J Mimura 2005 Molecular mechanisms of AhR functions in the regulation of cytochrome P450 genes Biochem Biophys Res Commun 338 311 317 10.1016/j.bbrc.2005.08.162
26. S Gupta F Afaq H Mukhtar 2002 Involvement of nuclear factor-kappa B, Bax and Bcl-2 in induction of cell cycle arrest and apoptosis by apigenin in human prostate carcinoma cells Oncogene 21 3727 3738 10.1038/sj.onc.1205474 (Pubitemid 34620536)
27. Halliwell B, Rafter J, Jenner A (2005) Health promotion by flavonoids, tocopherols, tocotrienols, and other phenols: direct or indirect effects? Antioxidant or not? Am J Clin Nutr 81:268S-276S (Suppl. S)
28. M Heinonen 2007 Antioxidant activity and antimicrobial effect of berry phenolics-a Finnish perspective Mol Nutr Food Res 51 684 691 10.1002/mnfr.200700006
29. S Holder M Zemskova C Zhang M Tabrizizad R Bremer JW Neidigh MB Lilly 2007 Characterization of a potent and selective small-molecule inhibitor of the PIM1 kinase Mol Cancer Ther 6 163 172 10.1158/1535-7163.MCT-06-0397
30. D Ichimatsu M Nomura S Nakamura S Moritani K Yokogawa S Kobayashi T Nishioka K Miyamoto 2007 Structure-activity relationship of flavonoids for inhibition of epidermal growth factor-induced transformation of JB6 CI 41 cells Mol Carcinog 46 436 445 10.1002/mc.20292
31. P Kaur S Shukla S Gupta 2008 Plant flavonoid apigenin inactivates Akt to trigger apoptosis in human prostate cancer: an in vitro and in vivo study Carcinogenesis 29 2210 2217 10.1093/carcin/bgn201
32. JH Kim KH Stansbury NJ Walker MA Trush PT Strickland TR Sutter 1998 Metabolism of benzo[a]pyrene and benzo[a]pyrene-7, 8-diol by human cytochrome P450 1B1 Carcinogenesis 19 1847 1853 10.1093/carcin/19.10.1847
33. HJ Kim SB Lee SK Park HM Kim YI Park MS Dong 2005 Effects of hydroxyl group numbers on the B-ring of 5, 7-dihydroxyflavones on the differential inhibition of human CYP 1A and CYP1B1 enzymes Arch Pharm Res 28 1114 1121
34. P Kisselev WH Schunck I Roots D Schwarz 2005 Association of CYP1A1 polymorphisms with differential metabolic activation of 17β-estradiol and estrone Cancer Res 65 2972 2978 10.1158/0008-5472.CAN-04-3543
35. N Koga M Matsuo C Ohta K Haraguchi M Matsuoka Y Kato T Ishii M Yano H Ohta 2007 Comparative study on nobiletin metabolism with liver microsomes from rats, guinea pigs and hamsters and rat cytochrome P450 Biol Pharm Bull 30 2317 2323 10.1248/bpb.30.2317
36. JA Lavigne JE Goodman T Fonong S Odwin P He DW Roberts JD Yager 2001 The effects of catechol-O-methyltransferase inhibition on estrogen metabolite and oxidative damage levels in estradiol-treated MCF-7 cells Cancer Res 61 7488 7494 (Pubitemid 32995038)
37. SB Lotito B Frei 2006 Consumption of flavonoid-rich foods and increased plasma antioxidant capacity in humans: cause, consequence, or epiphenomenon? Free Radic Biol Med 41 1727 1746 10.1016/j.freeradbiomed.2006.04.033
38. McFadyen WT Melvin GI Murray 2004 Cytochrome P450 enzymes: novel options for cancer therapeutics Mol Cancer Ther 3 363 371 (Pubitemid 39193712)
39. SM Mense TK Hei RK Ganju HK Bhat 2008 Phytoestrogens and breast cancer prevention: possible mechanisms of action Environ Health Perspect 116 426 433 (Pubitemid 351864298)
40. SM Mense J Chhabra HK Bhat 2008 Preferential induction of cytochrome P450 1A1 over cytochrome P450 1B1 in human breast epithelial cells following exposure to quercetin J Steroid Biochem Mol Biol 110 157 162 10.1016/j.jsbmb.2008.03.029
41. YJ Moon X Wang ME Morris 2006 Dietary flavonoids: effects on xenobiotic and carcinogen metabolism Toxicol In Vitro 20 187 210 10.1016/j.tiv.2005.06.048
42. GI Murray MC Taylor McFadyen JA McKay WF Greenlee MD Burke WT Melvin 1997 Tumor specific expression of cytochrome P450 CYP1B1 Cancer Res 57 3026 3031 (Pubitemid 27315056)
43. Murray GI, Melvin WT, McFadyen M (2003) Use of CYP1B1 inhibitors for treating cancer. Patent Application Publication US 2003/0162727 A1
44. B Piver M Fer X Vitrac JM Merillon Y Dreano F Berthou D Lucas 2004 Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes Biochem Pharmacol 68 773 782 10.1016/j.bcp.2004.05. 008
45. Potter GA, Patterson LH, Burke MD (2002a) Hydroxylation activated prodrugs. Patent Application Publication US 2001/0021717 Al
46. GA Potter LH Patterson E Wanogho PJ Perry PC Butler T Ijaz KC Ruparelia JH Lamb PB Farmer LA Stanley MD Burke 2002 The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1 Br J Cancer 86 774 778 10.1038/sj.bjc.6600197
47. D Puppala CG Gairola HI Swanson 2007 Identification of kaempferol as an inhibitor of cigarette smoke-induced activation of the aryl hydrocarbon receptor and cell transformation Carcinogenesis 28 639 647 10.1093/carcin/bgl169
48. M Rahman CH Sutter GL Emmert TR Sutter 2006 Regioselective 2-hydroxylation of 17β-estradiol by rat cytochrome P4501B1 Toxicol Appl Pharmacol 216 469 478 10.1016/j.taap.2006.06.004
49. IMCM Rietjens MG Boersma H van der Woude SMF Jeurissen ME Schutte GM Alink 2005 Flavonoids and alkenylbenzenes: mechanisms of mutagenic action and carcinogenic risk Mutat Res 574 124 138 10.1016/j.mrfmmm.2005.01.028
50. B Rochat JM Morsman GI Murray WD Figg HL Mcleod 2001 Human CYP1B1 and anticancer agent metabolism: mechanism for tumor-specific drug inactivation? J Pharmacol Exp Ther 296 537 541 (Pubitemid 32112483)
51. HY Shim JH Park HD Paik SY Nah DSHL Kim YS Han 2007 Acacetin-induced apoptosis of human breast cancer MCF-7 cells involves caspase cascade, mitochondriamediated death signaling and SAPK/JNK1/2-c-Jun activation Mol Cells 24 95 104 (Pubitemid 47554796)
52. T Shimada EMJ Gillam TR Sutter PT Strickland FP Guengerich H Yamazaki 1997 Oxidation of xenobiotics by recombinant human cytochrome P450 1B1 Drug Metab Dispos 25 617 622 (Pubitemid 27213104)
53. RP Singh P Agrawal D Yim C Agarwal R Agarwal 2005 Acacetin inhibits cell growth and cell cycle progression, and induces apoptosis in human prostate cancer cells; structure-activity relationship with linarin and linarin acetate Carcinogenesis 26 845 854 10.1093/carcin/bgi014
54. HD Soule TM Maloney SR Wolman WD Peterson Jr R Brenz 1990 Isolation and characterization of a spontaneously immortalized human breast epithelial cell line, MCF-10 Cancer Res 50 6075 6086 (Pubitemid 20331424)
55. D Utesch K Feige J Dasenbrock TH Broschard M Harwood B Danielewska-Nikiel TC Lines 2008 Evaluation of the potential in vivo genotoxicity of quercetin Mutat Res 654 38 44
56. M Valko CJ Rhodes J Moncol 2006 Free radicals, metals and antioxidants in oxidative stress-induced cancer Chem-Biol Int 60 1 40 (Pubitemid 43227479)
57. T Walle 2007 Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass? Semin Cancer Biol 17 354 362 10.1016/j.semcancer.2007.05.002
58. UK Walle T Walle 2007 Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones Drug Metab Dispos 35 1985 1989 10.1124/dmd.107.016782
59. H Wang Y Wang ZY Chen FL Chan LK Leung 2005 Hydroxychalcones exhibit differential effects on XRE transactivation Toxicol 207 303 313 10.1016/j.tox.2004.10.005
60. X Wen UK Walle T Walle 2005 5, 7-Dimethoxyflavone downregulates CYP1A1 expression and benzo[a]pyrene-induced DNA binding in Hep G2 cells Carcinogenesis 26 803 809 10.1093/carcin/bgi015
61. WC Willett F Sacks A Trichopoulou G Drescher A Ferroluzzi E Helsing D Trichopoulos 1995 Mediterranean diet pyramid-a cultural model for healthy eating Am J Clin Nutr 61 Supplement S1402 S1406
62. WC Willett F Sacks A Trichopoulou G Drescher A Ferro-Luzzi E Helsing D Trichopoulos 1995 Mediterranean diet pyramid: a cultural model for healthy eating Am J Clin Nutr 61 1402S 1406S
63. World Cancer Research Fund/American Institute for Cancer Research (2007) Food, Nutrition, Physical Activity, and the Prevention of Cancer: a Global Perspective. AICR, Washington DC
64. BT Zhu EL Ezell JG Liehr 1994 Catechol-O-methyltransferase-catalyzed rapid O-methylation of mutagenic flavonoids J Biol Chem 269 292 299