Erucin, a new promising cancer chemopreventive agent from rocket salads, shows anti-proliferative activity on human lung carcinoma A549 cells

Food and Chemical Toxicology

Volumn 47, Issue 7, 2009, Pages 1430-1436

  Melchini, A ^a   Costa, C ^b   Traka, M ^c   Miceli, N ^a   Mithen, R ^c   De Pasquale, R ^a   Trovato, A ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

^c NORWICH RESEARCH PARK   (United Kingdom)

Author keywords

Apoptosis; Cell cycle; Chemoprevention; Erucin; Lung cancer; Sulforaphane

Indexed keywords

ERUCIN; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE 1; PROTEIN P21; PROTEIN P53; SULFORAPHANE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER PREVENTION; CELL CYCLE ARREST; CELL PROLIFERATION; CONTROLLED STUDY; ENZYME DEGRADATION; FUNCTIONAL FOOD; HUMAN; HUMAN CELL; LUNG ADENOCARCINOMA; PROTEIN EXPRESSION; PROTEIN INDUCTION;

ANTICARCINOGENIC AGENTS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; BLOTTING, WESTERN; BRASSICACEAE; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; CHROMATOGRAPHY, LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; ISOTHIOCYANATES; LUNG NEOPLASMS; MASS SPECTROMETRY; ONCOGENE PROTEIN P21(RAS); POLY(ADP-RIBOSE) POLYMERASES; SPECTROMETRY, FLUORESCENCE; SULFIDES; THIOCYANATES; TUMOR SUPPRESSOR PROTEIN P53;

DIPLOTAXIS; ERUCA SATIVA; ERUCA VESICARIA;

EID: 67349224103     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2009.03.024     Document Type: Article

References (58)

1. Barillari J., Iori R., Papi A., Orlandi M., Bartolini G., Gabbanini S., Pedulli G.F., and Valgimigli L. Kaiware Daikon (Raphanus sativus L.) extract: a naturally multipotent chemopreventive agent. J. Agric. Food Chem. 56 (2008) 7823-7830
2. Bertl E., Bartsch H., and Gerhäuser C. Inhibition of angiogenesis and endothelial cell functions are novel sulforaphane-mediated mechanisms in chemoprevention. Mol. Cancer Ther. 5 (2006) 575-585
3. Bianchini F., and Vainio H. Isothiocyanates in cancer prevention. Drug Metab. Rev. 36 (2004) 655-667
4. Bonnesen C., Eggleston I.M., and Hayes J.D. Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines. Cancer Res. 61 (2001) 6120-6130
5. Brennan P., Hsu C.C., Moullan N., Szeszenia-Dabrowska N., Lissowska J., Zaridze D., Rudnai P., Fabianova E., Mates D., Bencko V., Foretova L., Janout V., Gemignani F., Chabrier A., Hall J., Hung R.J., Boffetta P., and Canzian F. Effect of cruciferous vegetables on lung cancer in patients stratified by genetic status: a mendelian randomisation approach. Lancet 366 (2005) 1558-1560
6. Chuang L.T., Moqattash S.T., Gretz H.F., Nezhat F., Rahaman J., and Chiao J.W. Sulforaphane induces growth arrest and apoptosis in human ovarian cancer cells. Acta Obstet. Gynecol. Scand. 16 (2007) 1-6
7. Clarke J.D., Dashwood R.H., and Ho E. Multi-targeted prevention of cancer by sulforaphane. Cancer Lett. 269 (2008) 291-304
8. Conaway C.C., Krzeminski J., Amin S., and Chung F.L. Decomposition rates of isothiocyanate conjugates determine the activity as inhibitors of cytochrome P450 isozymes. Chem. Res. Toxicol. 14 (2001) 1170-1176
9. Conaway C.C., Wang C.X., Pittman B., Yang Y.M., Schwartz J.E., Tian D., McIntee E.J., Hecth S.S., and Chung F.L. Phenethyl isothiocyanate and sulforaphane and their N-acetylcysteine conjugates inhibit malignant progression of lung adenomas induced by tobacco carcinogens in A/J mice. Cancer Res. 5 (2005) 548-557
10. Cuddihy S.L., Brown K.K., Thomson S.J., and Hampton M.B. Induction of apoptosis by phenethyl isothiocyanate in cells overexpressing Bcl-X(L). Cancer Lett. Drug News Perspect. 18 (2008) 445-451
11. Dashwood R.H., and Ho E. Dietary histone deacetylase inhibitors: from cells to mice to man. Semin. Cancer Biol. 17 (2007) 363-369
12. Fimognari C., and Hrelia P. Sulforaphane as a promising molecule for fighting cancer. Mutat. Res. 635 (2007) 90-104
13. Fimognari C., Nusse M., Berti F., Iori R., Cantelli-Forti G., and Hrelia P. Cyclin D3 and p53 mediate sulforaphane-induced cell cycle delay and apoptosis in non-transformed human T lymphocytes. Cell. Mol. Life Sci. 59 (2002) 2004-2012
14. Fimognari C., Nusse M., Iori R., Cantelli-Forti G., and Hrelia P. Sulforaphane modulate cell cycle and apoptosis in transformed and non-transformed human T lymphocytes. Ann. NY Acad. Sci. 1010 (2003) 393-398
15. Fimognari C., Nusse M., Iori R., Cantelli-Forti G., and Hrelia P. The new isothiocyanate 4-(methylthio)butylisothiocyanate selectively affects cell cycle progression and apoptosis induction of human leukemia cells. Invest. New Drugs 22 (2004) 119-129
16. Giovannucci E., Rimm E.B., Liu Y., Stampfer M.J., and Willett W.C. A prospective study of cruciferous vegetables and prostate cancer. Cancer Epidemiol. Biomark. Prev. 12 (2003) 1403-1409
17. Guessousa I., Cornuzb J., and Paccauda F. Lung cancer screening: current situation and perspective. Swiss Med. Wkly. 137 (2007) 304-311
18. Harris K.E., and Jeffery H.E. Sulforaphane and erucin increase MRP1 and MRP2 in human carcinoma cell lines. J. Nutr. Biochem. 19 (2008) 246-254
19. Hecht S.S. Inhibition of carcinogenesis by isothiocyanates. Drug Metab. Rev. 32 (2000) 395-411
20. Heeres J.T., and Hergenrother P.J. Poly(ADP-ribose) makes a date with death. Curr. Opin. Chem. Biol. 11 (2007) 644-653
21. Higdon J.V., Delage B., Williams D.E., and Dashwood R.H. Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis. Pharmacol. Res. 55 (2007) 224-236
22. Jadhav U., Ezhilarasan R., Vaughn S.F., Berhow M.A., and Mohanam S. Iberin induces cell cycle arrest and apoptosis in human neuroblastoma cells. Int. J. Mol. Med. 19 (2007) 353-361
23. Jakubikova J., Bao Y., and Sedlak J. Isothiocyanates induce cell cycle arrest, apoptosis and mitochondrial potential depolarization in HL-60 and multidrug-resistant cell lines. Anticancer. Res. 25 (2005) 3375-3386
24. Jiao D., Smith T.J., Yang C.S., Pittman B., Desai D., Amin S., and Chung F.L. Chemopreventive activity of thiol conjugates of isothiocyanates for lung tumorigenesis. Carcinogenesis 18 (1997) 2143-2147
25. Juge N., Mithen R.F., and Traka M. Molecular basis for chemoprevention by sulforaphane: a comprehensive review. Cell. Mol. Life Sci. 64 (2007) 1105-1127
26. Kassahun K., Davis M., Hu P., Martin B., and Baillie T. Biotransformation of the naturally occurring isothiocyanate sulforaphane in the rat: identification of phase I metabolites and glutathione conjugates. Chem. Res. Toxicol. 10 (1997) 1228-1233
27. Keck A.S., and Finley JW. Cruciferous vegetables: cancer protective mechanisms of glucosinolate hydrolysis products and selenium. Integr. Cancer Ther. 3 (2004) 5-12
28. Keum Y.S., Jeong W.S., and Kong A.N. Chemopreventive functions of isothiocyanates. Drug News Perspect. 18 (2005) 445-451
29. Kristal A.R., and Lampe J.W. Brassica vegetables and prostate cancer risk: a review of the epidemiological evidence. Nutr. Cancer. 42 (2002) 1-9
30. Kuang Y.F., and Che Y.H. Induction of apoptosis in a non-small cell human lung cancer cell line by isothiocyanates is associated with P53 and P21. Food Chem. Toxicol. 42 (2004) 1711-1718
31. Lampe J.W., and Peterson S. Brassica biotransformation and cancer risk: genetic polymorphisms alter the preventive effects of cruciferous vegetables. J. Nutr. 132 (2002) 2991-2994
32. Lamy E., Schröder J., Paulus S., Brenk P., Stahl T., and Mersch-Sundermann V. Antigenotoxic properties of Eruca sativa (rocket plant), erucin and erysolin in human hepatoma (HepG2) cells towards benzo(a)pyrene and their mode of action. Food Chem. Toxicol. 46 (2008) 2415-2421
33. Leoni O., Iori R., Palmieri S., Esposito E., Menegatti E., Cortesi R., and Nastruzzi C. Myrosinase-generated isothiocyanate from glucosinolates: isolation, characterization and in vitro antiproliferative studies. Bioorg. Med. Chem. 5 (1997) 1799-1806
34. Lewis S., Brennan P., Nyberg F., Ahrens W., Constantinescu V., Mukeria A., Benhamou S., Batura-Gabryel H., Bruske-Hohlfeld I., Simonato L., Menezes A., and Boffetta P. Cruciferous vegetable intake, GSTM1 genotype and lung cancer risk in a non-smoking population. IARC Sci. Publ. 156 (2002) 507-508
35. Lynn A., Collins A., Fuller Z., Hillman K., and Ratcliffe B. Cruciferous vegetables and colo-rectal cancer. Proc. Nutr. Soc. 65 (2006) 135-144
36. Mas S., Crescenti A., Gassó P., Deulofeu R., Molina R., Ballesta A., Kensler T.W., and Lafuente A. Induction of apoptosis in HT-29 cells by extracts from isothiocyanates-rich varieties of Brassica oleracea. Nutr. Cancer 58 (2007) 107-114
37. Mi L., Wang X., Govind S., Hood B.L., Veenstra T.D., Conrads T.P., Saha D.T., Goldman R., and Chung F.L. The role of protein binding in induction of apoptosis by phenethyl isothiocyanate and sulforaphane in human non-small lung cancer cells. Cancer Res. 67 (2007) 13
38. Mi L., Xiao Z., Hood B.L., Dakshanamurthy S., Wang X., Govind S., Conrads T.P., Veenstra T.D., and Chung F.L. Covalent binding to tubulin by isothiocyanates. A mechanism of cell growth arrest and apoptosis. J. Biol. Chem. 283 (2008) 22136-22146
39. Munday R., and Munday C.M. Induction of phase II detoxification enzymes in rats by plant-derived isothiocyanates: comparison of allyl isothiocyanate with sulforaphane and related compounds. J. Agric. Food Chem. 52 (2004) 1867-1871
40. Munday R., Zhang Y., Fahey J.W., Jobson H.E., Munday C.M., Li J., and Stephenson K.K. Evaluation of isothiocyanates as potent inducers of carcinogen-detoxifying enzymes in the urinary bladder: critical nature of in vivo bioassay. Nutr. Cancer 54 (2006) 223-231
41. Munday R., Mhawech-Fauceglia P., Munday C.M., Paonessa J.D., Tang L., Munday J.S., Lister C., Wilson P., Fahey J.W., Davis W., and Zhang Y. Inhibition of urinary bladder carcinogenesis by broccoli sprouts. Cancer Res. 68 (2008) 1593-1600
42. Murillo G., and Mehta R.G. Cruciferous vegetables and cancer prevention. Nutr. Cancer 41 (2001) 17-28
43. Nastruzzi C., Cortesi R., Esposito E., Menegatti E., Leoni O., Iori R., and Palmieri S. In vitro anti-proliferative activity of isothiocyanates and nitriles generated by myrosinase-mediated hydrolysis of glucosinolates from seeds of cruciferous vegetables. J. Agric. Food Chem. 48 (2000) 3572
44. Papi A., Orlandi M., Bartolini G., Barillari J., Iori P., Paolini M., Ferroni F., Fumo M.G., Pedulli G.F., and Valgimigli L. Cytotoxic and antioxidant activity of 4-methylthio-3-butenyl isothiocyanate from Raphanus sativus L. (Kaiware Daikon) Sprouts. J. Agric. Food Chem. 56 (2008) 7823-7830
45. Prives C., and Hall P.A. The p53 pathway. J. Pathol. 187 (1999) 112-126
46. Sapone A., Affatato A., Canistro D., Pozzetti L., Broccoli M., Barillari J., Iori R., and Paolini M. Cruciferous vegetables and lung cancer. Mutat. Res. 635 (2006) 146-148
47. Shieh S.Y., Ikeda M., Taya Y., and Prives C. DNA damage-induced phosphorylation of p53 alleviates inhibition by MDM2. Cell 91 (1997) 325-334
48. Spitz M.R., Duphorne C.M., Detry M.A., Pillow P.C., Amos C.I., Lei L., de Andrade M., Gu X., Hong W.K., and Wu X. Dietary intake of isothiocyanates: evidence of a joint effect with glutathione S-transferase polymorphisms in lung cancer risk. Cancer Epidemiol. Biomark. Prev. 9 (2000) 1017-1020
49. Talalay P., and Fahey J.W. Phytochemicals from cruciferous plants protect against cancer by modulating carcinogen metabolism. J. Nutr. 131 (2001) 3027S-3033S
50. Tang L., Zirpoli G.R., Guru K., Moysich K.B., Zhang Y., Ambrosone C.B., and McCann S.E. Consumption of raw cruciferous vegetables is inversely associated with bladder cancer risk. Cancer Epidemiol. Biomark. Prev. 17 (2008) 938-944
51. Thejass P., and Kuttan G. Antimetastatic activity of sulforaphane. Life Sci. 78 (2006) 3043-3050
52. Thomson C.A., Rock C.L., Caan B.J., Flatt S.W., Al-Delaimy W.A., Newman V.A., Hajek R.A., Chilton J.A., and Pierce J.P. Increase in cruciferous vegetable intake in women previously treated for breast cancer participating in a dietary intervention trial. Nutr. Cancer 57 (2007) 11-19
53. Tibbetts R.S., Brumbaugh K.M., Williams J.M., Sarkaria J.N., Cliby W.A., Shieh S.Y., Taya Y., Prives C., and Abraham R.T. A role for ATR in the DNA damage-induced phosphorylation of p53. Genes Dev. 13 (1999) 152-157
54. van Poppel G., Verhoeven D.T., Verhagen H., and Goldbohm R.A. Brassica vegetables and cancer prevention. Epidemiology and mechanisms. Adv. Exp. Med. Biol. 472 (1999) 159-168
55. Vousden K.H., and Lu X. Live or let die: the cell's response to p53. Nat. Rev. Cancer 2 (2002) 594-604
56. 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.
57. Zhang Y., and Tang L. Discovery and development of sulforaphane as a cancer chemopreventive phytochemical. Acta Pharmacol. Sin. 28 (2007) 1343-1354
58. Zhang Y., Yao S., and Li J. Vegetable-derived isothiocyanates: anti-proliferative activity and mechanism of action. Proc. Nutr. Soc. 65 (2006) 68-75