Oxyphytosterols as active ingredients in wheat bran suppress human colon cancer cell growth: Identification, chemical synthesis, and biological evaluation

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 8, 2015, Pages 2267-2276

  Zhu, Yingdong ^a   Soroka, Dominique ^a   Sang, Shengmin ^a  

^a NORTH CAROLINA A AND T STATE UNIVERSITY   (United States)

Author keywords

apoptosis; chemical synthesis; colon cancer; cytotoxicity; sterol oxide; wheat bran

Indexed keywords

ALCOHOLS; CELL DEATH; CHROMATOGRAPHY; CYTOLOGY; CYTOTOXICITY; DISEASES; ELECTROSPRAY IONIZATION; GRAIN (AGRICULTURAL PRODUCT); IONIZATION OF LIQUIDS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SYNTHESIS (CHEMICAL);

ANTIPROLIFERATIVE EFFECT; ANTIPROLIFERATIVE PROPERTIES; APOPTOSIS PATHWAYS; BIOLOGICAL EVALUATION; COLON CANCER; HUMAN COLON CANCER CELLS; LIQUID CHROMATOGRAPHY - MASS SPECTROMETRIES; WHEAT BRAN;

CELLS;

TRITICUM AESTIVUM;

ANTINEOPLASTIC AGENT; PHYTOSTEROL; PLANT EXTRACT;

ANALYSIS; APOPTOSIS; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; COLON TUMOR; DIETARY FIBER; DRUG EFFECTS; HCT116 CELL LINE; HT 29 CELL LINE; HUMAN; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; PATHOPHYSIOLOGY; SYNTHESIS;

ANTICARCINOGENIC AGENTS; APOPTOSIS; CELL PROLIFERATION; COLONIC NEOPLASMS; DIETARY FIBER; HCT116 CELLS; HT29 CELLS; HUMANS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PHYTOSTEROLS; PLANT EXTRACTS;

EID: 84924255814     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf506361r     Document Type: Article

References (43)

1. Aune, D.; Norat, T.; Romundstad, P.; Vatten, L. J. Whole grain and refined grain consumption and the risk of type 2 diabetes: a systematic review and dose-response meta-analysis of cohort studies Eur. J. Epidemiol. 2013, 28, 845-858
2. Lillioja, S.; Neal, A. L.; Tapsell, L.; Jacobs, D. R., Jr. Whole grains, type 2 diabetes, coronary heart disease, and hypertension: Links to the aleurone preferred over indigestible fiber Biofactors 2013, 39, 242-258
3. Ochoa-Aviles, A.; Verstraeten, R.; Lachat, C.; Andrade, S.; Van Camp, J.; Donoso, S.; Kolsteren, P. Dietary intake practices associated with cardiovascular risk in urban and rural Ecuadorian adolescents: A cross-sectional study BMC Public Health 2014, 14, 939
4. Ortiz-Martinez, M.; Winkler, R.; Garcia-Lara, S. Preventive and therapeutic potential of peptides from cereals against cancer J. Proteomics 2014, 111C, 165-183
5. Kyro, C.; Skeie, G.; Loft, S.; Landberg, R.; Christensen, J.; Lund, E.; Nilsson, L. M.; Palmqvist, R.; Tjonneland, A.; Olsen, A. Intake of whole grains from different cereal and food sources and incidence of colorectal cancer in the Scandinavian HELGA cohort Cancer, Causes Control 2013, 24, 1363-1374
6. Aune, D.; Chan, D. S.; Lau, R.; Vieira, R.; Greenwood, D. C.; Kampman, E.; Norat, T. Dietary fibre, whole grains, and risk of colorectal cancer: Systematic review and dose-response meta-analysis of prospective studies BMJ (Br. Med. J.) 2011, 343, d6617
7. World Cancer Research Fund/American Institute for Cancer Research. Continuous Update Project Report. Food, Nutrition, Physical Activity and the Prevention of Colorectal Cancer; 2011.
8. Slavin, J. Why whole grains are protective: Biological mechanisms Proc. Nutr. Soc. 2003, 62, 129-134
9. Reddy, B. S.; Hirose, Y.; Cohen, L. A.; Simi, B.; Cooma, I.; Rao, C. V. Preventive potential of wheat bran fractions against experimental colon carcinogenesis: implications for human colon cancer prevention Cancer Res. 2000, 60, 4792-4797
10. Sang, S.; Ju, J.; Lambert, J. D.; Lin, Y.; Hong, J.; Bose, M.; Wang, S.; Bai, N.; He, K.; Reddy, B. S.; Ho, C. T.; Li, F.; Yang, C. S. Wheat bran oil and its fractions inhibit human colon cancer cell growth and intestinal tumorigenesis in Apc(min/+) mice J. Agric. Food Chem. 2006, 54, 9792-9797
11. Zhu, Y.; Conklin, D. R.; Chen, H.; Wang, L.; Sang, S. 5-Alk(en)ylresorcinols as the major active components in wheat bran inhibit human colon cancer cell growth Bioorg. Med. Chem. 2011, 19, 3973-3982
12. Zhu, Y.; Soroka, D. N.; Sang, S. Structure elucidation and chemical profile of sphingolipids in wheat bran and their cytotoxic effects against human colon cancer cells J. Agric. Food Chem. 2013, 61, 866-874
13. Lagarda, M. J.; Garcia-Llatas, G.; Farre, R. Analysis of phytosterols in foods J. Pharm. Biomed. Anal. 2006, 41, 1486-1496
14. AbuMweis, S. S.; Jones, P. J. Cholesterol-lowering effect of plant sterols Curr. Atheroscler. Rep. 2008, 10, 467-472
15. Grattan, B. J., Jr. Plant sterols as anticancer nutrients: Evidence for their role in breast cancer Nutrients 2013, 5, 359-387
16. Moghadasian, M. H.; McManus, B. M.; Godin, D. V.; Rodrigues, B.; Frohlich, J. J. Proatherogenic and antiatherogenic effects of probucol and phytosterols in apolipoprotein E-deficient mice: Possible mechanisms of action Circulation 1999, 99, 1733-1739
17. Bouic, P. J. The role of phytosterols and phytosterolins in immune modulation: a review of the past 10 years Curr. Opin. Clin. Nutr. Metab. Care 2001, 4, 471-475
18. Nourooz-Zadeh, J.; Appelqvist, L. Isolation and quantitative determination of sterol oxides in plant-based foods: Soybean oil and wheat flour J. Am. Oil Chem. Soc. 1992, 69, 288-293
19. Iwatsuki, K.; Akihisa, T.; Tokuda, H.; Ukiya, M.; Higashihara, H.; Mukainaka, T.; Iizuka, M.; Hayashi, Y.; Kimura, Y.; Nishino, H. Sterol ferulates, sterols, and 5-alk(en)ylresorcinols from wheat, rye, and corn bran oils and their inhibitory effects on Epstein-Barr virus activation J. Agric. Food Chem. 2003, 51, 6683-6688
20. Prinsen, P.; Gutierrez, A.; Faulds, C. B.; del Rio, J. C. Comprehensive study of valuable lipophilic phytochemicals in wheat bran J. Agric. Food Chem. 2014, 62, 1664-1673
21. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays J. Immunol. Methods 1983, 65, 55-63
22. Kontiza, I.; Abatis, D.; Malakate, K.; Vagias, C.; Roussis, V. 3-Keto steroids from the marine organisms Dendrophyllia cornigera and Cymodocea nodosa Steroids 2006, 71, 177-181
23. Monteiro Gaspar, E. M. M. S.; Chaves Das Neves, H. J. Unusual steroids in allelopathic extracts of wheat straw Proc.-Plant Growth Regul. Soc. Am. 1995, 22, 78-80
24. Notaro, G.; Piccialli, V.; Sica, D. New steroidal hydroxyketones and closely related diols from the marine sponge Cliona copiosa J. Nat. Prod. 1992, 55, 1588-1594
25. Foley, D. A.; OCallaghan, Y.; OBrien, N. M.; McCarthy, F. O.; Maguire, A. R. Synthesis and characterization of stigmasterol oxidation products J. Agric. Food Chem. 2010, 58, 1165-1173
26. McCarthy, F. O.; Chopra, J.; Ford, A.; Hogan, S. A.; Kerry, J. P.; OBrien, N. M.; Ryan, E.; Maguire, A. R. Synthesis, isolation and characterisation of beta-sitosterol and beta-sitosterol oxide derivatives Org. Biomol. Chem. 2005, 3, 3059-3065
27. Xie, W.; Peng, H.; Kim, D. I.; Kunkel, M.; Powis, G.; Zalkow, L. H. Structure-activity relationship of aza-steroids as PI-PLC inhibitors Bioorg. Med. Chem. 2001, 9, 1073-1083
28. Jiang, X.; Ory, D. S.; Han, X. Characterization of oxysterols by electrospray ionization tandem mass spectrometry after one-step derivatization with dimethylglycine Rapid Commun. Mass Spectrom. 2007, 21, 141-152
29. Gao, J.; Yue, Q.; Ji, Y.; Cheng, B.; Zhang, X. Novel synthesis strategy for the preparation of individual phytosterol oxides J. Agric. Food Chem. 2013, 61, 982-988
30. del Rio, J. C.; Prinsen, P.; Gutierrez, A. A comprehensive characterization of lipids in wheat straw J. Agric. Food Chem. 2013, 61, 1904-1913
31. Allevi, P.; Anastasia, M.; Colombo, D.; Fiecchi, A. Hydroboration of 5 alpha-ergost-8-en-3 beta-ol Steroids 1989, 54, 133-143
32. Fang, J. M.; Wang, K. C.; Cheng, Y. S. Steroids and triterpenoids from Rosa laevigata Phytochemistry 1991, 30, 3383-3387
33. Garcia-Llatas, G.; Rodriguez-Estrada, M. T. Current and new insights on phytosterol oxides in plant sterol-enriched food Chem. Phys. Lipids 2011, 164, 607-624
34. Johnson, D. F.; Bennett, R. D.; Heftmann, E. Cholesterol in higher plants Science 1963, 140, 198-199
35. Behrman, E. J.; Gopalan, V. Cholesterol and plants J. Chem. Educ. 2005, 82, 1791-1793
36. Smith, L. L. Review of progress in sterol oxidations: 1987-1995 Lipids 1996, 31, 453-487
37. Smith, L. L. Cholesterol autoxidation 1981-1986 Chem. Phys. Lipids 1987, 44, 87-125
38. Schroepfer, G. J., Jr. Oxysterols: Modulators of cholesterol metabolism and other processes Physiol. Rev. 2000, 80, 361-554
39. Hovenkamp, E.; Demonty, I.; Plat, J.; Lutjohann, D.; Mensink, R. P.; Trautwein, E. A. Biological effects of oxidized phytosterols: A review of the current knowledge Prog. Lipid Res. 2008, 47, 37-49
40. Chan, Y. M.; Varady, K. A.; Lin, Y.; Trautwein, E.; Mensink, R. P.; Plat, J.; Jones, P. J. Plasma concentrations of plant sterols: Physiology and relationship with coronary heart disease Nutr. Rev. 2006, 64, 385-402
41. Tomoyori, H.; Kawata, Y.; Higuchi, T.; Ichi, I.; Sato, H.; Sato, M.; Ikeda, I.; Imaizumi, K. Phytosterol oxidation products are absorbed in the intestinal lymphatics in rats but do not accelerate atherosclerosis in apolipoprotein E-deficient mice J. Nutr. 2004, 134, 1690-1696
42. Grandgirard, A.; Sergiel, J. P.; Nour, M.; Demaison-Meloche, J.; Ginies, C. Lymphatic absorption of phytosterol oxides in rats Lipids 1999, 34, 563-570
43. Xie, W.; Peng, H.; Zalkow, L. H.; Li, Y. H.; Zhu, C.; Powis, G.; Kunkel, M. 3Beta-hydroxy-6-aza-cholestane and related analogues as phosphatidylinositol specific phospholipase C (PI-PLC) inhibitors with antitumor activity Bioorg. Med. Chem. 2000, 8, 699-706