Suppressed Sex Hormone Biosynthesis by Alkylresorcinols: A Possible Link to Chemoprevention

References

• Sawada N, Iwasaki M, Yamaji T, Shimazu T, Sasazuki S, et al.: Fiber intake and risk of subsequent prostate cancer in Japanese men. Am J Clin Nutr 101, 118–125, 2015. doi: 10.3945/ajcn.114.089581
   PubMed Web of Science ®Google Scholar
• Adlercreutz H: Can rye intake decrease risk of human breast cancer? Food Nutr Res 54, 2010. doi: 10.3402/fnr.v54i0.5231
   PubMed Web of Science ®Google Scholar
• Deschasaux M, Pouchieu C, His M, Hercberg S, Latino-Martel P, et al.: Dietary total and insoluble fiber intakes are inversely associated with prostate cancer risk. J Nutr 144, 504–510, 2014. doi: 10.3945/jn.113.189670
   PubMed Web of Science ®Google Scholar
• Aune D, Chan DS, Greenwood DC, Vieira AR, Rosenblatt DA, et al.: Dietary fiber and breast cancer risk: a systematic review and meta-analysis of prospective studies. Ann Oncol 23, 1394–1402, 2012. doi: 10.1093/annonc/mdr589
   PubMed Web of Science ®Google Scholar
• Fardet A: New hypotheses for the health-protective mechanisms of whole-grain cereals: what is beyond fibre? Nutr Res Rev 23, 65–134, 2010. doi: 10.1017/S0954422410000041
   PubMed Web of Science ®Google Scholar
• Bartłomiej S, Justyna RK, and Ewa N: Bioactive compounds in cereal grains - occurrence, structure, technological significance and nutritional benefits - a review. Food Sci Technol Int 18, 559–568, 2012. doi: 10.1177/1082013211433079
   PubMed Web of Science ®Google Scholar
• McCann MJ, Gill CI, McGlynn H, and Rowland IR: Role of mammalian lignans in the prevention and treatment of prostate cancer. Nutr Cancer 52, 1–14, 2005. doi: 10.1207/s15327914nc5201_1
   PubMed Web of Science ®Google Scholar
• Slavin J: Why whole grains are protective: biological mechanisms. Proc Nutr Soc 62, 129–134, 2003. doi: 10.1079/PNS2002221
   PubMed Web of Science ®Google Scholar
• Stasiuk M and Kozubek A: Biological activity of phenolic lipids. Cell Mol Life Sci 67, 841–860, 2010. doi: 10.1007/s00018-009-0193-1
   PubMed Web of Science ®Google Scholar
• Ross AB, Kamal-Eldin A, and Aman P: Dietary alkylresorcinols: Absorption, bioactivities, and possible use as biomarkers of whole-grain wheat- and rye-rich foods. Nutr Rev 62, 81–95, 2004. doi: 10.1301/nr.2004.mar.81-95
   PubMed Web of Science ®Google Scholar
• Bondia-Pons I, Aura AM, Vuorela S, Kolehmainen M, Mykkanen H, et al.: Rye phenolics in nutrition and health. J Cereal Sci 49, 323–336, 2009. doi: 10.1016/j.jcs.2009.01.007
   Web of Science ®Google Scholar
• Ross AB, Kamal-Eldin A, Lundin EA, Zhang JX, Hallmans G, et al.: Cereal alkylresorcinols are absorbed by humans. J Nutr 133, 2222–2224, 2003.
   PubMed Web of Science ®Google Scholar
• Ross AB, Chen Y, Frank J, Swanson JE, Parker RS, et al.: Cereal alkylresorcinols elevate gamma-tocopherol levels in rats and inhibit gamma-tocopherol metabolism in vitro. J Nutr 134, 506–510, 2004.
   PubMed Web of Science ®Google Scholar
• Ross AB, Bourgeois A, Macharia HN, Kochhar S, Jebb SA, et al.: Plasma alkylresorcinols as a biomarker of whole-grain food consumption in a large population: results from the WHOLEheart Intervention Study. Am J Clin Nutr 95, 204–211, 2012. doi: 10.3945/ajcn.110.008508
   PubMed Web of Science ®Google Scholar
• Ross AB: Present status and perspectives on the use of alkylresorcinols as biomarkers of wholegrain wheat and rye intake. J Nutr Metab 2012, 462967, 2012. doi: 10.1155/2012/462967
   PubMedGoogle Scholar
• Kyro C, Olsen A, Landberg R, Skeie G, Loft S, et al.: Plasma alkylresorcinols, biomarkers of whole-grain wheat and rye intake, and incidence of colorectal cancer. J Natl Cancer Inst 106, djt352, 2014. doi: 10.1093/jnci/djt352
   PubMedGoogle Scholar
• Aubertin-Leheudre M, Koskela A, Samaletdin A, and Adlercreutz H: Plasma and urinary alkylresorcinol metabolites as potential biomarkers of breast cancer risk in Finnish women: a pilot study. Nutr Cancer 62, 759–764, 2010. doi: Pii 924625640 10.1080/01635581003693058
   PubMed Web of Science ®Google Scholar
• Meija L, Krams I, Cauce V, Samaletdin A, Soderholm P, et al.: Alkylresorcinol metabolites in urine and plasma as potential biomarkers of rye and wheat fiber consumption in prostate cancer patients and controls. Nutr Cancer 67, 258–265, 2015. doi: 10.1080/01635581.2015.989371
   PubMed Web of Science ®Google Scholar
• Kyro C, Olsen A, Bueno-de-Mesquita HB, Skeie G, Loft S, et al.: Plasma alkylresorcinol concentrations, biomarkers of whole-grain wheat and rye intake, in the European Prospective Investigation into Cancer and Nutrition (EPIC) cohort. Br J Nutr 111, 1881–1890, 2014. doi: 10.1017/S0007114513004388
   PubMed Web of Science ®Google Scholar
• Gliwa J, Gunenc A, Ames N, Willmore WG, and Hosseinian FS: Antioxidant activity of alkylresorcinols from rye bran and their protective effects on cell viability of PC-12 AC cells. J Agric Food Chem 59, 11473–11482, 2011. doi: 10.1021/jf2023353
   PubMed Web of Science ®Google Scholar
• Parikka K, Rowland IR, Welch RW, and Wahala K: In vitro antioxidant activity and antigenotoxicity of 5-n-alkylresorcinols. J Agric Food Chem 54, 1646–1650, 2006. doi: 10.1021/jf052486e
   PubMed Web of Science ®Google Scholar
• Rainey WE, Bird IM, and Mason JI: The NCI-H295 cell line: a pluripotent model for human adrenocortical studies. Mol Cell Endocrinol 100, 45–50, 1994.
   PubMed Web of Science ®Google Scholar
• Oskarsson A, Ulleras E, Plant KE, Hinson JP, and Goldfarb PS: Steroidogenic gene expression in H295R cells and the human adrenal gland: adrenotoxic effects of lindane in vitro. J Appl Toxicol 26, 484–492, 2006. doi: 10.1002/jat.1166
   PubMed Web of Science ®Google Scholar
• Ulleras E, Ohlsson A, and Oskarsson A: Secretion of cortisol and aldosterone as a vulnerable target for adrenal endocrine disruption - screening of 30 selected chemicals in the human H295R cell model. J Appl Toxicol 28, 1045–1053, 2008. doi: 10.1002/jat.1371
   PubMed Web of Science ®Google Scholar
• Ohlsson A, Ulleras E, Cedergreen N, and Oskarsson A: Mixture effects of dietary flavonoids on steroid hormone synthesis in the human adrenocortical H295R cell line. Food Chem Toxicol 48, 3194–3200, 2010. doi: 10.1016/j.fct.2010.08.021
   PubMed Web of Science ®Google Scholar
• OECD: OECD Guideline for the testing of chemicals. Test no #456: H295R steroidogenesis assay., 2011.
   Google Scholar
• Kozubek A and Tyman JH: Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biological activity. Chem Rev 99, 1–26, 1999.
   PubMed Web of Science ®Google Scholar
• Stasiuk M, Kozubek A: Membrane perturbing properties of natural phenolic and resorcinolic lipids. FEBS Lett 582, 3607–3613, 2008. doi: 10.1016/j.febslet.2008.09.039
   PubMed Web of Science ®Google Scholar
• Kozubek A: The effect of 5-(n-alk(en)yl)resorcinols on membranes. II. Dependence of the aliphatic chain length and unsaturation. Acta Biochimica Polonica 34, 387–394, 1987.
   PubMed Web of Science ®Google Scholar
• Kozubek A and Demel RA: The effect of 5-(n-alk(en)yl) resorcinols from rye on membrane structure. Biochimica et Biophysica Acta 642, 242–251, 1981.
   PubMed Web of Science ®Google Scholar
• Kozubek A and Demel RA: Permeability changes of erythrocytes and liposomes by 5-(n-alk(en)yl) resorcinols from rye. Biochimica et Biophysica Acta 603, 220–227, 1980.
   PubMed Web of Science ®Google Scholar
• Linko-Parvinen AM, Landberg R, Tikkanen MJ, Adlercreutz H, and Penalvo JL: Alkylresorcinols from whole-grain wheat and rye are transported in human plasma lipoproteins. J Nutr 137, 1137–1142, 2007.
   PubMed Web of Science ®Google Scholar
• Nakajin S, Shinoda S, Ohno S, Nakazawa H, and Makino T: Effect of phthalate esters and alkylphenols on steroidogenesis in human adrenocortical H295R cells. Environ Toxicol Pharmacol 10, 103–110, 2001.
   PubMed Web of Science ®Google Scholar
• Han XD, Tu ZG, Gong Y, Shen SN, Wang XY, et al.: The toxic effects of nonylphenol on the reproductive system of male rats. Reprod Toxicol 19, 215–221, 2004. doi: 10.1016/j.reprotox.2004.06.014
   PubMed Web of Science ®Google Scholar
• Wu JJ, Wang KL, Wang SW, Hwang GS, Mao IF, et al.: Differential effects of nonylphenol on testosterone secretion in rat Leydig cells. Toxicology 268, 1–7, 2010. doi: 10.1016/j.tox.2009.10.030
   PubMed Web of Science ®Google Scholar
• Laurenzana EM, Balasubramanian G, Weis C, Blaydes B, Newbold RR, et al.: Effect of nonylphenol on serum testosterone levels and testicular steroidogenic enzyme activity in neonatal, pubertal, and adult rats. Chem Biol Interact 139, 23–41, 2002.
   PubMed Web of Science ®Google Scholar
• Vasaitis TS, Bruno RD, and Njar VC: CYP17 inhibitors for prostate cancer therapy. J Steroid Biochem Mol Biol 125, 23–31, 2011. doi: 10.1016/j.jsbmb.2010.11.005
   PubMed Web of Science ®Google Scholar
• Zhu H and Garcia JA: Targeting the adrenal gland in castration-resistant prostate cancer: a case for orteronel, a selective CYP-17 17,20-lyase inhibitor. Curr Oncol Rep 15, 105–112, 2013. doi: 10.1007/s11912-013-0300-1
   PubMed Web of Science ®Google Scholar
• Oskarsson A, Spatafora C, Tringali C, Andersson AO: Inhibition of CYP17A1 activity by resveratrol, piceatannol, and synthetic resveratrol analogs. Prostate 74, 839–851, 2014. doi: 10.1002/pros.22801
   PubMed Web of Science ®Google Scholar
• Dias SJ, Li K, Rimando AM, Dhar S, Mizuno CS, et al.: Trimethoxy-resveratrol and piceatannol administered orally suppress and inhibit tumor formation and growth in prostate cancer xenografts. Prostate 73, 1135–1146, 2013. doi: 10.1002/pros.22657
   PubMed Web of Science ®Google Scholar
• Bylund A, Zhang JX, Bergh A, Damber JE, Widmark A, et al.: Rye bran and soy protein delay growth and increase apoptosis of human LNCaP prostate adenocarcinoma in nude mice. Prostate 42, 304–314, 2000.
   PubMed Web of Science ®Google Scholar
• Torfadottir JE, Valdimarsdottir UA, Mucci L, Stampfer M, Kasperzyk JL, et al.: Rye bread consumption in early life and reduced risk of advanced prostate cancer. Cancer Causes & Control 23, 941–950, 2012. doi: 10.1007/s10552-012-9965-2
   PubMed Web of Science ®Google Scholar
• Drake I, Sonestedt E, Gullberg B, Bjartell A, Olsson H, et al.: Plasma alkylresorcinol metabolites as biomarkers for whole-grain intake and their association with prostate cancer: a Swedish nested case-control study. Cancer Epidemiol Biomarkers Prev 23, 73–83, 2014. doi: 10.1158/1055-9965.EPI-13-0878
   PubMed Web of Science ®Google Scholar
• Landberg R, Andersson SO, Zhang JX, Johansson JE, Stenman UH, et al.: Rye whole grain and bran intake compared with refined wheat decreases urinary C-peptide, plasma insulin, and prostate specific antigen in men with prostate cancer. J Nutr 140, 2180–2186, 2010. doi: 10.3945/jn.110.127688
   PubMed Web of Science ®Google Scholar
• Subramanian A, Salhab M, and Mokbel K: Oestrogen producing enzymes and mammary carcinogenesis: a review. Breast Cancer Res Treat 111, 191–202, 2008. doi: 10.1007/s10549-007-9788-0
   PubMed Web of Science ®Google Scholar
• Sanderson JT, Hordijk J, Denison MS, Springsteel MF, Nantz MH, et al.: Induction and inhibition of aromatase (CYP19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells. Toxicol Sci 82, 70–79, 2004. doi: 10.1093/toxsci/kfh257
   PubMed Web of Science ®Google Scholar
• Aubertin-Leheudre M, Hamalainen E, and Adlercreutz H: Diets and hormonal levels in postmenopausal women with or without breast cancer. Nutr Cancer 63, 514–524, 2011. doi: 10.1080/01635581.2011.538487
   PubMed Web of Science ®Google Scholar
• Adlercreutz H, Hamalainen E, Gorbach SL, Goldin BR, Woods MN, et al.: Diet and plasma androgens in postmenopausal vegetarian and omnivorous women and postmenopausal women with breast cancer. Am J Clin Nutr 49, 433–442, 1989.
   PubMed Web of Science ®Google Scholar
• Rose DP, Lubin M, and Connolly JM: Effects of diet supplementation with wheat bran on serum estrogen levels in the follicular and luteal phases of the menstrual cycle. Nutrition 13, 535–529, 1997.
   PubMed Web of Science ®Google Scholar
• Ferrari P, Rinaldi S, Jenab M, Lukanova A, Olsen A, et al.: Dietary fiber intake and risk of hormonal receptor-defined breast cancer in the European Prospective Investigation into Cancer and Nutrition study. Am J Clin Nutr 97, 344–353, 2013. doi: 10.3945/ajcn.112.034025
   PubMed Web of Science ®Google Scholar
• Linko AM, Parikka K, Wahala K, and Adlercreutz H: Gas chromatographic-mass spectrometric method for the determination of alkylresorcinols in human plasma. Anal Biochem 308, 307–313, 2002.
   PubMed Web of Science ®Google Scholar
• Linko AM, Juntunen KS, Mykkanen HM, Adlercreutz H: Whole-grain rye bread consumption by women correlates with plasma alkylresorcinols and increases their concentration compared with low-fiber wheat bread. J Nutr 135, 580–583, 2005.
   PubMed Web of Science ®Google Scholar
• Landberg R, Kamal-Eldin A, Andersson A, Vessby B, and Aman P: Alkylresorcinols as biomarkers of whole-grain wheat and rye intake: plasma concentration and intake estimated from dietary records. Am J Clin Nutr 87, 832–838, 2008.
   PubMed Web of Science ®Google Scholar
• Landberg R, Aman P, Friberg LE, Vessby B, Adlercreutz H, et al.: Dose response of whole-grain biomarkers: alkylresorcinols in human plasma and their metabolites in urine in relation to intake. Am J Clin Nutr 89, 290–296, 2009. doi: 10.3945/ajcn.2008.26709
   PubMed Web of Science ®Google Scholar
• Landberg R, Linko AM, Kamal-Eldin A, Vessby B, Adlercreutz H, et al.: Human plasma kinetics and relative bioavailability of alkylresorcinols after intake of rye bran. J Nutr 136, 2760–2765, 2006.
   PubMed Web of Science ®Google Scholar
• Jansson E, Landberg R, Kamal-Eldin A, Wolk A, Vessby B, et al.: Presence of alkylresorcinols, potential whole grain biomarkers, in human adipose tissue. Br J Nutr 104, 633–636, 2010. doi: 10.1017/S0007114510001169
   PubMed Web of Science ®Google Scholar