Dietary Phenols: Antioxidants for the Brain?

References

• Adlercreutz, H., Bannwart, C., Wahala, K., Makela, T., Brunow, G., Hase, T., Arosemena, P.J., Kellis, J.T. and Vickery, L.E. (1993) Inhibition of human aromatase by mammalian lignans and isoflavonoid phytoestrogens. Journal of Steroid Biochemistry and Molecular Biology 44, 147–153.
   PubMed Web of Science ®Google Scholar
• Agullo, G., Gamet-Payrastre, L., Manenti, S., Viala, S., Remsey, C., Chap, H. and Payastre, B. (1997) Relationship between flavonoid structure and inhibition of phosphatidylinositol 3-kinase: a comparison with tyrosine kinase and protein kinase C inhibition. Biochemical Pharmacology 53, 1649–1657.
   PubMed Web of Science ®Google Scholar
• Akiyama, T., Ishida, J., Nakagawa, S., Ogawara, H., Watanabe, S., Itoh, N., Shibuya, M. and Fukami, Y. (1987) Genistein, a specific inhibitor of tyrosine-specific protein kinases. Journal of Biological Chemistry 262, 5592–5595.
   PubMed Web of Science ®Google Scholar
• Ames, B.N. (1983) Dietary carcinogens and anticarcinogens. Oxygen radicals and degenerative diseases. Science 221, 1256–1264.
   PubMed Web of Science ®Google Scholar
• Arouma, O.I., Evans, P.J., Kaur, H., Sutcliffe, L. and Halliwell, B. (1990) An evaluation of the antioxidant and potential pro-oxidant properties of food additives and of trolox C, vitamin E and probucol. Free Radical Research Communications 10, 143–157.
   PubMedGoogle Scholar
• Beal, M.F. (1995) Aging, energy, and oxidative stress in neurodegenerative disorders. Annals of Neurology 38, 357–366.
   PubMed Web of Science ®Google Scholar
• Beckman, K.B. and Ames, B.N. (1998) The free radical theory of aging matures. Physiological Reviews 78, 547–581.
   PubMed Web of Science ®Google Scholar
• Behl, C., Davies, J., Cole, G.M. and Schubert, D. (1992) Vitamin E protects nerve cells from amyloid β protein toxicity. Biochemical and Biophysical Research Communications 186, 944–950.
   PubMed Web of Science ®Google Scholar
• Behl, C., Davies, J.B., Lesley, R. and Schubert, D. (1994) Hydrogen peroxide mediates amyloid β protein toxicity. Cell 77, 817–827.
   PubMed Web of Science ®Google Scholar
• Behl, C., Widmann, M., Trapp, T. and Holsboer, F. (1995) 17-β estradiol protects neurons from oxidative stress-induced cell death in vitro. Biochemical and Biophysical Research Communications 216, 473–482.
   PubMed Web of Science ®Google Scholar
• Behl, C., Skutella, T., Lezoualc'h, F., Post, A., Widmann, M., Newton, C. and Holsboer, F. (1997) Neuroprotection against oxidative stress by estrogens: structure-activity relationship. Molecular Pharmacology 51, 535–541.
   PubMed Web of Science ®Google Scholar
• Behl, C. (1999) Alzheimer's disease and oxidative stress: implications for novel therapeutic approaches. Progress in Neurobiology 57, 301–323.
   PubMed Web of Science ®Google Scholar
• Behl, C. and Moosmann, B. (1999) Estrogen and other antioxidants in neuroprotection: relevance to Alzheimer's disease. In: Poli, Packer and Cadenas (Eds.), Free Radicals in Brain Pathophysiology (New York: Dekker Publications).
   Google Scholar
• Bravo, L. (1998) Polyphenols: chemistry, dietary sources, metabolism and nutritional significance. Nutrition Reviews 56, 317–333.
   PubMed Web of Science ®Google Scholar
• Burton, G.W., Joyce, A. and Ingold, K.U. (1983) Is vitamin E the only lipid-soluble, chain-breaking antioxidant in human blood plasma and erythrocyte membranes? Archives of Biochemistry and Biophysics 221, 281–290.
   PubMed Web of Science ®Google Scholar
• Canada, A.T., Gianella, E., Nguyen, T.D. and Mason, R.P. (1990) The production of reactive oxygen species by dietary flavonols. Free Radical Biology and Medicine 9, 441–449.
   PubMed Web of Science ®Google Scholar
• Christen, S., Woodall, A.A., Shigenaga, M.K., Southwell-Keely, P.T., Duncan, M.W. and Ames, B.N. (1997) γ-Tocopherol traps mutagenic electrophiles such as NOx and complements α-tocopherol: physiological implications. Proceedings of the National Academy of Sciences of the United States of America 94, 3217–3222.
   PubMed Web of Science ®Google Scholar
• Ciolino, H.P., Daschner, P.J. and Yeh, G.C. (1998) Resveratrol inhibits transcription of CYP1A1 in vitro by preventing activation of the aryl hydrocarbon receptor. Cancer Research 58, 5707–5712.
   PubMed Web of Science ®Google Scholar
• Clement, M.V., Hirpara, J.L., Chawdhury, S.H. and Pervaiz, S. (1998) Chemopreventive agent resveratrol, a natural product derived from grapes, triggers CD95 signaling-dependent apoptosis in human tumor cells. Blood 92, 996–1002.
   PubMed Web of Science ®Google Scholar
• Colditz, G.A. (1998) Relationship between estrogen levels, use of hormone replacement therapy, and breast cancer. Journal of the National Cancer Institute 90, 814–823.
   PubMed Web of Science ®Google Scholar
• Coyle, J.T. and Puttfarcken, P. (1993) Oxidative stress, glutamate, and neurodegenerative disorders. Science 262, 689–694.
   PubMed Web of Science ®Google Scholar
• Cynshi, O., Kawabe, Y, Suzuki, T., Takashima, Y., Kaise, H., Nakamura, M., Ohba, Y., Kato, Y, Tamura, K., Hayasaka, A. et al. (1998) Antiatherogenic effects of the antioxidant BO-653 in three different animal models. Proceedings of the National Academy of Sciences of the United States of America 95, 10123–10128.
   PubMed Web of Science ®Google Scholar
• Das, N.P. (1971) Studies on flavonoid metabolism. Absorption and metabolism of (+)-catechin in man. Biochemical Pharmacology 20, 3435–3445.
   PubMed Web of Science ®Google Scholar
• de Vries, J.H., Janssen, K., Hollman, P.C., van Staveren, W.A. and Katan, M.B. (1997) Consumption of quercetin and kaempferol in free-living subjects eating a variety of diets. Cancer Letters 114, 141–144.
   PubMed Web of Science ®Google Scholar
• de Vries, J.H., Hollman, P.C., Meyboom, S., Buysman, M.N., Zock, P.L., van Staveren, W.A. and Katan, M.B. (1998) Plasma concentrations and urinary excretion of the antioxidant flavonols quercetin and kaempferol as biomarkers for dietary intake. American Journal of Clinical Nutrition 68, 60–65.
   PubMed Web of Science ®Google Scholar
• Dickancaite, E., Nemeikaite, A., Kalvelyte, A. and Cenas, N. (1998) Prooxidant character of flavonoid cytotoxicity: structure-activity relationships. Biochemistry and Molecular Biology International 45, 923–930.
   PubMedGoogle Scholar
• Dubal, D.B., Kashon, M.L., Pettigrew, L.C., Ren, J.M., Finklestein, S.P., Rau, S.W. and Wise, P.M. (1998) Estradiol protects against ischemic injury. Journal of Cerebral Blood Flow and Metabolism 18, 1253–1258.
   PubMed Web of Science ®Google Scholar
• Dunnick, J.K. and Hailey, J.R. (1992) Toxicity and carcinogenicity studies of quercetin, a natural component of foods. Fundamental and Applied Toxicology 19, 423–431.
   PubMedGoogle Scholar
• Ebadi, M., Srinivasan, S.K. and Baxi, M.D. (1996) Oxidative stress and antioxidant therapy in Parkinson's disease. Progress in Neurobiology 48, 1–19.
   PubMed Web of Science ®Google Scholar
• Esterbauer, H., Schaur, R.J. and Zollner, H. (1991) Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radical Biology and Medicine 11, 81–128.
   PubMed Web of Science ®Google Scholar
• Evans, B.A., Griffiths, K. and Morton, M.S. (1995) Inhibition of 5α-reductase in genital skin fibroblasts and prostate tissue by dietary lignans and isoflavonoids. Journal of Endocrinology 147, 295–302.
   PubMed Web of Science ®Google Scholar
• Fauconneau, B., Waffo-Teguo, P., Huguet, F., Barrier, L., Decendit, A. and Merillon, J.M. (1997) Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests. Life Sciences 61, 2103–2110.
   PubMed Web of Science ®Google Scholar
• Fotsis, T., Pepper, M., Adlercreutz, H., Fleischmann, G., Hase, T., Montesano, R. and Schweigerer, L. (1993) Genistein, a dietary-derived inhibitor of in vitro angiogenesis. Proceedings of the National Academy of Sciences of the United States of America 90, 2690–2694.
   PubMed Web of Science ®Google Scholar
• Green, P.S., Gordon, K. and Simpkins, J.W. (1997) Phenolic A ring requirement for the neuroprotective effects of steroids. Journal of Steroid Biochemistry and Molecular Biology 63, 229–235.
   PubMed Web of Science ®Google Scholar
• Gugler, R., Leschik, M. and Dengler, H.J. (1975) Disposition of quercetin in man after single oral and intravenous doses. European Journal of Clinical Pharmacology 9, 229–234.
   PubMed Web of Science ®Google Scholar
• Hampson, A.J., Grimaldi, M., Axelrod, J. and Wink, D. (1998) Cannabidiol and (-)δ9-tetrahydrocannabinol are neuroprotective antioxidants. Proceedings of the National Academy of Sciences of the United States of America 95, 8268–8273.
   PubMed Web of Science ®Google Scholar
• Harris, M.E., Hensley, K., Butterfield, D.A., Leedle, R.A. and Carney, J.M. (1995) Direct evidence of oxidative injury produced by the Alzheimer's β-amyloid peptide (1–40) in cultured hippocampal neurons. Experimental Neurology 131, 193–202.
   PubMed Web of Science ®Google Scholar
• Hollman, P.C., van Trijp, J.M., Mengelers, M.J., de Vries, J.H. and Katan, M.B. (1997) Bioavailability of the dietary antioxidant flavonol quercetin in man. Cancer Letters 114, 139–140.
   PubMed Web of Science ®Google Scholar
• Hollman, P.C. and Katan, M.B. (1998) Bioavailability and health effects of dietary flavonols in man. Archives of Toxicology 20(Suppl.), 237–248.
   Google Scholar
• Ji, X.D., Melman, N. and Jacobson, K.A. (1996) Interactions of flavonoids and other phytochemicals with adenosine receptors. Journal of Medicinal Chemistry 39, 781–788.
   PubMed Web of Science ®Google Scholar
• Kuiper, G.G.J.M., Lemmen, J.G., Carlsson, B., Corton, J.C., Safe, S.H., van der Saag, P.T., van der Burg, B. and Gustafsson, J.A. (1998) Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor β. Endocrinology 139, 4252–4263.
   PubMed Web of Science ®Google Scholar
• Kuppusamy, U.R., Khoo, H.E. and Das, N.P. (1990) Structure-activity studies of flavonoids as inhibitors of hyaluronidase. Biochemical Pharmacology 40, 397–401.
   PubMed Web of Science ®Google Scholar
• Leininger, B., Ghersi-Egea, J.F., Siest, G. and Minn, A. (1991) In vivo study of the elimination from rat brain of an intracerebrally formed xenobiotic metabolite, 1-naphthyl-β-D-glucuronide. Journal of Neurochemistry 56, 1163–1168.
   PubMed Web of Science ®Google Scholar
• Lezoualc'h, F., Sparapani, M. and Behl, C. (1998) N-acetyl-serotonin (normelatonin) and melatonin protect neurons against oxidative challenges and suppress the activity of the transcription factor NF-κB. Journal of Pineal Research 24, 168–178.
   PubMed Web of Science ®Google Scholar
• Liehr, J.G. (1997) Dual role of oestrogens as hormones and pro-carcinogens: tumor initiation by metabolic activation of oestrogens. European Journal of Cancer Prevention 6, 3–10.
   PubMed Web of Science ®Google Scholar
• Lien, E.J., Ren, S., Bui, H.H. and Wang, R. (1999) Quantitative structure-activity relationship analysis of phenolic antioxidants. Free Radical Biology and Medicine 26, 285–294.
   PubMed Web of Science ®Google Scholar
• Makela, S., Davis, V.L., Tally, W.C., Korkman, J., Salo, L., Vihko, R., Santti, R. and Korach, K.S. (1994) Dietary estrogens act through estrogen receptor-mediated processes and show no antiestrogenicity in cultured breast cancer cells. Environmental Health Perspectives 102, 572–578.
   PubMed Web of Science ®Google Scholar
• Moosmann, B., Uhr, M. and Behl, C. (1997) Neuroprotective potential of aromatic alcohols against oxidative cell death. FEBS Letters 413, 467–472.
   PubMed Web of Science ®Google Scholar
• Moosmann, B. and Behl, C. (1999) The antioxidant neuroprotective effects of estrogens and phenolic compounds are independent from their estrogenic properties. Proceedings of the National Academy of Sciences of the United States of America 96, 8867–8872.
   PubMed Web of Science ®Google Scholar
• Morton, M.S., Matos-Ferreira, A., Abranches-Monteiro, L., Correia, R., Blacklock, N., Chan, P.S., Cheng, C., Lloyd, S., Chieh-ping, W. and Griffiths, K. (1997) Measurement and metabolism of isoflavonoids and lignans in the human male. Cancer Letters 114, 145–151.
   PubMed Web of Science ®Google Scholar
• Murkies, A.L., Wilcox, G. and Davies, S.R. (1998) Phytoestrogens. Journal of Clinical Endocrinology and Metabolism 83, 297–303.
   PubMed Web of Science ®Google Scholar
• Ohshima, H., Yoshie, Y., Auriol, S. and Gilibert, I. (1998) Antioxidant and pro-oxidant actions of flavonoids: effects on DNA damage induced by nitric oxide, peroxynitrite and nitroxyl anion. Free Radical Biology and Medicine 25, 1057–1065.
   PubMed Web of Science ®Google Scholar
• Oldendorf, W.H. (1971) Brain uptake of radiolabeled amino acids, amines and hexoses after arterial injection. American Journal of Physiology 221, 1629–1639.
   PubMed Web of Science ®Google Scholar
• Oyama, Y., Fuchs, P.A., Katayama, N. and Noda, K. (1994) Myricetin and quercetin, the flavonoid constituents of Gingko biloba extract, greatly reduce oxidative metabolism in both resting and Ca2+-loaded brain neurons. Brain Research 635, 125–129.
   PubMed Web of Science ®Google Scholar
• Pardridge, W.M., Moeller, T.L., Mietus, L.J. and Oldendorf, W.H. (1980) Blood-brain barrier transport and brain sequestration of steroid hormones. American Journal of Physiology 239, E96–E102.
   PubMed Web of Science ®Google Scholar
• Rannug, U., Rannug, A., Sjoberg, U., Li, H., Westerholm, R. and Bergman, J. (1995) Structure elucidation of two tryptophan-derived, high affinity Ah receptor ligands. Chemistry and Biology 2, 841–845.
   PubMed Web of Science ®Google Scholar
• Reiter, R.J. (1998) Oxidative damage in the central nervous system: protection by melatonin. Progress in Neurobiology 56, 359–384.
   PubMed Web of Science ®Google Scholar
• Rendic, S. and Di Carlo, F.J. (1997) Human cytochrome P450 enzymes: a status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metabolism Reviews 29, 413–580.
   PubMed Web of Science ®Google Scholar
• Rogers, J., Cooper, N.R., Webster, S., Schultz, J., McGeer, P.L., Styren, S.D., Civin, W.H., Brachova, L., Bradt, B., Ward, P. et al. (1992) Complement activation by β-amyloid in Alzheimer disease. Proceedings of the National Academy of Sciences of the United States of America 89, 10016–10020.
   PubMed Web of Science ®Google Scholar
• Routledge, E.J. and Sumpter, J.P. (1997) Structural features of alkylphenolic chemicals with estrogenic activity. Journal of Biological Chemistry 272, 3280–3288.
   PubMed Web of Science ®Google Scholar
• Sano, M., Ernesto, C., Thomas, R.G., Klauber, M.R., Schafer, K., Grundman, M., Woodbury, P., Growdon, J., Cotman, C.W., Pfeiffer, E. et al. (1997) A controlled trial of selegiline, alpha-tocopherol, or both as treatment for Alzheimer's disease. New England Journal of Medicine 336, 1216–1222.
   PubMed Web of Science ®Google Scholar
• Schinkel, A.H., Smit, J.J., van Tellingen, O., Beijnen, J.H., Wagenaar, E., van Deemter, L., Mol, C.A., van der Falk, M.A., Robanus-Maandag, E.C., te Riele, H.P. et al. (1994) Disruption of the mouse mdr1a P-glycoprotein gene leads to a deficiency in the blood-brain barrier and to increased sensitivity to drugs. Cell 77, 491–502.
   PubMed Web of Science ®Google Scholar
• Schmidt, J.V. and Bradfield, C.A. (1996) Ah receptor signaling pathways. Annual Review of Cell and Developmental Biology 12, 55–89.
   PubMed Web of Science ®Google Scholar
• Seelig, A., Gottschlich, R. and Devant, R.M. (1994) A method to determine the ability of drugs to diffuse through the blood-brain barrier. Proceedings of the National Academy of Sciences of the United States of America 91, 68–72.
   PubMed Web of Science ®Google Scholar
• Sfakianos, J., Coward, L., Kirk, M. and Barnes, S. (1997) Intestinal uptake and biliary excretion of the isoflavone genistein in rats. Journal of Nutrition 127, 1260–1268.
   PubMed Web of Science ®Google Scholar
• Skaper, S.D., Fabris, M., Ferrari, V., Dalle Carbonate, M and Leon, A. (1997) Quercetin protects cutaneous tissue-associated cell types including sensory neurons from oxidative stress induced by glutathione depletion: cooperative effects of ascorbic acid. Free Radical Biology and Medicine 22, 669–678.
   PubMed Web of Science ®Google Scholar
• Soleas, G.J., Diamandis, E.P. and Goldberg, D.M. (1997) Resveratrol: a molecule whose time has come? And gone? Clinical Biochemistry 30, 91–113.
   PubMed Web of Science ®Google Scholar
• Terao, J., Piskula, M. and Yao, Q. (1994) Protective effect of epicatechin, epicatechin gallate, and quercetin on lipid peroxidation in phospholipid bilayers. Archives of Biochemistry and Biophysics 308, 278–284.
   PubMed Web of Science ®Google Scholar
• Tham, D.M., Gardner, C.D. and Haskell, W.L. (1998) Potential health benefits of dietary phytoestrogens: a review of the clinical, epidemiological and mechanistic evidence. Journal of Clinical Endocrinology and Metabolism 83, 2223–2235.
   PubMed Web of Science ®Google Scholar
• Uhr, M., Moosmann, B. and Behl, C. (1998) Aromatic alcohols as neuroprotectants. Journal of Neural Transmission 54(Suppl.), 287–294.
   Google Scholar
• Wang, T.T., Sathyamoorthy, N. and Phang, J.M. (1996) Molecular effects of genistein on estrogen receptor mediated pathways. Carcinogenesis 17, 271–275.
   PubMed Web of Science ®Google Scholar
• Wang, Q., Santizo, R., Baughman, V.L. and Pelligrino, D.A. (1999) Estrogen provides neuroprotection in transient forebrain ischemia through perfusion-independent mechanisms in rats. Stroke 30, 630–636.
   PubMed Web of Science ®Google Scholar
• Zhu, B.T. and Liehr, J.G. (1994) Quercetin increases the severity of estradiol-induced tumorigenesis in hamster kidney. Toxicology and Applied Pharmacology 125, 149–158.
   PubMed Web of Science ®Google Scholar