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The bioavailability of non-nutrient plant factors: dietary flavonoids and phyto-oestrogens

Published online by Cambridge University Press:  28 February 2007

Helen Wiseman
Helen Wiseman*
Affiliation:
Department of Nutrition and Dietetics, King's College London, Campden Hill Road, Kensington, London, W8 7AH, UK
*
Corresponding author: Dr Helen Wiseman, fax +44 (0)171 3334185, email Helen.Wiseman@kcl.ac.uk
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Abstract

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The bioavailability in human subjects of non-nutrient plant factors, including dietary flavonoids and phyto-oestrogens, is of great importance relative to their reported health protective effects. These effects include protection against heart disease, and also in the case of the phyto-oestrogens, hormone-dependent cancers. Epidemiological studies have shown flavonoid intake (mostly quercetin) to be inversely associated with mortality from CHD. Quercetin is a potent antioxidant in vitro, and protection against the oxidative damage to LDL implicated in atherogenesis has been suggested as a possible mechanism. Human subjects can absorb significant amounts of quercetin (particularly in the glucoside form) and it would appear to be sufficiently bioavailable to act as an antioxidant in vivo; however, following our recent study (J O'Reilly, TAB Sanders and H Wiseman, unpublished results), it is currently less clear whether quercetin really can act as an antioxidant in vivo. The isoflavone phyto-oestrogens genistein and daidzein are much less effective antioxidants than quercetin in vitro, however, they are well-absorbed by human subjects and appear to be sufficiently bioavailable to act as antioxidants in vivo. In our recent study (O'Reilly et al. 1998) lower plasma isoprostane concentrations and increased resistance of LDL to oxidation were observed following the high-isoflavone dietary phase compared with the low-isoflavone dietary phase. Considerable inter-individual variation in isoflavone metabolite excretion has been observed, in particular the production of equol (the gut bacterial metabolite of daidzein; a more potent antioxidant and more oestrogenic than daidzein), and this appears to be influenced by habitual diet. Further studies on the bioavailability of these non-nutrient plant factors and related influencing factors are clearly still required.

Keywords

Phyto-oestrogensFlavonoidsBioavailabilityAntioxidantsHeart DiseaseCancer
Type
Micronutrient Group Symposium on ‘Recent developments in bioavailability of micronutrients’
Information
Proceedings of the Nutrition Society , Volume 58 , Issue 1 , February 1999 , pp. 139 - 146
Copyright
Copyright © The Nutrition Society 1999

References

Adlercreutz, CHT, Goldin, BR, Gorbach, SL, Hockerstedt, KAV, Watanabe, S, Hamalainen, EK, Markkanen, MH, Makela, TH, Wahala, KT, Hase, TA & Fotsis, T (1995) Soybean phytoestrogen intake and cancer risk. Journal of Nutrition 125, 757S–770S.Google Scholar
Adlercreutz, H (1996) Lignans and isoflavonoids: epidemiology and possible role in prevention of cancer. In Natural Antioxidants and Food Quality in Atherosclerosis and Cancer Prevention, pp. 349–355 [Kumpulainen, JT and Salonen, JT, editors]. London: Royal Society of Chemistry.CrossRefGoogle Scholar
Adlercreutz, H, Markkanen, H & Watanabe, S (1993) Plasma concentrations of phytoestrogens in Japanese men. Lancet 342, 1209–1210.Google Scholar
Aziz, AA, Edwards, CA, Lean, MEJ & Crozier, A (1998) Absorption and excretion of conjugated flavonols, including quercetin-4′-O-β-glucoside and isorhamnetin-4′-O-β-glucoside by human volunteers after the consumption of onions. Free Radical Research (In the Press).Google Scholar
Bingham, SA, Atkinson, C, Liggins, J, Bluck, L & Coward, A (1998) Plant oestrogens: where are we now? British Journal of Nutrition 79, 393–406.CrossRefGoogle ScholarPubMed
Bowey, EA, Rowland, IR, Adlercreutz, H, Sanders, TAB & Wiseman, H (1999) Inter-individual variation in soya metabolism: the role of habitual diet. Proceedings of the Nutrition Society 58 (In the Press).Google Scholar
Brzozowski, AM, Pike, ACW, Dauter, Z, Hubbard, RE, Bonn, T, Engstrom, O, Ohman, L, Greene, GL, Gustafsson, J-A & Carlquist, M (1997) Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389, 753–758.Google Scholar
Cassidy, A (1996) Physiological effects of phyto-oestrogens in relation to cancer and other human health risks. Proceedings of the Nutrition Society 55, 399–417.CrossRefGoogle ScholarPubMed
Clarkson, TB, Anthony, MS & Hughes, CL Jr (1995) Estrogenic soybean isoflavones and chronic disease: risks and benefits. Trends in Endocrinology and Metabolism 6, 11–16.Google Scholar
Cook, NC & Samman, S (1996) Flavonoids: chemistry, metabolism, cardioprotective effects and dietary sources. Journal of Nutritional Biochemistry 7, 66–76.CrossRefGoogle Scholar
Crozier, A, Lean, MEJ, McDonald, MS & Black, C (1997) Quantitative analysis of the flavonoid content of commercial tomatoes, onions, lettuce and celery. Journal of Agricultural and Food Chemistry 45, 590–595.CrossRefGoogle Scholar
Dean, TS, O'Reilly, J, Bowey, E, Wiseman, H, Rowland, I & Sanders, TAB (1998) The effects of soyabean isoflavones on plasma HDL concentrations in healthy male and female subjects. Proceedings of the Nutrition Society 57, 123A.Google Scholar
De Vries, JHM, Janssen, PLTMK, Hollman, PCH, van Staveren, WA & Katan, MB (1997) Consumption of quercetin and kampferol in free-living subjects eating a variety of diets. Cancer Letters 114, 141–144.Google Scholar
De Whalley, C, Rankin, SM, Hoult, JRS, Jesssup, W & Leake, DS (1990) Flavonoids inhibit the oxidative modification of low density lipoproteins by macrophages. Biochemical Pharmacology 39, 1743–1750.CrossRefGoogle ScholarPubMed
Franke, AA & Custer, LJ (1996) Daidzein and genistein concentrations in human milk after soy consumption. Clinical Chemistry 42, 955–964.CrossRefGoogle ScholarPubMed
Franke, AA, Custer, LJ, Wang, W & Yang Shi, C (1998) HPLC analysis of isoflavonoids and other phenolic agents from foods and from human fluids. Proceedings of the Society for Experimental Biology and Medicine 217, 263–273.Google Scholar
Golbitz, P (1995) Traditional soyfoods: processing and products. Journal of Nutrition 125, 570S–572S.Google Scholar
Hertog, MGL, Feskens, EJM, Hollman, PCH, Katan, MB & Kromhout, D (1993 a) Dietary antioxidant flavonoids and the risk of coronary heart disease: the Zutphen Elderly Study. Lancet 342, 1007–1011.Google Scholar
Hertog, MGL, Feskens, EJM, Hollman, PCH, Katan, MB & Kromhout, D (1994) Dietary antioxidant flavonoids and cancer risk in the Zutphen Elderly Study. Nutrition and Cancer 22, 175–184.Google Scholar
Hertog, MGL & Hollman, PCH (1996) Potential health effects of the dietary flavonol quercetin. European Journal of Clinical Nutrition 50, 63–71.Google ScholarPubMed
Hertog, MGL, Hollman, PCH & Katan, MB (1992) Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands. Journal of Agricultural and Food Chemistry 40, 2379–2383.Google Scholar
Hertog, MGL, Hollman, PCH, Katan, MB & Kromhout, D (1993 b) Intake of potentially anticarcinogenic flavonoids and their determinants in adults in the Netherlands. Nutrition and Cancer 20, 21–29.Google Scholar
Hertog, MGL, Hollman, PCH & Van de Putte, B (1993 c) Content of potentially anticarcinogenic flavonoids of tea infusions, wines and fruit juices. Journal of Agricultural and Food Chemistry 41, 1242–1246.CrossRefGoogle Scholar
Hollman, PCH (1997 a) Determinants of the absorption of the dietary flavonoid quercetin in man. PhD Thesis, University of Wageningen, The Netherlands.Google Scholar
Hollman, PCH (1997 b) Bioavailability of flavonoids. European Journal of Clinical Nutrition 51, Suppl. 1, S66–S69.Google Scholar
Hollman, PCH, de Vries, JHM, van Leewen, SD, Mengelers, MJB & Katan, MB (1995) Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers. American Journal of Clinical Nutrition 62, 1276–1282.Google Scholar
Hollman, PCH, van der Gaag, MS, Mengelers, MJB, van Trijp, JMP, de Vries, JHM & Katan, MB (1996) Absorption and disposition kinetics of the dietary antioxidant quercetin in man. Free Radical Biology and Medicine 21, 703–707.Google Scholar
Hollman, PCH, van Trijp, JMP, Buysman, MNCP, van der Gaag, MS, Mengelers, MJB, de Vries, JHM & Katan, MB (1997 a) Relative bioavailability of the antioxidant flavonoid quercetin from various foods in man. FEBS Letters 418, 152–156.Google Scholar
Hollman, PCH, van Trijp, JMP, Mengelers, MJB, de Vries, JHM & Katan, MB (1997 b) Bioavailability of the dietary antioxidant flavonol quercetin in man. Cancer Letters 114, 139–140.CrossRefGoogle ScholarPubMed
Horn-Ross, PL, Barnes, S, Kirk, M, Coward, L, Parsonnet, J & Hiatt, RA (1997) Urinary phytoestrogen levels in young women from a multiethnic population. Cancer Epidemiology, Biomarkers and Prevention 6, 339–345.Google ScholarPubMed
Karr, SC, Lampe, JW, Hutchins, AM & Slavin, JL (1997) Urinary isoflavonoid excretion in humans is dose dependent at low to moderate levels of soy-protein consumption. American Journal of Clinical Nutrition 66, 46–51.Google Scholar
Keli, SO, Hertog, MGL, Keskens, EJM & Kromhout, D (1996) Dietary flavonoids, antioxidant vitamins and incidence of stroke: The Zutphen study. Archives of Internal Medicine 156, 637–642.Google Scholar
Kelly, GE, Joannou, GE, Reeder, AY, Nelson, C & Waring, MA (1995) The variable metabolic response to dietary isoflavones in humans. Proceedings of the Society for Experimental Biology and Medicine 208, 40–43.CrossRefGoogle ScholarPubMed
King, RA & Bursill, DB (1998) Plasma and urinary kinetics of the isoflavones daidzein and genistein after a single soy meal in humans. American Journal of Clinical Nutrition 67, 867–872.Google Scholar
Kirkman, LM, Lampe, JW, Campbell, DR, Martini, MC & Slavin, JL (1995) Urinary lignan and isoflavonoid excretion in men and women consuming vegetable and soy diets. Nutrition and Cancer 24, 1–12.CrossRefGoogle ScholarPubMed
Lampe, JW, Karr, SC, Hutchins, AM & Slavin, JL (1998) Urinary equol excretion with a soy challenge: influence of habitual diet. Proceedings of the Society for Experimental Biology and Medicine 217, 335–339.Google Scholar
Lapcik, O, Hill, M, Hampl, R, Wahala, K & Adlercreutz, H (1998) Identification of isoflavonoids in beer. Steroids 63, 14–20.CrossRefGoogle ScholarPubMed
Lu, L-JW, Grady, JJ, Marshall, MV, Ramanujam, S & Anderson, KE (1995) Altered time course of urinary daidzein and genistein excretion during chronic soya diet in healthy male subjects. Nutrition and Cancer 24, 311–323.CrossRefGoogle ScholarPubMed
Lu, L-JW, Lin, S-N, Grady, JJ, Nagamani, M & Anderson, KE (1996) Altered kinetics and extent of urinary daidzein and genistein excretion in women during chronic soya exposure. Nutrition and Cancer 26, 289–302.Google Scholar
Miksicek, RJ (1995) Estrogenic flavonoids: structural requirements for biological activity. Proceedings of the Society for Experimental Biology and Medicine 208, 44–50.Google Scholar
Morton, MS, Matos-Ferreira, A, Abranches-Monteiro, L, Correia, R, Blacklock, N, Chan, PSF, Cheng, C, Lloyd, S, Chieh-Ping, W & Griffiths, K (1997) Measurement and metabolism of isoflavonoids and lignans in the human male. Cancer Letters 114, 145–151.Google Scholar
Morton, MS, Wilcox, G, Wahlqvist, ML & Griffiths, K (1994) Determination of lignans and isoflavonoids in human female plasma following dietary supplementation. Journal of Endocrinology 142, 251–259.Google Scholar
O'Reilly, J, Dean, TS, Bowey, E, Rowland, I, Sanders, TAB & Wiseman, H (1998) The influence of dietary isoflavones on markers of lipid peroxidation in healthy male and female volunteers. Proceedings of the Nutrition Society 57, 123A.Google Scholar
Paganga, G & Rice-Evans, CA (1997) The identification of flavonoids as glycosides in human plasma. FEBS Letters 401, 78–82.Google Scholar
Pettersson, D, Aman, P, Knudsen, KEB, Lundin, E, Zhang, JX, Hallmans, G, Harkonen, H & Adlercreutz, H (1996) Intake of rye bread by ileostomists increases ileal excretion of fiber polysaccharide components and organic acids but does not increase plasma or urine lignans and isoflavonoids. Journal of Nutrition 126, 1594–1600.Google Scholar
Raines, EW & Ross, R (1995) Biology of atherosclerotic plaque formation: possible role of growth factors in lesion development and the potential impact of soy. Journal of Nutrition 125, 624S–630S.Google Scholar
Reinli, K & Block, G (1996) Phytoestrogen content of foods - a compendium of literature values. Nutrition and Cancer 26, 123–148.CrossRefGoogle Scholar
Slavin, J, Jacobs, D & Marquart, L (1997) Whole-grain consumption and chronic disease: Protective mechanisms. Nutrition and Cancer 27, 14–21.Google Scholar
Steinberg, D, Parthasarathy, S, Carew, TE, Khoo, JC & Witzum, JL (1989) Modifications of low-density lipoprotein that increase its atherogenicity. New England Journal of Medicine 320, 915–924.Google Scholar
Tikkanen, MJ, Wahala, K, Ojala, S, Vihma, V & Adlercreutz, H (1998) Effect of soybean phytoestrogen intake on low density lipoprotein resistance. Proceedings of the National Academy of Sciences 95, 3106–3110.CrossRefGoogle Scholar
Thompson, LU (1994) Antioxidant and hormone-mediated health benefits of whole grains. Critical Reviews in Food Science and Nutrition 34, 473–497.Google Scholar
Williams, RL & Rutledge, T (1998) Recent phytoestrogen research. Chemistry and Industry January, 14–16.Google Scholar
Wiseman, H (1994) Tamoxifen: Molecular Basis of Use in Cancer Treatment and Prevention. Chichester: John Wiley.Google Scholar
Wiseman, H (1996) Role of dietary phyto-oestrogens in the protection against cancer and heart disease. Biochemical Society Transactions 24, 795–800.CrossRefGoogle ScholarPubMed
Wiseman, H (1997) Dietary phytoestrogens: disease prevention versus potential hazards. Nutrition and Food Science 1, 32–38.Google Scholar
Wiseman, H (1998) Phytochemicals (b) Epidemiological factors. In Encyclopedia of Human Nutrition [Sadler, M, Caballero, B and Strain, S, editors]. London: Academic Press (In the Press).Google Scholar
Wiseman, H & Halliwell, B (1996) Damage to DNA by reactive oxygen and nitrogen species: role in inflammatory disease and progression to cancer. Biochemical Journal 313, 17–29.Google Scholar
Wiseman, H & O'Reilly, J (1997) Oestrogens as antioxidant cardioprotectants. Biochemical Society Transactions 25, 54–59.CrossRefGoogle ScholarPubMed
Wiseman, H, O'Reilly, J, Lim, P, Garnett, AP, Huang, W-C & Sanders, TAB (1998) Antioxidant properties of the isoflavone phytoestrogen functional ingredient in soya products. In Functional Foods, The Consumer, The Products and The Evidence, pp. 80–86 [Sadler, M and Saltmarsh, M, editors]. Cambridge: Royal Society of Chemistry.Google Scholar
Wiseman, H, Paganga, G, Rice-Evans, C & Halliwell, B (1993) Protective actions of tamoxifen and 4-hydroxytamoxifen against oxidative damage to human low-density lipoproteins: a mechanism accounting for the protective action of tamoxifen? Biochemical Journal 292, 635–638.Google Scholar
Xu, X, Harris, KS, Wang, H-J, Murphy, PA & Hendrich, S (1995) Bioavailability of soybean isoflavones depends upon gut microflora in women. Journal of Nutrition 125, 2307–2315Google Scholar