Hostname: page-component-cd9895bd7-mkpzs Total loading time: 0 Render date: 2024-12-23T13:46:24.200Z Has data issue: false hasContentIssue false
  • English
  • Français

Daidzein and genistein contents of vegetables

Published online by Cambridge University Press:  09 March 2007

J. Liggins ,
L. J. C. Bluck ,
S. Runswick ,
C. Atkinson ,
W. A. Coward  and
S. A. Bingham
J. Liggins
Affiliation:
Medical Research Council, Dunn Human Nutrition Unit, Wellcome Trust/MRC Building, Hills Road, Cambridge CB2 2XY, UK
L. J. C. Bluck
Affiliation:
Medical Research Council, Human Nutrition Research, Downhams Lane, Milton Road, Cambridge CB4 1XJ, UK
S. Runswick
Affiliation:
Medical Research Council, Dunn Human Nutrition Unit, Wellcome Trust/MRC Building, Hills Road, Cambridge CB2 2XY, UK
C. Atkinson
Affiliation:
Medical Research Council, Dunn Human Nutrition Unit, Wellcome Trust/MRC Building, Hills Road, Cambridge CB2 2XY, UK
W. A. Coward
Affiliation:
Medical Research Council, Human Nutrition Research, Downhams Lane, Milton Road, Cambridge CB4 1XJ, UK
S. A. Bingham*
Affiliation:
Medical Research Council, Dunn Human Nutrition Unit, Wellcome Trust/MRC Building, Hills Road, Cambridge CB2 2XY, UK
*
*Corresponding author: Dr Sheila Bingham, tel +44 1223 252760, fax +44 1223 252765, email [email protected]
Rights & Permissions [Opens in a new window]

Abstract

Core share and HTML view are not available for this content. However, as you have access to this content, a full PDF is available via the ‘Save PDF’ action button.

Food samples (n 114) were prepared from vegetables commonly eaten in Europe. The glycosidic forms of the phyto-oestrogens daidzein and genistein were extracted from the dried foods into aqueous methanol. The isoflavones were quantified by GC–MS after hydrolytic removal of any conjugated carbohydrate. Completeness of extraction and any procedural losses of the isoflavones were accounted for using synthetic daidzin (7-O-glucosyl-4′-hydroxyisoflavone) and genistin (7-O-glucosyl-4′5-dihydroxyisoflavone) as internal standards. Of the 114 foods assayed, at a limit of quantification of 0·1 μg/kg dry weight, forty-eight contained no detectable daidzein or genistein, forty-one contained less than 100 μg/kg of the two isoflavones combined and the remaining twenty-five contained more than this amount. Soyabean products contained between 470 and 1420 mg (average of 960 mg) daidzein and genistein combined per kg wet weight of food, and legumes contained between 20 and 5750 μg/kg wet weight of food, with an average of 620 μg/kg. Cooking by boiling in water caused a decrease in the daidzein and genistein content of food in twenty-four of twenty-eight foods. The extent of the decrease was variable and warrants further investigation. The present paper comprises the first comprehensive description of the content of daidzein and genistein in vegetables.

Keywords

Phyto-oestrogensDaidzeinGenistein
Type
Research Article
Information
British Journal of Nutrition , Volume 84 , Issue 5 , November 2000 , pp. 717 - 725
Copyright
Copyright © The Nutrition Society 2000

References

Adlercreutz, H, Fotsis, T, Bannwart, C, Wahala, K, Brunow, G and Hase, T (1991) Isotope-dilution gas-chromatographic mass-spectrometric method for the determination of lignans and isoflavonoids in human urine, including identification of genistein. Clinica Chimica Acta 199, 263–278.CrossRefGoogle ScholarPubMed
Adlercreutz, H, Fotsis, T, Kurzer, MS, Wahala, K, Makela, T and Hase, T (1995) Isotope-dilution gas-chromatographic mass-spectrometric method for the determination of unconjugated lignans and isoflavonoids in human feces, with preliminary results in omnivorous and vegetarian women. Analytical Biochemistry 225, 101–108.CrossRefGoogle ScholarPubMed
Adlercreutz, H and Mazur, W (1997) Phyto-oestrogens and Western diseases. Annals of Medicine 29, 95–120.CrossRefGoogle ScholarPubMed
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.CrossRefGoogle ScholarPubMed
Arts, J, Kuiper, G, Janssen, J, Gustafsson, JA, Lowik, C, Pols, HAP and VanLeeuwen, J (1997) Differential expression of estrogen receptors alpha and beta mRNA during differentiation of human osteoblast SV-HFO cells. Endocrinology 138, 5067–5070.CrossRefGoogle ScholarPubMed
Barkhem, T, Carlsson, B, Nilsson, Y, Enmark, E, Gustafsson, JA and Nilsson, S (1998) Differential response of estrogen receptor alpha and estrogen receptor beta to partial estrogen agonists/antagonists. Molecular Pharmacology 54, 105–112.CrossRefGoogle ScholarPubMed
Bingham, SA, Atkinson, C, Liggins, J, Bluck, L and Coward, A (1998) Plant oestrogens: Where are we now?. British Journal of Nutrition 79, 393–406.CrossRefGoogle ScholarPubMed
Brzezinski, A, Adlercreutz, H, Shaoul, R, Rosler, A, Shmueli, A, Tanos, V and Schenker, JG (1997) Short-term effects of phytoestrogen-rich diet on postmenopausal women. Menopause 4, 89–94.CrossRefGoogle Scholar
Cassidy, A, Bingham, S, Setchel, K and Watson, D (1991) Urinary plant oestrogen excretion in post menopausal women. Proceedings of the Nutrition Society 50, 105A.Google Scholar
Chang, YC and Nair, MG (1995) Metabolism of daidzein and genistein by intestinal bacteria. Journal of Natural Products 58, 1892–1896.CrossRefGoogle ScholarPubMed
Dalais, FS, Rice, GE, Wahlqvist, ML, HsuHage BHH and Wattanapenpaiboon, N (1998) Urinary excretion of isoflavonoid phytoestrogens in Chinese and Anglo-Celtic populations in Australia. Nutrition Research 18, 1703–1709.CrossRefGoogle Scholar
Enmark, E, PeltoHuikko, M, Grandien, K, Lagercrantz, S, Lagercrantz, J, Fried, G, Nordenskjold, M and Gustafsson, JA (1997) Human estrogen receptor beta-gene structure, chromosomal localization, and expression pattern. Journal of Clinical Endocrinology and Metabolism 82, 4258–4265.Google ScholarPubMed
Franke, AA, Custer, LJ, Cerna, CM and Narala, KK (1994) Quantitation of phytoestrogens in legumes by HPLC. Journal of Agricultural and Food Chemistry 42, 1905–1913.CrossRefGoogle Scholar
Gang, DR, Dinkova-Kostova, AT, Davin, LB and Lewis, NG (1997) Phylogenetic links in plant defense systems: lignans, isoflavonoids, and their reductases. ACS Symposium Series 658, 58–89.CrossRefGoogle Scholar
Holland, B, Unwin, ID and Buss, DH (1991) Vegetables and Spices: Fifth Supplement to McCance and Widdowson's The Composition of Foods, 4th ed. Cambridge: Royal Socitey of Chemistry and ministry of Agriculture, Fisheris and Food.CrossRefGoogle Scholar
Horn-Ross, PL, Barnes, S, Kirk, M, Coward, L, Parsonnet, J and Hiatt, RA (1997) Urinary phytoestrogen levels in young women from a multiethnic population. Cancer Epidemiology, Biomarkers and Prevention 6, 339–345.Google ScholarPubMed
Hutchins, AM, Slavin, JL and Lampe, JW (1995) Urinary isoflavonoid phytoestrogen and lignan excretion after consumption of fermented and unfermented soy products. Journal of the American Dietetic Association 95, 545–551.CrossRefGoogle ScholarPubMed
Karr, SC, Lampe, JW, Hutchins, AM and 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.CrossRefGoogle ScholarPubMed
Kelly, GE, Joannou, GE, Reeder, AY, Nelson, C and 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
Kuiper, G and Gustafsson, JA (1997) The novel estrogen receptor-beta subtype: potential role in the cell- and promoter-specific actions of estrogens and anti-estrogens. FEBS Letters 410, 87–90.CrossRefGoogle ScholarPubMed
Kuiper, G, Lemmen, JG, Carlsson, B, Corton, JC, Safe, SH, VanderSaag, PT, VanderBurg P and Gustafsson, JA (1998) Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology 139, 4252–4263.CrossRefGoogle ScholarPubMed
Kurzer, MS and Xu, X (1997) Dietary phytoestrogens. Annual Review of Nutrition 17, 353–381.CrossRefGoogle ScholarPubMed
Lers, A, Burd, S, Lomaniec, E, Droby, S and Chalutz, E (1998) The expression of a grapefruit gene encoding an isoflavone reductase-like protein is induced in response to UV irradiation. Plant Molecular Biology 36, 847–856.CrossRefGoogle ScholarPubMed
Liggins, J, Bluck, LJC, Coward, WA and Bingham, SA (1998) Extraction and quantification of daidzein and genistein in food. Analytical Biochemistry 264, 1–7.CrossRefGoogle ScholarPubMed
Manguro, LOA, Midiwo, JO and Kraus, W (1996) A new flavonol tetraglycoside from Myrsine africana leaves. Natural Product Letters 9, 121–126.CrossRefGoogle Scholar
Maskarinec, G, Singh, S, Meng, LX and Franke, AA (1998) Dietary soy intake and urinary isoflavone excretion among women from a multiethnic population. Cancer Epidemiology, Biomarkers and Prevention 7, 613–619.Google ScholarPubMed
Mazur, WM, Duke, JA, Wahala, K, Rasku, S and Adlercreutz, H (1998) Isoflavonoids and lignans in legumes: nutritional and health aspects in humans. Journal of Nutritional Biochemistry 9, 193–200.CrossRefGoogle Scholar
Messina, MJ, Persky, V, Setchell, KDR and Barnes, S (1994) Soy intake and cancer risk: a review of the in vitro and in vivo data. Nutrition and Cancer 21, 113–131.CrossRefGoogle Scholar
Morton, MS, Chan, PSF, Cheng, C, Blacklock, N, Matos-Ferreira, A, Abranches-Monteiro, L, Correia, R, Lloyd, S and Griffiths, K (1997) Lignans and isoflavonoids in plasma and prostatic fluid in men: samples from Portugal, Hong Kong, and the United Kingdom. Prostate 32, 122–128.3.0.CO;2-O>CrossRefGoogle ScholarPubMed
Morton, MS, Matos-Ferreira, A, Abranches-Monteiro, L, Correia, R, Blacklock, N, Chan, PSF, Cheng, C, Lloyd, C, Chiehping, W and Griffiths, K (1997) Measurement and metabolism of isolflavonoids and lignans in the human male. Cancer Letters 114, 145–151.CrossRefGoogle ScholarPubMed
Morton, MS, Wilcox, G, Wahlqvist, ML and Griffiths, K (1994) Determination of lignans and isoflavonoids in human female plasma following dietary supplementation. Journal of Endocrinology 142, 251–259.CrossRefGoogle ScholarPubMed
Murkies, AL, Wilcox, G and Davis, SR (1998) Phytoestrogens. Journal of Clinical Endocrinology and Metabolism 83, 297–303.Google ScholarPubMed
Reinli, K and Block, G (1996) Phytoestrogen content of foods – a compendium. Nutrition and Cancer 26, 123–148.CrossRefGoogle Scholar
Ruiz, Larrea, MB, Mohan, AR, Paganga, G, Miller, NJ, Bolwell, GP and Rice Evans, CA (1997) Antioxidant activity of phytoestrogenic isoflavones. Free Radical Research 26, 63–70.CrossRefGoogle Scholar
Seow, A, Shi, CY, Franke, AA, Hankin, JH, Lee, HP and Yu, MC (1998) Isoflavonoid levels in spot urine are associated with frequency of dietary soy intake in a population-based sample of middle-aged and older Chinese in Singapore. Cancer Epidemiology, Biomarkers and Prevention 7, 135–140.Google Scholar
Thompson, M and Wood, R (1995) Harmonised guidelines for internal quality control in analytical chemistry laboratories. Pure and Applied Chemistry 67, 649–666.CrossRefGoogle Scholar
Wang, H and Murphy, PA (1994) Isoflavone composition of American and Japanese soybeans in Iowa: effects of variety, crop year, and location. Journal of Agricultural and Food Chemistry 42, 1674–1677.CrossRefGoogle Scholar
Wei, H, Bowen, R, Cai, Q, Barnes, S and Wang, Y (1995) Antioxidant and antipromotional effects of the soybean isoflavone genistein. Proceedings of the Society for Experimental Biology and Medicine 208, 124–130.CrossRefGoogle ScholarPubMed