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Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Published online by Cambridge University Press:  08 March 2007

Ivon E. J. Milder
Affiliation:
RIKILT-Institute of Food Safety, Wageningen University and Research Centre, PO Box 230, 6700 AE Wageningen, The Netherlands Centre for Nutrition and Health, National Institute for Public Health and the Environment, PO Box 1, 3720 BA Bilthoven, The Netherlands
Ilja C. W. Arts
Affiliation:
RIKILT-Institute of Food Safety, Wageningen University and Research Centre, PO Box 230, 6700 AE Wageningen, The Netherlands
Betty van de Putte
Affiliation:
RIKILT-Institute of Food Safety, Wageningen University and Research Centre, PO Box 230, 6700 AE Wageningen, The Netherlands
Dini P. Venema
Affiliation:
RIKILT-Institute of Food Safety, Wageningen University and Research Centre, PO Box 230, 6700 AE Wageningen, The Netherlands
Peter C. H. Hollman*
Affiliation:
RIKILT-Institute of Food Safety, Wageningen University and Research Centre, PO Box 230, 6700 AE Wageningen, The Netherlands
*
*Corresponding author: Dr Peter C. H. Hollman, fax +31 317 417717, email Peter.Hollman@wur.nl
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Abstract

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Enterolignans (enterodiol and enterolactone) can potentially reduce the risk of certain cancers and cardiovascular diseases. Enterolignans are formed by the intestinal microflora after the consumption of plant lignans. Until recently, only secoisolariciresinol and matairesinol were considered enterolignan precursors, but now several new precursors have been identified, of which lariciresinol and pinoresinol have a high degree of conversion. Quantitative data on the contents in foods of these new enterolignan precursors are not available. Thus, the aim of this study was to compile a lignan database including all four major enterolignan precursors. Liquid chromatography–tandem mass spectrometry was used to quantify lariciresinol, pinoresinol, secoisolariciresinol and matairesinol in eighty-three solid foods and twenty-six beverages commonly consumed in The Netherlands. The richest source of lignans was flaxseed (301 129 μg/100 g), which contained mainly secoisolariciresinol. Also, lignan concentrations in sesame seeds (29 331 μg/100 g, mainly pinoresinol and lariciresinol) were relatively high. For grain products, which are known to be important sources of lignan, lignan concentrations ranged from 7 to 764 μg/100 g. However, many vegetables and fruits had similar concentrations, because of the contribution of lariciresinol and pinoresinol. Brassica vegetables contained unexpectedly high levels of lignans (185–2321 μg/100 g), mainly pinoresinol and lariciresinol. Lignan levels in beverages varied from 0 (cola) to 91 μg/100 ml (red wine). Only four of the 109 foods did not contain a measurable amount of lignans, and in most cases the amount of lariciresinol and pinoresinol was larger than that of secoisolariciresinol and matairesinol. Thus, available databases largely underestimate the amount of enterolignan precursors in foods.

Type
Research Article
Copyright
Copyright © The Nutrition Society 2005

References

Adlercreutz, H & Mazur, W (1997) Phyto-oestrogens and Western diseases. Ann Med 29, 95120.CrossRefGoogle ScholarPubMed
Adlercreutz, H, Mazur, W & Bartels, P (2000) Phytoestrogens and prostate disease. J Nutr 130 658S – 659S.CrossRefGoogle ScholarPubMed
Adlercreutz, H, Mousavi, Y, Clark, J, Hockerstedt, K, Hamalainen, E, Wähälä, K, Makela, T & Hase, T (1992) Dietary phytoestrogens and cancer – in vitro and in vivo studies. J Steroid Biochem Mol Biol 41, 331337.CrossRefGoogle ScholarPubMed
Andreasen, MF, Kroon, PA, Williamson, G, Garcia-Conesa, MT (2001) Intestinal release and uptake of phenolic antioxidant diferulic acids. Free Radical Biol Med 31, 304314.CrossRefGoogle ScholarPubMed
Arts, ICW & Hollman, PCH (2005) Polyphenols and disease risk in epidemiological studies. Am J Clin Nutr 81, 53175325, Suppl.CrossRefGoogle Scholar
Arts, ICW, van de, Putte, B Hollman, PCH (2000) Catechin contents of foods commonly consumed in The Netherlands. 1. Fruits, vegetables, staple foods, and processed foods. J Agric Food Chem 48, 17461751.CrossRefGoogle ScholarPubMed
Begum, AN, Nicolle, C & Mila, I (2004) Dietary lignins are precursors of mammalian lignans in rats. J Nutr 134, 120127.CrossRefGoogle ScholarPubMed
Brenes, M, Garcia, A, Dobarganes, MC, Velasco, J & Romero, C (2002a) Influence of thermal treatments simulating cooking processes on the polyphenol content in virgin olive oil. J Agric Food Chem 50, 59625967.CrossRefGoogle ScholarPubMed
Brenes, M, Garcia, A, Rios, JJ, Garcia, P & Garrido, A (2002b) Use of 1-acetoxypinoresinol to authenticate Picual olive oils. Int J Food Sci Tech 37, 615625.CrossRefGoogle Scholar
Dai, Q, Franke, AA, Jin, F, Shu, XO, Hebert, JR, Custer, LJ, Cheng, JR, Gan, YT & Zheng, W (2002) Urinary excretion of phytoestrogens and risk of breast cancer among Chinese women in Shanghai. Cancer Epidemiol Biomarkers Prev 11, 815821.Google ScholarPubMed
Den, Tonkelaar, I, Keinan-Boker, L, Van, t, Veer, P, Arts, CJM, Adlercreutz, H, Thijssen, JHH Peeters, PHM (2001) Urinary phytoestrogens and postmenopausal breast cancer risk. Cancer Epidemiol Biomarkers Prev 10, 223228.Google Scholar
Ford, JD, Huang, KS, Wang, HB, Davin, LB & Lewis, NG (2001) Biosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside-hydroxymethyl glutaryl ester-linked lignan oligomers in flax ( Linum usitatissimum ) seed. J Nat Prod 64, 13881397.CrossRefGoogle Scholar
Grace, PB, Taylor, JI & Low, YL (2004) Phytoestrogen concentrations in serum and spot urine as biomarkers for dietary phytoestrogen intake and their relation to breast cancer risk in European prospective investigation of cancer and nutrition-norfolk. Cancer Epidemiol Biomarkers Prev 13, 698708.CrossRefGoogle ScholarPubMed
Heinonen, S, Nurmi, T, Liukkonen, K, Poutanen, K, Wähälä, K, Deyama, T, Nishibe, S & Adlercreutz, H (2001) In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol. J Agric Food Chem 49, 31783186.CrossRefGoogle ScholarPubMed
Hertog, MGL, Hollman, PCH & Katan, MB (1992) Content of potentially anticarcinogenic flavanoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands. J Agric Food Chem 40, 23792383.CrossRefGoogle Scholar
Horn-Ross, PL, Barnes, S, Lee, M, Coward, L, Mandel, JE, Koo, J, John, EM & Smith, M (2000) Assessing phytoestrogen exposure in epidemiologic studies: development of a database (United States). Cancer Causes Control 11, 289298.CrossRefGoogle ScholarPubMed
Horn-Ross, PL, Hoggatt, KJ & Lee, MM (2002a) Phytoestrogens and thyroid cancer risk: the San Francisco Bay Area thyroid cancer study. Cancer Epidemiol Biomarkers Prev 11, 4349.Google ScholarPubMed
Horn-Ross, PL, Hoggatt, KJ & West, DW (2002b) Recent diet and breast cancer risk: the California teachers study (USA). Cancer Causes Control 13, 407415.CrossRefGoogle ScholarPubMed
Horn-Ross, PL, John, EM, Canchola, AJ, Stewart, SL & Lee, MM (2003) Phytoestrogen intake and endometrial cancer risk. J Natl Cancer Inst 95, 11581164.CrossRefGoogle ScholarPubMed
Horn-Ross, PL, John, EM & Lee, M (2001) Phytoestrogen consumption and breast cancer risk in a multiethnic population – the Bay Area Breast Cancer Study. Am J Epidemiol 154, 434441.CrossRefGoogle Scholar
Hulshof, KF, Van Staveren, WA (1991) The Dutch National Food Consumption Survey: design, methods and first results. Food Policy 16, 257260.CrossRefGoogle Scholar
Hulten, K, Winkvist, A, Lenner, P, Johansson, R, Adlercreutz, H & Hallmans, G (2002) An incident case-referent study on plasma enterolactone and breast cancer risk. Eur J Nutr 41, 168176.CrossRefGoogle ScholarPubMed
Ingram, D, Sanders, K, Kolybaba, M & Lopez, D (1997) Case-control study of phyto-oestrogens and breast cancer. Lancet 350, 990994.CrossRefGoogle ScholarPubMed
Jiao, Y, Davin, LB & Lewis, NG (1998) Furanofuran lignan metabolism as a function of seed maturation in Sesamum indicum: methylenedioxy bridge formation. Phytochemistry 49, 387394.CrossRefGoogle Scholar
Johnsson, P, Kamal, Eldin, A, Lundgren, LN Aman, P (2000) HPLC method for analysis of secoisolariciresinol diglucoside in flaxseeds. J Agric Food Chem 48, 52165219.CrossRefGoogle ScholarPubMed
Juntunen, KS, Mazur, WM, Liukkonen, KH, Uehara, M, Poutanen, KS, Adlercreutz, HCT & Mykkanen, HM (2000) Consumption of wholemeal rye bread increases serum concentrations and urinary excretion of enterolactone compared with consumption of white wheat bread in healthy Finnish men and women. Br J Nutr 84, 839846.CrossRefGoogle ScholarPubMed
Kato, MJ, Chu, A, Davin, LB & Lewis, NG (1998) Biosynthesis of antioxidant lignans in Sesamum indicum seeds. Phytochemistry 47, 583591.CrossRefGoogle Scholar
Katsuzaki, H, Kawasumi, M, Kawakishi, S & Osawa, T (1992) Structure of novel antioxidative lignan glucosides isolated from sesame seed. Biosci Biotechn Biochem 56, 20872088.CrossRefGoogle Scholar
Keinan, Boker, L, Van, der, Schouw, YT, De, Kleijn, MJ, Jacques, PF, Grobbee, DE & Peeters, PH (2002) Intake of dietary phytoestrogens by Dutch women. J Nutr 132, 13191328.Google Scholar
Kraushofer, T & Sontag, G (2002a) Determination of some phenolic compounds in flax seed and nettle roots by HPLC with coulometric electrode array detection. Eur Food Res. Technol. 215, 529533.CrossRefGoogle Scholar
Kraushofer, T & Sontag, G (2002b) Determination of matairesinol in flax seed by HPLC with coulometric electrode array detection. J. Chromatogr B Biomed Sci Appl 777, 6166.Google ScholarPubMed
Lapierre, C, Pollet, B, Ralet, MC & Saulnier, L (2001) The phenolic fraction of maize bran: evidence for lignin-heteroxylan association. Phytochemistry 57, 765772.CrossRefGoogle ScholarPubMed
Liggins, J, Grimwood, R & Bingham, SA (2000) Extraction and quantification of lignan phytoestrogens in food and human samples. Anal Biochem 287, 102109.CrossRefGoogle ScholarPubMed
Linseisen, J, Piller, R, Hermann, S, Chang-Claude, J (2004) Dietary phytoestrogen intake and premenopausal breast cancer risk in a German case-control study. Int J Cancer 110, 284290.CrossRefGoogle Scholar
McCann, SE, Freudenheim, JL, Marshall, JR & Graham, S (2003) Risk of human ovarian cancer is related to dietary intake of selected nutrients, phytochemicals and food groups. J Nutr 133, 19371942.CrossRefGoogle ScholarPubMed
McCann, SE, Moysich, KB, Freudenheim, JL, Ambrosone, CB & Shields, PG (2002) The risk of breast cancer associated with dietary lignans differs by CYP17 genotype in women. J Nutr 132, 30363041.CrossRefGoogle ScholarPubMed
Manach, C, Scalbert, A, Morand, C, Remesy, C & Jimenez, L (2004) Polyphenols: food sources and bioavailability. Am J Clin Nutr 79, 727747.CrossRefGoogle ScholarPubMed
Mazur, W (1998) Phytoestrogen content in foods. Baillières Clin Endocrinol Metab 12, 729742.CrossRefGoogle ScholarPubMed
Mazur, W & Adlercreutz, H (1998) Naturally occurring oestrogens in food. Pure Appl Chem 70, 17591776.CrossRefGoogle Scholar
Mazur, W & Adlercreutz, H (2000) Overview of naturally occurring endocrine-active substances in the human diet in relation to human health. Nutrition 16, 654658.CrossRefGoogle ScholarPubMed
Mazur, WM, Duke, JA, Wähälä, K, Rasku, S & Adlercreutz, H (1998a) Isoflavonoids and lignans in legumes: nutritional and health aspects in humans. J Nutr Biochem 9, 193200.CrossRefGoogle Scholar
Mazur, W, Fotsis, T, Wähälä, K, Ojala, S, Salakka, A & Adlercreutz, H (1996) Isotope dilution gas chromatographic-mass spectrometric method for the determination of isoflavonoids, coumestrol, and lignans in food samples. Anal Biochem 233, 169180.CrossRefGoogle ScholarPubMed
Mazur, WM, Uehara, M, Wähälä, K & Adlercreutz, H (2000) Phyto-oestrogen content of berries, and plasma concentrations and urinary excretion of enterolactone after a single strawberry-meal in human subjects. Br J Nutr 83, 381387.Google ScholarPubMed
Mazur, WM, Wähälä, K, Rasku, S, Salakka, A, Hase, T & Adlercreutz, H (1998b) Lignan and isoflavonoid concentrations in tea and coffee. Br J Nutr 79, 3745.CrossRefGoogle ScholarPubMed
Meagher, LP & Beecher, GR (2000) Assessment of data on the lignan content of foods. J Food Compos Anal 13, 935947.CrossRefGoogle Scholar
Meagher, LP, Beecher, GR, Flanagan, VP & Li, BW (1999) Isolation and characterization of the lignans, isolariciresinol and pinoresinol, in flaxseed meal. J Agric Food Chem 47, 31733180.CrossRefGoogle ScholarPubMed
Milder, IEJ, Arts, ICW, Venema, DP, Lasaroms, JJP, Wähälä, K & Holllman, PCH (2004) Optimization of a liquid chromatography-tandem mass spectrometry method for quantification of the plant lignans secoisolariciresinol, matairesinol, lariciresinol and pinoresinol in foods. J Agric Food Chem 52, 46434651.CrossRefGoogle ScholarPubMed
Muir, AD & Westcott, ND (2000) Quantitation of the lignan secoisolariciresinol diglucoside in baked goods containing flax seed or flax meal. J Agric Food Chem 48, 40484052.CrossRefGoogle ScholarPubMed
Murkovic, M, Piironen, V, Lampi, AM, Kraushofer, T & Sontag, G (2004) Changes in chemical composition of pumpkin seeds during the roasting process for production of pumpkin seed oil. 1. Non-volatile compounds. Food Chem 84, 359365.CrossRefGoogle Scholar
Nilsson, M, Aman, P, Harkonen, H, Hallmans, G, Knudsen, KEE, Mazur, W & Adlercreutz, H (1997a) Nutrient and lignan content, dough properties and baking performance of rye samples used in Scandinavia. Acta Agric Scand Sect B Soil Plant Sci 47, 2634.Google Scholar
Nilsson, M, Aman, P, Harkonen, H, Hallmans, G, Knudsen, K, Mazur, W & Adlercreutz, H (1997b) Content of nutrients and lignans in roller milled fractions of rye. J Sci Food Agric 73, 143148.3.0.CO;2-H>CrossRefGoogle Scholar
Nurmi, T, Heinonen, S, Mazur, W, Deyama, T, Nishibe, S & Adlercreutz, H (2003) Lignans in selected wines. Food Chem 83, 303309.CrossRefGoogle Scholar
Obermeyer, WR, Musser, SM, Betz, JM, Casey, RE, Pohland, AE & Page, SW (1995) Chemical studies of phytoestrogens and related compounds in dietary supplements: flax and chaparral. Proc Soc Exp Biol Med 208, 612.CrossRefGoogle ScholarPubMed
Owen, RW, Mier, W, Giacosa, A, Hull, WE, Spiegelhalder, B & Bartsch, H (2000) Identification of lignans as major components in the phenolic fraction of olive oil. Clin Chem 46, 976988.CrossRefGoogle ScholarPubMed
Pietinen, P, Stumpf, K, Mannisto, S, Kataja, V, Uusitupa, M & Adlercreutz, H (2001) Serum enterolactone and risk of breast cancer: a case-control study in Eastern Finland. Cancer Epidemiol Biomarkers Prev 10, 339344.Google ScholarPubMed
Qui, SX, Lu, ZZ, Luyengi, L, Lee, SK, Pezzuto, JM, Farnsworth, NR, Thompson, LU & Fong, HHS (1999) Isolation and characterization of flaxseed ( Linum usitatissimum ) constituents. Pharm Biol 37, 17.Google Scholar
Raffaelli, B, Hoikkala, A, Leppala, E, Wähälä, K (2002) Enterolignans. J Chromatogr B Biomed Sci Appl 777, 2943.Google ScholarPubMed
Sicilia, T, Niemeyer, HB, Honig, DM & Metzler, M (2003) Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds. J Agric Food Chem 51, 11811188.CrossRefGoogle ScholarPubMed
Valsta, LM, Kilkkinen, A, Mazur, W, Nurmi, T, Lampi, AM, Ovaskainen, ML, Korhonen, T, Adlercreutz, H & Pietinen, P (2003) Phyto-oestrogen database of foods and average intake in Finland. Br J Nutr 89, S31S38.CrossRefGoogle ScholarPubMed
Van Dooren-Flipsen, MMH, Boeijen, I, Van Klaveren, JD, Van Donkersgoed, G (1995) Conversie van consumeerbare voedingsmiddelen naar primaire agrarische producten [in Dutch] Report-95.17 Wageningen, The Netherlands RIKILT.Google Scholar
Vanharanta, M, Voutilainen, S, Lakka, TA, van der, Lee, M, Adlercreutz, H Salonen, JT (1999) Risk of acute coronary events according to serum concentrations of enterolactone: a prospective population-based case-control study. Lancet 354, 21122115.CrossRefGoogle ScholarPubMed
Vanharanta, M, Voutilainen, S, Rissanen, TH, Adlercreutz, H & Salonen, JT (2003) Risk of cardiovascular disease-related and all-cause death according to serum concentrations of enterolactone: Kuopio ischaemic heart disease risk factor study. Arch Intern Med 163, 10991104.CrossRefGoogle ScholarPubMed
Voedingscentrum (1998) Zo eet Nederland; Resultaten van de Voedselconsumptiepeiling 19971998 [in Dutch] The Hague, The Netherlands Voedingscentrum.Google Scholar