foods Foods Foods Foods 2304-8158 MDPI 10.3390/foods2010053 foods-02-00053 Review Lignan Content in Cereals, Buckwheat and Derived Foods Durazzo Alessandra * Zaccaria Maria Polito Angela Maiani Giuseppe Carcea Marina National Research Institute on Food and Nutrition (INRAN), Via Ardeatina 546, 00178, Rome, Italy; E-Mails: zaccaria@inran.it (M.Z.); polito@inran.it (A.P.); maiani@inran.it (G.M.); carcea@inran.it (M.C.) Author to whom correspondence should be addressed; E-Mail: durazzo@inran.it; Tel.: +39-065-149-4651; Fax: +39-065-149-4550. 07 02 2013 03 2013 2 1 53 63 06 12 2012 10 01 2013 31 01 2013 © 2013 by the authors; licensee MDPI, Basel, Switzerland. 2013

This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).

Cereal foods are a fundamental part of a balanced diet and several studies have assigned to wholemeal cereal products a protective role in human health, due to their content of bioactive compounds. Within the phytochemicals, lignans are of increasing interest for their potential anticarcinogenic, antioxidant, estrogenic and antiestrogenic activities. The aim of this work is to contribute to the updating of food lignan databases by providing the profile and the amount of lignans in cereals, buckwheat and several cereal based foods commonly consumed in human diets. Values were taken from published papers. Items were divided in different groups, namely grains, brans and flours, bread, cereal staple foods, breakfast cereals and other cereal products, and values for secoisolariciresinol, matairesinol, pinoresinol, lariciresinol are given. For example, the total average values for the mentioned lignans in grains ranged between 23 μg/100 g and 401 μg/100 g dry weight. The contribution of each single lignan molecule to the total value of lignans appears to be different for every cereal species. Lignan content and typology in processed foods depends on the raw materials used, their degree of refinement and on processing conditions.

lignans cereal grains cereal based foods buckwheat database 1. Introduction

Cereal food products are a fundamental part of a balanced diet and recently several studies have assigned to cereal grains and to wholemeal cereal products in particular a protective role in human health due to their content of bioactive compounds. Bertram et al. [1] conclude that the main protective foods are represented by fiber- and lignan-rich whole-grain cereals, beans, berries, nuts and various seeds.

Within the group of the so called phytochemicals, the phenolic compounds named lignans are attracting the interest of food chemists and nutrition researchers alike. Lignans are vascular plant secondary metabolites, which are attributed a wide range of physiological functions and beneficial properties [2,3,4].

Lignans belong to the group of diphenolic compounds derived from the combination of two phenylpropanoid C6–C3 units at the β and β′ carbon atoms. They have a chemical structure like the 1,4-diarylbutan. They are derived from the shikimic acid biosynthetic pathway [5,6,7]. They are optically active compounds and may exist as two enantiomers, i.e., the right- and left-handed forms [8,9]. Numerous structurally different forms of lignans exist, even if their molecular backbone consists only of two phenylpropane units.

Lignans are contained in edible plants where they occur free or bound to sugars [10]. Several hundred lignans have been discovered in different parts of various plants, including wooden parts, roots, leaves, flowers, fruits and seeds. The plant lignans most commonly detected in foods are lariciresinol, matairesinol, pinoresinol and secoisolariciresinol [11,12]. Other lignans such as medioresinol, syringaresinol, sesamin were reported in various kinds of foods [13,14,15,16]. However, it is important to point out that all lignans present in all foods have never been analysed in any study so far. The main sources of dietary lignans are oilseeds (e.g., flax, soy, rapeseed and sesame), whole-grain cereals (e.g., wheat, oats, rye and barley), legumes and various vegetables and fruits (particularly berries) [11,12,13,14,15,16]. Amongst edible products flaxseed and sesame seeds are rich sources of lignans [11,15,17,18,19], but wood knots in coniferous trees, especially Norway spruce, are the most concentrated lignan sources known so far [20].

Some of the ingested plant lignans are deglycosylated and partly converted to the mammalian lignans enterodiol and enterolactone by colonic bacteria: enterodiol is readily oxidized to enterolactone [21,22,23,24]. These metabolites are then absorbed in the colon and conjugated with glucuronic acid or sulfate in the liver. Some of the metabolites may also undergo enterohepatic circulation. Lignans are excreted in bile and urine as conjugated glucuronides and in feces in the unconjugated form [25,26].

Enterodiol and enterolactone, which are generally called enterolignans due to their colonic origin, have a similar structure to the human hormone estrogen and so may have estrogenic/anti-estrogenic effects. Several epidemiological studies have shown a potential protective effect of the enterolignans or of a lignan-rich diet against the development of various diseases, particularly hormone dependent cancer and cardiovascular diseases [27,28,29,30,31,32,33,34,35,36,37]. The health effect of lignans varied depending on the particular lignan type. It is well known that the physiological activities of compounds are affected by their molecular structures.

The knowledge of the dietary intake of lignans is most notably needed to understand the relationship between a lignan-rich diet and probable prevention of various diseases such as hormone-related cancers, heart diseases, menopausal symptoms and osteoporosis. For this reason, a complete and comprehensive database on the content of lignans in foods is needed [38]. However, the available information has some limitations: many studies focused only on a few compounds, the structural diversity of the compounds, the large number of dietary sources, the large variability in content for a given source, the diversity of extraction techniques and analytical methods used, and, in some cases, the lack of suitable analytical methods [39].

Accurate information on dietary lignan in foods is crucial to determine exposure and to investigate health effects in vivo. Recently, more analytical data on lignans have become available and they could be used to expand food composition databases [11,12,13,14,15,16,40,41,42,43].

The aim of this work is to contribute to the updating of food lignan databases in general, focusing in particular on cereal grains and cereal based foods by gathering and systematizing available data coming from scientific publications. Our list can be a valuable tool for nutritionists, dietitians, medical doctors and scientists in general to estimate the human dietary exposure to lignans coming from the consumption of cereal based foods and in evaluating the effects of cereals consumption in epidemiological studies. Moreover, it is a document stating the state-of-the-art on this topic.

 2. Experimental Section 2.1. Evaluation and Selection of Available Lignan Data

An extensive bibliographical search was conducted using the following keywords: lignans, secoisolariciresinol, lariciresinol, pinoresinol, matairesinol, medioresinol, syringaresinol, cereals and names of individual cereals, cereals based foods and names of individual foods. Having laboratory experience in the determination of lignans we were also aware that the extraction method from the food matrix is an important issue: acid hydrolysis effectively breaks the ester linkages and the glycosidic bonds, but may also affect the molecular structure, causing interconversions between lignans. On the other hand, alkaline hydrolysis is not effective enough in some instances, particularly in strong matrices such as fiber-rich foods, and can lead to underestimation of matairesinol [4,13].

Therefore, an extraction strategy used to determine the amount of dietary lignan in foods was chosen as preferable and publications using that method were selected in order to assure a fair data comparison. The method by Penãlvo et al. [15] that adopts alkaline hydrolysis as the step prior to enzymatic hydrolysis, was chosen. Under alkaline conditions, ester-linked oligomers of lignan are hydrolysed to give the lignan monomer. This method also incorporates isotope dilution to ensure correct accuracy and precision, introducing the utilization of individual stable 13C3-labeled lignans.

Analytical values using isotope dilution as internal standards and either gas or liquid chromatography-mass spectrometry [11,13,14,15,44,45] were considered to be preferable because this was the most sensitive analysis available, having the lowest level of detection. However, values obtained by HPLC were also considered, even if HPLC is less selective and sensitive for the detection of low concentrations of the compounds under study.

 2.2. Database Construction

For easiness of comparison foods were grouped in seven different categories, namely grains, brans and flours, bread, cereal staple foods, breakfast cereals and other cereal products. Grains included barley (Hordeum vulgare L.), buckwheat (Fagopyrum esculentum Moench.), durum wheat (Triticum durum Desf.), emmer (Triticum dicoccon Shrank.), maize (Zea mais L.), oat (Avena sativa L.), rice (Oryza sativa L.), rye (Secale cereale L.), soft wheat (Triticum aestivum L.), spelt (Triticum spelta L.) and triticale (× Triticosecale Wittm).

The average and range values were reported for secoisolariciresinol, matairesinol, lariciresinol, pinoresinol, whether the reported values were on a wet or dry basis, together with other useful information such as origin of samples, genetic background, origin, composition and treatment. Despite syringaresinol and medioresinol are present in cereals and cereal based foods, few data on these lignans are available in the literature [13,14,15,16], as a consequence, sometimes, of restricted standards availability.

 3. Results and Discussion

Cereals, whole grain cereals in particular are an important source of lignans in the human diet [11].

The data presented here (Table 1) are a comprehensive and systematized assessment of lignans in cereals and cereal based products for a more accurate determination of exposure to dietary lignans from foods which are commonly consumed by the population in different countries. For ease of consultation, items are grouped in different categories and are listed in each group in alphabetical order.

foods-02-00053-t001_Table 1

Database of lignans (secoisolariciresinol, matairesinol, lariciresinol, pinoresinol) composition in cereals, buckwheat and derived foods *.

Foods Seco Mat Lari Pino Unit Origin, composition and/or treatment Reference
Grains
Barley 30 3 85 72 μg/100 g wet basis Local markets; dehulled Penãlvo et al. [15]
Barley 28 n.d. 132 45 μg/100 g dry weight Italian farms; 2 cultivars; dehulled Durazzo et al. [40]
Buckwheat 131 1 362 92 μg/100 g wet basis Local markets Penãlvo et al. [15]
Durum wheat n.d. n.d. 76 n.d. μg/100 g dry weight Italian farms; 2 cultivars Durazzo et al. [40]
Emmer 29 n.d. 104 n.d. μg/100 g dry weight Italian farms; 2 cultivars Durazzo et al. [40]
Maize 12 n.d. 11 0 μg/100 g dry weight Italian farms; 3 cultivars Durazzo et al. [40]
Millet 67 3 20 85 μg/100 g wet basis Local markets Penãlvo et al. [15]
Oat 19 71 183 194 μg/100 g wet basis Local markets Penãlvo et al. [15]
Oat n.d. n.d. 97 304 μg/100 g dry weight Italian farms; 2 cultivars; dehulled Durazzo et al. [40]
Oat 6–13 0–104 340–599 214–683 μg/100 g wet basis Fifty-five spring oat samples of 5 different cultivars Smeds et al. [14]
Rice 15 n.d. 128 29 μg/100 g dry weight Italian farms; 3 cultivars Durazzo et al. [40]
Rye 38 27 324 381 μg/100 g wet basis Local markets Penãlvo et al. [15]
Rye 25 n.d. 100 n.d. μg/100 g dry weight Italian farms; 2 cultivars Durazzo et al. [40]
Rye 10–29 18–45 76–177 176–313 μg/100 g wet basis Twenty-eight winter rye samples of 6 different cultivars Smeds et al. [14]
Soft wheat n.d. n.d. 58 n.d. μg/100 g dry weight Italian farms; 2 cultivars Durazzo et al. [40]
Soft Wheat 35 3 62 37 μg/100 g wet basis Local markets Penãlvo et al. [15]
Soft Wheat 20–43 n.d. 45–95 53–83 μg/100 g wet basis Seventy-three spring wheat samples of 9 different cultivars Smeds et al. [14]
Spelt 26 n.d. 83 n.d. μg/100 g dry weight Italian farms; 2 cultivars Durazzo et al. [40]
Triticale n.d. n.d. 58 n.d. μg/100 g dry weight Italian farms; 2 cultivars Durazzo et al. [40]
Brans and flours
Durum wheat bran n.d. n.d. 220 181 μg/100 g dry weight Two cultivars Durazzo et al. [41]
Soft wheat bran 370 n.d. 459 386 μg/100 g dry weight One cultivar Durazzo et al. [41]
Soft wheat 31 0 140 38 μg/100 g wet basis Supermarkets; wholemeal Milder et al. [11]
Soft wheat 0 0 18 9 μg/100 g wet basis Supermarkets; whiteflour Milder et al. [11]
Soft wheat 16 n.d. 34 n.d. μg/100 g dry weight Supermarkets; whiteflour Durazzo et al. [43]
Bread
Currant/raisin 9 7 79 9 μg/100 g wet basis Two supermarkets and a local bakery Milder et al. [11]
Flaxseed (whole) 11,845 26 220 383 μg/100 g wet basis Two supermarkets and a local bakery Milder et al. [11]
Flaxseed 7208 0 29 2 μg/100 g wet basis Dempsters; pre-sliced Thompson et al. [12]
Multi-grains 6163 19 185 377 μg/100 g wet basis Two supermarkets and a local bakery Milder et al. [11]
Multi-grains 4770 1 10 4 μg/100 g wet basis Dempsters; pre-sliced Thompson et al. [12]
Oat 7 0 4 11 μg/100 g wet basis Wheat and oats with honey; pre-sliced Thompson et al. [12]
Rye (dark type) 13 14 122 172 μg/100 g wet basis Two supermarkets and a local bakery Milder et al. [11]
Rye (light type) 16 12 111 163 μg/100 g wet basis Two supermarkets and a local bakery Milder et al. [11]
Rye 122 0 11 9 μg/100 g wet basis Jagdschnitten hunter style, Dimpflmeier; pre-sliced Thomson et al. [12]
Rye 33 4 47 44 μg/100 g wet basis Local markets in Tokio; (50% rye) Penãlvo et al. [16]
Rye 7 1 18 16 μg/100 g wet basis Local markets in Tokio; (30% rye) Penãlvo et al. [16]
Sesame 3 0 8 42 μg/100 g wet basis Dempsters; pre-sliced Thompson et al. [12]
Wheat (whole type) 3 0 5 1 μg/100 g wet basis Original 100%, Dempsters; pre-sliced Thompson et al. [12]
Wheat (whole type) 15 0 73 33 μg/100 g wet basis Two supermarkets and a local bakery Milder et al. [11]
Wheat (refined type) 17 0 38 28 μg/100 g wet basis Two supermarkets and a local bakery Milder et al. [11]
Wheat (white type) 0 0 11 7 μg/100 g wet basis Two supermarkets and a local bakery Milder et al. [11]
Wheat (white type) 1 0 2 1 μg/100 g wet basis Enriched, Wonder; pre-sliced Thompson et al. [12]
Cereals staple foods
Couscous (cooked) 2 n.d. 0 n.d. μg/100 g wet basis President’s choice; cooked in water Thompson et al. [12]
Macaroni (cooked) 4 0 7 5 μg/100 g wet basis White, boiled Milder et al. [11]
Rice (cooked) 3 2 28 7 μg/100 g wet basis Supermarket; whole grain, boiled Milder et al. [11]
Rice (cooked) 0 0 7 0 μg/100 g wet basis Supermarket; white, boiled Milder et al. [11]
Rice (cooked) 0 0 3 1 μg/100 g wet basis White, converted long grain, Uncle Ben’s; cooked in water Thompson et al. [12]
Semolina pasta (raw) 22 n.d. 26 27 μg/100 g dry weight Market; three different brands Durazzo et al. [41]
Breakfast cereals
Brand 1 7 n.d. 79 69 μg/100 g dry weight Market; cereals 48.4% (whole oat flour 35.8%; maize flour), wheat germ Durazzo et al. [41]
Brand 2 20 n.d. 97 131 μg/100 g dry weight Market; whole cereals (54%) (flour of whole oat, whole rice, whole wheat), cereal agglomerate (19%), oat bran, barley malt Durazzo et al. [41]
Brand 3 n.d. n.d. 99 187 μg/100 g dry weight Market; cornflakes and bran (31.5%), toasted oatmeal (30%), rice aggregate and bran (25%), sugar-coated barley flakes (9%), almonds (4.5%) Durazzo et al. [41]
Cheerios 9 1 3 0 μg/100 g wet basis General Mills Thompson et al. [12]
Muesli 17 0 250 497 μg/100 g wet basis Jordans, crunchy Milder et al. [11]
Muesli 13 0 120 210 μg/100 g wet basis Albert Heijn, basic Milder et al. [11]
Muesli 17 0 63 129 μg/100 g wet basis Edah, crunchy Milder et al. [11]
Oatmeal 1 0 4 2 μg/100 g wet basis Dempsters; quick cooking, boiled in water Thompson et al. [12]
Raisin Bran 15 0 17 1 μg/100 g wet basis Kellogg’s Thompson et al. [12]
Other cereal products
Compressed puffed rice 23 n.d. 82 22 μg/100 g dry weight Market; white rice and dehulled rice Durazzo et al. [41]
Puffed barley 26 n.d. 143 48 μg/100 g dry weight Market; whole barley Durazzo et al. [41]
Wholegrain biscuits 28 n.d. 25 23 μg/100 g dry weight Market; wheat flour (51%), barley flakes (3%), rye flakes (1.8%), rice flour (1.7%), oatmeal (1.3%), maize flour (1.2%), wheat malt Durazzo et al. [41]
Granola bar 3 2 8 14 μg/100 g wet basis Nature Valley, with almond Thompson et al. [12]

* Seco = Secoisolariciresinol; Mat = Matairesinol; Lari = Lariciresinol; Pino = Pinoresinol; n.d. = not detectable.

Among grains, Durazzo et al. [40] showed that dehulled oat and barley reached the highest values (by summing up the analysed lignans) amongst the 10 reported cereal species, 401 and 206 μg/100 g dry weight, respectively. A great variability was observed with regard to lignan typology and content also within the same species.

In fact, the content of some lignans and the degree of esterification of the same lignan glycosides may vary within the same cereal species as a consequence of different growing conditions, geographic location, climate, and genetic characteristics [11,13,14]. In fact, agronomic, environmental and post-harvest factors influence, in different ways, not only different classes of chemical compounds but also structurally different compounds belonging to the same chemical subgroup [46]. However, in most of the studied grains the predominant compound amongst the reported lignans was lariciresinol [14,15,40].

Many grains are consumed daily in a number of products from around the world. The health benefits of cereal products are an emergent part of the health related food market. Grains undergo different kinds of processing to obtain desirable products with optimized flavor, color, texture and appearance as well as shelf life. Few results are reported in the literature regarding the effects of cereal processing technologies such as milling, baking, extrusion, etc. on lignans content in most foods.

Regarding flours, considering that lignans are mainly located in the grain outer layers [13,47,48], it is understandable that wholemeal flour is richer in lignans than refined flours. The same difference was observed in whole wheat bread with respect to refined wheat bread in both the investigations of Milder et al. [11] and Thompson et al. [12].

Miur and Westcott [49] reported that secoisolariciresinol diglucoside was stable in the bread making process. In particular, it could withstand the higher temperatures in the core during baking. Simbalista et al. [50], by investigating the effect of bread making on a product containing flaxseed, have shown that, after baking, 89% of the original lignan content was kept in bread.

Among bakery products, besides those containing flaxseed and multi-grains, rye bread represents a good source of all different lignans [11,12,16].

Regarding breakfast cereals, Milder et al. [11] found a range between 209 and 764 μg/100 g wet basis considering the sum of lariciresinol, secoisolariciresinol and pinoresinol. Durazzo et al. [41] found a range of total lignan content (same as above) from 154 to 286 μg/100 g dry weight. Lariciresinol and pinoresinol were found at higher concentrations with respect to secoisolariciresinol in most of the items. Obviously, the different raw materials used and their degree of refinement are mainly responsible for the different lignan concentrations in breakfast cereals but, in general, they are a good source of lignans.

As regards the cereals staple foods group, pasta is recognized all over the world as an ingredient of traditional meals, especially in the Mediterranean regions [51]. Recent statistics indicate that 26 kg/person of pasta are yearly consumed in Italy [52]. In raw Italian semolina pasta, total lignan content (i.e., the sum of secoisolariciresinol, lariciresinol and pinoresinol) was reported to be 76 μg/100 g dry weight [41]. The concentration of lignans in pasta is relevant considering that pasta is a staple food in the diet of some populations and it is consumed daily.

Pasta undergoes cooking before consumption so it is also important to consider the influence of domestic cooking on the lignans present in the raw pasta. Milder et al. [11] reported for cooked macaroni, cooked white rice and cooked whole rice values of total lignan content of 16, 7 and 40 μg/100 g wet basis, respectively.

As regards other cereal products, puffed barley represents a good source of lignans and the most representative component amongst the identified lignans is lariciresinol [41]. The level of total lignans (i.e., the sum of secoisolariciresinol, lariciresinol and matairesinol) in puffed barley matched that observed in dehulled barley grains. So, again, the raw material and its degree of refining determines mainly the amount of bioactive substances, lignans in particular, which are found in raw processed foods.

This database, which is limited and can be updated as new data become available, can nevertheless for the time being be useful for several purposes such as understanding the potential effects of specific lignans in epidemiological studies or estimating the human dietary exposure to lignans coming from cereal based foods.

 Acknowledgments

This work was undertaken within the project CERSUOM, financed by the Italian Ministry of Agriculture. The authors would like to thank Mr. Francesco Martiri for his secretarial help in this project.

 Conflict of Interest

The authors declare no conflict of interest.

 References Bertram H.C. Bach Knudsen K.E. Serena A. Malmendal A. Nielsen N.C. Fretté X.C. Andersen H.J. NMR-based metabonomic studies reveal changes in the biochemical profile of plasma and urine from pigs fed high-fibre rye bread Br. J. Nutr. 2006 95 955 962 10.1079/BJN20061761 Adlercreutz H. Lignans and human health Crit. Rev. Clin. Lab. Sci. 2007 44 483 525 10.1080/10408360701612942 Miur A.D. Flax lignans: New opportunities for functional foods Food Sci. Technol. Bull. Funct. Foods 2010 6 61 79 10.1616/1476-2137.15817 Peterson J. Dwyer J. Adlercreutz H. Scalbert A. Jacques P. McCullough M.L. Dietary lignans: Physiology and potential for cardiovascular disease risk reduction Nutr. Rev. 2010 68 571 603 10.1111/j.1753-4887.2010.00319.x Ayres D.C. Loike J.D. Lignans Chemical, Biological and Clinical Properties Chemistry & Pharmacology of Natural Products Phillipson J.D. Ayres D.C. Baxter H. Cambridge University Press Cambridge, UK 1990 402 Mazur W.M. Adlercreutz H. Natural and anthropogenic environmental estrogens: The scientific basis for risk assessment; naturally occurring estrogens in food Pure Appl. Chem. 1998 70 1759 1776 10.1351/pac199870091759 Imai T. Nomura M. Fukushima K. Evidence for involvement of the phenylpropanoid pathway in the biosynthesis of the norlignan agatharesinol J. Plant Physiol. 2006 163 483 487 10.1016/j.jplph.2005.08.009 Hemmati S. Heimendahl C.B. Klaes M. Alfermann A.W. Schmidt T.J. Fuss E. Pinoresinol-lariciresinol reductases with opposite enantiospecificity determine the enantiomeric composition of lignans in the different organs of Linum usitatissimum L Planta Med. 2010 76 928 934 10.1055/s-0030-1250036 Umezawa T. Diversity in lignan biosynthesis Phytochem. Rev. 2003 2 371 390 10.1023/B:PHYT.0000045487.02836.32 Saleem M. Kim H.J. Ali M.S. Lee Y.S. An update on bioactive plant lignans Nat. Prod. Rep. 2005 22 696 716 10.1039/b514045p Milder I.E. Arts I.C. van de Putte B. Venema D.P. Hollman P.C. Lignan contents of Dutch plant foods: A database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol Br. J. Nutr. 2005 93 393 402 10.1079/BJN20051371 Thompson L.U. Boucher B.A. Liu Z. Cotterchio M. Kreiger N. Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans and coumestan Nutr. Cancer 2006 54 184 201 10.1207/s15327914nc5402_5 Smeds A.I. Eklund P.C. Sjöholm R.E. Willför S.M. Nishibe S. Deyama T. Holmbomet B.R. Quantification of a broad spectrum of lignans in cereals, oilseeds, and nuts J. Agric. Food Chem. 2007 55 1337 1346 10.1021/jf0629134 Smeds A.I. Jauhiainen L. Tuomola E. Peltonen-Sainio P. Characterization of variation in the lignan content and composition of winter rye, spring wheat and spring oat J. Agric. Food Chem. 2009 57 5837 5842 10.1021/jf9004274 Peñalvo J.L. Haajanen K.M. Botting N. Adlercreutz H. Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry J. Agric. Food Chem. 2005 53 9342 9347 10.1021/jf051488w Peñalvo J.L. Adlercreutz H. Uehara M. Ristimaki A. Watanabe S. Lignan content of selected foods from Japan J. Agric. Food Chem. 2008 56 401 409 10.1021/jf072695u18163563 Thompson L.U. Robb P. Serraino M. Cheung F. Mammalian lignan production from various foods Nutr. Cancer 1991 16 43 52 10.1080/01635589109514139 Mazur W. Phytoestrogen content in foods Baillieres Clin. Endocrinol. Metab. 1998 12 729 742 10.1016/S0950-351X(98)80013-X Muir A.D. Westcott N.D. Flaxseed Constituents and Human Health Flax: the Genus Linum Muir A.D. Westcott N.D. Taylor & Francis London, UK 2003 243 251 Holmbom B. Eckerman C. Eklund P. Hemming J. Nisula L. Reunanen M. Sjöholm R. Sundberg A. Sundberg K. Willför S. Knots in trees—A new rich source of lignans Phytochem. Rev. 2003 2 331 340 10.1023/B:PHYT.0000045493.95074.a8 Axelson M. Sjövall J. Gustafsson B.E. Setchell K.D.R. Origin of lignans in mammals and identification of a precursor from plants Nature 1982 298 659 660 10.1038/298659a0 Borriello S.P. Setchell K.D.R. Axelson M. Lawson A.M.J. Production and metabolism of lignans by the human faecal flora Appl. Bacteriol. 1985 58 37 43 10.1111/j.1365-2672.1985.tb01427.x Setchell K.D.R. Adlercreutz H. Mammalian Lignans and Phytoestrogens: Recent Studies on Their Formation, Metabolism and Biological Role in Health and Disease Role of Gut Flora in Toxicity and Cancer Rowland I. R. Academic Press San Diego, CA, USA 1988 315 345 Rowland I. Wiseman H. Sanders T. Adlercreutz H. Bowey E. Interindividual variation in metabolism of isoflavonoids and lignans: The role of the gut microflora and habitual diet Nutr. Cancer 2000 36 27 32 10.1207/S15327914NC3601_5 Heinonen S. Nurmi T. Liukkonen K. Poutanen K. Wähälä K. Deyama T. Nishibe S. Adlercreutz H. In vitro metabolism of plant lignans: New precursors of mammalian lignans enterolactone and enterodiol J. Agric. Food Chem. 2001 49 3178 3186 10.1021/jf010038a Penãlvo J.L. Nurmi T. Haajanen K. Al-Maharik N. Botting N. Adlercreutz H. Determination of lignans in human plasma by liquid chromatography with coulometric electrode array detection Anal. Biochem. 2004 332 384 393 10.1016/j.ab.2004.05.046 Webb A.L. McCullough M.L. Dietary lignans: Potential role in cancer prevention Nutr. Cancer 2005 51 117 131 10.1207/s15327914nc5102_1 Bergman Jungestrom M. Thompson L.U. Dabrosin C. Flaxseed and its lignans inhibit estradiol-induced growth, angiogenesis, and secretion of vascular endothelial growth factor in human breast cancer xenografts in vivo Clin. Cancer Res. 2007 13 1061 1067 10.1158/1078-0432.CCR-06-1651 Saarinen N.M. Warri A. Airio M. Smeds A. Makela S. Role of dietary lignans in the reduction of breast cancer risk Mol. Nutr. Food Res. 2007 51 857 866 10.1002/mnfr.200600240 Bloedon L.T. Balikai S. Chittams J. Cunnane S.C. Berlin J.A. Rader D.J. Szapary P.O. Flaxseed and cardiovascular risk factors: Results from a double blind, randomized, controlled clinical trial J. Am. Coll. Nutr. 2008 27 65 74 18460483 Prasad K. Flaxseed and cardiovascular health J. Cardiovasc. Pharmacol. 2009 54 369 377 10.1097/FJC.0b013e3181af04e5 Velentzis L.S. Cantwell M.M. Cardwell C. Keshtgar M.R. Leathem A.J. Woodside J.V. Lignans and breast cancer risk in pre- and post-menopausal women: Meta-analyses of observational srudies Br. J. Cancer 2009 100 1492 1498 10.1038/sj.bjc.6605003 Adolphe J.L. Whiting S.J. Juurlink B.H. Thorpe L.U. Alcorn J. Health effects with consumption of the flax lignan secoisolariciresinol diglucoside Br. J. Nutr. 2010 103 929 938 10.1017/S0007114509992753 Saarinen N.M. Tuominen J. Pylkkänen L. Santti R. Assessment of information to substantiate a health claim on the prevention of prostate cancer by lignans Nutrients 2010 2 99 115 10.3390/nu2020099 Buck K. Zaineddin A.K. Vrieling A. Linseisen J. Chang-Claude J. Meta-analyses of lignans and enterolignans in relation to breast cancer risk Am. J. Clin. Nutr. 2010 92 141 153 10.3945/ajcn.2009.28573 Buck K. Vrieling A. Zaineddin A.K. Becker S. Hüsing A. Kaaks R. Linseisen J. Flesch-Janys D. Chang-Claude J. Serum enterolactone and prognosis of postmenopausal breast cancer J. Clin. Oncol. 2011 29 3730 3738 10.1200/JCO.2011.34.647821900115 Ward H.A. Kuhnle G.G. Mulligan A.A. Lentjes M.A. Luben R.N. Khaw K.T. Breast, colorectal, and prostate cancer risk in the European Prospective Investigation into Cancer and Nutrition-Norfolk in relation to phytoestrogen intake derived from an improved database Am. J. Clin. Nutr. 2010 91 440 448 10.3945/ajcn.2009.28282 Blitz C.L. Murphy S.P. Au D.L.M. Adding lignan values to a food composition database J. Food Comp. Anal. 2007 20 99 105 10.1016/j.jfca.2006.05.006 Scalbert A. Andres-Lacueva C. Arita M. Kroon P. Manach C. Urpi-Sarda M. Wishart D. Databases on food phytochemicals and their health-promoting effects J. Agric. Food Chem. 2011 59 4331 4348 10.1021/jf200591d21438636 Durazzo A. Raguzzini A. Azzini E. Foddai M.S. Narducci V. Maiani G. Carcea M. Bioactive molecules in cereals Tecnica Molitoria Int. 2009 60 150 162 Durazzo A. Azzini E. Raguzzini A. Maiani G. Finocchiaro F. Ferrari B. Gianinetti A. Carcea M. Influence of processing on the lignans content of cereal based foods Tecnica Molitoria Int. 2009 60 163 173 Moreno-Franco B. Garcia-Gonzalez A. Montero-Bravo A.M. Iglesias-Gitierrez E. Ubeda N. Maroto-Nunez L. Adlercreutz H. Penãlvo J. Dietary alkylresorcinols and lignans in the spanish diet: Development of the Alignia database J. Agric. Food Chem. 2011 59 9827 9834 10.1021/jf201544621815609 Durazzo A. Turfani V. Azzini E. Maiani G. Carcea M. Phenols, lignans and antioxidant properties of legume and sweet chestnut flours Food Chem. 2012 in press Mazur W. Fotsis T. Wahala K. Ojala S. Salakka A. Adlercreutz H. Isotope diluition gas chromatographic-mass spectrometric method for the determination of isoflavonoids, coumestrol, and lignans in food samples Anal. Biochem. 1996 233 169 180 10.1006/abio.1996.0025 Horn-Ross P.L. Barnes S. Lee M. Coward L. Mandel J.E. Koo John E.M. Smith M. Assessing phytoestrogen exposure in epidemiologic studies: Development of a database (United States) Cancer Causes Control 2000 11 289 298 10.1023/A:100899560669910843440 Amarowicz R. Carle R. Dongowski G. Durazzo A. Galena R. Kammerer D. Maiani G. Piskula M.K. Influence of postharvest processing and storage influences on phenolic acids and flavonoid in foods Mol. Nutr. Food Res. 2009 53 S151 S183 10.1002/mnfr.200700486 Adlercreutz H. Mazur W. Phyto-oestrogens and Western diseases Ann. Med. 1997 29 95 120 9187225 Esposito F. Arlotti G. Bonifati A.M. Napolitano A. Vitale D. Fogliano V. Antioxidant activity and dietary fibre in durum wheat bran by-products Food Res. Int. 2005 38 1167 1173 10.1016/j.foodres.2005.05.002 Muir A.D. Westcott N.D. Quantitation of the lignan secoisolariciresinol diglucoside in baked goods containing flax seed or flax meal J. Agric. Food Chem. 2000 48 4048 4052 10.1021/jf990922p Simbalista R.L. Frota K. Soares R.A.M. Arêas J.A.G. Effect of storage and processing of Brazilian flaxseed on lipid and lignan contents Ciênc. Tecnol. Aliment. 2012 32 374 380 Krishnan M. Prabhasankar P. Health based pasta: Redefining the concept of the next generation convenience food Crit. Rev. Food Sci. Nutr. 2012 52 9 20 10.1080/10408398.2010.486909 AIDEPI Available online:www.aidepi.it (accessed on 31 January 2013)