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Phytoestrogen content in cereals and cereal-based foods a (Continued) Isoflavones Lignans Food Daidzein Genistein Glycitein Biochanin A Formononetin Secoisolariciresinol Matairesinol Coumestrol
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Dietary phytoestrogens may be involved in the occurrence of chronic diseases. Reliable information on the phytoestrogen content in foods is required to assess dietary exposure and disease risk in epidemiological studies. However, there is little information on isoflavone, lignan, and coumestrol content of cereals and cereal-based foods, leading to...
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The absorption of isoflavones varies substantially among individuals. It is unknown whether isoflavone absorption differs between those originating from soy and those from red clover, which contain different mixtures of isoflavones. Because both soy and red clover are increasingly used in foods and supplements, these issues were studied in 14 subje...
Phytoestrogens are plant-derived compounds having similar effects to estrogens. Several phytostrogen groups have been identified being the most characteristics the isoflavones like genistein, coumestans like coumestrol, and lignans represented by the enterolactone. Depending on the doses, they can act as agonists or antagonists of steroidal hormone...
Phytoestrogens are plant-derived compounds having similar effects to estrogens. Several phytostrogen groups have been identified being the most characteristics the isoflavones like genistein, coumestans like coumestrol, and lignans represented by the enterolactone. Depending on the doses, they can act as agonists or antagonists of steroidal hormone...
Phytoestrogens are a group of non-steroidal secondary plant metabolites with structural and functional similarity to 17β-oestradiol. Urinary and plasma phytoestrogens have been used as biomarkers for dietary intake, however, this is often not possible in large epidemiological studies or to assess general exposure in free-living individuals. Accurat...
Citations
... No published datasets were found for lignans, alkylresorcinols or phenolic acids in Australian products, but datasets were located for similar cereals and cereal products mainly from Europe, Canada and the UK 11,14,[55][56][57][58][59][60][61][62][63] (see Additional File 1). These data met the inclusion criteria for this study, values contained were all derived using chromatography, and have previously been used by other published studies developing ad-hoc databases 53,[64][65][66] . ...
Cereal foods are consumed globally and are important sources of polyphenols with potential health benefits, yet dietary intakes are unclear. We aimed to calculate the dietary intakes of polyphenols from cereal foods in the Melbourne Collaborative Cohort Study (MCCS), and describe intakes by demographic and lifestyle factors. We estimated intakes of alkylresorcinols, lignans and phenolic acids in n = 39,892 eligible MCCS participants, using baseline dietary data (1990–1994) from a 121-item FFQ containing 17 cereal foods, matched to a polyphenol database developed from published literature and Phenol-Explorer Database. Intakes were estimated within groups according to lifestyle and demographic factors. The median (25th–75th percentile) intake of total polyphenols from cereal foods was 86.9 mg/day (51.4–155.8). The most consumed compounds were phenolic acids, with a median intake of 67.1 mg (39.5–118.8), followed by alkylresorcinols of 19.7 mg (10.8–34.6). Lignans made the smallest contribution of 0.50 mg (0.13–0.87). Higher polyphenol intakes were associated with higher relative socio-economic advantage and prudent lifestyles, including lower body mass index (BMI), non-smoking and higher physical activity scores. The findings based on polyphenol data specifically matched to the FFQ provide new information on intakes of cereal polyphenols, and how they might vary according to lifestyle and demographic factors.
... These foods are part of the food culture of the Colombian population, with a high caloric intake and are easy to acquire, due to their wide availability and low economic cost [21,22]. On the other hand, it has been shown that the consumption of whole grains containing bioactive components such as dietary fiber, resistant starch, vitamins, minerals and phytoestrogens [23,24], and the consumption of fruits and vegetables, are related to the control and reduction of the risk of cancer, hypertension, diabetes mellitus, obesity and other cardiovascular diseases [25,26]. According to Afshin et al., the average consumption of fruits worldwide is two-thirds of the minimum recommended amounts [27]. ...
The selection of food depends on various factors such as cultural, social, economic and biological. This paper determines the factors associated with dietary patterns in Colombia. It is an observational, descriptive exploratory study collecting secondary data from the National Survey of Nutritional Status of Colombia (ENSIN, 2015) of 16,216 people between 15 and 64 years of age. The variables were the following: area, age range, sex, educational level, high blood pressure arterial hypertension (HTA), diabetes (DM), cancer, wealth quartile and dietary pattern. For the data analysis, logistic regression models were generated for each pattern and OR was used as a measure of association. Of those studied, 74.6% live in urban areas, all were aged between 15 and 49 years and 45.4% were in the first wealth quartile (Q1). There was a greater probability of traditional and conservative dietary patterns in people with diabetes and hypertension. Consumption of the conservative pattern was associated with being a woman, while consumption of the traditional pattern was associated with people in the first and second wealth level. Consumption of grill/beverage was more likely in men. Socio-demographic factors and chronic non-communicable diseases are associated with dietary patterns. This makes it relevant for health professionals to take into account these characteristics for nutritional interventions.
... As anticipated, the number of wheat-derived metabolites was significantly lower [55,56], with a 10-20% rate of occurrence for phenolic acids, including neochlorogenic, chlorogenic, caffeic and protocatechuic acids. Only diosmetin displayed an occurrence rate that reached the 80% mark. ...
The intensive use of plant materials as a sustainable alternative for fish feed production, combined with their phytochemical content, which affects the growth and production characteristics of farmed fishes, necessitates their monitoring for the presence of raw materials of plant origin. This study reported herein concerns the development, validation and application of a workflow using high-performance liquid chromatography combined with tandem mass spectrometry (LC-MS/MS) for the quantification of 67 natural phytoestrogens in plant-derived raw materials that were used to produce fish feeds. Specifically, we verified the presence of 8 phytoestrogens in rapeseed meal samples, 20 in soybean meal samples, 12 in sunflower meal samples and only 1 in wheat meal samples in quantities enabling their efficient incorporation into clusters. Among the various constituents, the soybean phytoestrogens daidzein, genistein, daidzin, glycitin, apigenin, calycosin and coumestrol, as well as the sunflower neochlorogenic, caffeic and chlorogenic phenolic acids, displayed the highest correlations with their origin descriptions. A hierarchical cluster analysis of the studied samples, based on their phytoestrogen contents, led to the efficient clustering of raw materials. The accuracy and efficiency of this clustering were tested through the incorporation of additional samples of soybean meal, wheat meal and maize meal, which verified the utilization of the phytoestrogen content as a valuable biomarker for the discrimination of raw materials used for fish feed production.
... Document SD2: Example of the informed consent form (translated in English). References [50][51][52][53][54][55][56][57][58][59][60] are cited in the supplementary materials. Informed Consent Statement: Informed consent was obtained from all subjects involved in the study. ...
Phytoestrogens are dietary compounds with low estrogenic activity. The two main categories in the French diet are isoflavones from pulses and enterolignans metabolized by the gut flora from various lignans found in fruits, vegetables, grains, and beverages. Isoflavones and lignans have different effects on human physiology and can antagonize each other. Comprehensive lists of phytoestrogen sources were constructed based on measurements and literature data. The 24 h and 48 h dietary recalls were proposed to the volunteers of the ISOLED cohort (NCT03421184). Urine and plasma samples from these volunteers were assayed for genistein, daidzein, equol, and enterolactone. A dietary score was constructed considering the pharmacokinetic characteristics of these compounds. Correlation analyses were applied to fluid concentrations associated with dietary scores. Pearson correlations reached 0.921 (p < 0.001) for urineIF, 0.900 (p < 0.001) for plasmaIF, 0.764 (p < 0.001) for urineENL, and 0.723 (p < 0.001) for plasmaENL. ELISAs associated with careful intake assessments proved to be good tools for phytoestrogens’ exposure estimation.
... They are found in certain foods and can replace to some extent the effects of estrogen that is decreased with menopause. Phytoestrogens mimic the functions of estrogens on females' body (Kuhnle et al. 2009). It is well known that soya products are good source of phytoestrogen (Barrette 2006), and eating bakery product prepared from soya flour helps in ameliorating the severity of various menopausal symptoms (Fouad et al. 2018). ...
Background
Nutrition and good health are two dependent parallel axes; female’s health at different ages in general and at the time of menopause in particular has received a lot of attention last several years. The objective of this experimental study was to evaluate the effect of consuming food supplement versus lifestyle modification in the dietary habit on menopausal symptoms in perimenopausal Egyptians females.
Results
Forty seven females in the perimenopausal stage of life with mean age 46.04 ± 5.88 years participated on the food supplement consumption group, they consumed 75 g per day of a rusk (prepared from corn flour, wheat flour 72%, full cream milk powder, flaxseed oil, wheat germ, clove and cinnamon powder) for 2 months. They were compared with the control group (forty nine females with mean age 46.91 ± 5.39 years) who changed their foods habits to a healthy life style. Menopause rating scale and the biochemical analysis were comparable on day 1 and on day 60. The total menopause rating scale and its three subscales (psychological, urogenital and somatic), waist circumference, serum follicle stimulating hormone and estradiol in the corn rusk supplement group showed a statistically significant improvement. No significant difference was noted in the control group apart of the psychological subscale and waist circumference.
Conclusions
Corn Rusk enriched with clove and cinnamon as a food supplement snake is promising to relief menopausal symptoms and should be considered on the diet of menopausal females.
... Phenol-Explorer [17] is the most comprehensive database on polyphenols that include all individual lignans (n ~ 30) present in habitual foods. Other studies have used other food composition databases from Canada [18], the Netherlands [19], UK [20][21][22] and Finland [23]; although these only usually include the four main individual lignans. The main limitations of using these databases are a large amount of unknown values, the limited quantity of food items included, and the absence of composition data on cooked foods. ...
Dietary lignans are phytoestrogens that are mostly found in plant-based foods, especially whole grains, seeds, nuts, legumes and vegetables. An accurate assessment of lignan exposure is crucial to evaluate their potential health benefits and to establish future recommendations and dietary guidelines. This narrative review aimed to (i) summarize the pros and the cons of the current main assessment methods for lignan exposure─i.e., dietary questionnaires, food composition tables and biomarkers, (ii) describe the individual lignans more consumed from a worldwide perspective, as well as their main food sources, (iii) determine the lignans concentrations in both urine and blood, and explore their heterogeneity among countries, and finally (iv) discuss the main determinants of lignan exposure.
... Active aglycones must be released through hydrolysis during sample extraction, e.g. mediated by a pH change (Kuhnle et al. 2009;Hostetler et al. 2017). While this does also occur when whole grain cereals are consumed, there is no indication of adverse effects at the phytoestrogen levels which naturally occur in food, supported by a long history of safe human consumption (at least since humankind first began to grow grain crops in about 10,000 BC) (UK-COT 2003;AFSSA 2005;Cekici 2018; Global Burden of Diseases, Injuries, and Risk Factors Study 2017 Diet Collaborators 2019). ...
The idea that previously unknown hazards can be readily revealed in complex mixtures such as foods is a seductive one, giving rise to the hope that data from effect-based assays of food products collected in market surveys is of suitable quality to be the basis for data-driven decision-making. To study this, we undertook a comparative study of the oestrogenicity of blinded cereal samples, both in a number of external testing laboratories and in our own facility. The results clearly showed little variance in the activities of 9 samples when using a single method, but great differences between the activities from each method. Further exploration of these findings suggest that the oestrogenic activity is likely an inherent part of the natural food matrix which the varying sample preparation methods are able to release and extract to differing degrees. These issues indicate the current poor suitability of these types of datasets to be used as the basis for consumer advice or food decision-making. Data quality must be improved before such testing is used in practice. ARTICLE HISTORY
... The recent work of Durazzo et al. (2018) well summarized the occurrence of lignans in food groups and existing lignan databases at European level. As reported by Durazzo et al. (2018), the main sources of dietary lignans are oilseeds such as flax, soy, rapeseed, and sesame; wholegrain cereals such as wheat, oats, rye, and barley; legumes; various vegetables and fruits (particularly berries); beverages (i.e., coffee, tea, and wine); and, recently, lignans are also determined in dairy products, meat, and fish (Valsta et al., 2003;Milder et al., 2005a;Milder et al., 2005b;Peñalvo et al., 2005;Thompson et al., 2006;Penalvo et al., 2007;Kuhnle et al., 2008a;Kuhnle et al., 2008b;Durazzo et al., 2009;Kuhnle et al., 2009a;Kuhnle et al., 2009b;Smeds et al., 2009;Moreno-Franco et al., 2011;Smeds et al., 2012;Durazzo et al., 2013a;Durazzo et al., 2013b;Mulligan et al., 2013;Durazzo et al., 2014b;Turfani et al., 2017;Angeloni et al., 2018;Angeloni et al., 2019). ...
Lignans encompass a large and complex group of phytochemicals widely distributed throughout terrestrial plant lineages. Lignans play important roles in both plant ecology (interactions with and adaptation to an ever-changing environment) and physiology/ development. As their specialized metabolite nature might suppose, lignans have been related to plant defense against a number of herbivores and microorganisms. For example, their constitutive deposition helps impart durability, longevity, and resistance to the heartwoods of many tree species against wood-rotting fungi, therefore acting as phytoanticipins. Lignans can also act as phytoalexins, being synthesized de novo by plants accumulating quickly at areas of pathogen or herbivore attack. However, the precise roles in planta and the ecological significances of most lignans are still not well established.
As for many biologically active compounds originating from plants, lignan exploration has not been restricted solely to the plant research field but has also triggered intensive studies in the fields of human diet and/or health research over the last decades. Some lignans, belonging to the phytoestrogen class are converted, upon ingestion, by human gastrointestinal microbiota into the mammalian lignans enterodiol and enterolactone. The latter display the well-described chemopreventive properties against various tumors (such as breast, colon and prostate cancers) or cardiovascular disorders, whereas some other studies also report their roles in preventing diabetes. Other lignans are already used in pharmacy and medicine such as podophyllotoxin, the natural starting compound for the synthesis of lead anticancer drugs (Etoposide, Teniposide, Etopophos). However, many questions remain concerning i) their bioconversion, pharmacokinetic, and molecular targets, etc. and ii) in simply searching for their perennial and viable sources for human health applications.
From a biosynthetic point of view, many lignans are formed by the oxidative coupling of E-coniferyl alcohol moieties. But gene identification, gene regulation or biosynthetic enzyme characterization study are still scarce. For example, lignans can share the same precursor as for lignins, the complex polymers that provide rigidity and support to the vascular plants. The regulation of the genes specifically related to lignan biosynthesis or the precursor partition between lignin and lignans have only rarely been investigated. Such data though could yield not only information about the role of these compounds but also for optimizing their bioproduction using metabolic engineering strategies.
Their chemical nature, structural features, physicochemical behavior, and concentrations greatly differ from various plant organs or cultures, food or biological matrices making their extraction, analysis, and purification very challenging. The development of efficient analytical methods dedicated to lignans helps to provide new insight in the natural lignan chemodiversity, evolution throughout the plant kingdom as well as metabolization/detoxification following their absorption/injection in the human body. Moreover, although most in vivo and in vitro data are globally in favor of a chemopreventive effect of lignans, epidemiological studies are sometimes much less conclusive and the mechanism still remains unclear and requires further elucidation. Therefore, the availability of purified lignans at a reasonable cost would allow easier in vivo supplementation experiments and elucidation of mechanisms.
All the known in planta biosynthesis roles as well as health benefits of lignans provide new frontiers for scientists from diverse fields of expertise to further study, elucidate or establish biosynthetic pathways, metabolic engineering, analytical methods and health action mechanisms of this important class of phytochemicals.
This Research Topic is devoted to the latest new insights, in the form of Reviews and Original Research articles, as well as Communication and Perspective papers covering several aspects of plant lignans including:
1) Biosynthesis: gene expression regulation, gene identification, enzyme characterization, chemical ecology, and pathway evolution, etc. Note that descriptive studies involving omics approaches with no functional insights into plant biology are not considered for review.
2) Phytochemistry/analytical methods: occurrence and diversity in plant lineage, extraction, separation and purification analytical methods, structural elucidation, etc. Note that only studies focusing on the plant standpoint will be considered.
3) Metabolic engineering: plants, in vitro cultures, elicitation, biotransformation, biocatalysts, etc.
4) Biological activity of lignans related to human health: in vitro and in vivo laboratory experiments, epidemiological studies, potential mechanisms and effects on human diseases, toxicology, potential side effects, etc. Note that studies carried out with crude extracts will not be considered for review. Only the use of highly purified, chemically characterized compounds is acceptable.
Keywords: Lignans, Metabolic engineering, Analytical methods, Biological activity, Lignans metabolism
... Moreover, both isoflavone compounds in bread samples showed increases with corresponding rises in TWP addition levels. While, in control group, only small amount of glycitin (21.07 μg/g) was detected, which might be possibly descended from wheat bran (Kuhnle et al., 2009). Interestingly, the high amount of isoflavone aglycones detected in TWP-supplemented bread suggested that the transformation of isoflavone glucosidic conjugates to aglycones was occurred during bread making. ...
Tofu whey, as the liquid by-product of tofu manufacturing, contain a high content of valuable nutrients. While, few studies have focused on the potential use of tofu whey as food ingredient. The study was aimed to evaluate effects of tofu whey powder (TWP) supplementation on physicochemical and functional properties of wheat flour pan bread. TWP-added breads showed significant decrease in baking loss but increase in specific volume, antioxidant activities, total phenolic and flavonoid contents of bread samples when increasing the addition levels of TWP. Isoflavone composition analysis showed genistein, daidzein, and glycitein as three major isoflavones, which indicated that the transformation of isoflavone glucosidic conjugates to aglycones was occurred during the bread making. While, at 4% or above addition levels, bread quality was negatively affected by TWP regarding both texture, color profiles and overall acceptance. As a by-product, TWP showed significant potential to improve the bread physicochemical and functional properties.
... The presence of endocrine disruptors (EDs) in food is attracting increasing scientific, public, regulatory, and industrial attention (Commission, 2016;JRC, 2020;LaMotte, 2020). This has triggered the development of various experimental testing tools (US EPA, 1998a;EPA, 1998b;OECD, 2012aOECD, , 2018 and the generation of an extensive amount of diverse analytical and biological data (Bovee et al., 2006;Dinelli et al., 2009;Dykes, 2007;Hostetler et al., 2017;Kuhnle et al., 2009;Lampe, 2003;Le Grand et al., 2015;Leoncini et al., 2012;Lovejoy, 2017;Morito et al., 2001Morito et al., , 2002Neveu et al., 2010;Ososki & Kennelly, 2003;Perez-Jimenez et al., 2010a,b;Promberger et al., 2001;Puranik et al., 2019;Rietjens et al., 2017;Shappell et al., 2019;Smeriglio et al., 2018;Welshons et al., 1990;Zilic, 2016). Among others are those obtained with in vitro bioassays, providing information on endocrine activities such as estrogen receptor activation. ...
... Grains, and in particular whole grain cereals, contain a diversity of phenolic/flavonoid compounds from different classes, many of them exhibiting estrogenic activity. Lignans (e.g., secoisolariciresinol) and flavones (e.g., apigenin, luteolin, tricin, and their derivatives) are considered | 3 FUSSELL Et aL. the predominant wheat phytoestrogens (Dinelli et al., 2009;Kuhnle et al., 2009;Leoncini et al., 2012;Zilic, 2016), although isoflavones (e.g., biochanin A), anthocyanins (e.g., cyanidin and derivatives) and flavanones (quercetin and derivatives) have also been reported to occur (Dykes, 2007;Kuhnle et al., 2009). In cereals, these phytoestrogens exist in three forms: bound to the lignins of the cell wall, soluble but inactivated by glycosylation to various sugar moieties, and the free aglycone. ...
... Grains, and in particular whole grain cereals, contain a diversity of phenolic/flavonoid compounds from different classes, many of them exhibiting estrogenic activity. Lignans (e.g., secoisolariciresinol) and flavones (e.g., apigenin, luteolin, tricin, and their derivatives) are considered | 3 FUSSELL Et aL. the predominant wheat phytoestrogens (Dinelli et al., 2009;Kuhnle et al., 2009;Leoncini et al., 2012;Zilic, 2016), although isoflavones (e.g., biochanin A), anthocyanins (e.g., cyanidin and derivatives) and flavanones (quercetin and derivatives) have also been reported to occur (Dykes, 2007;Kuhnle et al., 2009). In cereals, these phytoestrogens exist in three forms: bound to the lignins of the cell wall, soluble but inactivated by glycosylation to various sugar moieties, and the free aglycone. ...
Background and objectives
The presence of endocrine disruptors in food is creating concern and consequently, efficient methods for their identification are needed. In vitro bioassays have been developed to study endocrine properties of pure chemicals as well as mixtures. Because of their relative ease of execution and low cost, application of such techniques to whole foods is tempting. This raises a number of technical challenges. To address them, a study was commissioned in a contract laboratory offering in vitro estrogenicity testing of food products.
Findings
Four different commercial and regulatory compliant cereal products were sent in blinded triplicates. Some samples were reported to be active by the laboratory. However, the results were not reproducible and very close to the 0% measurable activity. Furthermore, a statistical analysis of the raw data indicated an absence of activity. This was surprising since these products were expected to naturally contain estrogenic compounds such as the phytoestrogens lignans and flavones. However, phytoestrogens in cereals are known to occur mainly in bound, inactive, forms, suggesting that the sample preparation used in the present study was not suitable to release active estrogenic substances. This hypothesis was supported by preliminary data using a high‐resolution mass spectrometry method which did not detect any significant levels of phytoestrogens in the tested cereal extracts.
Conclusions
Using a yeast‐based method, no estrogenic activity was found in breakfast cereals. However, benchmarking the bioassay data against quality criteria raised the question of the qualification of the sample preparation and bioassay used to adequately address estrogenic activity of whole foods.
Significance and novelty
The quality requirements for testing whole food samples were formally addressed. The application of validated and harmonized methods for both sample preparation and bioassay testing is strongly advocated.
