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Content, composition, and stereochemical characterisation of lignans in berries and seeds
Abstract
In seed extracts of five oilseed species, in bran extracts of three cereal species, and in seed and/or whole berry extracts of 10 berry species, the concentrations of a large number of lignans and the enantiomeric composition of selected lignans were determined. In the case of sesame and hemp seeds, the lignan content and composition of the whole seeds was compared to that of the hulled seeds. The results showed that cloudberry seeds are the third most lignan-rich food source after linseeds and whole sesame seeds, and that most of the berry species analysed were more lignan-rich than the cereal brans. The lignans are concentrated in the hull of the oilseeds and in the seeds of the berries. In most samples, secoisolarici-, pino-, medio-, and syringaresinol were present as a mixture of two enantiomers.
... There are two main roles attributed to the lignans: plant defense and antioxidant activity [8]. The lignan content and compositions are significantly dependent on genetic and environmental background, including some other factors such as the maturity stage of the seeds and fruits [8,9]. Environmental factors can affect secondary metabolites biosynthesis by modulation of gene expression through miRNAs and transcription factors. ...
... The enantiomeric composition of some lignans was already determined, for example, in trees, medicinal plants, and some plant foods (linseeds, sesame seeds). It is known that etantiomers of the same type of lignan may show different biological properties and elicit different biological effects [9]. Stereochemical characterization of lignans showed varied etantiomeric composition in the whole berries compared to the seeds [9]. ...
... It is known that etantiomers of the same type of lignan may show different biological properties and elicit different biological effects [9]. Stereochemical characterization of lignans showed varied etantiomeric composition in the whole berries compared to the seeds [9]. ...
Lignans, as secondary metabolites synthesized within a phenylpropanoid pathway, play various roles in plants, including their involvement in growth and plant defense processes. The health and nutritional benefits of lignans are unquestionable, and many studies have been devoted to these attributes. Although the regulatory role of miRNAs in the biosynthesis of secondary metabolites has been widely reported, there is no systematic review available on the miRNA-based regulatory mechanism of lignans biosynthesis. However, the genetic background of lignan biosynthesis in plants is well characterized. We attempted to put together a regulatory mosaic based on current knowledge describing miRNA-mediated regulation of genes, enzymes, or transcription factors involved in this biosynthesis process. At the same time, we would like to underline the fact that further research is necessary to improve our understanding of the miRNAs regulating plant lignan biosynthesis by exploitation of current approaches for functional identification of miRNAs.
... The average content of total lignans in the millet hulls was only 64.4 mg kg − 1 DM. A similar content of total lignans was determined by Smeds et al. (2012) in rye hulls (45.0 mg kg -1 DM) and wheat bran (31.0 mg kg -1 DM). According to Smeds et al. (2007a), the total lignan content in millet bran was only 8.5 mg kg − 1 DM. ...
... However, as pointed out in the present study and many other studies, the content may vary even within the same plant part depending on several factors (genetic, environmental, etc.). e.g., according to Smeds et al. (2012), the PIN content in millet bran was only 2.2 mg kg − 1 DM. So, this phenomenon needs next study. ...
... Compared to Smeds et al. (2012), we quantified a similar content of SYR, MR, and iOMR; about ten times more CLAR and PIN; and lower concentrations of HMR. On the other hand, SEC and CONI in buckwheat hulls were only determined in our study. ...
The distribution of lignans within common millet, common buckwheat, tartary buckwheat, and amaranth plants, as well as any differences of their contents within their different varieties and samples from different growing seasons, were determined by LC-MS analyses. Roots were the plant part highest in the total amount of lignans in common buckwheat, tartary buckwheat, and common millet; which is in contrast to amaranth, where the stems were the richest part. The roots of tartary buckwheat contained five times more total lignans than amaranth stems or common buckwheat roots. The dominant lignan in tartary buckwheat roots was 7-hydroxymatairesinol; in amaranth stems and the roots of common buckwheat it was syringaresinol; and in the roots of common millet it was 7′- oxomatairesinol. The lignin content in the roots, stems, and eventually leaves were significantly influenced by the growing season. In the case of common millet and common buckwheat, differences in lignan levels due to varietal differences were confirmed.
... To our knowledge, this is the first study to identify and quantify the concentration of lignans in the top part (the mixture of stem and leaves) of the hemp plant. Previously, Smeds et al. [17] quantified lignans in the seeds, and found that they were dominated by syringaresinol, medioresinol, secoisolariciresinol, lariciresinol and pinoresinol. Our targeted LC-MS analyses also showed secoisolariciresinol, lariciresinol, syringaresinol and isolariciresinol to be the predominant lignans, although we did not detect any medioresinol and pinoresinol. ...
... Our targeted LC-MS analyses also showed secoisolariciresinol, lariciresinol, syringaresinol and isolariciresinol to be the predominant lignans, although we did not detect any medioresinol and pinoresinol. Higher concentrations of lignans were quantified in the study of Smeds et al. [17] compared to those of our study, indicating that the concentration of lignans is higher in seeds compared to the stalk and leaves; however, the concentrations of lignans have high seasonal variations. In the current study, no lignans were detected in any of the seaweeds analyzed. ...
... Our data support the view that lignans are much more abundant in terrestrial plants and play a limited role in seaweeds, that are phylogenetically distant from plants and do not have structural tissue. In the diet of ruminants, lignans are present in high concentrations in rye and wheat [17]. Isoflavones such as daidzein, genistein and formononetin were detected in a few seaweeds in low concentrations when performing targeted LC-MS analyses. ...
Greenhouse gas emissions are a global problem facing the dairy/beef industry. Novel feed additives consisting of seaweeds and hemp containing bioactive compounds are theorized to reduce enteric methane emissions. In this study we aimed to investigate the metabolic profiles of brown, red and green seaweeds and hemp using gas chromatography and liquid chromatography mass spectrometry. We used targeted and untargeted approaches, quantifying known halomethanes and phenolics, as well as identifying potentially novel bioactive compounds with anti-methanogenic properties. The main findings were: (a) Asparagopsis taxiformis contained halomethanes, with high concentrations of bromoform (4200 µg/g DW), six volatile halocarbons were tentatively identified; (b) no halomethanes were detected in the other studied seaweeds nor in hemp; (c) high concentrations of lignans were measured in hemp; (d) a high numbers of sulfated phenolic acids and unidentified sulfuric acid-containing compounds were detected in all seaweeds; (e) flavonoid glucosides and glucuronides were mainly identified in hemp; and (f) the condensed tannin gallocatechin was tentatively identified in Fucus sp. Using the combined metabolomics approach, an overview and in-depth information on secondary metabolites were provided. Halomethanes of Asparagopsis sp. have already been shown to be anti-methanogenic; however, metabolic profiles of seaweeds such as Dictyota and Sargassum have also been shown to contain compounds that may have anti-methanogenic potential.
... The highest lignan concentrations have been found in flaxseeds and sesame seeds (Milder et al. 2005a;Smeds et al. 2007Smeds et al. , 2012Thompson et al. 2006), and lower concentrations are present in, e.g., Brassica vegetables (Milder et al. 2005a), nuts, and cereals (Mazur and Adlercreutz 1998;Milder et al. 2005a;Penalvo et al. 2008;Smeds et al. 2007). Flaxseed is the richest source of plant lignans due to its high content of secoisolariciresinol diglucoside (SDG) and secoisolariciresinol (SECO) and relatively high matairesinol (MAT). ...
... When comparing results of the lignan content of foods obtained in different studies, it is important to consider that there are several factors affecting results. The lignan content and composition is greatly dependent on natural variations (both genetic and environmental); on the sample pre-treatment applied, including sampling, storage, drying, and extraction methods; and on the analytical method used (Smeds et al. 2012;Durazzo et al. 2018). ...
... Also, lignans occur in plants included in our food, while the concentrations are significantly lower than in coniferous trees. The highest concentrations have been found in flaxseeds and sesame seeds (Milder et al. 2005a;Smeds et al. 2007Smeds et al. , 2012Thompson et al. 2006), and lower concentrations are present in, e.g., Brassica vegetables (Milder et al. 2005a), nuts, and cereals (Mazur and Adlercreutz 1998;Milder et al. 2005a; Penalvo et al. 2008). Plant SDG is known to be part of a macromolecule in which they are connected through the linker-molecule HMGA. ...
Plants over the course of evolution have customized their genomes and produce an enormous variety of specialized phytochemicals termed as secondary metabolites. Secondary metabolites are required by the plants for their interaction with environment and their survival in adverse conditions or stresses. They are derived by unique biosynthetic pathways using primary metabolite and their intermediates. These are mostly synthesized in the cytosol (anthocyanins), chloroplasts (terpenoids), or mitochondria (some amines) but targeted for storage in vacuole for utilization under need. Anthocyanins provide a great economic value for mankind as drugs, food supplement, and dyes. The health benefits of anthocyanins are numerous which have been extrapolated by the scientific community on the basis of their antioxidant capacity. Here potential resources and their role in cancer with biochemical mechanisms have been summarized. The research efforts and accomplishments for the novel anthocyanins and functional food are expected to lead to a sustainable agriculture, health, and environment.
... The highest lignan concentrations have been found in flaxseeds and sesame seeds (Milder et al. 2005a;Smeds et al. 2007Smeds et al. , 2012; Thompson et al. 2006), and lower concentrations are present in, e.g., Brassica vegetables (Milder et al. 2005a), nuts, and cereals (Mazur and Adlercreutz 1998;Milder et al. 2005a;Penalvo et al. 2008;Smeds et al. 2007). Flaxseed is the richest source of plant lignans due to its high content of secoisolariciresinol diglucoside (SDG) and secoisolariciresinol (SECO) and relatively high matairesinol (MAT). ...
... When comparing results of the lignan content of foods obtained in different studies, it is important to consider that there are several factors affecting results. The lignan content and composition is greatly dependent on natural variations (both genetic and environmental); on the sample pre-treatment applied, including sampling, storage, drying, and extraction methods; and on the analytical method used (Smeds et al. 2012;Durazzo et al. 2018). ...
... Also, lignans occur in plants included in our food, while the concentrations are significantly lower than in coniferous trees. The highest concentrations have been found in flaxseeds and sesame seeds (Milder et al. 2005a;Smeds et al. 2007Smeds et al. , 2012; Thompson et al. 2006), and lower concentrations are present in, e.g., Brassica vegetables (Milder et al. 2005a), nuts, and cereals (Mazur and Adlercreutz 1998;Milder et al. 2005a; Penalvo et al. 2008). Plant SDG is known to be part of a macromolecule in which they are connected through the linker-molecule HMGA. ...
Cancer has been recognized as a global health burden in rates of morbidity and mortality. Much effort has been devoted to discover promising cancer therapeutic agents from natural sources, and there has been some progress in introducing new anticancer drugs into the pharmaceutical market. Plant-derived natural products have played a very important role as cancer chemotherapeutic agents, either in their unmodified (naturally occurring) or synthetically modified forms. In this respect, lignans which are presented in a wide range of plants such as flaxseed, sesame, and other seeds, as well as vegetables, fruits, and beverages such as coffee and tea, show diverse spectrum of health-promoting effects, such as anticancer, antioxidant, antiviral, antidiabetic, and protective against cardiovascular diseases. A number of lignans (arctigenin, matairesinol and its glycosides pinoresinol and phillygenin) have come to the fore in research. The production of lignans from plant by the conventional methods is met with several problems. The seasonal production, agricultural practices, handling, and poor storage of plant materials impede offering such demand compounds to pharmaceutical factories. The biotechnological methods, particularly plant cell cultures, are an attractive alternative source to whole plant for the production of such compounds with significant amounts which are not always easily available. The aim of this review is to focus on lignans: biosynthesis in plant, sources, health benefit, and production of flaxseed lignans by plant biotechnological methods.
... Hempseed is a good source of lignan (320 mg/kg DM) (57,58). It is dominated by lignanamides (cannabisin A) while HSC and inflorescences are dominated by flavanols (i.e., catechin; Table 4). ...
... It is dominated by lignanamides (cannabisin A) while HSC and inflorescences are dominated by flavanols (i.e., catechin; Table 4). More so, 99% of lignans are found in hempseed hulls, hence, dehulled hempseeds and the resultant cake have little lignan (57,59). Syringaresinol content of hempseed hull (280 mg/kg DM) is the highest of any dietary source (57). ...
... More so, 99% of lignans are found in hempseed hulls, hence, dehulled hempseeds and the resultant cake have little lignan (57,59). Syringaresinol content of hempseed hull (280 mg/kg DM) is the highest of any dietary source (57). Since HSC is produced from hulled seeds, its lignan content is expected to be low. ...
Plant by-products obtained from agro-industrial processes require valorisation to demonstrate their potential for enhancing animal health, meat production, and shelf life extension. One example is the fast-growing hemp industry, which produces seeds, leaves, seed oil, and cake. Studies on the nutritional value of hempseed cake have shown it can be a valuable source of protein in ruminant diets. However, there is limited documentation on the bioavailability and bioefficacy of hemp phytochemicals for improving ruminant health, production, and extending meat shelf life. The current review provides an overview of existing information on nutrient and phytochemical composition of hemp by-products, their bioavailability, and bioefficacy, and explores current limitations and prospects regarding their valorisation.
... The main sources of dietary lignans are oilseeds (i.e., flax, soy, rapeseed, and sesame), whole-grain cereals (i.e., wheat, oats, rye, and barley), legumes, various vegetables and fruit (particularly berries), as well as beverages, such as coffee, tea, and wine, and, recently, lignans are also reported in dairy products, meat, and fish [64,65,[67][68][69][70][71][72][73][74][75][76][77][78][79][80][81][82][83][84]. The types and amounts vary from one source to another. ...
... Moreover, Penalvo et al. [70] showed for avocado, a profile of decreasing concentration of lignans, syringaresinol > pinoresinol > medioresinol > secoisolariciresinol > lariciresinol > matairesinol and for pineapple, syringaresinol > lariciresinol > matairesinol > secoisolariciresinol > pinoresinol > medioresinol, whereas, the most representative lignan for navel orange was lariciresinol, and secoisolariciresinol for kiwifruit. In berries, as reported by Smeds et al. [78], the most representative lignans among those studied were lariciresinol for cloudberries (5008 µg/100 g dry weight); secoisolariciresinol for blackberries (2902 µg/100 g dry weight), lingoberries (2319 µg/100 g dry weight), blackcurrants (446 µg/100 g dry weight); syringaresinol for cranberries (2578 µg/100 g dry weight), sea buckthorns (1177 µg/100 g dry weight), bilberries (801 µg/100 g dry weight), and red gooseberries (498 µg/100 g dry weight); and pinoresinol for strawberries (1403 µg/100 g dry weight); for raspberries the most representatives were lariciresinol (406 µg/100 g dry weight), syringaresinol (388 µg/100 g dry weight) and pinoresinol (377 µg/100 g dry weight). ...
... In the last decade, researchers are addressing the identification and determination of lignan profiles in main food groups and in food chain products; when a new dataset for nutritional values is used, it is very important to evaluate the quality of the analytical information [55]. New experimental and analytical data on lignan content are now available for updating and expanding food composition databases [64,65,[67][68][69][70][71][72][73][74][75][76][77][78][79][80][81][82][83][84]. In Table 1 the main national databases of lignans are described. ...
The study aims to communicate the current status regarding the development and management of the databases on dietary lignans; within the phytochemicals, the class of the lignan compounds is of increasing interest because of their potential beneficial properties, i.e., anticancerogenic, antioxidant, estrogenic, and antiestrogenic activities. Furthermore, an introductory overview of the main characteristics of the lignans is described here. In addition to the importance of the general databases, the role and function of a food composition database is explained. The occurrence of lignans in food groups is described; the initial construction of the first lignan databases and their inclusion in harmonized databases at national and/or European level is presented. In this context, some examples of utilization of specific databases to evaluate the intake of lignans are reported and described.
... /100 г СВ, а в целых ягодах -14,78 мкг/100 г СВ, что позволило им занять третье место в рейтинге растительного сырья по количеству лигнанов после семян льна и кунжута [18]. ...
... Обобщенный состав фенольных соединений в ягодах морошки и семенах [8,18] представлен в таблице. ...
... 7-HMR is also the most abundant lignan in cereals and the dominant lignan in wheat, triticale, oat and millet bran (from 3 up to 7-9 mg/ 100 g) (10) . It is present at a high concentration in sesame (17 mg/ 100 g) (45) , which is often consumed daily as sesame paste (tahin) in the Middle Eastern countries and it is widespread in several plants (i.e. 1·3 mg/100 g cranberry seeds) (45) . ...
... It is present at a high concentration in sesame (17 mg/ 100 g) (45) , which is often consumed daily as sesame paste (tahin) in the Middle Eastern countries and it is widespread in several plants (i.e. 1·3 mg/100 g cranberry seeds) (45) . Consumption of a , MDI + 7-hydroxymatairesinol (7-HMR); , MDI+ TEP; , MDI + ENL; , MDI + END. ...
7-Hydroxymatairesinol (7-HMR) is a plant lignan abundant in various concentrations in plant foods. The objective of this study was to test HMRLignan™, a purified form of 7-HMR, and the corresponding Picea abies extract (total extract P. abies ; TEP) as dietary supplements on a background of a high-fat diet (HFD)-induced metabolic syndrome in mice and in the 3T3-L1 adipogenesis model. Mice, 3 weeks old, were fed a HFD for 60 d. Subgroups were treated with 3 mg/kg body weight 7-HMR (HMRLignan™) or 10 mg/kg body weight TEP by oral administration. 7-HMR and TEP limited the increase in body weight (−11 and −13 %) and fat mass (−11 and −18 %) in the HFD-fed mice. Epididymal adipocytes were 19 and −12 % smaller and the liver was less steatotic (−62 and −65 %). Serum lipids decreased in TEP-treated mice (−11 % cholesterol, −23 % LDL and −15 % TAG) and sugar metabolism was ameliorated by both lignan preparations, as shown by a more than 70 % decrease in insulin secretion and insulin resistance. The expression of several metabolic genes was modulated by the HFD with an effect that was reversed by lignan. In 3T3-L1 cells, the 7-HMR metabolites enterolactone (ENL) and enterodiol (END) showed a 40 % inhibition of cell differentiation accompanied by the inhibited expression of the adipogenic genes PPARγ , C/EBPα and aP2 . Furthermore, END and ENL caused a 10 % reduction in TAG uptake in HEPA 1–6 hepatoma cells. In conclusion, 7-HMR and TEP reduce metabolic imbalances typical of the metabolic syndrome and obesity in male mice, whereas their metabolites inhibit adipogenesis and lipid uptake in vitro .
... The highest lignans in linseed reported so far is 702,050 µg/100 g of linseed. Specifically in linseed, SECO was found to be 690,757 µg/100 g, which is highest than any other plant food, followed by 335 µg/100 g of LARI, 401 µg/100 g of PINO, 42.3 µg/100 g of MATA and small amounts of other minor lignans (Smeds et al. 2012). Currently, analysis of germplasm collection available in India is being analyzed for the lignan content under DBT supported Government of India project (Kaushik et al. 2022 unpublished data). ...
Lignans have long been known for their abundant therapeutic properties due to their polyphenolic structure. Linseed is the richest plant source of lignans and has been studied widely for their properties. The most prevalent lignan, secoisolariciresinol diglucoside (SDG), is consumed with linseed and converted into mammalian lignans, enterodiol (END) and enterolactone (ENL), by the gut microbiota. SDG can easily be assessed using HPLC and its deglycosylated form viz secoisolariciresinol can be asses using GC–MS techniques. Variety of extraction and analysis methods has been reported for plant lignans. SDG is known to have therapeutic properties including anti-oxidant, anti-cancerous, anti-inflammatory, modulation of gene expression, anti-diabetic, estrogenic and anti-estrogenic. Despite a large number of bioactivities, strong evidences for the underlying mechanisms for most of the properties are still unknown. SDG is most studied for its anti-cancerous properties. But the use of lignans as anti-carcinogenic agent is limited and commercially not reported due to challenges of purification at commercial level, rapid metabolism, untargeted delivery and toxic compounds associated with lignans. Exploration of more prominent and active derivatives of SDG and their targeted drug delivery should be an important research toward the use of bioactive lignans of linseed.
... The highest concentrations were found in flaxseed and sesame, while the lowest were in vegetables of the Brassicaceae family, nuts, and cereals [13]. The lignans secoisolariciresinol and matairesinol were also determined in some berry species and strawberries [14,15]. Most of the interest in lignans is due to their potential application in the pharmaceutical and nutraceutical fields. ...
Lignans, a group of polyphenols, have been identified in eight cold pressed oils from fruits, nuts, and seeds, retrieved from the Brazilian market. The oils under investigation were avocado, Brazilian nut, canola, coconut, grapeseed, macadamia, palm, and pequi. Olive oil was selected as a reference oil, since numerous data on its lignan content are available in literature. The qualitative and quantitative profiles were obtained, after extraction, by means of UFLC-ESI-MS/MS analyses. The total lignan content showed a high variability, ranging from 0.69 mg·Kg−1 (pequi) to 7.12 mg·Kg−1 (grapeseed), with the highest content registered for olive oil. Seven lignans were quantified, matairesinol and pinoresinol being the most abundant. The LC-MS/MS method was validated, showing linearity in the range of 12.5–212.5 mg·Kg−1, LOD in the range of 0.18–11.37 mg·Kg−1, and LOQ in the range of 0.53–34.45 mg·Kg−1. Additionally, part of the study was focused on the evaluation of the flavor profile, this being a key element in consumers’ evaluations, by means of HS-SPME-GC. In total, 150 volatile compounds were determined in the eight oils, with identified fractions ranging from 91.85% (avocado) to 96.31% (canola), with an average value of 94.1%. Groups of components contributed characteristically to the flavour of each oil.
... The lignanamides including cannabisinlike compounds (A-, B-, C-, D-, E-, F-, and G types; Flores-Sanchez and Verpoorte 2008) and lignans also were found in the Cannabis sativa. The lignan profile in hemp seeds was shown to be mainly determined by the presence of syringaresinol and medioresinol ( Fig. 1.4) and also by secoisolariciresinol, lariciresinol, and pinoresinol (Smeds et al. 2012). Additionally, nineteen stilbenes have been isolated in Cannabis with a prototypical structural backbone such as spirans, phenanthrenes, and bibenzyls (Flores-Sanchez and Verpoorte 2008). ...
Cannabis sativa L. is a psychoactive plant that contains more than 500 chemical components. Even though the consumption (in the form of marijuana, hashish, or hashish oil) for recreational purposes, is the most popular way of using the plant, the knowledge of its components has also led to classify Cannabis sativa L. is a plant with medicinal or therapeutical use. Several comprehensive reviews have already been published focused on the chemical composition of Cannabis sativa. In this chapter, we will summarize relevant information about those components, which may help to understand its biological actions that will be described in the following chapters.
... In view of various reports of cytotoxic and antibacterial effects of Solanum alkaloids (Kaunda and Zhang, 2019a), we evaluated compounds 1-6 for the biological activities mentioned above. Moreover, due to the impressive antitumor effects demonstrated by lignans (Cutillo et al., 2003), and considering that previous reports (Cutillo et al., 2003;Khan et al., 2020;Niemi et al., 2012;Smeds et al., 2007Smeds et al., , 2012Della-Greca et al., 2006;Honbu et al., 2002) on compound 9, a lignan, did not illuminate on its biological activities, we undertook to evaluate its cytotoxic efficacy, alongside the formerly undescribed isolates. ...
Three previously undescribed pyridyl-steroidal glycoalkaloids, solanindiosides A‒C, one rare 23S,26R-hydroxylated spirostanoid saponin, and two steroidal alkaloid aglycones, solanindins A and B, derived from the acid hydrolysis of solanindiosides A‒C, were isolated from the fruits of Solanum violaceum, together with five known analogues, including two rare steroidal glycosides, two lignans and a diterpene. Structurally, they comprise a 16β-methoxy-23-deoxy-22,26-epimino-cholest-type skeleton moiety, and a 16β-methoxy-3,23-dideoxy-22,26-epimino-cholest-3,5-dien derivative. The hitherto undescribed structures were established on the basis of extensive spectroscopic analyses. Configurations of sugar moieties were resolved by chemical derivations. Solanindiosides A‒C, (22R,23S,25R,26R)-spirost-5-ene-3β,23,26-triol3-O-β-d-xylopyranosyl-(1→3)-β-d-glucopyranoside, solanindins A and B, and (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol were evaluated for their cytotoxic and antibacterial activities. (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol showed the most potent cytotoxic activity against MCF-7 cells (IC50 = 4.386 ± 0.098 μM), while solanindin B displayed some inhibitory effects against Staphylococcus aureus Rosenbach with MIC50 value of 37.32 ± 0.793 μM. In addition, (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol induced dose dependent apoptosis effect in MCF-7 cells.
... Arctigenin has been extensively studied for its anti-inflammatory effects in both in vitro and in vivo models (Gao, Yang, & Zuo, 2018). Overall, some previous reports (Smeds et al., 2012) showed that hemp seeds are characterized by several lignans, including syringaresinol, medioresinol, pinoresinol, and secoisolariciresinol. In our experimental conditions, the different Futura 75 hempseed oils showed only a distribution of secoisolariciresinol and its derivatives, namely anhydro-secoisolariciresinol and 7-hydroxysecoisolariciresinol. ...
In this work, considering the rising interest towards the exploitation of hemp seed oil in human nutrition, 45 hemp seeds from mono-variety fields were analyzed for their yield, oil content, in vitro antioxidant activity, followed by a comprehensive assessment of phenolic and sterolic composition. The results demonstrated that seed dimension is inversely correlated to total oil content, thus being a potential reference for quality assessment of seeds and for further improvement of hemp varieties. The UHPLC-QTOF metabolomic analysis revealed a large abundance of phytosterols, lower-molecular-weight phenolic acids, and lignanamides. Differences across varieties could be described, with Diana Hemp seed oil having the highest cumulative abundance of phytochemicals, recording 6.04 mg/g. Overall, the in vitro antioxidant activity results indicated that hemp seed oil antioxidants have a low potential for preventing oil rancidity, with phenolic acids being the most active radical scavengers. Besides, in the group of Futura 75 samples cultivated across Italy, the type of harvesting affected the acidity value significantly as a consequence of mechanical harvest and post-harvest handling. Finally, multivariate statistics following untargeted metabolomic analysis showed that variety, geographical origin, and harvest-type were able to affect the phytochemical profiles with different incidences, with some phytochemocals proposed for the first time as potential discriminant markers.
... Significant levels of lignans such as syringaresinol, pinoresinol, lariciresinol, and secoisolariciresinol were determined in the hydrophilic extract obtained from Cannabis seeds. However, it was found that the total amount of lignans in Cannabis seeds is about 20 times lower than in flax seeds and is only 32 mg per 100 g of dry weight [89]. Moreover, the content in the seed shell is only 1% of the lignans content in the whole seed. ...
Cannabis sativa L. turned out to be a valuable source of chemical compounds of various structures, showing pharmacological activity. The most important groups of compounds include phytocannabinoids and terpenes. The pharmacological activity of Cannabis (in epilepsy, sclerosis multiplex (SM), vomiting and nausea, pain, appetite loss, inflammatory bowel diseases (IBDs), Parkinson’s disease, Tourette’s syndrome, schizophrenia, glaucoma, and coronavirus disease 2019 (COVID-19)), which has been proven so far, results from the affinity of these compounds predominantly for the receptors of the endocannabinoid system (the cannabinoid receptor type 1 (CB1), type two (CB2), and the G protein-coupled receptor 55 (GPR55)) but, also, for peroxisome proliferator-activated receptor (PPAR), glycine receptors, serotonin receptors (5-HT), transient receptor potential channels (TRP), and GPR, opioid receptors. The synergism of action of phytochemicals present in Cannabis sp. raw material is also expressed in their increased bioavailability and penetration through the blood–brain barrier. This review provides an overview of phytochemistry and pharmacology of compounds present in Cannabis extracts in the context of the current knowledge about their synergistic actions and the implications of clinical use in the treatment of selected diseases.
... Among cereals, the highest lignan contents are found in rye and wheat (Smeds et al., 2007). Cereals, in particular rye, are rich in Syr but also Seco and Mat are found in high concentrations along with hMat (Penalvo et al., 2005a;Smeds et al., 2012). (Smeds et al., 2007) Corn bran 125 33 69 21 2 (Smeds et al., 2007) (Milder et al., 2005 Broccoli 6 6 82 94 Cabbage 3 44 32 79 Carrot 93 19 60 171 (Milder et al., 2005) Garlic 42 482 54 5 583 Spinach 8 1 59 0 67 Sweet peppers (green) 7 1 164 0 172 (Milder et al., 2005) Tomatoes ( Thompson et al., 2006) Milk, soya 1 30 7 0 38 (Milder et al., 2005) Tea, black 5-6 27-41 29-31 1-2 64-77 (Milder et al., 2005) T e a , g r e e n 1 3 6 1 9 2 3 9 ( M i l d e r et al., 2005) ...
Plant lignans constitute a group of diphenolic compounds, including matairesinol, pinoresinol, medioresinol, lariciresinol, sesamin, syringaresinol, secoisolariciresinol, secoisolariciresinol diglucoside, and hydroxymatairesinol, widely distributed in foods and beverages, of which the most important are whole grains, seeds, nuts, vegetables, berries, and tea and coffee. In order to be absorbed, ingested lignans have to be hydrolyzed by endogenous or bacterial enzymes in the gastrointestinal tract to lignan aglycones which can be absorbed directly or converted by colonic bacteria to the enterolignans enterolactone and enterodiol. The generally accepted view is that the enterolactone and enterodiol are taken up in circulation where they provide protection against several diseases, including cancer (breast, prostate, and colorectal), cardiovascular diseases, and type 2 diabetes. Studies with flaxseeds, sesamin, and cereals, however, have shown that a certain fraction of the plant lignans is absorbed as such but with a half‐life much lower than that of the enterolignans. The biological role of absorbed plant lignans is unknown, but cell studies have indicated that plant lignans could have antiinflammatory and other cellular effects. It is concluded that in order to obtain a full picture of the health properties of lignans, future studies should include the plant lignans as well.
... Comparable volumes of Lari in both flaxseed and oilseed mix were found: 44.2 mg/100 g and 44.9 mg/100 g, respectively. Seco and Mat are the main substrate for enterolignans, with Seco being converted to EL through ED, and Mat being directly converted to EL. Differences in lignan concentration were discussed previously [5,36] and are thought to be related to variance in the crop, climate, storage conditions and other factors. Thus, it was expected to obtain concentrations that would diverge from previously reported data. ...
Background
Dietary lignans belong to the group of phytoestrogens together with coumestans, stilbenes and isoflavones, and themselves do not exhibit oestrogen-like properties. Nonetheless, the gut microbiota converts them into enterolignans, which show chemical similarity to the human oestrogen molecule. One of the richest dietary sources of lignans are oilseeds, including flaxseed. The aim of this study was to determine the concentration of the main dietary lignans in an oilseed mix, and evaluate the gut microbiota-dependent production of enterolignans for oestrogen substitution in young and premenopausal women. The oilseed mix was fermented in a pH-controlled batch culture system inoculated with women’s faecal samples. The lignan content and enterolignan production were measured by ultra‐high-performance liquid chromatography – tandem mass spectrometry (UHPLC-MS/MS), and the gut-derived microbial communities were profiled by 16S rRNA gene-based next-generation sequencing.
Results
In vitro batch culture fermentation of faecal samples inoculated with oilseed mix for 24 h resulted in a substantial increase in enterolactone production in younger women and an increase in enterodiol in the premenopausal group. As for the gut microbiota, different baseline profiles were observed as well as different temporal dynamics, mainly related to Clostridiaceae, and Klebsiella and Collinsella spp.
Conclusions
Despite the small sample size, our results revealed that lignan-rich oilseeds have a strong influence on the faecal microbiota of both younger and premenopausal females, leading to a different enterolignan profile being produced. More studies are needed to evaluate the long-term effects of lignan-rich diets on the gut microbiota and find out how enterolactone-producing bacterial species could be increased. Diets rich in lignans could potentially serve as a safe supplement of oestrogen analogues to satisfy cellular needs for endogenous oestrogen and deliver numerous health benefits, provided that the premenopausal woman microbiota is capable of converting dietary precursors to enterolignans.
... The high antioxidant capacity showed by 97:3 (3), 96:4, and 95:5 fractions of HS was due to their homogeneous chemical composition practically reduced to one or two group components. As it is reported in Table 3, the main components of 97:3 (3) were todolactol and hydroxymatairesinol (HMR), which are considered powerful antioxidants [40,41]. Moreover, the 96:4 fraction was mainly composed of phenolic compounds, while the composition of 95:5 was based on todolactol and flavonoids such as pinobasquin and catechin. ...
Hazelnut (HS) and walnut (WS) shells, an abundant by-product of the processing industries of these edible nuts, are traditionally considered as a low-value waste. However, they are a source of valuable compounds with an interesting chemical profile for the chemical and pharmaceutical sectors. In this study, the lipophilic and hydrophilic extracts present in HS and WS were quantified and identified, then the polar fractions were chromatographically separated, and their antioxidant capacity was studied. The experimental work includes the isolation of crude lipophilic and hydrophilic extracts by an accelerated extraction process, chromatographic analysis (gas chromatography-flame ionization (GC-FID), GC-mass spectroscopy (GC-MS), high-performance size-exclusion chromatography (HPSEC), thin-layer chromatography (TLC)), and quantification of the components. In addition, a thorough compositional characterization of the subgroups obtained by flash chromatography and their antioxidant capacity was carried out. The gravimetric concentrations showed different lipophilic/hydrophilic ratios (0.70 for HS and 0.23 for WS), indicating a higher proportion of polar compounds in WS than in HS. Moreover, the lipophilic extracts were principally composed of short-chain fatty acids (stearic, palmitic, and oleic acid), triglycerides, and sterols. The polar fractions were screened by thin-layer chromatography and then separated by flash chromatography, obtaining fractions free of fatty acids and sugar derivatives (97:3 in HS and 95:5 in WS), and mixtures richer in phenolic compounds and flavonoids such as guaiacyl derivatives, quercetin, pinobanksin, and catechin. The most polar fractions presented a higher antioxidant capacity than that of the crude extracts.
... Several studies (Willför et al., 2003b,c;Lindberg et al., 2004;Nuopponen et al., 2004;Hovelstad et al., 2006;Pietarinen et al., 2006b;Karppanen et al., 2007;Núñez, 2009;Bonzanini et al., 2009;Smeds et al., 2012b;Conde et al., 2013;Sekine et al., 2013;Fang et al., 2013;Vek et al., 2014;Kebbi-Benkeder et al., 2015;Johansson et al., 2015;Tsvetkov et al., 2019aTsvetkov et al., , 2019bSabo and Knezevic, 2019;Saloua et al., 2009;Radoukova et al., 2018;Belt et al., 2017;Benković,et al., 2017) have shown that knotwoods and other parts of the plants contain diverse chemical constituents with various biological activities. Polyphenols are concentrated in knotwood probably due to their strong antioxidant (Willför et al., 2003b) and antimicrobial effects (Lindberg et al., 2004). ...
Knotwood, the branch base inside the tree stem, which is undesirable in the processing of wood, constitutes an abundantly available biomass residue that is of no commercial value and remains underutilized. However, knotwood, as a rich source of various bioactive molecules, has significant importance for utilization as a renewable feedstock for the production of high-value chemicals. Knotwood in temperate climate zones has been a subject of extensive chemical studies, and a number of secondary metabolites have been characterized, including lignans, norlignans, flavonoids, stilbenoids, phenolic acids, tannins, diarylheptanoids, terpenoids, sterols, qui-nones, aromatic compounds, and fatty acids. Chemistry of different parts (bark, heartwood, sapwood, stemwood, wood) other than the knotwood of these tree species has also been published. Several phenolics and dia-rylheptanoids have been reported. These chemical constituents and their associated bioactivities have been reviewed. The structural proximity of the components of knotwood and other parts of these trees was observed. However, the concentration of the extractives was higher in knotwood than in other parts of the trees. The chemistry of knotwood of subtropical trees except Tectona grandis L.f. has not been investigated. Published information on the chemistry and bioactivities of Azadirachta indica Adr. Juss., Mangifera indica L. and Tectona grandis L.f. as representatives of subtropical trees of great economic significance was also compiled and reviewed. The constituents characterized in different parts of these trees were phenolics, terpenoids, limonoids, steroids, quinones, benzophenones and fatty acids. Based on the structural proximity of the components of knotwood and other parts of temperate trees, it is postulated that the chemical constituents characterized in different parts of tree species from subtropical regions may also occur in their hitherto uninvestigated knotwood. Our observations stimulate further chemical investigations of the knotwood of these woody perennials.
... Comparable volumes of Lari were found in both flaxseed and oilseed mix: 44.2 mg/100 g and 44.9 mg/100 g, respectively. Seco and Mat are the main substrate for enterolignans, with Seco being converted to EL via ED, and Mat being directly converted to EL. Differences in lignan concentration have been previously discussed [5,48] and are thought to be related to variance in crop, climate, storage conditions and other factors. Therefore, it was expected to obtain concentrations that would diverge from previously reported data. ...
Background:
Dietary lignans belong to the group of phytoestrogens together with coumestans, stilbenes and isoflavones, and themselves do not exhibit oestrogen-like properties. Nonetheless, the gut microbiota converts them into enterolignans, which show chemical similarity to the human oestrogen molecule. One of the richest dietary sources of lignans are oilseeds, including flaxseed. The aim of this pilot study was to determine the concentration of the main dietary lignans in an oilseed mix, and explore the gut microbiota-dependent production of enterolignans for oestrogen substitution in young and premenopausal women. The oilseed mix was fermented in a pH-controlled batch culture system inoculated with women's faecal samples. The lignan content and enterolignan production were measured by ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS), and the faecal-derived microbial communities were profiled by 16S rRNA gene-based next-generation sequencing.
Results:
In vitro batch culture fermentation of faecal samples inoculated with oilseed mix for 24 h resulted in a substantial increase in enterolactone production in younger women and an increase in enterodiol in the premenopausal group. As for the gut microbiota, different baseline profiles were observed as well as different temporal dynamics, mainly related to Clostridiaceae, and Klebsiella and Collinsella spp.
Conclusions:
Despite the small sample size, our pilot study revealed that lignan-rich oilseeds could strongly influence the faecal microbiota of both younger and premenopausal females, leading to a different enterolignan profile being produced. Further studies in larger cohorts are needed to evaluate the long-term effects of lignan-rich diets on the gut microbiota and find out how enterolactone-producing bacterial species could be increased. Diets rich in lignans could potentially serve as a safe supplement of oestrogen analogues to meet the cellular needs of endogenous oestrogen and deliver numerous health benefits, provided that the premenopausal woman microbiota is capable of converting dietary precursors into enterolignans.
... The highest lignan concentration was reported in cloudberry, both in the seed (43,876 µg/100 g DW) and the whole fruit (14,775 µg/100 g DW), followed by blackberry (seed: 23,310 µg/100 g DW; whole fruit: 9,995 µg/100 g DW) and cranberry (seed: 16,713 µg/100 g DW; whole fruit: 6,858 µg/100 g DW). The predominant lignans in berries are lariciresinol-sesquilignan (LAR-SQ), secoisolariciresinol (SECO), and matairesinol (MR) (Smeds, Eklund, & Willför, 2012). In blackberries, SECO (3.72 mg/100 DW) and MR (<0.01 mg/100 g DW) lignans have been identified. ...
The bioactive compounds present in the genus Rubus have garnered special attention due to the health benefits of their consumption, mainly, phenolic compounds such as flavonoids (anthocyanins, flavanols and phenolic acids) and ellagitannins. However, their biological activity is related with their absorption and metabolism. The purpose of this chapter is to summarize the available scientific information of the bioactive compounds in Rubus blackberries and raspberries and their bioavalibility, as well as their effect on intestinal microbiota and tissue distribution. Similarly, we review the role of the phenolic compounds in Rubus berries in the prevention and treatment of neurodegenerative disorders. Experimental studies suggest that anthocyanins of these fruits improve cognition and improve human health.
... 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). ...
The current study provides a comprehensive overview and analysis of the lignan literature. Data for the current study were extracted from the electronic Web of Science Core Collection database via the search string TOPIC = (“lignan*”) and processed by the VOSviewer software. The search yielded 10,742 publications. The ratio of original articles to reviews was 14.6:1. Over 80% of the analyzed papers have been published since the year 2000 and nearly 50% since the year 2010. Many of the publications were focused on pharmacology, chemistry, and plant sciences. The United States and Asian countries, such as China, Japan, South Korea, and India, were the most productive producers of lignan publications. Among the 5 most productive institutions was the University of Helsinki in Finland, the country that ranked 9th. Nineteen journals collectively published 3,607 lignan publications and were considered as core journals. Their impact factor did not correlate with the proportion of uncited papers. Highly cited publications usually mentioned phytoestrogen, isoflavone, daidzein, enterodiol, enterolactone, equol, genistein, and isoflavonoid. Cancer (e.g., breast cancer), cardiovascular disease, and antioxidation were the major themes. Clinical trials were estimated to contribute to 0.2–1.1% of the analyzed body of literature, so more of them should be conducted in the future to substantiate the beneficial effects and optimal dose of lignan intake in humans. Moreover, researchers can refer to these findings for future research directions and collaborations.
... Naturally occurring lignans have been found to exist exclusively as one enantiomer, or as enantiomeric mixtures with various enantiomeric compositions. The enantiomeric composition of the plant lignans in trees and medicinal herbs and shrubs is commonly known, and usually only one of the enantiomers occurs in a certain species [105][106][107] . ...
Since ancient times, medicinal plants and pharmacologically active products obtained from different natural sources play an important role in human health. Plants belonging to the genus Artemisia possess a great biological potential and it is a well-studied genus in the fields such as systematics (including molecular phylogenetics) and genome organization. Many species of the genus (e.g., A. absinthium, A. annua, A. vulgaris, A. abrotanum, A. arborescens) are widely exploited, because of their high economic value as medicines, food and ornamentals. Withal, in such a large genus, some hiatus must inevitably exist, concerning attainments and potentials that individual species possess. Most of the studies are focused on bioactivity and pharmacology of sesquiterpene lactones. Lignans are unjustly neglected, even though they as well exhibit a wide range of bioactivities. Motivated by that fact, we tried to consolidate findings on bioactive lignans accumulated through the years, with the logical perspectives on further work on isolation and identification of new bioactive lignans and the exploitation of lignans as substances of potential pharmacological interest. [Project of the Serbian
Ministry of Education, Science and Technological Development, Grant no.
172047]
... Several studies (Willför et al., 2003b,c;Lindberg et al., 2004;Nuopponen et al., 2004;Hovelstad et al., 2006;Pietarinen et al., 2006b;Karppanen et al., 2007;Núñez, 2009;Bonzanini et al., 2009;Smeds et al., 2012b;Conde et al., 2013;Sekine et al., 2013;Fang et al., 2013;Vek et al., 2014;Kebbi-Benkeder et al., 2015;Johansson et al., 2015;Tsvetkov et al., 2019aTsvetkov et al., , 2019bSabo and Knezevic, 2019;Saloua et al., 2009;Radoukova et al., 2018;Belt et al., 2017;Benković,et al., 2017) have shown that knotwoods and other parts of the plants contain diverse chemical constituents with various biological activities. Polyphenols are concentrated in knotwood probably due to their strong antioxidant (Willför et al., 2003b) and antimicrobial effects (Lindberg et al., 2004). ...
... As a large group of phenolics, lignans were also detected form the seeds of cloudberry, blackberry, cranberry, bilberry, raspberry, sea buckthorn, and blackcurrant. The total content ranged from 0.02 (blackcurrant) to 0.4 mg/g of dry seeds (cloudberry) [173]. ...
Circular economy is an umbrella concept that applies different mechanisms aiming to minimize waste generation, thus decoupling economic growth from natural resources. According to United Nations [1], each year, an estimated 1/3 of all food produced – equivalent to 1.3 billion tons worth around US$1 trillion, increasing to $2.6 trillion when social and economic costs are considered. In the fruit and vegetable sector, 45% of the total produced amount are lost in the production (post-harvest, processing, and distribution) and consumptions chains. Therefore, it is necessary to find new technological and environmentally friendly solutions to utilize fruit wastes as new raw materials to develop and scale up the production of high-value added products. Taking into consideration that the production and consumption of fruits has increased in the last years and following the need to find sustainable use of different fruit side streams, this work aimed to describe the chemical composition and bioactivity of different fruit seeds consumed worldwide. A comprehensive focus is given on the extraction techniques of water-soluble and lipophilic compounds and in vitro/in vivo functionalities and the link between chemical composition and observed activity is holistically explained.
... While medioresinol was clearly characterised among the early eluting HPLC peaks, several other lignans described in hempseed cakes (Smeds et al. 2012) did not occur at detectable amounts. Some of the low abundant peaks eluting in the low retention time range of the HPLC separation (18-30 min) were simple phenolic acids, such as hydroxybenzoic and hydroxycinnamic derivatives, already characterised in hempseed cakes (Pojic et al. 2014). ...
Total phenolic content and antioxidant activity of polar extracts of edible resources from Fedora hemp cultivar (Cannabis sativa L.), namely seed, flour and oil, were evaluated. The main components in the polar extracts were identified using HPLC-DAD and HPLC-ESI-MS/MS. As expected, the molecular profile of components from seeds and flour was strictly similar, dominated by N-trans-caffeoyltyramine. The profile of oil polar extracts contained hydroxycinnamic acid derivatives and cannabinoids at lower extent. While the extracts from hemp seed and flour did not interfere with growth of Caco-2 and HT-29 cell, the one from oil (150 µg/mL) significantly reduced cell viability after 24 h of treatment. This effect was associated with the activation of apoptotic cell death and was independent from the antioxidant capacity of the oil polar extract. Notably, HT-29 cells differentiated with sodium butyrate were not sensitive to the cytotoxic effect of the oil extract.
... Lignans are vascular plant secondary metabolites, with widespread occurrence in the plant kingdom, and which are ascribed to a wide range of physiological functions, positively affecting human health (Durazzo, 2018). In fruits, lignans are reported in apple, grapes, apricot, blackberry, cranberry, cloudberry, cherry, blueberry, peach, and strawberry (Kuhnle et al., 2009;Milder, Arts, Van de Putte, Venema, & Hollman, 2005;Peñalvo, Haajanen, Botting, & Adlercreutz, 2005;Smeds, Eklund, & Willför, 2012;Thompson et al., 2006). As instance, Bonzanini, Bruni, Palla, Serlataite, and Caligiania (2009) Tannins, phenolic compounds of high molecular weight (in the range 500-20,000 Da) synthesized via the shikimic acid pathway (Kabera et al., 2014;Smeriglio, Barreca, Bellocco, & Trombetta, 2017), are classified into two major groups: hydrolyzable tannins and non-hydrolyzable tannins, also called condensed tannins or proanthocyanidins. ...
This paper proposes a perspective literature review of the antioxidant properties in fruit‐based juices. The total antioxidant properties due to compounds such as carotenoids, polyphenolic compounds, flavonoids, and tannins as well as the assessment of interactions between natural active compounds and other food matrix components can be seen as the first step in the study of potential health benefits of fruit‐based juices. A brief summary is given on the significance of antioxidant properties of fruit juices, the conventional methods for antioxidant activity evaluation, and on the newly emerged sample analysis and data interpretation strategies, that is, chemometric analysis based on spectroscopic data. The effect of fruit processing techniques and the addition of ingredients on the antioxidant properties of fruit‐based juices are also discussed.
... (b) Stilbenes are found in red wines, red grape juice and peanuts [25,26] (resveratrol is the most well-known) (c) Lignans: Examples are secoisolariciresinol found in flaxseed [24] and sesamin found in sesame seed [27]. ...
... Hemp seeds (HS) are a great source of phytochemicals, containing around 30% fats and 25% proteins as well as fiber, cannabinoids, vitamins and minerals [29][30][31]. They also contain polyphenols (caffeic acid, quercetin and luteolin) [31], lignans [32], terpenoids [27], as well as protein hydrolysates, which have been shown to reduce oxidative stress factors in hypertensive rats [33]. They are known especially for containing polyunsaturated fatty acids (PUFAs), mainly ω-6 and ω-3, which are active molecules studied for their anti-inflammatory action, immune and oxidative stress modulation [29,[34][35][36]. ...
This study shows the antioxidant effect of a dietary hemp seed diet rich in ω-6 polyunsaturated fatty acid (PUFA) on oxidative status in sows during late gestation and lactation and their offspring. Ten pregnant sows were divided into two groups and fed either a control diet (CD) or a hemp diet (HD) containing 2% hemp seed meal for a period of 10 days before farrowing and 5% throughout the lactation period (21 d). After farrowing, 16 of their resulting piglets were divided into two groups: control group CD (eight piglets derived from control sows) and HD group (eight piglets derived from HD sows), respectively. Blood collected from sows and piglets at day 1, 7 and 21 was used for the measurement of antioxidant enzymes (catalase (CAT), superoxide dismutase (SOD), glutathione (GPx)), nitric oxide production (NO), lipid peroxidation (thiobarbituric acid reactive substances—TBARS), reactive oxygen species (ROS) generation and total antioxidant capacity (TAC) in plasma. The results showed a significant improvement in the oxidative status of sows fed HD throughout lactation compared with CD. Similarly, in piglets, HD positively influenced the activities of antioxidant enzymes, TAC and NO levels and significantly decreased lipid peroxidation in plasma until weaning, in comparison with the CD group. This study suggests the potential of hemp seed diet to improve the overall antioxidant status of the lactating sows and their progeny.
... It is impossible to precisely affirm which parts of sea-buckthorn contain more AO as the quantitative composition can be influenced by the botanical breed of sea-buckthorn, the area of its cultivation, or the method of research being used to study it (Jalakas et al., 2003;Bal et al., 2011). The peel and the pulp contain a lot of ascorbic acid, carotenoids, and phytosterols, while the seeds are rich in cochromanol and lignans (Li et al., 2007;Christaki, 2012;Smeds et al., 2012). Phenolic compounds can dominate in the pulp and the peel of berries or seeds (Saikia & Handique, 2013), while flavonoids (with a predominance of rutin and quercetin) are concentrated mostly in the leaves of seabuckthorn (Fatima et al., 2015). ...
Triticale is hybrid crop developed by crossing wheat (Triticum) and rye (Secale) and in last years it become more popular for food applications, including flake production. Different approaches are developed to improve flakes technology by applying different cooking, rolling, toasting parameters resulting in high quality products. All these technologies influence also nutrition quality of product due to the different stability of these compounds during mechanical and thermal treatment. The aim of current experiment was to investigate the influence of technological parameters on chemical composition of triticale flakes. In current experiment triticale grains and triticale flakes obtained by different technologies was tested. For evaluation of the influence of technological parameters, different flaking and rolling parameters were tested. For all samples were determined composition of basic nutrients (fats, proteins, fibres, sugars, ash), minerals (Ca, Mg, K, Zn, P), vitamins, total phenolics and antioxidant activity. Triticale has high nutritional quality, containing significant amounts of protein, fibres, vitamins and minerals. Technological processes significantly influence cereals composition, but it depends on parameters tested. Control sample showed lower results and hierarchical cluster analyses showed that samples 1/3/1, 2/1/2/1, 2/1/3/1, 2/1/4/1 are similar in composition of bioactive compounds. Results showed that for selection of the best method for flaking physical and/or sensory properties should be taken in account.
... However, berries are consumed without crushing the seeds. Because the seeds pass through the intestine as such, the bioavailability of berry lignans is low (Smeds et al., 2012). ...
Introduction – It is well known that berries have beneficial effects on health, owing to their content of phenolic molecules, such as anthocyanin, quercetin and phenolic acid, as well as their content of vitamins, minerals and fiber. There is a gradually increasing body of evidence suggesting that these bioactive molecules have antioxidant, anti-inflammatory, antimicrobial, anticarcinogenic, antimutagenic and neuroprotective effects. Owing to their antioxidant effects, berry consumption brings positive effects against cardiovascular diseases, obesity, ageing and neurodegenerative diseases. Specific objectives – This paper was aimed to highlight natural compounds and health effects of the berries; some mechanisms explored by experimental studies, and to outline human intervention trial. Thus, this review could be useful to develop consumption recommendations and following research in health outcomes.
... The berry press residue is principally composed of seeds-about 25% of dry mass of pomaces [12]. Seeds are a valuable raw material, because contain a wide variety of compounds such as etheric oils and fatty acids [11,13,14], nutrients necessary in animal feeding [15,16], cutin [17,18], lignans [19], polyphenols [20], lipids and lipoproteins [21] and have antioxidative properties [22]. These compounds can be extracted and used as food supplements [23] and in cosmetic industry [24,25]. ...
Biological waste constitutes a resource that could be valorised into micronutrient fertilizers. Micronutrient fertilizers (berries seeds residues enriched with micronutrients—blackcurrant Ribes nigrum L., raspberry Rubus idaeus L., strawberry Fragaria × ananasa) produced via biosorption were developed. Micronutrient content was investigated by Scanning Electron Microscope with Energy Dispersive X-ray analysis (SEM-EDX) as an alternative method to Inductively Coupled Plasma Optical Emission Spectrometry (ICP-OES) which is known as costly, time-consuming and sample-destructive method. X-ray mapping of SEM images and ICP-OES analysis showed the differences in the concentration of micronutrients on the materials surface (natural and enriched biomass—from 3 to 24 times). The highest content of micronutrients (ICP-OES) was achieved for enriched blackcurrant [Cu(II)-12.8 mg g⁻¹, Zn(II)-10.8 mg g⁻¹] and strawberry seeds [Mn(II)-5.13 mg g⁻¹]. The highest atomic concentration of micronutrients was found on the surface (SEM-EDX) of enriched strawberry [24.5% for Cu(II), 8.43% for Mn(II) and 11.1% for Zn(II)]. It was shown that increasing content of micronutrient ions in biological material after biosorption was connected with decreased level of the following cations: Ca(II), Mg(II) and K(I) (ion exchange). The uniform distribution of micronutrient ions was observed on SEM micrographs. The structure of the surface, surface topography (steps, bends and broken edges) were also investigated. The content of micronutrients in biomass determined with ICP-OES and SEM-EDX revealed high correlations between these methods for manganese, zinc and copper ions (0.848, 0.739, 0.735, respectively). Described experiments showed that SEM-EDX was an efficient tool and an alternative for ICP-OES.
... One of the active components that may play a role in the healthbeneficial properties of whole grains and their consumption is the lignans. Lignans are diphenolic compounds found in high concentrations in such common foods as seeds, grains, berries, and vegetables (4)(5)(6). As concerns cereal grains, the concentration of lignans is higher in rye than in wheat, oats, and barley (5), and the lignan content in grain is found mainly in the outer bran layer (pericarp or testa and aleurone) (7,8). ...
Background: Whole-grain intake is associated with a lower risk of chronic Western-style diseases, possibly brought about by the high concentration of phytochemicals, among them plant lignans (PLs), in the grains.
Objective: We studied whether treatment of rye bran with cell wall–degrading enzymes changed the solubility and kinetics of PLs in multicatheterized pigs.
Methods: Ten female Duroc × Danish Landrace × Yorkshire pigs (60.3 ± 2.3 kg at surgery) fitted with permanent catheters were included in an incomplete crossover study. The pigs were fed 2 experimental diets for 1–7 d. The diets were rich in PLs and based on nontreated lignan-rich [LR; lignan concentration: 20.2 mg dry matter (DM)/kg] or enzymatically treated lignan-rich (ENZLR; lignan concentration: 27.8 mg DM/kg) rye bran. Plasma concentrations of PLs and enterolignans were quantified with the use of targeted LC-tandem mass spectrometry. Data were log transformed and analyzed with mixed-effects, 1-compartment, and asymptotic regression models.
Results: The availability of PLs was 38% greater in ENZLR than in LR, and the soluble fraction of PLs was 49% in ENZLR compared with 35% in LR diets. PLs appeared in the circulation 30 min after intake of both the ENZLR and LR diets. Postprandially, consumption of ENZLR resulted in a 4-times-greater (P < 0.0001) plasma PL concentration compared with LR. The area under the curve (AUC) measured 0–360 min after ENZLR intake was ∼2 times higher than after LR intake. A 1-compartment model could describe the postprandial increase in plasma concentration after ENZLR intake, whereas an asymptotic regression model described the plasma concentrations after LR intake. Despite increased available and soluble PLs, ENZLR did not increase plasma enterolignans.
Conclusion: The modification of rye bran with cell wall–degrading enzymes resulted in significantly greater plasma concentrations of PLs and the 4-h AUC, particularly syringaresinol, in multicatheterized pigs.
... Hulling, however, decreased the content significantly (0.297 mg per 100 g). 91 A scarcely-studied group of compounds in hemp seeds is lignanamides, which belong also to the lignans. Recently, Yan et al. 92 isolated four new lignanamide compounds. ...
Increasing utilisation of plant protein is required to support the production of protein-rich foods that can replace animal proteins in the human diet so as to reduce the strain that intensive animal husbandry poses to the environment. Lupins, quinoa and hempseed are significant sources energy, high quality proteins, fiber, vitamins and minerals. In addition, they contain compounds, like polyphenols and bioactive peptides that can increase the nutritional value of these plants. From nutritional point, the right combination of plant proteins can supply sufficient amount of essential amino acids for human requirements. This review aims to provide an overview of the current knowledge of nutritional properties, beneficial and antinutritional compounds, storage proteins, and potential health benefits of lupins, quinoa and hempseed.
... (b) Stilbenes are found in red wines, red grape juice and peanuts (Vitrac et al., 2002;Prasad, 2012) while resveratrol is the most common. (c) Lignans: These groups of polyphenols include: secoisolariciresinol found in flaxseed (Ly et al., 2015) and sesamin found in sesame seed (Smeds et al., 2012). (d) Flavonoids could be found in fruits, vegetables, legumes, red wine, and green tea. ...
The incidence of benign prostatic hyperplasia (BPH) is gradually on the increase. While
conventional drugs such as the α1-adrenergic receptor antagonists and 5α-reductase inhibitors
have been found to be useful in the treatment of BPH, the adverse side effects associated with
their usage, have led to increased search for alternative means of managing this disease.
Furthermore, although surgery has also been suggested to be a sure method, the cost and risks
associated with it excludes it as a routine treatment. Dietary polyphenols have gained public
interest in recent times due to their roles in the prevention of various diseases that implicate
free radicals/reactive oxygen species. However, their roles in the management of BPH have
not been explored. Hence this review on their prospects in the management of BPH and their
mechanisms of action. Literature search was carried out in several electronic data bases such
as Pubmed, Google Scholar, Medline, Agora and Hinari from1970 to 2017 to identify the
current status of knowledge on this concept. The findings from these data bases suggest that
while dietary polyphenols may not replace the need for the existing therapies in the
management of BPH, they hold promise in BPH management which could be explored by
researchers working in this field
... High amount of lignans are also found in linseed and sesame seeds (Mazur and Adlercreutz 1998;Sicilia et al. 2003). Smeds et al. (2012) analyzed lignan content in berries and seeds. People get most dietary lignans from beverages, especially from coffee and tea (up to 37%). ...
Red and white grape musts were enriched with 7-hydroxymatairesinol (HMR), which is the main lignan contained in spruce knots. Lignan enrichment was achieved by adding a spruce knot ethanol extract. Enriched musts were stored for 12 months and during storage must samples were periodically analyzed for HMR and alpha-conidendrin content, antioxidant activity, total polyphenols, and anti-mutagenicity. The data were statistically evaluated in order to determine the influence of grape type, quantity of added lignan extracts, addition of sugar, method of preservation and storage time on the quantity of lignans added, antioxidant activity, total polyphenols, and anti-mutagenicity. Lignan content was significantly influenced by the addition of lignan extracts. After storage, lignan content had changed only moderately and the added lignans were stable in the stored musts. Total polyphenol content and antioxidant activity of grape musts were significantly increased by the type of must grape and by thermomaceration. Thermomacerated red musts exhibited higher anti-mutagenicity compared to thermomacerated white musts, independent of lignan addition.
... However, berries are consumed without crushing the seeds. Because the seeds pass through the intestine as such, the bioavailability of berry lignans is low (Smeds et al., 2012). ...
... (b) Stilbenes are found in red wines, red grape juice and peanuts [25,26] (resveratrol is the most well-known) (c) Lignans: Examples are secoisolariciresinol found in flaxseed [24] and sesamin found in sesame seed [27]. ...
The incidence of erectile dysfunction (ED) is on the increase and it is estimated that it will affect about 322 million men globally by the year 2025 if adequate measures are not taken to curb it. Natural polyphenols in plant based diets have gained public interest in recent times due to their roles in the prevention of various disease that implicate free radicals/reactive oxygen species and recently on ED. However, the role of polyphenols in the management of ED has not been explored due perhaps to limited data available. Hence this study which reviewed the role of dietary polyphenols in the management of ED and their mechanisms of action. Literature search was carried out in several electronic data bases such as Pubmed, Google Scholar, Medline, Agora and Hinari from1972 to 2016 to identify the current status of knowledge on the role of polyphenols in the management of erectile dysfunction. Progress made so far in this direction suggests inhibition of arginase, acetylcholinesterase, angiotensin converting enzyme, rho-kinase II; activation of endothelial and neuronal NO synthase; decreased synthesis of luteinizing hormone and testosterone reduction; activation of silent information regulator 2-related enzymes (sirtuin1) as well as free radical/reactive oxygen species inhibition as the mechanisms through which the polyphenols identified in this review exert beneficial roles in the management of ED.
There is a diverse array of berries found wild in tropical, temperate and arid ecosystems or cultivated in both field and control environments across the globe. It is evident berry genetics, species, growth environment, cultivation techniques, postharvest management practices, packaging and processing affect the nutritional and functional properties of berries. The level and composition of functional and nutritional compounds in berries are primarily responsible for their health promotive properties. In particular, anthocyanins and flavonoids are shown to be very effective in managing, treating and reducing CVD risks in humans; and the effects are even more pronounced when combined with personalized nutrition or
diets and physical activities. Globally, there is a steady increase in CVD incidences and associated deaths. There is a need for interventive strategies to reduce these CVD incidences and associated deaths. Personalized nutrition and diets containing increase levels or consumption of fresh berries, berry-based functional foods, nutritional products, or nutraceuticals could be an effective long-term strategy to reduce CVD disease risks, as well as improve population health globally.
Aging is an inevitable, irreversible, and complex process of damage accumulation and functional decline, increasing the risk of various chronic diseases. However, for now no drug can delay aging process nor cure aging-related diseases. Nutritional intervention is considered as a key and effective strategy to promote healthy aging and improve life quality. Small berries, as one of the most common and popular fruits, have been demonstrated to improve cognitive function and possess neuroprotective activities. However, the anti-aging effects of small berries have not been systematically elucidated yet. This review mainly focuses on small berries' anti-aging activity studies involving small berry types, active components, the utilized model organism Caenorhabditis elegans (C. elegans), related signaling pathways, and molecular mechanisms. The purpose of this review is to propose effective strategies to evaluate the anti-aging effects of small berries and provide guidance for the development of anti-aging supplements from small berries.
To explore novel sources of anti-fatigue drugs and food, the anti-fatigue activity of hemp leaves water extract (HLWE) was investigated through exhaustive swimming tests of mice. The median exhaustion swimming time of mice gavaged with HLWE reached 55.4 min, which was 156.8% and 87.8% longer than that of the control group and Rhodiola group, respectively. Then, several biochemical parameters related to fatigue were determined to explore the possible anti-fatigue reasons. The blood lactic acid concentration of mice in HLWE group was 0.76 mmol/L, which was 24.8% lower than that in the control group. Compared with the control group, the glutathione peroxidases activity of mice in HLWE group increased by 296.2%. Based on the results, HLWE exhibited outstanding anti-fatigue activity through reducing the accumulation of lactic acid and improving the activities of defense antioxidant enzymes. It shows appealing potential for development and utilization as novel anti-fatigue food or drugs.
Polyphenols are natural high-valued secondary metabolites of plant that demonstrate strong antimicrobial potential as natural preservatives besides their well-established health promoting benefits. This review highlights the challenges, novel strategies to achieve industrial production of polyphenols and their safe use as potential alternative natural preservative. Since plant extraction presents considerable limitations of high cost due to excessive energy and solvent requirements, climate and long growth cycles, microbial biosynthesis using highly advanced omics techniques and metabolic
engineering tools could provide superior alternative for commercial production of environmentally sustainable and cost-effective high-value metabolites in a short time. In spite of the many beneficial effects, some plant metabolites and polyphenol compounds at high dosage are found to be pro-oxidant or mutagenic with toxicity. Due to the controversial findings from sub-chronic and oral toxicity studies, more detailed safety and efficacy studies are needed to substantiate findings. Furthermore, extensive research efforts are required to ascertain optimal dosage for safe use in various foods to avoid potential harmful side effects.
In the present work new universal bench-scale plant for biosorption, useful in production of new micronutrient biocomponents, was described. The new installation enabling working in a fixed bed or stirred tank batch mode. Reactors may also be used in serial or parallel mode, which gives many application possibilities.
Copper ions were selected as a sorbate for kinetic modelling. The results of the adsorption capacities of Cu(II) were 13.9 mg/g for fixed bed and 12.8 mg/g for stirred tank. During biosorption of Cu(II) ions from aqueous solution ion exchange and release of Ca(II), K(I), Mg(II), and Na(I) were observed. For kinetics description of stirred tank process pseudo-1st-and pseudo-2nd order models were used. For fixed bed process the Thomas, Yoon-Nelson, Adams-Bohart and Wolborska models were used. The use of blackcurrant seed residues as biosorbents enables the generation of new products from waste biomass, which can become an alternative to the traditional fertilizers with microelements. The presented technology is an attempt to reduce environmental impact of the conventional micronutrient fertilizers, which contain toxic chelators such as EDTA. Minimization of waste and maximization of product output makes it an efficient tool supporting cleaner production.
Plant extracts contain large amounts of bioactive compounds, mainly polyphenols. Polyphenols inhibit the growth of microorganisms, especially bacteria. Their mechanism of action is still not fully understood but may be related to their chemical structure. They can cause morphological changes in microorganisms, damage bacterial cell walls and influence biofilm formation. Polyphenols also influence protein biosynthesis, change metabolic processes in bacteria cells and inhibit ATP and DNA synthesis (suppressing DNA gyrase). Due to the antioxidant and antibacterial activity of phenolic compounds, plant extracts offer an alternative to chemical preservatives used in the meat industry, especially nitrates (III). They can inhibit the growth of spoilage and patho-genic microflora, suppress oxidation of meat ingredients (lipids and proteins) and prevent discolor-ation. In this paper, we describe the factors that influence the content of polyphenols in plants and plant extracts. We present the antimicrobial activities of plant extracts and their mechanisms of action, and discuss the effects of plant extracts on the shelf-life of meat and meat products.
Interest in lignans is continually growing in recent years because of their strong antioxidant properties and other biological characteristics, positively affecting human health. Methods for the extraction, identification, and determination of lignans are developed; lignan species and their quantity in food products are determined, and databases of lignans in food products have been created in several countries (Finland, Netherlands, United States, Canada, United Kingdom, Japan, and Spain). In this review, we consider chromatographic methods (gas, liquid, supercritical fluid, and thin-layer chromatography) used to identify and determine natural lignans and isolate them in an individual state. Most natural lignans are found in flax and sesame seeds, cereals, some vegetables, fruits, and berries.
Fruits and vegetables are colourful, flavourful and nutritious components of our diets. Bioactive compounds such as polyphenols, carotenoids, vitamins, phytoestrogens, glucosinolates and anthocyanins present in fruits and vegetables are receiving increased attention because of their potential health benefits. Diets rich in fruits and vegetables may help to delay the ageing processes and reduce the risk of certain types of cancer, cardiovascular diseases and other chronic diseases. The combination of vitamins, minerals, phenolic antioxidants and fibre seems to be responsible for these effects. Nowadays, some authors recommend consumption of fruits and vegetables with high bioactivity, because only such fruits and vegetables are effective in prevention and treatment of various diseases.
High amount of the valuable lignan pinoresinol (PR) was determined in Carduus nutans fruit (7.8mg/g) for the first time. A preparative separation method using two consecutive, identical steps of centrifugal partition chromatography (CPC) was developed in order (i) to isolate PR and (ii) to subsequently isolate PR and its 7' epimer epipinoresinol (EPR) simultaneously after an optimized acid treatment which resulted in PR epimerization forming equal amounts of PR and EPR, from C. nutans fruit. As optimal conditions, a two-phase solvent system consisting of methyl tert-butyl ether:acetone:water (4:3:3, v/v/v) for CPC separation, and an acid treatment performed at 50°C for 30min for the epimerization were applied. Thus, 33.7mg and 32.8mg PR and EPR, in as high as 93.7% and 92.3% purity, were isolated from 10.0gC. nutans fruit, representing 86.4% and 84.1% efficiency, respectively. Conversion characteristic of PR and EPR in acidic medium, determined as a function of time and temperature of acid treatment provides their unambiguous identification by on-line high performance liquid chromatography (HPLC). Antiproliferative assay of isolated PR and EPR in two different types of colon cancer cell lines (HCT116 and SW480) confirmed that both epimers caused a more significant decrease of viability in HCT116 cells than in SW480 cells, suggesting their similar mechanism of antiproliferative action.
Scientific Reports 6 : Article number: 39026; 10.1038/srep39026 published online: 15 December 2016 ; updated: 31 January 2017 . The original version of this Article contained an error in the spelling of Sin-Hyeog Im, which was incorrectly given as Sin-Hyeog Lm.
In a hydrophilic extract of Norway spruce knotwood, the domi-nating lignan, 7-hydroxymatairesinol, was partially removed by precipitation, and the resulting mixture was fractionated by fl ash chromatography and preparative high-performance liquid chromatography (HPLC). In the HPLC fractions, 7 S -and 7 R -todolactol A, 7 ′ -hydroxylariciresinol, and two stereo-isomers of 9 ′ -hydroxylariciresinol were identifi ed by gas chromatography-mass spectrometry (GC-MS) analyses, and their structures were confi rmed by nuclear magnetic resonance spectroscopy. The 9 ′ -hydroxylariciresinols were suggested to have the 7 S ,8 R ,8 ′ R ,9 ′ R and 7 R ,8 R ,8 ′ R ,9 ′ R confi gurations, and (-)-7 ′ -hydroxylariciresinol 7 S* ,7 ′ R* ,8 R* ,8 ′ S* , which indicates a confi guration of this structure that has not been reported previ-ously. 7 S -and 7 R -isoliovil were identifi ed by comparison with previously published GC-MS data, and 7 ′ -oxolariciresinol was tentatively identifi ed on the basis of its mass spectrum. Of these lignans, only 7 ′ -hydroxylariciresinol has been identifi ed previ-ously in Norway spruce. Several other lignans with similar mass spectra as the todolactols, isoliovils, and 7 ′ -hydroxylariciresinol were detected, indicating that they are different stereoisomers of these lignans and/or of liovils. In addition to these lignans, the mass spectra of several other unidentifi ed minor lignans indicated the presence of several tens of previously unidentifi ed minor lignans in Norway spruce knotwood, accounting alto-gether for approximately 6 % of the dry weight of the ethanol extract. 7 S -Todolactol A, which was dominating among the new lignans, was found to be very unstable in aqueous solutions. Identifi cation of more of these unidentifi ed lignans may be pos-sible only by access to pure reference compounds.
Polymerization reactions of the lignans matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhy-drazyl (DPPH) were studied. The reactions were rapid and almost quantitative. The molecular weight distribution (MWD) of the formed lignan dimers and polymers was determined by high-performance size-exclusion chromatog-raphy (HPSEC) combined with evaporative light-scattering detection (ELSD), and the compounds were characterized by HPLC-MS, pyrolysis-GC/MS, NMR, MALDI-ToF-MS, and GC-MS of the monomeric and dimeric units formed by KMnO 4 oxidation. The yield of high-MW polymers is higher for pinoresinol (69%) than for matairesinol (43%). Accord-ing to the HPSEC-ELSD analyses, the MWD is also broader for the pinoresinol polymers. The latter seem to consist main-ly of hepta-hexacontalignans (MW 2.5–21.4 kDa), whereas the matairesinol polymers are mainly penta-pentadecalignans (MW 1.8–5.3 kDa). The polymers seem to contain mainly unmodified lignan units linked by 5-59 bonds. Keywords: 2,2-diphenyl-1-picrylhydrazyl (DPPH); evapo-rative light-scattering detection (ELSD); high-performance size exclusion chromatography (HPSEC); KMnO 4 oxidation; lignan polymers; lignans; MALDI-ToF-MS; matairesinol; pinoresinol; pyrolysis-GC/MS (Py-GC/MS).
Enterolactone (EL) is an enterolignan found in human subjects. In this pilot study, the enantiomeric ratios of serum EL were determined in serum from healthy adults during consumption of habitual diet, and after an 8-day supplementation with flaxseed (25 g/day). (−)EL dominated in all serum samples collected during habitual diet consumption. However, the ratio of (−)EL and (+)EL enantiomers differed markedly between individuals. Flaxseed ingestion increased significantly the proportion of (+)EL in all subjects. Moreover, a small but significant increase in serum (−)EL concentration was measured. After flaxseed ingestion, (−)EL concentrations correlated with those of (+)EL suggesting that the stereochemistry of the parent plant lignan in flaxseed is not a major determinant of EL formation in human subjects. Comparison of EL concentrations obtained with the validated chromatographic methods (HPLC-MS/MS, HPLC-CEAD, and GC-MS) and the time-resolved fluoroimmunoassay (TR-FIA) revealed that the immunoassay method underestimates human serum EL concentrations after the flaxseed ingestion.
Phytoestrogens are secondary plant metabolites that have received increasing attention for their bioactivity, in particular due to their structural and functional similarity to 17beta-estradiol. Although urinary and plasma phytoestrogens can be used as biomarkers for dietary intake, this is often not possible in large epidemiological studies or in the assessment of general exposure in free-living individuals. Accurate information about dietary phytoestrogens is therefore important, but there are very limited data concerning food contents. In this study was analyzed a comprehensive selection of tea, coffee, alcoholic beverages, nuts, seeds, and oils for their phytoestrogen content using a newly developed sensitive method based on LC-MS incorporating (13)C 3-labeled standards. Phytoestrogens were detected in all foods analyzed, although the contents in gin and bitter (beer) were below the limit of quantification (1.5 microg/100 g). Lignans were the main type of phytoestrogens detected. Tea and coffee contained up to 20 microg/100 g phytoestrogens and beer (except bitter) contained up to 71 microg/100 g, mainly lignans. As these beverages are commonly consumed, they are a main source of dietary lignans. The results published here will contribute to databases of dietary phytoestrogen content and allow a more accurate determination of phytoestrogen exposure in free-living individuals.
Sesamin, a major sesame seed lignan, has many biological actions. The specific mechanisms for most of these actions as well as the full metabolic pathway of sesamin in humans are unclear. Two experiments were carried out to determine whether postprandial plasma enterolactone is related to sesamin concentration in sesame seeds and whether enterolactone is the major product of the in vitro fermentation of sesamin. Four subjects (3 women, 1 man) were given a single dose of sesame seeds after they consumed a low-lignan diet for 1 wk. Blood was collected at baseline and at time intervals after intake and plasma was analyzed for plant and mammalian lignan concentrations. Additionally, pure sesamin standard was incubated in vitro with human fecal inoculum to mimic the fermentation process in human gut. We calculated individual pharmacokinetic variables and found high interindividual variation in the plasma plant lignan concentrations. The mammalian lignan appearance rate in plasma shows that sesamin is a major precursor of enterolactone in vivo. In the in vitro experiment, enterolactone was the major metabolite and 3 intermediates were identified, allowing the elucidation of sesamin metabolism in humans. Enterolactone was the major metabolite of sesamin both in vivo and in vitro. The abundance of sesamin in sesame seeds indicates that they are a major food source of enterolactone precursors.
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 microg/100 g), which contained mainly secoisolariciresinol. Also, lignan concentrations in sesame seeds (29,331 microg/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 microg/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 microg/100 g), mainly pinoresinol and lariciresinol. Lignan levels in beverages varied from 0 (cola) to 91 microg/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.
A new lignan diglycoside was isolated from the bark of Eucommia ulmoides OLIV. (Eucommiaceae) and its structure was established as (+)-medioresinol di-O-β-D-glucopyranoside (1) by means of chemical and spectral studies. (+)-Pinoresinol di-O-β-D-glucopyranoside (2), liriodendrin (3) and (+)-pinoresinol O-β-D-glucopyranoside (4) were also isolated.
Knots (i.e., branch bases inside tree stems) in spruce trees contained remarkably higher concentrations of lignans and oligolignans than the adjacent stemwood. The amount of lignans in some knots exceeded 10% (w w ⁻¹ ) and some knots contained hundreds of times more lignans than the heartwood in the same tree. However, there were large variations between different species and even between different knots in the same tree. 7-Hydroxymatairesinol was the predominant lignan in knots of Picea abies, P. glauca , P. koraiensis , P. mariana , and P. omorika , while liovil and secoisolariciresinol dominated in P. sitchensis and P. pungens . The lignans occur in free form in knots and are easily extracted with polar solvents. In addition to the true lignans, especially the knots contained large amounts of lignan-related oligomeric aromatic substances, here called oligolignans, consisting of three or four phenylpropane units.
7-Hydroxymatairesinol, but also other lignans, could be extracted in large scale from spruce knots at pulp and paper mills. Other potentially important lignans could be produced from 7-hydroxymatairesinol by semisynthesis. The ready availability of large amounts of lignans and oligolignans now enables research to assess their bioactivity and provide the basis for applications in medicine and nutrition or as natural antioxidants and antimicrobial agents in a variety of technical products.
The hydrophilic and lipophilic extractives in the heartwood of knots from 7 Norway spruce trees were analysed by GC, GC-MS and HPSEC. The knots contained extremely large amounts of lignans, 6-24 % (w/w), with hydroxymatairesinol comprising 65-85 % of the lignans. Even the knots of the young trees contained 4-8 % (w/w) of lignans. The variation in the amount of lignans was large among knots, both within a single tree and between trees. In addition to the lignans, knots also contained 2-6 % (w/w) of a complex mixture of lignan-like compounds with 3,4 and even up to 6 phenyl propane units, here called oligolignans. The amounts of lignans in the knots were similar in the radial direction from the pith into the outer branch, but decreased dramatically outwards in the branch, almost disappearing after 10-20 cm. The ratio of the 2 epimers of hydroxymatairesinol differed between different knots and even within the knot. A new spruce lignan, nortrachelogenin, or its enantiomer, wikstromol, was detected in knots from trees in northern Finland as opposed to samples from southern Finland. ne amount of lipophilic extractives was small compared to the amount of hydrophilic extractives in the knots. Five of the dead knots contained more resin acids and free diterpenyl alcohols than ordinary stemwood. In the other knots, the amount of lipophilic extractives was on the same level as stem heartwood. The stem sapwood contained larger amounts of esterified fatty acids than the knots.
Edible plants contain a number of natural compounds which mimic the biological effects of oestrogens by virtue of their ability to bind to and activate the nuclear oestrogen receptors. These hormone-like diphenolic phyto-oestrogens of dietary origin include isoflavonoids, coumestans and lignans. Our interest in these phyto-oestrogens derives from the results of epidemiological studies on diet and Western diseases including hormone-dependent cancers as well as coronary heart disease. Incidences of the diseases in question are lower in peoples of Asia compared to inhabitants of industrialized American and European countries. Using isotope dilution gas chromatography-mass spectrometry method we have identified and measured in foods the precursors of the biologically active compounds detected in plasma of subjects living in areas with low cancer incidence. Biochanin A, formononetin, daidzein, genistein, and coumestrol, and the lignans matairesinol and secoisolariciresinol have been found to possess oestrogenic, anti-oestrogenic, antioxidative, antiviral, antibacterial, insecticidal or fungistatic properties and they have been shown to be antiproliferative in relation to many types of tumours in cell culture. We report quantitative results for these plant oestrogens measured in soybeans and other legumes, oilseeds and nuts, grain and cereals, berries and fruits, cruciferous, allium and other vegetables, and beverages such as tea and coffee.
Leaf and stem material of Forsythia intermedia contains four main lignans and their O-glucosides. These were identified as the dibenzylbutyrolactone derivatives (−)-arctigenin, arctiin [(−)-arctigenin 4′-O-glucoside], matairesinol and (−)-matairesinol 4′-O-glucoside, together with the furofuran lignans (+)-phillygenin, phillyrin [(+)-phillygenin 4-O-glucoside], (+)-epipinoresinol and (+)-epipinoresinol 4′-O-glucoside. The lignan contents varied according to tissue type and season. Full spectral data for the lignans are presented. The 1H NOE difference spectra recorded for phillygenin and epipinoresinol necessitate the reversal of earlier chemical shift assignments for axial and equatorial protons on C-9 of furofuran lignans having one axial and one equatorial aryl group (the epi series).
Twenty-four plant lignans were analyzed by high-performance liquid chromatography−tandem mass spectrometry in bran extracts of 16 cereal species, in four nut species, and in two oilseed species (sesame seeds and linseeds). Eighteen of these were lignans previously unidentified in these species, and of these, 16 were identified in the analyzed samples. Four different extraction methods were applied as follows: alkaline extraction, mild acid extraction, a combination of alkaline and mild acid extraction, or accelerated solvent extraction. The extraction method was of great importance for the lignan yield. 7-Hydroxymatairesinol, which has not previously been detected in cereals because of destructive extraction methods, was the dominant lignan in wheat, triticale, oat, barley, millet, corn bran, and amaranth whole grain. Syringaresinol was the other dominant cereal lignan. Wheat and rye bran had the highest lignan content of all cereals; however, linseeds and sesame seeds were by far the most lignan-rich of the studied species. Keywords: 7-Hydroxymatairesinol; syringaresinol; lignans; cereals; rye bran; wheat bran; HPLC-MS/MS; accelerated solvent extraction
The variation in the contents of sesamin and sesamolin was studied in oils extracted from 65 samples of sesame seeds (Sesamum indicum L.) from plants with shattering (n=29), semishattering (n=7), and nondehiscent (n=29) capsules. The oil content ranged from 32.5 to 50.6% and was greater in white than black seeds (P<0.001). The sesamin and sesamolin contents in seeds ranged from 7 to 712 mg/100 g (mean±SD, 163±141 mg/100 g) and from 21
to 297 mg/100 g (101±58 mg/100 g), respectively, with no difference between black and white seeds. Thus, there was a wide
variation in the contents of sesamin and sesamolin, which were positively correlated (R
2=0.66, P<0.001). There were negative correlations between the contents of sesamin and the contents of sesaminol (R
2=0.37) and sesamolinol (R
2=0.36) and between the content of sesamolin and those of sesaminol (R
2=0.35) and sesamolinol (R
2=0.46) (P<0.001). Sesame seeds had an average of 0.63% lignans, making them a rich source of dietary lignans.
The oil content, the tocopherol composition, the plastochromanol-8 (P-8) content and the fatty acid composition (19 fatty acids) of the seed of 51 hemp (Cannabis sativa L.) genotypes were studied in the 2000 and 2001 seasons. The oil content of the hemp seed ranged from 26.25% (w/w) to 37.50%. Analysis of variance revealed significant effects of genotype, year and of the interaction (genotype year) on the oil content. The oil contents of the 51 genotypes in 2000 and 2001 were correlated (r = 0.37**) and averaged 33.19 1.45% in 2000 and 31.21 0.96% in 2001. The -tocopherol, -tocopherol, -tocopherol, P-8- and -tocopherol contents of the 51 genotypes averaged 21.68 3.19, 1.82 0.49, 1.20 0.40, 0.18 0.07 and 0.16 0.04 mg 100g–1 of seeds, respectively (2000 and 2001 data pooled). Hierarchical clustering of the fatty acid data did not group the hemp genotypes according to their geographic origin. The -linolenic acid yield of hemp (3–30 kg ha–1) was similar to the -linolenic acid yield of plant species that are currently used as sources of -linolenic acid (borage (19–30 kg ha–1), evening primrose (7–30 kg ha–1)). The linoleic acid yield of hemp (129–326 kg ha–1) was similar to flax (102–250 kg ha–1), but less than in sunflower (868–1320 kg ha–1). Significant positive correlations were detected between some fatty acids and some tocopherols. Even though the average content of P-8 in hemp seeds was only 1/120th of the average -tocopherol content, P-8 content was more closely correlated with the unsaturated fatty acid content than -tocopherol or any other tocopherol fraction. The average broad-sense heritabilities of the oil content, the antioxidants (tocopherols and P-8) and the fatty acids were 0.53, 0.14 and 0.23, respectively. The genotypes Fibrimon 56, P57, Juso 31, GB29, Beniko, P60, FxT, Flina 34, Ramo and GB18 were capable of producing the largest amounts of high quality hemp oil.
The lignan enterolactone, produced by the intestinal microflora from dietary precursors, has been implicated in protection against cancer. We investigated the association of serum enterolactone concentration with the risk of acute coronary events in a prospective nested case-control study in middle-aged men from eastern Finland.
Enterolactone was measured by time-resolved fluoroimmunoassay in serum from 167 men who had an average 7.7 years of follow-up to an acute coronary event and from 167 control men. Both cases and controls were from a cohort of 2005 men who had no clinical coronary heart disease (CHD) at baseline. The controls were matched for age, examination year, and residence. Acute coronary events were registered prospectively.
The mean baseline serum enterolactone concentration was lower among the cases than the controls (18.2 [SD 21.1] vs 23.5 [18.2] nmol/L, p=0.001). The men in the highest quarter of the enterolactone distribution (>30.1 nmol/L) had a 58.8% (95% CI 24.1-77.6, p=0.005) lower risk of acute coronary events than men in the lowest quarter. After adjustment for the nine most strongly predictive risk factors, men in the highest enterolactone quarter had a 65.3% (11.9-86.3, p=0.03) lower risk than men in the lowest quarter.
Healthy men with high serum concentrations of enterolactone had a lower risk of acute coronary events than men with lower concentrations. These findings support the hypothesis that plant-dominated fibre-rich food lowers the risk of CHD.
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To characterize the range of variation in lignan content and composition caused by genotype and environment, seven dietary lignans, i.e., 7-hydroxymatairesinol, secoisolariciresinol, matairesinol, lariciresinol, pinoresinol, medioresinol, and syringaresinol, were analyzed by high-performance liquid chromatography-tandem mass spectrometry in whole-grain extracts of cereal samples collected at eight locations in Finland. In all, 28 winter rye, 73 spring wheat, and 55 spring oat samples were analyzed, representing 6, 9, and 5 cultivars, respectively. The total lignan content showed huge variations within the same cereal species: the range was 2500-6700 microg/100 g in the rye samples, 340-2270 microg/100 g in the wheat samples, and 820-2550 microg/100 g in the oat samples. The variations seemed to depend largely upon genetic differences. In rye, also environmental conditions affected the lignan content through grain size; smaller grains had significantly lower total lignan, syringaresinol, and lariciresinol content than larger grains. This study shows that varying cereal lignan concentrations reported in different studies may be, besides differences in analytical methods, largely dependent upon natural variations.
Quantitative data on phyto-oestrogen, particularly lignan, content in edible plants are insufficient. We, therefore, measured isoflavonoids and lignans in nine edible berries using an isotope dilution gas chromatography-mass spectrometry method for foods and found substantial concentrations of the lignan secoisolariciresinol (1.39-37.18 mg/kg DM), low amounts of matairesinol (0-0.78 mg/kg DM) and no isoflavones. To determine pharmacokinetics and urinary excretion pattern of the mammalian lignan enterolactone derived from plant lignans, a study with human subjects was conducted. Five healthy women and two men consumed, after a 72 h period of a phyto-oestrogen-free regimen, a single strawberry-meal containing known amounts of plant lignans. Basal and post-meal blood and urine samples were collected at short intervals. The samples were analysed using time-resolved fluoroimmunoassay of enterolactone. The meal increased plasma concentration of enterolactone after 8-24 h and in urine in the 13-24 h and 25-36 h urine collections. High individual variability of the metabolic response was observed. Enterolactone excreted in the urine collected throughout the 48 h post-meal yielded on average 114% of the plant lignans consumed. It is concluded that berries containing relatively high concentrations of plant lignans contribute to plasma and urinary levels of mammalian enterolactone in human subjects.
The quantity of mammalian lignans enterolactone (ENL) and enterodiol (END) and of plant lignans secoisolariciresinol (SECO) and 7-hydroxymatairesinol (HMR) excreted in a 24-h rat urine sample was measured after a single p.o. dose of an equivalent quantity of secoisolariciresinol diglycoside (SDG), secoisolariciresinol (SECO), matairesinol (MR), 7-hydroxymatairesinol (HMR) and ENL. Plant lignans (SECO and HMR) were partially absorbed as such. The aglycone form of SECO was more efficiently converted into mammalian lignans END and ENL than the glycosylated form, SDG. Of plant lignans, MR produced the highest quantities of ENL: the quantity was over twofold compared with HMR or SDG. The majority of the animals, which had been given SECO, excreted higher quantities of END than ENL into urine, but ENL was the main lignan metabolite after SDG. The highest quantities of ENL in urine were measured after the administration of ENL as such. The (-)SECO isolated from Araucaria angustifolia was converted into (-)ENL only. The administration of (-)SDG, which was shown to produce (+)SECO, resulted in excretion of (+)ENL only and (-)HMR was converted into (-)ENL only. This confirmed that the absolute configurations at C8 and C8' are not changed during the microbial metabolism. Whether the biological effects are enantiomer-specific, remains to be resolved.
Camelina sativa-derived oil (camelina oil) is a good source of alpha-linolenic acid. The proportion of alpha-linolenic acid in serum fatty acids is associated with the risk of cardiovascular diseases. We studied the effects of camelina oil on serum lipids and on the fatty acid composition of total lipids in comparison to rapeseed and olive oils in a parallel, double-blind setting. Sixty-eight hypercholesterolemic subjects aged 28 to 65 years were randomly assigned after a 2-week pretrial period to 1 of 3 oil groups: camelina oil, olive oil, and rapeseed oil. Subjects consumed daily 30 g (actual intake, approximately 33 mL) of test oils for 6 weeks. In the camelina group, the proportion of alpha-linolenic acid in fatty acids of serum lipids was significantly higher (P <.001) compared to the 2 other oil groups at the end of the study: 2.5 times higher compared to the rapeseed oil group and 4 times higher compared to the olive oil group. Respectively the proportions of 2 metabolites of alpha-linolenic acid (eicosapentaenoic and docosapentaenoic acids) increased and differed significantly in the camelina group from those in other groups. During the intervention, the serum low-density lipoprotein (LDL) cholesterol concentration decreased significantly by 12.2% in the camelina oil group, 5.4% in the rapeseed oil group, and 7.7% in the olive oil group. In conclusion, camelina oil significantly elevated the proportions of alpha-linolenic acid and its metabolites in serum of mildly or moderately hypercholesterolemic subjects. Camelina oil's serum cholesterol-lowering effect was comparable to that of rapeseed and olive oils.
Evidence is emerging that dietary phytoestrogens play a beneficial role in obesity and diabetes. Nutritional intervention studies performed in animals and humans suggest that the ingestion of soy protein associated with isoflavones and flaxseed rich in lignans improves glucose control and insulin resistance. In animal models of obesity and diabetes, soy protein has been shown to reduce serum insulin and insulin resistance. In studies of human subjects with or without diabetes, soy protein also appears to moderate hyperglycemia and reduce body weight, hyperlipidemia, and hyperinsulinemia, supporting its beneficial effects on obesity and diabetes. However, most of these clinical trials were relatively short and involved a small number of patients. Furthermore, it is not clear whether the beneficial effects of soy protein and flaxseed are due to isoflavones (daidzein and genistein), lignans (matairesinol and secoisolariciresinol), or some other component. Isoflavones and lignans appear to act through various mechanisms that modulate pancreatic insulin secretion or through antioxidative actions. They may also act via estrogen receptor-mediated mechanisms. Some of these actions have been shown in vitro, but the relevance of these studies to in vivo disease is not known. The diversity of cellular actions of isoflavones and lignans supports their possible beneficial effects on various chronic diseases. Further investigations are needed to evaluate the long-term effects of phytoestrogens on obesity and diabetes mellitus and their associated possible complications.
Phytoestrogens of the lignan type are widely distributed in plant-derived food items and are believed to protect against hormone-dependent cancer. The richest known dietary source of lignans is flaxseed. Flaxseed has been reported to contain glycosides of secoisolariciresinol as the major lignan, together with small amounts of matairesinol, isolariciresinol, and pinoresinol. Secoisolariciresinol, but none of the other lignans, has so far been identified in pumpkin seeds. In the present study, two different methods for the hydrolysis of lignan glycosides are compared. Artifact formation and loss of lignans under acidic conditions were observed. Lariciresinol was identified by GC-MS analysis in two different types of flaxseed (Linum usitatissimum L. and Linum flavum L.) and in pumpkin seeds (Cucurbita pepo L.) for the first time. Likewise, the novel lignan demethoxy-secoisolariciresinol was tentatively identified in the flaxseed samples. Stereochemical analysis by chiral HPLC of several lignans isolated from flaxseed showed that secoisolariciresinol, matairesinol, and lariciresinol consisted predominantly of one enantiomer.
Five lignans, five neolignans, two sesquilignans, and a dilignan were identified from a phytotoxic extract of Brassica fruticulosa L. Compounds 8, 9, 12, and 13 have been isolated for the first time. Structures were determined on the basis of their spectroscopic features. Their effects on the germination and growth of two dicotyledons, Lactuca sativa (lettuce) and Lycopersicon esculentum (tomato), and a monocotyledon, Allium cepa (onion), as standard target species have been studied.
The antioxidant potency and the radical scavenging capacity of superoxide and peroxyl radicals were assessed for 13 hydrophilic knotwood extracts of commercially important wood species, or fractions thereof, as well as for five pure wood-derived lignans and the flavonoid taxifolin. The chemical composition of the knotwood extracts was determined by gas chromatography combined with mass spectrometry. Most of the investigated wood species were rich in hydrophilic extractives (10-20% of the dry wood) with one or a few compounds dominating in each extract. All extracts had a high antioxidative potency and/or radical scavenging capacity as compared to the well-known antioxidants Trolox and butylated hydroxyanisole. The pure wood-derived lignans and taxifolin also had a high antioxidative potency and/or radical scavenging capacity. However, the antioxidant potency and/or radical scavenging capacity of several of the hydrophilic knotwood extracts were higher than that of the dominating compounds in pure form.
The paper describes a method for the determination of selected lignans in plant foods. First, samples were submitted to methanolysis resulting in cleavage of ester bonds between lignan glycosides and organic acids. Glycosidic linkages were then broken by enzymatic hydrolysis using cellulase. The released aglycones were separated isocratically (acetonitrile/10 mM sodium acetate buffer, pH 4.8, 225:775, v:v) by reversed phase high performance liquid chromatography (RP-HPLC) and the compounds were detected coulometrically at four electrodes set on potentials between +260 and +330 mV against palladium reference electrodes. The selectivity and sensitivity of the method allowed quantitation of the lignans secoisolariciresinol, lariciresinol and isolariciresinol in various foodstuffs down to the upper ppb-range with recoveries between 44.7 and 97.0%. Unidentified peaks displaying similar current-voltage curves (CVCs) as the investigated lignans indicated the presence of further possible lignan representatives. In addition, investigation of various foodstuffs involving enzymatic hydrolysis with and without preceding methanolysis showed that the degree of esterification of lignans in plant foods is species dependent.
Phytoestrogens may play a role in hormone-related diseases such as cancer, but epidemiological and clinical data are conflicting in part due to inadequate databases used in intake estimation. A database of nine phytoestrogens in foods relevant to Western diets was developed to more accurately estimate intakes. Foods (N = 121) available in Ontario, Canada were prepared as commonly consumed and analyzed for isoflavones (genistein, daidzein, glycitein, formononetin), lignans (secoisolariciresinol, matairesinol, pinoresinol, lariciresinol), and coumestan (coumestrol) using gas chromatography-mass spectrometry methods. Data were presented on an as is (wet) basis per 100 g and per serving. Food groups with decreasing levels of total phytoestrogens per 100 g are nuts and oilseeds, soy products, cereals and breads, legumes, meat products, and other processed foods that may contain soy, vegetables, fruits, alcoholic, and nonalcoholic beverages. Soy products contain the highest amounts of isoflavone, followed by legumes, meat products and other processed foods, cereals and breads, nuts and oilseeds, vegetables, alcoholic beverages, fruits, and nonalcoholic beverages. Decreasing amounts of lignans are found in nuts and oilseeds, cereals and breads, legumes, fruits, vegetables, soy products, processed foods, alcoholic, and nonalcoholic beverages. The richest sources of specific phytoestrogens, including coumestrol, were identified. The database will improve phytoestrogen intake estimation in future epidemiological and clinical studies particularly in Western populations.
Sea buckthorn (Hippophaë rhamnoides) seeds, berries, and berry fractions are often used as sources of bioactive ingredients for health products. The aim of the present study was to analyze lignans in these fractions of sea buckthorn. Secoisolariciresinol and matairesinol in seeds, fruit pulp/peel, and whole berries of sea buckthorn of three subspecies were analyzed by isotope dilution gas chromatography-mass spectrometry. The total content of the two lignans secoisolariciresinol and matairesinol varied widely from 8 to 139 microg/100 g in fresh berries and from 51 to 319 microg/100 g in dry berries. The content of secoisolariciresinol varied in the range of 34-313 microg/100 g of dry mass in the fruit pulp/peel and 93-355 microg/100 g in dry seeds. The content of matairesinol fell within the range of 3-25 microg/100 g in dry pulp/peel and 1-13 microg/kg in dry seeds. Wild H. rhamnoides ssp. sinensis contained a significantly higher total level of secoisolariciresinol and matairesinol in dry seeds, dry berries, and fresh berries compared with wild ssp. rhamnoides (253 vs 135 microg/100 g, P < 0.01, in seeds; 224 vs 153 microg/100 g, P < 0.05, in dry berries; 71 vs 29 g/100 g, P < 0.01, in fresh berries) and the cultivar of ssp. mongolica (253 vs 112 microg/100 g in seeds, 71 vs 9 microg/100 g in fresh berries). Harvesting dates had a significant influence on the content of the two lignans in seeds, fruit pulp/peel, and whole berries. This is the first report of lignans in sea buckthorn.